Before I start, I am not someone unusual. I am a software developer with a very normal 8:00-5:00 job and a very average salary. However, I don't spend very much money and I value my time very highly. Because of this, I have too much money and just want to have more time.

Does anyone have experience with this? I feel like asking for months of unpaid leave every year would probably be frowned on. Are there jobs where it isn't? What else can I do to exchange money for time? I'm mostly interested in very long breaks from work (like months long in order to travel) but also would take working fewer hours a week. Anyone have advice? I am willing to hear options that involve changing jobs. Also, I have not talked to anyone at my current job about it. Would talking to them be a good or bad idea?


Care to explain the downvote?

EDIT: I would really like to work something out with my current job or at least continue writing software. The ideal solution would involve staying here. It doesn't seem likely however so I am willing to consider solutions involving other professions.

  • 3
    The only more or less stable job (not freelancing) I know that can give you long streches of free time (month long vacation), relatively flexible hours in term of how many you choose to do by term and still good pay is university lecturer. I'd recommend you keep your frustration bottled up for a while and use your money to further your education until you're in a position to get such a job.
    – P. O.
    Jun 10 '14 at 12:35
  • 4
    I am interested in the answer, but I can explain the downvote: FAQs somewhere explain what good question is: likely to be relevant for others; objective (not opinions); "what job I should take" are explicitly forbidden. Yes, FAQs should be easier to be found. Jun 10 '14 at 12:58
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    @user22121 You want to have free time for a long period, if the company can miss you for that long, they might aswell fire you. I cannot think of any job except for being self-employed (you being the one in control of the work) or teachers that gives you that amount of free time.
    – Kevin
    Jun 10 '14 at 13:10
  • 4
    this is a great and very appropriate question in this age of overwork and employee burnouts, fueled by reinforced fears for survival. i am in the same boat but don't have an answer for you. as for the downvotes, i can tell you that haters gonna hate. they probably came from some overzealous type A slave drivers who are quick to put anyone who is not means to their end on some sort of a pole of shame as a slacker or what not
    – amphibient
    Jun 10 '14 at 15:25
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    Interesting reading: Wikipedia on Job sharing. Sweden had a system for a while where employees could take between 3 and 12 months off (while receiving some money from the government) while an unemployed person could temporarily take their job and get job experience. Finland has a similar system.
    – gerrit
    Jun 10 '14 at 20:33

I feel like asking for months of unpaid leave every year would probably be frowned on. Are there jobs where it isn't?


I have a friend in exactly the same position as you. He's single, has plenty of money in the bank, and likes to have significant, contiguous chunks of free time.

His solution - he is a contractor, and is able to find contracts that fit his need for time off, while balancing his need for income.

At one time, he took gigs where he worked hard in the spring, summer and fall, but took months off during the winter in order to travel the world skiing.

Then, he took gigs where he worked hard in the fall, winter, and spring, but took the entire summer off to sail.

If you work for yourself, and you are good enough at what you do, you can always dictate the terms that work best for your lifestyle.

And if you choose to take that path, you can approach your current company and see if they want to keep you around under your new terms. Perhaps they will agree, or perhaps you'll have to look for your gigs elsewhere.

  • 1
    Yeah, contracting can be a good idea if you're set up financially. I remember one contractor like you, he lived well below his means, but he'd work for 6-8 months, then take off with his canoe to Thailand for a couple of months. Last time I heard from him he decided to mix, by contracting in different countries as well, got lots of projects, some good, some bad, but easy to put the effort in and finish on a high when you know after that you can RnR on an exotic beach/see the world in general straight after (hmm I'm making myself jealous here, why did I stick as a permie again???) Jun 11 '14 at 12:03

Freelancing seems to be the logical answer here. As a freelancer, you can easily decide after a project ends that you'd like to tour the world for a couple of months. Theoretically, that is. In practice:

  • Even when you are between jobs, you will need to maintain your network, talk to people, call them, make pitches. Yes, you can do most of these on the road, using Skype from some remote Himalayan village. But you will probably not be able to just disappear from the scene for two months and expect to line up a new project in a short amount of time when you return from your travels because your money just ran out.

  • As a freelancer, you may not be able to take your time off when you want. Depending on your cash flow, you may need to immediately segue into the next project. Or you may end up with more free time than you bargained for, also known as "too few projects, too much time".

Basically, going the freelancer way may be the thing for you if you have a strong network and are recognized as an expert in your field. If there are clients calling you specifically, and if you can actually tell them to wait for four weeks while you recuperate on Hawaii and they actually wait for you, you are probably all set for this type of career.

  • An alternative would be emigrating. I assume you are based in the US. France and Germany have much more vacation time than the US. You would need to consider whether the trade-offs are worth it to you.

  • Or you could look at US subsidiaries of international firms. My employer has subsidiaries in the US, and the colleagues over there always complain that they don't know what to do with all their vacation time, which is almost at European levels.

