It’s something I’ve carried with me throughout the past 14 years, and it’s a truth I’ve seen illustrated throughout my work and entertainment—like movies.

Take The Devil Wears Prada, for example. Inspired by Anna Wintour, former Editor-in-Chief of Vogue, the film follows Andy Sachs—an ambitious journalist thrust into the world of high fashion when she lands an assistant role at the world’s most prestigious magazine.

It’s the opportunity of a lifetime, and Andy runs with it. Hard. She transforms her wardrobe, sacrifices her relationships, and bends herself into whatever her formidable boss, Miranda Priestly, needs her to be—all in service of an opportunity she never stopped to interrogate.

She’s on the treadmill from the first scene.

Until she finally steps off in Paris.

At the height of her fashion world “success,” Andy registers she’s been running toward a finish line she never stopped to question. She understands that chasing an opportunity for the sake of opportunity is an unwinnable game. She gets honest with herself about where she actually wants to be, and suddenly, every decision she’s been wrestling with becomes clear.

It’s a feeling most of us recognize, especially as a founder or CEO.

In today’s edition, I’ll break down why and how being more deliberate about where you’re going can save you months, if not years, of unnecessary struggle.

Every personal and professional journey has two fixed points: Point A is where you are now, Point B is where you’re going.

Point A is easy to define if you’re willing to give yourself a good hard look in the mirror. Point B demands the same honesty—but it’s harder to define because you’re trying to envision what doesn’t exist yet. Most founders have a vague sense of it at best, and that’s not their fault.

This is as true for content as it is for anything else. “I should be creating content” is not a Point B. Neither is “I want to build my brand” or “I want to create more opportunities.” These feel like answers but they function like non-answers. They’re the content equivalent of Andy taking the job at Runway magazine—a compelling opportunity, sure. But not a strategy.

Without a strategy, you end up exactly where Andy spent most of the film—reactive, exhausted, and making decisions from anxiety rather than intention. That energy comes through in your content. Viewers sense the difference between founders who know exactly where they’re taking them and those still figuring it out.

Clarity Is the Strategy

Inspired by Anna Wintour—the most powerful woman in fashion—Miranda Priestly is the most strategically clear person in The Devil Wears Prada. She runs Runway with an iron grip and almost supernatural sense of direction. Her clarity is what enables her to be so decisive, ruthless, and unflappable.

There’s a scene early in the film where Andy, still adjusting to the world of high fashion, makes the mistake of laughing at what she assumes is a trivial debate over two nearly identical blue belts.

Miranda stops her cold. In under two minutes, she reverse engineers the exact journey of the cerulean blue cardigan Andy’s wearing at that very moment—tracing it from a designer’s runway decision, to the pages of fashion magazines, to department store shelves, and finally to the discount bin where Andy unknowingly picked it up.

To Andy, the belts were barely distinguishable. To Miranda, the entire critical path was obvious. Decisions are easy when you always know where things are going.

That’s the energy founders are aiming for in their content. Not Miranda’s particular brand of terrifying—but that groundedness. The sense of someone who knows exactly what they’re building and why. People respect it.

The Framework

Getting there requires working at two levels—and asking the same type of question at both.

The Macro Level

What measurable outcome is your content is building toward? Not “build my brand,” but something observable enough that you’d know if it was working. How many inbound leads per month? What number of newsletter subscribers by what date? If you can’t point to it and say “that happened” or “that didn’t,” it’s not a Point B yet. A vague outcome puts you on an endless treadmill.

The Micro Level

What observable action do you want someone to take after viewing a particular post? Not “feel inspired,” but something you can actually track. “Subscribe to my newsletter. Download this lead magnet. Schedule a demo.” If you don’t know what you want someone to do, they won’t know either.

Same question, same rigour applied at different altitudes. When your individual posts (micro level) are consciously serving your macro outcome, content stops feeling like a treadmill and starts functioning as a strategy.

In learning design, we call this Backward Design—and it’s one of the first things I walk founders through when we start working together. Start with Point B, identify Point A, and then work backwards. What’s critical versus “nice to have” becomes obvious.

If you want to see Backward Design in practice, I made a video applying it to course creation—the principle translates directly to content:

Side note: This is a perfect example of evergreen content. I recorded this video nearly three years ago and it's still just as relevant today.

The Universal Point B

Every post you make, every framework you share, every insight you put into the world is building toward one thing: a direct line to your audience. Not likes. Not impressions. But the ability to reach your target audience directly in their inbox—without an algorithm deciding whether or not they see it.

Social media is rented visibility. An email list is owned real estate. Each post should move someone a step closer to that direct relationship. The sooner you design toward it, the more intentional everything becomes.

This brings us back to Andy's turning point in Paris.

Forced to confront the person she’s become and reevaluate Point B, Andy decides to make a change. She visualizes the destination she wants to run toward, and does exactly that by walking away from her role with Miranda.

Andy didn’t need a perfect plan to walk away from one of the most coveted jobs in fashion. She needed to get honest with herself about her Point A and Point B.

Your content doesn’t need to be perfect either. It just needs a Point A and Point B.

Start there.

Thanks for reading and have a wonder-full week,

Alexandra

P.S. This newsletter started as a LinkedIn post. A few people found it helpful enough that I turned it into an evergreen post I can point founders to in the future (like my video on Backward Design).

Forced to rebuild their lives from a motel in a small town, O’Hara plays Moira, the Rose family matriarch.

Moira is an actress herself who, despite a career setback on the heels of her financial loss, carries on as if nothing has changed—sporting her couture wardrobe and collection of wigs with her signature red lipstick, unplaceable accent, and grandiose vocabulary.

Based on the flood of Moira memes across Instagram in the weeks following O’Hara’s passing, it goes without saying she had countless iconic moments. But my favourite Moira moment is when she shows up to comfort Stevie—the young motel owner who the Rose family takes in as their own—after she’s been dumped.

Stevie is wiping away tears with the flannel sleeve of one of many oversized shirts she wears like a uniform—a major contrast from the Rose family who dress to impress every day of their lives and liken sweat pants to a hate crime—when Moira shows up at her door with a bottle of wine and a script.

After Stevie chalks up her breakup to “Turns out, someone who’s been working the front desk of a motel her whole life isn’t exactly a turn-on,” Moira, never one to use a simple word where a grander, self-invented one would do, responds, “Stevie, underneath the brambly tartan blousant is a chrysalis, just bursting with potential.”

Moira hands Stevie a script for Cabaret, telling her that she too once found herself stuck in a “podunk routine,” and Cabaret was the “gift” that jolted her out of it.

Stevie, confused, responds “I’m not an actress...” to which Moira is quick to say “Neither is the lead in the play. She’s simply a headstrong young woman, who’s been knocked about a few times, and… looking to make the most of herself.”

Moira asks Stevie if she can sing and Stevie replies hesitantly, “I sing in the car.”

Moira nods, “Good enough.”

Then swiping the wine she brought, she turns on her designer heel and struts out, leaving Stevie to peruse the script.

What follows is Stevie dreading every rehearsal, trying to back out, and secretly rehearsing with another choreographer because Moira alone isn’t enough to get her there.

Backstage before her final scene, Moira touches up Stevie’s makeup as she tells her, “Stevie, I’m so proud of you. You’re really powering through tonight. Of course I never doubted you.” Stevie’s response is pure Stevie, “Thank you, but I still have an act and a half to prove you wrong.”

She walks out anyway, and brings the house down as Moira wells up backstage, watching the person she believed in before that person believed in herself.

It’s one of the most moving moments in the whole series—and, oddly enough, one of the most insightful for any founder or CEO.

Your Cabaret

Most CEOs and founders have wisdom that’s been in the wings so long they’ve forgotten it belongs on stage—frameworks they’ve spent years developing, hard-won lessons that could save others years of pain, and points of view their industry has never quite articulated.

Most haven’t shared any of it.

But think about what actually convinced Stevie to pick up the script. It wasn't Moira’s star power. Stevie already knew Moira was an internationally celebrated actress. She’d heard the stories, seen the photos, watched the grand entrances. That didn’t move her.

What did was learning that Moira had started where she was—in a podunk town with a mundane routine.

Without that crucial detail, the script is just a script handed down from someone who exists in a completely different world.

Your origin story works exactly the same way.

Your wins make people admire you. Your origin story makes them trust you. And trust is what makes them think: “This person gets it. They’ve been where I am. This is who I want in my corner.”

I first experienced this in 2021, when I started sharing my experience with project management and online writing. A local university reached out asking if I’d teach workshops for their students and recent graduates, and that snowballed into landing clients from startups in Canada, the US, and Europe.

All because I started showing up consistently long before I knew who was watching.

The People in the Dark

Most CEOs don’t realize that 90% of LinkedIn users never engage with anything publicly. But they’re there. Reading your posts at midnight, forwarding them to a colleague, mentioning your name in a meeting you’ll never know happened.

When those people reach out, they’re pre-sold. They’ve decided you’re credible, so the call is a formality rather than a pitch.

The goodwill you share doesn’t just help others, it compresses your sales cycle.

Moira didn’t know what showing up at Stevie’s door would set in motion. She just remembered what it felt like to be stuck, and had something that might help.

That’s all it takes.

You don’t know which post will be someone’s Cabaret. You don’t know which idea will make someone think differently about their business, or pick up the phone, or mention your name in a room you’ll never be in.

You just have to keep showing up.

If you’re sitting on years of hard-earned wisdom and still telling yourself you’re not ready, you don’t have time, or that you only sing in the car, take it from Moira:

“Good enough.”

Thanks for reading and have a wonder-full week,

Alexandra

I’d never given feedback on so many people’s work in such quick succession, and my pattern spotting was amplified in a way editing my own work never was.

Funnily enough, other people’s mistakes held up a mirror to my own. That’s why I keep coming back to the post embedded below.

The problem with generic writing hasn’t changed—the culprit has.

AI is now a rookie editor by default, and unless prompted otherwise, it will counterintuitively make your writing worse.

Spoiler alert: it’s not because it adds em dashes—which were widely used from Austen to Hemingway, and mirror how many of us talk.

Here’s why AI is actually a threat to good writing:

What’s your experience using AI as an editor? Has it helped or hurt your writing?

Feel free to share your thoughts (and favourite prompts) in the comments.

Thanks for reading and have a wonder-full week,

Alexandra

Sunday, I walked to Encore Books & Records, my local secondhand bookshop, resolved to find two people I’d been indifferent to a couple of months ago. I was looking for John F. Kennedy Jr. and Carolyn Bessette in the biography section after bingeing the first four episodes of Love Story, the new Disney+ series inspired by their romance—amplified for dramatic effect.

I came up empty, as I often do when a series prompts a resurgence in popularity of public figures. But I had to smile at the realization I was exhibiting every sign of buyer psychology and a marketing framework I teach daily.

Here’s how:

For the past few months, JFK Jr. and Carolyn Bessette had been showing up more and more in my social media feeds—both as fictional TV characters and in paparazzi photos from the ‘90s. I’d see John biking around NYC in a tailored suit with a backwards baseball cap or Carolyn strolling through Manhattan in a chic all-black ensemble contrasted by her signature red lips and honey blond hair.

Over the years, I’d heard about the famous couple’s untimely passing and had come across their names in bookstores and TV shows, like Sex & The City, where Carrie and Charlotte gushed over John as “the sexiest man alive.”

I knew the couple was considered American royalty as part of the Kennedy clan, and they were the son and daughter-in-law of former first lady and eternal style icon Jackie O. Above all, I knew their lives were cut tragically short, similar to Princess Diana’s.

But a dramatized series about their relationship wasn’t something I was particularly interested in (I felt the same way about The Crown’s portrayal of the Royals before I watched it).

The promotional photos that initially popped up on my Instagram feed, featuring the actors in near-identical outfits to the couple’s most iconic paparazzi shots, struck me as inauthentic. “Carolyn’s” hair was too blond, and “John” looked too naive.

I scrolled past.

But day after day, as the volume of famous and fictitious images increased, I found myself pausing and swiping through images, intrigued by the fashion and mystique of the “iconic NYC couple” a quarter-century after their fatal plane crash in 1999.

I saw side-by-side comparisons of headline-breaking news reenactments, from the couple’s famous fight in Washington Square Park to Bessette’s “bottomless blond” humiliation after she was photographed in her underwear on Kennedy’s boat. I also learned Kennedy failed the New York bar exam twice through promotional footage recreating tasteless headlines, like “THE HUNK FLUNKS… AGAIN.”

As the weeks went by, I saw the series promoted through commercials, and though my interest grew, I thought, “Well, I don’t have a Disney+ subscription, so I can’t watch it anyway.”

Again, I pushed it out of my mind.

But then last week, I saw posts cropping up all over Twitter with people raving about how good the first few episodes are. The chemistry, the ‘90s fashion, the music. Hell, the smoking.

“Okay, I’m going to watch it,” I thought to myself.

So when I got home Saturday evening, after baking a cake and celebrating my sister’s birthday, I promptly subscribed to Disney+ for $8 and binged all four episodes.

I woke up on Sunday and gushed to my sisters and friends how good the series is, and how excited I was for the next episodes. I also looked up the most popular biographies on Kennedy and Bessette and felt compelled to visit Encore Books to see whether they had any going spare.

I came up empty, but I realized something important.

If I reverse-engineer how I went from “passive observer” to “paying subscriber” and “eager book buyer,” I see two interconnected concepts at play.

The first is the mere exposure effect—a psychological phenomenon discovered by researcher Robert Zajonc in 1968 that states familiarity generates liking. In other words, the more you’re exposed to something, the more familiar it becomes, and the more you’re inclined to like it—often without even realizing it.

The second is the 7-11-4 framework popularized by entrepreneur Daniel Priestley and backed by Google, which states that before someone feels ready to do business with you, they typically need seven hours of engagement with your content across eleven touchpoints on four different platforms. This occurs gradually over time.

If we trace my path from passively scrolling Instagram in November to my Disney+ subscription in February and my visit to Encore Books on Sunday, every marker is there. I had repeated exposure and well over seven hours of engagement with JFK Jr. and Carolyn Bessette-related content through dozens of touchpoints across Instagram, TV, Twitter, bookshops, and news articles I looked up to verify facts like JFK’s bar failure.

So by the time Saturday night rolled around, subscribing to watch the show was less a decision and more a natural next step.

And I’m clearly not alone in my quest to read more about the famous couple. Book recommendations are in no short supply.

This isn’t the first time I’ve experienced the mere exposure effect or 7-11-4 framework. A few weeks ago, I was helping my sister rearrange her bookcase when I spotted a book I thought I’d lost years ago when I left London. It was British model and fashion designer Alexa Chung’s It and I distinctly remember how she piqued my interest in George Harrison by distinguishing him from his Beatles bandmates as a “natural-born clothes horse.”

