Every time I am back in the city, I make the reservation. I have done it through moves and jobs and breakups and entire reinventions of my life. Same table, if I can get it. Same order, more or less. It has become a kind of pilgrimage — a thing I do not question, only repeat.

I always told myself I go for the food. That is not really true. I am not sure it was ever true.

What I have been going back for, if I am honest, is a person.

I started eating there in my early twenties, when I had almost nothing figured out and somehow felt wonderful about it anyway. I was broke and unsure and completely convinced that everything was ahead of me. I had a specific kind of hope back then — the uncomplicated kind, the kind you have before life has had a chance to disappoint you. Before the jobs that ended. Before the losses that rearranged you. Before the slow accumulation of scars that every adult is quietly carrying by the time they hit their forties.

That version of me used to sit at that table and dream. And for twenty years, I think I kept coming back to find her.

I would make the reservation and some part of me believed that if I sat in the right chair, in the right light, ordered the right thing, I could reach back through all of it and be her again. Carefree. Unscarred. Full of that easy, unearned optimism. I was not going for dinner. I was going to visit a ghost of myself, and half-hoping she would rub off on me.

This last time, something was different.

I sat down, looked around, and finally let myself see it. The food is not good. Honestly, it is a little sad. The service is indifferent. The room is worn in a way that is not charming, just old. The magic I keep driving across the city for is not in the building. It never was.

And my first feeling was loss. Because if even this place — my place, my anchor, my little time machine — does not hold the feeling anymore, then maybe she really is gone. Maybe you cannot go back.

But I sat there a while longer, and a different thought arrived. A quieter one.

I started thinking about what that young woman actually wanted — the life she was dreaming up over a plate of food she was too hopeful to notice was mediocre. The ambitions. The person she was so desperate to become.

And it landed on me slowly, the way the truest things do: she got there. I became her, and then I kept going. I’ve built things she wouldn’t have dared imagine. I’ve survived things she didn’t know were coming and came out the other side — still standing, still hopeful, just sturdier now, and more weathered.

I didn’t lose her. I delivered on her.

That’s why the restaurant doesn’t fit anymore. Not because I fell short of who I was — because I outgrew the place where she did her wishing. You can’t keep sitting at the table where you dreamed the dream after the dream has come true. The reaching is done. It worked.

So I can let it go now. Not the memory — the reaching. The quiet fear that the best version of me was behind me, in a chair, in a city, twenty years ago.

She was never behind me. She’s been here the whole time — grown up, scarred, accomplished, and, it turns out, completely okay.

I kept going back to find her. I didn’t realize I’d become the answer she was looking for.

P.S. If something here made you think, laugh, or feel a little less alone, you can buy me a coffee at buymeacoffee.com/whynotboth. Every cup goes toward more Tuesday mornings doing exactly this.

Not in a passing way. I got home that night and started hunting for it — the exact one. Not something like it, the precise thing. I sat there, a grown woman, searching at midnight for a jacket from a movie, certain that if I could just find it, something would click into place.

This is not new. I have been doing some version of this my whole life — leaving a movie, a party, a room, and quietly trying to reverse-engineer my way into becoming whoever just made it look so easy.

For the longest time, I’ve told myself this is because I love fashion.

It isn’t. What I wanted wasn’t the jacket. It was her — the ease, the certainty, the way a woman like that seems to walk into every room already belonging. I wasn’t shopping for outerwear. I was trying to buy my way into a feeling.

Here’s what I’ve come to understand: almost nobody is actually buying the thing.

We’re buying what it promises. The candle isn’t a candle — it’s the calm, ordered home we’re sure we’d finally have if we just got our life together. The jacket isn’t a jacket. It’s the woman who wears it like she was born sure of herself. We reach for the object because it’s right there — and the feeling underneath it isn’t.

This isn’t a flaw in people. It’s just what wanting looks like.

And I know it intimately, because I’ve spent twenty years on the other side of it.

That’s my work. I build brands. Which means my actual job — the real one, underneath the campaigns and the launches — is to understand what people long for, and to speak to it. To listen for the feeling beneath the purchase and give it language.

I want to be honest about what that is, because it’s easy to make it sound cynical, and it isn’t. Done well, it’s one of the most intimate skills there is. You’re not tricking anyone. You’re paying such close attention to people’s hopes that you can name them better than they can — the belonging they want, the ease they’re chasing, the person they’re hoping to become. Great brands don’t manufacture a longing. They see one that’s already there, and they answer it.

And here’s what twenty years of it taught me that I never expected: knowing exactly how it works has never once stopped me from feeling it myself.

Which is how I ended up at midnight, looking for Anne Hathaway’s jacket. I can watch a film, or an ad, and see every choice — the lighting, the promise, the exact ache it’s speaking to — and still feel the pull. I can name the feeling I’m reaching for and reach anyway. Fluency didn’t make me immune. It just made me honest about the wanting.

There’s something almost tender in that, once you stop fighting it. The expert and the human are the same person. I understand the reach because I’m a reacher.

I’ll never be above the wanting — I’ve tried, and the jacket always wins. So instead I just ask one honest question before I reach: what am I actually after?

Sometimes it’s something a product truly delivers, and buying it is just good sense. And sometimes it’s a feeling no cart can hold — to be enough, to belong, to feel at home in myself. That gap has never once closed at checkout.

The skill isn’t refusing to want things. Wanting is human, and honestly, it’s part of what makes being alive fun. The skill is knowing what you’re actually reaching for before you reach. Buy the thing, if it serves the life you’re building. Just don’t mistake the thing for the feeling.

The feeling was always an inside job.

So the next time you feel that pull — the jacket, the program, the cream, the whole better life one click away — it’s worth asking, gently: what am I actually reaching for right now?

Answer that honestly, and half the time you’ll still buy it. But you’ll know why. And the other half, you’ll realize the thing you wanted was never for sale.

P.S. If something here made you think, laugh, or feel a little less alone, you can buy me a coffee at buymeacoffee.com/whynotboth. Every cup goes toward more Tuesday mornings at 5:15am doing exactly this.

I waited a long time for that feeling. It never came.

