Getting Ahead: Pathways to Comfortable Career Satisfaction for the Aspirational
Looking at software career options from an earlier place, many folks find themselves both aspiring for career growth and wanting not to be plugging in 60+-hour weeks by mid-career (and rightly so!). There’s a lot of hustle culture out there that promises to get you there right away; while a few folks out there get lucky, most of this is just concealing the outside-the-office time its purporters are plugging in. In hopes of making this wide range of possibilities a little easier to navigate (and with the wish that I could give myself this same resource some twenty years ago), here’s a breakdown of some common and reliable actual paths towards career satisfaction, particularly for those that are young and hungry:
Put in the hours with your employer. Like, a lot of hours. More than 40. You need to both get in the reps and establish a reputation. It’s hard. It’s low-risk. But you’ll more than likely get where you’re aiming. This is “a job”.
Or…
Put in the hours outside of work. Put in enough at your job to get your job done, then keep going. It’ll be more than 40 in total right now. You need to get in the reps and establish a reputation. It’s harder, because you have to self-motivate. It’s medium-risk: you need to self-niche and get good enough at marketing and build an audience or a portfolio or reputation somehow, and you don’t have someone paying you from day 1 and telling you directly what they value. But it’s pretty rewarding. You might get where you’re aiming, and you’ll be at least fine in the meantime. This is “a job, plus a side project” or “a job, plus contracts/consulting”.
Or…
Roll the dice right now. Start your own thing with a narrow niche: find a fit between what you’re willing to do, who you want to work with, and what product or service they want enough to pay for. It’s hard. It’s high-risk. Right off the bat, your expenses mount by the day; the way to outrun them is usually by putting in a lot of hourse. The payoff is high, but there’s no guarantee you’ll make any money at all. If this is appealing, you should probably do it on the side until you get funding or customers or both. This is “a startup” or “a consultancy”.
Or…
Adjust your perspective. This one is the actual superpower. Start moving away from the binary win/lose perspective into a more gradated way of living. You are not winning or losing in your career. You’re on a continuum. From where you stand today, where are you aiming? What will feel like a single step in that direction that you can do in the next week? Do that; call it a win. Know that you’re genetically predisposed to compare yourself to your peers, and hack that to not make yourself miserable: instead of trying to be richer or more successful than them, try to be more truth-seeking, more giving, more interested in identifying where you yourself can grow, more able to hear feedback and learn from it. Doing this takes time—outside of work. It’s mostly time over time, though; better 10 minutes a day for a year than a two-week retreat in isolation. Perhaps ironically, this is a pretty good recipe for career success —but that’s not really the point. It’s hard. It’s low-risk. The payoff is high, and in the meantime you’re pursuing the middle path. This is “enlightenment?” western edition? Or something? More than anything, this is finding happiness right where you are, which makes for terrible cocktail conversation and a lot fewer deathbed regrets.
Resources I’d pass along for folks interested in all of these directions:
- https://www.effectiveengineer.com/book/
- https://jonathanstark.com/
- https://readmake.com/
- https://geraldmweinberg.com/Site/Consulting_Secrets.html
- https://www.annieduke.com/books/ (particularly Thinking In Bets) (summary at https://sive.rs/book/ThinkingInBets)
- https://www.danharris.com/p/books-ee0 (or for the more crunchy-granola crowd [no judgment, this is me too], https://www.tarabrach.com/books/radical-acceptance/)
There’s also something to be said for initially aiming to go T-shaped (lots of breadth, one area of great depth) with the intent of going X-shaped (two complimentary but distinct areas of great depth), but that’s a discussion for another day.
