On the final Sunday night in February, Bitcoin broke $65,000, and I shrugged. There wasn’t a hint of second-guessing or even the thought of panic selling.
At the beginning of February, I decided to go all in on a simple habit. I’m buying Bitcoin every single day for the rest of 2026.
This pullback looks like the perfect time to do it. But I’m not trying to time a bottom. I’ve built a routine that removes that question entirely.
By dollar-cost averaging with automated buys, I remove the guesswork. If the price drops, I buy. If it rises, I buy.
And if Bitcoin eventually returns to its previous high around $126,000, every dollar I’m converting today will nearly double in purchasing power.
That makes daily accumulation at these levels feel obvious.
Over the past year, I’ve been studying money in ways I never have before. I recently finished “The Bitcoin Standard,” which followed “Broken Money” and “The Hidden Cost of Money.” Together, they’ve reshaped how I understand scarcity, trust and the very concept of money itself.
I’ve supplemented that with documentaries — “The Hidden Secrets of Money,” “God Bless Bitcoin” and “Money Masters.”
Each one added layers to my understanding and connected dots on how history, policy and technology collide to create — and destroy — value.
The more I learned, the clearer it became: digital money isn’t a gamble. It’s the next logical step.
That growing belief pushed me to take another step: self-custody.
On Feb. 13, I bought a cold wallet to move my Bitcoin into my own control.
For me, that was a line in the sand. A popular catchphrase in the Bitcoin community is “Not your keys, not your coins.” Holding my own keys means stepping away from intermediaries and embracing personal responsibility.
It’s not just about potential upside anymore; it’s about sovereignty. About protecting what I build. About safeguarding my wealth without relying on anyone else.
And yes, I’m in the red. By a lot.
I built my position near the top in 2025, when conviction hit me hardest — not after a crash, but during the euphoria. I’m OK with that.
At one point recently, my position was down more than 40 percent. I’d be lying if I said that doesn’t register. It does. But it hasn’t changed my behavior. If anything, it’s clarified it.
I didn’t commit to this strategy because I thought the line would go straight up. I committed because I believe in where this is heading over years, not weeks. And because I know what happens to fiat currency throughout history. The long-term thesis remains intact. A drawdown doesn’t invalidate that.
Practical changes also helped cement my daily purchase habit.
In early February, Cash App rolled out updates that made buying Bitcoin cheaper and simpler: no fees on purchases of $2,000 or more, and no fees on recurring buys.
I’d been paying another platform $29.99 a month since last July just to avoid fees. Of course, I’ve canceled.
I don’t know what will happen next.
Bitcoin could dip further. Or it could take off.
Either way, when I look back on 2026, I won’t have regrets. All indications are that I’ll be glad I leaned in.
Darnell Mayberry is a sports editor based in Chicago and is the author of “100 Things Thunder Fans Should Know & Do Before They Die.” He loves his daughter Parker, money and the Minnesota Vikings. You will find his column, Money Talks, each Saturday on cleveland.com and Sundays in The Plain Dealer.