Dan was less than a year into his CEO role when the cracks started showing.

Expenses out of line. An acquisition quietly failing. A sales team running entirely in reactive mode. The previous CEO — one of Dan’s mentors — had left more undone than anyone realized.

Dan needed to grow.

But first he was going to have to cut. About ten percent of the workforce.

He froze.

In his mind, he was not restructuring a company. He was letting people down. Those families were counting on him.

I have watched a lot of leaders freeze in the exact same place. Because of the weight they believe they are carrying.

Employees. Families. Mortgages. Kids’ tuition. The whole web of human consequence, apparently riding on whatever the leader decides.

It can feel noble.

It can also become paralyzing.

And most of the time, it’s not nearly as true as it feels.

The Story That Looks Like Responsibility

Dan’s story sounded responsible.

“I can’t do this to them.”

Who wants to push back on a CEO trying to protect livelihoods?

But look closely.

Sometimes “I am responsible for my people” is not responsibility. It’s the most respectable reason you have found not to choose.

It lets you stay in place and feel virtuous about it.

In Dan’s case, waiting wasn’t protecting anyone. The expenses kept bleeding. The acquisition kept losing money. The sales team kept not selling.

Every week he delayed, he was choosing.

He wasn’t naming it as a choice. But the decision was already being made. Week by week by week.

Who Is Actually Counting on You?

There are two possibilities.

The first is that someone has genuinely handed you responsibility for their livelihood, their stability, or their future.

If that’s true, it says more about them than it does about you.

They have made you the central character in a life they are meant to be living themselves. You can care about them. You can support them. You can lead them well.

But you’re not responsible for them. They are.

The second possibility is harder.

You may have built — or, in Dan’s case, inherited — a company where too much really does depend on you.

Decisions stall in your inbox. People wait for your approval. Nobody wants to move without your blessing. The whole place has learned to orbit around one person.

If that is happening, it did not happen by accident.

Someone created the pattern.

Which also means you can change it.

What Kind of Company Do You Want?

Be honest.

Do you want people who treat you like the weather — something that happens to them, something they monitor, something they wait out?

Or do you want people who are aligned with what you are building and also clearly running their own lives?

People who know they have options.

People who could leave tomorrow and choose to stay.

People who can make decisions without you.

People who will sometimes do it differently than you would. Better than you would.

Most founders and CEOs say they want the second kind of company.

Many have built — or inherited — the first.

The cuts Dan was avoiding were not just about cost. They were about whether the company he was now responsible for could ever become the second kind.

If They Are All Counting on You, That Dependence Is the Signal

If the business falls apart without you, that’s not proof of your importance.

It means you built something that cannot stand without you.

The healthiest companies I have seen are not founderless. The leader matters. Their taste matters. Their judgment matters. Their standards matter.

But the company does not require their constant presence to function.

The place keeps moving.

People keep deciding.

The leader can leave for thirty days, or even a year, and come back to a business, not a pile of delayed decisions.

The leaders who feel most indispensable are often the most exhausted.

And the most stuck.

Decide From Freedom

When Dan stopped using “those families are counting on me” as the reason he couldn’t move, the decision became his again.

Not the board’s.

Not his investors

Not the imagined version of his employees’ families.

His.

He is making the cuts. Carefully and quickly. He can be honest with the people affected, and clear about why.

Now he can start building the company he actually wants to lead.

You can still care deeply about the people in your company. You probably should.

But caring about people is not the same as carrying them.

When you stop carrying them, two things often happen.

You make the decision you have been delaying.

And the people around you start showing up as adults, owners, and leaders.

Together, you can be stewards of the company, while building the people who can lead that company well beyond where you ever could.

When was the last time you sat with a cup of tea and simply looked at your life?

Tea in your hand. Light on the floor. Breath moving. Life, already here.

When I ask people some version of that question, the response is almost always the same: a short laugh, a pause, and then, “I honestly can’t remember.”

And for a moment, they see it. They see how long it has been since they let life touch them without immediately turning it into something to manage.

The Strange Poverty of a Full Life

I hear about overwhelm constantly. Leaders running from meeting to meeting, crisis to crisis, commitment to commitment. A business issue in the morning. A kid’s soccer game in the afternoon. A half-written email at night. A low hum of “I’m behind” running underneath everything.

Many of these people have built extraordinary lives. Homes. Families. Businesses. Choices. Opportunity. And yet they rarely feel free enough to enjoy any of it.

The life is right there. They are somewhere else.

Working “On” Your Life

In the founder world, we talk about the difference between working in the business and working on the business. If you never step back, you never really see the system. You just keep reacting from inside it.

The same thing is true of your life.

Most people are just responding, all day long, to the activity of their own mind. A worry appears, and they follow it. A rule appears, and they obey it. An urgency appears, and they call it reality.

