I flew into Ft. Lauderdale last week to speak at an event where I knew exactly one person in the building. By dinner on the first night, that had changed, and not in the way you’d expect from a name badge and a handshake.

Somewhere between the appetizers and cruising the harbor, the table stopped trading the polished version of how business is going. Someone said the number they actually did last quarter vs what they wanted it to be. Someone else admitted the growth everyone had been congratulating them on came attached to a problem they hadn’t fully solved yet. It’s the difference between telling someone your car runs fine and popping the hood so they can see for themselves.

Here’s the part I keep thinking about. Most people don’t keep the hood closed because they’re hiding something. They keep it closed because they haven’t looked lately either.

The event was the Ecom Profit Group event, hosted by Charles Leikauf. Everyone in the room owned an accounting and/or bookkeeping practice. Some were in the mix or building from scratch, while others were years in and reworking what they’d already built. I spoke on what it actually takes to clean up a set of books that has gotten away from a business, the kind of situation where a company is doing serious revenue while nobody has reconciled anything in three years.

Here’s what I want you to sit with about that kind of client. They usually feel fine. Money is coming in, the business looks healthy from the outside, and there’s no alarm going off anywhere. The feeling and the facts had been running on completely separate tracks for years, and nobody noticed because nothing forced them to compare the two.

Show Me Your Friends

If there’s one thing I’ve become more convinced of over the years, it’s that you really are who you surround yourself with. I talk about this a lot, but for good reason. Everyone has heard the phrase “show me your friends and I’ll show you your future,” and I think it holds even more weight when you’re an entrepreneur. Success looks different for every founder, which is exactly why being around other entrepreneurs matters so much. You get exposed to versions of it you hadn’t considered, and the assumptions you’ve been operating under start to shake loose. It’s good for the soul, sure, but more importantly, it’s good for the way you think.

What Fifteen Minutes Buys You

One of the things that always surprises me about events like this is how much you can pick up in a short conversation with the right person. I’m talking fifteen minutes, sometimes less. Someone shares how they’re thinking about a hiring decision, or how they’re approaching a customer segment, or what a recent mistake taught them, and it lands in a way that a book (or a newsletter) on the same topic never would.

There is no better way to learn than face-to-face. Whether that’s the added context or the fact that the interaction is just more authentic, I honestly don’t know. What I do know is that the most consistent driver of success in my career has been my willingness to learn, and I think that’s true for most entrepreneurs. The people I’ve been in the room with who are the most successful are almost always the most open to learning, regardless of who they’re talking to. That’s a different kind of humility, and it’s a big part of what separates them. Don’t overlook the value of a fifteen-minute conversation.

Everybody Named the Same Thing

As good as the tactical conversations were, one topic came up far more often than I expected. Almost everyone at the table, in one form or another, said some version of, “I feel like I should be doing more.”

Everyone in that room was somewhere on the same road, just at different mile markers. Some had just hit a new stage of growth and were figuring out what the business needed to become to hold it. Others were in the middle of pivoting their practice entirely, betting on a version of the work that didn’t exist for them a year ago. Different industries, different problems, same underlying goal of keeping things growing.

What surprised me was how quickly the conversations turned honest. People started naming the exact places they had been stuck, and almost every one of them traced back to some type of fear. Charles shared an analogy about fear, one that traces back to Elizabeth Gilbert. Fear is allowed in the car, because it’s going to climb in whether you invite it or not. What it doesn’t get is the wheel. It doesn’t pick the route, it doesn’t choose the stops, and it doesn’t touch the radio. Nobody in that room would argue with that. Every one of them could still point to a decision where fear had been driving.

The Bar Moves Without Asking

The more we talked about it, the more I noticed a pattern that I think explains a lot of what these founders were feeling, and it’s something worth talking about because I don’t think we talk about it enough.

When high performing people hit a big goal, the accomplishment doesn’t stay a peak the way you’d expect. It becomes the floor. The revenue number that felt impossible eighteen months ago turns into the number you compare next Tuesday against. The team you dreamed of building turns into the team you now have to lead through the next hard thing. The milestone doesn’t stay a milestone. It quietly becomes a starting line.

That’s why competent people so often feel like they aren’t doing enough. It isn’t that they’ve stopped accomplishing things. It’s that whatever they just accomplished has already been absorbed into their definition of normal, and they’re now measuring themselves against a version of themselves that didn’t exist twelve months ago. You’re always chasing the person you just became, and that person keeps raising the bar without asking your permission.

Now here’s the part I believe more strongly than anything else in this letter, and it’s where I’ll probably lose a few of you. Most founders can’t tell the difference between the two, and it isn’t a mindset problem. It’s a data problem. When your numbers are clear, “should I be doing more” is a question with an answer. You look at the trend, you look at the margin, you look at what the last two hires actually produced, and the data either backs the worry or it doesn’t. When your numbers are murky, there’s nothing to check the feeling against, so the feeling wins by default. Guilt expands to fill whatever space the facts leave empty.

That’s why the founders at that table who felt worst were not the ones performing badly. They were the ones who couldn’t prove they were performing well.

The Wiring Cuts Both Ways

That same wiring, the thing that moves the baseline higher every time you hit a goal, is what makes high performers who they are in the first place. You wouldn’t want to fully shut it off, because it’s the same instinct that’s responsible for everything you’ve built so far.

The problem is that if you never turn it off, you run the entire race feeling behind. You never let yourself register a win, because by the time you feel it, you’ve already moved on to the next thing. Plenty of founders end up living there without ever noticing they moved in.

I don’t have a tidy fix for it, and I don’t think there is one. I do think naming it helps, because once you can see the pattern, you can catch yourself in it. The next time you feel like you’re not doing enough, it’s worth asking whether that’s a real signal about your effort, or whether it’s just your baseline moving on you again. That question matters more than it sounds like it does, because a founder who feels permanently behind is exactly the founder who hands fear the wheel.

Go Find the Room

The reason events like this matter isn’t the tactics that trade hands, as good as those were. It’s that a room full of honest people will tell you what normal actually looks like, and a room full of people one step ahead of you will tell you what’s actually possible. You cannot calibrate either one alone in your office, and you definitely cannot calibrate it from what people post.

So, if I leave you with one thing from last week, it’s to go find those rooms. Not the polished, panel and headshot version, but the real ones where people are willing to say the honest thing out loud. Don’t overlook a fifteen-minute conversation with the right person, and don’t underestimate what changes when you spend time around people who challenge how you think.

I’d add one more thing, and it’s the part that’s harder to hear. Everyone tells you that feeling behind is normal and you should give yourself grace. Sometimes that’s exactly right. Sometimes you actually are behind, and the grace just buys you another quarter of not knowing. The uncomfortable truth is that you can’t tell which one you’re in until you can see your numbers clearly enough to argue with them. One of those problems is a feeling you have to sit with. The other one you could fix this month.

So here’s my ask, and it’s the same one that table made of each other over dinner. Hit reply and tell me which one you’re in. Are you actually behind, or does it just feel that way? If you can’t tell, say that, because that’s the most honest answer of the three and it’s the one I hear most.