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You marry someone with good benefits and have them cover you.
This.
lol
fruits and vegetables
You get mediocre coverage from the marketplace. Medical is alright, but the dental plans are essentially fake. Freelancing has been helpful, but I’d still prefer a full-time job because of the benefits.
S-Corp that pay for owner’s marketplace insurance, mysolo401k for retirement savings.
You can do all kinds of other S-corp deductions if you work with a tax planner and are careful with records. IE carving out your "office" space, and basically any business expense tied to doing business. Most people dont want to do the work to track this but it's so worth it.
I’m a longtime freelancer. I would suggest getting on Cobra, if possible once you quit your job. Health insurance on the Marketplace is very expensive if you want to maintain your current health plan. Another option is to wait until you book a job. Most agencies offer health insurance to freelancers. That’s the one I’m on now. When this gig ends, I’ll go on Cobra. Rinse & repeat.
As for retirement planning, you can do traditional IRA and/or Roth. Or you can find a financial adviser to guide you.
One note of advice before you pull the trigger on FL, make sure you have at least 6 months of living expenses saved - some here would say a year given the last two years of this ad recession.