Boss doesn't seem to want to approve vacation time

Question

I have been working for a company for four years. Over that four years, I've taken about 8 days off - mostly sick days, a short two day break, and one small emergency.

I've also worked a lot of overtime - around 400 hours of overtime in the past 15 months.

At this point, I'm pretty tired. I went up to my boss, who is the owner of the (small company), and told her I needed some time off.

She agreed with me that I definitely needed a break and said that we would figure that out eventually, and she even brought it up a few times. As far as I can tell, she seems like she really likes the idea.

The only problem is... she doesn't appear able to deliver it. It's been about 4 months now since we initially had the discussion, and I'm getting more and more burnt out - especially because we had to push a major project out recently and I ended up working a bunch of additional hours on it - probably about 40 hours or so total overtime.

She recently seemed excited that I was going to get a day off for Christmas, and acted as if that would be enough to raise my spirits and energize me, but if she thinks that's enough to do it, she's off by about an order of magnitude.

How do I adequately express to my boss that I am absolutely exhausted, and that if this issue persists, I'll likely look for greener pastures elsewhere? This is a major problem affecting my productivity and I'm starting to feel it is affecting my health, and I don't feel it is being given the seriousness it deserves.

Is this a malicious (sees me as someone to be used) thing, or just an incompetence/lack of awareness thing?

For background of the company, I am the only employee and do most of the directly billable work (my boss can do it but typically does other stuff)

Per request, here's some information:

1) Located in the United States

2) Number of days of vacation allotted in my contract are 15

3) This was all unpaid overtime

Answer 1

You taking time off is an idea that your boss thinks is great in theory, but in practice she is never going to suggest you take a particular day or week off. You will need to suggest it. I don't recommend demanding as a first strategy.

Look back over the last year. Is there a pattern of lulls? For example, after a major project is pushed out? After a year end, quarter end, or other predictable date? If there is, you can suggest you take a specific week off based on your observations. If there isn't, then just arbitrarily pick a week. It should probably be at least a month from now unless it's "next week" and you have reason to believe that can work.

Next, make a plan for how the company can keep running while you're away. This might mean that some people contact the boss instead of you. It might mean they get told to wait (my firm is so small now that we just say "sorry, unless it's worth calling someone who literally is up to their waist in warm water, it will have to wait." And in 2015 the love of my life did solve a huge sysadmin problem by remoting back from a tropical pool.) Decide how to communicate the plan to others.

Finally, and this is important, take the time off. You don't have to book a trip - sleeping in, tidying your home, catching up on shopping etc are all good uses for your first time off in a long time. But don't check your email or take a quick look at the server to make sure everything's stable. You need to prove that you can have time off. If someone contacts you in a panic, it's ok to solve their problems - knowing they can reach you is part of proving you can have time off. But you need to get work out of your head for a while so you can rest.

Now, to back up a few steps, what if your boss said no, that week will not work because [whatever.] You do not say "ok, thanks, talk to you later." You say "what week should we choose instead?" And the two of you work out a week that will work. If need be, you remind the boss how important it is for you to get some time away. If you are getting clear signals that the conversation has to end now, even though no week has been chosen, say something like "we have to come back to this in the next few days because I need to book some tickets." Then in a day or so, bring it up again.

If you have tried several times to work out a week that would be great and no week would be great, you can try the Bill Mason strategy of simply announcing when you are leaving and for how long. You tell the boss that it is up to them whether you are quitting or on vacation, and that you are ok with finding out which it was when you try to return. If you are amazingly great, and you really need the time off, you will find that you don't much care which it is; if you're not working there when you come back, you can work somewhere else. (Be nice: don't say "next week" if you pull this stunt, say "6 weeks from now", and don't take 4 months off with this technique.)

Where things get really awful is when the boss always has reasons why a particular week won't work, and you are no longer confident (partly because of burnout) that you could land another job if you just took time off. In that case probably your only hope is landing the other job first, establishing that people in that company take vacations regularly, and then giving your notice at the first place and telling them it was because they wouldn't let you take vacation. Let's hope it doesn't come to that.

