Destroy the idea that you have to be constantly working or grinding in order to be successful. Embrace the concept that rest, recovery, and reflection are essential parts of the progress towards a successful and happy life.
- Zach Galifianakis

We were 20 minutes into a coaching session aimed at sharpening my client's company's goals for the year. I was challenging her to begin by zooming way out.

"What do you most want to have achieved 10 years from now?" I asked.

"I want us to have built one of the definitive brands in our space," she replied.

"What would having that give you?" I asked.

"We will have made a difference. We will have built something lasting."

Because we had been working together for the better part of a year, she knew I was not going to let her off the hook that easily.

"Let's start with you for a moment. I want to know why it matters to you. What would having that give you?"

I watched her eyes fill with tears.

She brought us back to earlier conversations we had had about her childhood. About the times she had felt like an outcast in social settings. About how out of place she had felt growing up.

"Then I will know I have made it. That I am valuable. That I matter."

We shifted focus over the next portion of the session. Suddenly, instead of talking about the company's goals for the year, we were getting to much more foundational footing.

I asked her, "So we are going to spend the next 10 years building this company so that you can prove to the world that you are enough, that you matter?"

She broke into a smile. Smiling through her tears.

"Yes. That sounds right."

"Do you see any problems with that plan?" I asked, an admittedly leading question which I typically try to avoid in coaching.

"Yes," she said. "I am seeing that there is no way I can do this job for 10 years if I am questioning all along the way whether I am good enough."

A ha.

And there's the rub.

We founder/leader types are often drawn to the work because of some chip we carry on our shoulder.

I have heard venture capitalists brag they only like to fund founders who have a chip on their shoulder They seek out founders who carry some deep-seated need to prove something to the world.

I talk to many new founders every week. One of the funny and fascinating parts of being a CEO coach is that people reach out daily and typically on the very first call dive right into parts of their experience they might not tell their closest friends. It is an honor to witness and a hell of an education on founder psychology.

Starting a company is a very hard way to make a living.

Most of us are not drawn to it for the money. If you want to make a bunch of money, there are much easier ways to do it.

But if you are (subconsciously) carrying a need to prove yourself to the world, to show that you are different, special, and worthy of love and belonging, the role of startup founder can be deeply alluring.

This setup is shared by most of the founders I meet. Me included.

How we get here

By the time a leader is sitting in a coaching session with me exploring such questions, she has typically arrived at some point of awareness that the way she has been operating in her life and work, while at times greatly beneficial, is not going to help her arrive where she most desires to go.

Sometimes this awareness presents through curiosity and gradual personal growth; more often it shows up as depression, anxiety, or burnout. There are also leading indicators in the feedback we receive from cofounders, employees, or board members.

Before we can explore change, it is helpful to begin by looking at how we arrived here and how this way of being has served us in our lives to this point.

Most of the leaders I meet are type-A, high-achieving types. And most faced some kind of childhood challenge or inequity.

It may be challenging family of origin dynamics or a feeling of not fitting in within the school or social setting in which one was raised.

At some point, many of us realize that our academic (and later our professional) performance is a way out of the inequity we have experienced.

In my case, I really struggled in elementary school. A couple of years being overweight and shy left me with a deep feeling I did not fit in. That is a message that still comes to my mind sometimes when walking in to a room of strangers. Networking events are my nightmare. Although you would never know it watching from the outside (I fake it well).

I also grew up with a dad who deeply loved me but lacked the emotional resources to show that love to me in the ways I deeply desired. He had been a star athlete and deeply desired I follow in his footsteps. That dream died when I got cut from the JV basketball team and found I deeply disliked football. A failed midwestern adolescent if ever there was one!

When I discovered I had a knack for excelling at academics, I found a path to being unique, accepted, and valued by both my peers and my father. That model of earning acceptance though achievement carried well into my adult work life.

For those of us who come up this way and arrive in adulthood excelling in our work but still carrying the wounds of childhood, there is a risky setup.

Particularly as we take on leadership roles.

As a result of such success, when we begin to explore what feels to us like an obvious next step, starting our own company or taking on another leadership role, others are willing enough to work with us and for us and often to give us capital to make the whole thing happen.

But this setup is a ticking time bomb.