Here’s what I believe now, after years of doing hard things while feeling entirely unready for them: courage isn’t a feeling at all.

It’s a callus.

You aren’t born with it. You build it — slowly, unglamorously, at the exact spot where life keeps rubbing. Rep by rep, in the places that hurt. And you never feel it forming. You just wake up one day a little harder to rattle.

Let me tell you about two of my calluses.

Years ago, I was leading a market-leading skincare brand. We came across data showing something the brand had somehow never acted on: a huge portion of our most loyal customers were women of color. And in all its years of advertising, the brand had never featured them.

So I made what felt to me like an obvious recommendation. Let’s show the women who actually love this brand. Let’s put them in the campaign.

Senior management said no.

I came back with a different case — the loyalty data, the growth opportunity, the whitespace no competitor was serving. They said no again.

I came back a third time, with a third angle.

Three times I sat in that room and made the case. Three times I got turned down. And I want to be honest about what that felt like from the inside, because it’s the whole point: it did not feel like courage. It felt like being a problem. It felt like maybe I should let it go, stop being difficult, read the room.

But I knew this audience was underserved. I knew it was right for the brand, and I knew it was just right. So I kept coming back.

They said yes on the fourth try.

I didn’t win that because I felt brave. I won it because I’d stopped needing to feel brave in order to speak. Each rejection rubbed the same spot, and each time I came back, the spot got a little tougher. By the third no, being told no simply didn’t move me the way it once would have. That’s not a personality trait. That’s a callus.

The harder rep wasn’t at work.

There was a conversation I avoided for months with someone I love. Every day, I chose the easy quiet over the hard truth, and told myself I was keeping the peace. What I was really doing was protecting my own comfort.

When I finally said it — shaking, clumsily, nowhere near as gracefully as I’d rehearsed — nothing exploded. The relationship didn’t shatter. If anything, it got more honest.

And I understood something I keep having to relearn: the fear of the hard conversation is almost always bigger than the conversation itself. I hadn’t been protecting anyone by staying quiet. I’d just been avoiding the rub.

That’s the thing about a callus. It only forms in the place you keep returning to — the spot that keeps making contact, even when everything in you wants to pull away.

Here’s what I’ve stopped believing: that the people who do hard things are feeling something I’m not. That they’ve got some reserve of courage I was skipped over for.

They don’t. They’re just people who’ve done the scary thing enough times that their skin got thicker where it needed to. The fear doesn’t vanish. You just stop letting it be the deciding vote.

So if you’re waiting to feel ready — waiting for the brave feeling to show up before you make the hard call, have the hard conversation, take the hard stand — I’ll save you some time. It isn’t coming. Not first.

The feeling isn’t the beginning of courage. It’s what you get after.

You don’t wait to become brave. You do the thing that scares you, in the exact place it scares you, over and over — and one quiet day you notice the callus is there, holding you up.

What’s the spot in your life that keeps rubbing? That might not be the place you’re failing.

That might be the place you’re building.

P.S. If something I wrote today made you think, laugh, or feel a little less alone — you can buy me a coffee at buymeacoffee.com/whynotboth. Every coffee goes toward more Tuesday mornings doing exactly this.

The first was a deep, settled gladness. I was home. One of my homes. The light was familiar, the quiet was familiar, the person I love was down the hall. I had built this, on purpose, and it was good.

The second was grief.

Not for anything I’d lost — for something I’d chosen. The other city. The other life. The version of me who lives there. I had just driven two days away from it, on purpose, and some quiet part of me was mourning it anyway.

How am I feeling both of these at the same time?

We’re taught, somewhere early, that feelings come pre-sorted. One to a box. You’re either grateful or you want more. You either made the right choice or you regret it. You either love someone or you need to get away from them. Name the feeling, file it, move on.

So when two opposite feelings show up at once, the instinct is to treat it like a problem to solve. Which one is the real one? Which one am I supposed to override?

But I’ve started to believe the realest things in life don’t live in the boxes at all.

They live in the grey. In the place where two opposite truths sit side by side — both completely real, sharing the same chest.

I can grieve a life I chose to leave. No regret, and real grief, at the very same time.

I can love someone deeply and still need to disappear into a room by myself and close the door. The love is true. The need to be alone is also true. Neither one cancels the other out.

I can be profoundly grateful for everything I have and still, quietly, want more. Not because I’m ungrateful. Because I’m a person, and people are allowed to hold both.

Two opposite things, both true, sharing the same chest.

For a long time, I treated that as a sign something was wrong with me. If I couldn’t sort my feelings into one clean pile, I figured I must be confused. Indecisive. Not doing the work.

I had it backwards. The grey isn’t confusion. It’s honesty that refuses to round itself off.

The lie is the clean answer — the tidy “I’m fine,” or “I’m not,” the single tidy feeling I perform because it’s easier to explain. The truth is almost always more than one thing at once. Flattening it down to one is what actually costs me.

And here’s what changed when I stopped flattening: I stopped arguing with myself.

I used to spend so much energy interrogating my own feelings, trying to decide which one to believe and which to dismiss. Now I just let them both be true. I get to be a whole person having a complicated, human response — instead of a simpler one, performing a clean answer for an audience that was only ever me.

That’s where the relief actually lives. Not in resolving the grey. In finally being allowed to stand in it.

What are the two true things you’re holding right now?

P.S. If something I wrote today made you think, laugh, or feel a little less alone — you can buy me a coffee at buymeacoffee.com/whynotboth. Every coffee goes toward more Tuesday mornings at 5:15am doing exactly this.

When I want something — really want it — I talk myself out of it first.

Not all at once. Quietly. Reasonably. I build a calm little case for why it won’t happen, why I shouldn’t bother, why wanting it is a bit naive. And by the time I’m done, I’ve usually convinced myself I didn’t want it that much anyway.

Want nothing, lose nothing. Safe.

A few months ago, an opportunity came up that I wanted badly.

I won’t say what it is yet — it’s still in progress, and I’m a little superstitious about saying it out loud too soon. But I can tell you the shape of it. It was something I’d quietly wanted for a long time. And going for it meant doing the one thing I avoid at all costs.

