Out with the old, in with the new: Figure out your biggest mistake

In December and January, The Simple Dollar is posting a daily series focusing on specific activities you can do right now to set the stage for a great 2011. Out with the old, in with the new.

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Homer Simpson, who immortalized that 'D'oh!' moment of sharp regret, was immortalized on U.S. postage stamps. In this May 7 file photo, Fox Studios and U.S. Postal Service representatives unveiled the new collector postage stamps.

3. Figure out your biggest mistake.

What one element of your life is the one element you would give anything to fix?

I’m not talking about the things you can’t fix, like incurable diseases or the like. I’m talking about things that, with some amount of luck or effort or intervention of others, could see significant positive change.

For the past few years, my biggest “mistake” has been my weight. Frankly, it oscillates. I’ll do quite well for a while, “chaining” good days together a la Jerry Seinfeld, but then something will break that chain for a few days and I’ll find my weight spiraling back quite quickly, undoing all of my progress.

It’s my biggest personal mistake, in my opinion, and it’s one that bothers me on a daily basis.

Of course, this is just one among many mistakes in my life that I regret. I can point to several other things that cross my mind at various times, from broken relationships to poor use of my own time.

When I reflect on them as a whole, though, my weight stands out, not so much as a personal appearance thing, but in terms of my ability to be a healthy father for my children.

If you’re like me, you’ll find that the one key mistake or problem in your life underpins many other smaller issues. Perhaps your debt load is keeping you from quitting a job you hate. Maybe your weight concerns are keeping you from joining a basketball league with many of your friends. Maybe your relationship with your parents is keeping you from enjoying time with your extended family.

That’s why it’s important to ask yourself if the big mistake you’re identifying at the moment isn’t really caused by something else. Maybe your inability to advance in your career is tied to poor public speaking skills, and those poor public speaking skills are also tied to your deep discomfort at being asked to be someone’s best man at their wedding.

It’s also important to remember that the purpose of this thought process isn’t to make yourself feel bad. The purpose is to dig down to that one thing in your life that you have control over that is causing the most negative elements in your life.

Spend some time thinking this through. Make a list of the things that bother you in your life, and see if you can figure out which ones are causing others. You may find that one or two things are at the root of everything if you stick with it enough.

Tomorrow, of course, we’ll talk about what to do once you figure out that one biggest mistake in your life.

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