Hitting the wall

Three years into starting my last business, I began working with my first CEO coach. As a part of the kickoff, he encouraged me to do a 360 review. His firm would speak with 10-12 stakeholders (a mix of my cofounders, employees, and board members). The goal was an honest assessment of my strengths and weaknesses as a leader.

I was intrigued. And nervous.

When I received the ten page report, I was aghast. Much of the feedback was positive, but like every perfectionist I promptly honed in on the negative feedback.

I learned that my co-founders and team members often found me physically present but emotionally or mentally absent.

They felt it was hard to get my full attention. When they brought problems or challenges to me, I had little tolerance for hearing their experience and wanted to move quickly to finding solutions and moving on.

As I look back at that feedback, I realize I was failing at one of the most critical parts of my job.

I was unable to hold space for my team members and to support them as a partner and ally on the hardest days. I did not have the requisite footing to do so because I was suffering myself.

My own attachment to the trajectory of the business rendered me unable to be fully present with the team when they needed me most. Rather than being a grounding partner, I was experiencing the ride more than anyone else.

Looking back, the reason I was so very on the ride was that there was way to much at stake for me. It was not only my financial well-being and my professional reputation, it was my sense of survival.

My sense of belonging and of being worthy of love were wrapped into the performance of the company.

With the help of my coach, therapist, and friends, I began a long exploration of decoupling my sense of worth from my work. Today, I would say I am 75% of the way to where I would like to be.

There is still a lot of work to be done.

What I learned through the ensuing 4 years I was in the CEO role, and what I am continuing to see in my coaching work with other CEOs and leaders, is that this work is deeply necessary.

I do not believe it is possible to show up as an effective leader and partner until you do the work of separating your sense of worth from your work.

Superpower or kryptonite?

Many founders find their way to me when they are right at the point of realizing that the way they have been operating is not going to work anymore.

In our early discussions, we might explore some of the questions I began exploring with my own coach following that 360 feedback. For me, the questions looked something like this:

  • If my work cannot prove I am enough, what can?
  • If I begin to explore a different, deeper sense of self-worth, will I lose my edge in my work? Will I fail to care?
  • Where do I even begin?

As you are reading this post, before I invite you in to my own experience, I would invite you to take a moment with the following questions for yourself:

  • How would you show up in your work if you were entirely free of the story that your value is tied to your work?
  • If you achieved all you now desire to do and prove in your life, if you earned all the money and received all the acclaim you desire, what would you do next? How would you spend the next 10 years?

The cost of not doing the work

In my own time as CEO, I came to see that the drive to succeed, or this chip on my shoulder, had greatly served me in my life. But it was crippling me as a leader.

The drive had enabled me to succeed in school and my early career. Those accomplishments set me up to start my own business and got me in the door with leading venture capitalists.

But as evidenced by my 360 review, there was a growing disconnect between the way I was showing up in the office and what my team deeply needed from me as a leader and partner.

I began to get curious about the way others tackled the challenges of finding a healthy or necessary sense of separation from their work.

I found it most helpful to look beyond tech, beyond beyond entrepreneurship, and beyond business.

I found the book Daily Rituals: How Artists Work deeply helpful. I came to see most of the greats carved out portions of their days for their craft but left much of their life open and separate from their work.

I knew I wanted to find a different way of relating to my work. And I knew my company needed such change from me.

What follows are my reflections on what aided the evolution (which as noted continues even today) from where I found myself six years ago toward the entrepreneur and creator I deeply desired to be.

Moving toward a new way

Loyal soldiers

When I realized I needed a change, my first impulse was to turn to guilt around the way I had been.

But my coach at the time suggested a different route that proved much more fruitful.

My coach introduced me to a concept commonly leveraged in coaching known as The Loyal Soldier.

The idea is taken from what occurred with Japanese soldiers at the end of World War II. In short, many Japanese soldiers were sent out during the war to guard the empire's islands far from the homeland.

When the war ended, many such soldiers never received the news the war was over.

They thus kept guard at their islands, refusing news from the locals of the end of the war which they took to be a trick form the enemy.

Only when Japan began to locate these soldiers, approach them thoughtfully and carefully, and invite them back to the motherland to be celebrated and reintegrated, did the war fully end for these men.

I came to see that much of my perfectionism and intense work ethic were in effect my own loyal soldiers.