Getting in front of a camera.

Recording myself. On video. Watching it back. Sending it off to be judged by people I’d never met.

And the case built itself, fast and convincing:

You’ll never get it anyway. Do you know how many people try for these? And it means getting on camera — the thing you hate most. Why put yourself through all that discomfort just to get your hopes up and have them crushed? Be realistic. Save yourself the letdown.

It sounded so reasonable. It sounded like wisdom. It sounded like the responsible, grounded, grown-up thing to do.

It was none of those things. It was fear.

But fear never shows up as fear — not with me. It’s far too smart for that. It learned a long time ago that it couldn’t run me by frightening me; I’d have seen it coming and fought back. So it did something cleverer. It stopped announcing itself and started impersonating the people I trust.

It put on the voice of wisdom. Of logic. Of the calm, responsible adult who only wants what’s best for me. It spoke so softly and so reasonably that it sounded exactly like good judgment — and then it pulled up a chair at the head of my life and ran the place. For years. Unquestioned. Because who argues with the sensible voice in the room?

I had handed the biggest decisions of my life to the most frightened part of me, simply because it had the good sense to never once sound afraid.

Because if I never hoped, I could never be disappointed. That was the deal it offered. The quiet trade I’d been making my entire life.

This time, I noticed it.

I sat there and actually listened to the voice. And for the first time, I asked it something back: whose voice is this, and what is it really protecting me from?

It didn’t have a good answer. It never does.

So I did the thing. I got on camera. I recorded it badly, then less badly, then well enough. I sent it off. I let myself want it — out loud, on the record, where it could actually hurt.

Here’s what I always believed caution was doing for me:

Protecting me. Keeping me safe. Saving me from the crushing letdown of wanting something and not getting it.

Here’s what it was actually doing:

Making me grieve things before they were even gone.

Talking myself out of hope never spared me the disappointment. It just moved the disappointment earlier and made it permanent. Instead of risking one clean loss at the end, I signed up for a low, quiet disappointment the entire way through — the disappointment of never trying. The dull ache of wanting something and pretending I didn’t.

I did that math wrong for decades.

Because here’s the part no one tells you: the hope was never the dangerous part. Hoping and losing hurts once, sharply, and then it heals. But talking yourself out of hope to stay safe doesn’t heal. It just quietly shrinks your life, one un-tried thing at a time, until you’ve built a small, careful existence and called it being realistic.

I don’t know yet how this will turn out. I might get it. I might not.

But I’m already further than the version of me who almost didn’t try ever believed I’d get. And the next time that calm, reasonable voice starts building its quiet case against something I want, I’ll know exactly who’s talking.

Not wisdom. Not reason. Just fear, running the same quiet con it always has — sounding like logic, passing for sense. And this time, I’m not buying it.

I’m done pre-paying a disappointment I might never even owe.

What have you talked yourself out of wanting — and what might happen if you let yourself want it out loud?

P.S. If something I wrote today made you think, laugh, or feel a little less alone — you can now buy me a coffee at buymeacoffee.com/whynotboth. Every coffee goes toward more Tuesday mornings at 5:15am doing exactly this.

The essay is finished. It’s just sitting there, waiting for me to press one small button. Publish. A few hundred people will see it. Maybe more. Maybe — and this is the thought that actually stops me — no one.

My finger hovers. My chest does something complicated.

Who do you think you are.

There it is. The oldest voice I own.

Nobody warns you that getting good at something makes you comfortable. And comfortable is, quietly, a kind of cage.

I’m good at some things. I’ve built a whole adult life on being the competent one — the woman people hand the hard thing to because they know she’ll figure it out. I know that feeling in my body. The ease of it. The quiet authority of knowing exactly what you’re doing.

And then I went and did this. Started something I’m, by any honest measure, not good at yet. On purpose. In public.

Voluntarily.

Somewhere I absorbed a rule I never agreed to: that being a beginner is for the young. That the window for fumbling and being bad eventually closes, and after that you’re supposed to have arrived. Arrived, and stay arrived.

So starting over now feels like a small rebellion. Or an embarrassment. Some days I can’t tell which.

Shouldn’t I know how to do this by now?

But I don’t. I write things I’m proud of and things I delete at 6am. I say it wrong, then say it again. In this one corner of my life, I’m starting from nothing.

What surprised me is that both things are true at once.

I can be an expert and a novice in the same week. The woman who walks into a room knowing exactly what she’s doing, and the one fumbling in the dark for the light switch. Same person. Same Tuesday.

I used to think it was one or the other — that you were either accomplished or beginning, and the two couldn’t live in the same body. They can. Mine does.

And here’s what I didn’t expect. The being-bad cracked something open.

Mastery is comfortable. It’s also a little numb — your hands do the work while your mind wanders off. But beginning is awake. Every nerve online. Every small win enormous. The terror and the aliveness, it turns out, are the same feeling in different coats.

The thing I’d been avoiding because I might be bad at it became the thing that’s made me feel most alive. And not as a reward for being brave. I got it the second I let myself be terrible.

So I press publish.

My chest still does the complicated thing. Who do you think you are still shows up, right on schedule. I’ve stopped waiting for it to leave. It can come along. It just doesn’t get to drive.

If there’s something you’ve decided you’re too accomplished, too far along, too old to risk being bad at — I’ll tell you the quiet part. That might be the exact thing worth starting.

Not because you’ll be good at it. Because you won’t be. Not yet.

And the not-yet is the most alive I’ve felt in years.

So I stop watching the cursor. And I press the button.

P.S. If something I wrote today made you think, laugh, or feel a little less alone — you can now buy me a coffee at buymeacoffee.com/whynotboth. Every coffee goes toward more Tuesday mornings at 5:15am doing exactly this.

The coffee’s too hot to drink yet. The house hasn’t started asking me for anything. For about an hour, before the day finds out I’m awake, this time is mine.

And every single morning, something tries to take it.

This morning it was the inbox. A name I’d been waiting on. A reply I could send in four minutes, just to clear it, and then I’d write. That’s how it always starts. Just this one thing. Just clear the urgent and earn the hour back.

