Summer Cat knows that when the kids are out of school, vacations are planned, and the days are long, productivity will take a hit. She embraces it. She lowers expectations. She goes to the pool… a lot.

Summer Cat had a good run.

Last week alone included tie-dying, the farm, grandparent visits, Sesame Place, and a lot of squeezing the last bits out of summer.

But somewhere between the farm and Sesame Place, another cat started getting restless.

Work Cat is back.

My kids start school this week, and while I’m sad to see summer end, I’m also very ready to get back into a routine. My fall is shaping up to be busy, and I’ve filed a lot of things under “when school starts.”

Of course, “when school starts” isn’t quite the productivity utopia I apparently imagined.

My husband and I spent Saturday night updating our shared Google Calendar with all the kids’ days off. They have different spring breaks.

We also learned that November contains only 13 normal school days, and throughout the year several mysterious days may or may not become days off depending on whether it snows.

Still, there’s something about September that feels like a reset. It’s easier to build momentum and fall back into a rhythm, and I’m excited about what’s ahead.

A few things Work Cat has on the calendar:

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1. Speaking

I’m incredibly honored that two major conferences accepted my proposals this fall.

I’ll be speaking at the Society of Women Engineers’ Global WE conference in Boston in November. My proposal was selected from more than 1,000 submissions!

I’m also speaking at the NJ Conference for Women in October, which was actually one of my goals for this year after attending last year’s conference. It was one of the best conferences I’d ever been to, and I’m really excited to be on the other side of the stage this time. If you’re in the area, you should definitely join me there.

I’ll also be returning to Wharton to guest lecture again this year, which remains one of my favorite things to do.

I’d love to add another event or two while I’m already on the road. I’ll be in Boston around November 5 and Philadelphia November 16–17. If you know a company or organization that could benefit from my talk or workshops such as Learn by Doing: How to Build Momentum When You Don’t Have All the Answers, please reach out!

2. A Sub-2 Half Marathon

Yes, yes. Always with the running.

My goal race to try to break two hours in the half marathon is also this fall, right after SWE. Conveniently, I’ll be in taper mode for the conference, which means it shouldn’t mess too much with my training plan 😅

A minor knee injury has complicated training a bit, but I’m still hopeful I’ll get there.

3. More Consulting

I’m also looking forward to doing more advising and consulting this fall.

I work primarily with founders and leadership teams who need senior-level marketing and GTM help but don’t necessarily need (or aren’t ready for) a full-time CMO.

I have some bandwidth for additional clients this fall, so if that sounds like you or someone you know, I’d love to talk.

Summer Cat will miss the pool.

But Work Cat has things to do!

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About Catherine Connelly:

Catherine Connelly is an entrepreneur, keynote speaker, and fractional leader. She co-founded myYearbook as a teenager and helped grow it into The Meet Group, a NASDAQ-listed social discovery and livestreaming company acquired for $500 million. Today, she is the author of Designing Success: Lessons from 20 Years as a Female Tech Entrepreneur, writes the weekly newsletter Growing Up Startup, and speaks about innovation, decision-making, and unconventional career paths.

When we talk about competitive advantage, we usually mean something impressive.

It may be a proprietary technology or a skill only you can do. Perhaps you have the ultimate powerful network or a powerhouse brand.

I’ve found, though, that the people who stand out professionally usually aren’t doing stuff that’s wildly differentiated, but rather that they do the banal things exceedingly well.

They’ve mastered the “boring skills” that should frankly be the status quo… until you realize after working with enough people that many of those baseline skills are, well, not there in many people.

These are the low-hanging fruit that nearly everyone can improve to build a reputation as someone others want to work with.

1. Respond Quickly

Jason Feifer is the editor in chief of Entrepreneur, writes books and the fantastic One Thing Better newsletter, hosts podcasts, speaks, and seems to have seventeen other things happening at any given moment. He’s a very busy guy.

However, any time I’ve reached out to him, he responds.

A few months ago, I sent him something that made me think of him. It wasn’t even something that needed a response – a Gmail reaction would have been more than enough.

He responded within minutes.

I’ve noticed that some of the busiest, most successful people I know are among the most responsive.

I don’t think that’s a coincidence.

Responsiveness is a competitive advantage because when you respond, you signal that they’re worth your time and that you’re someone people can count on.

Now, of course, I don’t mean you need to respond to every cold email or message you get, but being responsive lets other people know they can work with you.

It’s hard to respond quickly. (With summer-Cat in full force, I know I am way behind, but I will dig myself out of my terrifying inbox number.)

Or sometimes you haven’t been away, but you just have a lot on your plate. But instead of leaving them on read, or more likely, no-idea-if-it’s-been-read, respond with something to show you’re on it.

On the Office Ladies podcast, Jenna Fisher and Angela Kinsey shared that their very different email styles caused friction when they began cohosting the podcast. Angela wouldn’t respond to an email until she completed the request, but Jenna didn’t know whether Angela had seen it, and it stressed her out. Angela then adapted her communication style to respond when she got it so Jenna wouldn’t be nervous.

Even if your response is, “Thanks for sending. I’ll dive in next week,” they know you saw it and that you’re on it.

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2. Do What You Said You Would Do

Reliability may be the most boring competitive advantage of all.

Show up and do the work. Meet your deadlines and come prepared to meetings.

A friend of mine recently considered hiring an agency for a very significant project.

She struggled to get them on the phone, though. They would set up the meeting and then cancel 10 minutes before it started. She was ready to pay them $100,000!

Finally, on the third reschedule, they didn’t cancel. Still, the agency sent a much more junior person who clearly hadn’t reviewed the materials or understood why the meeting was happening.

My friend politely suggested they reschedule once the person had a chance to prepare.

Still, she gave the benefit of the doubt. People make mistakes, and this wasn’t the main person anyway.

But then they also failed to take accountability. Instead of simply saying, “You’re right. We weren’t prepared for that conversation, and we should have been,” the response became defensive, immediately turning a recoverable situation into a reason not to trust them.

Many professional relationships can survive a mistake and ownership of it, but without accountability, there is no trust.

It turns out that this agency wasn’t competing against some major competitor with a revolutionary strategy.

They were competing against someone who would show up prepared.

Apparently, that’s a surprisingly high bar.

3. Care About People

Michael Scott in The Office isn't a great manager, but he is fantastic at sales. We see that when he lands a big client at Chili’s by being genuine and trying to connect with him.

We also see in the episode where Dwight steals his Rolodex that he remembers what people tell him. His Rolodex isn’t even particularly useful for other people because he basically only wrote down the things he shouldn’t say – green means “go ahead and shut up about it.”

Remembering small details about others, no matter how trivial, builds bonds. If someone tells you they’re nervous about a presentation next week, ask them how it went. If their kid was sick the last time you spoke, ask how the kid is doing.

At The Meet Group, our top-earning livestreamers were incredibly good at this.

They remembered what viewers had told them and took a genuine interest in the people who kept coming back.

That made viewers feel important and made them much more likely to care about (and gift) the streamer in return.

Even coaching streamers to do something as simple as saying “thanks” when they received gifts, and acknowledging their viewers when the feature first launched ten years ago, made a huge difference in how that streamer retained viewers and earned.

Caring about the person on the other side of the conversation is a pretty powerful advantage.

The Bar is Lower Than You Think

We tend to believe we need some magical differentiator to get ahead.

We need to become more charismatic, visionary, strategic, better networked, more innovative, etc.

And all of that stuff is important. But your biggest competitive advantage might not be the one thing you can do that nobody else can.

It might be doing all the little things everyone else knows they should do, but don’t.

Master the small stuff.

P.S. - I wasn’t able to record the last two weeks! I will link to those videos in an upcoming newsletter.

About Catherine Connelly:

Catherine Connelly is an entrepreneur, keynote speaker, and fractional leader. She co-founded myYearbook as a teenager and helped grow it into The Meet Group, a NASDAQ-listed social discovery and livestreaming company acquired for $500 million. Today, she is the author of Designing Success: Lessons from 20 Years as a Female Tech Entrepreneur, writes the weekly newsletter Growing Up Startup, and speaks about innovation, decision-making, and unconventional career paths.

There’s a bear in town.

Well, technically, there was a bear sighting in a neighboring town, but it’s close enough that it triggered a Nixle community alert text:

“Reported bear sighting near Canterbury Lane. Bear disappeared into the woods. Non-aggressive. Consult dep.nj.gov for more info on bears.”

Then came the text from some friends canceling an outdoor playdate because they were worried about the bear.

This struck me as a little silly, as presumably if we saw a bear we’d just go inside. Plus, it was non-aggressive. Perhaps we could change our playdate to a bear hunt. It made me second-guess my plans, though!

I had a seven-mile run planned for the next morning, some of it through wooded areas. Should I be worried about the bear? Should I change my route?

I had to remind myself: I probably won’t see the bear.

There are plenty of ways I could get hurt on a run that are way more likely, like getting hit by a car or tripping and wiping out, which I did 10 years ago and still have very scarred knees to show for it.

Those risks aren’t nearly as interesting as the bear. I don’t even think about them.

But they’re a lot more probable.

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Felt Risk vs. Probable Risk

People aren’t particularly good at assessing risk.

Some risks feel enormous because they’re vivid, unusual, or scary. We can picture them happening, or we’ve heard a horror story about someone who it happened to. For instance, I shudder thinking about Jimmy Fallon and his ring avulsion injury nearly every time I put on a ring.

Meanwhile, much more probable risks fade into the background precisely because they’re so ordinary.

The bear gets our attention.

The tick doesn’t.

We do the same thing in business.

One of my favorite examples is the founder who asks me for advice and then wants me to sign an NDA before they’ll tell me what they’re building.

