7 Times I Failed!

Most people, myself very much included, tend to use social media in a way that disproportionately glorifies our successes, wins, and highlights.

A quick scroll on any platform will lead you to believe that EVERYONE is crushing life 24-7.

And while I love the life I live (and live the life I love), I can readily acknowledge that’s not an accurate representation of the full picture of my life.

It’s not that the successes you see aren’t true, it’s that they have been curated.

People, once again myself included, only post what they want you to see.

But that’s not real life.

Life has ups and downs, highs and lows, joys and pains.

As human beings, we inevitably experience failures, setbacks, and heartache… we get in our own way, make boneheaded decisions, and say/do stupid stuff.

No one is batting a thousand in life.

Even the ‘Instagram Bro’ in an Armani suit, sitting on the hood of a Bentley sandwiched between two bikini models, in front of a private jet holding wads of $100’s - even ‘he’ isn’t crushing every aspect of his life 100% of the time.

Thus, I made the deliberate decision to write this post to give you a behind-the-curtain look at my own missteps, mistakes, and the things that did not quite work out the way I had hoped.

Each of these ‘failures’ - as painful, difficult, or disappointing as they were - have shaped me into the man I am today.

They haven’t made me weaker - they have made me stronger (and hopefully wiser)!

They are just as much a part of my life and who I am as my successes.

And for that I am grateful.

And while I have over three decades under my belt as an adult… and too many failures to count (including divorce, massive financial debt, and being hired & fired from a dream job)… here are 7 more recent failures I’ve experienced in the past three years:

1. While I’m very proud of the speaking business I’ve built… this is the second straight year I’ve failed to reach my goal (both in number of total events and in total speaking revenue). Granted, I set a very lofty goal - but I have fallen short two years in a row.
2. I decided to try my first ultramarathon event in 2020 and competed in the Last Man Standing in Maine. Rules were as follows: run a 4.2 mile trail course in under an hour. Then, every hour on the hour, go again. Goal is to keep running until there is… you guessed it… a last man standing! In my first year I ran 6 loops. I came back in 2021 and improved - I ran 10 loops (which was the furthest I’d ever run!). Hoping to continue that progress, I came back yet again in 2022… and unfortunately regressed (only completed 8 loops). While running almost 35 miles is still good for me… I do not like the feeling of declining!
3. Midway through a keynote for a large, well known franchise brand… my mind went totally blank (first and only time this has happened!). I couldn’t for the life of me remember what I was supposed to say next?! What did I do? I just owned it, acknowledged the ‘elephant in the room’, and asked for the audience’s help to get me back on track (which they did with tremendous grace).
4. My first book (Raise Your Game), released in 2019, and sold pretty well. Not James Clear, Mark Manson, or Ryan Holiday well - but very respectable for an un-famous first time author. My second book (Sustain Your Game), released in 2022, did not sell so well. While I actually believe it is a better book - it only sold a fraction of my first book. In fact, RYG still outsells SYG five to one! Why? I don’t think the word ‘sustain’ is attractive. People want to elevate, raise, and optimize… not sustain. This is 100% on me as I fought hard for that title! NOTE: the word ‘sustain’ is 100% accurate to the book’s message - it’s just not an alluring word!
5. As a lifelong standup comedy fan and student… I decided to give it a try at a dozen open mic nights in comedy clubs around the DC area. My goodness was it hard (and I’m a fairly decent professional speaker with what I’d like to believe is a solid sense of humor!)! It is a very specific craft and one I have unparalleled admiration for (but have let go of my dream of having a Netflix special!).
6. I consider myself street smart, have high intuition, and an abundance of common sense and I fell for an online scam that resulted in me giving up control of my business FB page to a hacker (and lost 60K+ followers).
7. After two years, my girlfriend and I decided to end our romantic relationship and just be friends. She is absolutely one of the most remarkable women I’ve ever met… and I still care about her deeply… but a variety of circumstances ultimately proved too much for us to handle. I will always cherish our time together and the experiences we had… but it did come to an end. And thus, at almost 50 years old, I’m back to being single… so please cue Whitesnake’s ‘Here I go again…’

There you have it folks… an inside look at some of the bumps, bruises, and failures I’ve incurred in the last 36 months.

I encourage you to share this post with anyone you know who has recently struggled with failure (to let them know they are not alone)… and I challenge you to share a failure of your own in the comments!