You can write after.

I know that voice. I’ve listened to it for twenty years. It’s the one that says the important thing can always wait behind the urgent one. Answer the email. Take the call. Build the brand — someone else’s brand — and tell yourself you’ll get to your own life on the weekend.

The weekend never came. The hour after never came either. There’s always one more thing with a louder claim than the quiet thing you promised yourself.

So this morning I didn’t open the inbox.

I want to make it sound braver than it was. It wasn’t brave. It was just me, in the dark, deciding the email could wait sixty minutes and the promise couldn’t. The name in my inbox will still be there at eight. The version of me who said I will build something that’s mine — she only gets the early hour. Trade it away and she doesn’t get a later one. She just doesn’t get it.

We talk about negotiation like it’s a table with two sides. Your raise. Your contract. The number, the clause, the person sitting across from you.

But the negotiations that actually decide your life don’t have anyone else in them.

It’s just you, at 5:44am, deciding whether the thing you promised yourself is real or only something you say.

I gave that hour away for two decades. I called it being responsible. I’m not calling it that anymore.

The email got answered at eight. The world did not end. And this got written — in the dark, before anyone could talk me out of it.

What’s the hour you keep quietly handing back, and who did you promise it to before you forgot?

This one's free, like all of them. If it was worth your while, you can buy me a coffee — fitting, given the hour. https://buymeacoffee.com/whynotboth

Extremely organized.
Wonderful attention to detail.
Deeply committed to avoiding embarrassment at all costs.

It never once told me not to pursue ambition. In fact, fear loves ambition. Ambition gives fear structure. Deadlines. Metrics. Respectability.

Fear just preferred we revisit certain things after additional research.

After more certainty.
After better timing.
After I felt more qualified.
After I had a clearer plan.
After I became slightly more impossible to criticize.

Fear has incredible PR.

Especially for women who grew up getting rewarded for being competent.

Because fear rarely introduces itself honestly. It doesn’t walk into the room and announce itself as fear. That would be too obvious. Too emotionally inconvenient.

No, fear usually arrived in my life dressed as professionalism.

Professionalism sounds much nicer.

Professionalism gets promoted.
Professionalism gets called mature.
Professionalism gets invited into leadership meetings.

Fear loves professionalism because professionalism is socially rewarded fear.

Somewhere along the way, I became very good at confusing the two.

I became highly prepared.
Highly adaptable.
Highly composed.
Very pleasant to work with.

I learned how to read rooms quickly. How to anticipate needs before they were spoken. How to make myself useful almost immediately.

Fear was excellent at all of this.

Fear thought visibility should be earned carefully.
Fear preferred polish over spontaneity.
Fear loved a strategic rollout.

Fear believed deeply in waiting until I was fully ready, which is interesting because “fully ready” appears to be a fictional location with no confirmed address.

The strange thing is, fear was not ruining my life.

Honestly, fear helped me build a fairly impressive one.

A good career.
A strong reputation.
Financial independence.
Achievements I genuinely worked hard for.

Fear was organized. Reliable. Productive. Fear answered emails promptly.

And because of that, I think it took me a long time to recognize the cost.

Not dramatic cost.
Not movie-scene regret.

Smaller things.

How often I delayed things I cared about because they still felt too exposed.
How often I overprepared before allowing myself to be visible.
How often I translated desire into strategy before I allowed myself to experience it honestly.

I spent four years thinking about writing publicly before I actually did it.

Four years.

Fear had concerns.

Fear wanted a clearer positioning strategy.
Fear wanted consistency.
Fear wanted proof I would be good at it before I became visible doing it badly.
Fear wanted to know where this was all leading.
Fear would have loved a five-year plan.

Writing publicly has been uncomfortable in ways my career rarely was.

There’s no performance review for honesty.
No guaranteed outcome.
No clean KPI for resonance.
No perfect amount of preparation before you say something true out loud and let people have opinions about it.

Which, for someone who has historically enjoyed competence, has been deeply irritating.

But writing has also exposed something I didn’t fully realize before:

Fear and intelligence are not the same thing.

Fear is intelligent.
Fear notices patterns.
Fear identifies risk.
Fear is often technically correct.

But fear’s primary objective is avoidance.

Avoid embarrassment.
Avoid uncertainty.
Avoid rejection.
Avoid being seen too early.
Avoid wanting something publicly before it’s guaranteed.

And I’m beginning to suspect those priorities are sometimes incompatible with a fully lived life.

I still mistake fear for maturity sometimes.

Fear sounds reasonable.
Organized.
Prepared.
Good with logistics.

Fear has a calendar invite for every possible worst-case scenario.

I just don’t think fear fully understands the difference between protecting a life…

and participating in one.

It started early. The grade. The teacher’s approval. The look on my parents’ faces when I brought home something worth celebrating. Gold stars meant I had done it right. That I was enough. That I could exhale — at least until the next one was available to chase.

I never really stopped.

I just got better at disguising it as ambition.

The gold star followed me into my career in ways I didn’t fully see until recently.

The promotion. The title. The brand everyone recognized. The room I finally got invited into. Each one felt like a gold star — external confirmation that I was on the right track, doing the right things, becoming the right version of myself.

And each one, if I’m honest, lasted about as long as a gold star sticker actually does.

Shiny for a moment. Then just part of the background.

My partner and I play Overcooked together. It’s a chaotic cooking game where you’re supposed to cooperate. I need to get the most stars at every level. Every single time. Cooperation optional apparently.

He finds it funny. I find it revealing.

Here’s what I’ve been sitting with:

The gold star was never really about the achievement.

It was about the confirmation that came with it. The external signal that said: yes. this. you got it right. you are enough.

The problem with outsourcing your sense of enough to gold stars is that someone else is always holding them.

A boss. A hiring manager. A subscriber count. A like. A restack.

And when they don’t come — or when they come and feel smaller than you expected — you’re left with the question the gold star was always helping you avoid:

Am I enough without it?

Three months of writing publicly has been the most direct confrontation with this I’ve ever had. No boss to approve it. No performance review to validate it. Just me, a Tuesday morning, and the decision to put something true into the world without knowing how it will land.