Answer 2

Obviously, your boss is not making your need for a break a priority. Frankly, your need for a break is neither a priority with her nor does she feel that it rates a high degree of urgency either. You are probably going to have to turn on the charm and deliver the boot up her ass/wake up call that will motivate her to see your need for a break as both a priority and as an urgent matter. Will that boot up the ass have to be an announcement from you that you've found another job? Perhaps. Or it could be a unilateral announcement from you that you are taking a break and if the world as she knows it ends on that day, that's just too bad.

Your business is as busy as hell. This means that if she is going to let you take a break, she is going to have to make EXPLICIT arrangements to have someone take over from you on a temporary basis while you are gone. She is devoting her full energies to making money and it seems that she has not made any effort to make arrangements to keep her office running so that you can go on your break. Her pleading that she does not have/did not have the time to make those arrangements should cut no ice with you: if something is important enough, people will make the time and the effort.

You can unilaterally TELL her that you are taking a break on such and such a date for a week or two weeks and that your taking a break after all these years is a non-negotiable item. It's not a request on your part, it's more like an offer she can't refuse. Call it shock therapy - you'll get away with it if she feels that she doesn't want to replace you with somebody who is more likely to be less motivated and who is more likely to be less productive. And that she feels that your break was a long time coming and she really owes you one.

Your boss seems to be a nice enough lady, but it's time for her to deliver on her promise to give you a break. Her being well intentioned is simply not good enough - Louis XVI had plenty of good intentions but we all know how that movie ended.

Answer 3

How do I adequately express to my boss that I am absolutely exhausted, and that if this issue persists, I'll likely look for greener pastures elsewhere?

In some tiny companies like yours, this happens.

You find a quiet time to talk with your boss. You say something like "Boss, I'm feeling absolutely exhausted. And if I can't get the time off that is due, I'm afraid I'll have to start looking for a new job." You'll have to say it and mean it. Don't wait 4 months again to act on it.

And if necessary, you start looking for a new job, get and accept an offer, then give your notice.

While you are looking for your next job, ask about the overtime required. If the overtime you are working is enough to make you want to leave, then you must be clear about how much overtime will be expected, and reject the job if necessary.

You might also seek companies where you aren't the sole employee, and where your absence during vacations won't be so significant.

[Now you are saying you worked 400 hours of overtime. It doesn't matter - the advice stands. Ask for whatever time off you feel you need. If you don't get it find a new job that won't require more hours that you feel you want to spend. And don't be the only employee this time.]

Answer 4

Write a formal request for Time off. Specify the number of days and when. Do this a few weeks in advance. If you have a formal policy follow it, if not then a professionally written email asking for the request.

If approved, make your plans, and don't sweat the deadlines.

You also need to stop all the overtime, I hope it's paid overtime since these are billable hours. If you have a say in the planning process improve your estimating based on your past experiences, if you do not, the politely inform your boss/owner that you cannot work the extra time and she should have budgeted more time in the schedule, especially based on past time overruns.

Lastly, take some of that time off and get a new job. You are right in saying you are burning out. You can't keep this kind of pace up. When looking at new jobs probe carefully about working hours. My go to question when interviewers ask if I have any questions is "Tell me about a typical day/week". If you ask this of the regular employee interviewee vs. a manager you often get a fairly candid answer about how much work they do in a week.

If you get denied or the vacation time gets pulled, ramp up that job search. You don't owe these people anything, they have been using you.

Answer 5

Have you been documenting your overtime? With time sheets or some spreadsheet? It is quite possible that your boss is ignorant of the scale of overtime that you've worked. It is also possible that your boss doesn't care. Documentation to show the extent would be essential in any negotiations. Learning the difference is important in future negotiations. If you get docked when you stay home sick, then you're really hourly and not salaried. Documentation of actual time-to-completion would be helpful for a company to accurately bid for work in the future.

my boss, who is the owner

It is normal for such a person to work lots of overtime themselves - because the company is their own property. It is common for them to avoid vacation because the company is "their baby". It is unreasonable for you to work that much unless you have some equity in the company (such as stock options). Expect lots of guilt to come your way when you quit, don't let her take your red stapler.

