In the Spring of 2021, I embarked into the crypto world, leaving behind a 12-year career on Wall Street to join a rapidly-growing startup in the digital asset infrastructure space. My personal journey had begun a few weeks earlier with some cheeky NFT buys, but soon, I found myself deeply onchain, with a significant portion of my net worth invested in it and my professional future staked on it. The bull market was awesome, albeit too short, but we did well and we’ll leave that for another piece.

Fast forward to the end of 2021 and I felt adequately prepared for the end of the traditional four-year cycle that crypto tends to exhibit. I sold my spot bags and went into the new year with a barbell portfolio, heavy on stablecoins and JPEGs. Ready for whatever the market wanted to throw at me, or so I thought.

The true test began as the industry took a series of massive hits in the Spring of 2022, marked by events such as the collapse of Luna and 3AC. Despite these, my confidence remained unshaken, bolstered by strategic decisions that seemed to pay off. However, the landscape shifted dramatically post the FTX bankruptcy in November, ushering in a harsh crypto winter and an even worse NFT extinction-level event. This period marked the beginning of a profound introspective journey.

My personal transition from confidence to doubt was gradual yet piercing. The realization that I had left behind a stable and lucrative Wall Street career for what felt like a digital wildcatting venture in an unstable industry was daunting. The weight of possibly witnessing an industry's downfall and its implications on my career choice dawned on me. This period brought forth significant emotional challenges, particularly in maintaining motivation. Transitioning from the high-energy environment of a trading floor to the cold, quiet lulls of a bear market was jarring. My response, initially, was an increased reliance on spending time online, mostly on Twitter, seeking some form of engagement or validation, perhaps a subconscious quest for dopamine in a landscape growing increasingly desolate.

However, the most profound challenge was the immense self-doubt that crept in. The last 12 months were a relentless interrogation of my choices and existence. I found myself plagued by an unshakable sense of uncertainty, questioning not just my career switch but my very being.

“What the fuck did I do?”
“Why didn’t I sell the NFTs?”
“How will I turn things around?”

I found myself constantly questioning everything. It wasn’t even about the money at that point anymore. It was about me, staring back at the bear, shaking as it looked me in the eyes and stripped me down to my soul.

Back during my Wall Street days I used to manage billions of dollars of trades on a weekly basis, with most of the action occurring in bursts of 20-30 seconds. There were plenty of times that my hands got sweaty then, but that never lasted long. You either won or lost the trade, the risk was managed over the next hour, and you moved on.

This time it was different.

The same ice water that used to flow through my veins and kept me cool on the floor was now making me shake with anxiety. Sleepless nights that drew on forever, feeling left out in the cold with no end in sight. Finding strength through conviction, which even if I believed it would all work out, the mere thought that I could’ve traded much better would get the stomach churning again. Imagine regretting one of the best decisions of your life.

The once thrilling chaos of the trading floor, with its predictable adrenaline and routine, suddenly seemed like a lost haven. I longed for its consistency, a stark contrast to the volatile unpredictability of the crypto world. This longing was more than nostalgia; it was a yearning for a time when my choices seemed less fraught, my path more assured. Reflecting on the industry's nature, I recognized the cyclical patterns often overlooked by many. The crypto world, like any other, is prone to cycles of boom and bust, yet there's a tendency to attribute success to skill over circumstance. This introspection led to a realization of the role luck plays in success, a humbling understanding that I, too, might have been a beneficiary of being at the right place at the right time. This caused me to miss the first few signs of the market turning as coins started slowly moving off their lows through mid 2023.

Bear market PTSD. All the doubt. You know better and you know that you know better. It’s the fear of regret that gets you. Even if you manage to overcome it, you get the size wrong.

This journey through the crypto bear market was more than a financial expedition; it was a profound emotional and mental odyssey. It taught me resilience, the importance of adaptable coping strategies, and offered a nuanced understanding of an industry often shrouded in hype and speculation. As I continue in this ever-evolving space, these lessons remain pivotal, guiding my decisions and outlook towards a future that is as uncertain as it is exciting.

I have so much respect for those who have been through a full crypto cycle, whether that is by choice or by force. I can’t wait to see everyone get another chance at changing their lives next year, armed with the lessons from our previous cycles. Good luck, godspeed and don’t forget to seize the Meebs.