Some weeks the external stars come — the likes, the replies, the message from a stranger that makes the whole thing feel worth it. Some weeks they don’t. And on the weeks they don’t, I’m left sitting with the exact question the gold star was always helping me avoid.

Am I enough without it?

I’m learning the answer is yes. Not because the external validation stopped mattering — it still does, if I’m honest. But because I’m slowly becoming someone who doesn’t need it to begin.

That’s the gold star nobody gives you. You have to give it to yourself.

Where are you still waiting for someone else to hand you the gold star you’ve already earned?

P.S. If something I wrote today made you think, laugh, or feel a little less alone — you can buy me a coffee at buymeacoffee.com/whynotboth. Every coffee goes toward more Tuesday mornings doing exactly this.

Stay true to your brand voice. Don’t chase what’s working for someone else. Don’t morph into something you’re not because a shiny object convinced you that who you are isn’t enough.

I said this with authority. With conviction. With receipts.

And then three months ago I sat down to build something with my own name on it — and forgot every single word of it.

I started writing publicly in February. Not because I had a strategy. Because I had a whisper I’d been ignoring for four years that finally got loud enough to act on.

And somewhere in those first few weeks I did the exact thing I had warned every founder never to do.

I started watching what was working for other writers. Other builders. Other women on Substack with thousands of subscribers and clear niches and polished brands.

And I started wondering if I should be more like them.

Here’s what 17 years of brand building actually taught me — the lesson I had to relearn for myself:

The brands that fail are rarely the ones that aren’t good enough.

They’re the ones that stop being themselves.

They see someone else’s success and mistake it for a blueprint. They chase the shiny object — the format that’s working, the niche that’s growing, the voice that’s getting the most engagement — and slowly, quietly, morph into something they were never meant to be.

I know this. I have sat across from founders and said: the market doesn’t need another version of that. It needs the thing only you can make.

And still. Three months in. I almost did it to myself.

Stay true to your core voice. Don’t morph into something you’re not because the shiny objects will convince you — convincingly, persistently — that who you are isn’t sufficient.

Who you are is the whole point.

It took me 17 years of building brands for other people and three months of building one for myself to finally understand that the advice I’d been giving everyone else was always meant for me too.

I’m not a version of the writers I admire.

I’m the first version of myself.

And that — finally, uncomfortably, with a camera pointed at my face — is enough.

What have you been giving away to everyone else that you’ve never thought to apply to yourself?

P.S. If something I wrote today made you think, laugh, or feel a little less alone — you can buy me a coffee at buymeacoffee.com/whynotboth. Every coffee goes toward more Tuesday mornings doing exactly this.

That they knew they wouldn’t embarrass themselves.
That they had some internal certainty I didn’t.

I don’t think that anymore.

I think confident people just have a higher tolerance for looking stupid.

And once I saw that, I couldn’t unsee it.

Here’s what I’ve been noticing:

• Most of us aren’t afraid of failure—we’re afraid of being seen failing

• Confidence isn’t about ability—it’s about exposure

• The people we admire just cross the line of visibility faster

A few things I’ve clocked recently:

• The person speaking most clearly in the meeting isn’t the smartest—they’re the least self-conscious

• The best content online isn’t always the best—it’s just the most posted

• The people who “seem confident on camera” have just filmed themselves enough times to stop flinching

There’s no moment where they suddenly became confident.

There’s just a moment where they stopped opting out.

Three months ago, if someone pointed a camera at me, something in my body would tighten.

Not dramatically. Not visibly.

But enough.

Enough to overthink what I was saying.
Enough to adjust my tone.
Enough to make me… not quite myself.

And I wouldn’t have called it fear.

I would have called it “not my thing.”

But it was fear.

Not of the camera.

Of how I would look through it.

I’ve been sitting with this idea:

Confidence isn’t a personality trait.

It’s a willingness.

A willingness to:

• say something before it’s perfectly formed

• be seen before you’ve refined yourself

• risk the small, sharp hit of embarrassment

Most people are not lacking confidence.

They’re protecting their image.

And image protection is expensive.

It costs you:

• speed

• visibility

• momentum

• opportunities you don’t even realize you’re missing

Because every time you hesitate, soften, or opt out…

Someone else—who is maybe less prepared, less thoughtful, less capable—is just going.

Not because they’re better.

Because they’re less concerned with how it lands.

That’s the uncomfortable part.

Confidence is not always competence.

It’s exposure.

And exposure compounds.

If there’s one thing I’m carrying into May, it’s this:

I don’t need more confidence.

I need a higher tolerance for looking stupid.

Where are you holding back—not because you’re not ready, but because you don’t want to be seen not ready?

P.S.

If this resonated, I write about the gap between who we are privately and how we show up publicly.

If you’re in that tension too, you’ll probably like what’s coming next.

(And if you want to support the work, here’s a “buy me a coffee” link.)

I want to be a TEDx speaker.

I didn’t tell anyone. I just wrote it down and let myself believe — quietly, carefully — that it might be possible.

Then I closed the journal and went about my life.

A few weeks ago something showed up in my feed.

A TEDx talk. In my area. Open applications.

I want to be careful about how I say this because I don’t want it to sound like magical thinking. But I’ve been doing enough unlearning this year to know the difference between a coincidence and an answer.

This felt like an answer.

I clicked through immediately. I read every word of the application. I felt the specific kind of excitement that lives right next to terror — the kind that means something actually matters.

And then I saw it.

The application requires a video submission.

Let me tell you something about me and cameras.

I spent years making other people visible for a living. Building brands, creating content, putting faces and stories in front of audiences.

Just never my own face. Never my own story.

Every time someone pointed a camera at me I said no.

Me? I’m the one behind the scenes.

I said it so many times it stopped feeling like a choice and started feeling like a fact. Like something that was just true about me.

I’ve been publicly working on this. Writing about it. Committing to being 1% more visible every day. Telling anyone who reads this newsletter that the fear is loudest at the threshold — not before, not after. Just at the door.

And now here I am. At the door.