Very rarely do they stop and ask: What is my mind actually producing right now? What am I believing? Whose rules am I still living by?

Because you are not living in “the world.” You are living inside your model of the world — built from memory, fear, desire, approval, disappointment, ambition, and whatever you decided long ago you needed to become in order to be okay.

Some of those rules were useful. Work hard. Stay alert. Be impressive. Be reliable. Don’t fall behind. Don’t rest until everything is handled.

Those rules may have helped you succeed. But are they still serving the life you want now?

The Background Process

Most of the strain people carry is not from what is happening. It is from what is running.

The half-made decision. The avoided conversation. The identity that says, I am the one who keeps everything from falling apart.

So even when you are with your spouse, you are not quite there. Even when you are with your kids, part of you is scanning. Even when the workday is over, the system is still on, wondering about tomorrow, wondering about what you forgot.

And because it has been running for so long, you stop noticing it. You just call it “busy.”

But some of what feels like busyness is unresolved attention. Some of what feels like pressure is loyalty to an old rule. Some of what feels like responsibility is fear wearing a more respectable suit.

What If It Could Be Easier?

When I ask a client, “What if it could be easier?” I am asking them to look at whether the strain is producing what they think it is. Whether the urgency is necessary. Whether the relentless version of themselves is truly wise, or just familiar.

Is the person who can never sit still, never exhale, never enjoy a simple cup of tea, actually a high performer? Or are they just someone who has forgotten that they built this life and they can still choose how to live inside it?

You can make the phone call. You can have the conversation. You can move forward and adjust if you’re wrong. You can stop carrying decisions you have already made. You can stop treating every stray thought as a new assignment.

Can you simply take a moment and see what happens?

Often, when the mind gets quiet enough, the next thing is obvious: make the call, send the note, take the walk, close the laptop, tell the truth, drink the tea.

One Cup of Tea

It starts smaller than the mind wants it to.

One cup of tea. One moment on the deck. One breath before the next meeting. One honest question:

What am I treating as urgent that may only be familiar?

And then another:

What would become obvious if I stopped arguing with life for thirty seconds?

The cup in your hand. The light on the floor. The life you already have.

Seen.

From there, the next step usually appears.

Honor that next thing. Take the next step. Repeat.

Just life.

Just a little bit easier.

Any maybe a little more worth living. No matter what you choose to build.

Going Deeper

If you want to take the next step with less hesitation, sign up for my free Pick Now Decision Sprint here.

https://mailchi.mp/c26f62666ec4/the-pick-now-decision-sprint

And get the deeper version of these articles, too.

It can be easier. But you have to let it be, first.

In April 2023, I picked up my son’s alto saxophone and took my first lesson.

This past Friday, I performed in public for the fifth time. An eight-piece band — Dire Straits, Pearl Jam, the Eagles, the Rolling Stones. The set closed with a two-minute sax solo. It was mine.

I play tenor now. I am not yet good. I am much better.

That distinction matters. In fact, it is everything.

Improving is Not About Perfection

I love the process of improving. It’s not clean. In fact it can be incredibly unpredictable.

One of the strangest thrills I’ve discovered is screwing up on stage and recovering in real time, surrounded by people I’ve practiced with for months.

That used to terrify me. Now it’s oddly satisfying.

Because that’s the real skill, isn’t it? Not perfection. Recovery.

The capacity to lose the thread, find it again, and keep playing.

That is music. That is leadership. That is life.

Happy (and Never Satisfied)

Was I happy after the show? Incredibly.

Was I satisfied? Never.

There is always more to learn. Always more to practice. Always something I could have played better.

But if you only measure yourself against where you are going, you will always feel behind.

So I try to pay attention to two things.

First, how far I’ve come.

Second, the occasional moments of bliss along the way.

I cherish the moments when I forget myself and the music is just happening. When the band locks in. When nobody is thinking. When the song plays us.

There’s nothing quite like it.

I enjoy the practice. The practice is necessary. The bliss is the gift.

Forever a Beginner

I will never be an expert. I started at 58. But I can get better. I can pull more satisfaction out of my playing every year for the rest of my life.

That’s enough.

Actually, I think that’s the point.

There Is No Hack

Early on, I was talking to a friend a little older than me. He was winding down his business and had more free time.

He told me he had always wanted to learn guitar.

I told him what I was discovering — the strange joy of going back to the beginning with something I loved.

I asked him if he thought he might start playing guitar. He said: “I’m not willing to suck for two years.”

He couldn’t remember the last time he had done something where he wasn’t already competent.

And I remember thinking: Then you’ll never feel this.

Not because he lacked talent. Because he wasn’t willing to begin.

Whatever you actually want — the band, the book, the company, the relationship, the conversation you’ve been avoiding — there will be a stretch where you suck.

There is no hack for that.

The willingness to suck is the price of admission.

