Take a leap

I love working for myself. I could make more in a corporate job, but it would not allow me to live my life how I want.

Same here. The only caution that I'd add is that you have to be willing to "beat the bushes to a bloody pulp" in the early years if you want to have any hope of establishing a small business that can literally keep you, and possibly your family, afloat.

I've been doing this as a side gig (and I'm now pretty much semi-retired) since 2008, and I know in my heart of hearts I could never have truly made a living with my business because I'm just not the kind of "bush beater" you have to be in order to get a large enough practice/client base established and to have enough constant stream of jobs in the break-fix world.

If you want to be an MSP, you can control your cash flow better once you have a (relatively speaking) small client base. I never had any desire to enter the MSP world, but many others do, and as much for the kinds of predictable cash flow that sphere allows as anything else.

The only thing I miss about being other-employed (as I worked for larger companies in the private sector and in the public sector) is the benefits packages that come with those jobs. I still think it's ridiculous that the USA relies on private employers to provide health insurance, for starters. Had the ACA actually put together a public option, that's what I'd have taken, but if it weren't for the ACA (AKA Obamacare) I would not even be able to afford health insurance at this point. And you do have to consider that in the mix, too.
 
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