The Greed That Never Ends

What I Learned About the Mind That Never Has Enough

Early morning. My phone vibrates with an unexpected notification. I roll over in bed, squinting at the screen. Oh shit. A major sell-off was underway.

Bitcoin had been bleeding for months, down from its high of $64,000. As the morning unfolded, price alerts triggered again and again. I was hunched on the couch, compulsively refreshing Coinbase, then flipping to Twitter for commentary, back to Coinbase, then Twitter again.

My heart rate spiked. Thoughts poured in: I should have sold months ago. Steve, you greedy prick. Is it going to $10K? Jesus. Years of gains wiped out. I couldn’t feel my body anymore, just the rush of thought.

Everything else faded—the room, the light, my wife with her coffee, my daughter playing with Legos a few feet away. There was only one number on the screen, falling like a stone: $22,000. $21,000. $20,000.

I told myself this dip was temporary, that I was in it for the long haul, that I’d held through crashes before. I was a believer. I’d bought in 2011 and promised I’d never sell, that I’d leave it to my kids someday.

But the number kept falling. There seemed to be no floor.

—

Later that morning at the playground, my wife and I sat on a bench while our daughter yelled “da-da” from the monkey bars. I missed the whole thing. I was there physically but not mentally. I was spiraling on my phone and lost somewhere else on planet Steve. Coinbase is open. My thumb hovers over the sell button like I'm defusing a bomb.

My wife had suggested the sensible path: "Sell half. Recover our cost basis. Take some profit. Ride the rest." But panic doesn't do sensible. Everything I'd read about Bitcoin being an inflation hedge was crumbling as tech stocks crashed and took crypto with them. Ten years of holding was cracking. This time was different, I told myself.

My daughter giggled, climbing higher on the jungle gym. I was consumed by numbers and what-ifs.

I have to sell. This bloodbath could get worse. I just want out. Get me out.

I just couldn't hold the tension anymore. I folded. I hit sell.

I took a deep breath. Relief flooded me as if a long battle had finally come to an end.

Then came the sinking feeling: What have I done? Oh shit.

After a decade of holding, after swearing I’d never sell, I buckled under pressure and I broke.

—

For two years, I carried that decision like an anchor around my neck. The guilt and shame would hit me in waves. It wasn't a crushing blow that would sideline me for days, but more like a buzz that would capture my thoughts while I'm making coffee or picking up my kids from school. I'd start calculating: If I'd held, that would be worth a small fortune now. Jesus. The house we can't build. The cars we can’t purchase. The early retirement. The financial security to become a fulltime writer. Twenty or thirty minutes would disappear as I stared at my phone, doing the math over and over, knowing I fucked up.

I did everything to cut it loose—journaling, meditation, therapy sessions where I'd talk in circles about "letting go" and rationalizing the decision. I tried to find acceptance, to move on. Sometimes I thought I had.

Then my twin brother would text me out of the blue asking if I saw the latest price, definitely mocking my decision. Or I'd be lying in bed next to my wife, half-asleep, and suddenly I'm designing our dream house in my head and thinking about the capital that could have made it possible. I wasn't my best self those mornings, distracted with the girls at breakfast, irritable over what could have been.

I just fundamentally felt like I failed at something I'd been so sure about for over a decade. All that conviction, all those years of holding through crashes, and I'd bailed at the bottom. That was hard to carry until something shifted last month.

—

One afternoon, while on sabbatical in Portugal, I was mindlessly scrolling Instagram vids as my little one napped in the next room. All of a sudden, the algorithm fed me a post from Morning Brew: Bitcoin had hit an all-time high, north of $110,000.

What had disappeared for months came flooding back. The math was immediate and brutal. My stake would have been worth millions of dollars. All those zeros I'd never see or spend.

I could feel it all—the greed, the regret, the shame—and somehow it was all here again. That familiar tightness in my chest, the mental movies of what could have been, the weight settling back onto my shoulders like an old coat I couldn't take off.

—

Later that day, walking to meet my family at the pool, something suddenly shifted.

I was observing the old thoughts, feeling the suffering, really feeling it, when this thought emerged: Wait. I suffered when I had it too.

And suddenly I could see it clearly. When I owned Bitcoin, it was never enough. I always wished I'd bought more when I first discovered it. When it surpassed $60,000, I kicked myself repeatedly for not buying more at various price points.

And during the big runups when mania would set into Twitter, I always wanted the price to go higher. I was constantly checking the charts, constantly calculating what it could be worth, forecasting future price movements, constantly living in some future where I'd finally have "enough."

The realization hit me like my toddler slapping me in the face: I was creating suffering on both ends. When I had it, it wasn't enough. When I sold it for a gain, it wasn't enough.

The anchor that had been dragging me down for two years suddenly fell to the ground. I could feel it viscerally… the crushing weight just… gone. The shame that had been pressing on my chest, randomly following me through coffee shops and school pickups and irritable mornings, simply evaporated. I was liberated.

—

Here’s the reality: I made a decision. It didn’t work out the way I expected, the way I wanted.

What hit me that afternoon in Portugal was something we all know but rarely admit: I just didn’t want to suffer over this anymore. I didn’t want to continue to fuel the part of my mind that will never be satisfied, no matter what I get. There is no winning with "not enough."

Surrounded by olive trees with the sun beating down on me, I could finally see the abundance flowing in my life—my family, my health, our home, my coaching practice, the freedom to take sabbaticals and write, the simple fact that I was walking to meet my kids at a pool in the countryside. I'd been so busy calculating what I didn't have that I'd missed what was right there.

We all regret decisions we've made—bad investments, paths not taken, opportunities passed on, things that could have easily changed our fortune and security. We all imagine what could have been. Whether we have $10 million, $1 million, $100 thousand, or $100 the bank, we all have our own versions of this dynamic. The numbers change, but the mental torture remains the same.

But when we live in the past, identifying with these decisions years later, getting trapped in guilt, blame, anger and sadness, we suffer. We grasp at what could have been versus what simply is.

Through my coaching practice and countless conversations with friends, I see how universal this is. We all do this. It's natural. There's nothing wrong with wanting a better life or having nice things. But when we get stuck playing Monday morning quarterback, feeling fundamentally broken because we don't have certain things, we miss what's actually here.

Here's what I know: as soon as I get what I desire, there’s always another thing, and another. It's endless, especially in our culture where what we have communicates who we are. But there's a different way.

It comes down to acceptance of what transpired. Compassion for myself, for the choices I made. A gentle letting go, a softening, the way your body relaxes when you finally trust something or someone. I go within to find out where I am. Can I accept myself for the decision? Can I accept the thoughts and feelings that are here? Is there still constriction, resistance? Can I see the suffering it's causing? Can I choose not to make it a big fucking deal that haunts me for the rest of my life?

The truth is, I can. And from that place, gratitude flows naturally. Not as something I have to practice, but as what remains when I look around and stop fighting what is.

When the “never enough” voice starts up now—and it still does—I recognize it faster and see it for what it is. I just don't take it as seriously anymore…and with that I’m learning to be free.