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

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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.

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Here’s how you can get it.

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

I’m sitting with my mom in her nursing home in Iowa. Celebrating her 90th birthday.

And I’m unsettled.

Some of it is probably too much caffeine. Some of it is being back in an old emotional field. The kind where the body remembers things before the mind can explain them.

Memories of not quite being enough.

The gifts I gave that got returned.

The interests that got dismissed as strange.

The awkward attempts to become someone they’d finally approve of.

One memory came back hard.

Senior year of high school, I was playing offensive tackle on the football team. I was 5’11”, about 195 pounds, and had tried to make myself bigger so I could belong there.

It didn’t work.

I was too slow for guard and too small for tackle. The guy ahead of me was 6’5″ and 250.

I wasn’t going to start. I probably wasn’t going to play much at all.

I was just grinding through practice every day, waiting for the season — and my football career — to end.

At the same time, I sang bass in one of the best high school choirs in the country.

Our conductor approached me about playing a major role in the musical, Li’l Abner.

Earthquake McGoon. The villain.

Big part. Real opportunity.

I wanted it.

And I hid.

My father had a rule: if you start something, you finish it. So in my mind, quitting football wasn’t an option.

But that wasn’t really why I stayed.

I was more afraid of being seen as a musical kid than of wasting months pretending to be a football player.

The jocks were the cool kids. The choir kids were not.

And even though I fit much better with the choir kids, I wanted the approval that seemed to live somewhere else.

That’s what came back this morning.

I wasn’t choosing football.

I was choosing an identity I thought would make me acceptable.

And I’d keep doing that for a long time.

Get the grades. Go to the right school. Join the right law firm. Bill the hours.

Take the next approved step.

From the outside, it looked like ambition.

From the inside, it was compliance wearing a good suit.

That pattern ran me for decades.

Until I finally saw it.

Once you see the rules clearly, you stop mistaking the mask for yourself. And finally you can choose something different.

My mom and I are in a much better place today. But the memory remains. The decades I spent making myself look like I thought others wanted me to.

It was exhausting. And in a moment at my mom’s kitchen table, I heard the echoes that are still there.

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