Failure is a scary subject in general. Making a list of specific failures? That can be downright paralyzing.

I’ve failed a lot. Here are some of the more notable examples:

  • At age 15 I worked part-time for a mechanic doing oil changes and other light work. I quickly became bored of the job and quit paying attention. My boss let me go after I broke a lot of electrical connections and narrowly escaped making a few disastrous mistakes.
  • At age 16 I got a couple of well-paying jobs maintaining property for retired clients and a business retreat. I didn’t like the physical labor, and worked the minimum time necessary. I eventually quit to “pursue other opportunities”.
  • My other opportunities ended up being in fast food. I worked at two different pizza delivery companies in the lowest-paid positions in the companies. I quit these jobs because I hated the drama and was bored.
  • Next I worked for my dad’s remodel business. There were only three of us in the company, but I spectacularly failed to express any interest in construction management or trades. I quit since I was literally falling asleep standing up on the job (okay, there were some underlying health issues here too).
  • At 18 I was hired as an office manager for a construction company. I had no training or experience, and made several catastrophic mistakes including letting a 5-figure check bounce. I was fired after the first month.
  • I got hired as a graphic designer at a growing web development company. Again, I had no experience or training, and I bungled my way through a year and a half with varied results. Eventually I decided I could do a better job running a business than my boss, so I quit.
  • Next I freelanced as a logo designer and marketing consultant. I lost money every month I was in business (so much for doing better than my boss), and several consulting clients didn’t see any measurable results from my work.
  • During this same time I discovered that I could make up to $100/hour playing piano at assisted living facilities. I completely failed to capitalize on this by convincing myself that I needed a “real” job or business.
  • In 2012 I started offering social media consulting. I signed up a single company. I failed to follow up on what could have been a profitable business, and dropped that client after two years without ever converting another client.
  • Also in 2012 my brother Benjamin and I started working on a web application called LaunchCaptain. We dedicated our nights and weekends to the project, and invested our own money to build a section of the app. After 3 years of sporadic work and several thousand dollars in expenses, we finally let it slip under the carpet.
  • In 2012-2013 I was in Williston, ND during the oil boom. While others I knew made six figures in a few months, I worked the equivalent of a minimum-wage job and left with nothing to show financially for my time there.
  • In June 2014 I purchased a 1991 Nissan 300zx at a high price. Within a year it lost 75% of its value. Instead of accepting my loss, I let it sit and mold for a year, reducing the value even more.
  • In May 2015 I started with dreams of turning it into the ultimate musician/producer/songwriter resource. I published a few posts, grew a small Facebook fan page, and consequently lost interest and dropped the idea entirely.
  • In June 2015 I created a Patreon page for my original music videos. I recorded 3 introductory videos and got 2 Patreons to agree to give me a total of $3 when I released the first music video. I have yet to release a music video.
  • The company where I worked started the process of a merger with another successful company. Instead of finding a way to stay on board, I decided it was high time I took command of my own destiny in the form of my second business. Today, the merged company is doing well; I, on the other hand, went broke within 18 months.
  • In September of 2015 I sold around a dozen hours to a client on retainer. Through an oversight I failed to communicate the time limit to my contractor, resulting in $1000 in uncovered costs and up to $5000 in lost revenue.
  • In 2016 I lost money every month I was in business. Yay for being my own boss.
  • In June of 2016 I “pivoted” from website management to video production, a completely unrelated field I had virtually no experience in. I spent two months attempting to get traction and gave up.
  • In August of 2016 I admitted to myself that my business had failed, but was too egotistical to settle for just paying the bills. I burned two months applying for positions I wasn’t qualified for and turning down decent jobs.
  • In September 2017 I committed to a second month of daily videos on my personal YouTube channel; I only published four.

This is by no means a comprehensive list. I’ve highlighted a lot of my professional failures because for me they’re easy to talk about. It’s a lot more difficult to measure, much less discuss, personal failures: times I’ve let friends down, burned metaphorical bridges, or missed an opportunity to do good.

The message from all this is pretty simple: don’t let failure stop you. The past is unchanging. You and I live in the present; it’s the only portion of time that we can even pretend to have influence over, and it’s our choices in the here and now which write the next chapter of our history. Don’t look to the past to define you. Seize the moment.


Want to learn more about failure? Check out these links:

Gary Vaynerchuk explains the best way to deal with fear of failure
Seth Godin’s six random ideas that will help you fail better
Failure – a Creative Mornings series