At the time, Harrison was the only Beatle I couldn’t name, but upon learning he was a style icon and dark horse often overshadowed by his more extroverted bandmates, he remained somewhere at the back of my mind.

He popped up again years later in a TASCHEN book on London that I was gifted for my birthday, and after bingeing his documentary and first solo album, I wound up buying a newly minted biography on him.

Granted, it was a much slower process, but it was the same mere exposure meets 7-11-4 combination. Repeated exposure across multiple contexts built familiarity, familiarity tipped into genuine interest, and genuine interest turned into real investment. Harrison is now my favourite Beatle.

The reason I share these examples of how I went down the rabbit hole on Kennedy, Bessette, and Harrison is that most founders and CEOs I work with underestimate the long game involved in personal branding, also known as “CEO-led marketing.”

You can’t just post a few times and expect immediate results, or assume your audience isn’t interested in what you have to say.

Even your most loyal followers won’t see every post. You have to show up consistently for several months for the mere exposure effect and 7-11-4 framework to run their natural course.

Be prolific, but also be patient. And show up as yourself—not just your best headshot. I initially dismissed Love Story because the promotional photos looked too staged. But once I actually watched it, I understood what all the fuss was about. The characters were fun and dynamic. Give yourself that same grace.

P.S. I already converted two friends into fans of Love Story within 24 hours of watching it.

I love when I’m reminded of the power of willing something into being.

Back in the fall, one of my favourite Pilates instructors shared a behind-the-scenes look at the studio she shares with her photographer husband, describing it as a “gift from God” to be able to build their businesses so close to home and prioritize family time with their young son.

I thought it was such a beautiful scenario.

Little did I know that over the Christmas holiday, I’d be radiating gratitude for my own “gift from God.”

Having become increasingly eager to move out of the city, my first thought toward the end of last year was, “I need to find a remote dream job.”

But I flopped back and forth between feeling excited and feeling flat every time I thought about my job prospects. I knew I wanted to be working at the intersection of my obsessions: writing/editing, entrepreneurship, and teaching/coaching.

But what that role looked like—let alone what it was called—was beyond me. I certainly wasn’t going to find it on a job board.

Like most roles I’ve had since I graduated in 2012 and wound up working with the Managing Director of a law firm after sending her a cold email, I knew I’d have to be proactive about creating an opportunity for myself.

I was resolved to will it into being. And that’s what I told my friends.

Then one day… a former client-turned-friend texted me a link to an informal post on LinkedIn.

The company was looking for someone to help busy B2B CEOs create a month’s worth of LinkedIn content in just 1-2 hours per month.

They’d developed an interview model to position the CEO as an expert in their field by turning their answers into a mix of short-form content: videos, writing, graphics.

I had a coffee chat with my friend’s husband to learn more about the role and company, and quickly realized it was the exact opportunity I didn’t know I was looking for. One that would allow me to combine my obsessions with writing/editing, entrepreneurship, and teaching/coaching.

And it was 100% remote.

I couldn’t believe my luck.

Fast forward through a trial assignment and several interviews, and I wound up accepting their offer before 2025 drew its final curtain.

I started the job two weeks ago after wrapping up my latest chapter with an amazing team—and all I keep thinking, with a smile no less, is “This job is a gift from God.”

Why This Role Even Exists

Nowadays, everyone wants to know who the boss is. Not only that, but they want to be able to binge their content to understand how they think and operate. Transparency equals trust.

Most CEOs and founders get this and know they should be showing up consistently on LinkedIn. But between running a business, managing a team, and a hundred other things they’re losing sleep over, content creation gets pushed to the back burner.

When they do try to post, it’s hard. The barrier to entry isn’t just about time—it’s psychological. I saw this time and time again with the 50+ founders and creators I helped launch courses over the past few years through Maven and my small-group coaching program. Not to mention the hundreds of founders and executives I mentored through David Perell’s Write of Passage program.

Every single one of them—and every one of us who's worked hard to become a great leader—has the same fear about getting started with content creation: “I don’t want to sound dumb,” and “I don’t want to look cringey.”

When I started this newsletter four-and-a-half years ago, you would’ve thought I was sending rockets into space the way I nervously hit ‘Publish’ each week. For the first couple of months, I massively overthought everything from what I wrote to how I formatted it. Ironically, I had ten subscribers at the time, and they were fellow writer friends who were supportive as hell.

As time went by and more readers subscribed, I can’t pinpoint when I stopped feeling nervous—all I know is it took several months to gain confidence, knowing full well that my writing wasn’t good yet, but each week it was incrementally better.

My motto was “practice equals progress,” and I encourage anyone starting to create content to stick with it long enough to see the compounding effects.

The pressure to sound smart and look polished off the bat makes content creation a bigger mind game than it ought to be.

This is where the interview model changes everything.

From Long-Form Purist to Understanding the Ecosystem

When I started writing online in February 2021, I was a long-form purist. My love of writing stemmed from my love of reading, and by nature, I love to explore ideas deeply, let stories breathe, and take my time getting to the point.

But over the past few years, I’ve come to appreciate something I initially resisted: short-form content provides a stepping stone for people to discover your deeper work.

I first started writing on Medium, and I was deeply appreciative of the outpouring of encouragement from family and friends. But after the novelty of my first few posts wore off, I experienced the inevitable “dip” every content creator faces, when people who aren’t your target audience naturally lose interest, and you feel like you’re posting into the void.

That’s when it clicked for me: my writing matters to me, and I need robust guidance and feedback to improve it and reach my target audience.

So I joined Dickie Bush and Nicolas Cole’s Ship 30 for 30—a course where you write and publish a short-form post every day for 30 days alongside a cohort of peers.

The concept was simple: progress over perfection. Build the writing muscle, embrace the cringe, and most importantly, get over your fear of shipping. After 30 days, you’ll have established thought patterns, built consistency, and then you can focus on getting better.

Ship 30 led to Write of Passage—a writing program focused on long-form content, which included launching this newsletter. My first cohort as a student led to mentoring, then editing for the program.

At the same time, I developed expert skills for facilitating online workshops and courses which in turn led to my role as Head Coach for the Maven Course Accelerator. And from there, I became comfortable creating async video tutorials.

Each step built naturally on the previous one, and there was a compounding effect that improved my communication skills across the board.

But everything started with that struggle of trying to jump into long-form content without support. It was tough—and intellectually lonely. I now see huge value in getting people started on short-form and letting them build up from there.

Think about it, most people won’t give a second glance to a 2,000-word essay written by a stranger—let alone read it. But they will stop scrolling for a punchy LinkedIn post that resonates. They’ll watch a 60-second video that catches their eye and makes them think differently. They’ll save a graphic that captures an idea they’ve been struggling to articulate.

And that’s precisely how they’ll discover you. Next, they’ll find your newsletter, or your latest thoughtful essay, and eventually, your full entrepreneurial story.

Through bingeing your content, they’ll go from “casual observer” to someone who cares about what you have to say. They’ll become invested in your journey as much as your company’s.

While different platforms serve different purposes, LinkedIn is the universal starting line. It’s where everyone’s hanging out, which means it’s where you need to show up consistently.

Give them something valuable in a format they can consume quickly, and then bring them deeper into your world.

That’s exactly what I help CEOs do now.

Four Principles I Swear By

My approach to helping CEOs and founders create content is built on four principles that have fundamentally changed my life and so many around me over the past few years:

1. Write from Conversation

The best content is conversational and matches how you actually talk—not corporate jargon or AI slop. I learned this from David Perell as a mentor for Write of Passage.

“Writing from conversation is the art of using dialogue to identify your best ideas and double down on them.”

—David Perell, Creator of How I Write podcast

This is why the interview model works so well. We don’t ask CEOs to sit down and write from a blank page. We brainstorm questions their prospective clients would have, outline their responses using a simple copywriting framework, and then record them talking through their responses in a way that feels natural to them. And then we edit the videos to punch up the messaging as best as possible.

This approach lowers the barrier to entry while creating a jumping-off point for complementary copywriting and graphics.

2. Aim for ‘Eyes Light Up’ moments

The best messaging sparks an undeniable, visceral reaction from your target audience. I learned this from Wes Kao as Head Coach for the Maven Course Accelerator, and it’s become a guiding principle in everything I do.

“I call this the Eyes Light Up moment. This is the moment when your audience is viscerally, undeniably excited about what you’re talking about.

That is the reaction you’re looking for. Whenever you tell a story, share your value proposition, or test your positioning/messaging.”

—Wes Kao, Co-founder of Maven

I help founders pinpoint Eyes Light Up moments and build their content strategy around them.

3. Carve out ‘sacred hours’

Time-blocking your calendar during peak energy periods is the undisputed way to get high-value work done in the shortest amount of time—ideally through a flow state.

Ship 30 for 30 co-founder Dickie Bush calls these “sacred hours” and you must protect them at all costs.

The key to consistently creating content is to have a system and allocate the necessary time each month to brainstorm, record your videos, and approve the final content. You can do this in as little as two hours a month, but those two hours can easily bleed into much more if you don’t give them the focus they require.

4. Focus on ‘steak’ over ‘sizzle’

One of my biggest takeaways from working with startup coaches at District 3 Innovation Centre from 2020 to 2021 was:

“The difference between founders who make it and those who don’t is largely determined by their ability to focus on ‘steak over sizzle’—and it’s a lot harder than it sounds.”

If you want to go viral or chase vanity metrics, I’m not your go-to person. But if you want content that speaks to your ideal customers and drives real business results, that’s where I thrive.

Why I’m Excited

A little over two years ago, I wrote about being at a major crossroads in my solopreneur journey. I was struggling with the isolation of working alone, missing the energy of being part of a team, but also not wanting to give up on everything I’d built.

This new role supports me as an employee while empowering me to be an entrepreneur. The company’s philosophy is “you are the CEO of your career”—you’re entrepreneurial, you own your outcomes, but you’re doing it alongside a team. It’s exactly the middle ground I’ve been looking for.

And the role sits at the intersection of my obsessions.

I get to coach founders through their content journey, helping them find their voice and build confidence in showing up online. I get to support entrepreneurship—working with people building businesses they’re passionate about. And I get to do the writing and editing work I love, turning raw conversations into polished content.

Plus, it's 100% remote, which means I'm one huge step closer to the future I'm envisioning of moving out of the city, and adopting a slower, more intentional lifestyle like the one I grew up with in the Laurentians.

The Long and Short of It

My Substack is where I share my long-form deep dives—my full story of how I got here and why this work matters to me.

Next, I’ll distill this post for LinkedIn. I’ll pull out the key insights, and might even turn them into a carousel or a short video.

This is the content ecosystem in action: short-form and long-form working together. One drives attention, while the other adds depth. One creates the entry point, while the other delivers the experience.

I’m really grateful and excited to be back doing this work.

Thanks for reading and have a wonder-full week,

Alexandra

Rewatching Gilmore Girls 20 years later has me thinking about how the internet has changed the small town vs. big city trope.

Rory’s journey captures a narrative that defined life before the internet could bridge geographic divides: if you’re ambitious, you have to physically leave your small pond to swim with bigger fish. Rory went from being the top student at Stars Hollow High to getting a D on her first paper at Chilton, an elite Hartford prep school.

Her mother, Lorelai, faced the same constraint, commuting to Hartford for business studies to realize her dream of opening an inn in lieu of managing one in Stars Hollow.

By Rory’s graduation, Lorelai had earned her business degree and was purchasing property for her inn. Rory was named class valedictorian and described living in “two worlds” in her speech.

But the internet can now bridge those two worlds.

Today, any intellectually curious teenager or aspiring business owner in a small town with internet could take online courses, engage with people worldwide, and access many of the same resources as people in Manhattan. They could build expertise through online communities and publish their work to gain recognition—without leaving home.

I’ve experienced the power of that bridge myself.

I grew up in a small ski town and moved to Montreal at 17 for my post-high school education (CEGEP and university). Growing up, my extended family was mostly in Montreal, so I always recognized the contrast between the “city” and the “country.” Things like going to a shopping mall were a trek from our small town, whereas they were a convenience for my cousins in the city. Conversely, learning how to ski was a convenience for my siblings and me, while our cousins mostly tumbled down the slopes.

After graduating from university, I worked in London, Sydney, and Paris before eventually returning to Montreal.

But had it not been for the internet powering remote writing programs like Write of Passage, Montreal’s much smaller size compared to London, Sydney, and Paris—not to mention returning during the pandemic—would’ve prevented me from connecting with a global community of writers who helped me improve my craft and inspired me to keep writing.

The internet also gave me the opportunity to pursue my dream of remote self-employment by working with global clients, which allowed me to learn from top industry players I never would’ve had access to based on geographic factors and cross-border visa requirements.

And here’s what’s fascinating—this shift has completely changed what people want. Lately, friends of mine who’ve lived in cities their entire lives and done stints in big cities like London or New York have told me they’re tired of city life and seriously plotting moves to Stars Hollow-esque areas. Meaning charming, walkable areas with strong communities and an abundance of nature, but close enough to the city for convenience.

I get it.

After 18 years of city living, as much as I’ve loved the opportunities and conveniences, lately I feel like I’ve overdosed on city life and find myself daydreaming of returning to the slower, healthier pace I grew up with, having a house and a backyard to write, garden, and spend time with family and friends.

I got a taste for it last week when I spent a few days working remotely from my sister’s place outside the city, helping her with her kids while my brother-in-law was away. I couldn’t help but marvel at how calm I felt waking up to the sight of trees and sounds of birds rather than the sight of condo buildings and the sounds of traffic. There was joy in pushing the stroller down abundantly green streets where neighbours waved and called “Morning!” from their tenderly cared-for properties. Sitting out in the backyard with my coffee, writing my book while my niece slept peacefully next to me, made me realize how much I yearn for a different lifestyle—one that bridges the incredible upbringing I had in a small ski town with infinite opportunities accessible through my laptop.

The Gilmore Girls were forced to choose between two worlds at all times, but now small towns have their inherent advantages, while the internet has solved many of their traditional disadvantages.

I feel very grateful and inspired by that.

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My Oxford Year had prime real estate as a new release, and given my love of the UK, writing, and romcoms, I was easily sold on a love story against the backdrop of a poetry class at Oxford. I clicked ‘Play’ expecting pleasant background noise while I re-energized, wholly unprepared for what unfolded—the same way I felt watching Me Before You for the first time, when I settled in with minimal expectations only to wind up sobbing by the end as though I’d suffered a personal loss.

The heartbreaking beauty of both book-inspired films is their exploration of thinking you’re living deliberately versus actually doing it.

And that crux has completely reframed my own UK-inspired book project.

The Pitfalls of Planning

Both Anna in My Oxford Year and Louisa in Me Before You begin their stories believing that living deliberately means having a solid plan rooted in security—something I can relate to wholeheartedly.

