Nope.

You can never do enough or get enough to overcome the feeling of not being enough.

I tried to do this for years. Decades even. High School Valedictorian? Check. College Degree with Highest Honors? Check. Top Law School? Check. Law Firm Partner Track? Consulting Firm Partner? Participating in an IPO? Check, check, check.

At every stage I thought “Because I have this (or have done this), I will now be happy.”

And what I got was money and titles, yes, but also panic attacks and confirmation that I still wasn’t “there” yet, that I wasn’t good enough, and that I had no idea how to become good enough other than to keep doing more of the things that I knew weren’t working.

Sound familiar?

Why Do You Think You’re Not Enough?

I see two reasons that even leaders like you don’t think you’re enough.

First, you don’t see that you are always living in a one hundred percent thought-generated world. And that those “I’m not enough” thoughts, along with all your other thoughts, constantly come and go.

Second, you believe in your default identity, the stories that you have believed about yourself and the world for as long as you can remember. Those stories constantly reinforce your sense of “not-enoughness,” however that happens to show up for you. You hope that by changing your outer circumstances, the not enough stories will change, too.

It doesn’t work that way. But by looking closely at your inner world, there are ways to dissolve that sense whether your outer circumstances change or not.

In fact, for most people, changing your inner world makes changing the outer world much easier.

How do you do that? You can confront the truth head on, or you can sneak up on it a little at a time.

How To See The Real Truth

If you are truly willing to look, it is easy to see that you have no solid identity. Identity, like the rest of your world, is made of thoughts. And thoughts, which may or may not even be “your” thoughts, come and go all the time. When you let go of them, of needing them, you can merely witness them without attachment.

This can happen through years or even decades of spiritual practice, or through a sudden and sometimes very disconcerting awakening experience. While this is the path to true freedom, it can wreak havoc on lives if it comes too fast.

Thankfully, most people don’t get this kind of dramatic shift. Instead, they move through somewhat predictable stages. I’m going to write about some possibilities here, but there are many other models and many other descriptions of this. Don’t confuse the map for the experience of navigating through the territory. (Your mileage may vary.)

What’s Your Default Identity?

Take out a piece of paper and write the words “I am _____.” Then fill in as many words as possible. Some of them might be positive, some might be negative. “I am hardworking. I am lazy. I am smart. I am unorganized.”

You get the idea.

Take a look at those words—they are a window into your default identity. This is the identity that you have taken on without your consent. The things your parents told you, your teachers, your bosses, your culture, your social media feed. The insistent messages that you believed simply because you didn’t see you had a choice.

Is it any wonder you feel bad about yourself from time to time?

You also have created a default world. A default view of every other person in your life. A default view of money, of relationships, of political parties, of running a business.

And all of that is running your life right now.

Living into Your Default Future

This is the future that you will create if you don’t question, challenge, or change your default identity.

All those limits you place on yourself and the world will keep you either thinking small, failing repeated through misguided hubris, or some combination.

Take a look at the assumptions you have made about your future. How does it look?

What Do You Want to Create Instead?

What if, instead, you started with the future you actually want?

This is where people can get tripped up a bit. Because it can be hard to create a future just because you want it, rather than because wanting the things you think will fix your default identity.

It can be helpful to say, “What do I want to create just because I want to create it?” Or “What wants to be created through me?”

Not because any of it will fix you, or help you prove yourself. Not because it will make you enough. But because it will come from some deeper part of you that already knows you are perfectly fine the way you are. And that wants the journey of knowing you can be more, without actually needing to be more.

Take some time and write some of those things out. Journal. Let yourself think big. It might feel both exciting and a little scary. You might think “could I really create that?” Ignore the “practical” thoughts showing up as fear to protect you. Think as big and as clearly as you can. Even if it is only the next step or two, visualize it and feel yourself having accomplished it. That future exists in the quantum soup of potentiality. It is there for the making. In a very real sense, some version of you has already created it. The only question is whether it is this version of you.

Imagine yourself in conversation with that future you.

The Reality of Created Identity

Who do you need to be today to create that future?

What characteristics do you have? Determination? Discipline? Fearlessness?

What habits do you have? The person who created that thing ten years from now, what are they doing today? How are they spending their time today? What habits do they have, what relationships do they have, what skills do they have?

What commitments have they made?

What small step are they taking, are you taking, today, toward that future?

Be that person. Take that step.

Remember all those thoughts that made up your default identity? You are replacing them with new thoughts. New words. And new actions.

You believed before that you were describing yourself and the world. But you were actually creating yourself and the world. And you do this no matter what. The only question is whether you do it consciously.

