Tuesday, October 15, 2019

A Whole Bunch of Self Reflection

It's been a very challenging year, yet also a very rewarding one. Part of the genesis of this blog has been the self-reflecting that I've done with a pile of milestones in the past year.

  • Turned 50. Unlike any other "milestone" birthday, I actually cared about this one. Probably the cumulative effect of the other factors on this list, of course. Also, as a side note, I skied on both the final day of my 40's and the first of my 50's. This is particularly notable since my birthday fell on Memorial Day weekend this year!
Arapahoe Basin on Memorial Day 2019. 
  • My wife Kate also turned 50 this year. Technically, it was in 2018, but in this same general window. We were 25 when we started dating. Half our lives together!
Turns out, this is the only photo we took on her birthday.
  • Had our daughter graduate high school and move out for college. We had nearly 18 years to prepare for this, but it still seemed like a shock. At the age of 50.
  • Top Pic is graduation from High School (May 2019). Bottom is moving into College (August 2019)
  • Punted on my last company and started a consulting business. There are many ways to look at this, but frankly, I've learned (sometimes the hard way) that failing at business is as important as succeeding. More on that in a future post. The relevancy to the self-reflection motif is that I was back to a career reinvention. At 50. With a kid moving out to college. 
A biz friend refers to me as the "Get Shit Done" guy. So I built a brand around it.
  • My son was struggling in traditional public high school. Super intelligent kid who just was not interested in school. We were pulling our hair out trying to figure out what to do with him. We were able to enroll him in an experience-based school (part of our county's public school system), but we did not know he had a spot until a week before school started. He's doing amazing and is back to the engaging, energetic, bright young man we had lost for a while. All that while dealing with a career reboot, a daughter moving out, and turning 50. 
Maddox upon his return from the mountains. Backcountry backpacking trip that is required to graduate!

Okay, so maybe this isn't a massive pile of events, but for the first time in my life, I was even aware of a "big" birthday. And don't get me wrong, I'm not whining about turning 50 nor was it particularly painful. I just got to be self-reflective in this past year or so, which is really unusual. 

I looked at colleagues and their careers, tinted by the lens of my experience. Should I have taken a more traditional career path? Would some of our struggles have been avoided? Or would they be replaced by different ones? 

One friend of mine was a 20+ year veteran at Sony. He had one of those really fancy titles: Senior Executive Super Duper Vice President or something like that. Then one day, "We're going in a different direction." Boom. Out. Was that route any "safer" than the one I took? 

All of those factors provided the fuel for this series. What if I'm not the entrepreneur that I've thought I've been all these years? Am I just painted into a corner where that's the only thing I can do? 

I actually tried to morph into a "traditional" career about eight years ago. I had "sold" a business at the time (I use the quotes since it was really an Acqui-Hire--my company was breaking even so I effectively traded it for a job) and moved with the family from our Maryland home to San Diego. When I got to Mad Catz (makers of video game accessories--my company was in the business of licensed t-shirts, mostly based on video games), they had no idea what to do with me. Literally and metaphorically. I showed up after driving cross country and the office staff had no idea who I was or what I was doing there. I didn't even have a desk. (SIDE NOTE: I think I'll tell the long-form version of this in a future post) After seven months, I was laid off. The only job job that I had held in 17 years and it was gone. 

The point of that little interjection is that I actually did try to go back into traditional employment. Image result for there is no try Talk about discouraging. My "resume" looked like this: Founder (12+ years), Founder (5+ years), VP Merchandise (7 months). I couldn't even get recruiters to return my calls. AND, this was in Southern California. On paper, I'm unemployable but in reality, I'm one of the best team players I know. 

So am I forced into entrepreneurial life? Am I destined to be in this? Are there others who feel similarly? Turning 50 or not, that is the basis for this exploration. 


  1. Great stuff, Mike. Turning 50 ain't that big a deal really, I can say from experience. I think, interestingly, careers are launching pads more than resting places, or at least that is how it has worked for me. I spent most of my adulthood in various marketing positions, and I had a great time doing it, but looking back I see those years as preparation for something more...maybe less stable and lucrative but more exciting, adventurous and obviously rewarding. Wouldn't have been ready, I guess, in my twenties or thirties to take those kinds of risks...you know the kind where you are just really OUT THERE, but in time I was...and I'm glad. May your 50's rocket you in to places unforeseen and unexplored.

    1. I really like your phrasing: "Launching Pads versus Resting Places." Might have to borrow that one.

      I can only speak from my own experience and I started out at the ripe age of 25. This exploration has been enjoyable so far, though. Thanks for reading (and commenting)!

  2. A hundred thoughts about this. I’ve turned 50, I’ve wrestled with questions aplenty re: W2 v 1099, re-inventions of self, destiny, capability and on and on. Rather than word-bomb your space I’ll bounce them around in my brain awhile and here I’ll simply say I’m stoked to see this blog take shape, it’s been awesome to read some of your recollections and insights.

    1. It's meant to be a dialog of sorts. It will only resonate if others have had the same struggles/challenges/wins. I still have no roadmap for this journey--just going out on the road with it.