Anna arrives at Oxford with carefully mapped academic goals, a lengthy bucket list, and a deferred job opportunity at Goldman Sachs in New York City. Louisa is living in a cramped family home with her parents, her sister Treena, and Treena’s young son Thomas while working at a café to help support everyone following her father’s job loss.

Both Anna and Louisa, ages 24 and 26, have their worldviews rewired when confronted with new people and places.

Anna learns from Jamie, her terminally ill poetry professor-turned-boyfriend, that planning isn’t what Thoreau meant by “living deliberately.” It's about being where your feet are, because savouring each moment, no matter how messy and uncertain life gets, is what makes us feel most alive.

Louisa learns from Will, her quadriplegic employer and former heartthrob who lived an incredibly worldly life before his accident, that real, deliberate living is about recognizing your own worth and refusing to settle for the smallest possible version of yourself.

Both women learn to be present in uncertainty rather than rushing toward some imagined resolution.

I learned the same lesson at 24 when I got rejected from law school. In a span of 24 hours, I went from feeling like a failure as the “safest” path ahead disappeared from sight, to feeling free to pursue my dream of moving to London as the quiet question of “What would I do if I could do anything right now?” allowed me to tap into my intuition.

I’ve often wondered why that memory was so profound. Now I realize... asking myself that question was the moment I started living deliberately.

The Evolution of a Story

When I started my book project twelve months ago, I planned to write a memoir about moving from Montreal to London at 24 and all the transformative people and places I encountered. It seemed like the most natural extension of how I’d been using my Substack as a picture window, sharing my entrepreneurial journey over the previous three years.

But as I started writing, I realized I wanted to maintain privacy for myself and others. At first, that felt like a problem since I was compelled to strip out intimate details that robbed my stories of their spirit.

But then I decided to reframe the problem as an opportunity: I could pursue creative liberty by switching genres. Memoir demands fidelity to literal events, but as recently reminded me, “a good novel amplifies what is true.” So a few months ago, I landed on a fictional concept inspired by my experience, rather than limited to it.

While Anna and Louisa learned that the best experiences can’t be planned down to the last detail, I’ve learned that the best stories sometimes outgrow their original containers.

From Seeds to Something

I had a surge of enthusiasm about my new concept when I landed on it. But over the past few weeks, I’d been second-guessing whether a story inspired by my experience of finding myself through failure and beginning to live deliberately at 24 would resonate with the thoughtful, established readers I’ve connected with through my Substack.

But watching My Oxford Year reminded me that coming-of-age-abroad stories are timeless because they inevitably teach you what Paulo Coelho describes beautifully:

“The journey is not about becoming anything, but to unbecoming who you are not.”

Coelho’s quote inspired the first online post I ever wrote—on Medium in February 2021—about my decision to chase a dream that had been lying dormant behind a practical path. Four years later, that very post has inspired my forthcoming novel, Unbecoming.

The Power of Perspective

At 35, I feel every emotion the films My Oxford Year and Me Before You evoke more acutely than I would have in my twenties. Looking back on those pivotal years I spent in London becomes more poignant over time, and I feel inspired by my younger self’s willingness to leap into uncertainty.

Reflecting on my experience through the lens of fictional characters like Anna and Louisa makes it abundantly clear that “quarter-life crises” are actually a rite of passage. For many of us, it’s the first time we question whether the path we’re on is actually ours and not a well-trodden path we’ve been conditioned to follow.

What looks like recklessness to family and friends (“Why are you throwing away stability for uncertainty?!”) is often the first deliberate choice we make to honour our authentic selves. The perceived “crisis” isn’t the problem, but rather a solution to living on autopilot.

Despite a heap of Instagram posts and my grandmother continuously asking “how’s your holiday?” throughout my two-year tenure abroad, those who were part of my London life got to see what most people didn’t—what my Aussie flatmate-turned-best friend called “character-building” challenges.

One uncharacteristically sunny day a few months in, she and I sat in the back garden of another Aussie friend’s new “gaff,” shaking our heads and laughing at the stressful stretches wedged between picturesque Instagram posts.

Whether it was my stress-induced heartburn when the initial flat I’d secured turned out to be contaminated with mold—leaving me displaced and depleted as I struggled to get my deposit back, my flatmate walking into an accounting firm for a role she was due to start after a strenuous job hunt only to have the recruiter phone her on arrival saying she’d mixed her file up with someone else’s, or our other friend being flummoxed by her first London dinner date suggesting they split the bill, we were all continuously wrestling with setbacks or situations that contradicted what we’d grown accustomed to back home.

That’s where the transformation really happened, incrementally over time.

The more I’ve shared my story, the more I’ve realized it resonates with others. A Substack subscriber-turned-friend in her fifties always tells me how my London stories take her back to her expat years in Japan. “I can’t wait to read your book,” she’ll say. I finally understand why.

Stories about learning to live deliberately resonate across decades.

A few weeks ago, I stumbled upon a $9 copy of The Palace Papers in the midst of re-reading Harry Potter.

Now by day, I'm absorbed in Tina Brown’s royal exposé, an addictive read that makes my commute seem inconveniently short, and by night, I'm immersed in The Goblet of Fire, reliving the same struggle I had as a kid to put the book down and go to sleep. Incidentally, I now see how masterfully J.K. Rowling has cloaked the mystique and pageantry of British aristocratic traditions in magic.

The parallels are everywhere. Harry Potter is tormented by the Daily Prophet, while Prince Harry is tormented by the Daily Mail. The Sorting Hat mirrors royal investitures. Houses at Hogwarts work exactly like houses at Eton. And “pure-blood” families cast out nonconformist relatives the way the royals exiled Edward VIII.

Having been a Londoner myself many years ago, I now appreciate the connections with a keener eye for the class undertones that readers outside the UK might miss.

Grand Castles, Grander Traditions

Both worlds revolve around magnificent, borderline mythical buildings that aren’t merely locations, but characters. Hogwarts, with its moving staircases and watchful portraits, could be Windsor Castle’s magical cousin. These aren’t just schools or homes; they’re living, breathing institutions whose walls whisper centuries of secrets.

The boarding school tradition goes far beyond academics to create a complete social ecosystem where lasting identities and lifelong bonds are formed. Most readers don’t realize that Hogwarts’ house system isn’t merely inspired by elite English boarding schools like Eton—it may as well be them dressed up in magic. The house rivalries and tribal loyalty of belonging to Gryffindor vs. Slytherin are prime examples of how Rowling translated reality.

Personified Properties

In both worlds, properties don't merely have addresses; they have names that carry serious weight. Think Clarence House, Sandringham, Balmoral in the royal realm, or Grimmauld Place, Malfoy Manor, The Burrow in the wizarding world. Each name reflects its dwellers’ social standing.

The Pageantry of Power

Hierarchy isn’t merely reflected by property names—it’s paraded through elaborate ceremonies and traditions. The Sorting Hat ceremony at Hogwarts serves the same purpose as royal coronations or investitures. And the pomp and circumstance aren’t merely for show; they’re how these communities show everyone exactly where they stand.

I witnessed this firsthand at Trooping the Colour for the Queen’s birthday—a massive military parade with thousands of spectators culminating in the choreography of the royal family on the Buckingham Palace balcony for an RAF flyover with the Queen at the centre, and the most senior royals in the most coveted spots by her side. The sheer scale and precision of this annual event are as much a display of power and hierarchy as they are a celebration.

Secrets, Sabotage & Scorekeeping

The exclusivity extends beyond public ceremonies. A friend of mine went through the recruitment process to work for the royal household, and it was so rigorous and confidential that there were rumours she was interviewing for Sir Elton John. I was stunned to learn otherwise. As a denim-clad roadie friend put it when I told him over drinks, “That’s bigger than rock’n’roll. That’s the fucking Queen.”

That level of secrecy extends to how these institutions handle internal competition. The house cup competition in Harry Potter mirrors the constant competitive undercurrent behind palace doors—who’s more popular, who’s doing their duty better, who’s winning the public’s favour. It’s all very civilized on the surface, but there’s intense scorekeeping (and alleged sabotaging) simmering at the core.

Blood, Lineage, and the Ultimate Insider Club

Perhaps most tellingly, both worlds are obsessed with bloodlines and heritage. The pure-blood families in Harry Potter—the Blacks, the Malfoys, the Lestranges—have their family trees, coats of arms, and inherited prejudices, just like the royal family with their carefully documented ancestry and bloodline.

Class markers show up in the smallest details and the most discriminatory comments. I once had a colleague who travelled with luggage bearing his family crest—a form of understated status signalling that both worlds excel at.

Another colleague who had proudly told me about her distant royal bloodline connections made a face as though she’d just sucked on the bitterest lemon when I asked about our latest recruitment candidate. “Eugh, her Scouse accent,” she said, shaking her head as if warding off the memory. It was completely out of character for someone I’d known to be kind and polite. I was dumbfounded to learn that as a Canadian, I was spared ingrained class biases that still constrain many Brits.

Both the wizarding and royal worlds create insider vs. outsider dynamics where knowing the right protocols, speaking the right language, and understanding the unspoken rules mark you as belonging—or not. The wizarding world has its spells and magical terms, and the royal world has its forms of address and byzantine etiquette that might as well be magic to the uninitiated.

Perhaps the most extreme form of outsider is the nonconformist who finds themselves burned from their pure-blood family tree. Sirius Black’s banishment from his family in Harry Potter was surely inspired by the royals’ exile of Edward VIII following his abdication from the throne.

Both parties ruthlessly prune threats to their carefully maintained order. As the former king concludes in the drama series The Crown, “With this family, when you’re in, you’re never quite sure that you’re in. But when you’re out, there’s no doubt at all. You’re out.”

The Fame Game

Fame operates by the same brutal rules in both worlds. Both Harry Potter and the royals (particularly Prince Harry and Meghan at present) are simultaneously revered and criticized, with devoted followers and harsh critics analyzing their every move. The press attention, the lack of privacy, the weight of expectations—there’s no respite for the famous.

Reading about Prince Harry’s struggles with Daily Mail coverage alongside Harry Potter’s saga with the Daily Prophet creates a meta commentary on fame itself—and the UK’s obsession with tabloid gossip.

Rowling’s Real Magic

Rowling took exclusive, hereditary British traditions and made them magical and (somewhat) meritocratic. She democratized the fantasy of aristocratic life by making it accessible through wit and bravery rather than merely bloodline.

Unbeknownst to most readers, Harry Potter’s global appeal stems from its translation of British class structures into something universal: the desire to belong to something grand and meaningful, and to be part of traditions bigger than ourselves. As much as Rowling invented a magical world, she largely decoded an existing one.

Season’s greetings everyone,

I hope you’re feeling merry and bright as we rev up to the holidays!

Here’s what’s new with me post two-month (newsletter) writing hiatus, plus some ideas on how to maximize wellness this holiday season by keeping things simple and inexpensive.

Book Update 📖

First thing’s first, I’m still working on my book though admittedly, I’ve been cheating on writing with Pilates.

Having sustained an injury over the summer that prevented me from working out, I’ve been on a mission to get back in shape this fall. And in a bid to go gentler on my body, I’ve ditched my former HIIT routine and reconnected with my long-lost love of Pilates.

I’m a few months in and I feel incredible.

And so, despite originally thinking I’d have the first draft of my book written by Christmas and being nowhere close to that, I’m proud of my progress.

As part of my slower, steadier approach to pursuing my goals following my burnout in summer 2023, I’m pacing myself for optimal quality of life.

I love writing and don’t want to rush the process. So my revised game plan is to have my first draft written by Christmas 2025.

I’m excited to take time over the next couple of weeks to map out my writing schedule to that end.

I have missed writing to you weekly though.

So I also want to think about how I can resume writing my newsletter at a gentler cadence, say every three or four weeks. I’ll fill you in on my ETA once I figure it out.

Holiday Staples (Steeped in Wellbeing) 🍵

When I picture Christmas shopping on steroids, I remember walking down Oxford Street in London in 2014 and wandering around Galeries Lafayette in Paris in 2018.

That and my pre-Christmas visit to New York in 2021 (I ended up with COVID but thankfully, made it back across the border before testing positive).

As fascinating as it’s been to see the world’s most famous cities take on Christmas commercially, it’s made me realize how easy it is to lose sight of what’s really important.

Thoughtfulness trumps cost when it comes to giving and receiving.

I recently turned thirty-five and my favourite gifts to give and receive are those steeped in well-being.

I especially love self-care products, journals, hand-painted mugs, seasonal teas, and sentimental ornaments (like the “Luke’s coffee mug” a friend sent me given our shared love of Gilmore Girls).

I also love writing and receiving cards. It’s a dying art and I’m doing my best to keep it alive (although the Canada Post strike is killer at the moment).

In any case, thoughtful gestures are your most valuable Christmas gifts.

Feel Good Vibes For 2025 ✨

Most New Year’s resolutions take a nose-dive in February or March once the inevitable “dip” in motivation sets in. But those who power through follow a similar trajectory to what’s known as “hockey stick growth” in the startup world.

The key to “sticking” with things is reducing friction.

(Pun unintended, though totally on brand. I am Canadian after all—despite my pitiful knowledge of hockey.)

James Clear explains the impact of reducing friction in his best-selling book, Atomic Habits. (A book that fundamentally changes how you think about habits and helps you rewire your environment to make good ones easy to stick with and bad ones easy to break.)

I’ve been reducing friction around my goals and priorities since I read Atomic Habits in 2021, and getting back into Pilates this fall was no exception.

Here are a few things I did to ensure my ramp-up to three classes a week would be easy, enjoyable, and sustainable (I guarantee you can make your goals attainable if you think through similar factors):

1. Timing ⏰

The first thing I did was determine the best time to book my Pilates classes. Back when I was in my early twenties, you couldn’t pay me to get up early to workout before work. I was a night owl and opted for evening classes instead.

But now? I’m the opposite.

I’m officially a morning person and while 10 am would be my ideal time to workout (and that was my golden fitness hour during my self-employment era when I had the flexibility to make my schedule), now I have to factor in the 9 to 5 schedule, so 7:30 am classes are my go-to.

Occasionally, when I opt for an evening class due to a schedule conflict, I notice a huge change in my energy (though I enjoy mixing it up once in a while, especially to add coziness to our longer, darker evenings).

But the takeaway is more energy equates to more enthusiasm to workout and better performance. So bear that in mind when you’re planning out practices of your own. Make it easy.

2. Commute 🚎

The second thing I thought about was how I’d get to and from classes.

Reducing friction means keeping my commute short to prevent delays or lack of motivation due to a perceived “trek” ahead. Also, when it comes to morning classes, the longer the commute, the earlier you have to wake up.

In my case, I have a studio within a ten-minute walk of my apartment. Ideally, I’d do all my classes there but it’s primarily a yoga studio so they don’t have a lot of Pilates classes outside of the 9 to 5 schedule.

I had to find an additional studio to hit my quota of three classes per week.

