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10 Enjoyable Side Jobs After Early Retirement


side jobs after retirement

Retirement doesn’t mean you have to stop working completely. In fact, I think a little work is good for your soul. This is especially true for early retirement. I’m 43 years old and I don’t want to watch TV and play video games all day. That would be relaxing for a day or two, but I’d be very dissatisfied with life over the long term. It’s not good for your physical or mental health to shut down that much when you’re young. As long as I’m relatively healthy, I’d like to keep working part time on my own terms. I’m sure most retirees would have a better quality of life with this mentality. Today, I’m going to share 10 enjoyable side jobs after early retirement. I hope you enjoy the list and share your side hustle idea in the comment section below.

Work is good

Work by itself isn’t bad. It’s just all the BS that comes along with it that makes the majority of U.S. workers dissatisfied with their jobs. The great thing about financial independence is that you can work on anything you want. Imagine having a fun and enjoyable job that is devoid of BS. Wouldn’t that be the life? What are some ingredients that help make work enjoyable? Here is my take.

  • Flexible schedule – Employers are demanding way too much from their workers today. A lot of people feel like they are on the clock all the time. Work would be much more enjoyable if you can work when you want.
  • NO traffic jam! – This one is my pet peeves. I can’t stand the rush hour traffic jam. It turns me into an angry person. The ideal work situation for me is to work from home or very close to home.
  • Intellectually stimulating – When you’re learning something interesting, it doesn’t feel like work. This is really important for retirees because human brains stagnate with no stimulation. It’s never too early to start protecting your brain power.
  • Success – Personally, I think you need to see some success from your side jobs. It’s got to change lives, make money, produce something cool, or help you feel good about yourself. If you’re not successful, then the work would eventually become dissatisfying. Everyone has their own definition of success so this one is very broad.
  • Social interaction – Social connection is the thing retirees miss the most about work. Early retirement can be a lonely journey if you let it because all your friends are probably still working. A side job can help alleviate that by adding new social connections.
  • No micromanagement – Actually, I prefer no management at all. I never want another boss again. That might not be realistic for everyone, though. Most people probably will be pretty happy with no micromanagement.

Okay, that’s enough stalling. Let’s get to those enjoyable side jobs.

Enjoyable Side Jobs After Early retirement

1. Blogging!

This is number 1 for me because I’m having some success at it. Blogging fulfills every one of the requirements above. I can work on my blog whenever and wherever I want. Usually, I work from home or go the library so I don’t have to deal with rush hours traffic. Writing a blog post takes a lot of research so I learn something new all the time. Interacting with readers and other bloggers is a lot of fun too. Lastly, no boss! It’s a perfect side job for after retirement if you can become successful at it. Starting a blog is easy and anyone can do it. See my tutorial on How to Start Blogging if you needs help. It takes a lot of effort in the beginning, but it can be really enjoyable, too.

Check out Frugal Asian Finance. She only started a few months ago, but she threw herself into it. I think her blog is great and it’s going to be a big success.

Making podcasts and YouTube videos count here as well. I don’t know much about these side gigs, but it’s the same idea as blogging.

2. Pet sitting and dog walking

If you like pets, then this would be a great side job. Everyone is so busy these days and they need help with their pets. Once you’ve got a good reputation, you can charge quite a bit for a pet sitting gig. I think the going rate is $30/day or something like that. This can grow into a bigger operation if you have the space. Dog boarding and doggy daycare are thriving businesses. In 2016, U.S. pet owners spent over $60 billion on their furry friends. That’s pretty crazy to me, but it’s true. (You can end world hunger with that kind of money…)

3. House sitting

If I was a single early retiree, I’d become a house sitter. I could travel the world and get paid to stay in someone’s home. This sounds awesome to me. One of my friends is a professional house-sitter and I’m a little jealous. She gave up her apartment and has very low cost of living. Our former tenant also house sit and she’s been to many U.S. cities since she left Portland 2 years ago.

You’d have to be good with pets, though. It seems most home owners are worried about their pets and plants while they’re on vacation.

4. Wood working

I think wood working would be a lot of fun. Our dining table is wearing down and I can’t find an affordable one I like. I’m done with laminate tables and I’d like a nice solid hardwood table that will last forever. Of course, an “artisan” table costs a ridiculous amount. Here is a nice table from a local shop that I like. It costs $3,705! That’s a bit too expensive for me. I might as well artisan it myself. Someday…


5. Personal coaching, tutoring, and teaching lessons

This one would be good if you like helping others. Some personal finance bloggers have a coaching business on the side and I think it’s a great idea. You can share your knowledge and help others with their finance. It’s a win-win situation.

This one works very well for kids too. You can teach piano, coach soccer, or do whatever you’re good at. I’m not sure if I can do this one, though. Mrs. RB40 thinks I’m a terrible teacher because I’m a bit impatient.

