TLDR: I actually expected to get depressed, it still surprised me when it finally happened and I'm rather suspicious of its apparent resolution.

A few weeks ago, I couldn't focus, get stuff done, or even remember simple things. Work felt purposeless. Relationships seemed shallow and fleeting. I couldn't get more than nominally excited about things I'd normally jump to do. I felt like a ship drifting without an anchor, unable to latch onto anything for stability despite the supposed familiarity of the surrounding landmarks. All the usual ways I might find comfort — leaning on community, taking pleasure in the challenge of work, experiencing the wonder of the outdoors — were bereft of their power.

It sucked and it had been building for months.

For the last couple of years, I've kept a wary eye on my mental health. You probably know that I'm an incessantly optimistic ball of energy, particularly when you're still groggy from lack of coffee in the morning. I have a high natural frequency and, for the last several years, I've chased the high-energy thrill of starting a business with reckless abandon. At the same time, I've also been keenly aware of the phenomenon of "Startup Depression". I've seen a number of friends spiral, sometimes for many months, through deep bouts of depression that seem to counterbalance their otherwise ebullient energy.

I've never been depressed before and always felt like natural positivity, rational thinking and optimism provided ample shields against it. But some of the cases I read or heard about seemed to come out of nowhere, almost like the body's chemistry had to swing the pendulum back from all the energy and enthusiasm of a naturally high spirit. It was alarming to know how unexpected and almost inevitable it seemed.

Onset

Despite knowing that something similar might happen to me, I was surprised when it started creeping in earlier this summer and I didn't notice it happening at first. The burnout periods, a fact of entrepreneurial life, got more frequent. I began to feel trapped by location, relationships the never ending needs of the business and the very passage of time itself. Put another way, I had a growing craving for freedom (which is one of my core values) that wasn't being met.

I experience the world in two very strong ways — emotionally and intellectually.

For the emotional side, I've worked hard to open myself up to becoming more emotive, expressive, and simply joyful about the world around me. That also means leaning into the negative emotions like sadness and disappointment to acknowledge them and let them provide contrast against the positives.

For the intellectual side, I've long held a highly pragmatic philosophy of assuming that you only get one life and you should use it to live joyfully and to try and help lots of other people along the way. This philosophy has pushed me to try and improve how I experience the world personally and to do more to help those around me through a utilitarian application of skills to causes that matter. It's why we're doing what we do at Viking.

How did this spin south? I'm not sure I can provide an exact timeline, but I definitely fell under assault on both fronts.

I didn't notice how the feelings of compression and stress built up over time and began to smother some of the highs and lows I felt emotionally. That was the insidious part. I could tell that I was stressed and some of its symptoms, but not sense how it had begun to permeate the rest of my being.

I certainly noticed how I couldn't stop focusing on the passage of time and how poorly it seemed to be used. I felt stressed not just about having little time, but about my life slipping meaninglessly away. About being in a business that had lost some of its luster after the idealistic enthusiasm of the founding days. About not maximizing my relationships or my weekends or my thoughts. At 31, I can no longer run around with a blank slate to "live free and think about it tomorrow". This sense weighed on me.

I didn't notice until it was too late how negative my self-voice had become. Again, I think of myself as happy and confident. I found myself becoming more critical and "judgy" of others in my head and it wasn't until it applied to my romantic relationship that I was forced to understand the truth of the expression that "how we treat others is a reflection of how we treat ourselves". I not only had to admit that I was actually highly critical of myself and painfully aware of the distance between my "ideal" self and who/where I actually am, but I had to question whether, contrary to my most casual of assumptions, I actually even loved myself.

Woah. I can say that the very thought of that rocked me pretty hard. The mooring lines were beginning to fray…

Bad news came in over the summer with a drumbeat that the hale mind can easily defer but my well of optimism felt low and far away.

It was small and large. Some students canceled their subscriptions, stalling upward momentum in a new initiative. I watched a documentary on the history of the Middle East and was left saddened by human capacity for savagery and revenge. My grandfather passed away after a long and full life of 96 years. I saw a picture of a sad looking cow in a factory farm and suddenly was exposed fully to the hypocrisy of eating meat and living ethically, something I'd been able to shield myself from somehow through willful ignorance and… I don't know. I began to change my eating habits.

I also began to Question. Not just surface level things, but far deeper. My intellectual / rational side, so often a steadying counterpoint to more turbulent emotions, turned against me. Somehow, I awakened a hornet's nest of meta thoughts which typically seem safely ensconced behind an undefinable partition — call it the "Reality Prevention Shield" — where the "ping, ping, ping" of their tapping on the glass is muted and inconsequential.

