Coming up on my 4-year anniversary at a company, having just returned from 2 years in a foreign office, I told my Director I'd like a 3rd week of vacation and no more money. Just treat me like I'd been working here an extra year.

He got me a $5,000 raise, no extra vacation time. Said that he did his best and he was the type of person I'd absolutely believe.

Ever since then, in my mind, a vacation day has to be worth more than $1,000. Simple economics, right? Somehow giving me $5,000 maximizes shareholder value more than giving me 5 extra days off.

My next job was more generous with vacation. They used the accrual method with a maximum and there was an extended period where it had become difficult to take time off and they'd stopped putting our PTO balance on our paystubs... so at some point I track down where to find the info and realize I'd lost 10 days of vacation accrual.

I about lost my mind and HR couldn't understand why I felt like they'd cheated me out of more than $10,000.

Felt trapped in the job forever 'cause eventually I'm earning I think 27 vacation days per year, and 10 to start is pretty typical, maybe 15 if you're lucky... And as much as we might like to think everything is negotiable, reality on the ground is that very little besides salary can be successfully negotiated.

A friend of mine told his boss “I’m going traveling for three months starting in January. Am I quitting or just taking a leave of absence?”. It worked.

To negotiate more vacation days at hiring, you need multiple offers. Then you can tell them “I will accept your offer if it includes six weeks of vacation. Otherwise I’m going to Facebook”. It probably means negotiating a little less hard on pay since you need to focus to get it. But that’s probably fair.

Nothing is certain, but remember that there's a difference between negotiating "unpaid time off" and "vacation days."

A vacation day is a paid thing. Unpaid time off is not. It's all money and productivity in the end, but in many companies it's easier to negotiate unpaid time off, than to negotiate extra vacation days. Even if the money works out the same in the end.

First rule of negotiation is you have to be willing to walk away if you don't get what you ask for. Could be you weren't willing to say "no thanks" if they didn't budge on vacation time.

Fwiw, Google allows for unpaid time off of less than 30 days. Your salary stops during that time, but benefits and so on stay on, which is nice rather than going into "Ugh, need to figure out COBRA".

Google also has up to 5 weeks paid vacation in the US, starting at 3 weeks when you join. After 3 years, you move to 4 weeks, and after 5 years you max out at 5. Other countries basically have their government mandated time off rules, but 5 weeks plus unpaid plus holidays is pretty good.

Each week of unpaid time is thus about 2% of salary. That said, I'm definitely in the minority in using unpaid time off (though, even more strange for me is how many colleagues let their vacation accrual reach the maximum and even forfeit days...).

You do have to leave occasionally to have believable leverage. I’ve found that if you announce you’re leaving and will quit if you have to they’re much more amenable.