Why I’m Glad That I’ve Been Unsuccessful

Being unsuccessful has helped me discover and appreciate the value of the more important things in life.


Zero Sour Grapes

The best thing that has happened to my life has been failing to succeed.

You know Aesop’s fable about sour grapes? The only thing that fabled fox and me have in common is that we both tried with all our might to succeed, but failed.

My most recent in a long line of unsuccessful attempts is my blog, TheZag.com. Thanks to Google algorithm changes, traffic has plummeted 95 percent over the past six months.

Crashing back down to earth sucks. But, like I said, so far it’s been for the best.

But What If?

Sometimes I wonder though, What if one of my many attempts had succeeded?

I certainly wouldn’t be writing this now—dictating, actually. Pause for a selfie:

Me making the L hand sign for "loser" in a selfie.

It’s 2:16 pm on a Thursday in North Vancouver. I’m between sets of an improvised calisthenics workout at a kids’ playground near my in-laws’ house.

If I were successful, I’d have a shirt on. I’d probably be at “real” work right now. Or maybe at Equinox with real exercise equipment and a personal trainer. Or maybe at a therapist’s office. 

Who knows? 

All I know is my lowly reality.

Unsuccess Is Bad for GDP, Good For Relationships

My wife, two sons, and I are temporarily homeless as we re-migrate from Cape Town to Vancouver. Hotels and Airbnbs are too extravagant for our meager income, so we’re crashing at Kim’s parents’ place. 

But my in-laws don’t mind. They could probably take or leave having me around, but they’re glad to have more time with their daughter and two grandchildren.

I don’t mind either. I like my in-laws. And I bet I like them more than I would if I had been successful, because then I wouldn’t have spent nearly as much time getting to know them.

I also don’t mind having to count on other people—to lend us stuff and babysit, for example. It’s the way life was until money entered the equation and made everything transactional. 

And I don’t mind being counted on by others. I rarely have “more important things to do,” after all. 

More Sweet Fruit of Unsuccess

As an unsuccessful person, I have lots of time. I get to spend a lot of it with my kids (who don’t realize I’m a loser yet), my wife (who seems to love me anyway), my friends and family (who evidently like me for who I am), and with my own little mind, thinking about things I wouldn’t have time to think about if I were too busy succeeding. 

As an unsuccessful person, I have minimal materialistic needs. Successful people have “FU money.” I’ve found something else that serves the same purpose: “FU frugality.”

As an unsuccessful person, I have a lot of flexibility. I take advantage of it to enjoy perpetual summers between Cape Town and Vancouver, to play beach volleyball with my friends whenever possible, and to mess around trying to find something I can succeed at.

And as an unsuccessful person, I have few wistful regrets. At least I’ve tried to succeed. I’m glad I did so rather than stay the comfortable course in my corporate career, wondering what life might be like had I made a leap. 

Am I Rationalizing?

You betcha.

That’s one of the sweetest parts of being unsuccessful: Constant failures have helped me build up a formidable psychological immune system. Thanks to its defenses, I’m in a bad mood maybe only five to ten times a year. I wake up practically every day feeling fresh, looking forward to another day—and to another leap toward that ever-elusive taste of success.

You Can’t Lose Once You Learn to Love Raisins

Despite all of this, I don’t want to continue being unsuccessful.

I want whatever my next attempt is to succeed. I want FU money. And I want people to look up to me and the ideas I share here. Years ago, I would have sacrificed a lot to achieve these lofty goals. But not anymore. Now I know the fruits of unsuccess are more important.

So unlike the fox in Aesop’s fable, I haven’t convinced myself those too-high-hanging grapes are sour. No, I continue to jump for them. But I spend even more time plucking the shriveled, low-hanging raisins nobody else seems to want. And I’ll let you in on a little secret:

They’re surprisingly delicious.

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About the author

👋 I'm Chris. Everything you read on TheZag.com is my fault. This site is like a gym for your comfort zone, full of challenges to make your status quo sexier. Join my 'Consider This' newsletter for a fun new challenge every 10 days. Try it!

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