Jobs with summers off: These jobs might be right for you!

Hey, early retirement is awesome and all but have you considered jobs with summers off. That way you can experience the freedom of not having to work (for a couple of months) with the security of a reliable paycheck. Sound interesting? It is!

Should you change your job?

My own goals behind my financial independence are all centered around freedom and a work-life balance, but some jobs already have it built-in which riddles me with jealousy! Mainly jobs with summers off, or at least the possibility of long breaks.

No, I’m not planning on starting a new career path at this point, but I bet some people out there wouldn’t be so opposed to it. 

FYI, I still kinda sorta work. I’ve created a sweet job for myself that gives me the freedom I was looking for while keeping the perks of having a job – and there are many perks. (More on this at end of the article.)

But if you don’t want to go through the effort that I went through to create that sweet job, maybe this is your ideal path. If you’re considering changing your career path anyway, why not start by looking at jobs with summers off. 

I’m going to break this down to a pretty rough level because there are a million job descriptions out there. You will notice something in common though. Jobs with summers off or large allowable breaks have:

  • Unions.
  • Standardized certifications/education. 

Teachers, for example, have both of those. In a given state all teachers went to teachers college and passed the certification which makes them essentially swappable if one decides to leave. Then since they are in a union they can’t be prosecuted for using their super work-life balance opportunities.

Do I think teaching is easy? Hell no! (But I can’t help but look at the perks.) 

So let’s start with the most obvious one. 

Teaching – The gold stardard of jobs with summers off

Overall being in education can be a good deal for living a good lifestyle. I wouldn’t want to teach most of the teens of today to be honest, but the perks make it attractive. 

  1. Standard education – All teachers get the same certifications so they can swap around as needed. You could have a different summer school teacher for a given course every year and life would go on as normal. That’s awesome.
  2. Unions – If you are sick someone can take your place for months with little issue. 
  3. Lots of time off – You get months off as a standard layout. There is a union so likely no one will really get on your case either for not putting in long hours or having a few more sick days than normal.
  4. Scale hours up and down – The pay rate is decent and you can scale your hours around by picking up night school/summer/online school if you want some extra hours.
    Even better you can scale back aggressively. Teachers, where we live, can take entire years off if it’s planned ahead. It’s almost impossible to beat that.


  • If you get stressed easily when people push your buttons, the kids will destroy you. (Teenagers are nuts these days! Back in my day…) 
  • Climbing the ladder and becoming a principal or a college professor would make you lose most of the sweet perks. So if you’re ambitious to rise in the ranks, go elsewhere.
    • A principle is technically one of the jobs with summers off but that’s when they do their hiring. Hmmmmm.

Maybe just start by teaching your kids about money

And you don’t have to be a teacher to work in education. 

Other education jobs with summers off:

  • Secretary $40K
  • Teacher $60K
  • Principal – $120K Principals do hiring in the summer but you still get time off.
  • College professor – $100K Although 4 month summers are when professors seem to get all their research done. Professorship sounds fun but likely isn’t.


Pilots and flight attendants have some pretty great time-off allowances. Plus they are often (always?) unionized and the whole aviation system is built upon epically long shifts.

These aren’t really jobs with summers off but they get serious flexibility in the shifts they take.

Work 1-day on, 1 day off and you choose your shifts at the start of each month (I’m sure there are limitations to this, but I like looking at the upside!) 

Bonus – cheap flights! 


Pay isn’t great (pilots only make $60K and that’s a damn hard job to get) and you get stranded in strange places for days at a time with no pay. Perfect for blogging horrible for everything else 😛


Government – Jobs with summers off. Or anytime off!

Government jobs have 3 amazing things going for them. 

  1. Unions – Being in a union usually means you are allowed to swap places with a co-worker fairly easily. Oh #245 is on a 1 month vacation? Bring in #276.
  2. Bloat – Governments aren’t usually the most efficient places around. There are too many rules. This goes really nicely with the union setup to make it possible to take long vacations. If your deadlines are strict or tight your temporary replacement can figure it out.
  3. Many positions – If you have a job there is probably a government equivalent of your role. Oh, you are tired of cramming out endless marketing campaigns? Well guess what, your local government has a graphic designer job and you’d be a great fit!

Together these things allow goverment jobs to be jobs with summers off. Although really you could bugger off at any time of the year. That’s even more flexible!


The main downside is that you can’t really excel in that system very easily and you’ll make less than you would elsewhere. The jobs aren’t easy either. You just have more ability to bugger off than say a Project Manager in silicon valley.

But, why bother rising to the top or pushing yourself when you can get a life that’s 80% of the way to retirement right away. Go with the flow and live easy.

  • Government Attorney V – $160K
  • Private Attorney V – $300K

Another obvious downside: It seems boring. Read a book?


Medical Fields

Medicine isn’t exactly an easy field to hop into but once you make it, there are 3 special features.

Disclaimer: I’m referring to Dental Hygienists, Dentists, Physiotherapists, Psychiatrists, surgeons, and family doctors, etc. All the medicine.

  1. Standard education – There are many types of doctors, but in a given field they do all get the same certifications. (If all medicine at a hospital had to stop because Bob broke his arm, that would be a problem.)
    For example, if you want a lot of time off. Be a locum tenens and cover for other doctors who are away for whatever reason. Thanks to standard certifications.
  2. Insane pay rate – All medical fields pay a lot! You can cut back your hours and still have a higher income than most people. 
  3. Owned practices – This isn’t true for everyone in medicine but if you can own your own practice you get more say over your own hours.
    The family clinic I go to has many doctors on rotation. If the partners are ok with it, long vacations have little effect on the operation of the clinic.


So much school and so much debt. You don’t really have the option to use these perks until you’ve worked for 5-10 years to pay off that incredible debt pile you’ve built up.

And read this student loan refinancing guide to clean that debt up!


I can consult. You can consult. Everyone can consult! 

What’s consulting? Well, you can just do the same job you do now for a given company or you can advise them. You have some control over how much you work, but there are no guarantees on how many hours you can get.

So… Great? 


  1. It’s the same job you already do
  2. You might get paid more for it (while losing other perks.) 
  3. Anyone can do it


  • The amount of hours you’ll work is unknown. So you might be getting “involuntary” vacation time. 
  • Drumming up clients is a grind.

To be honest I think the next option beats consulting by a long shot. So moving on!


Your current job – The best of jobs with summers off

I won’t harp on the details, because I’ve written extensively about this before, but there are ways to make your current job your dream job. Including making it one of the jobs with summers off. So just come read about how to make your job a great retirement job

Leave me a comment – are you thinking of switching careers and what do you think of my list? (And are you willing to make YOUR job a retirement job?)

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