There are horror stories, of course, of the founder whose idea was stolen and made into a billion dollar company which makes that risk especially salient.

But, it’s not particularly likely that the person you’re contacting for advice wants to drop everything, steal your idea, and dedicate themselves to it for the next five years. They have their own interests.

Some stories stick with us, but that doesn’t make them more probable. It just makes them memorable.

Of course startups have much bigger risks:

• Nobody wants the thing you’re building.

• Your go-to-market strategy is a mess.

• You don’t listen to your target market.

But “Startup fails because founders didn’t talk to enough customers” isn’t a particularly memorable story. It’s just how many companies die.

Rare events become stories because they’re rare and that contributes to a salience bias in which we misjudge and miscalculate risks.

How to Get Better at Judging Risks

In one of my classes at Wharton, we had to judge the likelihood of twenty or so random events, like would Apple’s stock be over a certain price, will we get over an inch of snow in Philly before Dec 1, and if a certain president would tweet over a certain number of times.

When we first saw the list of events we had to estimate probabilities for it was easy to have a gut reaction to some of them: this is obviously going to happen.

Then the research started. I realized things that I would have said this would “definitely” happen for, was actually maybe only 70% likely, which thoug is on the right side of maybe is certainly not the same thing as 100%.

I didn’t realize the actual probabilities of these events though without doing further research.

At TMG, we once went through a somewhat similar exercise where we listed the major risks facing the business, their probabilities, and what we could do to mitigate each one within each functional area.

Though it may seem difficult to carve out the time to do this exercise, it was actually pretty useful.

Because once you force yourself to articulate a risk and truly think about the probabilities, you can stop treating it as a vague, scary thing looming in the background.

Let’s say 90% of your new customers come from Facebook.

That’s a risk.

Now you can ask:

How likely is it that this channel becomes materially less effective?

What happens to the business if it does?

What warning signs would we see?

What can we do now to reduce our vulnerability?

Maybe the answer is diversifying acquisition channels. Maybe it’s investing more in organic growth. Maybe

it’s simply monitoring the risk for now.

The important part is that you’ve turned “What if Facebook stops working?” into something you can actually evaluate and prepare for. It’s now actionable.

You can do this across your business.

What happens if your biggest customer leaves? What happens if a competitor launches something similar? What happens if your costs increase? What happens if the fundraising environment changes?

As you do the exercise, ask three questions:

How likely is this?

How bad would it actually be?

What can I do now to reduce either the likelihood or the impact?

Sometimes you’ll realize the thing keeping you up at night really is a major risk, and you should do something about it.

Sometimes you’ll realize it would be unpleasant but manageable.

And sometimes you’ll realize you’ve been rearranging your life around a bear you’re probably never going to see.

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About Catherine Connelly:

Catherine Connelly is an entrepreneur, keynote speaker, and fractional leader. She co-founded myYearbook as a teenager and helped grow it into The Meet Group, a NASDAQ-listed social discovery and livestreaming company acquired for $500 million. Today, she is the author of Designing Success: Lessons from 20 Years as a Female Tech Entrepreneur, writes the weekly newsletter Growing Up Startup, and speaks about innovation, decision-making, and unconventional career paths.

My response was basically: You won’t feel confident until you start doing the work and making a plan.

We spend a lot of time talking about confidence as if it’s an internal state we can somehow summon. Believe in yourself. Trust your gut… just be more confident.

But people can’t just decide to feel confident about something they’ve never done before, and I’m not sure they should anyway.

Confidence needs backup.

It needs receipts.

My friend was considering doing something that would require a lot of preparation and research. But she hadn’t done much of that yet. She was frustrated that she couldn’t just trust herself to know she could do it.

I thought her lack of confidence made perfect sense.

Why should she be confident yet?

Instead of trying to convince herself that she could do it, she could start figuring out how she would do it: research, make a plan, talk to people who had done it before, or try some smaller version of it.

She didn’t need more confidence. She needed more evidence.

Confidence Is Often the Result, Not the Requirement

Years ago, when I applied to Wharton’s Executive MBA program, one of the application essay questions asked why I thought I could handle working while going to school.

I was pretty confident I could.

But not because I had unusually strong faith in myself.

I had receipts.

I was already a founder while attending high school full-time, and that continued while attending Georgetown full-time.

This would be the third time I’d balanced work and school, and unlike the first two times, this was a program specifically designed for people who were working.

I wasn’t thinking, Believe in yourself, Catherine! You can do anything!

I was thinking, I’ve literally done this twice.

That’s a very different kind of confidence.

One asks you to manufacture a feeling.

The other asks you to look at the evidence.

Similarly, when I was learning to perfect the backhandspring as a young gymnast, my coach, annoyed at me asking her to stand there “just in case,” didn’t tell me, “just be more confident” or “believe you can!”

She told me, “You have it, and you’re good at it.”

I didn’t need to summon confidence to do the skill, just muscle memory.

Start Collecting Receipts

The problem, of course, is that sometimes you don’t have the receipts yet.

You’re starting your first company, taking your first management job, giving your first big presentation, finding clients for your first time, or going off to college.

You may be trying something you have absolutely no evidence you’ll be good at.

That’s when people often think they need confidence most, but I think they need action.

You do something small, then something slightly harder. You learn, mess stuff up, and then recover. You try again.

And slowly, you accumulate evidence in the same way that you accumulate muscle in weight training or train for a race.

I’m a big believer in learning by doing. Every time you do something difficult or that pushes your comfort zone, you don’t just learn how to do that particular thing. You add another receipt to the pile.

I figured that out.

I handled that.

That went badly, and I recovered.

I didn’t know how to do this before, and now I do.

Eventually, those receipts become something more useful than confidence.

They become self-trust.

Your Receipts Are Transferable

The best part is that the evidence doesn’t have to match the challenge exactly.

I was once working with someone who was giving me a demo of a software platform I had never used. At one point, they were trying to find something.

“I think it’s over there,” I said, pointing to part of the screen.

They found it.

“Oh, have you used this before?”

Nope.

I’d just used a lot of dashboards.

I didn’t know where that particular button was. But I’d seen enough similar products to have a pretty good guess about how this one probably worked.

The same thing happens with much bigger challenges.

You may never have started a company before, but maybe you’ve built something from scratch.

You may never have managed a team, but maybe you’ve gotten a group of people aligned around something difficult.

You may never have made this particular hard decision, but you’ve made other hard decisions and lived with the consequences.

The receipt doesn’t always say:

I’ve done this before.

Sometimes it says:

I’ve figured things out before.

That’s an incredibly valuable receipt to have.

Record the Evidence

The problem is that we’re often terrible at remembering our own receipts.

The failures stick.

The awkward presentation. The project that bombed. The job we didn’t get. The thing we wish we’d handled differently.

Meanwhile, the hundreds of things that went fine disappear almost immediately.

You need to record them.

Recording it may look like keeping the nice email someone sent you or writing down the problem you solved that you initially had no idea how to solve. Remember the project you thought would overwhelm you until it didn’t. Look back at your old emails or old journals and remember how far you’ve come.

We don’t need to convince ourselves that we’re amazing at everything.

None of us are, but we can develop calibrated confidence.

We want our belief in ourselves to be grounded in what we actually know, what we’ve actually done, and what we’ve demonstrated we can figure out.

Do Hard Things

I think about self-trust with running. When I line up for a half marathon, I have a baseline trust. The distance doesn’t scare me as I’ve done that distance quite a bit.

My next race won’t be easy. I plan to push the pace. The weather could be terrible, or I could have a bad day, but I know what 13.1 miles feels like.

I know the course and that mile 10 is hilly, but I’ve kept going before, so I’ll do it again.

I have the receipt.

Every time we do something hard, we collect another one even if the hard thing isn’t even directly related.

Confidence shouldn’t be an unquestioning belief that everything will work out, but rather that when you don’t know what to do, you’re capable of figuring it out.

So the next time you find yourself wishing you were more confident, don’t spend too much time trying to feel differently.

Ask yourself what evidence would make you more confident.

Then go collect it.

Action creates evidence. Evidence creates confidence.

Keep the receipts.

P.S. If you’re building a business and could use another set of eyes as you figure out what to do next, Gabrielle Hailmann and I are opening applications for a small pilot program this fall for 10 women entrepreneurs. We’ll help you step back, get clear on your priorities, and build a practical roadmap for moving forward. Learn more here!

About Catherine Connelly:

Catherine Connelly is an entrepreneur, keynote speaker, and fractional leader. She co-founded myYearbook as a teenager and helped grow it into The Meet Group, a NASDAQ-listed social discovery and livestreaming company acquired for $500 million. Today, she is the author of Designing Success: Lessons from 20 Years as a Female Tech Entrepreneur, writes the weekly newsletter Growing Up Startup, and speaks about innovation, decision-making, and unconventional career paths.

“The wolf that one hears is worse than the orc that one fears.”

“True! But where the warg howls, there also the orc prowls.”

- The Fellowship of the Ring

It probably comes as no surprise that I’m a Lord of the Rings fan; after all, the very first slogan for myYearbook was “one yearbook to rule them all.” (By launch, it had changed to “You’ve Got Friends,” which is dorky in a different way.)

As it turns out, this exchange between Boromir and Aragorn also contains surprisingly good advice for founders. As founders, it’s easy to get pulled between the wolf in front of us and the orc we fear in the distance. Aragorn’s response reminds us that they’re connected. The immediate problem deserves our attention, but it can also reveal something about the larger challenge ahead.

As humans, we tend to catastrophize. We imagine future scenarios that hang over us:

• What if my client doesn’t need me next year?

• What if Apple changes its policies?

• What if this competitor crushes us in two years?

• What if we run out of money next year?

While we’re busy worrying about those possibilities, today’s problems don’t stop demanding our attention.

