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Back to Basics: Trading Lessons from Costly Losses and Practical Goals

December 9, 2025 Technology

I was sipping my cup of cacao this morning, digging through old trade logs, and I felt that familiar gut punch looking at some numbers I’d rather forget. Lately, I’ve been zeroed in on returning to my core—trading—after spreading myself too thin with TrueSight DAO and projects like Agroverse. But this isn’t just about cutting back; it’s about facing the brutal lessons from past mistakes and keeping my goals real. I’m not after fantasy wins—just enough to cover my yearly expenses and a bit extra. Let me walk you through some painful losses, how they’ve reshaped my approach, and the anxiety of sitting on the sidelines when the market just isn’t right.

Hard-Earned Lesson #1: The $100,000 Putin Oil Debacle

Back in 2020, I made a speculative bet on oil prices that still stings. I had a long position, banking on Putin cutting production so prices would rebound. Instead, he kept dumping oil on the market, and my position cratered. The damage? A $100,000 drawdown. That’s right—one hundred grand, gone. It was a harsh wake-up call that speculating on geopolitical moves, especially with unpredictable players like Putin, is a game I can’t win. I’m not a mind reader, and I’m done pretending I can outsmart those kinds of wildcards. Now, I wait for the chaos to peak and the market to bottom out before I even consider a move.

Hard-Earned Lesson #2: The $130,000 MLP Wipeout in 2015

And here’s the kicker—I’d made a similar mistake before. Way back in 2015, I took a $130,000 drawdown, but this time it wasn’t straight oil positions. I was buying into Master Limited Partnerships (MLPs) in the energy sector, lured by juicy yields of 13%. Seemed like a no-brainer. Except it wasn’t. The market dynamics and external shocks wiped those positions out completely. Another massive loss, another reminder that oil-related bets, especially when tied to factors I can’t control, are a trap for me. I walked away with nothing but a lesson I can’t ignore.

Hard-Earned Lesson #3: Wildcards and Unbalanced Risks

Then there’s the chaos of political wildcards like Trump. His tariffs around May 2025 crushed my positions while I was already squeezed by a liquidity crunch for Agroverse’s cacao purchase. Here’s the thing: it doesn’t make sense for anyone to underwrite that kind of risk in a community project. And if it doesn’t make sense for others, why should it make sense for me? I’m not in the business of carrying unbalanced loads. Lesson learned. I’ll contribute to TrueSight DAO or Agroverse just enough to keep things rolling, but my core stays protected. Surplus only. No exceptions.

Key Observation: Realistic Returns and Smarter Plays

Let’s get one thing straight—I’m not chasing impossible returns. My goal is grounded: generate enough through trading to cover my yearly expenses and have a little extra on top. That’s it. But after losses like $100,000 and $130,000, I’m also crystal clear on where I shouldn’t play. Oil, banks, and political situations where a few small players can cause outsized turbulence? Nope. Too unpredictable, too stochastic. I’ve got no control there, and I’m done rolling the dice. What makes sense for me are turnaround plays driven by market fundamentals—where the dynamics are primarily market-driven. Or, if it’s macro, it’s got to be a company that’s been absolutely pounded by the environment but is still alive and kicking. That’s where I can spot value and make a calculated move.

Managing the Anxiety of Sitting in Cash

Now, here’s the part that’s tough to admit—sitting on the sidelines when there are no good positions to take. Sometimes, the market just doesn’t offer anything worth betting on. No turnarounds, no pounded-but-surviving companies, nothing that fits my criteria. I’m just sitting in cash, and let me tell you, the anxiety creeps in. Am I missing out? Should I force a play just to feel like I’m in the game? That’s when I have to remind myself of something Charlie Munger once said: “The big money is not in the buying and selling, but in the waiting.” That hits hard. Waiting isn’t passive—it’s active discipline. To manage the unease, I focus on research during these dry spells. I dive deeper into potential sectors, refine my theses, and remind myself that cash is a position too. It’s protection. It’s patience. And it’s power when the right opportunity finally shows up. I also step away from the screens sometimes—go for a walk, clear my head—because staring at flat markets only fuels the itch to do something dumb.

What This Looks Like in Practice

Refocusing on trading—and protecting my foundation—means hard rules, clear boundaries, and a focus on sustainable, realistic outcomes in areas I can reasonably navigate. Here’s my approach now:

Reflections for the Day: Learning from Losses to Stay Grounded

These losses—like $100,000 in 2020 on oil, $130,000 in 2015 on MLPs, or the First Republic wipeout of $10,000—aren’t just numbers; they’re scars. They’ve drilled into me the need to stop gambling on what I can’t control and to protect my core at all costs. I’m not here to chase fantasy returns; I’m here to build a steady, sustainable base through trading—enough to cover my life and leave a little breathing room. That means patience, precision, and sticking to plays where market dynamics, not wildcards, call the shots. It also means managing the anxiety of waiting, trusting that sitting in cash is sometimes the smartest move I can make.

Have you ever taken hits like that $130,000 drawdown, betting on something that seemed solid only to get blindsided? Or maybe you’ve struggled with the anxiety of sitting out—how do you keep your cool when there’s nothing to play?

I’m feeling dialed in with this direction. It’s about building a solid base through trading, aiming for manageable wins in the right spaces, and keeping the noise—whether it’s wildcards, unbalanced risks, or my own impatience—out of the picture. What’s your safe zone, and how do you stick to it?