The Pain Button

We forget all too soon the things we thought we could never forget

Illustration by Antra

Eating Glass

After my second year at Claremont McKenna College, I took a leave of absence to hitchhike. I thumbed my way through Argentina, Bolivia, Uruguay, Chile, where I dumpster-dived and slept in caves, in unlocked lifeguard towers, on sidewalks, and park benches. I had become wary of comfort, and I contrived hardship. When I returned to school, I eschewed the dorms. Opting instead to sleep and study diagonally in my Honda Element, upon a low density foam folding mat which left me no more than eight inches of headroom. It was an oversized coffin with no lavatory. At night, I pissed into a Nalgene bottle.

Soon after graduating from college, I heard that the secret to success was doing the hardest thing you’ll do all day, while everyone else was still sleeping—that made perfect sense to me, so for over a year I consistently woke up at 4:45AM to do 300 burpees on the sands of Venice Beach before sunrise. 

Something about pain always sat well with me.

I once ran a marathon on eight hours' notice without a single day of training, and believe me, that had some painful and lasting consequences. It seemed to me that pain was part of the reward. In this case, patellofemoral pain, a dull-aching daily reminder that I could do hard things. For the longest time, I wondered what my upper limit was. I searched steadily for it.

When I started my first serious company, Alltrue, pain wasn’t on my mind. Alltrue curated, produced, and sold socially- and environmentally-conscious products—an entirely wholesome and pain-free business premise. Pain was for feats of endurance, and adventure. 

As it turns out, there would be pain. This time more psychic than physical. But when it arrived, I welcomed it as I always had. Pain threshold became a measuring stick for entrepreneurial aptitude. Like so many other experienced founders, I nodded enthusiastically as I watched Elon Musk give an interview, where he related the now famous mantra: “Starting a company is like eating glass and staring into the abyss.” And even more furiously as he continued: “You have to have a fairly high pain threshold. You’re constantly going to be facing the extermination of the company…[and] the most painful and pernicious problems... And that goes on for a long time.”

As that went on, I didn’t sleep much and I didn’t eat well, for many years. For many years, there were many days when I didn’t sleep or eat at all. And when the business really started growing, there were growing pains. 

At least once per quarter there were work-through-the-weekend, all-hands-on-deck affairs. Numerous all-nighters, when customer support tickets outnumbered customer support agents 100 to 1. There were times when litigation threats appeared in my inbox multiple times in a week. And when that same inbox was overwhelmed by boilerplate rejection emails from the investors we desperately needed. There were times (plural) when the monsoons of Rajasthan mold-rotted our products as they sailed in their shipping containers across the Indian Ocean, without much-needed desiccants. There was the time when thirty-thousand handbags were detained in customs-clearance-office-hell because of a byzantine country-of-origin labeling error. The time when we shipped ten-thousand room fragrances with defective nozzles, and the time when we had to recall seventy-thousand tea kettles at a cost of roughly eight hundred thousand dollars after CPSC attorneys fees, because the lids were missing a ⅛” steam vent.

Eventually it became clear that pain was part of the job. In fact, pain was the job. The job was: the constant dilemma of choosing which kind of glass to eat, while bearing the burden of responsibility for outcomes that affected hundreds of thousands of people: customers, employees, manufacturers, investors, et. al. Over time, the psychic pain compounded and morphed into a dread-y, low-grade perma-stress. It wasn’t all bad, of course. Oftentimes it was rewarding and hugely fulfilling. And in any case, I still courted discomfort in my free time, so a free dose of daily-work-pain was welcomed as a challenge.

Gnarly as it was, it was a good career fit: a game for people with great endurance in the face of repeated trials and constant pain. I could do pain. And as I continued to weather wildly painful periods as an entrepreneur, I kept coming back for more. It hadn’t killed me yet, and the company, ostensibly, grew stronger. I couldn’t find my threshold. So I kept knocking on the door. Finally, there was an answer.

Vomiting Glass

Imagine, you’ve been building a company for seven years—eating glass and staring into the abyss, for seven long years. 

And then finally and suddenly, way back in the furthest reaches of the blackness you see a light. You’ve sacrificed sleep and health and wealth and wellness and weekends and happy hours for seven years, all for the remote possibility of this: your company is going to be acquired. For nine figures. $100M, at least. The light. Freedom, financial and otherwise, forever, in the form of an inbound inquiry from an interested buyer. You hire an investment bank and drum up additional interest. The courtship continues. The buyer becomes more keen. You enter into exclusivity. 