• An email from an unhappy customer

• A landing page with poor conversion

• A proposal you need to send out

• An outreach list you haven’t touched

• A hire that should have been made yesterday.

When building anything big, it’s easy to be distracted from the immediate problem by a distant uncertainty.

The challenge is that many future threats aren’t actionable yet. One of the best things a founder can do is ask: “What wolf can I solve today that prepares me for the orc I fear tomorrow?”

Are customers bored with your product? That’s a wolf, and solving it makes it harder for competitors to beat you. Is your sales pipeline thin? That’s a wolf, and fixing it reduces the chance you’ll run out of money. Are users abandoning onboarding? That’s a wolf, and improving it strengthens your business no matter what the future holds.

As we built myYearbook/MeetMe/The Meet Group, we were always aware of the future threats: new apps, algorithm changes, App Store changes, etc. And though we stayed apprised of them and they impacted our strategy, our day-to-day attention went to blocking and tackling the current problem and executing on our pipeline. Solving today’s problems is often the best preparation for tomorrow’s.

The lesson isn’t that founders shouldn’t think about the future. It’s that attention is finite.

As a founder, every minute you spend obsessing over the orcs (the future problems) is a minute that you’re not spending on the wolves (the existing threat).

The orcs are still an important problem, but if you don’t focus on the wolves, there won’t be a company left for the orcs to attack in the uncertain future.

Here is what has generally helped me with dealing with certain and uncertain problems:

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Identify what problems are wolves and which are orcs.

Which of your fears are so ambiguous or distant that there isn’t a clear, actionable step you can take towards attacking them? Those are your orcs. Recognize them.

Group and prioritize the issues

Ask yourself which wolves are merely urgent and which ones also reduce future risk. Prioritize the latter whenever you can.

Set aside time to think strategically.

Seriously.

As y’all know, I’m a big fan of timeboxing. Timeboxing can be your friend for managing uncertainty because it means that when the existential threat pops into your head at 3 am, you can write it down and know you’ll deal with it later.

You could set up your time budget to include dedicated strategy time to identify the wolves that will best prepare you for the orcs you fear. For instance, “What if our Meta ads stop working?” feels like an orc, but you can reframe it into a concrete problem you can actually work on today: “How can I diversify acquisition channels so we’re less dependent on Meta?”

You won’t be able to turn every orc into a wolf, but this reframe will keep you from being stuck in a cycle of worrying when you could be preparing.

Founders can’t ignore the orcs. Strategy matters. Preparing for the future matters. That often means making the murky future more actionable.

Businesses aren’t usually won or lost because someone worried harder about tomorrow. They’re won by founders who keep showing up to solve today’s wolves, one after another, while keeping an eye on the orcs.

There will always be another orc on the horizon. Until then, keep your attention on the wolves you can hear.

P.S. If you're trying to figure out which "wolves" deserve your attention in your own business, Gabrielle Hailmann and I are opening applications for a small pilot program this fall for 10 women entrepreneurs. We'd love to help you gain clarity and momentum. Learn more here!

About Catherine Connelly:

Catherine Connelly is an entrepreneur, keynote speaker, and fractional leader. She co-founded myYearbook as a teenager and helped grow it into The Meet Group, a NASDAQ-listed social discovery and livestreaming company acquired for $500 million. Today, she is the author of Designing Success: Lessons from 20 Years as a Female Tech Entrepreneur, writes the weekly newsletter Growing Up Startup, and speaks about innovation, decision-making, and unconventional career paths.

Yep.

No wonder I was drawn to a book called Don’t Be Yourself.

Of course, I think authenticity has its place. During revisions for my book I became more precise about the situations in which we should be more authentic, what we need to do first, and who has earned the right to see our more vulnerable sides.

But vulnerability can be risky, and a lot of the popular advice about authenticity seems less authentic than unprofessional.

Authenticity isn’t about removing your filter. It’s about intentionally deciding which parts of yourself belong in which settings.

As has said, “Authenticity is not about saying whatever pops into your head. It’s about sharing who you want to be. Healthy self-expression doesn’t mean no filter. It involves weighing whether your current thoughts and emotions are aligned with your lasting values.”

In Don’t Be Yourself, Tomas Chamorro-Premuzic makes a related argument: It is often kinder to others to present your best self, or at least your most professional self.

Why should your direct reports have to deal with you being a hot mess just because sometimes you are?

We love that Taylor Swift can “do it with a broken heart.” We also generally expect professionals to act professionally, whether or not that reflects how they feel on a particular day.

I had an amazing call recently.

The woman and I vibed instantly. We were both animated and engaged, and we’re going to work together.

The thing is, I was having an awful day.

She had no idea.

That was the point.

Channeling my inner Swift, I chose not to bring my awful day into the conversation. Then, after the call, it no longer felt quite so awful. The conversation had been so much fun that my mood genuinely improved.

I wasn’t being fake. I was choosing which version of myself belonged in that interaction.

In most of our day-to-day interactions, having a filter is helpful.

As I wrote last week, if work doesn’t have to be your entire identity, your entire identity also doesn’t have to show up at work.

We are the same people in different settings, but different aspects of us take center stage. You are probably not exactly the same person at a neighborhood bar, a family dinner, and a board meeting. That doesn’t make any of those versions dishonest.

It means you understand context.

There is also a more serious problem with blanket advice to “bring your whole self to work”: We do not all have the same ability to be authentic in every situation.

As Jodi-Ann Burey has shared, “Being authentic privileges those who are already part of the dominant culture. Being who you are is much easier when who you are is all around you.”

The more status or power you have, the more “yourself” you can usually afford to be. That means leaders have a greater responsibility to create environments where other people feel comfortable, supported, and like they belong.

My grandma used to tell my mom never to call out of work because the kids were sick. She said to always say that she was the one who was sick, rather than draw attention to that vulnerability.

What my grandma understood was that women were less common in the workplace and were already seen as “other.” Drawing attention to the demands of motherhood could have bigger career ramifications.

Thankfully, many workplaces have changed.

In 2026, most of us no longer need to lie about which member of the family is sick. Many workplaces have more understanding for childhood illnesses or the need for a parent to attend a school play.

A leader who openly says, “I have a sick kid at home,” can make it easier for people on the team to be honest about their own caregiving responsibilities. They may even bond over the shared horrors of norovirus.

That is an example of authenticity being useful. The leader has enough status to take the first risk, and their disclosure creates more safety for someone else.

It feels better to be yourself than to feel as though you are hiding a huge part of your identity. But we still need to be thoughtful about how, when, and with whom we open up.

I think about authenticity in three steps.

Assess

First, assess the situation.

Know the room you are sharing in and the person you are sharing with. Can you trust them? Have they shown that they will handle what you tell them with care?

One study found that 73% of people had experienced authenticity or vulnerability backfiring at work. The problems were often related to poor self-awareness, misjudging the other person, or operating in a toxic work environment.

If you are in a toxic environment, you should of course consider leaving. But while you are looking for a new role, you do not owe that workplace more information it can use to cause further harm.

Protecting yourself is not dishonesty.

Ready Yourself

Before you share a vulnerable part of your story, make sure you are ready to tell it.

My friend Charreah K. Jackson has shared that she couldn’t immediately be open about her experience as a cancer survivor. She was afraid that people would see her as weak.

First, she had to put in the work to take ownership of her story. She needed to reach a place where she saw herself not as weak, but as the warrior she is.

If you are still deeply uncomfortable with a part of your story, you may not yet be ready for other people’s reactions to it.

You get to wait.

Reframe

Finally, tell your story in a way that showcases your strength.

Say, for instance, that you followed a nontraditional path into leadership and feel embarrassed by it.

You could hide your background, but that may backfire if people interpret your discomfort as shame or distance.

You could present it only as a hardship, but if you tell the story in a way that suggests you do not believe you belong at the table, others may reach the same conclusion.

Or you can reframe it.

Perhaps your background made you more resilient. Perhaps it gave you an unconventional idea or helped you see a customer, problem, or opportunity differently.

When sharing what makes you unique, connect it to why it is relevant. Show how it became an advantage, or perhaps even a hidden superpower, in your new setting.

Authenticity is not saying everything you think, sharing everything you feel, or giving everyone access to every part of you.

It is not living without a filter.

It is knowing yourself well enough to decide what to share, trusting yourself enough to wait when you are not ready, and understanding the room well enough to know when your story might help someone else feel safe enough to share theirs.

Sometimes the most authentic thing you can do is present the best version of yourself.

That version is still you.

During one of our one-on-ones, I asked where she wanted her career to go.

Did she want to manage people someday? Own a bigger piece of the business? Become an expert in a particular area?

She paused and said something along the lines of, “I just want to do this job.”

That was it.

At the time, I couldn’t understand her answer.

I had spent my entire career surrounded by entrepreneurs and ambitious startup employees. Everyone seemed to be chasing something: a promotion, a bigger team, more responsibility, the next challenge.

I assumed that was what everyone wanted.

Pew research shows that people are remarkably split on how central work is to their identity. Though 39% people view it as extremely or very important piece, a third only thinks it’s somewhat important, and nearly a third don’t see it as an important part of who they are at all.

For many people, work is how they support their families. It pays for vacations. It funds hobbies. It creates stability.

The employee who puzzled me spent much of her time outside of work volunteering. Her job mattered, but it wasn’t the most meaningful part of her life.

There was absolutely nothing wrong with that. And yet we put an incredible amount of pressure on our careers.

Your work should be your passion. You should find purpose and meaning in it. It should define your identity and be your calling.

That’s asking one part of your life to do an awful lot.

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Tomas Chamorro-Premuzic in Don’t Be Yourself writes, “The pressure to connect emotionally and psychologically with your job can actually increase feelings of guilt, shame, and self-criticism when that connection never materializes.”