The application deadline is Friday.

I’m recording the video this week.

Here’s what I know about intentions: setting one isn’t the same as wishing for something. It’s declaring that you’re available for it. That when it shows up — in whatever form it takes — you won’t look away.

I wrote it in my journal in January. I didn’t know what form the answer would take.

Turns out it took the form of the exact thing I’ve been most afraid of.

A camera. A deadline. A stage I haven’t earned yet but am about to ask for anyway.

The audacity of that is not lost on me.

Neither is the fact that I have no choice but to do it anyway.

What intention have you been carrying quietly — and what would it look like to finally say yes when it shows up?

P.S. I’ll let you know what happens. Whatever happens. That’s the deal I’ve made with myself — to tell the truth about all of it, not just the parts that work out.

Not casually. Properly. I bought the equipment. I found beginner-friendly recipes. I told my friends they were my official taste-testers.

They were enthusiastic. Briefly.

So I pivoted. I started bringing everything I made to the volunteers at the Goodwill near my house and asking for honest feedback. They were kinder than my friends but the verdict was the same.

I was not a baker.

Here’s the thing though: the problem wasn’t the baking. The problem was that I had spent years watching baking championship shows convinced I would love doing it myself. Turns out I love watching other people bake. I do not love baking.

That’s a completely valid thing to discover about yourself — but you can only discover it by trying.

Two years ago I decided I wanted to build a brand of my own.

I had spent my entire career building brands for other people — startups, celebrities, founders with big visions and limited budgets. I was good at it. I loved it. And somewhere along the way I started wondering: what if I did that for myself?

So I did what I know how to do. I bought the trademark. I wrote the formula brief. I met with manufacturers. I built the foundation for a pet supplement brand from scratch.

And then it came time to place the first product order.

I sat in front of that order form and felt something I recognized immediately — not excitement, not nerves, not the good kind of uncomfortable that means you’re growing.

Just a very clear, very quiet: no.

I had spent years managing inventory challenges in my day job. The forecasting, the overstock, the shortages, the supplier conversations at 11pm. I had zero desire to own that problem. Not for myself. Not for a brand with my name on it.

I closed the laptop. I walked away from the whole thing.

And I learned something I couldn’t have learned any other way.

Here’s what I thought I was learning from the baking and the brand:

That I wasn’t cut out for it. That I had wasted time. That trying things you’re not good at is embarrassing and expensive and a little bit humiliating.

Here’s what I was actually learning:

That I have spent most of my life needing to be good at something immediately — before I’ve earned the right to be good at it. That perfectionism isn’t just a quirk or a personality trait. It’s a wall. And it shows up every single time something has my name on it in a way it never does when I’m building for someone else.

I can hold space for imperfection in other people’s work all day long. I’ve built entire careers in the messy, uncertain, figure-it-out-as-you-go early stages of other people’s brands.

But when it’s mine? The standard shifts. The tolerance for not-yet disappears. The wall goes up.

That’s not a character flaw. That’s programming. And I couldn’t have seen it clearly without trying the thing badly first.

The baking taught me I love watching creativity more than doing it — which freed me to stop pretending otherwise.

The brand taught me that what I actually want to build is something I’m genuinely willing to be imperfect at in public. Something where the not-yet doesn’t stop me. Something where my name on it makes me braver, not more afraid.

Turns out that’s this. The newsletter. The writing.

I tried a lot of things badly to find the one thing I’d keep trying even when I was terrible at it.

That’s not failure. That’s the whole process.

What have you tried badly that taught you something you couldn’t have learned any other way?

P.S. If something I wrote today made you think, laugh, or feel a little less alone — you can now buy me a coffee at buymeacoffee.com/whynotboth. Every coffee goes toward more Tuesday mornings at 5:15am doing exactly this.

I said it for years. To myself. To the teams I led. In boardrooms and planning sessions and budget reviews where wishful thinking had no place at the table.

It was practical. It was smart. It kept us grounded in data and execution rather than fantasy.

And somewhere along the way it became something else entirely.

It became a way of talking myself out of wanting things that felt too big, too uncertain, too far outside the lane I’d already proven myself in. A pre-emptive defense against disappointment dressed up as professional wisdom.

If I don’t hope for it, I can’t be hurt when it doesn’t happen.

That’s not strategy. That’s self-protection.

A few years ago I almost didn’t make a pivot that changed everything.

I had spent my career leading marketing for large, established corporate brands. Proven playbooks. Established budgets. Teams and infrastructure already in place. I was good at it. I was celebrated for it. It was safe in the way that things are safe when you already know you can do them.

The opportunity in front of me was different. Startup brands. Limited budgets. No playbook. A celebrity co-founder. Everything I’d have to figure out as I went.

Every practical, strategic, data-driven part of my brain said: this is not a smart move. You have no proof you can do this. Stay where you’re proven.

And underneath all of that, dressed up as wisdom: don’t hope for this. You’ll only be disappointed.

I almost listened.

I didn’t.

And what followed was some of the most uncomfortable, exhilarating, identity-expanding work of my career.

I built a brand from scratch for a celebrity. I learned what it means to be scrappy with limited resources. I built a team I genuinely loved working with. I discovered capabilities in myself I didn’t know existed because I’d never been in a situation that required them.

None of it would have happened if I had let “hope is not a strategy” talk me out of the leap.

Here’s what I understand now that I didn’t then:

Hope isn’t the opposite of strategy. Hope is the fuel that makes strategy worth executing.

You can have a concrete plan AND allow yourself to want it to work. In fact the wanting — the genuine, vulnerable, this-matters-to-me hoping — might be exactly what makes you execute the plan with everything you have instead of going through the motions of it.

The false choice was never hope OR strategy.

It was always both.

I’m in another pivot right now. A different kind — less about career and more about identity. About finally claiming the creative half of myself I spent decades being told didn’t belong to me.

And I catch the old voice sometimes. Don’t hope for this. You’ll only be disappointed. Hope is not a strategy.

Now I know what to say back.

Stop talking yourself out of hope.

The leap I almost didn’t take gave me everything. The newsletter I almost didn’t start is giving me something I didn’t even know I was missing.

