There’s a gig economy disease that will likely strike you within a couple of years of going indie, if you succeed by sticking the landing on your first leap. You’ll find that you have periods with plenty of nominally “free” time, but mysteriously, no time for the kinds of personal passion projects, such as writing, independent research, maker projects, or travel, that probably motivated you to quit in the first place. I’ll call this disease sneakoffproofitis.
The problem is, as a free agent, you are your own boss, and you’re likely a bad boss, unable to relax, and driven by fretful anxiety about lining up the next gig. That would be bad enough, except that you’re also an omniscient bad boss. You know all your own tricks, and nothing is hidden from you. You can’t sneak away from yourself.
You have sneakoffproofitis.
Here’s what sneakoffproofitis looks like.
Your bank balance looks healthy for the moment. You have enough work lined up so the cash flow looks good for the next few months. You’ve only committed a modest fraction of your hours — say 10 a week — to deliver that work. You’re temporarily cash rich and time rich. It’s a sweet situation, right?
So why is it so hard to take your time/money surplus and do something interesting with it?
The thing is, fun things are only fun when you sneak off from things that feel like “work” to do them. There is a certain creative freedom that is unleashed when you’re using up “free” time that feels like it is “stolen” from commitments towards “necessary” work. The courage demanded by the time theft fuels boldness in the sneak-off activity.
This is funny because the idea of time-theft is only well-defined for robotic labor where you are paid to execute a production algorithm, with a clear relationship between time and output, rather than apply knowledge. It is incoherent when applied to knowledge work where there is only a weak correlation between time spent at work and the quality/quantity of output.
But our sneak-off instincts are still linked to robotic labor modes of production. Time isn’t high-quality creative time unless it feels a little bit stolen (which is why, paradoxically, fuck-you money can be a creativity killer).
The work of the knowledge worker is never done. You can always do an infinite amount of work for a finite piece of output. There are always more plans you could make, more background research you could do, more skills you could develop, more trends you could stay updated on, more refinements you could add to the slide-deck, more Q&A you could prepare for. Knowledge work is something like insurance, and it can always be made to violate the law of diminishing marginal returns if you’re neurotic enough.
This is as true of the free-agent life as it is of the paycheck life. There’s always more lead-generating blog posts you could write, more pitches you could send out, more tweaks you could make to your website, more spec-work you could do to go gig-fishing with, more RFPs you could respond to, more clever tweets you could put out to draw viral attention to your soundcloud.
And the bad-omniscient-boss side of you knows this. And won’t let the sneak-off-to-play side of you sneak off to do anything else while there are “productive” things you could be doing. That’s sneakoffproofitis.
What’s the cure? Well, you could get brain surgery to separate the omniscient-bad-boss you from the sneak-off-to-play you, and have the latter hide stuff from the former (weirdly, things like this do happen with brain-damaged patients), but there’s an easier way. You ratchet up the boldness of playful-you and sneak off despite the fact that the omniscient bad-boss is yelling at you.
Because here’s the secret: Omniscient-bad-boss-you is all-knowing and all-seeing, but not all-powerful. Omniscience does not imply omnipotence. In fact, omniscient-bad-boss-you is quite impotent compared to your old other-person boss. What are they going to do? Fire you?
You still need a principle to manage your sneaking-off though, and a way to balance sneak-off behaviors against money-making behaviors.
The principle I suggest is this: pay yourself first. You have probably heard that line from financial advisors. The idea is to put money in retirement savings accounts first, before spending money on other things. It’s that idea, except with time, and with sneak-off activities rather than a retirement account being the target.
So when you have some freedom in how to allocate time towards necessary commitments (for example you have 5 hours of work due to a client, but the deadline is a week off, and a to-do item to update your website before a speaking gig two weeks away) versus sneak-off activities, sneak-off and have fun first.
Subtle point: you have to fill up all available time with necessary activities before you can actually sneak off.
So if you typically plan in terms of a 40-hour week, on Monday morning, make a to-do list of “necessary” things that “must” get done “asap” and will take 40 hours. For safety, overcommit, and put 60 hours worth of work on the list.
Then sneak off.
Before attacking that list.
Sneaking off from an under-full to-do list doesn’t work, just as weight-training with no weights doesn’t work. You strengthen your sneak-off boldness by stealing from committed time, not by clearing and occupying “free” time. That’s just a hobby bad-boss-you tolerates.
Sneaking off is how you reveal your own sense of priorities and urgencies to yourself. You don’t know whether or not something can wait unless you try to sneak off from doing it. And unlike carved out “free” time, sneak-off time has no preset boundaries. How long you stay in sneak-off mode is determined by the tug-o-war between your to-do anxiety and the strength of your absorption in the sneak-off activity.
Yes, your omniscient bad-boss side will scream and bully, but you can ignore that. Learning to ignore your own screaming and bullying is the whole point of sneak-off behaviors. Quitting a paycheck job and earning your freedom from others is the easy part. You aren’t truly free until you’ve earned freedom from your own ridiculous expectations of yourself.
The logic of paying yourself first is similar to retirement savings prioritization logic. The things you do in your sneak-off time are the things that have a chance of turning into long-term compound-interest assets (though watch out for a related disease, projectitis: omniscient-bad-boss you will attempt to turn every such activity into a legible “project” the moment they smell a “return”, and ruin both the fun and the possibility of a return; eventually you have to let that happen if the activity grows enough, but delay the onset of projectitis, and stay in sneak-off-and-play mode, as long as possible).
In the short term sneak-off activities are bugs in your self-imposed productivity regimen, but in the long-term, they’re the main feature of the lifestyle you’re constructing, and the most necessary among all the things you must do.
Neglect sneak-off activities at your own peril. All work and no play make Jack a dull paycheck employee, but a dead free agent.