EP 392 - [EON] Stop Filling Holes That Don’t Exist: The Hill Is Already Under Your Feet | Paper Napkin Wisdom

There are six years of my life that I have occasionally looked at as missing.

Around 2018 and 2019, things at home changed. My family needed more of me than I had been giving, and not in some abstract work-life-balance sense. They needed my attention. They needed my presence. They needed me to be there in a way that made continuing to push at the same pace impossible.

So I stepped back.

At the time, Paper Napkin Wisdom was doing extremely well. The podcast was frequently appearing in top charts around the world. The audience was growing, the conversations were growing, and there was real momentum around what I was building.

Then I stopped pressing on the accelerator.

Over the next six years, a lot happened in podcasting. The medium exploded. People whose shows had been behind mine went on to become some of the biggest names in the industry. Entire businesses and media companies were built around podcasts in ways that were difficult to imagine when many of us started.

Every once in a while, I would look at one of those people and wonder.

Where would I be if I had never stepped away?

The Strange Mathematics of Regret

The mind is very good at creating an alternate version of history.

In that version, I never stepped back. My family never needed more of me. Every opportunity compounded. Every decision worked. The audience kept growing. The business kept growing. Somehow, in this imaginary timeline, I also avoided all the mistakes, distractions and bad decisions that are part of every real entrepreneurial life.

Then I compare the real version of myself to that imaginary person.

Of course I come up short.

What makes this comparison so dangerous is that it does not feel irrational. It feels like analysis. It feels like I am simply looking at where I was, looking at where other people were, and estimating where I might have ended up.

But I am not comparing two real outcomes.

One side of the equation happened.

The other one never did.

That distinction matters because I began carrying the result of that imaginary calculation into the way I worked today.

When “Catching Up” Becomes a Way of Working

I have a high capacity for pressure.

That has served me throughout my life. When something needs attention, I can focus on it. When something needs more energy, I can usually find more. When I believe something matters, I am very capable of going hard at it for a long time.

But pressure is not always commitment.

Sometimes pressure is repayment.

I started noticing the language I would use in my own head. I needed to move faster. I needed to make up ground. I needed to get Paper Napkin Wisdom back to where it could have been.

“Make up ground” is an interesting phrase.

It assumes the ground is missing.

Once I believe there is a hole behind me, the natural response is to start working harder in front of me. I add activity. I add urgency. I push harder.

The problem is that there is no point at which the imaginary life tells me I have finally caught up.

There is no finish line.

A Conversation With Stephen Sisler

This week I was sitting with Stephen Sisler.

Stephen is an axiologist. Much of his work has been devoted to understanding behaviour, motivation, and the forces underneath the choices people make.

During our conversation, I found myself talking about these gaps again. The years. The opportunities. The things that might have happened if I had continued driving the business the way I had before.

Stephen told me a story.

The story itself mattered, but what really stopped me was the picture it created in my mind.

I suddenly realized that I had spent years occasionally looking backward and seeing a hole.

Then I would turn around and run harder, trying to fill it.

More work. More projects. More pressure.

Except there was no hole.

The six years were not empty.

They were full.

The Hill Under My Feet

During those years, I was exactly where I needed to be.

I was with my family at a time when they needed me most. I was being a father. I was being a husband. I was present for moments that were happening once and were never going to wait until the business became more convenient.

Those years went somewhere.

That is the distinction I had been missing.

I did not lose six years.

I spent six years.

I spent them on my family.

That does not mean there was no business cost. There absolutely was. Things passed me by. Opportunities disappeared. Paper Napkin Wisdom might be much larger today if I had kept pushing.

All of that can be true without turning those years into a mistake.

Opportunity cost and life debt are not the same thing.

An opportunity cost means I chose one thing and, by definition, gave up something else.

A life debt says I now owe the future because of that choice.

That was the debt I had been trying to repay.

The Life You Never Lived Can Become a Very Demanding Boss

Most people think comparison means looking sideways at somebody else.

I think accomplished entrepreneurs often face another version that can be even more powerful.

We compare ourselves to the person we believe we would have become if one important decision had gone differently.

That person has a remarkable advantage.

They never had to live the consequences of the choice we imagine for them.

They get all of the upside and none of the cost.

I can imagine the enormous podcast I might have built. I do not have to imagine what continuing at that pace might have cost my family, because that part does not fit neatly into the fantasy.

I can imagine six years of uninterrupted business growth without having to imagine exhaustion, mistakes, missed moments at home, changing markets or opportunities that looked good and turned out badly.

The imaginary timeline only shows us what we might have gained.

It rarely shows us what we might have lost.

That is why it is such a poor place from which to judge the life we actually lived.

This Is What Align Looks Like

I have spent a lot of time writing about Focus, Align, Act.

Focus is about becoming clear on what I want and where I am going. Act is about committing fully to what I can do now.

Align is the part in the middle.

It asks me to be honest about where I actually am.

Not where I thought I would be.

Not where someone else is.

Not where the fictional version of me would be if life had gone exactly according to plan.

Here.

Now.

And part of Align is being able to appreciate the ground that already exists beneath me before I demand that it take me somewhere else.

That does not weaken ambition.

I still want to build.

I want Paper Napkin Wisdom to grow. I want the new book to reach people. I have businesses I care about, work I am excited by, and things I still want to create.

But there is a profound difference between building the next chapter because I can see something I want to create and building it because I am trying to erase the last chapter.

One comes from possibility.

The other comes from deficit.

