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25 Years of Software Developer Lessons Learned

Dean Radcliffe
・4 min read

In January 1996 I set foot in my first web development job - an internship with Cybermundi.es during my Study Abroad semester in Madrid through Boston University. In January 2021, with a few interruptions of "funemployment", I'll have spent 25 years within the web development field. Between developing, teaching, consulting, and sabbatical, I am grateful for what it's taught me, and I have great hopes for the next 20 years.
The real story about these past 25 years is that - most of the things I thought would be true about my career at this point - aren't in fact true! This post is about those realizations.

I can't say I've 'found my place' in the field any more now than in my first 5 years. I can't say I've eliminated Imposter Syndrome, or reached a place where I'm secure that I can't be fired, let go, or not hired. I'm not close to an early retirement. I am more humble about my ability to keep up with the pace of technological change.

And here are the biggest misconceptions I've been disabused of along the way:

At year 3 I thought physical discomfort from having a desk job was inevitable. It turns out it can be systematically eliminated with exercise and ergonomics— in fact it must be if you are to have any longevity in this field.

At year 4 I thought I'd rotate my career wildly every 4 years. It turns out starting at the bottom in a new field, once you have some capital/skills in one field, is not very easy. Pay cuts are no fun.

At year 6 I thought I'd pulled an hourly rate I'd never see the equal of. While there are ups and downs, and that was relatively high, there's no ceiling, especially when focusing on in-demand skills. There's always something you could learn to make more if you want.

At year 7, then again at year 22, I thought I'd become a developer-trainer - primarily a teacher not a maker. It turns out while immensely rewarding, teaching has demands I've not yet been able to conquer sufficiently. I now seek the learning/teaching element within the relationships and many benefits I have as a developer.

At year 10, I thought Object Oriented Programming was the pinnacle in terms of architecture. I now feel that LISP and Functional Programming is more fundamental, and ultimately more expressive.

At year 13 I thought Ruby was the way I'd want to code forever. It turns out having code running in a browser, widely available, is more important than having a precise syntax/runtime DX, and I'm all in on JS now.

At year 17 I thought I'd taken my last development job and might become a yoga instructor. See that point about starting at the bottom in a new field, with less pay.

At year 19 I thought I'd be in business for myself forever. It turns out the complicated tax situation, and changing teams often grew old and I began to seek stability by year 22.

At year 21 I thought mental health took care of itself. It turns out it needs care and feeding like all worthwhile endeavors.

At year 23 I thought I'd joined my last full-time development job. A layoff from that job led me to begin the one I have now, which I have no intentions of leaving.

And I'm sure more misconceptions will continue to get stripped away as the years pile on, which I look forward to!


As I step into year 25 as a coder (0-based index), my coding approaches are generally the same—just a bit faster, a bit more knowledgeable, and a lot more humble about what I don't know. 

The most surprising thing about where I'm at is how my career has fueled growth in non-career areas. I am entirely transformed in ways my 20 year old self would be delighted to see. I've always found the demands of this career have left time, money, and curiosity for skill development outside of work. I play several instruments now, including one of my own design, well enough to play with others or for audiences. I ride 100 km bike rides. I play with my kids for hours, and teach them as much as I can. I ski with my wife down Colorado black-diamond slopes above 15,000 feet. Life has been good to me. 🙏

My next 20 years will be themed around bringing those outside-of-career investments back toward my career. I am taking the discipline and goal-setting from my athletic endeavors, the precision and pattern from my musical hobbies, and the social and development from my life as dad and husband, and bring them all to bear on making my career an even better place to be for me and those around me.

I will work on adapting in ever more dynamic ways, to the externalities that change this field constantly. I will take inspiration from colleagues, people who think differently than me, and who challenge me. I will seek the experiences that offer me the feedback I need to continue to be who I want to be.

That's what 25 years of being a professional software developer has taught me, and why I'm more excitedly going into the next 20 than ever. Happy 2021 y'all - what are your intentions for your development careers, let me know!

Discussion (1)

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Dean Radcliffe Author

As to why "the next 20" as if that's some sort of retirement date, it's not. I'll be posting soon about the 20 year athletic endeavor I began 16 years ago, which is going quite well—and 20 is just a nice number to subdivide.