Through a quick search, I discovered a bunch I’d never even heard of and did a few trials, which I highly recommend as photos can be deceiving and it’s best to see what the vibe is in person.

Originally, I thought a studio near my work would be the best option but upon trialling it, I learned they don’t have changing rooms and on top of that, I would have to take the metro extremely early which then poses the safety issue of going underground when it’s dark and not many people are around.

So that studio got nixed.

Instead, I found a studio that’s a six-minute bus ride from my nearest metro station (or a thirty-minute walk). It’s on the way to work too, so I can easily continue my commute to the office afterward.

3. Enjoyment 🤩

The third thing I did was take stock of my enjoyment from class to class and week to week.

See here’s the thing, you won’t know if you enjoy something until you try it.

One of my biggest takeaways from working at a startup hub is to adopt an entrepreneurial mindset, you have to think of yourself as an experimenter continuously testing your hypotheses. That’s the key to validation and everything else is feedback you can use to reassess.

Picking a workout routine is no different. You may think you’ll love spinning, strength training, or yoga because “all your friends do” or it’s “what everyone in your industry does.” But until you try it, you won’t know.

So try things but be honest with yourself about whether or not they’re really your thing.

Forcing yourself to do something you know is good for you but you don’t enjoy will never amount to doing something you love that provides similar benefits, as you’ll always be motivated to work that much harder in the latter case.

Case in point, people remark how “disciplined” and “committed” I am when I tell them about my Friday 7:30 am Pilates class and it’s funny to me since it’s without a doubt one of the easiest aspects of my week (the motivation to get there that is—the class itself is gruelling but I love the challenge, most days).

My question to you is, what’s something you do for yourself that has you hopping out of bed on Friday mornings when most people would prefer to hit “Snooze”?

There’s nothing wrong with the latter (TGIF and all that), but if you find the former, you’ve found your “thing.”

Make time for your thing this holiday season and beyond.

You’ll shine brighter for it.

Happy holidays,

Alexandra

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Like most kids who grew up in the ‘90s, back when Oprah aired prime time at 4 pm, I picked up the odd tip from the talkshow titan when my mum attempted to listen but rarely sat down.

(I’m one of four kids.)

One of my biggest takeaways was from an episode on managing your wardrobe.

The rule of thumb was “Every time you add something to your wardrobe, you have to get rid of something else.”

Simple enough, right?

Wrong.

To put it bluntly, hoarding crap in your closet is a universal flaw.

Just think of every time you’ve protested parting ways with something because you might wear it someday.

Now think of every time you’ve struggled to find something in your closet because your heavily draped hangers were squished together, or you’ve wrestled an overstuffed drawer.

The worst, right?

The problem with holding onto stuff we don’t need while simultaneously adding more is we create conditions of cramming and overflow—which we internalize.

This leads to feelings of frustration and overwhelm as we go about our daily tasks (like getting dressed).

Thus, as Oprah preached 20 years ago, whatever is merely taking up space must be removed.

And her advice applies as much to your workload as it does to your wardrobe.

Workload Example

A month ago, I announced I was working toward my childhood dream of writing a book.

Upon congratulating me, several friends and family members added “You’ll have to stop your newsletter then.”

My initial reaction was “No.”

I was adamant about keeping it going since it’s been my biggest passion project and growth enhancer over the past three years.

I envisioned my book as an additional project I was fully capable of integrating since I can write and edit my newsletter faster now than when I started publishing 36 months ago.

But last weekend proved otherwise.

Despite allocating my Saturday to write (an opportunity I’d been sorely lacking), I couldn’t muster the energy to do so.

I wound up making a much healthier decision than I would’ve 18 months ago (before I stopped grinding and embraced a slower, more balanced pace of life).

I decided to have a well-deserved lazy day.

Instead of working on my book, I binged Nobody Wants This (which totally lives up to the hype) and had copious cups of tea by the fire.

It felt incredible to prioritize rest and upon reflecting on my slower-than-expected progress after five weeks of working on my book, I’ve finally come to terms with reality:

As long as I keep writing my weekly posts, my book writing will be shortchanged.

I’ve hit my stride with my weekly posts over 3 years and 151 editions.

Now it’s time to “refresh” my workload.

I have no desire to wrestle with “drawers and hangers” in the coming months, so I’ve made an important decision.

I’m hitting ‘Pause’ on my weekly Substack posts. From now until Christmas my book will be my priority on the writing front.

I’m excited about this change for two reasons.

Firstly, I’m proud of myself for the changes I’ve made over the past 18 months.

After burning out in summer 2023, I vowed to never extinguish my flame again. And following an injury in May that left me unable to work out for months, I am extremely grateful for my morning Pilates classes now.

A lot of supposed experts on Twitter claim you have to get up and write every morning to succeed.

But I’m at a point in my writing journey where I benefit from days off.

The past year and a half have reinforced the importance of harmony across all aspects of life and when one aspect starts to override the others, it’s important to rein it in to maintain an overall flow (FYI control and flow are core principles of Pilates).

Secondly, I’m proud of myself for knowing it’s time to “graduate” and move on to a bigger project.

It’s time to move the goalposts further.

Here’s a visual of my favourite soccer player “bending” the ball around every obstacle to highlight my goal (though full disclosure, I don’t watch soccer and “married a Spice Girl” is a large part of my “favourite player” attribution):

Read More of My Posts

In honour of my hitting ‘Pause’ after 3 years and 151 weeks of publishing, I’ve rounded up my favourite posts for you. So when you find yourself craving a slice of my Substack, check out the links below or peruse my archive.

I’ve grouped posts by theme below.

On Navigating Career Challenges

Here are seven of my rawest posts on overcoming challenges over the past three years:

1. The Paradox of Freedom. On the tradeoffs between being an employee and early-stage entrepreneur.

2. A Major Crossroads in My Solopreneur Journey. On being at a crossroads between getting a job and sticking with self-employment.

3. Therapy, Self-Awareness & Entrepreneurship. On succumbing to anxiety and burnout and seeking help to get back to myself.

4. Why I Wouldn't Delay Solopreneurship Because You’re Single. On not deferring dreams by waiting on “ideals.”

5. The Pain of Looking Back & The Power of Moving Forward. On reluctantly learning from the past and creating a better future.

6. Personal Brand, Professional Opportunities. On why I'm invested in tying my identity to my name.

7. My Big Break (And The Identity Shift Behind it). On the need for adequate support as an entrepreneur.

(Those who’ve been reading my writing since Fall 2021 can attest I’ve come a long way in infusing the personal into the professional. Through consistent effort, I’ve made enormous strides.)

On Empowerment, Healing & Well-being

1. Act It Out. On asking for what you want and being willing to walk away from alternatives.

2. Stumble & Stabilize. On the price of developing a new skill and finding peers to “stumble” with.

3. The Art of Healing. On fusing cracks in our lives with gold and celebrating our uniqueness.

4. Take Care of You. On being your own advocate at work and in healthcare.

5. Four Life Hacks From The Ultimate Online Community. On the life-changing magic of sending cold emails, being “bad,” and more.

6. Don’t Defer Happiness to a Future State You May Never Achieve. On the power of changing “one day” to “day one.”

7. Be Confident Enough To Let Go. On clearing out what no longer serves you to make space for what does.

8. Come-to-Jesus Moments. On how taking breaks can trigger major life changes.

9. Stop Holding Yourself Back. On conquering your fear of “taking up space.”

10. Keep Climbing. On what I learned from failing to reach the top of my biggest professional mountain to date.

On Online Course & Workshop Creation

1. What Every Course Creator Needs (But Doesn’t Know to Ask For). On my 5-step framework to design effective and engaging courses.

2. How to Create Engaging Online Workshops. On my 5-step process to design and deliver effective workshops.

3. Make Course Sales & Marketing Less Hard & More Robust. On a startup principle that helps you with both.

4. Why Most Cohort-Based Courses Are Designed to Fail. On the business opportunity most course creators sleep on.

5. Why Course Creators With Small Audiences Build The Best Courses. On the opportunity to start small and then scale.

6. This One Exercise Will Help You Decide Which Course to Create. On using what lights you up to illuminate the path forward.

7. Create Career Assets. On what solopreneurship taught me about scaling and avoiding burnout.

8. Three Valuable Resources to Structure Business Models & Ideas. On my biggest takeaways from working at a startup hub.

On Writing & Editing

1. Why Most Writing Falls Flat. On how to avoid boring people.

2. 7 Steps to Publish Weekly. On how to start writing consistently.

3. Embrace Being Bad. On a key lesson from 100 weeks of publishing.

As you read through my archive, feel free to add comments or drop me a note about anything that strikes you. I’ll still be checking my messages and notifications while my publishing is on pause. So I’d love to hear from you.

A Parting Reminder

As we settle into “cozy season,” I hope you remember this:

Thanks for reading and have a wonder-full autumn,

Alexandra

P.S. Happy Thanksgiving to my fellow Canadians. I hope you have a wonderful long weekend with family and friends against the backdrop of beautiful fall foliage.

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Today marks 150 weeks of publishing this newsletter.

A milestone that once seemed insanely out of reach.

But what started as a course assignment has fuelled my professional development over the past three years, each edition serving as a weekly reflection prompt and picture window to share my journey with you.

Despite how challenging it can be, I still feel like writing is something I get to do.

A huge part of my enjoyment stems from having a writing ritual I look forward to.

So in honour of my 150th anniversary, here’s why I encourage you to create a writing ritual—plus my tips on how to get started.

Why I Encourage You to Write Consistently

There are five reasons:

1. You will enhance your self-awareness

2. You will sharpen your thinking

3. You will boost your creativity

4. You will be more articulate

5. You will feel calmer

The last benefit—you will feel calmer—is the most underrated.

But by virtue of the other four, you’ll be less overwhelmed by jumbled thoughts.

Don’t just take my word for it though. There are plenty of successful people who describe writing as gasoline accelerating their careers.

Wes Kao’s Inspiring Example

co-founded Maven after co-founding the altMBA with legendary author and entrepreneur Seth Godin. I first came across Wes through Twitter back in 2021 when I forayed into the online course space.

Since then, one of my biggest career highlights has been working with Wes’ team on the Maven Course Accelerator.

It was an invaluable opportunity to learn from some of the best when it comes to marketing, communications, and teaching.

Wes’ newsletter recently crossed a whopping 50,000 subscribers and prolific teacher that she is, Wes took the opportunity to impart more wisdom:

If there’s one thing you take from Wes’ post, I hope it’s this:

“For years, I wrote to a small audience and had no social presence. I pretty much wrote into the void—and I’d do it all over again.”

Metrics That Matter

As someone who just crawled my way back to 500 subscribers three years and 150 editions into my weekly writing ritual (after cutting my list in January), I’m clearly not “metrics-driven” either.

I haven’t been deterred from drumming ahead with my writing by a lack of likes, comments, or shares.

The metrics that have mattered to me are:

1. How often am I publishing?

2. How much am I enjoying myself?

3. How much am I improving over time?

If, like me, you’re writing for yourself rather than a business, you decide what metrics matter. So don’t lose heart if you’re publishing into the void.

Now, before we get into how to create a writing ritual, there are two vital things to understand:

1. Forcing Functions

My biggest takeaway from Write of Passage, the online writing course and community I joined in Fall 2021, was from editor extraordinaire .

In two words amplified by alliteration, “The Dean” nailed a concept facilitators had been dancing around in description for weeks:

“Forcing functions.”

From day one of the course, there'd been a huge emphasis on the need to hit ‘Publish’ each week and project our latest article into cyberspace (a terrifying prospect for all of us new to “writing in public”).

Without a weekly deadline to “show our work,” it would be too easy to delay hitting ‘Publish’ indefinitely.

A common misconception about writing—and learning in general—is the more time you spend on one iteration of something, the better you’ll become at your craft. When in reality, beginners are better off doing multiple iterations in short succession.

If you drag out your first project by tinkering with different aspects, you end up wasting time on insignificant details because early on, you don’t have a good sense of how to edit.

By contrast, by focusing on robust repetition, your brain naturally starts spotting patterns. That’s where the magic unfolds. You develop an eye for what to stop doing versus what to double down on.

But you need a “forcing function” (i.e., a recurring deadline) to get those reps in.

Here’s a short parable to reinforce what I mean.

2. The Parable of The Pots

“The Parable of The Pots” is the story of a professor who wanted to identify the quickest route to progress. And so, he ran an experiment.

The professor divided his pottery class into two groups. Group A was instructed to produce one flower pot over several weeks and do their best to make it perfect. Group B was instructed to produce several pots in that same timeframe and work on getting better each time.

Now, pause for a moment.

Which group do you think produced the best pots by the end of the period? Really dig into why you think Group A or Group B.

Okay, ready for the grand reveal?

Drumroll…

In the end, Group B significantly outperformed Group A. Why? Because they practiced, got feedback, and iterated with each try.

With that in mind, here’s how you can start a weekly writing ritual.

How to Start & Sustain a Writing Ritual

A writing ritual must be in service of something.

And based on my 150 weeks of publishing, I can attest that “writing in public” is a phenomenal way to stay accountable, hone your skills, and attract like-minded people.

Hence I suggest you frame your writing as a “publishing practice.”

Here’s how to do that in two simple steps.

Step 1: Sort Out The Practical Stuff

Here are 10 tips to make your publishing practice a long-term success (so you can avoid quitting like most people):

1. Pick your “forcing function.” In other words, decide on your publishing frequency. My suggestion is weekly or barring that, every two weeks. If 1-2 week deadlines strike you as too short, then I challenge you to reduce your scope and aim for smaller outputs more frequently. The higher the output, the faster you’ll learn (think of The Parable of The Pots).

2. Pick your platform. I recommend Substack as it’s free, easy to use, and has a fantastic community of readers and writers.

3. Form an accountability pod with 3-4 writer friends. Writing groups of 4-5 people tend to be the sweet spot as they’re not “too crowded” and you avoid the risk of derailing your group if 1-2 people drop off. Ideally, you want to choose people who will commit to at least 1-3 months of supporting each other. The first few months are the hardest so you want people who are in your corner and vice versa.

4. Agree on which day to publish each week and commit to publishing at least 5 editions. It takes 30 days to cement behaviour change so give yourself a fair chance at making your ritual stick. Get everyone to commit to publishing on the same day to help you stay accountable. Oftentimes, people feel scared to hit ‘Publish’ when ironically, most people aren’t reading their stuff. By publishing together, you get a confidence boost and can even do fun New Year's-like countdowns to celebrate those early wins.

5. Pick 1-2 newsletters you want to emulate. Deciding on a format for your weekly posts can be daunting when you’re starting from a blank page. But no one’s expecting you to come up with a revolutionary format (especially out of the gate), so instead think about newsletters you want to channel. Start by trying to recreate them with your content. Keep experimenting until you find your style.

