Employees hunt (or are head-hunted) for jobs. Periodically. Every 4 years on average in the United States.
Entrepreneurs launch things. Serially. Winning big enough to stop, with your first startup, is very rare, as is stopping after your first success or failure.
Gigworkers? We leap into opportunity spaces. Not just once, but repeatedly. In the most extreme case, every new gig is a leap, and since you ideally have many gigs going in parallel, you are always leaping on some track. Sounds exhausting? It can be. But it need not be. And on the plus side, it can be exhilarating.
The first leap is special though, both in terms of significance in your life story, and in terms of the extra preparation it takes. I’m going to do a short series (3-4 posts perhaps) on taking a first leap into gigwork, and retaining the goat-like leapiness indefinitely. It is primarily targeted at those of you who are either planning to make that first leap, or have already jumped and are failing at it.
For those of you who have already made your first leap, this series should help improve your leaping habit, as you eye leap n+1, and also help you reflect more clearly on past leaps.
Leaping takes a very different kind of preparation than job-hunting or startup-launching, but it does have one thing in common with those other two kinds of starts/restarts: it takes more scripting and preparation than you might think.
Most people under-prepare for job-hunting or startup-launching, but they tend to wildly under-prepare for the gig-economy.
Why?
Because a gig economy has no default, ceremonial starting point. No initial focus of attention to get you started.
To prepare for a job search, you update your resume, search job sites, and let your friends know you are looking.
To prepare for a startup launch, you brainstorm ideas, make prototypes and prepare pitch decks.
Even if these activities aren’t quite the right things to be doing, they do get you thinking about preparedness, and you might bootstrap from those formulaic behviors to more imaginative preparations that work better.
But there’s no such obvious ceremonial starting point for scripting a leap into the gig economy. Only a joke one — getting business cards.
Well, actually, there is one real starting point: getting and staying married to someone with a job, who is willing to support your risk-taking and backstop your first leap with their own stability (and you might have to reciprocate in the future if you want to be a gigworking couple).
But this is obviously not a decision you should make solely to hedge against the risks of leaping into the gig economy.
Also, three factors are making marriage less of a hedge against gig-economy risks.
First, jobs are turning equally if not more risky.
Second, there is a much higher chance than you might think of both of you wanting to make a move at the same time, often triggered by parallel behaviors like moving to a new city. In my case for instance, my wife quit her job and took a new one right around when I took my first leap, and we moved to a new city.
Third, more and more people are making their first leaps into the gig economy very young, long before they consider getting married. I made my first leap at age 37, nearly 6 years after I got married, after 15 years in the paycheck world. Many gig-economy aspirants I meet this days seem to be leaping in right after college or high-school, and at least a decade before they are likely to get married.
So bottomline, most people never script their first leap at all. So their unprepared leaps turn fatal (too often, literally).
This happens via three mistakes.
Three Mistakes and a Funeral
The biggest mistake you can make in launching a gig economy career is to think it is pure improvisation. Movies and TV shows encourage this misconception by portraying characters who quit in a huff at some last straw, some final unbearable assault on their dignity or values, and just make it work somehow. Think Jerry Maguire or Michael Scott in The Office declaring, “You have no idea how high I can fly!”
The second biggest mistake you can make is thinking the kind of scripting that works for either job-searching will also leave you prepared for the gig economy as a sort of bonus. After all, a gig economy is just a series of temporary jobs or a sort of I-am-the-product startup, right? Wrong.
The third biggest mistake you can make is to treat preparation for the gig economy as some sort of natural and pre-defined Plan B you automatically land in if you fail at the the other two. As though nature has very kindly arranged the gig economy as a sort of backup safety net. This idea has become just kinda-sorta-true enough (thanks to Uber and Lyft in particular) that it is the worst mistake of all, since it can tempt you into downwardly mobile trajectories.
Most people manage to make all three mistakes at once, and as a result, don’t so much leap into a gig career as crash unceremoniously into one, against their will, having been kicked out from a job or other seemingly safe-space situation (a job or other support system they thought was more secure than it was), with nowhere near enough logistical or psychological preparation.
How do you think that turns out? The leap turns into a crash.
Anatomy of a Crash
Crash-landers almost never make it well enough to last. They limp along just long enough, physically and psychologically battered, to either get back into a job (often a worse job taken out of desperation), or find a stable but unhappy situation as a dependent (via reluctant parents or a resentful spouse).
And many never make it at all. Unplanned crashes into the gig economy can go so badly, suicide is unfortunately a way out that many choose. It is a particularly severe risk for men.
If they survive and crawl back into the job economy, from the vantage point of failure, they help amplify the unfounded rumor that the gig economy is some sort of utterly unpredictable and precarious Hobbesian wilderness where you have to be some sort of lucky, unprincipled, mercenary hustler-barbarian to survive.
This is just plain false. With the right preparation, the gig economy is no more risky or uncivilized a place to be than the modern paycheck economy, or the entrepreneurial economy. The risks are just differently distributed, require different patterns of preparation prior to the first leap, and different ongoing risk-management behaviors.
There are two broad subsets of preparation required: inner and outer, which I’ll cover in the next two posts.