6. Yoga or Tai Chi instructors

I have no idea about the logistic for this one. I just think it would be a lot of fun. Yoga and tai chi are great moving meditation exercises. They help calm the mind reduce stress. It’s too bad I haven’t done them in a while.

Here is an old guest post from my old Yoga instructor – Do What You Love.

7. Host tourists

If you enjoy interacting with visitors, then hosting tourists might be a great side gig. This is easy now with AirBnb. You can rent out a room to tourists and tell them about your town. Mrs. RB40 dreams about running a small bed & breakfast. That would be cool too, but probably involve a lot of work. It’d be ideal if we could get a property in Hawaii for that.

Being a campground host sounds good too. You don’t get paid, but the stay is free. The Forest Service is always looking for campground hosts.

8. Drone pilot

I recently heard that you can get paid for this. You can use the drone to take pictures for real estate agencies, make movies, deliver packages, or even enter in a race for prize money. To become a legitimate drone pilot, you’d need to pass a test to get a drone pilot license from the FAA.

9. Artist

Retired early? Here is your chance to become an artist. You can paint, sculpt, build huge hanging mobile installations, start a band, or whatever you want. The possibilities are limitless. It’s probably pretty tough to make money as an artist. This one is more like a hobby unless you have some talent.

10. Busking

Busking might be fun if you don’t need the money and you enjoy performing. I don’t know how much money you’d make, though. Probably not much unless you live in a metro area with a lot of foot traffic. My 14 year-old cousin raised $2,000 for Doctors Without Borders with her violin. That’s a very impressive accomplishment.

What’s your dream side job?

So that’s my list of enjoyable side jobs post early retirement. What do you think? Have you considered any of the side jobs above? I’m sure there are many more enjoyable side jobs out there. Money wouldn’t be a big consideration assuming you’ve reached FI. You’ll have to freedom to try different gigs out and see what you really enjoy. Wouldn’t that be great?

What would you like to work on if you don’t have to worry about money?


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Joe started Retire by 40 in 2010 to figure out how to retire early. He spent 16 years working in computer design and enjoyed the technical work immensely. However, he hated the corporate BS. He left his engineering career behind to become a stay-at-home dad/blogger at 38. At Retire by 40, Joe focuses on financial independence, early retirement, investing, saving, and passive income.

For 2018, Joe plans to diversify his passive income by investing in US heartland real estate through RealtyShares. He has 3 rental units in Portland and he believes the local market is getting overpriced.

Joe highly recommends Personal Capital for DIY investors. He logs on to Personal Capital almost daily to check his cash flow and net worth. They have many useful tools that will help every investor analyze their portfolio and plan for retirement.

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{ 59 comments… add one }
  • Michael @ Financially Alert August 31, 2017, 2:23 am

    I think you nailed it, Joe! Working after financial freedom is a primary key to staying happy. Doing something because you love it vs. having to do it makes all the difference.

    I’m into my 4th year of early retirement and love having the flexibility to try different hats on. I guess I love variety.

    I love being a stay-at-home Dad currently, coaching, and blogging in my spare time. It helps give me a sense of purpose and contribution that’s super important to have after you pack away the traditional 9-5.

    • retirebyforty August 31, 2017, 10:47 am

      It sounds like you have a full plate. That’s great. Being able to choose your own work makes a huge difference.

  • Ember @ An Intentional Lifestyle August 31, 2017, 3:23 am

    I’ve been thinking about this lately because my parents are trying to get to semi retirement.

    Definitely agree w the guidelines you out. None of that would be fun.

    I’d love to be a server part-time, but I know that isn’t flexible which is the whole point.

    Blogging, of course, and the hosting. Both of those would be my favorite. I love having people over, and that would be so much fun! Now, we just need somewhere to put them….

    • retirebyforty August 31, 2017, 10:49 am

      Server in a restaurant? That’s hard work. I worked in my parent’s restaurant when I was young and it’s not that much fun.

  • [email protected] August 31, 2017, 3:43 am

    Great ideas Joe! And patience is pretty important if you are going to be a teacher 😉 Now that I’ve just retired early, I will be looking at different opportunities. What I’m most interested in is coaching/consulting and helping people with major life decisions. (Sometimes people confuse this with counseling – which is totally different though!) I’ve worked with four clients so far and loved it! I just need to figure out the business part and getting my services out to potential clients. But that’s what I need to learn – which is something I enjoy doing too! We are going to look into house sitting/campground hosting too in the next few years.

    • retirebyforty August 31, 2017, 10:50 am

      Right. I know I’m not patient enough to tutor others. Why can’t you get this concept? It’s so easy. 🙂
      Great job finding something you like to do. I’m not quite ready for coaching yet, but maybe someday. That should be easier than tutoring. They already know what to do and just need a nudge. I’m assuming. Good luck!

