Paying for the Same Mistake Twice

Every month, I make payments on debt from the past year.

I can make the payments. They hurt, but that’s not really the problem.

The problem is what one particular payment represents.

I borrowed money to make an investment. I believed the opportunity was worth the risk.

I was wrong.

I lost the investment quickly, but the loan didn’t disappear with it. I’ll be paying for that decision for a few more years.

And every payment gives me another opportunity to remind myself:

You really screwed that up.

Not All Debt Tells the Same Story

I have other debt from the past year.

Some of it came from helping cover my mother’s long-term care before other support became available. I don’t like having that debt either, but I don’t judge myself for it in the same way.

I made a choice during a difficult situation. There was a need. I helped cover it.

The investment debt feels different.

I chose to take that risk.

Nobody needed me to do it. There wasn’t an emergency. I made a financial decision because I thought I could turn borrowed money into something more.

Instead, I lost it.

On a balance sheet, debt is debt. There are balances, interest rates, minimum payments, and payoff dates.

Emotionally, these debts aren’t the same at all.

One reminds me of a difficult responsibility.

The other reminds me of what I consider a failure.

I Should Have Known Better

That’s probably what bothers me most.

I’ve been in serious financial trouble before.

Years ago, after a combination of business problems, legal expenses, and my own decisions, I found myself hundreds of thousands of dollars in debt.

Getting out of that situation changed how I lived.

I learned to live below my means. I became much more cautious about debt. I learned that earning more money doesn’t necessarily create financial security. I learned to value experiences more than things.

I thought I had learned this lesson.

Then I borrowed money for an investment and lost it.

So the voice in my head doesn’t merely say:

You made a mistake.

It says:

You should have known better.

And maybe I should have.

That’s uncomfortable to write.

But knowing better and consistently doing better aren’t the same thing.

Experience doesn’t make me immune to optimism, ego, greed, fear, or simply being wrong.

In fact, one reason I’ve made “check my assumptions, ego, and greed” an explicit principle in my life is because I apparently need the reminder.

Principles aren’t descriptions of perfection.

They remind me how I want to choose.

I Was Making Two Payments

Recently, I realized I’ve been paying for this mistake twice.

The first payment is financial.

I borrowed the money. I owe it. I need to repay it.

No philosophical insight makes that obligation disappear. I made the decision, accepted the risk, and now I have to deal with the consequence.

That payment serves a purpose.

Every payment reduces what I owe.

But I’ve been making another payment too.

I screwed this up.

I should have known better.

Look at how much this mistake cost me.

I failed.

That payment doesn’t reduce anything.

The balance doesn’t go down.

The interest doesn’t decrease.

Nothing gets repaired.

I just pay it again next month.

Accountability Isn’t the Same as Punishment

I don’t want to turn this into a story about forgiving myself and pretending everything is okay.

I made a bad decision.

Living deliberately means owning that.

What did I believe when I made the decision?

Which assumptions did I fail to challenge?

Was I appropriately considering the downside?

Did optimism become confidence without enough evidence?

Did ego or greed influence how I evaluated the opportunity?

What boundaries should have prevented me from taking that much risk with borrowed money?

Most importantly:

What will I do differently because I got this wrong?

Those questions are useful.

They turn a painful experience into information.

That’s accountability.

But I’m beginning to question whether repeatedly telling myself that I failed serves the same purpose.

Once I’ve understood what happened and changed how I make similar decisions, what exactly does another year of self-punishment accomplish?

Maybe nothing.

Worse, it might distort the decisions I’m making now.

Don’t Let Yesterday Make Today’s Decision

I’ve recently been considering whether I should simply pay off some of my debt now rather than continuing to make payments over the next several years.

There are legitimate financial questions involved.

What’s the interest rate?

What would I give up by using that money now?

How much liquidity should I maintain?

What risks am I creating or eliminating?

Those are questions I can analyze.

But there was another question hiding underneath them:

Do I want to pay off this loan because it’s the best financial decision, or because I desperately want the reminder to disappear?

That stopped me.

Because those aren’t the same decision.

If eliminating the debt makes financial sense, then I should consider doing it.

But if I’m willing to make a worse financial decision today because I’m ashamed of a financial decision I made yesterday, I haven’t necessarily learned anything.

I’m still letting the old decision control the new one.

Just in a different way.

Failure Should Produce Information

I’ve written a lot about living fully by living deliberately.

That doesn’t mean making perfect choices.

I’ve made enough mistakes in my life to know that won’t happen.

Being deliberate means reflecting, choosing, observing what happens, and adjusting.

Sometimes I will choose badly.

Sometimes I’ll misunderstand the situation.

Sometimes I’ll discover that an assumption I felt confident about was simply wrong.

Sometimes I’ll know better and still screw it up.

The important question isn’t whether I can eliminate failure.

It’s whether failure makes me more capable.

What do I understand now that I didn’t understand before?

What will I recognize sooner next time?

What boundary needs to exist because I now know something about myself that I didn’t want to admit before?

What should actually change?

If I can answer those questions, then the mistake has produced something useful.

I don’t need to keep reopening the wound to prove that I’ve learned from it.

Pay the Debt Once

I still owe the money.

I don’t particularly enjoy writing that sentence.

Part of me would much rather tell a story where I made the brilliant investment, paid off the loan, and congratulated myself on being clever.

That’s not what happened.

I took the risk.

I got it wrong.

I lost the money.

Now I have to pay it back.

That’s the financial debt I owe.

What I’m reconsidering is the other debt I’ve imposed on myself.

I don’t think accountability requires spending the next several years treating every payment as evidence that I’m a failure.

The mistake happened.

The consequence is real.

The lesson should remain.

But maybe the shame has already done whatever useful work it was going to do.

The loan will eventually reach zero.

My job is to make sure the lesson remains after the balance disappears, not the shame.