This, combined with colleagues visibly taking advantage of the time off available, helped ensure a healthy approach to unlimited time off.

Thats doing it right. Or pay people for the vacation time they don't use.

As a result employees can't just bank their vacation hours and get a big payday when they leave. It tends to only take a couple years to get up to the max, and you end up with "use it or loose it" pto.

Which is why employers almost always cap in some form or another; the exact mechanism is partially determined by state law.

I worked for a company once that, during a bad spell, eliminated an accrual cap to encourage people to bank vacation. The result was that a not small number of people who weren't really into taking vacation just let their balances balloon. The company eventually forced people to work down their balances.

From the business perspectice services rendered previously is "nothing", because you can't get any more value from that

This is is why it's important for team members to explicitly encourage each other to take breaks and vacations. I've often told a coworker, "stop working! Take a long weekend!".

The best UPTO environment I've ever seen had managers who asked about time off in one-on-ones and pushed people who said "none" to take more. It also had a lot of acceptance for 'aimless' PTO; justifying your trip to the Andes is easy, but people take PTO more consistently if no one's expecting a better story than "sleep late and run some errands" or "play a new-release game".

Also once teams and management get used to people taking time off, the business processes also become more resilient to people missing for a week or two and taking PTO becomes less of a problem for everyone. Suddenly someone missing for a week is just not a big deal.

It occurs to me that Google somewhat famously adds artificial downtime to their services to make sure no one is relying on 24/7 uptime. I don't want to reduce people to server-equivalents, but I'll bet high vacation rates are a pretty good way of making sure no one relies too much on individual knowledge. Even from my personal experiences, lots of things get documented when the person who knows them well is heading out of town and there's a sudden scramble to formalize that knowledge.

I'm exactly opposite, and had no problem taking PTO when I worked at a company with an unlimited plan. Now that I have limited PTO again I hoard it and take less time off.

I don't feel inconvenienced when others take PTO, and I don't expect my taking PTO to inconvenience them.

"Unlimited PTO" is a marketing farce, no more, no less. If you want people to take 25 days a year off, give them 25 days of PTO and be on the hook for the liability if they leave. If you want to give them more time than that through an approval process, offer it! But don't say it's unlimited, because it isn't. And if you don't want one of your business perks to be pointed out as fraudulent, don't advertise it as such.

A poorly codified policy is an implementation problem, and will be a problem for both limited and unlimited PTO policies.

> "Unlimited PTO" is a marketing farce, no more, no less. If you want people to take 25 days a year off, give them 25 days of PTO and be on the hook for the liability if they leave. If you want to give them more time than that through an approval process, offer it! But don't say it's unlimited, because it isn't. And if you don't want one of your business perks to be pointed out as fraudulent, don't advertise it as such.

The entire point is that the employer doesn't care how many days off people take each year. Employees can be responsible for deciding that for themselves. Some people don't want that extra responsibility, and I'd agree that they probably won't like unlimited PTO policies.

It would be ludicrous to outlaw unlimited PTO policies just because some people don't like them.

  The entire point is that the
  employer doesn't care how many
  days off people take each year.

I don't know how many times I need to repeat this, but if your company doesn't communicate expectation it's a problem with the company, not with unlimited PTO policies in general.

I also disagree that my comments haven't been helpful. There's a difference between the concept of "unlimited PTO" and any particular implementation of it, and it's important to know where a problem is coming from. Perhaps there should be regulations around it, but getting rid of it entirely, as suggested elsewhere in this thread, isn't the answer.

We wouldn't ban all cars because one brand is unsafe, so let's not get rid of all unlimited PTO policies just because some companies do it wrong.

Great observation! Statistically, there are more anecdotes in this thread with employees with negative experiences with good ones. I think that's a great starting point.

If I take one day off 30 times a year nobody raises an eyebrow, but if I take 30 days off in one go it might.

I can appreciate this opinion if you've had a good experience with an Unlimited PTO policy, but regulation isn't for the best experiences. Unlimited PTO is an HR/Marketing dark pattern.

EDIT: > It's disappointing so many people want to ruin things for everybody because they've worked at crappy companies in the past.

@jlarocco: I am disappointed you prioritize protecting your arrangement than the well being of others at crappy companies. As I mention in my other comments in-thread, you can still arrive at something similar to "Unlimited PTO" while still instituting regulations to prevent worker abuse (minimum PTO days issued + a process to request additional days). I do not understand the disdain for regulation that simply enforces what is being offered.

