Why I Regret Taking a Gap Year

The president’s daughter is taking a gap year. I think that’s amazing. I think you can learn more in a gap year than you can in fours years of formal education.

I wish I had taken a gap year before marching off to university with no idea what the real world was like or how I wanted to contribute to it. So after stumbling around trying to figure out how to be an adult, I finally took my gap year at 28.

And here’s why I regret it:

Momentum is everything. Momentum was easy in school when one semester pushed me to another and another until finally I had earned that precious piece of paper that was supposed to be my promise of a good job and a good life.

And then work came, jobs like school semesters one after another as I constantly searched for something that would make me more money or make me more fulfilled.

Until one day I stopped. I ground to a halt. I quit and didn’t get another job. I took a gap year to figure life out, to figure it out for good so I’d no longer feel like I was wasting my one precious, wild life.

Surely there was a way to make money and be fulfilled, I thought. And surely I can figure it out in a year.


That was funny.

I still believe there is a way to both make money and be fulfilled, but sitting back and thinking about it for a year doesn’t make it happen.

With my year up, I’ve lived the meaning of the cliché, “A rolling stone gathers no moss.” I stopped rolling, and I gathered a lot of moss.

Like a baby with chubby thighs poking out of the holes of a baby swing, my feet are dangling helplessly above the ground with no concept of how to pump the swing into movement.

I’m just sitting here like a jellyfish all fat and floppy. My muscles have atrophied. My thick skin has lost its callouses. I feel like such a baby.

When I started my gap year, I was on top of the world. I felt like I could do anything, like I had infinite power to make things happen and infinite time in which to do them.

But I had one huge problem. I didn’t know what things I wanted to make happen. I had no direction, no plan, and no exit strategy.

There’s a Simpsons episode where they go to England and get stuck in a massive roundabout. Homer tries to get out of all the lanes going round and round, but his clueless Americanism gets them so stuck they end up in the roundabout all day, driving in circles and getting absolutely nowhere.

I feel like a dumb Homer. A gap year will be great, I thought, and I jumped into the roundabout. Without knowing how to navigate the roundabout, I’ve gotten stuck in it, dizzy and frightened by all the traffic.

Sure, I used the time to pull out some maps and figure out what route I want to take. I analyzed how to make it into the stream of cars heading in my desired direction. But do I know how to actually steer my car out of the roundabout without getting crushed by the oncoming traffic? Oh, crap.

I wish I had kept up my momentum coming out of my last job. I wish I had taken a step, any step, without worrying about whether it was the right step, just so I could keep moving. At least then, it wouldn’t be so hard to shift gears and change direction when the time came.

Of course, the grass is always greener, you can’t have your cake and eat it too, and you made your bed so lie in it.

I think all that gibberish means that regrets are unproductive. There are a million things I learned during my gap year that I wouldn’t have learned had I jumped right into another job. So it was good.

But if I could do it over again, I’d use the time more wisely. I’d make sure I had a plan and a specific goal. I’d keep the rock rolling so the moss wouldn’t gather, and I’d definitely learn how to drive through a roundabout.


2 thoughts on “Why I Regret Taking a Gap Year

  • May 16, 2016 at 12:59 pm

    I appreciate ALL of this, Jessica … particularly the Homer Simpson reference! Seriously, though — Well written!

    • May 16, 2016 at 8:27 pm

      Thanks for saying so, Michael! 🙂


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