Freelancing: A 6-Month Retrospective

Only thing you're missing out on is the ability to work on and towards your own projects.

Not sure about the average freelancer, but most technical freelancers I know see it as a stepping stone towards getting their own little SaaS or iPhone app business off the ground.

If you're working full-time for a company, IME contracts tend to own all intellectual output at your time there, at home or otherwise. This doesn't matter much if all you do is put out MIT licensed experimental programming language parsers, but I wouldn't put many companies above executing on those terms should a product you build in your off-time achieve success.

Earlier this year in the Harvard Business Review, Jody and Matt Miller wrote about a phenomenon that is similar in spirit to that of freelancing hackers, which they dubbed supertemping:

"Supertemps are top managers and professionals—from lawyers to CFOs to consultants—who’ve been trained at top schools and companies and choose to pursue project-based careers independent of any major firm."

It is pretty interesting to see freelancing become a "first-class citizen" in the high-skilled employment world, whereas previously it wasn't widely accepted beyond a few select occupations.

URL: http://hbr.org/2012/05/the-rise-of-the-supertemp/ar/1

These posts are always both inspiring and wrenching for me. I'm mid-career and come from the mold where getting a good fulltime job out of college is what one does. That's simply the way it was, at least in my circles (college, family, etc), and I never considered working for myself. Fast-forward 15 years. Corporate life has actually been pretty decent to me. I've not been jerked around too much, had some opportunity to travel, and have been compensated reasonably well. My wife and I have had a comfortable life so far.

So, what's the problem? LACK OF TIME OFF. I've been stuck behind antiquated US corp vacation policies for a long time, and having had my vacation "reset" due to a job move is weighing on me a lot. 3 weeks total time off (which includes sick leave). I'm almost 40 and have a young family, and more and more I think the current PTO situation is BS. I actually don't mind working in an office 5 days a week, but I would like some more time out of the office.

So it's great to read someone achieving that, but I'm also incredibly jealous. Yes I could "just do it", but that would go against very deep and well-set views of how I need to provide for my family. I'm not able to stomach the risk (and unfamiliarity) at this point. I suspect that it will need to get worse (i.e. my job goes to shit), and that will force my hand and it could get much better.

> Yes I could "just do it", but that would go against very deep and well set views of how I need to provide for my family. I'm not able to stomach the risk at this point.

My suggestion: Temporarily cut your family's expenses down to the bone. Food, shelter, telephones, insurance, connectivity, clothing etc.

Save up six months of the pre-cut household burn rate. Put it into another bank account that doesn't have an ATM card. This is your "I have been hit by a car and can't work for an extended period of time" fund.

Save up three months of the post-cut household burn rate. Put that into your normal savings account. This is your "I can't find new freelance projects for a few weeks" fund. If you're financially adventurous (like me), this can be in the form of available balances on credit cards. (I invest the cash in various speculative places, and then have the CCs in the event that I have no work temporarily. That doesn't actually end up happening, though - it's just a feel-good safety blanket.)

Then, do what the article says.

Worst-case, if you find yourself burning through your three-month, you can always pull the rip-cord and go get another wage slave job. At no point do you have less than six months of runway, so you're safe.

PS: Make sure you're always contributing your max $5k/year into your Roth, too. If you're ever really capital-F Fucked you can eat the tax penalties and get to that, too. I think of this as the "lawyer fees to fight the federal indictment" money.