25 years ago this summer three buddies of mine made our way across Europe. We all graduated college and were doing the customary post-graduation Eurail European adventure. We started in Italy and worked counter clockwise across the European continent ending the trip in Spain. The stories are endless.

• We drove too fast in a promotional Hertz rental car that was all yellow and covered in logos. 
• We climbed the Swiss alps. 
• We consumed so much beer in Munich that I somehow was able to sing Lithuanian folk songs through the streets at 3am.
• We got wildly lost in the red light district of Amsterdam. 
• We recreated scenes from the Sound of Music in Vienna. 
• We drank sangria all night and ran with the bulls in Pamplona, Spain the next morning with no sleep. I’m pretty sure we slept on a street bench that night.  
• And the stories go on and on. 

When it was all done, I loaded up a U-Haul with two buddies and we drove from Connecticut to the center of technology, Silicon Valley.  Silicon Valley was where I needed to be.  I had a Computer Science degree in hand and dreams to change the world.  Fast forward to today — I’ve been driving technology products and teams for 25 years now and have been fortunate to take all sorts of awesome products to market in many different scenarios — start ups, venture backed, public companies, private equity backed, consumer, enterprise, education, government, financial.  From no name brands to big brands, I just worked my ass off and continue to work my ass off.  I like it that much. 

25 years of hard work hard work requires some reflection. As I’ve said in previous blog posts, sometimes this reflection is for me as much it is for anyone else. My blog posts are like public journal entries. Below are some higher level questions that I was reflecting upon —  

What have I learned? 

Here are is a list of axioms I’ve picked up along the way in no particular order.

• Play chess, not checkers.
• First principle thinking is paramount.
• Keep challenging your assumptions. 
• Get your team as close to the customer as possible.
• It’s all about the people and your teams.
• Micromanagement only gets you so far.
• Try to lead, not manage.
• Be genuine. 
• Be respectful. 
• Work hard. 
• Stay hungry.
• Listen more.  Talk less. 
• Setbacks are opportunities.
• Ego kills.
• Keep your standards high.  Don’t settle. 
• Stop the whining.   
• Have urgency but be patient. 
• Smile and laugh more.

What adjustments have I had to make after 25 years of working?

Experience can be a blessing and a curse.  Yes, there exists 25 years of experience to draw from but that doesn’t mean I know everything.  Ego can get in the way of learning new things.  “I’ve done this enough, I know what I’m doing” becomes the new slogan.  Its important to not get caught in that mindset. The reality is “I don’t know everything, I’ve not seen all situations.” Keep an open mind.

Additionally, the more experience you have the more career optionality you have which makes it too easy to bail out of one situation and into another rather than doing something differently.  I have to apply first principles thinking to myself in these scenarios.  I don’t always have all the answers.  My assumptions that I’ve held for years likely have changed.  Feedback is good. 

What is my perspective on the next 15 years of work? 

I think I’d like to take this train 15 more years. 40 years of work feels like a nice round number.  I’m happy with the success/exits under my best but I enjoy work too much to retire. If I keep picking them right, there probably feels like two more big rides.  That seems reasonable.  Currently, the technology future excites. We are pushing into another huge technology wave with artificial intelligence (AI).  AI is every geeks dream. Frankenstein. Hal.  Rosie. Jarvis. Roy Batty. Wall-E. R2D2. C3PO  We’ve been day dreaming of a world with AI beings for years.  We are  going to see an another profound technology shift over the next 5-15+ years and its going to go faster than we think.

What would I be looking for if I were evaluating new opportunities?

My work motivators in my twenties are surely different than my motivators in my fourties. As a kid, I wanted to be featured in a TechCrunch blog post and bags of money. I wanted to prove to my parents that I could make it as a technologist and not a medical doctor. Time passes by and I am looking for different things. I am definitely less motivated by money.

Now, I care deeply about …

• the people I work with.
• the impact I can make.
• the opportunity being big and bold.

What would you tell yourself from 1999? 

• Keep building. 
• Take more risks.  
• Stop listening to other people.
• Stop overthinking things.
• Find the road less traveled.
• Make time for your friends and family. 

I like to say “trust the universe”.  Things seem to work out. I’m grateful for my career path and all the wonderful people I’ve been able to work with along the way.  I’m not sure I would have done it any other way.  Here’s to another 15 years of building innovative products!  

Thank you for reading.  I appreciate you. 

-rjm