40 Years Old :)


Goodbye to my 30s and hello to my 40s :)

I am very glad to have made it this far.

And, here I am… turning 40 in a small town outside of Porto in Northern Portugal. It is amazing where life takes you!

This week I’ve been thinking about my 30s and what I want from my 40s.

My 30s…

I moved to DC at the end of 2010 when I was 29. I had been living in Denver and needed a change. Denver just didn’t feel like it was the place for me. I wanted to travel more and have some adventures while I was young and unattached. For my 30th birthday I was living in Washington DC and I had a chill night with Iris. We grilled some steaks on the porch, drank some really peaty scotch (thank you Chappy for that introduction), and talked all night. It was a great birthday!

Site5 was doing well by this point and we had owned it for a little over 2 years. We had cleaned out a lot of the financial/technical baggage and the previous year we had finally seen the results of all that work. And, I was feeling a bit more confident in my ability to run and grow the business. Not to say there were no bumps… but I had a better idea of what I was doing.

By the time of my 30th birthday, I knew I was going to spend 2012 and 2013 traveling and had some rough plans. I knew I was going to start in Central America and then move down to South America over the first 6 months of 2012. Then, I was going to meet my brother in Australia and live with him for a year. Beyond that, I didn’t have much figured out. The two years I traveled were some of the most amazing experiences of my life. I had so much fun with Rose and Steve as we crossed paths throughout Central and South America, with Joel and Laura in Chile (wonderful introduction to Havana Club), and living with my brother in Melbourne (my “life coach”). I celebrated my 31st birthday with my brother in Melbourne and my 32nd birthday on a boat off the waters of Croatia. My mental state was in such a great place by the end of those two years. I was a calmer and more confident person for many reasons. 

In October 2013 I flew back to Fayetteville for a quick 3-day trip to surprise Joel, Iris, and the Fayetteville crew (big ultimate tournament). I went to dinner with Lindsey that Friday and everything just clicked and I had this amazing feeling that I was going to marry her. After I left I wrote to her often and she visited me in Scotland a few months later.  We started dating when I got back to Fayetteville in late December, we got engaged in October of 2014, and we were married that December 😀. Not to imply that was an easy year, as 2014 was the hardest year of my life for a number of reasons (much longer story there mixed between work and health).

What is amazing to think about is that from 33 onward I’ve shared my life with Lindsey, from 34 onward we’ve been married, and from 35 onward Calico has been part of our little party. A lot of great adventures and hopefully many more to come :).


Looking back, what strikes me about my 30s?

  1. There were massive changes with whom I spent time. My 20s were primarily spent with close friends and the ultimate community. But the majority of my 30s were spent with Lindsey and Calico. In my early 30s, some of my closest friendships faded away or were abruptly dropped. That was painful. I thought that was due to me and specifics in my life, but I watched my wife go through similar. I wonder if that is common and if there is a big shakeup as people settle down, get busier, and choose where they spend their limited time and energy.
  2. I lost a ton of anxiety/fear and gained a ton of courage/confidence about who I wanted to be in this world. I credit that to a lot of solo travel, a lot of time alone to think, ayahuasca, and an intense job I had to grow into. The difference between me in my 20s and me by my early 30s is insane.
  3. This might be a weird one… but over my 30s I gained such a better “understanding” of humans, and this helped me feel confident in interacting with them as my “full self”. This is a big change over my 20s when interacting with people was just confusing and frustrating and I was a much quieter person. In my early 30s, I attributed a lot of this to my job. I was interacting with a large and diverse group of people across the world and I learned so much from them. But, being married has taken that “understanding” from a kindergarten level to what feels like a Ph.D. That doesn’t mean I *really* understand humans better, as they continue to astound me, but in general, I understand motivations for why they say and do things better. This “understanding” has helped me become a calmer and more patient person… and weirdly… a bit more uncaring about people but in a positive way. Not sure if it makes sense but it is a big change over my 20s.
  4. I have a much better handle on how to keep my body and energy levels healthy. They should make physical rehab and training a mandatory part of junior high and high school along with financial education (and practical real-world ethics, morality, and philosophy).


What do I want from my 40s?

  • I want to work on a fun project that challenges me, uses my creativity, and helps people.
  • I want to spend quality time with my family and not live an overly stressful life.
  • I want to have a lot of fun adventures (solo and with Calico/Lindsey)
  • I want to stay in good health, great physical shape, and maintain healthy levels of stress/energy.

I’ve got a long list of how that translates and I am looking forward to it :)


posted under My Thoughts | Comments Off on 40 Years Old :)

This kinda made my day :)


Peter Grose is an amazing author and he has created two awesome lists for Shepherd:

He wrote up a really nice blog post about Shepherd and me. It really made my day as it capture a big part of why I started the website and what I hope it can help impact. I am hopeful that I can play some small role in restoring America, as it has lost its way and no longer represents the values I was raised to believe in.

I am a very optimistic person and it takes a lot to phase me. But, I had a terrible day this month when an author was incredibly abusive. It was a very weird experience and they were obviously dealing with something that caused them to react in such a way. I ended up having to cut them off and it was a bad day. I am always grateful for people like Peter and the 99.999% of authors who are supportive, kind, and respectful.

posted under Books | Comments Off on This kinda made my day :)

This is bwb’s personal blog, so he can share his thoughts with the world, however scary or silly they might be. Plus family and friends can track what I am up to, and where I am in the world.

I am pretty simple. I love Mangos. I love the ocean (although mostly at sunset, as I’m a ginger). I love to travel, eat exotic food, do long bike rides, read, and use my imagination. At some point, I decided it was better to be a pirate captain than an admiral. I am a globalist and see the entire world as my responsibility and playground. And I am married to an amazing woman who makes life even more fun :)! And we are now the proud parents of Calico Jack :).