“Be impeccable with your word,” is the first of Don Miguel Ruiz’s The Four Agreements. When you see the creative power of your word, you will get this at a deeper and deeper level. And more and more you will become conscious of what you are creating in each and every moment.

Creator, Not Created

You can create any number of identities and futures. But the most important thing is to recognize that you can. You are always creating.

You create everything in your experience and the journey is to become more and more conscious of how and what you are creating.

As you see this, you will truly know you are not only enough, you are actually infinite. Because you have the infinite capacity to create. A capacity which, to this point, you may have barely been aware of.

True, you will never create it all, at least not in this lifetime. But if you have a choice in what you are creating, why would you ever create the idea that you are not enough?

Want to Take the First Step?

This can be heady stuff, but the first step is actually very simple. I’ll be releasing a powerful tool to help you take control of your current world so that you can free up the space to create the next one.

Comment “Pick Now” if you’d like a copy when it’s released.

“If I slow down, I’ll lose my edge.” — Every Founder I Talk To

The Fear of Slowing Down

I have a lot of conversations with founders who are proud of their capacity to work hard, to grind, to do as many things in a day as possible, to be a hero.

When I point out that their pace is unsustainable, they agree. But they confess they have no idea how to slow down, and frankly, they aren’t sure they want to.

To them, the grind isn’t a cost, it’s a benefit.

You tell yourself the long hours, the intensity, the constant motion are what got you here. You push through the health scares, the strain at home, the gnawing sense that life’s passing by, that you’ll miss your children growing up. You convince yourself it’s necessary, that you’re doing it “for them.” Because the work feels important and urgent and you’re terrified you’ll miss your moment.

You hope all that grind will be worth it, and that you can fix everything you break once you hit your goal. Even if that’s after a decade or two.

But what if the very thing you’re afraid of losing is the thing that’s waiting to emerge?

What Your Edge Really Is

Most high performers mistake their edge for their speed.

They think:

• My ability to grind makes me different.
• My stamina is what keeps me ahead.
• I have to capitalize on this moment or I will lose it forever.

If your idea requires you to be first, it’s not a very sustainable idea.

If your edge relies on going faster than everyone else, it’s not an edge—it’s a coping mechanism.

Your real edge is your perspective.

It’s the unique mix of experience, insight, and values that no one else has. Your edge doesn’t come from pushing harder; it comes from getting still enough to hear your own voice.

The Secret No One Tells You

Slowing down doesn’t dull your ambition—it sharpens your aim.

When you stop running on adrenaline, the noise in your system fades. You start hearing a quieter signal: guidance, intuition, insight. The work that comes from that place isn’t just more sustainable—it’s unmistakably yours.

You become what I call an N of one—impossible to replicate, incomparable in the market. Building unique, sustainable things that no one can compete with. I’ve seen this in personalized industries like private air travel and health care, but I’ve also seen it in roofing, in construction, and even employee benefits administration.

How to Claim Your True Edge

You don’t need to meditate for an hour a day or escape to a retreat. Start with one minute of quiet—

• Use a binaural beats app or playlist to drop into stillness faster. (Training wheels for the meditative state!)
• Go for a run or even a walk in the park.
• See what’s humming beneath the noise—a feeling, an image, a knowing.
• Act on one small piece of that guidance each day.

Embrace what you find, even if, especially if, it makes no logical sense. This isn’t about huge leaps. It’s about slowly building trust in yourself, and those around you, for the sake of a bigger vision.

A vision that will be more and more deeply your own.

What You’ll Discover

When you slow down, you’ll see how much of your old drive was about proving something—to your parents, your past, or the mirror.

You’ll see your need to be enough in full force. And you’ll see it’s been running the show.

That insight is the beginning of freedom.

Freedom from the stories you keep telling yourself. The disastrous futures you make up at 4 in the morning.

You’ll start creating not from fear, but from freedom. Not only freedom from that stress, but freedom TO finally speak and be your truth. To step into your unique vision and create something from the sense of purpose that emerges.

When you can create anything, not just the thing you think will make others happy.

When you that, you customers find you. Your employees find you.

Because had the courage to show them the real you.

Want to Take This Deeper?

I’m creating a tool to help founders get unstuck from the daily grind. To start to get back to themselves while making decisions faster then ever.

Want a copy? Comment “Pick Now” and I will send you a copy when it’s ready.

I just saw a post that echoes what my coach told me about confidence a few years ago.

“Confidence is not a requirement. It’s a result.”