You think you're living a meaningful life? What is meaning anyway? We're all just dust in the end, so who cares if what you do echoes for a few generations or a few hundred? Look at all us ants, scurrying around to complete our tasks, fulfill our purposes, and die.

It got worse.

If we're all just dust anyway, what is the purpose of a human relationship? What is the purpose of purpose? If all of the emotions of love and pain and joy and suffering that we experience across our lives end up as just dust, then do they have meaning? Why should my life care at all for these other ants on our meaningless quest to shuffle around grains of sand? Why is their joy or suffering anything of mine to take on? Hell, why shouldn't I just throw the match on this life and live hedonistically and materialistically to my heart's content?

Snip, the mooring lines were gone and I was officially adrift.

Rally

Fuck this, I can out-think this thing. I hit the books.

The one thing which seemed so central, in the most cliché fashion possible, was the idea of meaning. I could only motivate myself to move forward if it felt like each step had meaning. Was my business meaningful? Were my relationships meaningful? Was each breath I took meaningful? So I resolved to understand meaning, to fight against this intellectual and emotional drift.

Despite frequently being an armchair philosopher, I had never engaged in a formal study of philosophy. I needed it now. So I read up on meaningness and learned that I was stuck in a Nihilistic loop. Nihilism and Eternalism (typically Faith) are frequently found in opposition to each other. One who is caught between them will often explore materialism and a number of other paths that my ideological wanderings had taken me through. Familiar ground…

But despite putting names to some of the thoughts I was having, I couldn't shake the sense of drift and the seas were rising. My relationship ended. I fantasized about hitting the eject button on the business and traveling alone but couldn't even get excited about that because it felt like a waste of time… which was meaningless anyway… dang it.

In these crises, the warm blanket is so often the idea of "faith". But faith is a very rocky intellectual ground and I'm violently allergic to the idea of organized Religion and identify as mostly atheist. So, desperate to dull the edge of this existential knife, I resolved to look inward and discover my own sense of faith and meaning.

I listened to my physical being and quickly identified three things it wanted:

1. The heart wants to love and be loved.
2. The body wants to be healthy and active.
3. The head wants to be challenged to learn and grow.

I imagined lives that I could live perfectly in the service of these three things, carefully plotted realities that would optimize for love, health and challenge. And yet, I found them wanting. I couldn't deny that there was a fourth piece missing, and I had to admit:

1. The soul wants to live meaningfully.

All the basic needs can be met but life will feel incomplete without serving the soul (whatever that is). The search for meaning had circled back on meaning. Not helpful. Intellectual investigation and logic had not solved this problem.

Resolution?

Then, somehow, I turned the corner. I wish I could tell you exactly what it was that did the trick — and there are some good culprits — but I really don't know. Perhaps not quite so stark as the piece of corn, but my own version.

A few weeks ago, woke up and sat on my bed to write but nothing really came out. The tank was empty and motivation was low. I didn't want to work and I didn't want to think. I felt like a lump on a log.

So I wrote three words:

"I am depressed."

You see, despite all the existential angst and emotional dulling, I'd been the frog in the slowly boiling water. I'd thrashed and twisted on every level I knew in order to avoid having to face the simple truth that I, a bringer of light and optimism and energy to the world, was, for the first time in my life, actually depressed.

The words bounced around my head a bit and I tried them on. Despite their unfamiliarity, they fit like a glove. It was like trying on a new identity and finally realizing that, by doing so, you could trade your prismatic glasses for a clear perspective. It felt like Truth, so I accepted it and grabbed some food.

A few hours later, I went for a walk. As I've frequently done, I thought about the business. I went through all the potential positive and negative paths forward from our present position. But, unlike the previous times where I had intellectually imagined some of the downside cases where I had to shutter the doors and walk away, this time I went all the way in.

An entrepreneur's identity is their business. It's extremely hard to separate the two. The idea of being apart from your business is strangely terrifying and bleak. We all know that we're super humans on one hand, capable of mobilizing other humans to birth something from nothing, and that we're also strangely unemployable on the other, possessing a melange of skills that just doesn't fit well into anyone's idea of a role player. We tie our personal brands and our identities to our businesses and the idea of introducing ourselves and not saying "founder" feels strangely hollow.

During that walk, I didn't just imagine what it would look like to have to let it all go, I felt it. I put myself into my own shoes, many months down the road, and truly accepted the reality that meant. Accepted what it would mean for my identity to walk away.

After trying on the identity of depression, I tried taking off the identity the founder. It didn't feel quite right, but it felt… okay.

