Planning for 35 years

I spent some time last week at my alma mater, the University of Michigan. It was a very humbling experience - the school uses Google Workspace (which I still call GDocs), and the students were really amazed to meet someone who had a part in creating it. If my overwhelmed freshmen self had known back then (over 35 years ago) that I’d some day come back, and the whole campus was using my software…I think I would have hidden under my bed for a week!

There’s a question the students asked in almost every setting: how did you plan your career? And usually when I am asked this question, I say that I didn’t, that it would have been impossible to predict all of the changes 35 years ago.

In this setting, it was even easier to say that - most of the things I’m working on now, like AI, were around in only rudimentary forms if at all back then. The first three startups I did were pre-internet (it existed but it had maybe 100 people on it in academic institutions). The iPhone in my pocket is roughly the equivalent to 25-60 Cray One computers (depending on how you count), which was the unreachable cool computer when I was just out of school.

It’s a lot of change. The last 35 years were really chaotic and hard to predict, and I think the next 35 will be more so. There are lots of exciting changes happening technically right now, and we probably can’t see most of the really interesting ones that changes now will unlock in 10 or 20 years.

The advice I gave is more process, than goal. You want to learn to learn, because it’s definitely true that you won’t have all the skills now you need in even 10 years. I remember fussing about whether to learn C or Pascal. Ultimately, I wound up learning to code in 10 languages for money (and more for hobbies), and it wasn’t an important aspect even. Pay attention to the things that feel easy to you, where you don’t know why people want to pay you for something that might even seem fun - we tend to undervalue things we are really good at because they are easy to do.

Keep learning, find your place where you add the most value because of your interest or your natural skills, and invest in a way that compounds (meaning, don’t waste time on things like social media that don’t add up - learn a skill and then stack it on top of another skill, and another…). You’ll make good career decisions and bad ones, but if you build a mechanism to be aware, be adaptive, and compound value in the things you’re good at, you’ll do fine, no matter how choppy the sea.