I’ll keep it short and practical this week. If you’re in the gig economy, or planning to be, I suggest doing some sort of relatively structured end-of-year review/planning exercise heading into 2020, and taking it seriously. Here are some resources to help you do that.
One of the best ways to take such exercises seriously is to undertake them with a partner. Pamela Hobart has kindly volunteered to run a blind-date matching process to pair people up to do their annual planning/review cycles together (ht Tom Critchlow for the idea).
If that’s of interest, sign up on this google form to be assigned a partner.
If you think you could use more structured support, with processes and models, a few options to consider include:
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Taylor Pearson’s goal-setting masterclass
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Pamela Hobart’s coaching (she has office hours coming up)
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Tiago Forte/David Perrell annual review workshop
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Malcolm Ocean goal-crafting 2020 intensive
While I haven’t tried any of these myself, they are all offerings from people I know, and trust to do a thoughtful job with their models and processes. They’re all gig economy people themselves, so they have a sense of the peculiar challenges we face. So check them out.
The only resource I have to offer myself is a link to this blog post I wrote in 2008, half in jest, How to Make New Year’s Calibrations.
If you have additional resources to suggest, or general thoughts/reflections on annual reviews/planning, or simply want to share something about your own process, reply to this tweet to share.
A few thoughts on the stakes seem called for though.
Regular paycheck people tend to march into the New Year with a good deal of ceremony. It’s practically a parade. But their lives are typically structured and safety-netted enough that doing it poorly doesn’t matter much. The stakes for things like resolutions rituals are pretty low, and the typical cost of getting it wrong is on the order of an unused gym membership.
We in the gig economy on the other hand, tend to stumble unceremoniously into the new year via a back alley, rather than marching into it down Main Street. And usually, there is some actual non-ceremonial reorientation debt piled up to pay off. So your review/planning rituals matter, and this is one of the rare predictable windows of opportunity you have available to do them in.
And the stakes are higher. We have no default structure or safety net to yank us back to safety if we get it wrong.
Full disclosure, I’m personally not very disciplined about end of the year observances, or structured processes, so that’s one reason I’m pointing you to other people.
But I do tend to take a sort of mental vacation (if not an actual vacation) and do some sort of thinking I don’t normally do. Some years, I dabble in a hands-on learning activity during the holiday week, like trying out a new programming language. Other years I just binge-watch some comfort TV. This year, my project is a little different: building a wooden pendulum clock from a model kit.
Whatever your approach to navigating the 2019-20 transition, try and make it a mindful, conscious one. Week-long opportunities to step back from the fray and make course corrections are scarce and valuable in the gig economy.
Happy holidays, and happy reviewing/planning!