The Struggle of Second-Guessing Yourself

I’ve been thinking a lot recently about my choices. And how much I worry about my choices after the fact. I’m a consistent second-guesser. I usually stumble into my decisions rather than consciously make a choice, which only compounds the aftermath of my descent into second-guessing hell.

It isn’t the way I’d like to live my life, but I have such a hard time believing that what I’m actually doing is a good idea. Let’s look at some examples:


  • DECISION: I leave my first part-time job (a graduate assistantship) and an MBA program because I got a full-time job doing what I actually want to be doing and the schedules just didn’t work together.
  • SECOND-GUESS: Could I have actually just toughed it out working like 60 hours a week plus going to school full-time? Did I take a dead-end job over a degree?
  • DECISION: I agree to a promotion because it seems, in theory, like it will advance my career.
  • SECOND-GUESS: The details of the promotion are vague at best and purposely veiled at worst. Perhaps I should have just stayed doing what I’ve been doing. I’ll hurt my coworkers because they’ll have to take on many of my old responsibilities.
  • DECISION: I decide to stay with 4 roommates that I’ve never met at a conference and sleep on an air mattress in order to save money.
  • SECOND-GUESS: Well…this sounds like a terrible idea from the beginning. You don’t even like people! Why would you want one unknown roommate, much less four!
  • DECISION: I buy the red skirt.
  • SECOND-GUESS: Maybe the red skirt won’t fit me? Maybe it’s too gaudy? Did I really need a red skirt? Could I have gotten by just as well with my pink skirt?


As you can see, some of my second-guessing is warranted (although the whole 4 roommates and sleeping on the floor thing actually worked out just fine), but most of the time it’s either “too little, too late” or just unreasonable.   But how do you know that you’re making the right decision when you’re making the decision?

Second Guessing 2

This is my daily struggle. I keep thinking I’ll get better at it with time, but I’m almost 26 and it looks like I’m still in the same uncertain boat. The biggest problem with being a “Second-Guesser” is that it makes it impossible for you to take big risks. And many times big risks are the only way to make lasting and worthwhile change. As I mentioned before, most of my decisions are not consciously made but usually stumbled into. Because of this, legitimate change just doesn’t happen for me. (Legitimate change doesn’t come from accidentally making a decision). Legitimate change takes a risk, but I’m too busy second-guessing my pseudo-decisions to take any kind of risk!

So this is a problem. For me. Maybe for you too. Or maybe you’ve got it all together. If so, I’d really love to know how! More power to you!

Second Guessing 3


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