Should you leave a job you like to roll the dice?

One of the things that really irks me about social media, particularly X and LinkedIn, are the gurus. I’ve found that a lot of the people behind big accounts are idiots. Not like kind of stupid, but like full-on “I stuck my tongue in light sockets as a kid” stupid.

The dumbest hot take that I’ve seen making the rounds is that you should just quit your job and go all-in on your side hustle without reservation. This is criminally retarded.

Storytime

Most of you have been following me long enough to more or less know my story. I walked away from a federal job that I really liked in April 2021. To say that I have no regrets is not a complete picture of my complex feelings when I left. Sorry for using ‘I’ so much.

Anyway, a friend of mine from early in my Air Force career just retired after 22-ish years in, so he is right in the middle of a job search. According to him, it’s a horrible nightmare. No callbacks, getting blown off left and right, no good leads. And this is a guy with almost a quarter century of experience doing highly complex stuff, leading large teams, etc.

You better believe that he is probably not walking away from a job once he gets one. I say all of this to convince you not to bounce from a job you either like or can tolerate the second you start seeing income from a side gig. To be honest, you are setting yourself up for a rough time.

Being an entrepreneur is not the right call for about 95% of the working world. It is really hard. Like, really, really hard. I only did it because we had redundancies already built it, although nowhere near enough savings. And sometimes, enough is enough. I loved my job, but after 7 ½ years of constant unpredictability, it had taken its toll. You can only work 60-70 hour weeks with no-notice all-nighters (literally all-nighters; I slept in my office dozens of times).

If that’s where you are at, then maybe you need to make the leap. Otherwise, you’d be best to stay at your job, leverage it to increase your salary, learn new skills to maximize your pay, and so on. Working for yourself sounds romantic…until it isn’t.