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I think this was a huge thing that I had to overcome when I was first starting out in my career. Everything up until that point had been very prescribed. Graduate-High-School, Get-into-Uni, get-good-grades, graduate, write-resume, get-job........... and then there's this chasm of wisdom. 

Changing jobs is SO scary, it's the complete opposite of  "a bird in the hand is worth two in the bush" and it took several job changes before I could feel relatively confident that I could find some kind of job again in the future if something went seriously sideways. 

Maybe it's just my temperament that I've never had a lot of confidence in the world having my back. I like to have things lined up just so before I try anything. I think it holds me back from experiences and opportunities, though, so that's something I'm working on :)

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Anonymous

As someone who has had almost my entire working life as freelance/startup(s), I'm not quite sure how I got this far... But emprically you can know that you've done it enough to be likely to be able do it again (find the next thing to work on) when you need to!

kaitou

It seems that every time I had to change jobs was due to layoffs. (Well, there was one buyout, but that was followed by another layoff.) Luckily, I knew someone at each of my next jobs. It's definitely a lot easier going to a new job where you know someone. Another good reason for networking. Linkedin helps here: if you're interested in a company (or they're interested in you), you can use it to see if someone you know works there.

Ilana

Wait what are those questions?? Lol. Ive switched jobs every 2-4 years and it's getting to be that time again....

kaitou

Note: you don't even need to be following the person to find them. (I had a job offer from one place and found two people there that worked at previous employers, but I didn't follow as I didn't know them (I knew their names). Turns out that one of them, the hiring VP, knew me by reputation from one of those previous employers, even though we weren't in the same department.)

Ilana

I've even used it to reach out to people with a similar position to the one I'm applying for. 90% of the time peoppe are chill and helpful!