Hope wasn’t the problem. Protecting myself from it was.

What have you been talking yourself out of hoping for — and what might be waiting on the other side of that leap?

If this resonated, please forward it to someone who needs permission to stop protecting themselves from hope.

I mentioned the newsletter. The essays I’ve been writing. The both/and I’ve been exploring — the tension between who we’ve been told to be and who we actually are.

The look on their face said everything the words didn’t.

Why would you start something like that at this stage in your life?

I felt it immediately. That low hum of frustration that lives just below the surface when you’re in the middle of becoming something and the people around you can only see where you’ve already been.

I explained myself. I talked about the surge of creative energy I’ve been feeling. The writing as an outlet. The genuine belief that what I’m exploring isn’t unique to me — that somewhere out there, someone is reading these words and feeling a little less alone in their own tension.

But I drove home with the question still sitting in my chest.

At this stage in your life.

As if becoming is something with an expiration date. As if there’s a point at which the door closes on reinvention and you’re supposed to simply manage what you’ve already built.

I’ve been thinking a lot lately about the gap between where I am and where I’m going. About the restlessness that lives in that gap. About the cultural pressure to perform contentment — to smile and say it’s about the journey, not the destination — when the honest truth is that the journey is hard and the destination still feels far away.

And here’s what I’ve come to understand about that platitude: it fails in both directions.

It minimizes everything that actually happens during the journey — the doubt, the frustration, the moments of wondering if any of this is going anywhere. AND it ignores the very real, very human pull toward the destination. The wanting. The drive. The I am not done yet that lives in your chest whether you say it out loud or not.

Making peace with where you are doesn’t mean pretending the restlessness isn’t there. It doesn’t mean performing gratitude for a version of your life that doesn’t yet reflect who you’re becoming.

It means trusting the restlessness. It means letting the creativity out even when the people around you don’t understand why you need to. It means writing the newsletter, posting the Note, saying the true thing out loud — not because you’ve arrived, but because the act of creating is how you get there.

I’m not at peace because I’ve stopped wanting more. I’m at peace because I’ve stopped waiting for permission to want it.

The question “what are you doing it for?” has a simple answer:

For the woman who reads this and finally feels seen. For the version of me that spent years being told she was strategic, not creative, and believed it. For everyone who has ever been made to feel like becoming something new at this point in their life requires an explanation.

You don’t owe anyone an explanation for still becoming.

Are you making peace with where you are — or are you waiting until you arrive to finally give yourself permission to be at rest?

Samantha Jones said it like a punchline — and it was. But every woman in that scene knew the feeling underneath it. The moment a form hands you a category and says: this is you now. Pick one.

I’ve been thinking about that feeling for a long time. Not because of age boxes. Because of all the other boxes.

You know the moment. You’re filling out a form and you get to the part that asks you to check a box. One box. The one that best describes you.

And you look at the options and think: none of these are right.

I’ve been there more times than I can count. Staring at a race question with no box that holds the full truth of my background. Sitting with friends watching the Olympics while someone turns to me and asks — completely innocently — which team I’m cheering for, as if the answer should be obvious. As if I should only belong to one country. Answering “analytical” in a job interview when asked to pick my strongest skill, quietly setting aside the other half of the answer because the approved version was easier to explain.

Different forms. Different rooms. Same request: simplify yourself. Pick one. Make it easy for us.

I never could.

At some point I stopped being confused by the boxes and started being annoyed by them.

Because I realized the form wasn’t asking me a question. It was making an assumption — that I could be sorted. That if the options were thorough enough, one of them would fit. That the full complexity of a person could be captured in a checkbox.

It can’t. Not for me. And I suspect not for you either.

This newsletter is what I built instead of checking a box. A place that starts from the assumption that you contain multitudes — and that the most interesting, fully-lived version of your life exists not in choosing between two things, but in refusing to.

So here’s my invitation.

Stop trying to fit yourself into their boxes.

You are not a checkbox. You are not a category. You are not the simplified, rounded-down, easier-to-explain version of yourself that forms have been asking for your whole life.

You are the race question with no right answer. The passport that belongs to two countries. The interview candidate who is both analytical and creative and refuses to pretend otherwise.

You are the both/and.

And if nobody has said it to you yet — let me be the first.

Honey, welcome to my box.

If this resonated, forward it to someone who has never quite fit the box either.

I was telling her about everything I’m either doing or considering — including starting a newsletter at this stage of my life, a creative venture I’d been quietly sitting on for years. I was lit up talking about it. And she stopped me and said: midlife is the time in life when you’ve achieved what you set out to achieve. When you can begin to enjoy the fruits of that labor. When you dial down ambition.

I looked at her like she had three heads.

Ummmm, WHAT!?!?

I know she said it with the best of intentions. She loves me. She wants good things for me. But if that’s the message midlife women are being given — then we are still asking women to make themselves smaller just when they’re finally getting interesting.

Here’s what I know about the women I’m surrounded by in midlife: they are not coasting. They are not quietly enjoying the view from a plateau they’ve decided is high enough. They are pivoting, building, creating, questioning, starting over, starting fresh, starting things they were too afraid to start at 25 when they were still performing the version of themselves they thought the world wanted.

Midlife isn’t the beginning of the end of ambition. For a lot of us, it’s the first time ambition finally belongs to us. Not to a title. Not to someone else’s expectations. Not to a version of success we inherited without questioning.

My mom wasn’t wrong to say what she said. She was handed the same story I was. But I’m not passing it on.

If you’ve been told it’s time to dial down — what would it mean to dial up instead?

I was in my cubicle, in the row where all the other assistant managers sat, staying late with my peers to work through the prior year’s results. When I finally left the office it was dark outside. I was mentally exhausted and completely wired — the way you only feel when you’ve spent hours on something that matters and you know the work is good.

My boss called me into his office the next morning to review it. He smiled as he read through it and told me it exceeded his expectations. Excellent work, he said. Stellar strategic chops. Keep honing those skills.

I was 20-something, newly out of grad school, and I held onto those words like a compass.