These were ways I learned to keep myself safe during times when life felt more like war than peace.

When I looked back at my 15 year old self, I realized my straight-A's were a way out of a dangerous and painful family dynamic. I left high school after my junior year and shortly thereafter was largely emotionally and financially independent from my family.

My soldiers were effective.

But now, 17 years later, the war was over and it was time for them to lay down their arms.

Their service was now getting in the way of my ability to show up as the leader I wanted and needed to be.

So I began the process of inviting my soldiers home.

You were born for this

As I began to explore how many of the artists and writers I admired approached their work, I thought their practices might hold the secret to my path changing my relationship with my own work.

The biggest unlock turned out to be a lot closer to home.

During my early years running my last business, I became a father for the first time.

My son, Marco, became my greatest teacher on self worth.

What I noticed as I watched him progress through his early childhood was that he never questioned his worth.

He doesn't learn or create because he needs to prove he is worthwhile.

He simply is.

And it is magical to watch.

He is fully in the moment, utterly happy with himself, and deeply curious about the world around him.

I came to see and believe that I had once been just like Marco. And whatever had come to separate me from that way of being, somewhere inside me was the knowledge of how to be that way in my own life.

I was not broken.

I did not need to find my way to fixing myself.

Yes, I had spent many years with my loyal soldiers fighting my war on my behalf.

But now that it was peacetime, I did not need to learn a new way of being.

I simply had to return to a way I had already been.

That was a big shift for me.

From there to here

It was not an overnight shift. But I slowly began the process of exploring and celebrating my own goodness.

I started to take myself to dinner every month or to to celebrate my life.

Each morning, after a short meditation, I began to give myself a big hug and share my deep approval for the way I was showing up in my life.

I began writing letters and recording audio messages to myself reflecting on what a wondrous life I was living.

With the help of my therapist and coach, I continued to unpack the negative messages I carried. To find space from them and to examine them with curiosity instead of suffering.

Life is not perfect now.

I still have days where depression, anxiety, and self-doubt are present.

But there is a lot more space.

When the depression is present, I can often see it, even welcome it. Knowing it will stay while and then depart. Even at moments holding gratitude for the way it keeps me in touch with the human of experience and allows me to show up with empathy and compassion for clients facing their own dark days.

While every day is not bliss, there are a lot more good days now.

And work is really fucking different.

For the first time since childhood, I now find myself more days than not engaging in my work as play.

As a coach, finding a sense of separation between my own identity and the ups and downs of the work is critical. I cannot hold space for you if I am reacting to everything you share out of own ego.

When we sold my last business, I was not sure I would ever build anything again. For too long, I married the act of creating with the need to prove my worthiness.

But recently, I have been creating from an entirely new place.

I have found myself able to write without worrying who reads or what they think.

And I have returned to building software from a place of curiosity and creativity. It feels wondrously different.

I wish the change had come faster.

Finding a new edge

I regret the pain I caused as a CEO during the years I was too wrapped around my own suffering to see the impact it had on those around me.

I wish I had been able to hold space and curiosity for the many employees who came and left our startup in those early years.

Things were better during the second half of my tenure. And for that I owe tremendous gratitude to my coach, therapist, and the many friends and mentors who helped me through.

As I learned to step into self-acceptance, I too held the fear I might lose my edge.

I had the contrary experience.

Tying my sense of self to the performance of the business drove me toward burnout which I have written about at length.

Finding a sense of separation helped me to approach my later years as CEO from a place of curiosity and creativity. In those years, in spite of laying off 80% of our staff, we managed to 5x our revenue and sell the company.

With the assistance of each person on our team, together we were able to stave off anxiety and fear and to get deeply creative in our approach to surviving and thriving.

I have found that each step toward well-being and self-acceptance has led me toward better work, more creativity, more energy, and greater purpose.

The opportunity at hand

What about you?

What is it costing you as you read this piece today to hold your sense of self so closely to the outcome of your work?

How would you approach your craft if you were utterly free of the story that you matter so long as your work is well-received?

If you are sitting with these questions and in need of support, I would love to hear from you.

Rarely in history have we been more in need of leaders able to lead from a place of wholeness and capable of inviting others into that experience.

You are not alone.

With love from Venice, California.

Matt