In other words, expecting work to fulfill every emotional need may leave us more dissatisfied with perfectly good jobs.

Whenever I hear college students or young professionals worrying that they haven’t found “the thing” they’re passionate about, I wonder whether we’ve accidentally set the bar impossibly high.

Sometimes a job is just...a job.

That doesn’t mean it’s a bad job.

It doesn’t mean you’ve settled.

It doesn’t mean you’re wasting your life.

It simply means you’re getting something different from it than someone else might.

Think about The Devil Wears Prada. Andy doesn’t take that job because she dreams of fetching coffee and tracking down unpublished Harry Potter manuscripts. She takes it because it opens doors. It’s a stepping stone.

Not every season of work has to be deeply fulfilling.

Similarly, I doubt corporate lawyers genuinely love spending hours reviewing contracts and documents. The work can still provide an intellectually challenging career, financial security, incredible colleagues, and opportunities that make the less glamorous parts worthwhile.

That’s enough.

We don’t need to pretend every task we perform is overflowing with purpose.

Every career and every role has less exciting stretches, even careers you love.

Purpose doesn’t have to come from work.

It can come from raising children, practicing your faith, running half marathons, volunteering, traveling, painting, coaching Little League, writing, or building relationships with the people around you.

Work is only one part of a meaningful life. Somehow we’ve started acting as though it should be responsible for all of it.

That doesn’t just make it harder to feel satisfied with our jobs. It may also make us less resilient.

When your identity is completely wrapped up in your career, a layoff isn’t just the loss of a paycheck. It can feel like the loss of who you believe yourself to be.

A promotion becomes validation. A rejection becomes personal. A company restructuring becomes an identity crisis.

When your life is built on more than your job, work still matters. It just doesn’t get to determine your worth.

That seems healthier.

If you have a job that pays your bills, treats you well, keeps you learning, and gives you the freedom to build a life you love outside the office, you aren’t doing work wrong because you’re not passionately in love with it.

Sometimes your job is just your job.

And sometimes that’s exactly enough.

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About Catherine Connelly:

Catherine Connelly is an entrepreneur, keynote speaker, and fractional leader. She co-founded myYearbook as a teenager and helped grow it into The Meet Group, a NASDAQ-listed social discovery and livestreaming company acquired for $500 million. Today, she is the author of Designing Success: Lessons from 20 Years as a Female Tech Entrepreneur, writes the weekly newsletter Growing Up Startup, and speaks about innovation, decision-making, and unconventional career paths.

That’s the thing about startups. The jobs change.

The best team members evolve with them.

Watching careers evolve has made me think differently about excellence.

In sports, we admire athletes who can compete in multiple arenas. Michael Jordan went from playing basketball to playing well in minor league baseball and golfing with a low single-digit handicap, which makes him a top amateur player.

The skills that made him a basketball legend also transfer to other sports. Of course, he’s an extraordinary athlete, but what was transferred wasn’t basketball. It was his ability to learn, practice, compete, and improve.

He has transferable excellence.

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We need transferable excellence in business, too.

I think about this when people ask me how to hire the “right” people (and the natural corollary, how they can increase their chances of being considered).

Many careers don’t follow a linear path – startups are especially nonlinear. How do you find the people who can adapt?

When you are building a company, especially early on, roles evolve constantly. The thing you desperately need someone to do today may not even matter later.

When we started myYearbook, we didn’t know what jobs we’d need a year later.

Our accountant ended up doing business development and later joined the engineering team. Another person, originally hired for business development, shifted to product. A project manager shifted to being the main integrator between teams when we acquired another company, and again shifted to run an entire new area of the company as our needs shifted.

They evolved with the company.

Though specialization can make you great at what you do, it’s rigid—expertise matters, but so do skills that travel.

Skills such as communication, relationship-building, quick learning, project management, resilience, and pattern recognition will make you a good hire no matter the role.

The best team members I have worked with were not people who stayed neatly inside their original job descriptions. Instead, they were the people who naturally expanded beyond them and adapted to the changing needs as we built.

They were the people who would see a problem and move to fix it. They weren’t waiting for permission.

They were paying attention to what actually needed to happen.

That mindset matters because startups reward people who pay attention to what actually needs to happen, not just what was written in the original hiring document six months earlier.

My own career uses transferable skills all the time. Running millions of dollars in marketing spend every month made me quite organized and good at developing processes and rules that impact other areas of my life. Needing to promote myYearbook to the press as a teenager made me a confident, comfortable professional speaker later on. They’re not the same jobs, but the underlying skills are similar.

As AI reshapes work, I think this becomes even more important to every career, startup or not. We genuinely do not know what many jobs will look like in the future. The people best positioned are those who know how to learn, can spot patterns, and make connections.

The companies that thrive won’t just be built by people with deep expertise. They’ll be built by people whose expertise travels.

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P.S. - I launched my “perks” page which has info for booking a 1:1 call. 😃

About Catherine Connelly:

Catherine Connelly is an entrepreneur, keynote speaker, and author of Designing Success: Lessons from 20 Years as a Female Tech Entrepreneur. She co-founded myYearbook as a teenager and helped grow it into The Meet Group, a NASDAQ-listed social discovery and livestreaming company acquired for $500 million. Today, she writes the weekly newsletter Growing Up Startup and speaks about innovation, decision-making, and unconventional career paths.

Here is the video from last week that I couldn’t film while we were away:

One thing I’ve been trying to do more of this year is run little experiments.

Not huge life overhauls. Just tiny changes to see what happens.

Some failed. Others have quietly (well... significantly!) changed how I work, read, run, and spend my time.

Here are five that have stuck. I hope one of them will be worth trying yourself.

1. Starting the next book within a few days of the last book

My reading has skyrocketed this year. I’ve read 28 books this year so far, and I may already be done with 29 and 30 by the end of this week.

I’ve never tracked how many books I’ve read in previous years, but it’s probably around 12-15.

So, how am I on course to more than double my typical reading?

I have a new rule: I start the next book within three days of finishing the last one.

Typically, when I read, I get into a story, but when it ends, I lose momentum. This year, I’ve kept the momentum going by having a plan for what the next book on deck is and starting it.

Three other things that have greatly increased my reading this year:

• Audiobooks: As I’ve shared before, they count as reading 🙂 46% of this year’s books have been audiobooks.

• Libby: I get so many books on Libby. This also helps me finish books quickly, as I have to return them. 60% of this year’s books have been from Libby.

• Reading more fiction: I went through a really strong non-fiction phase, but this year at least I’ve read 80% fiction. Now, quite a few on my to-be-read list are non-fiction, so we’ll see how this ends up, but I’ve rediscovered my love of being in another world – even non-Wizarding worlds!

So, if you want to read more books, try to keep the momentum going by setting a deadline to start the next one. Or, apply this to any other habit you’re trying to cultivate and start making progress on the next part before you lose your momentum.

Also, please let me know what you’re reading! I need recommendations.

2. Bricking my phone

This is the newest experiment on the list, but it’s already making a noticeable difference. My husband bought the Brick device last month. Basically, when you put your phone in Brick mode, you can’t bypass it until you scan the Brick with your phone.

So now, if an app is locked, I have to go downstairs and open a cabinet to access it, instead of just entering my Screen Time password to bypass the lock.

I mentioned before that one of the main issues with using my phone is that I read stuff in the morning, start the day reactively, and delay my workout. Now, at 10 pm, my phone locks most of my apps, and they are still locked in the morning.

I’ve already seen it reduce my screen time, particularly in the morning and at night, when my willpower is at its lowest.

3. Closing all my tabs when I’m done for the day.

I’m the person who usually has a ridiculous number of tabs/windows open, but I’ve noticed it’s making my morning go back into react mode. Every morning, I was essentially opening yesterday’s unfinished thoughts.

If I had had LinkedIn or Gmail open, I would have started perusing that rather than what I was supposed to be doing to start my day. I’ve mentioned before that I’m a big believer in timeboxing, but I was making it hard not to get distracted immediately.

So, now when I am done working, I close all the tabs I have open so I can start the day with a blank slate.

Closing everything gives me permission to start fresh.

It’s been nice.

4. Following dedicated training plans

I wrote a lot about my recent 5K training plan, and now I’m doing a half-marathon one.

Both plans have been more challenging than I would have created for myself, but they also include a good mix of workouts that keep things interesting.

Most importantly, they’re another way of reducing the need for willpower. I don’t have to decide what kind of run to do or whether I’m pushing myself enough. I simply look at the plan, lace up my shoes, and do the workout.

My enthusiasm for running has never been stronger, and I don’t have to spend any mental energy planning the run. I just execute.

5. Face washing

Six months ago, I would have been deeply skeptical that “wash your face” would end up on a list of things that changed my year.

There was a whole post about this one recently, but the tldr: big results can come from small, seemingly unrelated changes – like finally starting a skincare routine.

Looking back, none of these experiments were life-changing on their own.

What they all did was remove friction.

Instead of relying on motivation, they made the next right action obvious.

Start the next book. Follow the plan. Close the tabs. Leave the phone locked. Wash your face.

Tiny changes. Much less friction.

See you next week 🙂

About Catherine Connelly:

Catherine Connelly is an entrepreneur, keynote speaker, and author of Designing Success: Lessons from 20 Years as a Female Tech Entrepreneur. She co-founded myYearbook as a teenager and helped grow it into The Meet Group, a NASDAQ-listed social discovery and livestreaming company acquired for $500 million. Today, she writes the weekly newsletter Growing Up Startup and speaks about innovation, decision-making, and unconventional career paths.

I’ve never really understood vision boards.

