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The Best Interest » Self-Inflicted Wounds

Self-Inflicted Wounds

Friend-of-the-blog Tyler broke his hand a couple weeks ago…on his birthday, no less! Ugh. What a bummer. Sorry, Ty!!!

Sure, there’s the physical pain of a broken bone. But Tyler also felt the mental frustration of knowing, “I slipped and fell. I took the wrong step. This wasn’t an unavoidable, external mistake. This is a self-inflicted wound.”

P.S. – one remedy for a broken hand is proposing to your future wife…congrats Ty & Kate!

Self-inflicted wounds are a double-bummer. Bummer #1 is the wound itself. But the physical pain is compounded by the knowledge that you did it to yourself—and that’s Bummer #2. It’s the knowledge that the injury was avoidable. And the knowledge that your own mistake will cascade into weeks, months, or years of negative consequences.

But I want to convince you that “Bummer #2” has little utility in our lives. You can’t go back in time to undo the mistake. Tyler can’t unbreak his hand. So what’s the use in feeling ongoing regret?

I think the smart emotional response not be prolonged, but brief. Realize your mistake, learn your lesson, commit to changing future behavior, and move on. 

Self-Inflicted Financial Flaws

The world of personal finance is full of self-inflicted wounds.

  • We spend money on stupid stuff we later regret.
  • We borrow too much for our houses, our cars, or our education.
  • We invest too little money or start investing too late in life.

The obvious consequences appear on our balance sheet and in our bank account. We don’t have as much money as we’d hope.

The secondary consequences haunt our thoughts – “If only I bought Bitcoin in 2012 and could buy four Jet Ski’s like the Jones family…”

But just like Tyler’s broken hand, the “if only” regrets have limited utility. They’re only worthwhile if they help you learn for next time. Beyond that, you’re uselessly crying over spilled milk.


My go-to overspending story is that I bought a hot tub in 2017. I overspent then and underutilize it now. But I’ve learned some amazing lessons:

  • I have a psychological weak spot for a good a sales pitch (and you might too)
  • Find the root of your desire. Turns out, I thought hot tubs were so much fun because my limited experience with them involved groups of friends. It’s not the hot tub itself that’s so fun. It’s the friends! And you don’t need a hot tub to hangout with friends.
  • Good deals are always out there. I bought the Mercedes of hot tubs. Should have gone for the used Honda.

I don’t regret buying the hot tub. But I have learned from the experience.


“If only I knew at age 18 what I now know at 24, I never would have borrowed $100K for college.”

I see this sentiment a lot. It’s a tough pill to swallow.

The desire to change past decisions is so strong, and yet the ability to change past decisions is nonexistent. And if you let it, this kind of frustration can consume you.

So, what can you do about it? A few ideas:

  • Not make the same mistake again.
  • Help others avoid the same mistake in the future.
  • Find an optimal path “out of the woods”

Learn from the past, lean into the future.

Further reading: Curses, Miracles, and The Best Interest’s Student Loan Solution

Too Little, Too Late – The Regret of Inaction

Now that we’re 12 years into an amazing stock market bull run, I’m reading tons of thoughts like,

Damn. I missed my chance to invest. And that means either 1) I’ll never get another chance like this again or 2) I should wait for the market to fall before pulling the trigger and investing.

– Many People Right Now

This thought process is easy to empathize with but thankfully easy to refute. For evidence, I highly recommend you read these two articles:

The current stock market is not a reason to feel like you shouldn’t be investing.

Self-Inflicted Growth

I want to leave you with one more question:

What about all the things you’ve done right in your life?

It’s easy to focus on the negatives in life. We’re perfectionists. We seek growth and improvement. Our mistakes are low-hanging fruit, ripe for fixing.

But does it do us good to focus on the bad stuff 100x more than we focus on the good stuff? I doubt it.

So next time you’re wallowing in self-inflicted guilt, remind yourself of the amazing contributions you’ve made to your world. And know that you’re making strides to be ever better.

Thank you for reading! If you enjoyed this article, join 8000+ subscribers who read my 2-minute weekly email, where I send you links to the smartest financial content I find online every week.


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4 thoughts on “Self-Inflicted Wounds”

  1. Great post. You are 100% right. It is hard because we tend to expand the negatives in your mind and minimize the positives…but you have to do it to move on.

    At some point you have to leave the past in the past and just move forward. We all make mistakes, but it should never derail you or stop you from pursuing your dreams.

  2. Thanks for the post.

    I feel like all of us, especially in the financial world, make a ton of mistakes and everyone has a ton of regrets. I think the key is to let go of the pain so we stop injuring ourselves like you say, but never forget the lesson.

    1. Angie, you’re quickly becoming a top reader! 🙂

      Thanks for writing in. Like you said – a big key to to stop the negative (let go of pain) and start the positive (healing).

      All the best,

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