Most of my clients come to me at around $10 million of revenue. Sometimes $15 million if they got lucky, or were willing to work really hard.

Maybe you’re in that situation right now.

You hired an EOS implementer. You worked on time management. Delegation. You brought in senior people to lead key functions.

None of it worked. You’re working harder than ever and wondering what you did wrong.

Here’s why—

For a long time, everything running through you was your biggest strength. It’s how you put your stamp on it. Your client relationships. Your offerings. What actually makes you different from the other four companies bidding the same job.

Depending on the industry, that works up to about $15 million.

Then it turns, and it turns fast. The exact thing that was your advantage becomes the thing holding you down. You’ve built a business and a client base that needs you, and there isn’t enough you.

You’ve handed off plenty. The scheduling, the invoicing, the things that were never really yours.

But every time it’s something that actually matters, you take it back. The client who’s called your cell for eleven years. The bid that has to be right. The call that was easier to just take than to explain to someone else.

You have a reason every time. A good one. Usually a true one.

There’s a whole industry serving founders at this stage. EOS implementers, recruiters, time management consultants. Some of them are excellent, and your consultant probably isn’t wrong about anything he told you.

But every consultant is working the same problem: how to get more out of the same you.

And that you is already at your limit.

The same you who needs to be in the middle of it. The same you who will fight to give up as little as possible — and who can produce three legitimate business reasons for every one of those fights.

You’ve never had a bad reason. Not once. That isn’t good judgment — that’s the mechanism.

You know exactly what you’d have to hand over. You’ve known for two years.

What you don’t know is who’s left when you’re no longer holding it.

My mom is dying.

My father-in-law died in October 2020. I remember his last days well.

Love. Gratitude. “What did I do to deserve such a wonderful life?”

My mom is having a different experience.

As her heart fails, as she comes in and out of consciousness, she has been saying some revealing things.

“I wish I had more courage.”

“Why am I so afraid all the time?”

“I wish I knew how young I still was when your father died.”

She was 52. She’s now 90.

My mom lived a small, fearful life, which I observed mostly from afar. She has told me stories, while we sit together in a darkened hospital room for hours at a time, that remind me how deep her fear goes.

Her mother never taught her to clean her room. She always cleaned up after her, because my mom could never clean to suit her. Same for cooking. Everyone thought my grandmother was a wonderful cook.

My mom told me her mother paid her one compliment in her entire life. She remembered exactly what it was.

She was able to turn a cape into a skirt.

What she learned is that nothing she did was ever good enough. She passed parts of that on to me, though I somehow learned to try harder rather than give up.

She was afraid to learn to drive. My grandfather, and later my father, drove her everywhere.

She has lived alone, with very few friends, since my father died in 1988.

She lost her hearing years ago and was afraid to spend money on hearing aids. She moved into a retirement community in late 2022. It’s hard to make friends when you can’t hear them.

She has gradually lost her sight and is afraid of the cataract surgery. She can’t do the things she once loved. Reading, crossword puzzles, board games.

Therapy was not to be discussed. Medication, only very recently.

She lived a life full of anxiety and handled it by making her life smaller and smaller.

Yesterday she told me how much she wished she’d had a relationship with my children.

The ones whose visits she refused for years.

My father-in-law was afraid, too. But he threw himself into his fears.

From Navy pilot in his youth to Alaska Harley tours in his seventies.

I know which path I want. She never thought she was choosing.

The owner wasn’t sitting with me by himself.

His father was there, too.

Or at least everything his father had taught him.

“Stay in control. Do everything yourself. Keep the team small.”

He’d bought the business from his dad a few years back and had already grown it well past anything his father built. He was making more money than he ever thought he would.

He was also still doing all of it himself, and he was at his limit.

There was a partnership on the table. The kind that could substantially expand the business. He’d been turning it over for months.

I asked him what he was afraid of.

He was afraid of working even harder. He was afraid of losing control. He was afraid of all the things that his dad taught him to be afraid of.

And he was holding it. In his gut. In his tight shoulders.

“I got a good thing going. Why would I want to risk it?”

I hear that a lot. It sounds perfectly reasonable. Until the owner collapses from a combination of firefighting stress and soul-sucking boredom.

“I watched my dad do the same thing every day until it wore him down. He retired at 60 absolutely exhausted. I don’t want to be him.”

He was afraid of being like his father. But to be different went against everything that he had absorbed from him.

The decision was simple. Partner or not? Give it a try, or not?

But the weight went back decades.

Take a look at your to dos.

What’s the one where you just can’t quite move? The one that’s been sitting there for months?

What are you making that decision mean?

Not just to you. About you.

I’ll go into more detail on how to think about it in this week’s Substack. Subscribe here:

https://jeffmunn.substack.com

As you read this I’ve just started another two-day retreat. A client and me. Offsite. No structure. No agenda. No phones. Just being with whatever arises.

I learn as much from these as my clients do.

Mostly I learn what I instinctively do to make myself more comfortable.

Speaking to fill the silence.

Teaching to justify the fee.

Believing my client’s story that there’s a right path and a wrong one.

I’m writing this the day before we start, as a reminder that I don’t have to do any of it. I can just be in the space and enjoy it — and notice what shows up when either of us falls out of it.

Trying to predict a future we obviously can’t predict.

Defending an identity that nobody else is attacking.

Feeling a weight that, when you actually look at it, turns out to be made of the same stuff as the identity it’s attached to.

What we walk out with isn’t a plan. It’s the felt sense that this whole thing gets lighter the moment we stop believing we can grind, work, and think our way to certainty before taking a single step.

How boring would that be?

I’ll be writing more about the actual retreat later this week on Substack—

https://substack.com/@jeffmunn