I'm #Retiring

Taking a necessary "leap" to see what's on the other side

Well... I’ll just come right out and say it—I’m retiring.

Retirement letters always include a nod to spending more time with family and pursuing other interests, and mine is no different in that regard. But instead, I’d like to use my parting words to give voice to some more personal thoughts, hoping they may be useful to those trying to wrap their minds around this career bookend.

Fun fact: I’ve never left a job, nor have I ever been fired. My entire working life (aside from summer jobs as a student that naturally ended at the end of summer), has been spent with one company or another that got acquired, with me coming along for the ride. I was hired out of university by Mountain Lake Software in 1997, acquired by Immersant in 1998, which shuttered its operations in 2001. Drew, Glenn, and I started Jonah Group from the detritus of that project in the same year, and were acquired by 3Pillar 21 years later in 2022, where I’ve worked ever since. To say I ignored the advice of “job-hop to get ahead” is a major understatement. And frankly I don’t think I missed much. My counterproposal would be “find problems where you sit, and stick out your neck and try to fix them.” It takes a while to build the trust required for someone to give you the length of rope required to do that.

It was really hard for me to cross the chasm of this decision. I’d been oscillating back and forth for many years, in fact. I’m not one to be focused on romantic “one life to live” bucket lists and achievements, but it has become abundantly clear to me that it’s just not possible to fully enter the flow of life without making decisions that leave one path behind in favour of another, though I’ve tried. Ok that seems obvious now that I’ve written it, but yeah... it turns out you actually do have to give things up in order to get other things, which means being clear to yourself about your values and priorities is pretty important. Buffett’s 5/25 rule, and indeed his entire investment philosophy, is emblematic of this. And knowing your values is different from enacting them, which can be scary.

All the big decisions are like this. Buying my first home felt like hurtling myself off a cliff. Selling Jonah Group felt at once like an exciting step, and like someone ripping both of my arms off (Jax’s Mortal Kombat II finishing move). And retirement... well; in addition to the wonderful prospect of creative pursuits, in a dark moment it can seem like a voluntary acceleration toward personal obsolescence. We all dream of reducing stress and going about our lives at a more leisurely pace, but have you ever noticed how society doesn’t have any “requirements” of you during your “retirement” years? Another way of understanding this is that people really just won’t care what you do anymore! This is at once a welcome idea and a sobering realization.

Of course there are the financial considerations, but on this score I’ll bet that most people have next to no idea of “what is enough,” nor have they considered how they might adapt their lifestyles to match their defined retirement means. “Assuming I don’t have enough” or “not planning for what I think might be enough” may be a cover for “I find this change too hard to think about.”

Indeed, some have no idea of how they would fill their time, having dug a decades-long groove of grabbing the briefcase / backpack and heading to the office, even if virtually. Some wait until they have a health scare to take the plunge, but then instantly regret waiting, their retirement now looking like it’ll be an extended doctor visit. No one can tell you when the right time is, but everyone knows what “too late” is.

Anyway, thinking that you can optimize your way out of the cons leads to shallow engagement in life, as well as crushing indecision whenever you arrive at that important fork in the road that requires that you choose one good thing over another. And the more you notice your own mortality, the more soul-destroying indecision is. At a point in time, you just have to take a leap to see what’s on the other side.

Being an entrepreneur whose company lasted for a good long period has allowed me to mostly skirt society’s sometimes judgmental glare: we generally bless “success” in the work realm, even if it’s defined too narrowly. But in truth, my career has never been guided by the prospect of mounting some invisible ladder, achieving some specific goal, or collecting personal approvals (though I’ve struggled a bit with that last one). I didn’t set out to be a “successful entrepreneur,” and I’m certainly not a legacy guy. And I was never able to identify and pursue “work passions” as they always insist you should. In fact, I’ve struggled to comprehend most of the career advice I’ve received in my lifetime, and have come to understand that, at least for me, curiosity is the brightest beacon. I honestly believe you can do any kind of work and be happy — what matters most is the human context: the shared purpose you invent, assign, and pursue together with your workmates, especially those who ponder the same problems you do.

So I’d be skeptical of any activity you do solely to “advance” or “be successful.” The right path (at work and elsewhere) is the one that piques your curiosity and allows you to speak your truth. And if the people you’re talking to find that valuable, then it’s probably a good place to work. A consistent willingness to be open and truthful has delivered many a boon for me. And it’s likely largely responsible for the depth of relationships I’ve been able to foster in the pursuit. Highly recommended.

By far, my work relationships and community are the things I’ll miss most; trite but absolutely true. Shared purpose and struggle leads to strong relationships, which in my view is the best part of work — it’s one of the ways we share who we are with others. Life is just a process of getting some notion of ourselves into the heads of others, so that we can “be seen.” The resulting human contact and understanding creates lasting bonds; you take up residence in each others’ minds, and you feel your world expand.

Jonah Day (our annual company picnic), circa 2015

Some brief words on “imposter syndrome,” since many I’ve known have confided in me about it over the years. In my experience, everybody has it. It’s only natural when you surround yourself with smart people that you feel like an absolute clod sometimes. But would you prefer the alternative? :)

Your perspectives, capabilities, and efforts are definitely valuable, and do help your colleagues and your company in a multitude of ways to get where they’re trying to go. Even if you can’t always see it, or you don’t always express yourself the way you’d like, or they don’t always respond the way you’d like, or they seem much more capable than you.

And people like it when you don’t always have all the answers; it makes you seem human. Everyone’s just out here faking it ‘til they make it, ignoring the irony that there’s no such thing as “making it” — there’s always more to learn and do. So give yourself a break, keep learning, and help yourself and others to improve by letting those thoughts, questions, and opinions fly! If you end up saying or doing something boneheaded, it’s a great opportunity to improve your thinking, which would never have happened if you were silent. As Shakespeare wrote, “The fool doth think he is wise, but the wise man knows himself to be a fool.”

I’ve appreciated the opportunities to test myself over the years — the difficult engagements I’ve been on that forced me out of my comfort zone, and which required me to co-opt people into my cause, and become co-opted into theirs. For now, I’m looking forward to slowing down, clearing my mind, and pursuing creative projects at a more human speed, which for me is much more like a sloth (my spirit animal).

One last thing... beware the accelerating world! If you try to match the modern pace of change step for step, it will grind you into a million little pieces. I don’t think we are naturally meant to operate at such a high frequency over extended periods of time; it’s ok to slow down. We need some time to stare at the waves and let our minds settle before making our next moves. Doing this regularly will improve every one of your endeavours.

Many thanks for the memories, and to all in my professional network who have helped me learn and grow. I’m still around, so you can reach me here. Follow my writing here or on summersoul.net if you’re interested (I may post some work-related stuff here). And who knows, if I eventually realize this decision was a huge mistake, I may pop up again and delete this post.

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Here is an NotebookLM-generated AI reaction to this article, with audio-mixed backing music. It’s posted here mainly for those who prefer to listen in a podcast format that read a long-form article. The original article with audio read-through can also be found on the Summersoul website.

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