Death: A Career Plan

Knight, Death, & the Devil — Albrecht Dürer

I frequently discuss career planning with my coaching students. I don’t often engage in career planning myself. Partly that’s because no career shift I’ve ever had has been planned, but partly because, well, I’m 99th percentile among geeks for age & my concerns are not the concerns of most geeks. However,…

I’ve been thinking about age and its effects for a year or so. In particular, the dramatic rise in the time value of money caught me by surprise. A dollar today is worth infinitely more to me than a dollar after I’m dead.


If you want a good night’s sleep, definitely don’t go here and enter your deets. You will end up staring at something like the following for hours.

Simulation of various times of death, some uncomfortably soon
Simulation of various times of death, some uncomfortably soon

I don’t have a single life expectancy, I have a range of possible quality/quantity pairs. For simplicity, I want my career plan to support 3 scenarios:

  • Sudden death. I know it’s icky to think about, but look above. I don’t want a plan that has me working really hard for the next 4 years only to conk out before I can enjoy it. The end of every year/month/day should be a just fine place to call it.
  • Ten years of gradual decline. I’m spewing interesting ideas currently, as good as any I’ve ever had. I don’t expect this to continue indefinitely, so I want to make hay while the sun shines. I want a plan that helps me develop & explain my ideas as I go along.
  • That annoyingly sharp and energetic 90-year-old. If I do sustain mind & body I’d like a plan that can keep going as long as I want to keep going.

I specifically don’t need a plan should I be suddenly incapacitated. At that point decision making devolves to my kids. I’d like to leave them financial resources so I’m not a burden but my career is over at that point.

The Goal

How Will You Measure Your Life? asks a useful question, to which I have an answer: on how many of my remaining days will I wake up and ask, “What do I want to do today?” I had a stretch of almost a year pre-Gusto where I got to ask that question most days. Glorious. I want more of those. How am I going to get there? Time to move from principles to application.

A Plan

One element of the plan is to continue working at Gusto. Yes, every day there is a day I don’t get to ask, “What do I want to do today?” but:

  • The money I make enables me to ask that question in the future &
  • I enjoy my work there & the people I work with.

Here’s a puzzle relating to “vesting appreciating stock” kind of work. If I had $50m vested and $50m to go, I would quit today. That surprised me. Why would I walk away from $50m? I don’t think of it as walking away from the money but walking towards the time. Given my extreme time value of money, 2 more of my prime years getting to ask, “What do I want to do today?” is worth far more to me than the additional financial options provided by the extra money.

At the other extreme, if I had $50k vested and $50k to go, I would also quit today. Vesting all of it wouldn’t create the financial freedom to be able to ask, “What do I want to do today?”. Instead I’m in the middle, where sticking around creates new financial options even though I’m burning precious days to earn them.

(I’m aware of what a champagne problem this is. Oh boo hoo I have to keep working past 60. Hey, lots of people have to keep working past 60. At jobs they hate. That won’t create options for a comfortable future. So I want to keep my discontent within reasonable bounds.)

The “venture” part of my career portfolio, the part that has some small chance of providing me with financial freedom sooner than my Gusto work, consists of 2 parts:

  • Angel investments. I enjoy talking with founders & scalers & I enjoy it even more when I have a stake in their success. I like to think conversations with me increase the value of my portfolio companies, but it’ll be a while before there’s any confident validation of that hypothesis.
  • NFTweets. I want to spark a conversation about the future of software development, since we seem to be sliding back into the past of software development. I also want to make the conversation relevant to a new generation. NFTs seem to be attracting substantial energy right now. My experiment is to combine them. I’m going to try minting my more popular tweets as NFTs and see if that stake in the conversation encourages participation.

What I like about these explorations is that they align well with likely answers to my “What do I want to do today?” question — talking about, researching about, teaching about, learning about, writing about, & applying software development. (Music, art, travel, & fitness are all possible answers to “What do I want to do today?” but that’s a story for another day.)


How does the plan stack up for the 3 scenarios?

  • Sudden death. Seems fine. Yes, every day isn’t perfect bliss between now and then, but I’m not doing anything I hate and I am doing things I enjoy.
  • Gradual decline. Seems okay. I’d like to be cranking on ideas full time over the next 2 years & I won’t be, but I will have some time to devote to my studies.
  • Spry 90. Seems good. I’ll make enough (knock on wood) to fund financial freedom indefinitely & in this scenario I’ll have many years to enjoy it.

So that’s the plan: vest out at Gusto, angel invest, & take a shot at NFTs. Let’s see how this goes.

Kent is a long-time programmer who also sings, plays guitar, plays poker, and makes cheese. He works at Gusto, the small business people platform.