On the features of a portfolio career

Since starting The Labrary late last year, I’ve been able to work with lots of different organisations and lots of different people. You too can hire The Labrary to make it easier and faster to create high-quality software that respects privacy and freedom, though not before January 2020 at the earliest.

In fact I’d already had a portfolio career before then, but a sequential one. A couple of years with this employer, a year with that, a phase as an indie, then back to another employer, and so on. At the moment I balance a 50% job with Labrary engagements.

The first thing to notice is that going part time starts with asking the employer. Whether it’s your current employer or an interviewer for a potential position, you need to start that conversation. When I first went from full-time to 80%, a few people said something like “I’d love to do that, but I doubt I’d be allowed”. I infer from this that they haven’t tried asking, which means it definitely isn’t about to happen.

My experience is that many employers didn’t even have the idea of part-time contracts in mind, so there’s no basis on which they can say yes. There isn’t really one for “no” either, except that it’s the status quo. Having a follow-up conversation to discuss their concerns both normalises the idea of part-time employees, and demonstrates that you’re working with them to find a satisfactory arrangement: a sign of a thoughtful employee who you want to keep around, even if only some of the time!

Job-swapping works for me because I like to see a lot of different contexts and form synthetic ideas across all of them. Working with different teams at the same time is really beneficial because I constantly get that sense of change and excitement. It’s Monday, so I’m not there any more, I’m here: what’s moved on in the last week?

It also makes it easier to deal with suboptimal working environments. I’m one of those people who likes being in an office and the social connections of talking to my team, and doesn’t get on well with working from home alone (particularly when separated from my colleagues by timezones and oceans). If I only have a week of that before I’m back in society, it’s bearable, so I can consider taking on engagements that otherwise wouldn’t work for me. I would expect that applies the other way around, for people who are natural hermits and would prefer not to be in shared work spaces.

However, have you ever experienced that feeling of dread when you come back from a week of holiday to discover that pile of unread emails, work-chat-app notifications, and meeting bookings you don’t know the context for? Imagine having that every week, and you know what job-hopping is like. I’m not great at time management anyway, and having to take extra care to ensure I know what project C is up to while I’m eyeballs-deep in project H work is difficult. This difficulty is compounded when clients restrict their work to their devices; a reasonable security requirement but one that has led to the point now where I have four different computers at home with different email accounts, VPN access, chat programs, etc.

Also, absent employee syndrome hits in two different ways. For some reason, the median lead time for setting up meetings seems to be a week. My guess is that this is because the timeslot you’re in now, while you’re all trying to set up the meeting, is definitely free. Anyway. Imagine I’m in now, and won’t be next week. There’s a good chance that the meeting goes ahead without me, because it’s best not to delay these things. Now imagine I’m not in now, but will be next week. There’s a good chance that the meeting goes ahead without me anyway, because nobody can see me when they book the meeting so don’t remember I might get involved.

That may seem like your idea of heaven: a guaranteed workaround to get out of all meetings :). But to me, the interesting software engineering happens in the discussion and it’s only the rote bits like coding that happen in isolation. So if I’m not in the room where the decisions are made, then I’m not really engineering the software.

Maybe there’s some other approach that ameliorates some of the downsides of this arrangement. But for me, so far, multiple workplaces is better than one, and helping many people by fulfilling the Labrary’s mission is better than helping a few.

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