6. Commit to writing about a topic. Pick one focus area so you don’t get stuck overthinking what to write about each week. If you find it hard to stick with the topic, you’re free to pivot as you like. The important thing is to keep writing.

7. Schedule “sacred hours” to write and edit. Once you decide on your publishing cadence, you need to work backwards to figure out how you’ll honour it. That means carving out blocks in your schedule to get your writing and editing done. Initially, your writing and editing will be slow. But if you push through and keep publishing, you’ll speed up gradually over time. Within months and years, you’ll see huge leaps in efficiency.

8. Set aside 30-60 minutes for peer feedback pre-publishing. Figure out the best way to provide peer feedback. The simplest way is to partner people up or if you’re an odd number, assign each person someone’s work to edit. Use Google Docs to make comments on the structure by emphasizing what works and what could be better. I also recommend using the Write of Passage “CRIBS” framework where you pinpoint elements that are Confusing, Repetitive, Interesting, Boring, and Surprising. Elements that are Confusing, Repetitive, or Boring need to be fixed, whereas elements that are Interesting or Surprising are worth doubling down on. By providing feedback, you’ll develop a keener eye for editing your own work so I can’t emphasize the benefit of making time for this enough. You can also talk through sticking points if that’s easier and you have the time.

9. Engage with your pod members’ posts once published. Be each other’s biggest champions to keep going by liking and commenting on each other’s posts. This helps kickstart engagement and increases the likelihood of others doing the same for you.

10. Don’t make excuses. Aside from Tip 1 (Pick your “forcing function,” i.e., publishing frequency), this is the most important. Having a busy week, the disbandment of your accountability pod, or any other relatable reason for not hitting your weekly deadline is just that—relatable. But when it comes to commitment and having the discipline to hit your goal over and over again, week after week? Aim to be inspirational.

Step 2: Give Your Ritual a “Home”

With my 10 tips in mind, designate a space to get your writing done the same way you would step onto a yoga mat to begin a class.

Make the area as cozy and beautiful as possible.

My designated writing space is in my living room where I have big windows overlooking the nature beyond them and beautiful architecture (including a fireplace) that makes me reminiscent of living in Paris.

My go-to beverages to make my writing sessions extra cozy are coffee in the morning or early afternoon, and tea any other time of day.

The more inspiring your writing space is, the happier and more creative you’ll feel. So make your space somewhere you look forward to spending time.

Writing Benefits

“You can't connect the dots looking forward; you can only connect them looking backwards.”

—Steve Jobs

My writing delves into the personal more than the practical so it makes sense my readership is modest. Against conventional wisdom, I write what I’m compelled to write rather than beginning with my audience in mind.

But there’s a reason I write this way—a bunch of dots I hadn’t connected until I started writing my first book on September 8th.

Book Bonus

My book is about my first overseas move (to London in 2014) and my writing style is similar to how I’ve been sharing my journey in my newsletter.

That means all of my writing—over the past 150 weeks—has been in service of my book. I’ve been putting in the reps and building up the writing and editing muscles I’ll need to get my book across the ‘Publish’ line.

If that weren’t a big enough return on investment, I’ve also been fortunate to gain recognition from peers and role models.

Recognition From a Role Model

Last year, on November 3rd, my day was made by 7 am when I woke up to see my first “Substack Writers Shoutout” was from none other than Wes Kao.

I shared my gratitude in the post below:

Much like publishing 150 newsletters, having someone like Wes endorse my work from the top of the professional playing field felt insanely out of reach three years ago.

But I started writing anyway.

I’ve been publishing week after week in the name of growth and expansion, and I couldn’t be more grateful to myself and my readers for championing me along the way.

I especially want to thank my first five subscribers who’ve been reading since month one back in October 2021: , , , , and .

My writing has come a long way since then and your early support had a tremendous impact in propelling me forward. So, THANK YOU. Truly.

Here’s to the next 150 and seizing more of what feels insanely out of reach.

Have a wonder-full week,

Alexandra

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“Ross did not deserve Rachel!”

A friend of mine has been lamenting about this for as long as I’ve known him.

I usually shake my head and laugh at how 20 years since the finale, he’s still at war with FRIENDS.

Like most fans, I’ve never entertained the idea of Ross and Rachel not ending up together.

But this past Monday, I finally did.

I was tuned into an interview with Lainey Lui—a Canadian broadcaster whose fashion flair and sharp writing catapulted her from obscurity to the Oscars.

Lui writes a high-traffic blog, appears as a senior correspondent on Etalk—the leading Canadian entertainment news program, and previously co-hosted The Social—a Canadian daytime television talk show.

The woman knows how to craft good stories and according to her, Ross and Rachel’s long-awaited reunion went against a key writing principle.

Lui says “Good stories give people what they need, not necessarily what they want.” But she says most people struggle with this “because we all want to be liked.”

That doesn’t change the fact that:

“Good stories take hard turns.”

Using FRIENDS as an example, Lui described Ross and Rachel's reunion as a “fan service.”

Showwriters gave the fans what they wanted rather than the more realistic outcome of Miss Popular and Doctor Dinosaur not being suited for each other.

As Lui pointed out, “You don’t know what you need until you’ve sat there and processed it.”

She reasoned that 20 years after the series finale, people are more likely to entertain the thought that Ross and Rachel should not have ended up together.

But back in 2004?

Lui says, “People would’ve thrown me out of the building.”

Happy endings don’t always come down to getting what you want.

As many of us learn the hard way, sometimes what we thought we wanted doesn’t measure up to our expectations. Likewise, by loosening our grip on the future and being open to redirection, we often end up getting more than we’d hoped for.

Both scenarios require “hard turns” so it makes sense that great storytelling calls for a similar trajectory.

My Experience Writing About “Hard Turns”

I published my first online post in February 2021.

I wrote about my first career “failure” (getting rejected from law school) and how I reframed it as an opportunity to pursue my dream of moving to London.

I was nervous about posting my story for two reasons.

Firstly, I thought people would think less of me for failing to achieve a goal I’d set for myself, and secondly, I had never posted an article online and my writing was sorely out of practice.

So I asked several friends and family members to read my draft and offer feedback.

The unanimous piece of advice was to create a bigger gap between “everything going wrong” and “everything falling into place.”

My readers wanted to experience the “hard turn” rather than have me glaze over it.

After all, that’s where the story unfolds and the character is built, right?

Later that year, in October 2021, I rewrote the article with additional feedback from my writer peers.

I noticed a huge improvement and now that I’m rewriting it a third time as I incorporate it into my book, I’m working on expanding the hard turn even more.

Stay tuned for more updates.

In the meantime, here are six principles inspired by Lui’s interview on how to stay creatively fresh.

6 Principles to Stay Creatively Fresh

1. Don’t let numbers deter you

Lui’s story: 50-year-old Lui’s rise to the ranks of Oscar red carpet coverage began rather humbly when she started writing a fashion-focused newsletter to two girlfriends at 29.

Those two women forwarded her newsletter to more friends and her readership grew exponentially from there.

Within two years, Lui had amassed thousands of subscribers and a Canadian broadcasting company was eager to work with her. As a result, Lui launched her broadcast career at age 31 and she’s been a member of the elite entertainment scene ever since.

My story: I started writing my newsletter to a handful of subscribers at 31. Unlike Lui, my growth has been slow and has not led to any life-changing career offers.

However, writing weekly for the past three years has brought me a deep sense of joy and fulfillment. It’s simultaneously sharpened my thinking, enhanced my self-awareness, and boosted my creativity.

As you can see below, I just crawled my way back to 500 subscribers after cutting my list by 65% (roughly two-thirds) from 1,070 to 379 in January:

Despite having a small readership, I've met some incredible people through sharing my journey and deepened existing relationships with family and friends who've shared their stories in return.

2. Do things that improve your relationship with yourself

Lui’s story: Lui’s “sort of” memoir is called Listen to the Squawking Chicken: When Mother Knows Best, What's a Daughter To Do?

So naturally, the interviewer asked, “Has your book changed your relationship with your mother?”

Lui said “No, but it changed my relationship with myself and what’s possible for me.”

My story: I recently started working on my first book and I resonate with Lui’s assertion that it’s “so hard” but more importantly, that it’s changing my relationship with myself and what’s possible for me.

Things are only going up from here.

3. Crusade for your favourite art forms

Lui’s story: Lui says a big part of staying creatively fresh for her is resisting trends she doesn’t agree with. Take, for instance, the current 15-second fad.

“Everyone’s obsessed with small bites,” she says.

But as a self-described “long talker” who prefers “long-form journalism and long-form writing,” Lui says she’d rather crusade on behalf of longer stories.

While she admits some people can skillfully relay a story in 15 seconds, most people cannot. Not to mention, it reinforces micro-short attention spans which she regards as a disservice to all.

My story: I relate to Lui’s take. When it comes to writing platforms, I prefer Substack’s long-form content over Twitter’s short-form equivalent. Granted long-form writing attracts far fewer readers, I prefer the depth of experience for myself and my readers.

4. Start somewhere (even if that place “sucks”)

Lui’s story: Lui’s most valuable lesson in writing has been “You can’t fix nothing.” She explains that people get “bogged down by blank pages” because they want their draft to be good from the start.

But any writer can attest that great writing is born through rewriting, and to rewrite you need to start somewhere.

Lui’s advice is best illustrated by author Anne Lamott’s concept of “shitty first drafts” where you embrace your first draft as a messy starting point with the sole goal of getting something down so you can refine it.

It’s further supported by writer Julian Shapiro’s “Creativity Faucet” which is best explained in his own words, below:

Lui’s take on first drafts is “Something bad can be fixed” and “The start will always suck.”

Reflecting on her book-writing journey, Lui says everyone needs at least five drafts. Her book went through six or seven. The key is to “keep constructing and reconstructing.”

And bear in mind she writes 3,500 words a day.

Chances are those of us writing less will need even more drafts. So embrace the process. As Shapiro wrote of Mozart and Edison, nobody’s scoring you based on your input-to-output ratio.

My story: I wouldn’t be hitting 149 weeks of publishing today, let alone writing a book, if I hadn’t wholeheartedly embraced the messy first draft approach. It’s been three years and it hasn’t failed me yet.

5. Work with your friends

Lui’s story: Despite being told repeatedly, “Don’t work with your friends,” Lui shares the opposite advice with creatives.

“Group chats over comments,” she says.

Lui has friends she’s been writing with for 15 years, having not only exchanged feedback but contributed to each other’s sites in that time.

Her creativity is largely fueled by “being around people who are always going to ride for me.”

My story: My writing journey took flight when I found a community of writers to support me through the exchange of ideas and feedback. That community, as I’ve mentioned many times, was Write of Passage.

Their support was essential early on whereas nearly three years in, I tend to self-edit and send.

I know my writing would be better if I prioritized feedback but I don’t have the bandwidth to seek it out at present so instead, I simply ask for it when I’m stuck.

I can always count on my writer friends to get me moving again.

6. Take breaks as part of your creative process

Lui’s story: Lui recalled how it took her far too long to appreciate the importance of “taking breaks” to stay creatively fresh. She used to pride herself on being able to work the hardest and longest.

During peak periods—like awards season—she could run on as little as two hours of sleep and still crank out a blog or memorize a TV script.

But she’s since realized that creatives need to prioritize rest the same way athletes do. That means taking breaks, getting enough sleep, and generally having guardrails around how and what you do.

My story: I’m no stranger to burning myself out. In the past, I’ve let my obsession with work and creative projects (like writing) plow through every gate-like boundary leaving me exhausted amid the rubble. (I wrote more about this in a post called Burnout & The Paradox of Giving Up.)

But since then, I’ve learned the value of taking proper breaks. I don’t plan on burning out ever again and I’ve realized that by incorporating breaks into my routines, I wind up having more creative energy to write (hence finally starting my book).

Cheat Sheet For Creatives

To recap, here are 6 principles to stay creatively fresh:

1. Don’t let numbers deter you

2. Do things that improve your relationship with yourself

3. Crusade for your favourite art forms

4. Start somewhere (even if that place “sucks”)

5. Work with your friends

6. Take breaks as part of your creative process

I hope these principles inspire you to pursue your creative passion. You never know, it might be your ticket to the Oscars (or some other dreamy place).

Thanks for reading and have a wonder-full week,

Alexandra

P.S. I texted my friend after watching Lui’s interview to inform him a reputable broadcaster was in his camp on the Ross and Rachel matter. He sent back this meme (along with another assertion about how unrealistic the plot was):

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Growing up, we had a wood clock carved in the shape of Texas.

It hung in our basement, adjacent to the stone fireplace and above the TV. It wasn’t huge but it was hard to miss with its odd shape, glazed surface, and gold hands. I always noticed it, but I never thought about it.

Until last summer.

My mum’s oldest friend came to visit and we spent a few days at our cottage with our extended family. During dinner one night in the gazebo overlooking the lake, we got on the topic of Texas.

In the lead-up to graduation from nursing school, my mum, her friend, and several classmates had been recruited to fill a nursing shortage in Houston.

On top of jobs, they were offered help to find accommodation, plus flights and work visas.

It was a no-brainer for a bunch of nineteen-year-olds starting their careers.

So despite my grandmother’s pleas not to go, my mum and her friends said farewell to French Canada and howdy to the Lone Star State.

Texas Table Talk

For as long as I can remember, I’ve known my mum lived in Texas.

Over the years, she and my dad (who’d go visit) have shared the odd anecdote, like how crazy it was to rock up to places and see a bunch of shotguns strapped to the back of a pickup truck, or how their condo manager laughed and said “Oh bless your hearts, y’all have never seen a cockroach” when my mum and her friends screamed at the sight of one.

(Side note: Having lived in Australia, I can say with conviction that the upside to Canadian winters is far fewer creepy crawlers.)

With my mum’s friend at the dinner table, Texas memories poured out as vibrantly as the red wine swirling around our glasses as we laughed heartily from one story to the next.

It was cool to get a window into the lives of everyone who’d made it down South long before my siblings, cousins, and I entered the world.

It’s easy to forget our parents, grandparents, aunts, and uncles had lives pre-parenthood.

As an avid reader and writer, I often wish there was more captured from that time.

Writing a Book For Family

Back in January, a peer from the writing community I belong to shared this inspiring post:

“My neighbour wrote a 600 page book about his life, printed six copies for his family, and that's it.”

I salute Sir James. Anyone classy enough to produce a book of this quality and hand it out to six lucky people is top-tier.

Writing a Book For My Family

I was channelling Sir James when I began writing my book on Sunday, September 8th. I have zero expectations to make money from it (though that would be a huge bonus).

It’s just something I have to do.

Asked, “Who are you writing to?” I respond “My younger self.”

Barring that, it’d be the future children I hope to have.

I would love to give them an opportunity to peer into my past and how the people and places I encountered shaped the woman I am continuously evolving to be.

My hope is by understanding how I persevered in chasing a dream—and grew through the knockbacks I endured along the way—they’ll be empowered to chase their own.

