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3 Lessons I Learned from Failure in My 20’s

Sometimes the most valuable lessons are learned through struggle and failure.

When I was growing up, I always assumed I would go to college, graduate, get a good job that I liked, and work my way through a rewarding career.

The first part went as planned. I went to college and graduated in 2002, but the plan fell apart shortly afterwards.

My first four years after college, I had four different jobs. Thankfully, I always had a job and was able to pay the bills, but I was constantly struggling to find a job that I saw as a true career. I’d be in a job for a while, see that I was going nowhere, and find another job that I was willing to take a chance on.

A few years after graduating college, I felt like I had made absolutely no progress, and that was depressing. I was still in an entry level job making enough to support myself, but not able to save anything. Even worse, I had very little hope that things would improve.

At that time, when I was about 26 years old, I started a side hustle to make money as a web designer. Pretty quickly, I realized that I loved being able to work for myself and I decided to see if I could turn it into a full-time income.

My web design side hustle transitioned into internet marketing and blogging, as well as design and website maintenance for a few clients. After about a year and a half of hustling, I was able to leave my full-time job and embark into the world of self-employment.

It’s now been more than 11 years since I left that job, and my life has changed in a lot of ways. Thankfully, I have more flexibility and my income has been much better than what I made at any of my low-paying jobs.

The years in my 20’s were extremely frustrating and challenging, and definitely not what I expected to happen after college, but I learned a lot through the process. Here are three of the biggest lessons that I learned from my career failures after college:

1. The Grass Isn’t Always Greener On the Other Side

None of my jobs lived up to my expectations. When I realized that a job was not going to get me what I wanted, my response was to look for another job that I thought would be better.

Unfortunately, taking another job never solved any of my problems. Sure, some things about those jobs may have been better than the previous job, but I never felt fulfilled or satisfied with any of them.

2. It’s Better to Be Really Good at One Thing Than “OK” at a Lot of Things

One of the jobs that I took was a sales job, and I sucked at it. I knew I wasn’t good at sales, but one of my reasons for taking the job was because I though it would make me more valuable if I could improve in one of my weak areas. That was wrong.

I did improve a little, but I was never going to be a top-producing salesperson. Simply being average, or even pretty good, at a lot of different things really doesn’t matter. It may seem appealing to be a jack-of-all-trades, but it really doesn’t make you extremely valuable.

You’ll be far more valuable if you focus on developing your strengths and you become elite at something in particular. If you’re a world-class software developer, it doesn’t matter if you’re terrible at everything else. Your strongest skills determine your earning potential.

After I started my own business on the side, I found some things that I’m good at, and for the past 11+ years I have been working at continually developing those skills and pursuing passive income ideas. That has allowed me to increase my income and spend my time working on things that I enjoy, rather than forcing myself to do a job that doesn’t suit my strengths.

3. Trust Yourself

Leaving my full-time job was a hard decision. I walked away in 2008 when the economy was pretty bad. A lot of my friends had lost their jobs and were struggling to find work. I knew that my business needed to succeed, or else I would probably have trouble finding a decent job.

Because of the risk, I played it conservatively and waited until I could completely replace the income from my full-time job. That worked out pretty well, but many times I’ve wondered why I didn’t take a little bit of risk and leave my job earlier. In the end, I did trust myself enough to leave the job, but if I had invested in myself earlier, I would have had a bit of a head start with my business.

So while I didn’t accomplish a lot during my 20’s and it wasn’t what I was expecting, it was a very valuable time of learning some hard lessons.

Looking back, I believe those lessons led me right to where I needed to be. If it hadn’t been for all of the frustrations that I experienced during my 20s’, I don’t think I would have been motivated enough to branch out and try self-employment, and I would have missed out.

Photo by Vasily Koloda / Unsplash license

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