The first days of the rest of my life

5 min readJan 21, 2024

Last friday, I retired after nearly 30 years of working in tech. But I’m still not sure what that really means, aside from opting out of steady paychecks.

There’s a lot going on in my head as I try to relax into this situation (but, without getting lazy). I will summarize the thoughts at the top of this pile in my favorite format, a bullet list, and then explore a bit more in depth below. I’m writing this as much for me to help me figure it out as for you to understand it, but hopefully it’ll resonate with you and inspire you in some way, too.

  • I am on a bit of a soul searching journey since I read The Pathless Path, which has led to me questioning all of my assumptions about what I want to be when I grow up, what matters to me, and how I want to live my life.
  • I enjoyed working — particularly, being engaged in projects and communities — so I don’t want to stop “doing things”.
  • I have already planned most of a bicycle touring trip which will lead me across the North American continent over the next year.
  • I intend to write a lot over the next year, largely in service of the above missions!

I have been pouring my heart into my work for the past 7.5 years, and this work has paid very well, so I think I am in a place financially where I will not need to collect a paycheck. The conditions to maintain this life are that I’ll need to live reasonably modestly for the rest of my life, and that the stock market doesn’t completely deflate, along with avoiding other major tragedies. This does mean not buying a new $10k bicycle every year, nor collecting sports cars, but it doesn’t mean no adventures or vacations! Plus, I already bought two very expensive bikes in the past 2 years so maybe I’m set for awhile on that front.

With all of my heart/energy spent at the office for so long, I’ve been shortchanging my relationship with my partner and friends, but also fallen behind working on myself — physically and mentally. I also built up a pretty large to do list from cleaning out the attic to reading a̶ ̶f̶e̶w̶ many dozen books, trying a bunch of recipes that I’ve been saving off in various browser tabs and just spending more time doing things that matter, which aren’t “a job”. When I was hard at work on some else’s mission all day every day, those other things were deprioritized since I was often worn out by the end of the workday. I’m looking forward to having energy to put into my own missions now!

Will I miss the incredible team I worked with? Very, very much! In fact, I’m pretty likely to be somewhat lonely since I am no longer getting paid to talk with my friends for 8 hours a day; I was very privileged to work almost entirely with people I would consider friends or at a minimum kind folks I enjoyed chatting with and with whom I felt a mutual respect for. But, I am excited to not be focusing, as all of big tech does, on shareholder value even if there were other more inspiring components to the mission like improving the web or helping people use technology to improve their workflows and lives.

The Pathless Path is a book about choosing not to do the default things that society suggests we should resign ourselves to: working until we’re old at a 9–5 job, stopping work when we retire, having 2.5 kids and owning a home with a white picket fence by the time we are thirty, and so forth. It suggests reframing our life activities based on what matters to us, which of course we get to pick! Family over money, health over fame, mission over career progression. But, with all of the energy I’ve been putting into work, I’m not even sure what matters most to me these days, nor what I want to be when I grow up. That book has inspired me to ask more questions about the status quo and be bolder in trying new things, like not working, and I cannot recommend it enough if you are feeling a bit disconnected from your life!

That said, I am keeping an open mind so when my friend Emily Schario suggested that perhaps I could give workshops on building customer support teams to incubators like the one she works with along my journey, that resonated and sounded interesting and I’ve begun working on an outline for such a presentation…or maybe a book about the things I’ve learned in doing this work? Let’s see what happens! I don’t need to sit on the couch for the rest of my life; I could have fun presenting my vision to people who care as a part of my new life. I could have done this in the past of course, but I did not have energy for major side projects while I was working so hard at a full-time job I cared so much about.

Serendipitous opportunities aside, I’m embarking on a soul-searching adventure to figure out what matters, and hoping to write a lot along the way. I already know that writing — and being able to revisit experiences based on what I wrote — is very important to me! So this year I’ll take a bike trip — my favoritate meditative activity — to let my brain rattle around in my head, and look to shake the sieve of my jumbled thoughts to extract the nuggets of joy and discard the grains of annoyance by writing daily. I’ll also get to ride my midlife-crisis-mobile the way it was meant to be used, on a journey of thousands of miles through places I’ve never seen before while I ponder.

a picture of my new custom touring bicycle
the steed

I’ll write about that trip on a different website ( which I’ll be getting into shape over the next few weeks before I depart mid-march, and see what I can find in the world. Come along with me and I’ll try to share some interesting and fun moments via (mostly) text, image, and video.

Happy trails to us!




I’m just a guy who likes stuff, like riding bikes, facilitating joy, building community & the culture of customer support,