Say I booked the entirety of June off this year. Are they still cool with that? How about if I also decide I'd like July off too. That's an extreme I know but there's a limit somewhere.

FWIW we did have somebody take an entire month off to visit family in China. He was responsible for tons of code and functionality, and it worked fine because management knew about it and planned around it.

If you can't handle the responsibility, don't ruin it for everybody, just go work somewhere else.

In a strict PTO environment that would have been almost impossible for them to do.

Some people are going to respond and be upset that they want to work exactly 8 hours, get exactly 41.5 hours of PTA and get paid that way. That's fine, although I hope they are giving the company back money for browsing HN.

I on the other hand like the freedom and flexibility that unlimited PTO provides along with a flexible work schedule. Do I end up working more? Probably, but I have way less stress. I much prefer working that hour on a rainy Saturday instead of the beautifully sunny Friday.

Only ever worked at UK companies where we get 5.6 weeks PTO as standard. Never had a request denied as long as I've given 2 weeks notice of a long'un

If you requested your 5.6 weeks off all at once and over an go-live date that you were 100% responsible for, you might receive a request to see if you could move those holidays a bit later

Our European team colleagues? Not so much.

Current place I work has unlimited PTO, and I really like it. You do need to be careful not to fall into the trap of not using it, though.

Then there’s still normal vacation trips to consider.

I can easily see myself using 40 days of PTO in a year.

It seems to me like it would be fair for companies to offer unlimited PTO as long as employees can cash out unlimited money when they leave. But for some reason, this is not often offered.

As I mentioned upthread, I've never had a job where I didn't work when and how much I wanted, go into the office when I felt like it, etc etc. I'm subject to the same pressures you describe, but it turns out they're really easy to handle: keep a rough eye on how many hours you're working.

The other day they had a rare beer release I wanted to go to in the middle of the day, on a Friday. I didn't have any meetings, so I "WFH" and worked 3-4 hours that day and spent the rest of the day drinking and getting dinner with a couple funemployed friends, including checking my email and responding to important ones for a few minutes every couple hours during the workday. I could've (and have in the past) written off those four lost hours of work as coming out of my effective productivity, but since this is a new job and I'm trying to hit the ground running, I just made it up in dribbles of an hour or two over the next week.

The dirty secret when people talk about being pressured at work is that 90% of the time, your employers are relying on you to do the work of pressuring yourself. If my employer wants me to work extra and go above and beyond, I make sure that it's explicit and metaphorically "on the record". Pulling all-nighters during crunch time or forgoing vacation for a long time should be banked as something you can draw on, giving you cover for taking a longer vacation or working shorter days after crunch time.

It's really up to you to set your work life balance, and the fears most people have about the consequences of doing so are largely (but not entirely) illusory.

The one major caveat here that I haven't ever had to face is if you're both at an abusive company and highly replaceable (eg feel like you couldn't get a similar quality job). In this case of effectively having a better job than you'd otherwise get, the power dynamic is markedly shifted and employers can get away with a lot. The only saving grace in this situation is if your more in-demand coworkers have healthy attitudes about work/life balance, since it's hard for management to crack down on individuals in a way that's perceived as unfair.

There's ALWAYS a limit. Try taking a year long holiday and see how that goes. With UPTO the limit is up to your manager.

So even if you have a set number of days, your manager can still fire you for taking them. Your manager can fire you or not fire you for any reason. So you could take 30 days off and not get fired if your manager doesn't want to.

With "at will" employment there really aren't any concrete rules in play. Everything is just at the discretion of the employer. Regardless of the employee handbook, PTO or really anything. You could be fired for coming in too early. Coming in too late. Not working on the weekends. Working on the weekends. Probably even something as silly as gaining too much weight. Really anything unless it is within a few specific protected classes such as race or sex.

The only variable that exists is whether or not the terminated employee would qualify for unemployment benefits.

Edit: I should mention this is US specific as most US states have "at will" employment laws.

For doing something that is specified in the employment agreement? Pretty sure that would fall under fraud/misrepresentation.

What makes you think I haven't, are you saying that there is no fraud exception? You don't go into any detail to support your "absolute" confidence.

I'm mildly affected with Asperger's. There are many aspects of workplace culture that are obvious to other people, but which I take a long time to clue in regarding. This has included figuring out the reasonable boundaries for unlimited PTO in the past, especially when it required having to "read" my manager to figure out the acceptable timing and quantity of PTO.

