On crossing bridges
Many of the questions I get about going 1099 concerns the administrative stuff (forming an LLC, getting insurance, etc.).
While I'm happy to share that information (I include it in the book), I always emphasize that the first thing you need to do is actually get a 1099 gig, the admin stuff can come later.
There are a couple of reasons people gravitate towards the admin stuff though.
The first is that it is easier than doing the hard work of building skills, networking, and then pitching a 1099 gig to prime PMs. It's a form of procrastination.
The second is that aspiring 1099s are deeply worried about going to jail or getting sued or not getting a 1099 gig at all if they don't do the admin stuff first. Caring about the admin prematurely is a way to reduce anxiety.
But I recommend crossing that bridge when you get to it. You should realize that you can do the admin stuff relatively quickly, but no amount of admin work will, on its own, get you a 1099 gig.
Cross that bridge when you get to it, and not any earlier.
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The fact that you can’t cross bridges before you come to them is liable to seem dispiriting, as if it leaves us with no option but to keep trudging vulnerably into the fog, trying not to think about sinkholes. But it contains a hidden gift. After all, if you’re hopelessly trapped in the present, it follows that your responsibility can only ever be to the very next moment – that your job is always simply to do what Carl Jung calls ‘the next and most necessary thing’ as best you can. Now and then, to be sure, the next most necessary thing might be a little judicious planning for the future. But you can do that, then let go of it, and move on; you needn’t try to live mentally ten steps ahead of yourself, straining to feel sure about what’s coming later. You get to stop fretting about literally everything other than how to spend the next instant in a wise, enjoyable or otherwise meaningful fashion. Finite human beings need never worry about anything else.
Want the full playbook? Check out Going 1099.