The words "This Might Work" over a background showing windmills

This Might Work

As I kick off my writing for the umpteenth time, I realize it has been almost six years to the day since I last wrote about starting over. It feels like a lifetime, as well as a lifelong theme. If you pore over my about page, you’ll get a hint of how many times I’ve started over:

  • When I ran out of support for fancy engineering school, I had to go back home to Puerto Rico and start again.
  • When I completed prerequisites for University of Puerto Rico, started again there.
  • Then I ran out of money. Start again, somehow.
  • So I borrowed money, bough a computer, and learned digital design. Started a “desktop graphics” hustle.
  • Somewhere along the line, I started a sign business.
  • When economic calamity set in in Puerto Rico, we sold everything and moved to US mainland to, yes, start again.
  • Florida didn’t do it for us, so we moved to Austin, Texas to start again.
  • When I’d had enough of the sign industry, I started again at a nice design studio.
  • The ’08 recession caught up with me in January 2010. Lost my job to an industry-wide collapse.
  • So I started again, freelancing.
  • Then, in 2012 I started a digital marketing agency, and worked like crazy to grow it to a $250k of recurring revenue.

That last time I wrote about starting over was the end of that business partnership due to the ol’ “business partners incompatibility” with a little burnout. Little did I know how many more times I’d start over after that:

  • Launched a new business, after a while…
  • Launched a new model, after some success…
  • Took some contract work as Technical Project Manager with a web development agency.
  • After some time doing that, decided to shut down my business and go all-in on the Tech PM job, but…
  • The pandemic changed the business. Not content with the new direction and relative under-employment, I started a search for a job.
  • Landed a job in the Product Information Management space. Great software product, not a great match for me. But in my time there I met some people from the company where I work now, and thought about how much I would like to work with them.
  • Started job search, and before I had anything secured I decided to focus on my mental health and better prepare for my job search and interviews, so I “jumped without a parachute”
  • Landed the job.

So here we are, a career many moons in the making and a twisted path to get here. Through it all, I realize one thing has remained constant: Every time I tried something, I had to believe that it was going to work. At the very least, I had to think “this might work”. It would have been stupid to try anything that I didn’t believe could work. Turns out that whether it was by sheer necessity, or subconscious conviction, I had more faith in what I could do than I would consciously recognize.

Seth Godin has talked about how a lot of what we do are projects, experiments, explorations, and that “the task is to leap forward, to improve, to explore the next frontier.”

May you find yourself thinking “this might work”,