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

Retirement is awesome and so is being so wealthy when it means you don’t need to work but have you considered jobs with summers off? It’s the best of both worlds! You can experience the freedom of not having to work (every year) with the security of a reliable paycheck. Sounds interesting? It is!

Should you change your job?

I worked hard to become wealthy quickly for my goals of being able to leave on adventures and have an amazing work-life balance. Some jobs come with adventure time and epic free time already have it built-in which riddles me with jealousy! Mainly jobs with summers off, or at least the possibility of long, frequent breaks.

FYI, I still kinda sorta work. I’ve created a sweet retirement 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 creating that job was hard work and if you don’t want to go through the effort jobs with summers off might be your ideal path.

Trends in jobs with summers off

I’m a big fan of breaking down the driving factors of everything. There are a million job descriptions out there but if you know the drivers you can access jobs yourself. There are two things you will notice something in common to all the jobs with jobs with summers off or large allowable breaks have:

  1. Unions.
  2. 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.

Does that mean teaching is easy? Hell no!

So let’s break down the individual field to help you find yours. 

Teaching – The gold stardard of jobs with summers off

Overall being in education can be a good deal for living a good lifestyle. The teens of today might not be the most fun to teach, but the perks make it worthwhile. 

  1. Standard education – All teachers get the same teachers college degree so they can swap around as needed. You could have a different teacher every month and life would go on. That’s awesome.
  2. Unions – If you are sick someone can take your place for months with little issue. 
  3. Summers off by default – You don’t have to put in any work to get summers off!
  4. Scalable hours – You can scale your hours around by picking up night, summer, or online classes
    Even better you can scale back easily. Most teachers unions, allow for preplanned YEARs OFF via a 4 years pay, over 5 years (called 4-over-5) system!


  • 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. 

Median salaries of educational jobs with summers off:

School Psychologists$65,000
Speech-Language Pathologists$65,000
College Professor$100,000


Pilots and flight attendants have some pretty great time-off allowances, and aren’t allowed to work too much by law. Plus they are often unionized and the whole aviation system is built upon epically long shifts.

You get serious flexibility in the shifts you take too. Work 1-day on, 1 day off and you choose your shifts at the start of each month. Heck, average pilots only work 20 hours per week!

Bonus – cheap flights! 


It’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 or starting a company, horrible for everything else.

Median salaries of aviation jobs:

Cabin Crew$40,000
Flight Engineer$75,000

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 loose your temp will be fine
  3. Many positions – If you have a job now, 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 government jobs to be jobs with summers off or any time of the year.


The main downside is that you can’t really excel in that system through effort. Promotions are a little more regulated.

Also painful, you’ll make less than you would elsewhere. But, why bother rising to the top or pushing yourself when you can get a life that’s 80% of the way to retirement all the time.


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



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, , therapists 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.
  2. Insane pay rate – All medical fields pay a lot! You can cut back your hours 50% 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.
    My family clinic has many doctors on rotation. Their long vacations have little effect on the operation of the clinic and I think it’s great.


Odd hours, 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.

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

Median salaries of medical jobs:

Dental Hygienists$70,000


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

What jobs give the most time off?

1 – Educational Jobs (Summers off):
– Secretary $40,000
– Librarian $55,000
– Teacher $60,000
– School Psychologists $65,000
– Speech-Language Pathologists $65,000
– Principle $90,000
– College Professor $100,000
2 – Aviation (20 hour weeks)
– Cabin Crew $40,000
– Flight Engineer $75,000
– Pilot $100,000
3 – Government Positions (Less pay, increased Flexibility)
– A government attorney will make $160,000 to the $300,000 of a private attorney.
4 – Medicine (Great pay, flexible shift work, ability to own practices)
– Dental Hygienists $70,000
– Dentist $125,000
– Physician $160,000
– Anesthesiologist $350,000
5 – Consultants (Your current job but hourly)
6 – Your job but negotiated better

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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