“I Should Be Further Ahead”

I hear this sentence all the time from people who have built substantial businesses.

“I should be further ahead.”

It usually goes unchallenged, as though “further ahead” were an objective location printed on a map.

Further ahead than what?

The business plan from ten years ago?

The competitor who made completely different life decisions?

The version of ourselves who never had a child who needed us, a parent who became ill, a partnership that ended, a market that collapsed, or a life that changed direction?

Sometimes “I should be further ahead” contains useful information. Maybe fear stopped us. Maybe we avoided a difficult decision. Maybe we did know what needed to happen and kept refusing to do it.

That deserves attention.

But sometimes the years that did not compound on the balance sheet compounded somewhere else.

In relationships.

In perspective.

In the people we became.

In the fact that the people closest to us know we were there.

That belongs in the accounting too.

Five Things I’m Taking From This

Opportunity Cost Is Not a Debt

Every meaningful decision costs something. That is what choosing means.

I can acknowledge that stepping back affected the growth of Paper Napkin Wisdom without deciding that those years now need to be repaid. The more useful question is not, “How do I recover that time?” It is, “What did that time create?”

There is probably a chapter in most entrepreneurial lives that has been labelled as lost. It might be worth looking at it again and asking what was actually being built during those years.

The Imaginary Version of Me Will Always Win

The version of me who never stepped away is impossible to compete with because he never encounters friction.

He benefits from every good assumption I make about the past and suffers none of the consequences.

Whenever I catch myself thinking that I should be further ahead, I now have another question available: compared with whom?

Sometimes the answer is a real person.

Sometimes it is somebody who never existed.

More Pressure Is Not Always More Commitment

Two people can be working equally hard for completely different reasons.

One may be building something they deeply want. The other may be trying to outrun the feeling that they are behind.

That distinction is almost invisible from the outside, but it changes the experience of the work.

Before I add more pressure, I want to know what the pressure is for.

Appreciation Gives Ambition a Floor

For a long time, I worried that appreciating where I was might make me complacent.

I think the opposite is true.

When I can acknowledge the hill already underneath my feet, the next goal no longer has to prove that the last twenty years mattered. I can pursue it because I want it, rather than because my identity depends on reaching it.

That creates a very different kind of ambition.

The Next Chapter Does Not Have to Fix the Last One

This may be the part I am sitting with most.

I do not need to build the next version of Paper Napkin Wisdom to prove that stepping back was wrong.

I do not need to reclaim six years.

I do not need to catch the life that never happened.

I can simply build from here.

Five Key Takeaways

1. Regret Compares a Real Life to One That Never Happened

The mind invents a version where nothing was given up. Only one side of that comparison ever happened.

Take Action: Write down the version of events you have been measuring yourself against, then mark the parts that never happened.

1. Pressure Can Look Like Commitment and Still Be a Debt You Invented

Pressure is not proof of commitment. Some of it is repayment on a debt you invented.

Take Action: Name one thing you are pushing on this week only to catch up, then stop pushing on it.

3. Stepping Back for Family Builds Ground That No Chart Records

The years you gave to people who needed you built something. No ranking records it, and it is still there.

Take Action: List what one so called lost season actually built, counted in people rather than numbers.

4. The Comparison Feels Like Analysis, Which Is What Makes It Dangerous

It arrives dressed as clear thinking. That is why it is rarely questioned.

Take Action: The next time the comparison arrives, ask whether both sides of it are real.

5. You Cannot Fall Behind a Version of Yourself That Never Existed

There is no distance to close. The other runner was never on the course.

Take Action: Choose one thing to build from here rather than to make up for, then release the result.

If I Drew This on a Napkin

If I drew this on a napkin, I would draw a person standing on top of a hill.

Behind them would be a faint outline of the hole they keep turning around to find.

Above it:

STOP FILLING HOLES THAT DON’T EXIST.

And underneath their feet:

The hill is already under your feet.

For years, I occasionally looked backward at those six years and saw distance.

Now I see ground.

The family I was there for. The relationships I protected. The person I became. The perspective I carry into everything I am building now.

None of that appears on a podcast chart.

It is still there.

Maybe there is a chapter in your life you have been trying to repay.

What if it was never a hole at all?

What if it is part of the hill you are standing on?

🎙️ This is an Edge of the Napkin episode, Govindh's solo series on Paper Napkin Wisdom.

Explore all episodes and the full napkin collection at:

Five Key Takeaways

1. Regret Compares a Real Life to One That Never Happened

The mind invents a version where nothing was given up. Only one side of that comparison ever happened.

Take Action: Write down the version of events you have been measuring yourself against, then mark the parts that never happened.

2. Pressure Can Look Like Commitment and Still Be a Debt You Invented

Pressure is not proof of commitment. Some of it is repayment on a debt you invented.

Take Action: Name one thing you are pushing on this week only to catch up, then stop pushing on it.

3. Stepping Back for Family Builds Ground That No Chart Records

The years you gave to people who needed you built something. No ranking records it, and it is still there.

Take Action: List what one so called lost season actually built, counted in people rather than numbers.

4. The Comparison Feels Like Analysis, Which Is What Makes It Dangerous

It arrives dressed as clear thinking. That is why it is rarely questioned.

Take Action: The next time the comparison arrives, ask whether both sides of it are real.

5. You Cannot Fall Behind a Version of Yourself That Never Existed

There is no distance to close. The other runner was never on the course.

Take Action: Choose one thing to build from here rather than to make up for, then release the result.