Meanwhile, as you navigate the high stakes tango of M&A diligence, the perfect storm intensifies in the background. Then, all at once, it forms a tidal wave. A pandemic is at fever pitch. The global supply chain enters a crisis; the cost of freight shipping decuples.^¹ Your marketing blueprint collapses, growth plateaus, then it declines.² The capital markets freeze. Your lending partner pulls a vital line of credit. So does your shipping carrier. You’re running out of cash, quickly now. Now, your subscription rebilling date is out of reach. Your lifelines scuttle. Your situation is dire. Your lawyer tells you that you should talk to other lawyers who specialize in dire situations and those other lawyers tell you something very much to the effect of: “You are now in the ‘zone of insolvency’ and you have a fiduciary duty to put the business into bankruptcy. Immediately. M&A? Off the table. Prepare to lay off the entire team by the end of the week. Oh, they’re like family to you? Actually, you’ll need to let them go by day after tomorrow, over Zoom. One by one. And forget being set for life—this will bankrupt you. Yes, the business, but also you. Personally. Here’s the number of an attorney I recommend for that kind of thing, you’ll need it. Oh, and one last thing: don’t Google yourself for a while.”

That happened to me. I know what that’s like.

It’s like being swallowed by the abyss. Total blackness and morbidity. I contemplated suicide for the first and only time. It was the only way I could be sure to stop the despair. Creditor debt loomed large in my mind, but it paled in comparison to the feeling that slowly settled into my body and bones. Like a sponge soaking up cortisol. Every inbound message and official mail absorbed into the anguish: employees asking about severance, vendors asking about bills, state authorities asking about taxes, hundreds of thousands of customers asking about orders, credit card issuers pointing out personal guarantees, press outlets asking for comments. 

Investments in me, made by family and friends: worthless. 
Employee equity: zero. 
My net-worth: sub-zero.

Over the years we saved our company from the brink of death several times. But that was chewing glass compared to this. Every day of the tailspin made the day before it seem like a cake walk. Distress pulsed through my body mercilessly, while I buried my business in mirthless Zoom meetings with attorneys and liquidation trustees.

Bankrupting a company is like vomiting glass and being swallowed by the abyss.

So, what’s next? 

When the pain gets to be that bad, it etches itself into your psyche—a permanent reminder of where you’ve been, what you’ve done, who you are. It’s the psychic equivalent of the nagging knee pain that haunts an under-trained marathoner for years and years after the race. You don’t forget. You can’t.

Even still, I made a special effort to ensure redundancy. I wrote a 40-something page post-mortem which codified my experiences into principles. Things that were systematically wrong with the business, mistakes I made, things I did right. Mostly it was a remembrance, full of painful lessons that you couldn’t pay me to learn again.

But the world spins madly on, and before the dust had even settled people began to ask: So, what are you going to do next? In the world of business and small talk, you don’t win awards for licking your wounds.

It sure felt a lot better to say: I employ over a thousand people and run a business that grosses about a hundred million a year, than it did to say: I’m not working and I’m not sure when I will again or if I can again or what I’ll do. But that’s all I could muster. And as I mustered different variations of I don’t know, it became increasingly difficult to get the words out. I’d never considered the egoic impact of unemployment, of feeling low-status—of not working on something that impressed people, of not working at all. A deep inner urgency set in. 

And so, as people continued to ask about my next move I’d rattle off three or four ideas I was vaguely considering. Eventually, I homed in on the one that people nodded most agreeably to. I’d start the next great outdoor company, the next-generation-Patagonia. Publicly, it felt good to start solidifying something. Privately I had serious concerns about the viability and volatility of an apparel and gear business. It violated so many of the principles in the post-mortem I’d made for this very purpose.³

To stop second guessing, I set up dozens of meetings with technical product designers, creative directors, and industry consultants. I deeply researched the outdoor space and most of its niches. I crafted a plan. I picked a brand name. I set a start date. And as the start date approached, I came across an illuminating study, which forced me to reflect on my neverending quest for pain.

The Pain Button

First, participants in the study were given a painful electric shock, then they were asked whether they’d pay to avoid being shocked again. Anyone who’d pay to avoid another shock was invited back. In the second stage of the study, participants were put in an empty room, alone, with no stimuli for fifteen minutes—no books, pens, paper, smartphones, nothing except a button that would administer the same painful electric shock as before. Before the fifteen minutes were up, 67% of the men pressed the pain button and shocked themselves.⁴ Astonishingly, they preferred pain to free-range thought, boredom, the unknown.

It was an all too obvious metaphor for my life. Here I was, palm hovering over the button. Ready for some pain. Vomiting glass? Better than nothing. I’d found the threshold, my upper limit. It turns out that it never had anything to do with pain at all. The threshold was and is the unknown. 

The masochism that prevailed in endless pursuit of activity, of feeling, of pain, was so much easier than the nebulous alternative: the unknown. Pain, it was so much easier to pursue pain, than to quietly peer into my own mind and ask the simplest questions: What is the feeling you’re really after? What do you really want? And then, to patiently wait for an answer.