Life Imitating Art (in a Ballet Studio)

My book is about pursuing my lifelong dream of moving to London in 2014, so I’d booked a solo slot at an English tea house to get started. I’d made the reservation for noon anticipating I’d be wiped from a fundraiser the previous day but I woke up at 7 am jazzed to get started.

Since I couldn’t change my reservation, I decided I would hit up a cafe nearby to start outlining.

So I hopped on the bus and over Mount Royal to the Mile End in search of coffee.

I found the closest cafe to the tea house where in a heartwarming life-imitating-art type of way I was confronted by my ideal audience—kids (in tutus no less).

I wound up at Les Impertinentes (The Impertinents), a hilariously fitting name for a cafe attached to a ballet studio with toddlers tantruming about.

There was a mix of people in the cafe, including a dad who was writing on his laptop while his baby played under the table delighting in the odd bout of peek-a-boo with patrons nearby.

His wife was presumably in the adult class we could see through the window overlooking the studio and it struck me what a nice ambiance the cafe created for families juggling fitness, hobbies, and childcare.

That’s not to say everyone was having a picture-perfect moment though.

For every family having a calm moment there was another reprimanding one kid for hitting their sibling or declaring the end a tantrum by announcing “That’s it! We’re going home.”

Later, when I settled in at the tea house to continue writing, I was touched to see that among the array of people there for the seasonal “strawberry social” service, there were several mother-daughter duos.

They had leaned into the “wear red or pink” dress code and an adorable young girl who beamed as she held the door for me had presumably made her way over from the ballet studio as she was wearing a tutu with her sparkly sequin jacket.

It made me excited about the possibility of doing fun stuff like that with my future kids and reinforced why I love to capture precious memories in writing.

Portals to The Past

Looking back, that wood clock shaped like Texas symbolized an important chapter in my parents’ lives.

My hope is my book on London will be a similar portal to the past—one that correlates with visits from old friends and heartfelt laughter at the dinner table.

Thanks for reading and have a wonder-full week,

Alexandra

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I was twenty-four and my one-way ticket from Montreal included two layovers—in Boston and Reykjavík—for the sake of stretching my savings:

In celebration of that life-changing leap that opened my world up in ways I hadn’t imagined, I decided to make the anniversary of one dream the inauguration of another.

I’ve been wanting to write a book about the story that unfolded from that first overseas move for years now.

I feel compelled to capture the life lessons I accrued from the people I encountered in veering from a conventional career path—in pursuit of something different.

In early June, I finally jotted down a rough project plan as a note on my phone to get started:

On Sunday, September 8th, 2024, I put my plan in motion. I sat down, started writing, and just like that (as Sarah Jessica Parker would say)… I turned “one day” into “day one.”

But finding the courage to finally start my book after dreaming about it for so long, let alone telling people I’m finally doing it, has been no easy feat.

Here’s why.

The Problem With Dreams

James Clear wrote the bible on employing “tiny changes” to achieve “remarkable results.” Thanks to his best-selling book, Atomic Habits, he’s now the modern day Godfather of how to achieve dreams through realistic means.

Here’s what Clear had to say about dreams in a recent newsletter:

I don’t know about you but when I’m eighty years old, I want to look back on my life and know “I went for it.”

My Dream Plan Versus The Next Best Thing

Before I jotted down a realistic plan to write my book, I had an unrealistic plan in mind. I had told myself that in honour of starting my book, I would fly to London and spend an enchanting visit retracing my steps from September 2014.

I would go to South Kensington to visit the Hyde Park-adjacent hostel where I wound up spending a month sleeping in bunkbeds in rooms of up to twelve people. (My original plan was to stay for two weeks maximum but alas, my search for housing proved awfully difficult. By the time I settled into my own room in a flatshare with three new friends, I felt like the bloody Queen.)

I’d imagined rocking up to our former apartment complex—Warwick Lodge—and being met with a rush of nostalgia.

I loved that about London. Every building had a designated title. A blend of structure with character.

It took me a while to introduce my home properly.

My inclination to say “War-wick Lodge” was immediately met with “It’s Warick Lodge. The second ‘w’ is silent.” Admittedly, the latter sounds better but how was I supposed to know?

As much as I delighted in the idea of a London reunion tour, it occurred to me earlier this year that my “plan” was purely romantic. Going back to London wasn’t feasible for September.

So rather than sulk and make excuses for why I needed to go there to write, I decided to reframe the situation. I thought “If I can’t go to London to channel my adventures from 2014 to 2016, how can I bring London to me?”

This brings me to my first intention in writing my book.

Best Practices From “Day One”

Intentions (i.e., What Went In)

I’m determined to make my book writing process as enjoyable as possible and not defer my happiness until publication. Two ways I plan to do that are:

1. Pick fun locales to write from

Sunday’s gem was the Cardinal Tea Room in honour of my inaugural book writing session coinciding with the tenth anniversary of my London move. As a bonus, my waitress was from the UK and we had a lovely chat about life in London versus Montreal (the most notable takeaway being Montreal is WAY more affordable).

2. Quit each session before I want to

I love writing and could easily let each session run for hours. But as legendary writer Seinfeld says, it’s best to have a hard stop. That way I finish feeling accomplished and eager to get back to it with clarity on my next steps.

Now on to what I learned from day one.

Learnings (i.e., What Came Out)

Overall, day one was amazing and I feel great about it. My mind was bursting with excitement and having poured my first 7,205 words into a Google Doc, here are several learnings I’m keen to share:

1. I’m further into writing this book than I realized. Ever since I started writing online in February 2021, I’ve been referencing aspects of my “London life.” So I have plenty of material to refine and expand on.

2. Thinking in chapters is key. I’ve started drafting my book by creating headers for each chapter (which I keep refining) so that they map to a table of contents at the top. This way I can drop bullet point references I want to include in their designated “spot” but still be able to “zoom out” and see the high-level structure. It’s a fun mapping exercise and I’m loving the puzzle aspect of moving chapters around to convey the sequential unfolding of events.

3. I’m floored by how much my writing has improved through consistent effort. I often remark on posts from the previous weeks thinking “I could’ve written this better” but the further back I go, the more extreme the sentiment. I’m aghast at how poorly written my oldest posts from three-and-a-half years ago are. An utter mess of thoughts broken up by boring explanations, all I can think now is how I would rewrite them 10x better. This book is my opportunity to do that.

   (Side note: If you’ve been reading my writing from the start, I appreciate you. Thank you for sticking with me through the muck.)

4. There are many random anecdotes I’ve preserved over the years without conscious effort. I’m realizing now there’s a reason they’ve stuck with me in vivid detail. They represent something novel or surprising that to this day, I’m inclined to share. 

Those are my top four takeaways from day one.

That and I haven’t felt this fired up about a project in a long time.

My only “challenge” Sunday was some back pain from a Dragon Boat cancer fundraiser I took part in on Saturday (that sport is hardcore). But for the most part, I was so pumped I barely noticed.

Documenting The Journey

“We do not learn from experience… we learn from reflecting on experience.” —John Dewey

Beyond reflecting on my learnings, I want to capture photos to commemorate my book-writing journey and the joy it brings me. That way I can remember where I was and how much fun I was having as I hopscotched to publication.

Here’s an overview of the photos I took above to commemorate day one:

1. I’ve loved reading and writing since I was a kid. So “The Schoolgirl with a Pearl Earring” mural I passed on Sunday morning gave me all the feels about pursuing my childhood dream of writing a book.

2. Drafting my book outline with strawberry tea and treats as part of Cardinal Tea Room’s “strawberry social” (Quebec strawberries are the best). I even followed their “wear red” dress code for the occasion. What’s cool is I’m able to draw on plenty of posts I’ve written in the past to create the best outline.

3. A closer look at Cardinal’s seasonal strawberry rooibos tea. They have the cutest cups, saucers, and teaspoons.

4. The adorable blue and red sign directing traffic to the tea house on Saint Laurent.

Reflection Time

“It's not the destination, it's the journey.” —Ralph Waldo Emerson

As Clear pointed out earlier, “Dreams are fun when they are distant.” I would argue the opposite can also be true.

Lately, I’ve been stunned by how many people overlook current sources of joy due to hyperfixation on future sources outside of their grasp.

Whether it’s wanting a promotion, a bigger home, another child, or anything else in between, it’s all too easy to fall into the trap of “I’ll be happier when I have X.”

Our minds can trick us into thinking that once we have the next thing, our life will be complete. Anything short of that vision becomes unacceptable and so we apply brute force to get that thing we want and feel we deserve.

But even then, it doesn’t work and we’re left feeling exhausted.

I’ve learned through my own wrestling with not getting everything I want on my timeline that the best pathway to being happiest in the future is to be happy with the present.

We have to trust the timing of our lives.

That means finding joy and gratitude in the process of working to achieve future states we yearn for. Because pursuing a dream can be remarkably un-fun—soul-destroying even—when we defer happiness to a future state we may never achieve.

Don’t let the future rob you of the present.

Question Time

Now’s as good a time as any to reflect on your latest dream. In James Clear-esque fashion, ask yourself:

From this point forward, am I going to be someone who thinks about it or goes for it?

I hope you pick the latter and drum up ways to enjoy the journey.

Thanks for reading and have a wonder-full week,

Alexandra

P.S. Saturday’s Dragon Boat fundraiser for Cedars CanSupport was a HUGE success (the rain even held out until we left). Together, Dialogue employees filled two boats (that’s 40 people) and exceeded our collective fundraising goal of $30K by $17K. Thank you SO much to everyone who donated in support of cancer patients and their families. I appreciate you.

P.P.S. Here’s another look at “The Schoolgirl with a Pearl Earring” mural in all its immensity. Here’s hoping you stroll past an equally apt representation of your dream that fires you up to run toward it.

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I was writing a friend’s birthday card last week when it occurred to me we’ve been friends for half our lives.

Seventeen years to be exact.

Granted that’s a significantly shorter duration than my oldest friendships stemming back to pre-school, it’s still pretty damn special.

Our seventeen-year bond stems back to my first move to Montreal, and a shared rite of passage as (budding) adults: Cegep (also known as pre-university college).

I’d just graduated high school, and like most teenagers from the Laurentians—the vast mountain range where I grew up—I’d had to move to “the city” to continue my schooling.

Up until then, I’d been a frequent visitor to Montreal (since like my friend, my parents are “from the city” and 90% of our extended family is here.)

When I think back to September 2007, I remember moving into my first apartment with my older sister and our two best friends from “up North.”

I have to laugh at how crazy it seemed to my city friend—and her parents—that we were living on our own.

It seems crazy to me now too. Seventeen seems so young.

But of course, at the time, I thought I was so mature and knew so much more about life than I did.

As you can imagine, the experience humbled me the way any major change and character-building transformation does. That first big move on the cusp of adulthood laid the soil for all the other milestones I’ve hit in the latter half of my thirty-four-year-old life.

The Significance of September

September has always been my “Go” month. Nothing ushers in a “new year” like new stationery and the joy of writing on pages as crisp as the fall breeze with pens as colourful as the turn of leaves.

There’s something sacred about the head, hand, and heart connection when you capture dreams, goals, and aspirations in ink.

It’s always seemed more sincere than popping bottles of champagne and counting down from ten in unison (despite how fun that can be).

I embrace New Year’s sparkly nature, but as a friend once told me, “I’m a September girl” at heart.

September has more substance. That’s precisely why I have a disproportionate amount of September milestones.

September Milestones (From Ages 17 to 34)

This September marks…

• Seventeen years since I moved to Montreal for Cegep at age seventeen (happy “Champagne birthday” to me).

• Ten years since I fulfilled my dream of moving to London.

• Seven years since I moved to Sydney after Australia kept beckoning.

• Six years since I moved to Paris on a whim when my Australian visa sponsorship fell through. (I moved back to Montreal two years later.)

• Three years since I quit my job to pursue my dream of self-employment.

• Three years since I started writing weekly because I felt compelled to share my journey.

• One year since I decided self-employment wasn’t working because despite all my efforts—and I gave it everything in me, believe me—I was lonely, lacking direction, and my finances were dwindling.

I’ve chased my dreams throughout the past seventeen years—the latter half of my life and the entirety of my adulthood.

The result of which is way too much hard-won wisdom to share in one post.

So I’ll limit today’s to two important gems.

Two Invaluable Gems of Wisdom From The Past 17 Years

1. Find what lights you up. You’ll be motivated to outperform.

Most of us know whether we belong in “T” or “F” territory in Myers–Briggs land. In other words, whether we tend to be led by our thoughts or our feelings. But regardless, everyone is ultimately led by their heart.

Attitude, effort, and hell, brute force, can only go so far when your heart isn’t in something.

Years ago, one of the best bosses and entrepreneurs I’ve ever worked for offered me advice I’ll never forget.

I was telling him about my dream of one day starting my own company and how my biggest barrier was coming up with the right idea.

The advice he gave me boils down to a simple formula:

Here’s a paraphrased elaboration on his equation:

What fires you up so much that you can’t not teach it and to some extent, you already do (even if you don’t regard yourself as a “teacher”)?

Think of the topics you bring up over and over again in conversations and seek out like-minded people to discuss.

What are you inclined to post about on social media, whether it’s sharing your thoughts or resources you find valuable?

You ultimately want to figure out what “lights you up” because running a business is hard but as long as you’re doing what you love, you’ll always have that extra bit of motivation to outperform those who don’t.

When work blends with play and you’re making use of your natural talents, you’ll know you’re fulfilling your mission in life.

I spent years overthinking business ideas before I finally took a run at self-employment in September 2021. Meanwhile, I had the answers within me.

Had I embraced my heart space over my head space to figure out what lights me up sooner, who knows what opportunities I could’ve seized?

2. Test your options, then commit to the best one. You’ll be wiser for it.

When I think about my September milestones, I’m all the more adamant that Bill Burnett and Dave Evans distill incredible life advice in their best-selling book on how to apply Design Thinking to “build a well-lived, joyful life.”

Building on the adage that often what we think we want isn’t what makes us happy and thus it’s important to try things on for size the way you would a clothing garment, Burnett and Evans propose you prototype and test before going all in on any one option in life.

In their book, Designing Your Life, the authors share stories from an array of professionals who “always thought” they would become one thing but wound up pivoting when that thing turned out to be unfulfilling.

When it comes to “life design,” prototyping involves simulating future circumstances so you can collect feedback that will inform your next steps. The goal is to take off whatever rose-tinted glasses you're looking at the horizon with.

That’s not to say there’s an inherent negativity in the process. But prototyping and testing are meant to ground you by dissolving any illusions you have about what a future state “will be like.”

For every September milestone I’ve listed, for every adventure that followed, I can name an array of painful knockbacks that made their way into the story. Numerous inflection points sent me soaring upward, while others sent me crashing down to the point where I questioned why I put myself in that situation.