How do I adequately express to my boss that I am absolutely exhausted, and that if this issue persists, I'll likely look for greener pastures elsewhere?

Looking at some of your other questions, you are burned out and have been for a while. I reached this point with one boss and on my way out to my car, a coworker talked me out of quitting. I had scheduled a week to help a friend and had scheduled time off at work which was rescinded at the last minute. My remark to my boss as I walked out the door was that I was going to take that "staycation" and if I had a job or not when I came back that would suit me just fine. I quit that job later that year.

One thing that can help reduce burn-out is vacation time, which you are working on now. Another that can help is physical exercise. I found that scheduling gym time was beneficial to mark the end of the day (I was working remotely from home) as it gave me a scheduled end. My personal preference were group dance classes (Zumba and U-Jam) and group exercise classes (yoga and BodyFlow) at the gym as they were not things that one could "just do an hour later" (higher impact exercise damaged my knee joints). Lots of people have exercise as a New Year's resolution, this would be a good time to insert it into your schedule if you can find something near where you work/live. Another advantage of exercise around 6-7pm is that if they want you to work late, offer to come back after the exercise class, I've found that they don't ask repeatedly.

Another thing to do is start looking for work elsewhere. Do not fall into the trap of thinking that you have to save your boss, nor your company. They will live without you. If your locale has limited software development opportunities, you may have to move. If that is the case, being debt free will vastly improve your ability to move to a better "neighborhood".

Answer 6

You may have to approach this situation on a couple of different fronts:

1. You're going to have to learn to say "NO", and get yourself a life outside of work, and set better boundaries. Specifically, this is in relationship to working all that overtime. The stress levels in your body from excessive hours produce hormones that aren't designed to be present all the time, and this will catch up with you eventually in the worst way. Ultimately, it doesn't matter that you're the only person around who can do the work beside your boss. If there's that much work to do, the company needs to expand the staff accordingly. If you dropped dead today, the company would be in the same situation! Stop making and accepting excuses for the company being short staffed. You might use some counseling or coaching on how to be more assertive.

2. You have to decide how much leverage you have in this situation if you're going to do as others have suggested and simply announce that you're going on vacation on such-and-such a date. Obviously, it's not in your boss's benefit to authorize a vacation explicitly, but if you take authority on this situation, you may come back to no job at all. So you need to know that either (a) you're that critical to the operation that replacing you within the span of your vacation would be extremely difficult, OR (b) you are sitting on five digits in the bank so you don't have to worry about it.

3. Know your worth. Do an assessment of your skills and what the market would pay for them. STRONGLY consider finding yourself a better 9-to-5 home-away-from-home that offers a much healthier work-life balance. Do your homework so you don't end up in the same situation.

Answer 7

Don't ask, tell

You need to decide for yourself if this is the right approach with your boss at this moment, but have you considered telling her you're taking time off instead of asking?

Aim for a win-win

Ideally don't take two weeks off the first time out; go for a week (of course if you need more for your mental health, then by all means take what you need). Ideally work with your boss to come up with a plan to help the company run smoothly while you're out, but I realize you may not have the mental and emotional resources left to do this due to burnout. If that's the case, it's on your boss at this point to work it out. If the company will go under if you take a week off, the company may not survive no matter what you do.

You need to take care of your health!

Negotiate the dates, not the vacation

Don't budge on the time off, just the dates. And don't give up on your suggested dates without firm dates from your boss. Don't accept "you can take off when we reach milestone X" or "we'll reconsider in 6 months".

Don't let your boss ruin your health

It's not worth it. Either take a vacation or look for another job. I know it feels like you can't leave when you're in it, but that's not true. Burnout destroys relationships and puts people in the hospital (or worse).