The problem is, there is no answer. At least not right away. The world of the unknown is shapeless and unsettling. Questions like these create a vacuum, an invitation for our deepest insecurities and anxieties. A thousand unknowns rush in to fill the void.

It’s been two long years since April 12, 2022. Since I assigned my business to Armanino, LLP for the benefit of creditors. It’s been one year since I began asking myself, What do I really want? I’ve since been married, I’ve biked 3,500 miles across a continent, and I’ve moved to a new state, and still there are more questions than answers. My mind drifts to the unknown…

…I want to figure out what I really want before I run out of money. I want to figure out what happiness is. What enough feels like. Whether that’s a feeling I’m capable of feeling. I want to figure out whether I want kids, and why, and if so how many, and how I’ll afford to take care of them if I haven’t figured out what I want. I want to figure out why it bothers me when I imagine what other people will think about the fact that I’m writing essays instead of finding a job, or starting the-next-Patagonia. I want to figure out why I often find myself aspiring to make a dent in the universe. And why I so often find myself wishing I didn’t think about dents at all. I want to figure out why I want what I want, so that I can figure out if I really want it… 

Every question is Medusan: doubling, then redoubling again and again, into an ever-expanding chaos of unanswered and potentially unanswerable unknowns. 

The unknown is a struggle. Much more of a struggle than pain. Pain is easy. It’s something to do, it’s real, and maybe even knowable. Better the devil you know. Just press the button. It’s no wonder so many of us choose pain. And maybe we ought to sometimes—maybe we have to. Maybe some non-trivial amount of pain is requisite to a rich and meaningful life. But the deeper you explore the purgatory of existential personal inquiry—the unknown—the better your chances of discovering the things that are worth suffering for. A family, a relationship, a business idea. Not all pain is created equal. Some pain should be avoided. Sometimes it’s too much. And sometimes, unless you’ve done the work, you won’t know whether you’ve pressed the edifying pain button, or the traumatic, psyche-etching, with-you-forever pain button. Take it from me.

When it’s more comfortable to shock yourself than it is to simply stop and ask yourself why you’re about to shock yourself, that’s a clear sign that you don’t have the answers to some very important questions. When pain is easier than self-inquiry—when it looks like an easy, knowable, pressable button—before you press it, try asking: What is the feeling I’m really after? What do I really want?

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Thank you for reading this essay. I’ve decided to share my writing because people like Paul Graham (and so many others) have done a lot for me by sharing their writing online. I plan to cover a lot of things over a long period of time—some of the next few things I expect to write about include a deep exploration of the attention/concentration epidemic, the power law of friendship, and the magic of unrealistic goals.

If you think these ideas might resonate with someone in particular, I’d appreciate you forwarding them along!

Thanks to

Michael Dean

,

Tyler Donahue

,

Chris DeMarco

, and Antra Svarcs Richardson for feedback on this essay.

1. Before the global pandemic it cost roughly $2,000 to transport a shipping container from Asia to Long Beach, CA where we received it. At the height of the pandemic, that number was closer to $25,000 per container. And even at that price, it was nearly impossible to reliably book cargo, because large corporations like Walmart regularly swooped in and outbid businesses like ours. We shipped several dozen containers each season, which amounted to millions of dollars in unexpected costs, and we could not pass those costs on to our customers because our business was subscription based, and they had paid us up to a year before the supply chain crisis.

2. As anyone who was involved in ecommerce in the early-2020’s knows, the iOS 14.5 software update by Apple created an existential issue for online marketers. Simplistically, the update essentially broke Facebook’s advertising platform (as well as all other programmatic marketing channels—Pinterest, Snapchat, TikTok), because it stopped allowing Facebook to track user activity after they left the Facebook App. Ad personalization became a privacy violation. As people updated their iPhones, it increased our customer acquisition costs by 250%, and we spent dozens of millions on Facebook advertising. The update also caused Facebook’s market cap to crater by $200B after their next earnings report—the largest single day decline in the history of the public markets, if I recall correctly. It also, in my opinion, caused Facebook to change its name (to Meta) and pivot its entire idea of itself. Without going too deeply into it: this iOS update was a very big problem for us, because it made it impossible to grow into forecasted inventory purchases that were made nine months earlier—and, coupled with the customer service nightmares caused by the supply chain crisis, which led to above-average churn—we started shrinking. Shrinking is manageable if you anticipate it, it’s not okay if you anticipate significant growth, and don’t have huge cash reserves to weather the storm.

3. General commodification dynamics: Low barrier to entry, moderate differentiation, strong competition; little technological differentiation/leverage, high brand leverage. Expensive physical inventory—subject to fads and seasonality. Generally, lots of products that are probably already better than they need to be, competing for not a lot of dollars.

4. 25% of women shocked themselves. Which I found interesting. Still high, but so much lower. I’m a guy, and I was about to smash the button, so the study resonated with me more than it might resonate with some women—who are apparently more patient and less masochistic.