That night, a third thing happened. I reached out to and grabbed a long beer with a friend who runs a funded startup with a couple dozen employees. For the first time, I talked frankly and deeply about the things I'd thought and discovered. About existential crises, Founder Depression, and the plagues of many tough options when running a business.

As is his way, he listened deeply and then related on just about every level. How he discovered that, despite being even more of an energetic and positive human than I am, he began suffering pretty hard from burnout and even depression around the business. How he now had to schedule a full month-long sabbatical each year during the time when the key numbers seasonally fell to avoid being pulled down into the quicksand.

He also framed a totally sensible, logical question which has stuck with me ever since:

"Tying your identity to a startup is basically the worst thing you can do. If you measured your success as a person, you would be 100% successful because you're totally crushing it as a great human. But your startup is at least 90% likely to fail according to all real odds I've seen, so you're willingly giving yourself a 90% chance of failing at life. Why would any sensible human do that?"

Huh.

The next morning, something was different. I woke up at 5am and started cranking. I lined up the day and knocked it down, putting in more productivity than I'd had for the past two weeks combined. I felt clearer and steadier than I had in a very long time.

Most importantly, that glass Reality Prevention Shield which seemed to magically prevent existential angst and allowed me to focus on being present, emotional and human had quietly slid back into place. The angry bees of logic were hidden away and quieted and I found that I could re-engage with many of the things that I knew made me happy. My memory started improving and my energy levels began to rise again.

The road is long and I can't say that I'm back to full power but the trend has definitely changed for the better.

(over)Analysis

So what the heck happened?

I wish I knew, truly. Somehow, when I was finally ready to admit that I was depressed, that I was ready to fully let go of the most important construct in my life, and that I could talk about these two things openly… catharsis happened and a measure of healing could begin.

If this was a fairy tale, we'd have a pure and happy ending. That is a different story.

In this case, there are certainly good things. I feel more motivated than I have in a long time. I feel like I can focus on the business with far less distraction and that my relationships and time are more valuable than before.

You may think, based on my acceptance of the path, this is where I go and shut down the business to live some sort of "enlightened" life of freedom but that's not true either. Just accepting what the "bad" path would be like, how it would go down, and what my identity would be if it did was enough to set some sort of floor on things. It is like an ejection handle that I can finally see and put my hands on. That doesn't mean I need to pull it, but having the security of doing so makes me feel less trapped in a particular path and more energized as an entrepreneur.

I feel the same way when I've exhaustedly finished the required distance during a training swim and could go home but, just by having the option to finish, I discover an extra reserve that's good for another turn around the bay.

But the one thing that is missing here is resolution. Truth.

As an intellectual person, I find it downright alarming that my psychology and mental health can get flogged by the full fury of the existential storms that lurk in the darkness beyond placating normalcy and then have everything fixed in some magic moment of seemingly unrelated catharsis. That there is some "Reality Prevention Shield" which, like Earth's atmosphere, normally shields my psyche from the radiation of reality but which can disintegrate at a moment's notice because the fundamental truths that test it haven't actually been resolved.

I still haven't solved my crisis of meaning. I still haven't reached an intellectual resolution which allows me to feel confident that this is a true peace and not just a temporary detente. I can say that I again feel a sense of awe and wonder at the reality of existence but am deeply suspicious that everything is magically better just because I've been able to hide safely from the cruel truths of the world.

Frankly, it feels like that portion of my mind just got tired of spinning on overdrive and is taking a break. Regrouping its strength?

So, if you've found yourself on this road before, maybe you can find some measure of solace in the play of my story, if not the intellectual cure-all you might have hoped. If I had to turn things around and offer advice, I'd say to be fully honest with yourself and open to talking it out with someone you trust. Words like "drift", "meaningless" and "self disappointment" are ones beyond the usual batch which you should look out for.

For my part, I'm regrouping to meet the next charge by arming myself as best I can. I'm studying the works of ancient philosophers to give context to my search for meaning. I'm working to build a regular meditation to stay grounded in feeling and always in possession of the awe of life. I'm doing a careful survey of my own values so I can seek paths that best follow their direction. And I'm trying to be far more careful of my inner voice and how that judgment affects the fundamental human desire to love and be loved.

When all else falls, there is at least some final solace in René Descartes' "I think, therefore I am".

If this thing comes back, I'm not going down without a fight.

—

Special thanks to Brad Feld and all the other members of the community who have openly shared thoughts about their own struggles over the years. It makes it infinitely easier to tackle something like this when there is such an accessible base of knowledge and precedent.