My current employer strikes the perfect tone for me: they offer unlimited sick/family leave, but ask that we shoot for approximately N days of actual PTO per year. (Where N is clearly stated.)

There are two outcomes in that situation.

1. Great, so you've gotten Service Foo stable! It now needs minimal dev attention. Since there's no shortage of work that needs to be done, and you've got 3 days/week free, it sounds like you're free to work on Service Bar, in addition to Service Foo.

2. Great, so you've gotten Service Foo stable. Now that it needs half the development attention that it used to, we no longer need a full-time person on it. Since we don't have any more work, we're laying you off (Or, in a fairy tale, where, for whatever reason, your manager values your contributions for what they were, laying one of your co-workers off.)

Personally, I prefer outcome #1. I'm paid to be at work, and do things, and if I get my work done faster then estimated, I'll get more work. And that's fine. The alternative is much worse.

It's to the point where it reminds me of jobs that force you to dress up in a certain way: I can't imagine your workplace respects you if they're enforcing how you get your work done or what you're wearing.

I should be clear that there are situations in both cases where it can actually make sense: anyone working customers doesn't get to decide that customers are irrational for judging attire, so dress codes are reasonable in that case. Similarly, if your work heavily involves constant communication, then enforcing work hours can make sense too. But there are a TON of jobs that enforce rules like work hours and dress code for no reason other than lack of trust and respect for their employees, and I just hope I continue to avoid ever being in a position like that.

As you are saying that, as the business owner/manager you do the same, I think it shows a great example and helps people feel they actually can do this.

The opposite might also be very true, where if the manager is working harder than what is expected/accepted, people will follow and do the same too. Do you think that is true?

Regarding owners/managers working less, I see it the same as you: leading by example. And generally I don't see a problem with that, as everyone is mostly working very responsibly (in our case). However, what we've noticed over the years is that it still needs some people with a global company vision and also visionary mindset to push the company to new frontiers and help people to look beyond what they're currently working on and to think outside the box.

I think this is a serious risk for unlimited PTO. It's easy to miss, because well-meaning managers are least likely to notice the problem. Sure they were busy and came in all year, but they genuinely wanted their reports to take more time off!

In that sense, it almost has to be a responsibility at the management level; visibly booking time off and disconnecting is part of making a PTO policy usable for everyone else. Fortunately, it's the sort of responsibility that also helps keep management and founders from burning out or already being exhausted when crunches do hit.

From Let My People Go Surfing by Yvon Chouinard.

Morning slack message (which isn't the same thing as a standup): "Hey, I'm going to do X,Y,Z today but I'm also going to run a few errands after lunch so I'll be MIA from 12-2 CET but available after until 6 CET".

"Work when you want" doesn't have to mean "I have no idea when you'll be available today".

People confuse the two all the time! Flexibility and reliability have to go hand in hand, if you cannot be reliable when left unsupervised, you need to expect I cannot leave you unsupervised. On the plus side, when people are given this explanation they often self manage into a good routine.

The work-when-you-want is easily leading to a - show me the evidence on why I should trust you to have done something productive today.

It forces someone to just push for quick wins and avoid anything that is not leading to directly accountible results.

Here's a perfectly great update that didn't result in a quick win:

"I spent all day debugging that null pointer issue like we discussed. I thought maybe it was because the API was sending nulls across, but I looked at the logs and couldn't find any instance of that happening. I thought maybe it was a type coercion issue too, but I wrote a few tests to rule that out and it turned out not to be the case. Then I remembered reading about a memory corruption issue that sometimes happens in our runtime version, so I spent the rest of the day reading about the situations where that occurs and figuring out if it applies to us, but didn't get enough time to finish that up completely."

"This morning I sketched out three different possibilities for the new client check-in service. First draft of the spec is in progress, I expect to send it over to Jen and Andy tomorrow for their feedback."

"I made a dozen or so mockups for the new landing page. I have a couple more ideas I want to try out tomorrow, then I'll figure out what the best four or five are and show them to the team."

"Since we don't have any feature work pending right now, I've been experimenting on a branch with using $TOOL to do $THING better. It looks good because $X, although $Y might be a problem."

"We talked a while ago about doing $THING with the user's documents so they can $WHATEVER more easily, and I wasn't sure it was even possible. I've been looking into that today. It looks like there might be a way, so I'm continuing to investigate."