So I did exactly what he said. I honed. I excelled. I built a career on the strength of that feedback and the many versions of it that followed. Strategy. Analysis. Numbers. These were my things. This was who I was.

And for a long time, it felt like enough.

Then something shifted.

A friend showed me a painting she’d made at an art class she’d started taking. Another sent me a video of her dance performance at her studio’s recital. And something I didn’t have a name for crept in quietly every time.

Envy.

Not the loud, ugly kind. The quiet kind. The kind you can rationalize away before it gets too uncomfortable.

It’s ok that I’m not a creative person, I told myself. I’m a strategic one. We can’t all be good at everything.

And I believed it. Mostly.

But even after long days of doing work I genuinely loved, something still felt missing. A restlessness I couldn’t quite locate or explain. Like a room in the house I kept walking past but never opening the door to.

Years later, a mentor called me after seeing an ad for a brand I was leading. She mentioned how creative it was. I told her the concept had been my idea.

There was a pause, and then: Wow. That’s so creative.

I brushed it off immediately. Reflexively. The way you dismiss a compliment you don’t know how to receive because it doesn’t match the story you’ve been telling about yourself.

That’s not me, I thought. I’m good at strategy and numbers. Creative? No. That’s not me.

Except it was. It had always been.

The accolade from my first boss wasn’t wrong. He saw something real. But the story I built around it — I am this, therefore I am not that — that story was the lie. And I kept choosing it, over and over, every time someone handed me evidence to the contrary.

Here’s what I know now: envy is a compass. It doesn’t point at what you wish you had. It points at what you already are but haven’t given yourself permission to claim yet.

The restlessness wasn’t dissatisfaction. It was creativity with nowhere to go.

And unused creativity doesn’t disappear. It accumulates. It finds ways to remind you it’s there — in the quiet envy, in the vague sense that something’s missing, in the whisper that keeps returning no matter how many times your rational brain talks you out of it.

I started this newsletter because I finally stopped mistaking the accolade for my identity.

The strategy and the creativity were never in competition. They were always both mine.

What have your accolades been telling you that you are — and what have they been quietly telling you that you’re not?

I was in my home office, building a brand from scratch — exciting work, a big departure from the decade-plus I’d spent inside large organizations with established processes and inherited playbooks. I was deep in go-to-market strategy, in flow, when something stopped me cold.

A whisper.

Not a thought exactly. More like a knowing that arrived uninvited and landed in my gut. What would your life look like if you shared the tension you’ve carried your whole life — between the good girl and the expansive woman — with others? What if putting that into words helped someone feel less alone?

I was winded by it.

And almost immediately, my rational brain took over.

What would you even do with that idea? Are you ready to be that vulnerable with strangers? You’re a corporate marketer — not some woo woo freethinking creative.

So I didn’t do anything. I went back to the strategy deck.

But the whisper didn’t go away. Over the next four years it kept returning — quieter than my rational brain, but more persistent. And everywhere I looked, I saw evidence that I wasn’t the only one carrying this. Female colleagues navigating the gap between who they were at work and who they were at home. Friends who had shrunk themselves to fit rooms that were never built for them. Women on screens and in conversations describing a tension they couldn’t quite name — the pull between the life that looked right and the one that felt true.

The whisper knew something I wasn’t ready to admit yet.

What finally changed? Partly, I think, it’s that I’ve grown more aware of my own mortality — and more present to the reality of watching a parent age. Time looks different now. Possibility feels more urgent. And somewhere along the way I started caring less about other people’s opinions and more about what it would cost me not to act.

The cost, I realized, wasn’t failure. It was purpose. It was the specific way I want to help others feel less alone and more understood — something I can only do by saying the quiet thing out loud.

So here I am. Saying it.

What has your whisper been saying — and what has your rational brain been telling it in return?

I thanked her. And then I said: I’m just writing these posts in the hopes that they resonate with people and make them feel less alone. It’s just something small I’m doing.

She stopped me immediately.

“You’re doing the thing you wrote about last week.”

I paused. And then — OMG. She was right. I was doing it again. One week after writing a whole essay about refusing to play small, I had just described my own newsletter as something small without even noticing.

That’s when I understood something I hadn’t fully grasped when I wrote that first piece:

The programming runs so deep I don’t even recognize when I’m running it.

I grew up absorbing a specific set of rules. That dreaming is wonderful and creative and fun — but expecting your dreams to actually materialize? That’s silly. Naive. Setting yourself up for disappointment.

And then as I got older, a second layer got added. That as a woman, your purpose is to be selfless and nurturing. That you sacrifice. That pursuing something purely for yourself — purely because you want it — is indulgent. Selfish. A betrayal of the roles you’re meant to play.

So I learned to make myself small. To put my needs second — to my former spouse, to my family, to everyone in the room. To preemptively shrink whatever I wanted before anyone else could tell me it was too much.

Playing small didn’t feel like a choice. It just felt like who I was.

But there was always another voice underneath.

Quieter. Less sanctioned. Harder to justify.

She didn’t want recklessness. She didn’t want to blow anything up.

She just kept saying: it’s okay to want this for yourself. It’s okay to think about you.

Recently, that voice has gotten louder. I’ve been trying to actually listen to her — to give myself permission to put my needs first without immediately punishing myself for it. To stop treating my own ambitions like a guilty secret.

And then I described my newsletter as something small in casual conversation and didn’t even notice.

I’m not on the other side of this. I want to be clear about that. This isn’t a story about a woman who figured it out. This is a story about a woman who is still, in real time, catching herself — being caught by the people around her — and choosing differently, one moment at a time.

I’m proud of the progress. And I’m still very much in it.

The essay was the easy part. Turns out I have to write it again every single week — not here, but in the moments no one sees. In the offhand comment. The reflexive minimizing. The armor that goes on before I’ve decided to put it on. That’s the real work. And I suspect I’m not the only one doing it.

I’d love to know — have you ever caught yourself doing the thing you said you wouldn’t do anymore? Reply and tell me. I read every response.

And if this resonated, the best thing you can do is forward it to one person who needs to read it. That’s how this grows.

See you next week.