All too often, I write about the decisions that have turned out well in my life. This is a bit unfair as it paints an unrealistic view of my life. Today, I want to go in a different direction and write about the decisions that have not gone so well. Life is a continual learning process. My hope is that you can benefit from learning from my mistakes without having to experience them yourself.

The Biggest Mistakes of My Life:

Fat with friends

I am the fatty on the left.

Neglecting My Physical Fitness:

The biggest mistake that I have ever made in my life has been neglecting my body. Up until about five years ago, I almost never exercised. In college I lived off bagels, cream cheese, beer and bacon. As seen in the photo above, my body reflected that.

I had helpful friends offer to teach me how to workout (hat tip Ian and Patrick) but I continually turned them down stating that I just didn’t get anything out of exercising. I was being stupid and short-sighted.

At the time, my biggest perceived problems were social (why did no one want to date me?) and mental (why did I feel depressed?) If I would have listened to my friends and started to live a more healthy lifestyle, I could have made progress on curing my pains.

Eating healthy and exercising regularly are keystone habits that can have disproportional benefits on nearly every aspect of life. My biggest mistake has been not giving diet and exercise the energy it deserves.

Not Taking My Math Classes Seriously:

Throughout my schooling years, I failed about a fourth of my higher level math classes. At the time, I believed that math wasn’t applicable to real life and that I should put my energy somewhere else. This turned out to be horribly shortsighted!

Math is perhaps the only universal language and as such is almost universally applicable. My weak math skills held me back in University and continue to hold me back to this day.

My Biggest Business Mistakes

Structuring My Payments Incorrectly:

The biggest financial mistake that I have ever made was restructuring a specific contract to utilize a monthly retainer rather than a hourly payment structure. I was hired on as an expert witness on a potentially multibillion dollar patent infringement case and I completely underestimated how long the case would take. I had a signed contract with favorable terms but foolishly renegotiated it to use an hourly rate. This extra effort on my part, cost me tens of thousands of dollars.

Branding This Blog Around Life Lists Rather Than Bucket Lists:

When I first started this blog many years ago I made the conscious decision to focus on Life Lists rather than Bucket Lists. I knew that the term ‘Bucket List’ was already in the American vernacular but I foolishly thought I could create demand or common recognition for the term ‘Life List’.

This was stupid. While Life Lists and Bucket Lists are indeed different (Life Lists have deadlines), the difference is so slight that most people don’t really care.

As a result of my branding choice, I have lost countless organic visits to my website. My acquaintances who run blogs focused on the term Bucket List, run SEO laps around me.

My Biggest Timing Mistakes

Not Taking Command of My Investments Earlier:

While I knew I should have started investing earlier on in my life, I was intimidated with the complexity and risk of investing. I figured I either needed an expensive financial advisor (incorrect!) or an economics degree (foolish!) to succeed with the stock market.

It wasn’t until more recently that I decided that for my context, all I actually needed was low-fee index funds and automatic deposits to get my investments working for me.

If I would have realized this earlier, I could have had the massive power of compounding interest working for me earlier.

Not Learning About Storytelling and Videography Earlier:

It is a bittersweet reality for me that there are many things I have done in my life that I will never have the opportunity to do again. Doors have closed and the world has changed.

One of my greatest joys is sharing my stories with others. Unfortunately, I didn’t start studying storytelling or videography until after I had experienced a lot of my favorite stories. As such, I didn’t have the tools to share them properly with the people I cared about.

If I could start my Life List again tomorrow, this (learning about storytelling and videography earlier) would be the only thing I would do differently.

It humbles me a little bit to realize that the big mistakes above only cover the ones that I am aware of. I am sure there have been other missed opportunities or failed plans but for better or worse I either didn’t realize that they had happened or my mind has blocked them out.

Are you willing to share some of your past mistakes? If so, feel free to join the therapy party in the comments below.