If there’s one existential fear I have in my career, it’s my age. And maybe “fear” is a strong word here, but it’s something my inner voice chatters about every so often.

The first line of code I ever wrote might have been 1999 as I was graduating high school. It was probably some HTML that was part of some senior project, and I was probably goofing around because it was all very new and non-serious. I never thought I’d still be writing HTML — or any code at all for that matter — 23 years later. Heck, I wound up majoring in international political economy for crying out loud.

There were no mentors back then. Many of the folks I know who cut their teeth in web development those days affectionately refer to this as the “View Source” era, as in, that’s how we learned to code: we right-clicked on a page and opened up the source code to see what was going on. An education in web development was really an exercise in curiosity and self-motivation.

I always wished I had someone to look up to as I was getting started. I guess that’s why I was so drawn to what Chris Coyier was doing when he started CSS-Tricks way back in 2007. We’re the same age, but I was learning vicariously through his very public (and generous) trials and errors. I learned a lot from him then and a whole lot more later when we started working together. That’s about the most mentorship I’ve had in my web development career — albeit, an amazing one.

But where do we I go from here? I’ve learned code. I’ve worked for small, large, non-profit, and all sorts of companies. I’ve spent eight years as an independent contractor. I wish I had advice or some good example to follow when it comes to my twilight years as a web developer.

(And, yes, I do believe I am well in the second half of my career.)

Honestly, I lost my best bet for that when my dad passed in 2010. He worked for himself as a family therapist in a rural town where he ran a practice of social workers and psychologists. He pulled himself up from the bootstraps of an unlikely upbringing and found success through an entrepreneurial spirit that nicely complemented his ability to help people deal with mental health problems. His work was way more important than anything I do, but the parallels of building a stable independent career are what I crave. He passed a couple of years before I went out on my own and I’ve always wished he was around (naturally, I miss my dad, of course) so I could bounce a question or two off him.

How are you planning for retirement?

How do decide when you’re done?

What comes after this?

But he’s not here and there are precious few people who I know who have done web development through their forties. I have no clear picture of what it looks like to wind down a career in this field. And it scares me if I’m being honest. I can stop anytime, for sure! But I want to know what it looks like to do that gracefully and I’m sure there are some considerations specific to the work we do that would be nice to know.

My current plan is to retire in stages because that seems like the most appropriate thing to do in this ever-changing field where the macroeconomics of remote work and diminishing Social Security paychecks come into play. That’s why I started teaching a few years ago. I can teach part-time and ramp that up as I’m winding down my “day” job. Then I can ease out of that if and when I feel like calling it a day. That’s an idea I brazenly stole years ago when Noah Stokes blogged it after turning 38. I’m 41 and that sounds like a damn fine plan to me.

That’s what I have to go on. It’s as much (if not more) of a plan than anyone else I know has. Maybe you plan on writing code until your pruney fingers give up. Maybe you plan on managing a team of folks who are earlier in their careers. Me, I plan on helping usher in the next waves of web development talent feeding that pipeline. I guess we could all be Walmart greeters in our golden years instead.

What other options do we have?

✏️ Handwritten by Geoff Graham on August 5, 2022


  1. # August 5, 2022

    You graduated from high school in 1999?

    If it makes you feel any better…

    I am even older than you.


  2. # August 5, 2022

    I’ll be 39 this year, and this really speaks to me. At least I’m not alone.

  3. # August 5, 2022

    Graduated in 1984 and still looking up stuff on @css

  4. # August 5, 2022

    You might not know it, but I watched what you were doing closely — especially in the 960gs days — to help guide my career. You’ve been my mentor, buddy!

  5. # August 5, 2022

    I am glad this old head was able to help young whippersnappers like yourself.


  6. Noah Stokes
    # August 6, 2022

    I’m into this plan Geoff! (of course, I may be biased 😜)

  7. # August 6, 2022

    Dude, you’re still a kid. I’m 59 and have been a developer for 29 years. Still going strong, working for one of the big NYC digital agencies. If you want to know how to prepare for retirement, put as much money as you can into a 401(k) and if you have a mortgage, pay extra.

    • # August 6, 2022

      My concern is a lot less about how to prepare for retirement (I’m quite good there, in fact) than it is knowing when to retire. It’s also a lot less about fatigue and burnout (I’ve already decided to throw the towel in on large agency work as a lifestyle choice) than it is what it looks like to slow down. I suppose it’s the same feeling in any other line of work; I just feel that this line of work has less clarity than others.

  8. # August 6, 2022

    Thanks for this! I’m right there with you in terms of when and how we started in web development. Last year, I switched to being an accessibility engineer for some of the same reasons you note and it almost feels like a second career. I hope to be teaching grad students next year


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