They say Occam’s Razor is the idea that the simplest explanation is usually the right one. Well, the simplest explanation here was: “I got hustled.”

Checklist for Avoiding Dumb Decisions:

• ✅ Gut check
• ✅ Due diligence
• ✅ Proof of funds
• ✅ Collateral
• ✅ Second opinion
• ✅ Sleep on it
• ❌ Ignore all of the above and lose five grand

Back in 2014, I was 25, newly unemployed by choice, and full of “follow your passion” energy. I had just left a great corporate job to move back home and focus on an organization I helped build from scratch. Life was... dare I say, peaceful?

Until it wasn’t.

The Setup

One evening, I got a message on LinkedIn from someone I hadn’t spoken to in years. Let’s call him Mike. He asked me to call him urgently and meet up that night. Weird, but fine.

Mike told me he was buying a new house, but the buyer for his current place had backed out last minute. He needed $21K to close and had apparently gathered $16K from others. He just needed one last $5K to bridge the gap by noon tomorrow.

He promised 10% interest in 30 days. Guaranteed.

I felt skeptical... but then he said his wife and kids really loved the house and he just wanted to make them happy. And that? That got me.

I had some savings sitting around earning 2%. So I figured: hey, help a family and earn $500 in a month? Win-win.

Spoiler: it wasn’t.

I drafted a promissory note (because I was “being smart”), handed over the cash, and bought a new suit to celebrate my future returns.

The Gut Punch

Ten minutes later, a mutual friend finally returned my call:

“You gave him money!?”
“Yeah?”
“He owes me $15K. Filed for bankruptcy last year.”
🫠

Turns out there was no dream home. No buyer. No other lenders. Just a long list of people getting played.

The Fallout

I was crushed. Financially, sure — but the embarrassment hit harder. I stopped trusting people. I got short with friends and family. I lost confidence in myself.

I took it to small claims court and won. But unless your debtor has a job or assets, a judgment is basically just a certificate of regret.

What I Wish I Had Done Instead

Here’s the checklist I wish I had with me at the time:

Checklist Before Lending Money

• ☐ Ask: why me, why now?
  ☐ Request documentation
  ☐ Talk to someone smarter
  ☐ Don’t lend to someone you haven’t talked to in years
  ☐ Get collateral
  ☐ Trust your gut

What I Gained (Other Than Debt)

As painful as it was, this was a $5K masterclass in:

• Emotional decision-making
• The dangers of trying to “be the hero”
• Why every major choice should run through a checklist

That $500 suit I bought to celebrate? Still fits. Still looks great. Shame it was funded by one of the worst decisions I’ve ever made.

Final Thought

Money doesn’t make you a better person — it just turns up the volume on who you already are.

And now? I don’t make big decisions without a checklist.