"We've wanted to replace $FRAMEWORK for a while now. I've identified the parts of it that we actually use, and I'm putting together a plan for what we can swap in and/or get rid of. It looks like, since we made $CHANGE last month, we can actually do most of it ourselves without much trouble."

If someone is lying, it will eventually come out. That fake report one day will turn into a week and eventually they will get fired. But, don't kill your entire team on the off chance that someone is trying to game the system.

The first one says they're writing a spec. Well, three days later, where's that spec? Next one is producing some designs, so same. Sure someone saying "$TOOL/$NEW_FUNCTION/$REPLACE_FRAMEWORK just didn't work out", could be cover for "I was playing Pac-man all day", but if you ask for details, BS should become clear pretty quickly.

And again, that's starting from the position that you think your teammates are probably slackers who would rather lie than work. Which is not really a great position to hold, IMO.

Look, if I'm leading a group like this, I'm going to have an idea of what your output is like in an average sense, both compared to your historical output and the group as a whole. If you blow off a day it's not really going to matter. (although I'd rather you tell me you needed to blow off a day than try and hide it, sure).

However, if you blow of enough days we're going to have a conversation about how your performance is dropping, and why, and discuss your ideas about how to turn that around. If it doesn't, we'll have another conversation, and so on. Eventually if none of this works we'll have a different conversation (about why you are leaving).

This doesn't actually have anything to do with reviewing daily/weekly reports. Those are for different things.

1) Take place in a typical corporate setting--which is the context here, nobody's asking studio musicians to do stand-ups.

2) Have 0 artifacts of progress being made. Even brand design goes through iterations.

3) Are so abstract that it's impossible to distill your thought process into a small summary each day

If it's really impossible to summarize what you did all day, I'm going to question if you were actually doing anything at all.

With one of my customers, I had a week when I consistently reported "designing the new model for $thing-that-drives-our-product", sometimes additionally with "and I spend some time talking with $product-guy and $coworker about the design". As a side effect of the design process, I produced a bunch of concept documents and drawings, which once the overall goal was clear, I transformed into barebones interactive prototypes testing experimentally some design points. So the next week, my daily reports were "aaand, I also did this prototype to test out $design-concern" (to which the universal reaction was "oooh, shiny! <3"). Two weeks, zero code for the actual product, just couple pages of text and a lot of garbage JavaScript in prototypes.

This is how work sometimes look. A good manager will accept your vague description, trusting that something of value commensurate with time spent will come out from the other end. As long as you actually deliver, a sane manager will not mind.

(That said, if asked for details, I always could explain what my main concerns and areas of exploration were at any point in the design process. The story about what you were doing is proportional to how much work you actually put in. If you can't elaborate beyond "I was thinking about $X", maybe you weren't really thinking about it? Conversely, I find forcing myself to write down and structure my thoughts to be an excellent way to unblock myself when my mind is running circles, or feels like watching Netflix instead.)

> As long as you actually deliver, a sane manager will not mind.

The problem is that these are very rare.

EDIT: If anything, the problem may be that the "bad manager" doesn't trust you. (Yes)

Maybe I'm lucky, but for all the failings of various people I've worked under, I've met none who wouldn't understand it when some work requires more cognitive effort than code.

If anything, the problem may be that the "bad manager" doesn't trust you. But that's a completely different issue than them not understanding the concept of abstract work.

And this is a terrible mindset.

> The work-when-you-want is easily leading to a - show me the evidence on why I should trust you to have done something productive today.

No, start from the stand point of trust.

> It forces someone to just push for quick wins and avoid anything that is not leading to directly accountible results.

It does force someone to think about results, but not necessarily quick. Even a result that takes months, has many steps along the way that can be communicated.

"work when you want" to me requires more than that. multiply your simple example to 2-4x a week, xN employees, that's a lot of noise

The two weekly stand-ups, one is actually work related (the team meeting) and people are encouraged to be there and not go surfing just during that specific hour and the other one is the MJ Weekly, where we just exchange personal and professional learnings for about 1 hour, which is a great way to get to know other people being a remote company.

That said, making those things "required" is not that bad compared to requiring people sitting 8 hours in an office. Again, my personal opinion.

However, it can still in my opinion work for a large amount of people. Anyone whose job has parts that can be done alone (programming, compiling reports, writing articles...) can benefit from a more relaxed schedule.