Building on the Other Side of Burnout

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I needed hope

It was 8 PM at night. The only open slot the therapist had that fit into my busy life running a venture-backed startup and trying to keep a newborn baby alive. It must have been wintertime as it was already pitch-black outside. I remember parking urgently, late for the appointment, and struggling to find my way through the sprawling 1970s-style California office building.

I was too busy for therapy. During those years, I said no to everything that wasn’t materially relevant to the day-to-day survival of my child or my startup. But I needed therapy. Or at least I needed hope.

The question that drove me to that office that evening was this: “Is it possible to have a job like this without so much suffering?”

As we sat down and began our first session—first of what would be hundreds of sessions over 5 years — I gave my would-be therapist the following context:

I am in a high-stress, high-stakes job. I have always been in jobs like these, and I think I would like to always be in jobs like these. But I also cannot keep living like this. Can you help me?

That question began a journey in my life of exploring whether there was any other way to approach high-stakes work.

A sliver of light

If you have followed my writing, you know things did not improve overnight. A few years later, I was in a state of deep burnout. I was disconnected from the mission of my own company, heartbroken by losses in life and business, and questioning daily how I might get out of the CEO role. More about that here if you are curious.

But change did come. After we scaled and sold that business five years ago, as I began my recovery, I was convinced I would eventually start something else. So much so that when I started coaching — which I initially viewed as a likely part-time, short-term thing — I named my coaching firm Sanity Labs. The idea was we would provide coaching support and also build products that would further our mission of helping leaders and teams to be more connected and effective. The coaching took off quickly, the building not so much.

There were a few false starts on getting back into building. But every time I got past a rough sketch or a few conversations, I could not continue. My body would tense up, my mind would scatter, or I would simply lose motivation. Some part of me felt deeply resistant to anything that smacked of building a startup. Like keeping my hand off a hot stove. I frankly did not know if I would ever build again.

I could coach; I loved it from the very first session.

I could write; I have found it a healing and connecting outlet.

But I could not build.

But finally, five years later, something has changed.

I am building again.

Building again

As I write those words, I can feel energy filling my chest. I feel joyful. I feel proud. I feel grateful.

Since I have written so much about my experience of burnout and the difficult years that ensued, I thought I would share today a few thoughts from what I am experiencing as the other side of a very long, dark tunnel.

This new exploratory effort has now far outlived the others. It is, of course, a brand-new product. So, there is every possibility that it could die in the water in a matter of weeks or months. But for right now, it is very much alive. And with each passing day, it seems to take on more of a life of its own. That is new - and magical.

I have written a great deal in the past about navigating burnout. You can find two those posts here and here.

Today, I thought I would instead begin an exploration of what it is to start again on the other side of burnout.

Not everyone needs a fresh start. In my experience, while the desire for a fresh start is nearly universal, when we probe beneath the surface, we often find that alignment, joy, and thriving can be found right where the one is. I have witnessed this numerous times as a coach. In my case, while the last few years of my last business were certainly a realignment and a reimagining of the role and work, I nonetheless found myself crossing the ‘finish line’ feeling smoked - needing a hard reset. I needed time, rest, and something different.

I did not know if I would ever build again.

The false starts have been so pronounced, even in the midst of exploring good ideas with great people, that if you had asked me a year ago if I would ever start another startup, I would have said “probably not.” So what is making this time different?

I have been asking myself that very question.

What is different this time around?

The Why

The first thing that feels profoundly different this time around is the “why” behind the work.

In the past, most of my efforts at building came from a place of needing to prove something: that I was enough, that I could do work that mattered, that I belonged. Or it came from a place of fear: that I would need to get a real job if this thing did not work out. Both of these are hard places from which to create — not impossible, but not easy.

By contrast, for the first time in my life, or at least since I was a child, I find myself creating and building from a place of curiosity and joy. I credit in part a series of books I read, on how artists think about creating, for helping give me language and context for how I hold the work now:

• The Artist’s Way by Julia Cameron
• Daily Rituals: How Artists Work by Mason Currey
• The Creative Act: A Way of Being by Rick Rubin

Studying artists - writers, poets, painters, etc. — helped me to envision a new way of creating. From a belief that an idea or product or piece wants to exist, and that the opportunity is to simply be a vehicle or willing participant in that creation.

