Let me try to offer some responses (and without minimizing some of the legitimate negatives about the freelance lifestyle that you highlighted):
“You’re Free, But You’re Not Really Free… I ended up writing blog posts for local breweries in Montana and writing billboard copy for apartment complexes in New Jersey. It was weird.”
Find a niche and market your expertise in it (I’m not preaching here — this is something I need to work on too, at least the self-promotion aspect of it!). Alternatively, decide upon what you niche(s) are and go out prospecting to find clients yourself. By the way, my first clients were all over the place too — I believe I was writing video descriptions for a clickbait website at one point! Having firm niches will get you past the stage of sporadically taking on whatever works comes your way …. which, sure, will feel really weird and unfulfilling.
“You’ll never REALLY be in control as a freelancer — you’ll be stuck in this perpetual cycle of winning clients, losing clients, and searching for clients again until the day you die.”
Mindset shift. That’s how it is for a lot of small businesses. If you don’t want to have to ever engage in marketing yourself, you can get a job in a company. But even then you might find yourself getting hired (winning a job), getting laid off/fired (losing (a job), and searching (for your next job)….
“You’re Creating, But You’re Not Creating Stuff You Want To Create”
a) Find clients that are more aligned with your passions and interests. This will make the work you do more fulfilling and enjoyable. For instance, I’m a Linux geek so always assumed that tech was the best and exclusive fit for me. Don’t get me wrong — I still enjoy writing about technology. But I recently began working with a couple of “lifestyle” clients — very raw stuff about the authors’ experiences with mental health issues (I’m a ghostwriter). I found it surprisingly fulfilling and recharging.
b) Don’t stop writing. I also find it really hard to find time to write when …. I’m already doing that for clients. I used to blog a lot and loved it. So I simply started again ….. but I’m doing it for more enjoyment than to raise my reputation/visibility, although I wouldn’t mind a bit of that either.
I’m big into multimonitor computers and recently posted on Medium about VESA mount configurations. I’m 100% aware that most people would find this subject eye-rollingly boring. But I enjoy writing about it and a few people might find it interesting.
“You’re Not Really Achieving Your Main Goal.” Which you list as not working a 9 to 5 / freelancing as a side hustle / or because you’re out of work.
I took up freelancing because I thought that working with multiple clients and clients in a bunch of different industries and clients in different countries sounded like a better way for me to gain experience than working at my (then) job.
Then again, I’m a native English speaker that lives in a non native English speaking country …… and I thought that I could put my writing skills to much better application than stringing together sales brochures for an early stage startup (without wishing to disrespect my former employer).
My ultimate goal is to transition from :
Freelancer → Agency owner → Startup owner (yup, I have an idea!).
The road is brutally hard. I won’t argue with you on that. But I don’t feel like I’m travelling down a futile path.
As for the rest of your points (the positive) — I’m in firm agreement. You get a lot of amazing skills from the journey.
Best of luck!