Dealing with Regret

First World Regrets

How does anyone do this? I’m just 25 years old, yet in those short 25 years I’ve assembled an extraordinary number of small regrets to overanalyze.  At a moment’s notice, my mind is ready to go rogue and ruin my focus and mood, dredging my memories and pulling up body after dead body.

Too many of these regrets have to do with my time and money.

  • “Remember when you bought your home and paid $7,000 in points on the mortgage? Then sold it after a little over a year? Look at how well the housing market has done since then! Oh, and you’re renting? You’re never going to have the money to live the life you want now. And where’s that Tiny House you were living in now?”
  • “Remember when you moved to Seattle? Then to California? Then back to Seattle? Remember how many days you spent packing, driving, and at the DMV? Remember how much effort was spent and money wasted? You’re throwing that time away.”
  • “Remember how your siblings are all going to graduate school, paid for without student loans? They’ll be way smarter or making more money than you in a few years. Or both.”

Time and Money. But mostly money- you know, that thing I say I don’t care about.

I’m 25- I’ve got lots of time. 40 years of time left is conservative; 60+ is more likely.

  • “Yeah, there’s plenty of race left. Good luck making up that lead though.”

I’m white, male, come from a well off family, and got great grades and honors in school, and give a mean handshake. It’s not worth bragging about, but I’m uber-employable. I’m in a D.I.N.K. family (look it up if you need to). I started my own company 5 months ago and am making money, although not as much as I’d like.

  • “Yeah, but good luck catching up to those Amazon employees. They’re always going to make more money than you are. Good thing you won’t need to bid against them for a home- oh wait, you sold your home, didn’t you?”

I know my mind’s voice is a bit unreasonable, and more than a bit of a dick. But how can we shut him up, and where do we go from here?

One way would be to look on the bright side- taking the same decisions I berate myself for and crafting a more positive narrative.

  • “Remember how alive you felt when you walked Downtown? You can live there now! You can live anywhere you want!”
  • “Remember what your mom said after you and your wife moved to California? ‘I feel like I didn’t know Jessica until you moved down here- I’m so glad I know her now’”
  • “Remember what you said about grad school, and how you’ve always wanted to be an entrepreneur and build a business that gives you more freedom and decision making power- kind of like the business you’re running now?”

Taken this way, I’m trying to beat my regretful mind at its own game. I’m screaming good choice as loud as I can, trying to drown out my regretful mind’s screams of bad decision! I’m not sure who will win, but I have a feeling that there is a better way.

This Week’s Challenge:

This post isn’t about regrets themselves- my regrets are minor. This is about the mental game. If we can’t control our minor regrets, how will we function when things really take a turn for the worse?

Do you have problems with regret, over-analysis, and rumination? If you struggle with this, let me know in the comments. If you don’t, why do you think that is, and do you have any wisdom to share?