When I was writing my book, my publisher encouraged me to make one. I did... sort of. I arranged some images on a board, stared at it, and checked it off my to-dos while wondering why everyone seemed so inspired by this exercise.

I assumed I was just doing it wrong.

Then I read something by that finally clicked.

In Beyond Belief, he writes about research suggesting that vividly imagining achieving a goal can sometimes reduce the motivation to pursue it. If your brain spends enough time enjoying the feeling of success, it can start acting as though you’ve already made meaningful progress.

That explained a lot.

I’m not against visualization. I’m against stopping there.

Last week, I was listening to the Nobody Asked Us podcast. Kara Goucher and Des Linden were interviewing Dakotah Popehn before Grandma’s Marathon. Popehn, who wants to win the race the most times ever, was going for her third win.

Dakotah shared something that stuck with me.

When you’re two or three miles from the finish of a marathon, that’s too early to picture yourself breaking the tape or standing on the podium.

Instead, you focus on the next mile.

The next stop sign.

The next turn.

The next step.

Because the race isn’t over yet.

Of course, plenty of elite athletes talk about visualizing success. That’s not inconsistent. It’s about the timing. The visualization happens before the race, not instead of the race. Once the gun goes off, they’re not imagining the medal ceremony. They’re thinking about their pace, their breathing, and the runner in front of them (or behind them).

It reminded me of all those viral videos of athletes celebrating just before the finish line, only to have someone sprint past them in the final seconds.

You don’t win until you win.

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I’ve seen this outside of sports, too.

Years ago, we were working toward selling our company. Everyone expected the deal to happen.

Then it fell apart overnight because of a CFIUS decision related to an entirely different deal and company.

Another time, we were sure Lehman Ventures would give us a term sheet. It had all been discussed, and we were just waiting on the final in-writing piece.

Until it wasn’t, the term sheet never came. (By the way, this was the summer of 2008 - yikes!)

Eventually, another investor led the round, but it was a reminder that a verbal yes isn’t money in the bank.

Even our eventual acquisition wasn’t “done” when it was announced. We announced the $500 million transaction a week before the COVID lockdowns began. For months, there was uncertainty as regulators reviewed the deal, and the world around us changed dramatically before it closed.

I’ve also watched companies begin acting like a merger was complete before it officially closed. Teams started integrating. Plans were made. People assumed it was inevitable.

Sometimes it is.

Sometimes it isn’t.

Nothing is final until it’s final.

I think that’s why vision boards have never resonated with me.

I’ve found I’m most motivated when I stay focused on the work instead of the outcome.

I can absolutely imagine where I want to go. I have big dreams.

They’ve guided plenty of major decisions in my life. But dreams aren’t the work. The work is the work. And you don’t win until you win.

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About Catherine Connelly:

Catherine Connelly is an entrepreneur, keynote speaker, and author of Designing Success: Lessons from 20 Years as a Female Tech Entrepreneur. She co-founded myYearbook as a teenager and helped grow it into The Meet Group, a NASDAQ-listed social discovery and livestreaming company acquired for $500 million. Today, she writes the weekly newsletter Growing Up Startup and speaks about innovation, decision-making, and unconventional career paths.

The question always struck me as strange.

At the time, one of my high school friends was running for mayor. One of my best friends was graduating summa cum laude and getting accepted into every law school she applied to.

I remember answering something along the lines of:

“No, all my friends are doing cool things. We’re just doing different cool things.”

One of the greatest sources of motivation in my life has been watching my friends succeed.

I have also experienced the opposite. De-motivating comments from classmates and friends meant to wound or make me feel smaller.

When I was in high school, there was a boy who mocked the way I looked in my CNBC interview.

Another classmate insisted I must be tampering with the voting on myYearbook because there was no way that many people would vote for me.

Another “friend” thought less of me for not going to an Ivy League school.

I chalked it up to some form of jealousy and thought maybe that was normal and to be expected. After all, in Friends, before Monica gets engaged, Rachel says she’s “98% happy and maybe 2% jealous.”

Phoebe says she’s “90/10.” And, Rachel amends to 90/10 as well.

And, we know comparison is the thief of joy. Is the natural assumption then that when you do big things, the people in your life can’t be fully supportive?

No, it isn’t.

Sometimes another person’s success briefly makes us think about our own goals or self-assess. That’s normal.

But just as the Friends episode ends and the engagement is official, Rachel and Phoebe, true friends, are completely happy for Monica and not a bit jealous.

That’s the type of friendships I aim to cultivate, and the ones I’ve been blessed to have.

They’re wingpeople.

People who cheer loudly, celebrate wins, make introductions, share opportunities, and remind you that ambitious goals are possible.

And over the years, I’ve realized just how much those people matter.

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In the last few weeks, some friends have done amazing things:

Rebecca Bennett won the New Jersey 7 Democratic primary after running a phenomenal campaign. The general election this November will be one of the most closely watched and competitive contests in the country.

Jessie Chiang was named Banking & Finance Lawyer of the Year at this year’s Euromoney Women in Business Law Americas Awards.

Tiffany Xingyu Wang’s forthcoming book, The Trust Code, reached #1 New Release and bestseller status on Amazon with pre-orders alone. Between AI doomsday and AI utopia, she charts a practical path forward, exploring how to trust AI wisely.

Jaclyn Gullett launched Licci & Gullett Accounting with her friend Susie after fifteen years as a CPA in healthcare and at Deloitte to help small business owners with their bookkeeping.

They’re all in different industries and have different goals and definitions of success.

The common thread is that every one of them dared to put themselves out there.

I may not want their job or their exact outcome, but every time someone I know takes a big swing, it reminds me that big swings are possible.

Seeing people do ambitious things is motivating.

The morning Jaclyn announced her business launch, I had slept terribly and was generally in a bad mood. Seeing her post that it was “official” instantly made my morning better.

I love seeing my friends do cool things.

Their success makes me feel like more is possible.

My friend’s achievements remind me that ambitious goals are achievable when someone is willing to pursue them, even if I never want to be a congresswoman, lawyer, or bookkeeper.

They normalize trying and taking shots on goal. And, because I got to see how hard they worked and the journey they took to get to this point in their careers, I also get to see the struggle and what they were up against and beat.

That’s powerful.

Over the last few years, I’ve been trying to become much more intentional about cultivating wingpeople in my life.

While writing my book, I formed a group with other authors.

As I’ve pursued speaking, I’ve joined speaking communities.

In these groups, we share opportunities, celebrate wins, offer feedback, make introductions, and cheer each other on.

The result is that success starts feeling less like a competition and more like a team sport. It’s abundance in practice.

So if you’re feeling stuck, uninspired, or lacking motivation, here are three things I’d suggest:

Celebrate someone else.

Take a friend to dinner. Send the congratulatory text. Buy the book. Share the launch announcement. Cheer loudly.

Join communities where people are building things.

It doesn’t have to be your industry. In fact, sometimes it’s better if it isn’t. Surround yourself with people who are creating, launching, leading, and trying ambitious things. It’s contagious.

Be a wingperson.

Make the introduction. Leave the recommendation. Share the opportunity. Support someone else’s goal.

Cheering for others can make you more invested in your own goals.

Create friendtors by surrounding yourself with people who work hard and have big goals.

Not because they’re successful, but because they’re willing to try.

Surrounding ourselves with the right people won’t make us feel smaller.

It will make our world feel bigger.

P.S.- If you are a small business owner in need of a bookkeeper so you can focus on the areas of your business where you create the most value, check out Jaclyn’s company here!

About Catherine Connelly:

Catherine Connelly is an entrepreneur, keynote speaker, and author of Designing Success: Lessons from 20 Years as a Female Tech Entrepreneur. She co-founded myYearbook as a teenager and helped grow it into The Meet Group, a NASDAQ-listed social discovery and livestreaming company acquired for $500 million. Today, she writes the weekly newsletter Growing Up Startup and speaks about innovation, decision-making, and unconventional career paths.

Last weekend I completed one of them.

36-year-old Cat beat 23-year-old Cat’s 5K record.

Naturally, this prompted me to immediately start evaluating all my other goals.

Looking back, the running goal had three things going for it:

The Goal

Without a goal, my 5K time wouldn’t have drastically improved. Putting my goal out there helped to hold me accountable.

Scaffolding / a Plan

The goal is one thing, but I needed to plot how to get to that point. I started by having ChatGPT create running plans for me, with instructions to include an interval, tempo run, and easy run each week, with a maximum total running time of 30 minutes.

I did improve. But then, during my time-trial 5K, I noticed a major issue: I didn’t have the endurance to run at race pace for the entire three miles. My sycophantic chatbot listened to the parameters I gave it and adjusted my plan to fit into my existing schedule. Unfortunately, my fitness level didn’t care about my schedule constraints.

I decided to try out Runna. Runna did not listen to me when I told it I wanted my longest run to be no more than 4 miles (it was, in fact, 7.5 miles). It was the challenge and structure I needed, though.

You can’t get better by doing the same things that aren’t working.

Doing the reps

It’s one thing to have the plan, but I actually followed it. I hit all my goal paces in every training run. Despite the perceived excessiveness of a 7.5-mile run to run 3.1 miles (wtf Runna?!), I trusted the process and set my alarm for 5 am to get those miles in.

As I said earlier, it’s about doing the right reps.

Now, how does this framework apply to my other goals? After all, running is straightforward. You train. You race. You get a result.

Most goals aren’t like that.

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Speaking goal

My goal was a dozen speaking engagements. I’ve done six and am confirmed for another three in the fall and potentially two summer gigs as well. I still need to keep pushing, but I am roughly on track for the measurable part of this goal.

The speaking goal is much harder than the running goal, though. Unlike running, there isn’t really a prescribed process. I can refine the process, but I can’t simply plug my last few gigs into a Runna-type app for speakers to get a straightforward plan.