At my first concert, I spent the first song and a half trying to get something, anything, to come out of my horn. Mostly squeaks. Then I finally got my footing and played something. Badly out of tune. Because that’s where I was.

Last Friday, I improvised a two-minute solo. Mostly with good tone. Mostly in tune. (Or at least much more in tune than that first time.)

As my teacher says, there is no substitute for playing in front of people.

And there is no substitute for what that teaches you about yourself.

So here’s the question:

What are you not willing to suck at?

And what is that costing you?

Stuck Deciding?

Hesitating to move forward on something you know you want to do?

Try this for thirty days, and watch everything change:

The Pick Now Decision Sprint

#PickNow

A client of mine (let’s call him Blake) has been trying to hire an assistant for months. Someone who can help him across three enterprises.

He’s interviewed candidates. He’s run personality assessments. He has someone he genuinely feels good about.

There is no new information coming.

Meanwhile, he’s still making last-minute travel bookings. Still dropping balls. Still carrying the low-grade fear that never quite shuts off: What have I forgotten?

I asked him a question I’ve been holding for weeks.

“I notice you keep not hiring an assistant. Do you know why?”

He didn’t answer right away.

Which was the answer.

Pick Now Isn’t Really About Action

It looks like an action tool. Make the choice. Stop deliberating. Move.

But underneath that, Pick Now is a flashlight. And the question “Why am I not picking?” is what turns it on.

When Blake stays with that question, four levels of answer become available. Each one more true than the last.

The first level is the situation.

This is where the logical reasons live. Blake has three.

The training time. “I’d lose more hours getting someone up to speed than I’d save in the first quarter.”

The wrong-hire risk. “The cost of a bad hire is huge. Better to wait than to redo it.”

The financial commitment. “I’m not at peak revenue yet. I should hire from strength, not from need.”

Each one sounds reasonable on its face. Each one dissolves when you look more closely.

The training time? He’s already spending more hours than that on the things an assistant would handle — and he’s doing them in the worst possible window: late at night, sleep-deprived, rushed, and resentful.

The wrong-hire risk? He has a candidate he genuinely feels good about. He’s done the diligence. At this point, the biggest risk is no longer the unknown candidate. It’s the unhired one.

The financial commitment? Before peak is exactly when you hire; it frees up the capacity that helps create the peak. Hiring after the peak means doing the peak alone.

Which is what he’s already doing. Poorly.

That’s how the first level works. The reasons sound rational until you put weight on them. Then they collapse, and you’re standing on the second level.

The second level is the pattern. This is where the answer becomes: I do this. Not just here. Anywhere there’s a consequential decision, I find a way to keep the door open.

This level is heavier than the first because it can’t be retired by hiring one assistant. It travels.

It shows up in hiring. In sales. In relationships. In strategy. In any place where choosing one thing means letting go of the fantasy of every other thing.

The third level is the engine. Why does this pattern keep running? What is he avoiding? What is he afraid to admit?

Maybe it’s fear of making a mistake. Maybe it’s fear of losing control. Maybe it’s fear that someone else could do something better than he can.

Maybe it’s fear that if the easy things come off his plate, he’ll be left with the harder work he’s been avoiding.

Usually, it’s not one clean thing. It’s a knot.

And then there’s the fourth level.

Identity.

This is the one most leaders would rather not look at. Because the fear isn’t always about making the wrong decision. Sometimes it’s about making the right one.

Who will Blake have to become if he hires the assistant? What can he no longer hide behind?

If he has an assistant, someone else can handle a lot of the things he has been using to feel necessary. Someone else can book the travel. Track the details. Remember the loose ends. Protect the edges (and the calendar).

Which means Blake has to face the work only he can do. The strategic work. The relational work. The creative work. Actually working on the business rather than in it.

And maybe that’s the real threat.

Not that the assistant will fail. That the assistant will succeed.

Because if someone else can hold what Blake has been convinced only he can hold, then the whole identity starts to wobble. The version of him that has been valuable because he is indispensable begins to lose its job.

That’s where the actual weight sits. That’s why he can’t pick.

Not because the candidate is wrong. Because picking would change who Blake gets to be.

One Question. Four Levels of Answer.

The point of the question wasn’t to get Blake to answer me in the moment.

The point was to start the question working on him after I left.

A leader who has been deferring a decision for months usually doesn’t need more information.

He needs the question that turns the deferring itself into the data.

If you’ve been “still thinking about it” longer than the situation requires — and most of us are, on something, right now — try the question on yourself:

Why am I really waiting?

Sit with it. Give it time.

The first answer will be about the situation.

The fourth answer will be about you.

Want Access to Pick Now?

Here’s how you can get it.

https://mailchi.mp/c26f62666ec4/the-pick-now-decision-sprint

It’s not just a tool. It’s a way to shine a light on how you keep holding yourself back.