The idea is that the only way you get confidence is by doing something over and over.

It is certainly true as someone gets better at something their confidence increases. But what about when you really need to do something that you aren’t good at? Or that you are doing for the first time?

Founders are constantly doing this. Creating strategies that they have never executed on. Making decisions with about 10 percent of the information they need.

Most of the time they have no idea if what they are trying will work.

If You Don’t Have Confidence, Then What?

This week I was on Ryan Munsey’s  Move The Chains podcast talking about confidence, and clarity, and all kinds of other things that leaders need to move the chains (it’s an American football reference—the consistent forward motion that you need to win the game).

You don’t need confidence to do the thing. If you’re afraid, you can still do it. Make the phone call, have the conversation.

But where are you coming from in having that conversation?

Two Levels Beyond Confidence

What no one tells you is what’s just on the other side of confidence.

Boredom.

I want an accountant who has filed a thousand tax returns. I want a surgeon who has done the procedure 10,000 times.

But as an entrepreneur, I don’t want to ever do something 10,000 times. Nor do my clients.

So if none of us is ever going to get to that level of task confidence, how do we lead?

How do we feel the fear and do it anyway?

1. Commitment. If I’m not confident, I may choose not to do something. To reconsider. To analyze the data one more time. But if I am committed, I must do it. Even if I am only committed to a process. I might not be confident in my ability yet, but I can be confident that if I commit to a process I will get better and better. That the only way to get better, in fact, is to commit to a period of doing it badly. To commit to a process of improvement.
2. Certainty. At an even deeper level, you can operate from a place of certainty. That you have the innate ability to figure it out. That, in the words of an entrepreneur friend of mine (and upcoming podcast guest), “I didn’t come this far to have the universe drop me on my ass.”

You’re At the Door of the Plane

You’ve checked your chute (and your backup).

Do you jump, or not?

Of course you’re afraid. The fear is the sign you’re ready.

If you’re committed, if you’re certain, you jump. Despite the fear.

No, actually because of those things.

You can be committed and certain even if you don’t know exactly how things are going to work out.

The same holds true for your team.

They want you to lead them. Your commitment and certainty are a perfect filter. If they are inspired, they are your people. If not, kindly say goodbye and find someone who is.

What Are You Committed To?

What’s the thing you are willing to work at until it works out? What’s the thing you know, deep in your soul, is going to work out, even if you don’t know how?

Share in the comments.

Pick Now Podcast, Coming Soon!

I can’t wait to share some of the stories that I am hearing from founders who have made hard decisions, over and over. Subscribe to my emails to make sure you get the latest news.

If you’ve ever hiked in the mountains, you’ve probably hit a false summit. From below, you’re sure you’ve spotted the top. You push hard, heart pounding, legs burning, only to arrive and realize—you’re not there yet. The peak is still further on, hidden until now.

In business and in life, the same thing happens.

At a recent weekend on a Colorado ranch, I spent time with a group of founders who had already reached what most people would call the summit. They had sold companies and along that had gotten validation, recognition, and in many cases, a lot of money. And almost to a person, they told me some version of this:

“I thought it would finally make me feel like I was enough. Instead, it was the opposite. After a few days, I fell into a valley of despair. Disillusionment. Who am I now? If this isn’t it, what is?”

That’s the sting of a false summit. You think the climb is over, only to find a whole new stretch of trail you hadn’t planned for. And it’s overwhelming.

The financial success is real, and it matters. It buys freedom from: freedom from financial worry, freedom from needing to work again, freedom from the stress of survival. All of that is worth celebrating.

But it’s only one layer.

The deeper, more enduring freedom is freedom to—

• Freedom to say what you truly feel.
• Freedom to do what you actually want to do, to create what is in your heart, instead of what others expect.
• Freedom to be more, or just to simply be.

At our core we are infinite creativity. Most of us use that creativity to prove ourselves, or to fight against something.

I know for many years I was so attuned to what others wanted, that I had a hard time accessing what I wanted.

After doing all the things I was told would make me happy and still feeling empty, I began to see that the freedom I wanted wasn’t outside me, but inside. That I could free myself of the prison of others’ expectations. The prison that I had actually built.

You have built some version of this prison, too, and you have always had the key.

When you see you have always been free, you don’t stop creating. But you do create from a different place—one that isn’t about proving, but about expressing.

Whatever you call that—freedom, or mission, or purpose—is the real summit you’ve been looking for all along.

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Do you recognize any “false summits” in your own journey? What looked like the finish line, only to reveal itself as just another ridge on the climb?