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Mistakes are a side effect of the human condition. As a human whose been in this condition for 30+ years, I’ve had my share of doozies.

Though I will happily lament about them, it was only recently that I tried to reframe them. I thought these big thoughts, not on my own but as prompts from a book called, Failing Forward

I find things of interest to percolate on when I read a self-help book, rarely do I find criticism in others musings. Just because I’m not a fan girl over it doesn’t mean it sucks, it just means someone else is a fan girl.

Failing Forward provides insights into how to be better at failing. Failure is a part of learning, success, and all other worthwhile endeavors. 

So in hailing from others’ insights, I reflected on the best mistakes and how they’ve become the best outcomes.

The best mistake for my finances was cashing out my retirement account.

I revisit this mistake more times than selfies at the Grand Canyon. 

And my pride is as wide as the Grand Canyon when it comes to my personal finances because I save 28% for retirement and have accounts for all the biggies including bills, travel, and emergencies. I’ll be punching out of work and a mortgage early. 

So to reflect on that one time, I was so bad with money that I couldn’t save and instead cashed out the only asset I had, is harder to swallow than cherry cough syrup when I don’t even have a cough. 

It was a mistake.

It was a painful mistake that feels like the lowest point in my financial journey. Afterward, I slowly turned the trajectory from a failure into a moment of failure. One low moment that I use as a touchstone to make better financial choices. 

Plus, what an epic story to tell to go from zero to hero: from cashing out retirement early to retiring early. 

I didn’t plan on writing that story, yet some of the best stories are the ones that I never planned to write. 

The best mistake in my love life was dating bad boyfriends.

Every girls got ‘em. Ladies have direct or indirect experiences with dating a bad boyfriend.

I’m no different. 

When I was younger, I let someone else determine my self-worth instead of dictating my own. 

I cycled through crummy relationships and was relieved to move to a different state, so I didn’t have to deal with any accidental run-ins. 

During the last big break when my time zone was different from the ex’s, I decided drastic changes were necessary. I needed to figure out what I wanted and was determined to hold my ground until I found it.

I wanted a partner who:

Was already the right thing instead of hoping that he’d change for the right thing;

Valued me more than my ability to cook and clean; and

Enjoyed my company and wanted to spend time with me instead of spending it all with his friends. 

It took 2 years to find a good fit, but it was worth it.

Now, I’m happily married. I can say that with sincerity and intensity because I know what it feels like to be in a relationship riddled with more issues than 2020.

It was a mistake to be in a relationship where I had to sacrifice so much for dudes who cared so little, I’m fortunate to have learned from those mistakes. I’m a better woman, partner, and spouse because of those hard lessons in relationships. 

The best mistake for a job was working somewhere mediocre.

Mediocre work is the most dangerous work. 

It’s work that pays just enough to not make bank accounts cry, doesn’t quite challenge full potential, and has plenty of nice people yet no deep friendships.

I ended up tumbling around in a mediocre job for 3 years before I finally flopped away from it. Even now, thinking about being stuck in a place that I didn’t love feels sad. 

Being in such a lethargic state for 3 years is a professional mistake, though I did learn valuable lessons. Towards the end of my 3-year tenure, I started dabbling in side jobs that scared the sneeze right out of me. I felt forced into trying things that blew up my comfort zone because I was lulled into boring for too long. 

To shake up boredom, I had to do something different. 

Vastly different. 

Like teaching art to underserved youth when I knew nothing about either. 

My lack of experience scared me. In the end, it was the best mistake I ever made. It taught me to try things even when it feels bigger than the Sunday scaries because it might just turn into a passion.

The best mistakes led to the greatest outcomes.

From personal to professional, the start of the shift isn’t one I would have picked. I wouldn’t pick dumping my best asset, having bad boyfriends, or a mediocre job. 

But that’s what happened. 

When I reflect on these items, what keeps them together as a cohesive whole, is that once the event happened, the next chapter was significantly better than the last. 

It was like I had to go through a rough patch before I was granted something bigger and better. Or I had to work hard before I could get the prize at the end of the drama.

The prize was worth the wait.

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