Running is a machine. You put in the training, you get results.

Speaking is like gardening. You plant a seed and nurture relationships, and see what grows. Some things sprout quickly, while others may take years to come into fruition.

Opportunities beget opportunities.

There is also luck. Hard work isn’t enough. Did you reach out to the organizer at the right time? Do they care about your topic this year? Did you hear about the opportunity? At an event I’m speaking at in November, I submitted my proposal back in January and was selected from the over 1,000 submissions. I think my session is good and should be selected, of course, but I assume there were plenty of great talks that were rejected, too.

This type of goal lacks control. It’s similar to when we were building TMG’s B2B business. There was often a long period of relationship-building before we partnered. There were times no one responded to our emails for months, and then BAM! The partner was ready, and they moved fast.

It’s also harder to control motivation.

Unlike a 7-week 5K training plan, conferences are planned months in advance. When I spoke at SXSW, I’d have to submit my topic by the summer for a March conference. This huge gap in effort and payoff makes motivation much harder.

There is also a lot more fear involved. I know I need to be better about reaching out – but I’m also afraid of the rejection. I keep reminding myself that I need to reframe success as the shots on goal, not just the final score.

The hidden magic of the speaking goal, though, has been in the new community I’ve found myself a part of. I joined Steve Fredlund’s Ambitious Speaking Collective, my local chamber of commerce, and have made so many speaking friends and cheerleaders. I am so grateful to the community in this industry. Even if there were no gigs on the horizon, meeting these fabulous people would make the effort worthwhile!

To improve my speaking, I largely lack scaffolding. That is where my effort will go, but I will also be enjoying this journey with the cool people I’ve met along the way.

Speaking wasn’t the only goal that surprised me, though.

Family

My goal was to enjoy the season, and I am. The challenge with this goal is that success is bittersweet. My daughter will soon start a full-day program (meaning until 2:45). How did we get here already? My kids are still babies!

One of my favorite parts of the day, though, is when I get back from my morning workout, and I see my kids waiting for me, peeking out from the top of the stairs. Even better, now they also get ready by themselves. This is a nice new phase.

Community
I set a goal to call my friends more. I’ve done it a few times, which is better than zero. I have gotten better at texting friends. The specificity of this goal wasn’t great. I am hereby amending my goal to talk to a friend on the phone at least once a month.

While my friendship’s goals were harder to measure, I’ve expanded my community through the professional orgs I mentioned above, by being active in my daughter’s school, and in my role as co-chair of the Wharton Executive MBA Women’s group.

Moving Forward

What I’ve learned in this check-in is that the area where I feel like I’m doing best is because I did all the things: set a clear goal, developed a plan, and did the reps.

Without the plan, motivation faded. There was confusion.

But what I also learned was that not every goal works the same way.

The running goal benefited from more structure. The clearer the goal and the plan, the better the result.

The speaking goal taught me almost the opposite lesson.

Yes, I need better scaffolding. I need to follow up more consistently. I need to create more opportunities for myself.

But some of the best parts of the goal weren’t things I planned.

I didn’t set out to meet a community of speakers. I didn’t set out to find new cheerleaders and friends. I certainly didn’t put “have fascinating conversations with interesting people” on my goals spreadsheet.

Those things happened because I left enough room for them to happen.

With any goal, it’s important to have a clear objective, a plan, and the willingness to do the work. But it’s just as important to leave a little space for serendipity.

Looking back, I think my mistake was assuming all goals were machines.

Set a target. Build a plan. Do the work. Get the result.

Some goals work that way.

Others are gardens.

They still need attention and effort, but they also require patience, relationships, and a willingness to see what grows.

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About Catherine Connelly:

Catherine Connelly is an entrepreneur, keynote speaker, and author of Designing Success: Lessons from 20 Years as a Female Tech Entrepreneur. She co-founded myYearbook as a teenager and helped grow it into The Meet Group, a NASDAQ-listed social discovery and livestreaming company acquired for $500 million. Today, she writes the weekly newsletter Growing Up Startup and speaks about innovation, decision-making, and unconventional career paths.

This is not the season when the most work gets done, and that’s okay.

Many productivity experts talk about this idea. Kendra Adachi often encourages people to plan for the season they’re actually in rather than the season they wish they were in. Others intentionally structure their year around periods of intense work followed by periods of recovery.

I’m feeling that shift right now.

A few years ago, this transition would stress me out. I’d feel pressure to make summer magical while also trying to maintain my normal routines and productivity.

Now I try to plan for it instead.

The kids are going to be home.

We’re going on vacation.

My schedule is going to look different.

June will not be my most productive month, at least not if I measure productivity by my work to-do list.

And that’s okay.

Accepting the season, though, doesn’t mean giving up on structure.

I still approach summer with the same over-prepared ridiculousness I bring to everything else.

While some people embrace spontaneity, that’s not me.

If left to my own devices, my daughter and I would probably spend the entire day at home because my spirit animal is a hermit crab reading a good book.

Instead, I make a plan.

This week, I pulled out my calendar and started time-boxing our days, just like I do for work: farm day, children’s museum day, playdates.

The details aren’t important. The point is that I know we’ll have more fun if I intentionally create opportunities for it.

The activities filling my calendar may change, but the process doesn’t.

Summer-Cat still likes plans.

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Back in January, I wrote about creating a time budget. It’s a super useful tool for allocating our time among work, family, health, and personal goals, but it works for seasons, too.

When life gets busy, whether because of summer break, a major project at work, a new baby, a move, or something else entirely, the first step isn’t trying to do everything.

It’s identifying what absolutely needs to happen.

Schedule those first, then build everything else around them.

For me, that means balancing work commitments, writing, speaking engagements, family time, exercise, and making sure two energetic children don’t spend too much time indoors in front of screens.

I do have a constraint, though: My son will still be in school and has requested that my daughter and I have fun, but not too much fun. Luckily, she enjoys trips to Costco and Target.

Sometimes these slower weeks make me feel surprisingly anxious.

I like momentum and making progress, and when my schedule changes, part of me worries I’m falling behind and not doing enough.

But seasons aren’t interruptions. They’re part of the plan, if you allow them to be.

Summer-Cat isn’t competing with Work-Cat.

She’s solving a different set of problems. Work-Cat will be back, more restored, because sometimes the best way to refuel your creativity and motivation is to switch it up.

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Office Hours Update

Speaking of adjusting to seasons, I’m making a change to office hours.

I’ve always held office hours as an open group session, but I want to experiment with a format that offers a little more flexibility for everyone.

Going forward, office hours for paid subscribers will primarily be one-on-one sessions.

Subscribers will be able to book a short conversation directly through a scheduling link. Whether you want to talk about entrepreneurship, marketing, career growth, public speaking, or how to keep a three-year-old and six-year-old entertained during summer break, I’m happy to chat.

I know some of you enjoy the group format as well, and I’m not abandoning that completely.

From time to time, I’ll continue hosting group sessions focused on specific topics. Think of them more like mini workshops or behind-the-scenes deep dives, like my “How I Actually Use AI” session, and I’ll open those up to all subscribers.

If you’re a paid subscriber, look out for the link later this week.

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First, I was extremely young when we started myYearbook. I did not feel young at 15, but as an adult, I realize fifteen is incredibly young.

With that said, fifteen-year-olds are also incredibly capable.

Of the roughly 100 students I met over the two days, several already had businesses. They had apps for connecting people in need with food pantries, helping friends track fitness goals together, encouraging people to drink more water, and more. It wasn’t all tech, either. One of my favorite ideas was a mobile oil change business.

When you talk to these students about what they’re building, you mostly forget how young they are. That’s the thing about building something. You become an expert in it. These students know their products best. They are already advocating for themselves, navigating problems, and learning how to communicate ideas clearly.

I was also reminded how much pressure they are under.

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College admissions have only gotten more competitive since I was in high school. During one session, I casually mentioned that my guidance counselor advised me not to apply to Georgetown because I would “never get in,” and I immediately saw panic in some students’ eyes.

So I quickly clarified two things:

1. My guidance counselor had no idea what she was talking about. I applied anyway and got in.

2. She was probably trying to protect me and manage expectations because our school rarely sent students there.

I also tried to explain something that is hard to believe when you are seventeen: decisions that feel life-defining in the moment often matter much less than you think they will.

I would have been happy at other schools. And if I wasn’t, I could have transferred. Several other panelists shared similarly nonlinear educational and career journeys.

At fifteen, I certainly did not have everything figured out. Honestly, I still don’t. But I remember the pressure to act like I did.

I hope these students can collectively exhale a little. Or maybe that only comes naturally later, once you find your people and realize there are many different paths to a meaningful life and career.

One thing that struck me, though, was that the questions themselves haven’t changed much. The biggest questions from teen founders are almost identical to the ones adult founders ask.

How do you get users?
And how do you manage your time?

Some problems never really go away.

I’ve written a lot recently about how I think about time management, including quitting, time budgeting, microsessions and batching, and protecting your focus. I also recently shared how I think about planning a launch.

I hope those resources help founders, students, and anyone else trying to build something meaningful while balancing the rest of life, too.

I’m looking forward to speaking to more student groups soon.

About Catherine Connelly:

Catherine Connelly is an entrepreneur, keynote speaker, and author of Designing Success: Lessons from 20 Years as a Female Tech Entrepreneur. She co-founded myYearbook as a teenager and helped grow it into The Meet Group, a NASDAQ-listed social discovery and livestreaming company acquired for $500 million. Today, she writes the weekly newsletter Growing Up Startup and speaks about innovation, decision-making, and unconventional career paths.

Of course, the important part was never really the number. It’s that the hours need to be deliberate.