But of course, leading up to each milestone, I was naive. Take my move to London, for example. In my head, it was going to be one massive upward swing. But the reality was more of a rollercoaster ride.

One minute I was living my best life at glamorous events like The British Fashion Awards, Royal Ascot, or having high-tea at Harrods. The next, I was living a nightmare dealing with a flooded apartment, struggling to make ends meet, and adapting to people constantly coming and going in a bustling city.

Day after day I had to push myself out of my comfort zone to meet new people and try new things. But those experiences were a catalyst for the woman I am today.

Had I never pursued my dream of living in London, I would’ve spent the next few decades deluding myself about how “perfect” it would’ve been, wondering how different my life might be had I worked up the courage to go.

Thankfully, I made it happen. I put my dream to the “test” and despite some incredibly challenging moments, the highs massively outweighed the lows.

I met people from all over the world. I visited historical landmarks like Stonehenge. And most importantly, I learned how to rely on myself, and to ask others for guidance along the way. 

In the end, I stayed in London for a second year, and my experience gave me the confidence to pursue subsequent dreams of moving to Sydney and Paris, before resettling in Montreal.

Now, having “prototyped and tested” life as a Londoner, Parisian, and Sydneysider, I know that while each city made a fantastic home at different stages in my life, my ultimate home is Montreal.

And now I have the opportunity to integrate what I’ve learned and the friendships I’ve developed in each place into my life in Canada, making it all the richer.

Something to think about

I have a disproportionate amount of September milestones. I’m convinced it’s because September has more substance than January in propelling people toward their dreams.

For those of us in the Northern Hemisphere, I imagine it has to do with “starting a new grade” year after year around this time. From early childhood (I mentioned pre-school earlier), we associate September with levelling up.

I clearly never lost that momentum.

I hope you haven’t either.

Thanks for reading and have a wonder-full week,

Alexandra

P.S. I have a September 2024 game plan to make another dream come true. Stay tuned for updates.

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In today’s post, I share four life hacks guaranteed to brighten your future (inspired by Write of Passage—the ultimate online community):

1. Send cold emails.

2. Embrace being bad.

3. Avoid regrets.

4. Keep putting yourself out there.

 ☕️ Read time: 7 mins (best with tea or coffee)

Last week, I was gutted to hear Write of Passage—the elite online writing course and community I’ve been part of for the past three years—is ending. Founder and writing advocate extraordinaire, David Perell, announced the news on Monday.

Write of Passage was life-changing for me.

Full stop.

I first joined in September 2021 and it unleashed the writer in me that was dying to get out. Three years later, I’m still writing strong.

It’s not just my archive of 144 posts I’m proud of, or the fact that I found the courage to hit ‘Send’ 144 times—even on days when I felt like I couldn’t or shouldn’t because I didn’t think what I’d written was any good.

I’m proud of the countless hours I’ve spent writing, rewriting, and hell, thinking about writing. Putting in the reps is where the magic happened—bit by bit, then in longer strides.

When I reflect on my Write of Passage journey over the past 36 months, I have too many gems of wisdom to share in one post.

So I’ll limit today’s to four:

1. Send cold emails. They will change your life.

In the lead-up to my first Write of Passage cohort, I wasn’t planning to join the course. Despite my keenness to get involved and unleash my inner writer, I’d just forked out USD 11K on remote studies to facilitate a career change.

So I emailed the team to inquire about future dates. To my surprise, founder David Perell got back to me with an alternative:

I was in awe of Perell’s response.

Now, three years later, I marvel at how my Write of Passage trajectory traces back to a cold email I sent in August 2021 thinking “Best case scenario someone might send me dates.”

That first cohort was life-changing.

I slept terribly for the five-week duration of it. My mind was firing like never before. The sheer amount of ideas and learnings sparked by two hundred interesting people coming together to enhance how we think and communicate was something I’d never experienced before.

I published all five weekly assignments and joined mentor sessions on weekends (shoutout to and for leading two of my favourites). I had dozens of writing-related conversations with peers from across the globe. And finally, I launched my Substack to continue writing while building a list of dedicated readers.

Since then, I’ve been fortunate to join subsequent cohorts as a mentor and editor. Both helped me grow tremendously. (I wrote more about this in a popular post called Why Most Writing Falls Flat (& How to Avoid Boring People)).

Now, granted not every cold email results in a life-changing opportunity, you’re bound to miss out if you don’t give them a try.

When I was in university, I used to send cold emails regularly. That’s how I landed my first internship and my first post-university job. It’s also how I found mentors to ask for career advice.

Sure, some messages went unacknowledged, which was a bummer given I’d spent significant time crafting them (having researched my recipients thoroughly). But a surprising amount responded warmly and when they couldn’t help me directly, they’d refer me to someone who could.

Another brilliant case for why you should send cold messages is my story of how sending “a cold one” via LinkedIn resulted in my landing a dream job in Paris. (I wrote more about this in a previous post called Main Character Energy.)

As a learning junkie always trying to level up, I’ve devoured countless articles on “how to write a good cold email” since I was a teenager. I can distill the best advice in four points:

• Have a clear call to action

• Air on the side of professionalism

• Emphasize what’s in it for the recipient

• Be genuine, concise, and conversational

Whether it was landing my first internship or post-university job, securing a scholarship for Write of Passage or hell, getting my dream job in Paris, cold messages have changed my life.

So please send cold emails. They will change your life too.

2. Embrace being bad. It’s the only way to get good.

One of the most powerful Write of Passage teachings is what they call the “taste gap.” Here’s an overview from Perell on what that is:

The Write of Passage course curriculum is a turbojet designed to help “close the gap.”

My initial writing wasn’t anywhere near my taste in reading. But at the same time, I didn’t realize how bland my writing was. As I began reading other students’ work and providing feedback, I began holding up a mirror to myself.

I applied what I learnt and saw my work getting better. That cycle repeated itself cohort after cohort and in between as I continued reading the work of my Write of Passage peers. I would often find myself alternating between “Oh, that’s a brilliant structure, flow, or wordplay” and “They could have made X even better had they done Y or Z.”

I see a marked improvement in my work from year one to three. And yet I often still cringe at what I write from one week to the next. I’ll spot a typo after hitting ‘Send’ or think “Eugh, I could’ve been more concise, more creative, or more clear.”

Some weeks I feel like I’m on fire (in a good way) and other times I’m engulfed by my own confusion about what the hell I’m trying to say. And I wonder, “Why on earth would anyone read my writing?”

Then I have to remind myself that it’s all part of reaching my potential.

I urge you to give yourself the same grace. Embrace the taste gap. It’s the only way to get good.

3. Avoid regrets. Do creative work you feel compelled to do.

In November 2021, I met Perell in Montreal shortly after my first Write of Passage cohort. I remember it as vividly as the neon pink soap we were forced to wash our hands with upon entering a favourite restaurant of mine.

Quebec had instituted a “vaccine passport” system as part of COVID-19 prevention measures so on top of giving Perell a heads up to bring proof of vaccination, the restaurant—which I explained was originally called “Darling” but had since been renamed “Le Darling” to appease Quebec’s language police—had leaned into the hand washing requirement by setting up a funky industrial-size sink with an industrial-size condiment dispenser full of neon pink soap.

The insight I remember most from my conversation with Perell was this: when he asked me why I started writing online, I felt like I didn’t have a good answer. All I could offer was “I just felt compelled to start writing.”

Afterwards, all I could think was “What a dumb response.”

But since then, I’ve come to appreciate that sometimes our intuition can sense things before we can make sense of them. So if you’re compelled to do creative work, go for it. You don’t need a “why” beyond that.

Take it from American Poet Mary Oliver who offered this cautionary insight:

Avoid regrets. Do creative work you feel compelled to do—even if it’s just for the hell of it.

4. Keep putting yourself out there. You never know who’s watching.

Reflecting on Perell’s response to my cold email, I can’t help but marvel at how “I’ve seen you around Twitter” factored into a scholarship.

I joined Twitter in early 2021 on the recommendation of a professor who said “That’s where all the Instructional Designers hang out.” I didn’t know anyone on the platform—let alone for professional development purposes—so I was mostly overwhelmed with where to start.

Eventually, I stumbled upon a writing challenge called Ship 30 for 30. It seemed like a fun community and that’s how I kickstarted my Twitter journey. From there, I began jumping into short, forum-like discussions. But I barely had any followers and didn’t think anyone was particularly interested in what I had to share.

So it was wild to me that someone like Perell, who has hundreds of thousands of followers, recognized my name from our limited interactions—namely, me commenting on his posts.

Since then, I’ve had more opportunities to collaborate with incredible creators and startups. Whether it was someone who’d seen a Twitter or LinkedIn post of mine, stumbled across my Substack, or watched one of my YouTube tutorials, I’ve seen the benefits of sharing resources on the Internet.

Turns out there are more people admiring our work than we think.

So bear that in mind. Keep putting yourself out there and sharing your work.

You never know who’s admiring you from afar and what door they’re willing to open. Wouldn’t it be cool to find out?

Life hack cheat sheet

To recap, here are four Write of Passage-inspired life hacks guaranteed to brighten your future:

1. Send cold emails. They will change your life.

2. Embrace being bad. It’s the only way to get good.

3. Avoid regrets. Do creative work you feel compelled to do.

4. Keep putting yourself out there. You never know who’s watching.

My challenge to you is to pick one you can implement today.

Thanks for reading and have a wonder-full week,

Alexandra

P.S. Thank you to everyone at Write of Passage and within the community for making it so special. As I mentioned, there are way too many gems of wisdom to share in one post so I look forward to sharing more in the future. In the meantime, I also want to give a MASSIVE shoutout to Perell’s co-founder, . Thank you for everything. The two of you built something incredible that will continue to inspire people for decades to come.

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In today’s post, I share wisdom from:

• Country singer Sam Hunt

• The entrepreneur behind Product Hunt

• My firsthand experience relating to both

 ☕️ Read time: 3 mins (best with tea or coffee)

“Less monologuing, more singing!” a friend joked as she swirled her drink. A bunch of us were crowded into Parc Jean-Drapeau watching Sam Hunt headline Lasso—Montreal’s first country festival now in its third year of business.

While I also prefer quicker transitions between songs, hearing Hunt introduce ‘Start Nowhere’ struck a different chord with me.

The song is an “age-old story where a young man leaves his home to see the world, only to come back and appreciate where he’s from even more.”

According to his “monologue,” the song illustrates how the 39-year-old left his small town in Georgia at 18 to attend university in Tennessee and Alabama before moving to Nashville to skyrocket his music career, in 2008.

As Hunt described his need to leave home and explore the world as a young adult, I started thinking about a similar need I had in my early twenties.

Leaving Home

A lot of us can relate to needing a change of scenery as a young adult, particularly as a new grad asking ourselves, “What now?”

Last week, I read a great post on this topic called “Why you should move” by Ryan Hoover, the American tech entrepreneur behind Product Hunt—a wildly successful platform to launch and discover new products. In it, Hoover shared how moving to San Francisco in 2010 was “one of the best decisions” he’s made (in what most people would consider a remarkable career).

Here’s his explanation as to why:

London was my San Francisco (granted with lousier weather).

I’d had an inexplicable affinity for the city ever since I was a kid and when I finally visited on a backpacking trip at age 20, I understood why. The rich history, creative genius, and big red buses cruising past pristine Parliament buildings?

I was in heaven.

I only spent four days in London during that initial visit in July 2010 but it sparked an “aliveness” in me that I’d never felt before. I’d never been so intellectually stimulated.

It was organized chaos as droves of people made their way through winding lanes and cobblestone streets to pubs, fashion houses, financial offices, and everything in between. Everyone walked fast, confident in their direction.

But more than anything, it was the diversity of people and minds that inspired me to dream BIGGER—as though London were a whole new world of its own.

I swore to my friends that I’d move there someday.

I began to feel how Hoover felt in his hometown—like I didn’t belong in Montreal. Despite having the best family and childhood friends, I was largely bored and uninspired throughout university.

I had to go somewhere new and exciting.

So after a year of working and saving post-graduation, I finally did. On September 8th, 2014, I boarded a one-way flight to London.

I kept my plans under wraps until the last minute determined not to be dissuaded by people poking holes in them. It seemed the universe was on my side because I had to visit the British consulate in Ottawa to get my biometrics taken for my visa application, and my sister was coincidentally running the Ottawa half-marathon around that time. So I was able to subtly squeeze in my appointment on that same trip I’d joined as a spectator.

When I got my visa a few weeks later, my aunt and uncle—who double as my godparents—were the first family members I told. As lifelong globetrotters and avid readers who appreciate good intellect, I knew they’d be thrilled for me.

It’s crazy to think it’s now been ten years since I whispered my news to them on a crowded terrace during a fundraiser in memory of my late cousin (something I know would make him smile as he was the King of YOLO and loved being in on secrets).

A couple of days later, I spilled my English “tea” to the rest of the family at our cottage. It took multiple conversations—on the patio over morning coffees, on the dock in the afternoon, and in the kitchen in between—but I heaved a sigh of relief once everyone was in the know.

My departure was imminent so some people were emotional with their goodbyes. Others generated comic relief, like a cousin whose parting words were “See ya on the Internet!”

I share this because if you’re considering making a move, it can be hard to muster the confidence to go—especially early on when you’re exploring your options. People tend to project their fears and self-limitations when offering advice (we’ve all been guilty of it, even if we didn’t realize it at the time).

My advice is to think of waiting to tell others your news as putting on noise-cancelling headphones while you’re doing important work. Some people might feel blindsided, but you have to do what’s best for you.

Coming Home

By the time I hit my one-year anniversary in London, I thought I’d never leave. But I did. First for Sydney, then Paris, and eventually my home of all homes... Montreal. When I think about my full-circle journey, I think of Terry Pratchett’s words:

“Why do you go away? So that you can come back. So that you can see the place you came from with new eyes and extra colors.”

Hoover hasn’t moved back to his hometown but he clearly has a deep appreciation for where he’s from and how leaving changed his perspective on life. As for Hunt, he credits “finding his way home” and “reconnecting with his roots” with shaping the man he is today.

As for me, in the wake of my ten-year London anniversary, my advice is this: whether you're itching to move somewhere short-term or long-term, DO IT. Yes, it will be hard. But it will change you. And that's a return on investment that will continue compounding for the rest of your life.

Thanks for reading and have a wonder-full week,

Alexandra

P.S. On September 7th, I’ll be hitting the water with my Dialogue colleagues for the Cedars CanSupport Dragon Boat Race to support Cancer patients and their families, and I’d appreciate your support.

I first participated in the event back in 2016 following a tour of Cedars Cancer Centre where I was brought to tears hearing patients and physicians describe the value of the Centre’s complementary support alongside conventional treatment.

The event itself was equally inspiring and tons of fun with participants (myself included) bringing family and friends along to rally for a great cause.

