A Look Back at 50

Today I turn 60 and on this day I am feeling so grateful for the life I am blessed to live, the family and friends that support me, and for the things I’ve learned along the way. I am not a fan of age. I tend to have this aversion to being stereotyped by age. “It’s only a number, right?” But as I look back at my last decade, I can’t help but evaluate my experiences and what I learned from them over the last 10-years.

I would boil it down to the following things:

• Optionality - I wasn’t a good listener what I was younger. The wise people in my life talked about saving a portion of each pay check, compounding interest, save now spend later. Well that’s boring. But in all seriousness it never really hit me until I started really understanding this idea of optionality and making decisions that provide you with the most options should things not work out. The book Antifragile by Nassim Nicholas Taleb describes the concept of gaining when events don’t go your way. Things like debt and paycheck dependence leave you with few options or “fragile”. In 2015, I found myself in this situation. Most of our friends couldn’t understand why we would sell our beautiful home on the river in Stuart. I had just sold my company and was building something new with the buyer. But when events outside of your control effect you, debt and paycheck dependence leave you in a fragile position. Over the past eight years, we worked hard to become debt free and we enjoy every day in our wonderful Sewall’s Point home. Not owing anyone (including a bank or mortgage company) a dime is a gratifying feeling and it creates optionality.
• Lifelong Learning - I tend to make changes in the face of significant events. Looking back, these decisions don’t always work out for the better. On 9/11, I was on a flight from West Palm Beach to LaGuardia. Back in those days, the planes had air phones and chatter was beginning to emerge about a terror attack in NYC. Around that time the pilot came on the intercom and notified everyone that the flight was being diverted to Atlanta due to a terrorist attack in NYC. Our son Brandon was only 11-months old at that time and I was spending more time on airplanes than I was with him and Nancy. It was at this point that I decided to purchase a software company “close” to home so I could spend more time (nights) with my family. Thus began my 17-year stint with DockMaster. After DockMaster had sold for the second time, the thrill of going to work was starting to wain. Steve Jobs he look in the mirror each morning and ask himself if he looked forward to the work he planned to do that day. If the answer was “No” too many times, then it was time to find something different. In comes COVID in Mar 2020. I had been with DockMaster in various capacities for 17-years. I wasn’t excited about what I was doing anymore, so it was time to do something completely different. I joined DMG as their CTO and I haven’t looked back since. But the transition from vertical market software to disaster management and emergency response was a big change and it required me to think about what I put in my head. Going back to school the traditional way was not an option and it was around this time that I began to do a deep dive into online learning. I took several AI courses and learned a lot about machine learning on small devices (think Alexa). Since then, I’ve been diving into all sorts of subjects like modular housing and construction, biographies of US historical figures, and meditation. I will always be a student, open to learn new things.
• Memories not Stuff - In my 40s and into my 50s, I was convinced that the road to happiness was to make as much money as possible and gather up as many things that the money would buy. Vacation homes, boats, different vehicles for different occasions. All must haves. What I found was besides the fact that having all of these things and finding ways to pay for them leaves you with few options (see “Optionality”). It’s also not very gratifying. The more things I collected, the less happy I became. What I really enjoyed was traveling and the memories that I collected during some of the amazing trips we’ve taken like going to Bali, South Korea, Hong Kong, Germany, Italy, Spain, France, St Barts, the BVIs, the Bahamas, etc., etc. But living from vacation to vacation isn’t a life worth living either. As I got older I began to realize that it’s about the journey not the goal or destination. Living in the moment, not in the past or the future began to open up a whole new reality for me. I began to take in the experiences of what people consider the more mundane, waking up next to the love of your life, smelling the coffee brewing in the morning, being able to walk outside in the morning and hear the bird chirping. May sound cheesy, but its these simpler things that I began to realize is what make each step of the journey invigorating. Each step isn’t pleasant, people cut you off in traffic, you don’t get the deal you’ve worked so hard to secure, or you throw your back out trying to stay fit. Welcome to living. But I began to realize that the true blessing of life is the connections you make with people and the experiences in each and every day,
• Habits not Goals - I used to make a big deal of setting goals. I had the annual goal setting review (that got pushed off sometimes until February), then I had quarterly goals, weekly goals, personal and business KPIs, etc. While these are all very valuable, I learned that what’s more important is developing habits that can provide you with more optionality. One of the key ones for me is working out. I used to dread working out. It was a chore like so many other things in life. But I knew it was the right thing to do on a steady basis if I wanted to continue my quest of life long learning and gathering lasting memories. I went from being the person that forced myself to workout when I had time to someone who works out every weekday morning as a habit. If I miss several workouts like I did this past weekend in Costa Rica, I began to feel a bit lost. I have developed a habit of working out just 30 to 45-minutes each weekday morning. It is simply part of who I am now and I think it does more for me mentally than physically. Shane Parrish, podcaster and author of Clear Thinking, writes that “goals have an endpoint” and require “constant evaluation”. Once achieved you need to find a new goal. Habits on the other hand are automatic, you set them and forget them. I just happen to be someone who works out each morning for 30-mintes. It’s part of who I am and I schedule meetings around this block of time if I am able.
• My Morning Ritual - Working out and the value I get from living in the present are reinforced through my morning ritual. Look, I am old. I went from being a burn the midnight oil guy to a morning guy. I love my mornings. It’s when I have the most energy both physically and mentally. So, one of my most sacred habits is my morning ritual. I wake up usually before anyone else, and I go to our sitting room overlooking the pool, oak tree and back yard. I start by meditating for 10-15 minutes, followed by my morning prayers, then three sun salutation yoga stretches to get the blood flowing, followed by my morning coffee. (This is the only time I drink coffee usually). I won’t check any email or look at news or social media on my phone until I’ve done these things. (I’ve pretty much removed most social media from my daily life). When I am done drinking my coffee, I go upstairs for one of my 30-45 minute Peloton workouts. I do this every morning, almost without exception. It is harder when I am traveling, so I tend to augment the schedule. A word about meditation. A lot of people tell me “I tried meditation but it didn’t work for me”. My usual response is everyone sucks at meditation. How are you at breathing? Is this something you know how to do? Great…stop, close your eyes, settle in to your chair and take a slow deep breath in through your nose, and slowly release your breath through your mouth. Do that 10 times…you are meditating. That’s where it starts. There are lots of wonderful meditation apps out there. I love Insight Timer.

For those of you that are still reading this, thank you. I am sure I’ve lost the majority people. I am so looking forward to my next decade. I was telling Nancy this weekend that I think my sixties will be my best decade ever. I look forward to seeing what new memories and learnings the next 10-years brings as I try to live each moment in the present, remembering to slow down, take a few deep breathes, and observe the world around me.