You don’t improve simply because you spend time doing something. You improve by identifying the specific parts that need work and practicing them intentionally. That distinction has changed how I think about almost every skill I’ve tried to develop, and in today’s post, I’ll break down how I think about it.

One of my goals this year is to beat 23-year-old Cat’s 5K time and set a new PR.

At 23, I was running around 1,000 miles per year. But 36-year-old Cat cannot train the same way. I don’t have the same schedule, recovery capacity, or desire to spend endless hours running as I once did. What I do have now, though, is a much better understanding of how to train intentionally.

Back then, I basically ran every run at the same pace. I had one speed, and I held it. Now my training looks very different. I’m doing interval workouts, tempo runs, recovery runs, and long runs.

Before starting this new training plan, I did a 5K time trial and completely hit the wall during the third mile. I couldn’t hold my pace once I got tired. So instead of vaguely deciding I needed to “run more” or “run faster,” I started focusing on the exact weakness that was causing the problem.

Since tired legs are a problem, I am adding long runs so I can have some race-pace miles to practice on when my legs are already fatigued. I’m practicing the thing I know I am struggling with most.

The same thing is true with public speaking.

Years ago, a colleague told me he wished he could present like Gary Vaynerchuk and just completely wing it.

One year, I heard Gary V speak at two different events. He was phenomenal both times. Engaging, funny, commanding on stage, incredibly generous with his advice. He looked completely natural.

But he wasn’t winging it.

The second talk was nearly identical to the first. The same stories, the same pauses, the same jokes, even the expletives landed in the same places. What looked effortless was actually a presentation that Gary V refined over many, many repetitions.

That experience completely changed how I thought about speaking.

People love to describe others as “naturals” because it makes excellence seem innate. Either you have it, or you don’t. This belief gives us a great excuse.

“I can’t be a great speaker, I’m just not a natural.” Or, “I can’t learn to play an instrument, I just don’t have that talent.”

But most skills don’t come down to natural talent; they come down to deliberate practice.

Most great speakers aren’t naturals. They would never wing it.

In 10th-grade Spanish, we had to give short presentations in front of the class every week. I hated it. I would stumble through my three sentences, feeling completely terrified. Public speaking did not come naturally to me.

Now, after years of speaking at conferences, pitching investors, guest lecturing, and giving keynotes, I love it. I still get nervous, but now the feeling is exhilarating instead of dreadful.

That transformation didn’t happen because I suddenly became charismatic. It happened because I practiced deliberately.

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When I prepare for a talk, I usually start by doing a dry run to see what parts don’t feel right and mark them as I go. I record my talks so I can then also watch the exact spots and strategize how to improve them. Next, I break those areas up into chunks and perform them until they hit the way I want.

I practice standing up because muscle memory matters for blocking and staging. I listen to recordings of the talk while driving and running, and I rehearse in front of other people for feedback.

In the early days of the startup, my brother Geoff used to throw things at me while I practiced presentations. Ridiculous? Absolutely. But it did teach me that if you can stay composed while dodging objects, you probably know the material pretty well.

Before my TEDxBayArea talk, I recorded the entire presentation in Voice Memos and listened to it constantly: while driving, eating, running, etc. The event itself is kind of a blur, but I remember spending all night at the Ramada practicing and listening to the talk over scrambled eggs before heading over.

I still do this today. I listen to the talk, practice and iterate on it, and perform it many times.

None of this feels particularly glamorous. Deliberate practice isn’t glamorous. It can be tedious work.

It’s repetitive and targeted. It forces you to spend time on the exact parts you’re weakest at instead of the parts you already enjoy doing. That’s uncomfortable.

But that’s also how people become “naturals.”

Not through talent alone, but through repetition with intention.

What can you become more deliberate with?

Because it’s not really about doing more reps, it’s about doing the right ones.

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About Catherine Connelly:

Catherine Connelly is an entrepreneur, keynote speaker, and author of Designing Success: Lessons from 20 Years as a Female Tech Entrepreneur. She co-founded myYearbook as a teenager and helped grow it into The Meet Group, a NASDAQ-listed social discovery and livestreaming company acquired for $500 million. Today, she writes the weekly newsletter Growing Up Startup and speaks about innovation, decision-making, and unconventional career paths.

Des won the 2018 Boston Marathon in absolutely miserable conditions, becoming the first American woman to win the race in decades. Recently, I was listening to her podcast, Nobody Asked Us, and she shared a comment from this year’s race, her first one since retiring from elite marathon racing.1

In the recap, she shared that someone asked if she took the school buses to the start line like the other racers. Her response?

“I may not be elite anymore, but I’m still a VIP.”

Hell yeah.

I loved that line because so many people forget this during a transition. They think changing roles or industries means starting over.

It doesn’t.

You do not go back to zero. You keep the experience you have.

I see this especially with people moving into fractional work for the first time. Someone who spent decades leading marketing teams suddenly says, “Well, I’ve only done a few fractional gigs…”

Okay. But you still have decades of experience.

You still know how companies operate. You still know how to make decisions. You still know how to lead people, prioritize work, communicate under pressure, and figure things out when the plan breaks.

The format of the work changed. Your value did not disappear.

I think part of the reason imposter syndrome becomes so intense during transitions is that we over-concentrate on what is new and underrate everything we already know.

Learning by doing does not mean learning from scratch.

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You never learn something new in a vacuum. You learn through the lens of everything you already know.

A first-time founder who has managed teams for ten years is not the same as an eighteen-year-old founder doing it for the first time.

A new manager who has spent years navigating difficult clients already has the emotional intelligence and communication skills to bring to leadership.

Even simply being a human who has navigated “adulting” with life, relationships, responsibilities, and setbacks matters. Experience builds across contexts.

People tend to underrate transferable expertise. Competence isn’t tied to a specific title, industry, or credential. Many of the most valuable skills carry across environments.

The tools change. The fundamentals usually don’t.

When we were growing myYearbook, we focused heavily on channels like MySpace profiles and AOL Instant Messenger away messages because that was where people were spending their time. Obviously, nobody is optimizing for AIM profiles today, but the underlying principle remains the same.

If you’re marketing a product, you need to find where people already are, understand their behavior, and include your product in the conversation.

The channels and algorithms will change continuously, but the strategic fundamentals don’t.

That’s why experienced people often undervalue themselves when entering new spaces. They focus too much on the unfamiliar wrapper and not enough on the durable skills underneath.

One of the strangest examples of this mindset showed up in And Just Like That, the Sex and the City reboot. Miranda Hobbes, a highly accomplished attorney and former law firm partner, returns to school and suddenly acts as if she has no experience because she’s entering a new area of law.

But that’s absurd.

A woman who spent decades succeeding in high-pressure rooms does not suddenly become inexperienced because she changed specialties.

And yet people do this to themselves constantly.

“I haven’t done this exact thing before.”

“I’m new to this industry.”

“I don’t know this platform.”

Sure. But you are bringing every previous experience with you.

You don’t lose your judgment, instincts, pattern recognition, and resilience.

You are not starting from scratch.

You do not go back to zero.

You’re still a VIP.

About Catherine Connelly:

Catherine Connelly is an entrepreneur, keynote speaker, and author of Designing Success: Lessons from 20 Years as a Female Tech Entrepreneur. She co-founded myYearbook as a teenager and helped grow it into The Meet Group, a NASDAQ-listed social discovery and livestreaming company acquired for $500 million. Today, she writes the weekly newsletter Growing Up Startup and speaks about innovation, decision-making, and unconventional career paths.

It never worked for me.

Every single time, I got an error message saying the scan failed to process. I tried different lighting, different outfits, different rooms. I deleted and reinstalled the app. Tried on only wifi, tried on only LTE. Nothing worked.

Eventually, I mentioned it to my husband while attempting yet another failed scan. He watched me for a few seconds and then said:

“You’re doing it wrong.”

Which was annoying because obviously I was not doing it wrong. I was listening to the very clear instructions!

Except I was wrong.

The app tells you to “turn around” during the scan. There’s a countdown timer while you do it. In my head, I interpreted that as: turn around once so you’re facing the opposite direction.

Apparently, it meant to do a full 360-degree spin.

For months, I had been turning only 180 degrees and wondering why the feature didn’t work for me.

The embarrassing part is that once he pointed it out, the instructions suddenly seemed obvious.

Of course, that’s what they meant. Now, looking more closely, I even notice an arrow indicating a full revolution.

I share this embarrassing story because it’s a good example of the curse of expertise.

When you already know something, it becomes incredibly difficult to imagine what it feels like not to know it.

The people who built that app probably thought the instructions were clear. And, now that I understand them, they are. But they were designing from the perspective of someone who already knew how the scan worked (and probably 95% of their other customers understood it).

That happens constantly in products, leadership, and communication.

You explain something in what feels like a straightforward way, and the other person interprets it completely differently because they’re bringing a different set of assumptions into the conversation.

Even “turn around” can mean two different things depending on how your brain processes it.

This disconnect came up repeatedly when we launched new features at MeetMe. Internally, we would spend months talking about a product. We knew every detail. The language became second nature to us.

Then we’d launch it and run surveys asking users whether they had heard of the feature.

A shocking number had no idea it existed.

Not because they were unintelligent. Not because the messaging never appeared. But because we were communicating from within our own understanding rather than theirs.

The deeper your expertise, the easier it is to forget what it’s like to be new.

This concept applies far beyond product design.

I think about this a lot with keynote speaking. One of the things I care about most when telling stories from my startup journey is making sure they work even for people with no tech background.

I never want someone listening to feel like they need to understand mobile apps, venture capital, or social networking metrics to connect emotionally with the story.

The feelings matter more than the industry.

Most people will never build a social app. Just like most people will never become professional athletes or jump out of an airplane, they still understand pressure, uncertainty, ambition, fear, rejection, and resilience, and their stories still resonate.