That is where I find myself now.

I am creating because an idea has come my way that wants to exist, and I feel energy and excitement about being a partner to that idea.

The What

Closely related to this new way of experiencing the why behind the work is a new experience I am having around the “what.”

I am working on a product that is related to and an extension of work I already do and love. I wrote recently about my rediscovery of the power and mystery of questions. The product we are building, which you can learn more about here, helps people and teams ask better questions more easily and collaborate on answers more readily.

The mission of the product is to bring people into deeper connection and support. It is no coincidence this is the same mission I hold in my coaching work.

The Who

The “who” might be the most emerging part of the journey so far. I am working with a partner I have never worked with before. He is a good friend, but not one of my closest friends. He is a new friend. Someone my wife and I met fortuitously on a plane ride to Mexico. We spent an evening swapping stories over margaritas and tacos. It was clear the three of us would be good friends. And while I was not aiming to build anything at the time, I did have the thought: If I ever build something again, I would love to work with Chris.

I spent a couple of months noodling around on this particular idea before considering bringing a technical partner on. I think the pain and stress I experienced with my co-founders last time around—which I have written about openly here — left me wary of partnering up. But when Chris left his last company and was exploring what might be next, I could not get the idea out of my head of working together.

We had a few conversations about what mattered to us in what we might build next:

• Work being an expression of curiosity, joy, and authentic ambition.
• We both love life, adventure, friendship, and community — so whatever we worked on needed to support, not constrain, those parts of our lives. The work needed to be additive.
• We discussed our motivation.
• We discussed our goals for expression, for impact, and our financial goals.

We also talked openly about our preferred working styles.

We also spoke about our respective areas of expertise and zones of genius. We made agreements early about where we would collaborate and where we would trust each other to run on our own.

We even made some simple, nerdy, tactical agreements on how we would work, which I will share below.

The How

Rather than the presumptive we are all in killing ourselves mindset that is the default for most startups, we explored how we would most like to work. We agreed we wanted large blocks of focused time.

We would meet once a week for no longer than 45 minutes and walk through the following agenda:

• Check in (Red/Yellow/Green) (read more here)
• Progress on last week:
• What got done?
• What did we learn?
• What is blocked?
• What are our priorities this week?

Since we were now friends and colleagues, we agreed to dedicated communication channels: Slack for work messages, iMessage for friend messages. We also quickly developed the habit, when calling each other, of stating as soon as the other person picked up: “Hey bud, this is a [work] call.” Or, “Hey bud, this is a [friend] call.” What started as a joke quickly proved quite helpful.

Partnering with Chris is giving me a sense of freedom and energy in the project that I know I would not have alone. I feel supported, celebrated, and free to fail or succeed. I also feel free to work my ass off on some days and blow off work on others to take my wife to lunch or my kids to the beach.

Finding a great partner is hard. I’m grateful for the journey with this new partner so far.

Closing

More to come. But I think that is enough for today. I feel cognizant, sharing any of this, that (1) I am in the honeymoon phase of the project and the partnership, and (2) the whole thing could end in the next few weeks. That is the nature of any new project — especially new technical products and startups. But all of that feels okay.

I write frequently and openly about the most difficult parts of creating, building, and leading. I wanted to share a message of hope from the other side of deep creative burnout. I am experiencing firsthand that it is possible to fall in love again with the mysterious art of creating something from nothing. It is possible to choose to trust and risk leaning in with a new co-founder or partner, even if past roads have proven painful.

I plan to share more along the way as I (and we) continue this journey. If you would like to follow along, please subscribe here.

Looking for some support? If now is the time to consider coaching (or a CEO peer circle), reach out here.

If reading this, you find yourself on your own journey into, through, or on the other side of burnout, I would love to hear more. Please drop me a note.

In the meantime, sending a big hug your way from a fellow traveler.

-Matt