Hey friends!

A year ago, I started working one-on-one with people who felt ready for a new direction but stuck in their current lives.

And to be honest, coaching wasn’t something I ever considered doing.

But it has been one of my greatest teachers.

It showed me what it means to truly listen and be present, helped me understand what people are really struggling with, and—ironically—gave me greater insight into my own challenges.

After reviewing my notes from the past year, one of the biggest surprises was how often highly capable, successful people struggle to create something of their own—and sustain it.

Here are the 5 biggest things I learned from these sessions:

1. People are usually not bad at execution. They struggle to operate outside of familiar structures.

Give someone a deadline, expectations, and a defined next step, and most people will rise to the occasion. But after years, or even decades, executing inside someone else’s structure—like a company, organization, or institution—taking action outside of that can feel strangely difficult.

Because now you have to create the path for yourself.

There’s no prescribed sequence, no obvious next step, and no one telling you whether you’re doing it right. So someone who’s been highly capable for years can suddenly find themselves asking: What’s the first step? What’s the process? What do I need to learn?

2. “I never follow through” is rarely a discipline problem.

What we call a lack of discipline or follow-through is really self-protection from the uncertainty of not knowing what to do—or how we might look while figuring it out.

Because the moment you have to act on an idea you have, the stakes become real. You could choose wrong, waste time, lose money, or fail. And if you’ve been burned before, that uncertainty carries even more weight.

So what looks like procrastination or inconsistency is your system protecting you from another painful outcome — by delaying decisions, switching directions, or stopping before you’re fully exposed.

3. Your existing successful identity can become the thing keeping you from the life you actually want.

The more successful you become in one role, the harder it can be to admit that the role no longer fits. You have income, competence, status, and years of proof that you know how to succeed as this person.

Moving toward something more self-directed has none of those guarantees. It means becoming a beginner again, giving up certainty, and stepping into an identity you have no track record in yet.

That tension feels like confusion, or like there’s something wrong with you. But it’s really a conflict between the self that knows how to succeed and the self that wants a different life.

4. The same habits that made you successful in the past can work against you when you’re building something of your own.

When working harder, pushing through, and constantly “climbing the ladder” have been rewarded for years, they become your default response whenever you want to make something happen. So when you decide to create something of your own, you approach it the same way: add another goal, find another system, optimize more, do more.

But what helped you succeed inside an established career can create more pressure and exhaustion when you’re trying to create something self-directed.

You want more freedom, but end up turning the thing you’re building into another performance test.

5. The more capable you are at finding answers, the easier it is to avoid making the decision only you can make.

When research, learning, and problem-solving have helped you succeed for years, uncertainty quickly becomes something else to figure out. So when you’re trying to create a new life chapter, you take another course, compare more options, or keep searching for the right approach.

It’s that very act of “searching” that puts you back in the role you know best: the smart person who masters information.

But the move to make is simpler, and more exposing: choose one direction without certainty, then trust your judgment as you find your way. So the search for the “right answer” becomes the very thing that keeps you from making one.

✧ ✧ ✧

So what might this mean for you?

If you recognize yourself in any of those five, it’s a reminder that you don’t lack capability or skill.

I may not know you personally, but if you’re reading this, you likely have expertise, a wealth of experience, or a unique gift that can help someone else.

But the question becomes:

• How do you build something when you have to define, make the decisions, and create the structure yourself?
• How do you learn to trust yourself when there’s no institution, boss, credential, or established path telling you what the next step should be?
• How do you get started and stick with it—when there are no expectations or deadlines forcing it forward, no one waiting for it, and something in your current life always feels more urgent?

This is the gap between wanting to create something of your own and actually building it.

I know because I’ve lived a version of it.

But I’ve found that this isn’t only a “find your purpose” problem or a “start a business” problem.

It’s what happens between those two things.

At some point, you have to take all the expertise and experience you’ve gained and turn some part of it into something other people can actually benefit from by getting clear on:

• Who do you want to help?
• What do you want to help them with?
• What could you offer?

Then there’s the practical question of how to start building it while still keeping the career you already have—and without turning it into another demanding job that consumes your time.

That’s why I’m thinking about working privately with a small number of people who are in this position.

Maybe you want to teach what you know, coach or consult, or build a business around an idea you’ve been thinking about for a while.

Whatever it is, we’ll clarify the work you want to build, turn your experience and expertise into a clear paid offer, put a simple structure around it, and start getting it into the world alongside your current career.

If any of this sounds like you, hit reply and tell me:

With gratitude,

Anthony V. Lombardo

Essays on Substack
Subscribe On YouTube