Each year there’s a “Flower Ceremony” where races are paused, music is played, and people place flowers in the water to commemorate all the wonderful people we've lost to Cancer and hold deep within our hearts.

Please help me help others by donating to this wonderful cause. Any amount is appreciated. Thank you so much.

P.P.S. Here’s a glance at last night’s team practice (which culminated in a race in the rain):

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Today, I share how you can facilitate your happiest future using a vacation “litmus test” inspired by:

• A quote from a novelist

• A concept from an entrepreneur

• A question I’ve been asking myself for years

 ☕️ Read time: 3 mins (best with tea or coffee)

American novelist Hanya Yanagihara once wrote, “The best part about going away is coming home.” I inevitably think about this quote anytime I go on vacation. I use it as a frame to reflect on whether I’m truly happy or just comfortable with how things are. In the latter case, I identify things I need to change.

I urge others to do the same when they confide in me that they dread going “back to reality” or view vacation as an “escape.” Granted vacations are an opportunity to scale back on everyday responsibilities and indulge in a euphoric state of being, if time away becomes a lifeline to keep your daily life afloat, that’s a surefire sign that you need to make changes.

Asking myself, “Am I ready and looking forward to going home?” at the end of a trip has served me well over the years and across the four countries I’ve lived in.

Most of the time, I’ve been pleased to answer my question with an emphatic “Yes.” That’s not to say I wouldn’t have enjoyed prolonged vacations but even in cases where I wasn’t necessarily looking forward to getting back to work, my excitement about seeing cherished colleagues and filling them in on my adventures, would prime me to get back into the flow.

Most recently, I’m happy to report that after two weeks in Italy on a dream family vacation in celebration of my brother’s wedding, I was ready and looking forward to coming home last weekend. I returned feeling grateful, rejuvenated, and creatively inspired.

Conversely, I remember one time many years ago when I took a two-week vacation abroad and by the end, realized I wasn’t looking forward to going back to work. For the first time in my life, it occurred to me that I wasn’t even looking forward to seeing my colleagues.

Despite being great people whose company I enjoyed (no pun intended), my time away made me realize the extent to which the office culture had shifted. The atmosphere had become tense and frigid. It prompted me to speak up upon my return and while things didn’t change overnight, they improved over time.

Another major change sparked by the same litmus test was when I quit my job to pursue self-employment precisely three years ago, in August 2021. I had just returned to work from a two-week vacation in Miami. I expected my bosses to be shocked—pissed off, even—that I was quitting days after my return. Surely they’d think, “Why didn’t you tell us beforehand to give us extra notice?” But to my surprise, it was quite the opposite.

I’ll always remember what one Director—a veteran entrepreneur—said to soothe my guilt:

“Don’t feel bad. It’s normal to have these “come-to-Jesus” moments when you take a break and remove yourself from your typical environment.”

A come-to-Jesus moment is “a moment of sudden realization, comprehension, or recognition that often precipitates a major change.” These moments can be sparked by a reaction to Yanagihara’s claim that “The best part about going away is coming home.” My question to you is, how do you feel about “coming home” after time away?

How much time you take can dramatically alter your revelations. Two weeks is my sweet spot to disconnect and relax while creating enough distance to deeply reflect on what I want moving forward. But the amount of time you need will vary so trust your instincts. Regardless, it helps to visit a beautiful place. My time in Italy has me extra optimistic about running toward my dreams for the future—and to face any fears that crop up in my quest.

I urge you to do the same. Identify anything within your life that needs changing and make those changes. As I shared in a previous post called Let Go (to Live The Life You Were Born to Live), most people prefer familiar pain over fear of the unknown. But you only get one life, so strive for maximum happiness. You deserve it.

Here’s hoping you get everything you dream of.

Thanks for reading and have a wonder-full week,

Alexandra

If you’re not a subscriber, here’s what you missed recently:

• Let Go

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Today, I share the following wisdom from therapy and Pretty Woman:

• An empowering four-word phrase

• How to “simmer” to avoid “boiling over”

• Why you must be your own advocate at work and in healthcare

 ☕️ Read time: 5 mins (best with tea or coffee)

This time last summer I went looking for a therapist. I was burnt out and anxious at the helm of self-employment, and I needed help navigating what to do next.

Despite the stodgy male personas I’d seen portrayed on TV, I struck gold with a warmer, stylish woman not much older than myself.

Speaking to her is like a heart-to-heart with an extremely grounded, practical friend, and at the end of each session, she bids me adieu with four simple yet powerful words:

There’s only one other person I’ve heard use this phrase in lieu of the grammatically correct “Take care of yourself.”

The best part? Said individual is a fictional character and street-walking icon from a 1990 rom-com that remains one of the biggest blockbusters of all time—Pretty Woman.

Kit De Luca, Julia Roberts’ feisty, flaky, but ultimately caring roommate in Pretty Woman is consistent and concise with her sendoffs.

Whether Roberts’ character Vivian is headed out to entertain a client or putting her old life behind her to begin anew, De Luca offers the same judgment-free advice:

“Take care of you.”

In the past year of hearing my therapist say those same four words, I’ve come to appreciate them even more.

Today, I’m sharing two major ways I’ve internalized them (in hopes you do too).

1. Keep the pot at a simmer

In my first month of therapy, I met with my therapist on a weekly basis given I was anxious, burnt out, and torn between whether to stick with self-employment or revert to a nine-to-five lifestyle.

But as I got clarity on what I wanted, I dropped my cadence to bi-weekly in month two, and then monthly for months three and four. Eventually, I stopped going once I started my new job.

I was feeling back to myself and no longer anxious or burnt out, plus in order to make an appointment, I’d have to miss work which unfortunately doesn’t bode well with new jobs.

But then, after a few months, I had to book an unrelated appointment and figured, why not take a half day so I could also see my therapist and reflect on the past few months?

So I did and it felt great to take stock of my progress and improved well-being. From there, I decided to embrace a “pot simmering” analogy in which I would meet with my therapist every four to six weeks to check in, even if I didn’t “need” to.

We both agreed it was a great way to avoid a scenario in which “the pot boils over” and I wind up feeling burnt out or anxious again.

So now, when someone who has never seen a therapist asks me why I would spend the time and money continuing with therapy when I “seem fine,” I have my answer.

2. Be your own advocate

One of my biggest takeaways from self-employment has been to “be your own advocate” and that applies as much in the workplace as it does in the healthcare system.

In early May, I started having abdominal pain linked to a foot injury that initially seemed to get better with osteotreatment, but then got significantly worse in June.

Initially, I was plagued by fear and guilt for requesting flexible work hours to attend weekly treatment sessions.

But in hindsight, that was a waste of energy given my work wasn’t impacted and my employer is a healthcare company with “care” as a core value. It wasn’t a problem.

Nonetheless, I had to repeat these four words like a mantra this past week as I prepared for a trip to Italy on Saturday for my brother’s wedding:

My ongoing pain culminated in several appointments to see my osteo, meet with a podiatrist, get fitted for orthotics (hello, geriatric era), and then finally see my GP for peace of mind that I was fit to travel.

But while I’d anticipated my GP waving the white flag, I had a major “Oh shit” moment when my GP said she wasn’t convinced my abdominal pain was linked to my foot injury and to be safe, she wanted to send me for more tests to rule out other causes.

I tried not to worry but I was slightly panicked at the thought of finding another culprit. While there’s never a “good time” to have health issues, a week before I’m due to be a bridesmaid in Italy is undoubtedly one of the worst.

By some miracle given the state of Quebec’s healthcare system, I managed to get my tests done the very next day. Initially, the hospital wanted to give me an appointment the following Friday—the day before I left—but that would mean boarding my transatlantic flight before getting my results.

Thankfully, I advocated for myself on the phone and told them I would wait all day if they could squeeze me in that same day and sure enough they told me to come right over.

On top of that, the administrative staff was so empathetic about my forthcoming departure that they assured me they would get me in as soon as possible.

I still ended up waiting a couple of hours and as I looked around the waiting room I saw people of all demographics waiting on appointments of all different sorts—some nervous and pacing, others dozing or scrolling (I, myself, alternating between calmly reading and fending off anxious thoughts).

It was a profound reminder that our health is a gift and there’s nothing like sickness or injury to make you appreciate that—plus all the incredible people who keep our healthcare system running.

So again, despite initially feeling “bad” and worrying about how it might “look” to miss another half-day of work in proximity to my two-week vacation, I was proud of myself for putting my health first. Plus I was on top of my work, entitled to the time off, and communicating my whereabouts to my manager so there was no reason to waste energy questioning how I might be perceived.

I used to think killing yourself for a job you care about was a sign of passion and dedication. But after my own experience with burnout, I now recognize how foolish that is. There’s no prize in the world big enough to compensate for poor health.

The great news—miraculous, if you will—is my tests came back clean and I’m all clear to travel (alas my foot injury is the culprit of my pain and hopefully the orthotics will relieve it).

But my takeaway to “be your own advocate” stands, whether that means overriding remarks from friends, family, coworkers, or anyone else questioning your actions or course of treatment.

Before seeing my GP, a friend had said to me “Why bother seeing your GP if the podiatrist gave you orthotics to fix the problem?” I told her “Peace of mind” since podiatrists don’t examine you completely.

I’m extremely grateful that as a Canadian, I was able to see a GP and get hospital tests the very next day by flashing a Medicare card in lieu of payment. It would’ve been negligent to waste that privilege.

Had I not bothered to get checked out and there had been another culprit left unattended, who knows how much worse off I’d be? Blaming “so-and-so” for telling me to cancel wouldn’t do any good at that point, would it?

As an adult, you are responsible for your health and well-being and that’s the most important job you’ll ever have. Everything stems from there.

So as my therapist and Kit De Luca would say…

Take care of you.

Thanks for reading and have a wonder-full summer,

Alexandra

P.S. Last week I declared I was hitting ‘Pause’ on my posts but since today is International Self-Care Day, I felt compelled to share my newfound therapy-meets-Pretty Woman wisdom. Now I’m really signing off. So once again… arrivederci.

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Today, I’m sharing what my first tour of Europe taught me about:

• Reframing “all or nothing”

• Embracing my independence

• Laying foundations for the future

 ☕️ Read time: 3 mins (best with tea or coffee)

I land in Italy ten days from today and I feel both excited and nostalgic.

I haven’t been to Rome since 2010, a whopping fourteen years ago—but it was the first place in Europe I ever visited.

And what I learned through how I got there is something I'll never forget.

I was a twenty-year-old university student and part-time café worker meeting three friends at the halfway point of their nine-week “Euro Trip.”

But originally, I didn’t think I could go at all.

The way I saw it was even on a backpacker budget of bunkbeds and breakfasts in grungy hostel kitchens, I couldn’t swing nine weeks away.

I told my aunt as much as I deflated on her couch.

The words she spoke next will stay with me forever:

“Why don’t you meet them?”

I perked up like a helium balloon destined for the sky.

It hadn’t occurred to me that it wasn’t an all-or-nothing proposition.

So we pulled up my friends’ itinerary and decided I would meet them in Rome.

Fast forward a month, and after touching down on Italian soil, I was hopping on a train to the capital’s city centre.

When I think back to that trip, it was both an end and a beginning.

The end of seeing things as all or nothing—and the beginning of embracing my independence.

I was as nervous as I was excited about landing in a foreign country and boarding a train by myself.

(Remember, this was before WiFi and roaming services were common and we relied on paying for computer time at hostels to assure our parents we were still alive.)

My friends waved from the platform like a finisher flag on my solo journey as my train glided into the station.

I'd made it.

But that was merely the start of a new chapter in my life.

The adventures that followed laid the foundations for a fourteen-year future that traversed the globe in ways I hadn’t yet dreamt of.

After Italy, we spent the bulk of our time in the Greek Islands—where we returned the following summer to work after meeting so many people our age.

Then we went to London—a place I'd always known I wanted to live and wound up moving to four years later (you can read that story here).

Finally, we wrapped up with a visit to Ireland—where five years later, I toured my siblings around when they came to visit me in London.

Most people count themselves lucky to visit the Cliffs of Moher once in their lifetime. So I guess I’m doing my Irish heritage proud having been lucky enough to visit them twice already.

One of my friends and I’s favourite anecdotes from over a decade’s worth of travel together is from the first time we visited the Cliffs.

As we were strolling through the greenest grass you’ve ever seen, navigating the winding path along Ireland’s coast, a woman ahead of us kept nervously telling her daughter—who kept straying from the path—to back up.

But the only person who ended up in danger was the dad, when he said jovially to his wife “What are you so worried about? We’ve got two spares.”

My friends and I had to stifle our laughter as the mom reacted as well as you’d imagine.

Later, when we recounted the story to my friend’s mom anticipating a laugh, she said grimly “That’s not funny.”

Alas, perhaps you had to be there?

Another favourite anecdote is from Rome. More specifically, the first time my friends and I roamed the Colosseum (sorry, couldn’t help myself).

We were taking photos on actual cameras because it was 2010 (in other words, archaic) when a guy from the group next to us called out “Sky right” and everyone in his party gazed up into the distance for a majestic shot.

It’s been fourteen years and my friends and I still call out “Sky right” and laugh when we’re assembling for a photo.

Now fast forward to this summer, and my entire family is headed to Italy for my brother's wedding.

We're making a big trip out of it, and I've been happy to take the lead on building our itinerary.

It's been a fun opportunity to combine what I've learned from my years overseas, extensive European travel, and past work experience in event planning and executive assistance into a dream vacation for my family.

One that will accommodate everyone from toddlers to seniors—which thankfully, Italy is one of the best countries for given multigenerational households are common and there's a beautiful emphasis on family gatherings.

I realize now that my aunt getting me to Rome a whopping fourteen summers ago was instrumental in my travel and overseas moves to London, Sydney, and Paris that followed.

I had a full-circle moment last Friday when it hit me that by organizing my family’s trip, I’m now playing an instrumental role in my niece’s first visit to Rome (granted she’s three and won’t remember it).

I had another full circle moment when it occurred to me that my initial Rome visit consisted of a detailed itinerary my friends and I made pre-departure. But in the years that followed, I was way more spontaneous in travelling around Europe given I did shorter trips more frequently from London and WiFi was more common.

But now, taking into account we're a much bigger group with toddlers and seniors in tow for a much longer trip, I'm back to that spreadsheet life. Thus my not-so-wild Friday night involved sending a family-wide email beginning as follows:

Most importantly, I'm keeping in mind that our trip isn't “all-or-nothing.”

So rather than overloading our itinerary as I would’ve been prone to in the past, we’re prioritizing the key things and allowing for plenty of time to relax and enjoy time together as a family.

I hope you do the same with yours.

Happy summer holidays,

Alexandra

P.S. I’m hitting ‘Pause’ on my posts for a few weeks to embody European summer vibes and the art of slow living. So arrivederci… (until August).