I have to say that I think the big takeaway is radically different. Riding off the marathon analogy, taking vacations is critical to prevent burning out. In the long run it will keep you more productive and in turn be better for the company.
Tim Ferris has some great things to say, but there's also the inherent risk that when working alone and taking a vacation, no one else is there to watch your back.
Culture at some companies is definitely more what like what you described, particularly at finance firms, but there are definitely cultural shifts happening right now as less college grads are going straight to finance every year, allured by the perks that tech firms have to offer such as unlimited PTO in some cases.
It seems like your situation is very different from that though. Working at a small startup is really hard, particularly when you already have a family. I wish you and your startup the best of luck in the coming year.
Is "unlimited PTO" ever not window dressing for a more predatory policy? Anywhere I've worked with this policy had implemented it so that ever taking vacation was a negotiation with your boss (not something you could just comfortably declare), and it led to not being paid for any surplus vacation days (as none exist but an "infinite" amount) when you do finally leave said job because of burnout.
Anecdotal data point to the contrary: the company I work for switched to "unlimited" as of the 1st of last year. I took more vacation on the unlimited plan than I used to than I had on the accrued-PTO plan (4 weeks vs. 3). So it can happen, if the culture is right, and you have a manager that actually understands the value of vacation for both the employee and the employer.
It can be good. I've had it a couple of places, and never had to do any more "negotiating" than at my job before that had regular metered vacation. Now that I'm somewhere that's not in the really early stages, where I'm not solely responsible for as much stuff, it's pretty easy to just say "hey, I'm going to be out a few days next week" or "hey, this is the time I'm taking off over the holidays."
What's rare, but an extremely nice bonus on top, is when you get to "accrue" a small amount (maybe a week a year) as well that you never dip into but's there to be paid out to you when you leave. But that's not something I'd expect to be able to negotiate for at my next job, so if they didn't have it I'd try to just get a bit more salary to compensate...
allured by the perks that tech firms have to offer such as unlimited PTO in some cases.
"Unlimited PTO" is usually a bad thing, at least in startups. I don't like vacation tracking-- I think it's a waste of electrons and ink-- but the one company over 10 people where I worked that had "unlimited vacation" was a place where 2 weeks would usually get a person fired for "culture fit".
I'd be more inclined to work for a company that offered 5 weeks (more than I need, at this age) than one that offered "unlimited". If nothing else, the former is better because it gives you the ability to say, "I'm used to 5 weeks" in negotiating a job offer and increasing the likelihood of a match. If you say, "I'm used to 'unlimited vacation'" you make it sound like you worked at a disorganized company and you won't get matched.
In the latter case, you can simply say, "I'm used to X weeks", where X is the number of weeks per year that you personally usually took off while on the "unlimited" plan.
When I see "unlimited" PTO mentioned in job ads, I get the sense that someone put it in there because they got the idea (from some medium post or somewhere) that this is what all the other "it" startups are offering, and so hence, they should, too. Without like, you know, taking a couple of seconds to think about what it actually means.
Tim Ferris has some great things to say, but there's also the inherent risk that when working alone and taking a vacation, no one else is there to watch your back.
Culture at some companies is definitely more what like what you described, particularly at finance firms, but there are definitely cultural shifts happening right now as less college grads are going straight to finance every year, allured by the perks that tech firms have to offer such as unlimited PTO in some cases.
It seems like your situation is very different from that though. Working at a small startup is really hard, particularly when you already have a family. I wish you and your startup the best of luck in the coming year.