  • EDIT: finally, there is the long-term approach. Slave away, don't spend any money, live extremely frugally - and then retire ridiculously early, possibly emigrating then to some low-cost country (Mexico?). The viability of this depends on your time preference.


I knew people that would spend half of the year working in North America, and the other half hanging around in South America. It worked for them because they:

  • Had very niche skills that were in demand
  • Were very good at their jobs
  • Worked as contractors

The job market is very much like any other market in that everything is a function of supply and demand. If you can make sure that you are very in demand then you will be able to dictate the terms of employment to some extent. Note, this does not necessarily mean that you will get to work with the newest and most exciting technologies. On the contrary, the people I knew were working with some archaic systems that were very hard to hire for in the first place.

Therefore, I suggest you find a useful niche and become expert at it. After you gain some experience, you can start contracting and built up a network of people you know to help you land jobs. Once you have both of those in place, you can start to get picky about employment and afford some breaks in between contracts.


Trick is to have well-paid very seasonal job. Tax accountant is one of them, used by few travelers which blogs I found. Another option is a job where skills churn is substantially less, like in healthcare, so you can get job after significant break.

It is more tricky for a software developer, because during "travel season", your developer's skill deteriorate, similar as when unemployed.


Your options are tied to the country you're living in and the different laws about working time in said country.

My answer works in France but it may work in your country too. Here you can ask to work less time per week, for less pay of course. Usually people ask to work 80% of the time, and the company usually has no problem with it (because they can't really do anything against it legally speaking).

I don't know the specifics of your situation, but I would suggest you see your HR department about working 80% for roughly 80% the pay. However be careful in your wording when asking if you think there's a chance this type of demand would be frowned upon.

  • Yep, I can confirm this. I work as a full stack web developer in France and I ask for 80% to my employer last week (so I can have more time to work on my side projects). Jun 10 '14 at 13:25
  • @AlexandreN. Does 80% necessarily mean 80% of the working week, or can one also ask (and get) 80% annually but work full weeks, with extended time off for months per year?
    – gerrit
    Jun 10 '14 at 18:12
  • @gerrit: The usual situation definitely is 4 days/week at work, with the 5th day spent with the kids at home (so a couple might need only 3 days of childcare per week)
    – MSalters
    Jun 10 '14 at 19:43
  • @gerrit. I have not witnessed 80% Annually. Most start up pretend to be flexible on work schedule so it may be worth trying. In most cases, you have 4days/week and as mentionned by MSalters, it's more common to ask this if you have kids. Jun 11 '14 at 7:57

There are ways to create sort of a "freelancing" type situation within a given company. This requires the ability to sell yourself and your plan, but if you want to be a freelancer, you better get use to this.

Your current company allows you to have a 9-5 normal workday which is very good for a programmer regardless of pay. Obviously, they are trying to create a sustainable work environment. Maybe you can convince them to shift your workload and focus more on projects. Example: Project "A" will take you 4 months working current hours. What if you could do it in 3? Would they let you off for 1 month?

Companies are trying to come up with perks all the time to keep employees happy/productive and you have a different case. I've worked at several companies that never allowed working remotely, but when I told them I was going to relocate, they thought it was better to keep me on remotely than find a replacement. And once, I asked to work from home 1-2 days a week several months before I decided to relocate and was emphatically turned down. I was surprised how quickly they said yes when I was going to leave for good.

Maybe working remotely with some flex-time, would be a better fit. Of course you won't get stretches of several weeks without working, but you can still travel.


Really it depends on what you are asking for and why. If you went to your company and said that you wanted to take an extra 2 months unpaid leave every year they would probably not be too happy.

On the other hand if you said to them that you wanted to take 3 months unpaid leave as a once off to travel the world they are likely to be more agreeable. There's no guarantee, but if you can organize things to the company so you take time out during a quiet period then a surprising number of companies will agree to it. After all the experience and motivation that you gain during that time will add value to the company when you return.

I was recently offered a contract where they wanted me to fill in for someone because he was taking 6 months out to go volunteer for a charity in Africa. In that case the company weren't just allowing the unpaid leave but willing to pay contractor rates to get someone in to replace him for that time!


If you want to continue with your current job and company, can you ask your boss if he/she is OK with you working, say, a 4-day week in return for 80% of your current salary? You have a 3-day weekend every week (equivalent to 50 extra vacation days), and the boss doesn't have to worry about you being gone on one long vacation.

Also, there are some companies in the software industry (Treehouse is one I can think of) that already have a 4-day workweek.

  • Any explanations for the downvote? I realize that the 4-day workweek solution was suggested in another answer, but my answer also has the suggestion of seeking out companies that already have a 4-day workweek (with an example provided). OP has already said they "would take working fewer hours a week", instead of long vacations.
    – Jay
    Jun 11 '14 at 17:59

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