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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.


> 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.

You can actually pull the money out of your Roth IRA without penalty of any kind, for any reason. The catch is twofold:

1) You can only withdraw the money you used to fund the IRA (not the money you've made inside the IRA). E.g., if you've put in $20k over 4 years and the account value today is $25k, you can take up to $20k penalty-free.

2) You can't replace the money back into the account past the $5k maximum. So if you withdraw $20k and then don't need it after all... too bad, you can still only put back $5k/year.


LVB: you now what I think you should do? If you don't want to leave the corporate world, and your only gripe is the lack of vacation, negotiate. If your boss gives you a raise, ask if you can trade in 2% of salary for another week: taking an 8% raise instead of 10%. If he can't give you a raise at all, ask if you can get an additional week off instead. If you have to, offer to have any time past your 3rd week unpaid.

People tend to think that vacation allotments are set in stone. They're not, and you can definitely negotiate out of a "reset". If you're used to having 4 weeks, it's not unreasonable at all to ask for that in your next job.

It's weird to me that so many people do the customary +5k negotiation before they start a job but they fail to negotiate an additional week of vacation which would, in most cases, make them a lot happier than an extra ~$250 per month (after tax).


PTO was a part of my negotiation when I was looking for a new job, but it didn't work out. The job market was worse then, and I was quite keen to make the move out of my previous location (it was a cross country move) so it wasn't worth not getting the new job.

That said, over the past week I've been drafting a polite but direct letter asking for the extra week. Sure I've already had the job for a couple years and my bargaining position is ostensible worse, but their need for employees is a lot higher and they have repeatedly said how much they like me, I do good work, future roles, etc. I like the idea of making them sweat a bit (there have been a number of recent departures), and maybe it will pay off.


What stops you from just taking a week of unpaid time off?


I would love to have that option. Unfortunately the only unpaid leave that's allowed is FMLA, and even then you must burn up any built up PTO before it transitions to unpaid leave.

The work, environment and people are quite good at the company, but the leave policies are annoyingly stingy.


I agree. Some companies are more flexible than others on this, so the obvious solution is to find a flexible company.

The good news is that one major corp. I know had an unbreakable policy for years (every new employee starts at the same 2 weeks, NO exceptions) broke this when the local market got so tight they had no choice. So job market timing is part of it, too.

I'll also point out that executive compensation is always flexible, and the OP is coming of an age where that might be a valid path.




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