That’s the part people connect to.

The challenge with communication is that we often focus on what we’re trying to say rather than how others will hear it.

So how do you overcome the curse of expertise?

You involve other people earlier.

You ask questions.

You stop assuming silence means clarity.

One of the most valuable things you can do in a meeting is ask the question you think you “should” already know the answer to. Chances are, you’re not the only person confused.

I recently saw a note from Katie Barnes sharing that 40% of startup problems would disappear if someone simply asked, “What are we actually doing?”

“What” and “why” questions matter because people often move forward based on assumptions no one ever verbalized.

The only way to discover communication gaps is to interact with real people.

You have to watch how they use the product.

Hear how they interpret the presentation.

See where they get confused.

Listen to the questions they ask.

That’s how you find the disconnect between what you meant and what others actually understood.

Clarity is not proven by how clear something feels to you. It’s proven by whether other people understand it the way you intended.

And apparently, sometimes that means realizing you were supposed to spin all the way around.

1. The biggest surprise was that recording the audiobook was harder than writing the book.

Going into recording the audiobook, I thought, “Hey! The hard part is done. I have the content. I just have to read it out loud.”

No, no, no, no, no.

I needed to perform it.

Writing is quiet and internal. You can stop, edit, rethink a sentence, walk away, and come back. Recording is none of that. You’re “on” the entire time. You’re managing your voice, your energy, your pacing, and your environment all at once.

I also needed to listen to my recordings a lot. Do you know anyone who likes hearing their own voice?

Every time I started a chapter, I knew I would dislike the first few minutes. There’s something about hearing your own voice that takes a second to get used to. I had to acclimate every single time before I could even focus on what I was saying.

It reminded me a lot of public speaking. I record my talks so I can watch them later and improve, but watching is always awkward, so before I can find value in the review, I need to get used to seeing myself and only criticizing myself constructively.

Then there was the environment. Writing doesn’t care if there’s background noise – I wrote my book primarily with Alan Gogol instrumental music in the background. Recording needs silence.

Suddenly, every sound matters. I moved my wind chimes to the garage to avoid ruining the takes, and I became ultra-aware of airplanes overhead. Since when are there so many planes?

There’s also a low-level panic running in the background the whole time. Did I hit record? Am I sitting in the same spot so the audio matches? Did I plug in the microphone? Did something just mess up that take?

It’s a very different kind of effort than writing, even though it’s the same content. Yes, the book took longer to write than to record, but the work of writing was stress-reducing. Recording an audiobook is just stacking stress on stress.

Another thing that really stood out was how not solo the process was, even though it feels like it should be.

2. Recording an audiobook isn’t solo.

An audiobook sounds like the most individual version of a project. It’s your voice, your words, your story. But there were so many people involved in making it what it is.

First, I did a course through my publisher on the whole process. My fellow author friends and I plotted how to mark up our manuscripts with narration notes, best – learning to highlight where breaths would go and sharing how we were tackling the process.

Next was voice coaching. The voice coaching didn’t just help with the audiobook narration but also with my speaking in general. I learned the important step of warming up your voice. Then, the recording began.

My producer listened to every chapter and flagged issues. A sound engineer edited everything and worked from a markedup copy of my manuscript where I highlighted re-takes for extra attention. Beta listeners helped me figure out what actually needed fixing versus what was just me being overly critical. For instance, I learned that I’ve been pronouncing “inundate” incorrectly for years. I was emphasizing the wrong syllable.

The whole process was another reminder of something I’ve seen over and over again: even when something looks like a solo effort, it rarely is.

The process was also especially mentally taxing because, unlike most things, there isn’t room for iteration.

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3. An audiobook is final.

Most of my career has been built on the idea that nothing is ever really final. At myYearbook, MeetMe, and The Meet Group, we were always testing, tweaking, rolling things out slowly, or rolling them back. Even the biggest decisions had some flexibility built in. You could adjust after the fact.

The audiobook didn’t work like that.

There was a deadline for re-records, and a practical limit on how many you should do. You don’t want your audiobook to sound like a Frankenstein monster of clipped together sentences. My producer limited me to ten.

Even after multiple rounds of editing, proofreading, and reading the entire book out loud eight times, and listening to the raw recordings three times, you can always find something to change.

A year later, that’s probably the biggest lesson that stuck with me. Not every change is an improvement. Sometimes it’s just you continuing to tinker because you can.

Having a cap on re-records forced me to be more thoughtful about what actually mattered. I relied a lot on beta-listener feedback to guide that. What would a listener notice? What would actually make a difference vs. what just felt imperfect to me?

That constraint was uncomfortable at the time, but it was also useful. Without it, I could have kept going.

It also made me realize how rare true finality is in most work. We tend to treat decisions as if they’re permanent, as if getting them wrong is a big deal. But most of the time, they’re not. You can adjust most projects and revisit decisions. We just don’t typically recognize the flexibility in the moment.

The audiobook was one of the few things I’ve worked on where that wasn’t true.

You record it, you submit it, and that’s it.

No edits. No updates. No second version.

It’s just done. Final.

At the time, that felt pretty terrifying. Now, a year later, I appreciate it more. It forced me to finish something without over-optimizing it. To let it stand as it was. And to move on to the next thing.

Which, in the end, is the whole point.

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Thanks for reading! If you haven’t yet, you can check out the audiobook for Designing Success: Lessons from 20 Years as a Female Tech Entrepreneur here.

My mean ex-dentist even acknowledged that despite my thin hair at 17, I have nice skin.

Because I’ve never had issues with my skin, I never prioritized washing my face. Despite that, I knew it was something I should do.

But after seeing about 10,000 anti-aging ads, I asked ChatGPT to make me a simple skin care routine and recommend products: cleanser, moisturizer, sunscreen, and retinol cream - all stuff from Target.

Two weeks after I started my regimen, something weird happened.

I started feeling proud of myself.

My skin hadn’t really changed, but I felt different. After all, we all know face-washers have their lives together.

The super-simple habit of washing my face started to impact other areas of my life.

There’s a lot written about how small habits can create outsized change. I just didn’t expect it to feel this immediate.

I found that washing my face (and the associated pride) created an identity shift that made me more likely to make other better choices throughout the day.

I was a face-washer. My identity had subtly shifted, creating a spillover effect that extended far beyond my face.

I noticed it while snacking on sugar snap peas and drinking lemon water. All of a sudden, I became more alert at the start of my morning and got better about not using my phone in bed at night.

Face-washers get stuff done. At least, that’s what I started to believe.

We tend to think the habit we want to build has to be directly related to the outcome we care about. If you want to get in shape, work out more. If you want to be more productive, start with a power hour routine.

Sometimes the habit you want to form, though, is too much of a leap, but magic can happen in the small, unrelated wins. These wins can help us shape our identities.

So if you’re looking for a Q2 reset, pick a habit that’s easy to win and let it ripple.

Turns out it was never about my skin.

Her AI-first company is killing it – shipping fast and by all measures doing exceedingly well. It’s the definition of productivity and efficiency. She shared that she’s done more in the last 8 weeks with a team of about 10 than she had done at her previous company in 6 months with a team 5x the size.

Though efficiency is something to celebrate, it makes her pause: “Should we be building this fast?”

That question gets at something deeper than just AI.

It gets at how we work.

Two things are happening at once.

AI is dramatically increasing our ability to execute. Things that used to take weeks now take hours. Things that used to require teams now require one person with the right tools.

Though the pace of work is changing, the expectations are increasing as well. We’re expected to do much more in the same amount of time.

As Yuval Noah Harari notes in Sapiens, we’ve been falling for “luxury traps” since the agricultural revolution, when our ancestors committed themselves to being confined to their lands, embarking on a more grueling lifestyle than that of the hunter-gatherers before them.

Obligation increased with output.

We create tools to make life easier, but then we use them to do more. Email has made work more efficient and communication faster, but now people expect an instant response. Smartphones made work portable, so now, work is everywhere.

AI is following the same path. It increases the pace of work, but not how we choose to spend our time. The default is to do more, increasing the speed on life’s treadmill.

Still, there isn’t an option to opt out of AI. If you aren’t on the train, you will be left behind. So the question isn’t whether to use it, but instead: how?

Where AI is incredibly powerful is in execution. AI allows us to move, polish, and test faster, but it doesn’t replace thinking.

And that’s where the lines start to blur.

There is a temptation to turn to AI for everything – it is fast! It comes up with okay-sounding ideas in seconds! But those ideas are just surface-level. Now more than ever, it’s important to do the harder work of developing the idea.

I used to say, “ideas are a dime a dozen, it’s execution that matters,” but that’s incomplete now.

Though execution still matters and you still need to ship, iterate, and follow through, as execution gets easier, it becomes less of a differentiator.

With execution increasingly accessible, the nuance and specificity of ideas matter more. Not just having an idea, but understanding it deeply enough to shape it into something meaningful – deciding what to build, why it matters, and what makes it different.

Yes, multiple smart people will work on similar things – multiple discovery has always been a thing. But the edge is no longer just about who executes; it’s about who sees more clearly.

But clarity doesn’t happen at the speed of AI. It requires space.

When I wrote my book, part of the publishing timeline included a full month of “drawer time” between finishing the first draft and starting revisions. The goal was simple: step away long enough to see the work clearly. That allowed me to “kill my darlings” and understand the work better.

That space is part of the process.

As founders and leaders, it’s easy to confound the two. We can move faster than ever, and in many cases, we should.

But not everything should move at breakneck speed.

We shouldn’t be making decisions at the speed of AI.

We should be making them at the speed required to direct the product, the company, and our lives in a way that actually makes sense.

So, should we be building that fast?

Yes.

Execute fast, but think slow.

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