A little over 20 years ago I was at a crossroads. My second company was petering out when our 5 years of building Deltagraph for the publisher ended (they wanted to move into the nascent internet space). At that point I had 13 years experience as a programmer but also 9 years or so experience running a company (at the same time).

I no longer wanted to do both. My first company 85-87 not only built a new kind of spreadsheet program but also published it ourselves. I led the company, did all the press interviews, managed the investors, did all the usual business stuff and also was one of the three programmers and the UI designer. After we shipped the product in early 87 I also wound up in the hospital. Trying to be both leader and programmer was simply too much.

So at that point in 1994 I could have gone either into technical management or continued as a programmer. I chose programmer because it was easier. Today I now realize how wrong I was despite all the great stuff I’ve been able to work on and ship over the past 20 years. Going towards the CTO/CIO/VP Engineering route, which was fairly new back then, would have been a much better plan.

I was in the Bay area for a year around 1995 and worked at Apple for the last half. Apple looked to be falling apart and I left to return to Texas as I didn’t want to see my favorite company die around me. Big mistake.

Not only did Apple begin a huge turnaround a year later when Steve came back, but the whole Dotcom explosion happened. Being both an experienced programmer and leader who understood what it took to deliver (we did 9 major releases of the apps during my time, all of which I built the master floppies for, with no need for hot fixes which were hard to do then anyway) I can only imagine how in demand I could have been. Once you get to the level of one of those titles you can keep moving forward and up.

My sister started as a programmer 30 years ago but jumped into management within the first year and has been a VP at a big company for the past 15 or so years. The huge parent of the travel company I worked for a couple years ago had a CEO who started 15 years earlier as a programmer. Of course these types of jobs can be hard and unpleasant but for that the renumeration is way greater. My sister has 10X the assets I have.

Over the years I’ve seen how little ability you have as a programmer, no matter how good you are, at making a difference or changing things that are broken. I simply didn’t realize how little room you have to advance as just a programmer (or even architect or the like); the power to change exists at a level not available to you as a mere delivery device. Add to that the financial benefits, the higher likelihood of substantial IPO participation, and all the other things you gain access to, and being a programmer means you have to be happy with the opportunity to build cool things.

Over the years the worst places I’ve worked or helped as a consultant for those 5 or so years I did that were almost always due to inept, incompetent or downright idiotic technology management. There isn’t enough room in this blog to list them all.

Take the VP of engineering for a bank who remarked that he didn’t need to understand technology as he managed people, yet still made technology decisions. The CIO at the same place never believed anything his employees told him but believed everything vendors told him. Of course we knew he was taking kickbacks as we kept buying things we had no use for and he kept writing articles for them relating how wonderful their products were for us. Yet we used almost none of it. Some time after I left he was fired and perp-walked out of the company yet immediately got another similar CIO position.

The worst job I ever had started out as what I thought would be awesome. A post-startup had a successful niche in their industry; both they and their arch-rivals (different niche) both wanted to launch into a broader public market and the market was heating up. I was hired as a second programmer. The other programmer and manager had been hired to build a new broader online store as the existing one was too inflexible and slow for a big market. The company had zero technical leadership otherwise, the CEO and the other two founders had no technical experience or knowledge. The programmer constantly talked about how wonderful his backend code was and the manager supported him. I built a front end piece, put up demos, checked in my source every day. When I thought it a good time to integrate I discovered the other programmer after 10 months had checked in—nothing. When I pointed this out the manager said “he never checks in anything until it’s perfect”. Yet no one called this out as stupid other than me. I spent the next two months trying desperately to get the 3 founders to bring in people who could actually deliver (I knew several people) but they were afraid to make any changes and admit they had screwed up in hiring these two guys. Eventually I gave up and left.

A year later after still getting nothing from this guy they fired both of them. They tried to hire some consulting firm but got nothing from them either. By this time it was too late. The rivals? They became a billion dollar public company and I see their commercials on TV sometimes. I always want to throw a shoe at the TV when I see them. We had everything but a damn store and in reality actual technology leadership. If I had been such a person instead of a programmer I would have had the track record and clout to make it happen. But all I was was a programmer.

I could go on and on but the key is that you can’t make changes in how people do things in a technical sense unless you have the ability, the authority and the opportunity. Once you make that call and assuming you find the right places to grow, the sky is really the limit.

When I was on TV (Computer Chronicles) in early 1987 showing our product Trapeze the other presenter was Mike Slade who was product manager of Excel. At the time young me thought him some random marketing weenie (young people can be pretty stupid). Yet he started all these companies later including ESPN, worked for Apple in various leadership roles, was a good friend of Steve Jobs and started his own VC firm.

And today I am still just a programmer. Who’s the weenie now? I doubt I will ever be able to really retire. Thankfully I am still good at delivery (I was recruited into my present job by a former manager who needed what he knew I can do) but still all I will be until I croak is what I am now.

Being a programmer for nearly 35 years and still being able to get things done and ship is still fun and I’ve been able to work on amazing things over the years. But I can still feel the regret of not seeking the challenge of just leadership. In some ways programming was the easy choice. Given how close I got to the whole Dotcom timeframe, or even the return of Steve to Apple, and still had recent leadership experience, I could have been almost anything.

So yes I regret not taking that choice and seeing where it would have led me, yet I would have missed all the fun of writing code and the soul-draining jobs that often come with it where you can’t really fix anything.

I came to a fork in the road and took the one less traveled. Perhaps now I realize why.