Leaving the Full-Time World

May 17, 2024

If my plan holds, yesterday was my last day of full-time employment. I'm excited and terrified.


The Plan

This has been my plan since the beginning. Work has always been a means to an end for me, funding my ability to provide for my family and to fund my hobbies - "work to live" rather than "live to work". Well, it's not exactly that cut-and-dry, since the routine of going to work every weekday for 25+ years demands shaping one's life around a job. But in the end, I have always looked forward to eliminating the compromise of selling a third of my waking hours to fund the rest of life.

During an intentional work-break after leaving Splunk in 2021, I did an exercise to calculate how much money I would need to have saved to retire and to project how much time I would need to get there given my current cash flow. That exercise led me to decide I would work until 2027, which was a combination of having enough money to never have to think about it again and having Naomi settled in college.

How It Unfolded

I started working for Stripe in 2021, which was an amazing experience until I was laid off about 6 months after I started. The emotional roller coaster really helped me to further develop my view of one's relationship to their employer being a business relationship and no more than that. Leadership in a company can decide at any time to let employees go for basically any reason, and so the employee's relationship with their employer should reflect that as well.

I took another 3-month sabbatical after getting let go from Stripe to regroup and hunker down to find another good job. I found a great opportunity to work again with some good friends at NGINX (actually F5, but it will always be NGINX to me) in a dream role. It wasn't the best paying option I had at the time, but the domain, role, and work-life balance were really appealing. I started that job in February 2023, expecting to put in several years, then hopefully retire as planned.

Over the holiday break at the end of 2023, I looked again at my retirement model, perhaps with a different attitude. I was really enjoying my role at work and the wonderful people I was working with, and I was playing an important role in the top priority project in NGINX, but the corporate environment we're in with profit above all was leaving me feeling empty and conflicted.

So I ran the numbers again, and saw that I was actually in a better position than I thought I was in terms of being able to survive, sans job. Success probability (with success declined as not needing to work full-time again) was about 60%, given the expected, pessimistic, and optimistic models I was using. Once I saw that if I could just bring in a couple thousand dollars a month, that success probability went to 100%. At that point I was convinced that it was now time to make my move. No turning back!

Excited For

What motivated me to leave a relatively secure, low-demand, high paying job was everything outside of that job. I'm looking forward to being able to be more present for Naomi as she's entering her last two years of high school. I'm excited to visit my family more, which I've been putting on the back burner for several years now. I have endless energy for hobbies and projects, and this would show up as a feast and famine time allocation -- hobbies would get to feast on all my free time, to the detriment of traveling to visit family or spending time with friends. With my work schedule, oftentimes my physical fitness would take a back seat to everything else.

I'm excited to be able to find a new balance between hobbies, friends, family, and fitness. The idea of waking up and having the entire day ahead wide open for me to decide what I'm going to do in each hour is very appealing.

Scared About

The easy answer here is "money". My money is not under my mattress, but rather in my house and other investments, so it's subject to market movements that are not in my control. This gives me anxiety, but if we obsessed over every unpredictability in life, we would do nothing. I know I will have to scale back on my lifestyle to make this work, but to me the emotional benefits far outweigh the loss of ability to just buy whatever I wanted whenever I wanted. Thankfully I'm not the kind of person who needs designer clothes or expensive cars to feel good.

I feel as if I'm standing on the precipice of a personal reinvention, which I'm mostly excited about but also a little unsure of just how things will work in practice. Will I achieve new personal highs of connection and health? Or will I turn into a craggy hermit, overeating and miserable? We shall see!

A Dose of Guilt

Few people have the opportunity to do what I am doing. I am lucky to have been born when I was, with a set of abilities that just happened to match where a huge new industry was headed. I'm lucky to have the opportunities that were put in front of me, and lucky that I grew up in the family I grew up in. As I say goodbye (for now) to wonderful colleagues, talking with friends, or just thinking about people in general, I feel guilty. I don't think I've worked harder than other people. I know I have just been exceptionally lucky to be me in this world.

This feels inequitable to me. I'm not sure if there's a feasible alternative given how this world has evolved to work. I'd love for people to embrace each other more and let go of the lust for profit and wealth more. I know that would mean that I would likely be working now, but I think the world would be a much better place. I hope I can be a force for good in my community to pay back this debt.

A Heap of Gratitude

Building on feeling lucky, I have been so fortunate to have been supported by so many people from early on. It starts with my parents who realized when I was a young boy that they had a real nerd on their hands. I would take anything apart to see how it worked. Lucky me that their reaction to this wasn't to punish me for this but to stoke the fire by buying a computer for me to use. That VIC-20 in 1982 was magical and led to a lifelong relationship with computers, technology, and programming. My dad would bring me to his office on weekends sometimes so I could play with the fancier computers there (IBM PC, Apple ///).

I'm thankful for my lifelong friend Derek and his parents for being instrumental in helping me break into working with computers, first as a Service Technician at Fry's Electronics in high school (Derek's dad was a manager there), then at Yahoo! after college (Derek was a very early employee and convinced me to interview there), and then we later started a company together (Dipity).

Thanks to my dear friend Mona for also being a force to help bring me into Yahoo!, then as a really special friend that took me on wonderful adventures (Coachella, Egypt, DJs Silky and Pants, ...). I would not have become the person I am without Mona's influence.

Thanks to Judy Swanson at the Cal Poly Library for letting me be the best nerd I could be, building web applications for the school, which set me up for an amazing career. Thanks to JohnR who saw my potential as an engineer in my interview at Yahoo! and steered me in that direction, to Kevin Athey who was an endlessly patient and generous mentor for me from the beginning, to Mammad Zadeh and Arturo Behar (both friends/managers in different teams) who taught me so much about programming and life. To Mark Johnson who got me in the door at Groupon and trusted me to run with some pretty big stuff, and to Kyle Oppenheim for giving me some absolutely amazing opportunities to grow. To AJ for being a great friend and partner in some crown-jewel projects, and to Jeff Weinstein for just being an amazing human being and helping to get me in the door at Stripe and teaching me so much about how to build great products.

Shoutout to Ben Garrett (bag) for being a great friend and mentor and for believing in the Dipity dream with us. :)

Big big thanks to Eric Douglas for being a great friend who also joined Dipity, then brought me into three different companies where he managed teams where I learned and grew tremendously each time.

Thanks to Amanda Grovom who played a pivotal role in my own post-divorce personal reinvention. Her friendship was a lovely gift that helped me to feel confidence in myself, and she was the person who convinced me to get back into music-making. That has become such an important part of my life, I can't thank Amanda enough.

There are hundreds of other people I could put in here too. Each moment feels like it led me here, either through outright guidance and support or through moments of learning and discovery that helped me to make good future decisions.

So What Now?

We'll see! I know I will continue, at least for now, doing personal programming projects and making music and other art. I'm excited to spend time with family and friends that I'd like to see a lot more often. I'm excited to find areas of my communities where I can contribute -- like helping to maintain trails, teaching computers or business survival, and going all-in on building great free tools for other electronic musicians.

I have a particular interest in and ideas for how product development works in software teams, and have started writing about this. My hope is to educate people in the industry that it's possible to have both a happy and increasingly capable team and outstanding productivity and customer satisfaction. I think this could positively affect many peoples' lives, and can possibly be a future income vehicle through consulting engagements with businesses who want a hand putting these ideas into practice.

But right now, I'm just trying to understand that this is actually happening...