  • Mustard Seed Money August 31, 2017, 3:47 am

    My dream job would be to financial coaching. I think being able to make an impact in people’s lives would be super fun. Plus getting to share something I’m so passionate about would be wonderful 🙂 Plus it wouldn’t feel like work to me since I’d do it for free.

    • Mr. Freaky Frugal August 31, 2017, 5:25 am

      I’m with ya – I’d love to financially coach other people. I did do it with my adult sons and it’s fun to watch them apply what they learned.

      But the next best thing is writing a personal finance blog that hopefully helps others. 🙂

    • retirebyforty August 31, 2017, 10:51 am

      That’s great. It’s something you can work on. I’d like to try coaching someday too.

  • B August 31, 2017, 4:07 am

    Contributing back to the community by helping someone achieve their dream would be another stepstone and motivation for some people.

  • Brad - MaximizeYourMoney.com August 31, 2017, 4:52 am

    My father used to do a ton of side-hustles. He did chimney-sweeping, custom framing, log splitting, and a half dozen other ventures. He liked to keep busy and he had no hesitation about “just doing” something. If he had interest in it, he started doing it. No huge business plan or funding or anything… just hustle. Ah, the good ole days. 🙂

    • retirebyforty August 31, 2017, 10:52 am

      That’s great! Your dad sounds like a real go-getter. You learn by doing, right?

  • Erik at Hippies de Land Rover August 31, 2017, 4:54 am

    You’re right Joe!.
    Working is healthy for mind and soul.. even for money hehe
    Teaching young generations about personal finance is a MUST work someone should do.
    This is something I’ll start on once we retire by 2019 🙂


    • retirebyforty August 31, 2017, 10:53 am

      That’s a great idea. I was thinking coaching would be a good fit for people who needs help with their finance, but it would be great for kids too. We’d need to get them interested first, though.

  • Nick Frijters August 31, 2017, 5:02 am

    I believe that there is a thin line between people who like to blog and people who like to coach. Myself, I like (love? starting to like more and more…) both! I’ve recently started blogging actively – but I’ve been a Scrum Master professionally for some time now, allowing me to focus on helping people, in one way or another. If I’m ever so lucky to retire early, I will definitely keep on coaching people.

  • Ms. Frugal Asian Finance August 31, 2017, 5:04 am

    Did Joe just mention me in his post? Yay!!! I’m so happy. Thank you, Joe! I have to double-check the name of the blog to make sure it’s mine. I feel like today is Christmas Eve already! *happy dance*

    I think your list is awesome! I would love to try everything you mentioned above when I retire (besides blogging because I’m already doing it). My MIL does Tai chi too, so maybe I will try to learn some moves from her. 😀

    • retirebyforty August 31, 2017, 10:56 am

      You’re welcome. You’re doing great with your site. I’m very impressed how far you’ve come in just a few months. Much better start that I had. Enjoy your Tai Chi lesson. 🙂

  • FullTimeFinance August 31, 2017, 5:17 am

    Am I the only one who doesn’t know what busking is?

    You do make great points though. Work and productivity is our nature. Some sort of hustle or volunteering can be part of your life no matter what stage your in.

    • Solitary Diner August 31, 2017, 8:24 am

      Busking is performing in public (e.g. on a street corner, in a subway station) in exchange for tips. It’s often musicians, but it can also be magicians/actors/clowns/etc.

  • Mr. FWP August 31, 2017, 5:31 am

    Great ideas, Joe. I really like, though, how you’re illustrating that retirement isn’t what most people think, where you sit around or vacation all day or whatever. You can still do things for others, find value, and do things that have purpose and meaning. There’s nothing wrong with taking off – to be clear – but your piece illustrates that there are excellent alternatives to the American popular culture idea of “retirement.”

    To answer your question, I’d love to do financial planning, coaching, equipping people in various ways, perhaps some teaching, and that kind of thing. Those would all be a blast. And I’m already doing a number of those things.

    • retirebyforty August 31, 2017, 10:57 am

      Exactly! Being in vacation mode all the time isn’t much fun. It gets boring after a while. We should stay active and involved while we can. Relaxing all day can wait until we can’t work much anymore.

  • Mrs. Groovy August 31, 2017, 5:53 am

    Doing something you enjoy for money, and knowing you don’t HAVE to do it, can be awesome fun. I don’t know yet whether Mr. G or I will take the plunge but it probably won’t be with blogging. For me it’s already begun to feel like a chore (hence, I’m not writing very much) and I can’t imagine taking steps we HAVE to take, in order to make money (since we don’t need the money).

    Do you know the store Woodcraft? They offer some reasonable classes/workshops where they supply the tools.

    • retirebyforty August 31, 2017, 10:58 am

      Blogging is a lot of fun in the beginning, but it’s hard to stay engaged once it becomes routine.
      I’ll check out Woodcraft. Thanks!

  • Budget on a Stick August 31, 2017, 5:54 am

    HA I actually wrote about this not to long ago. I want to job jump!!!

    I love to try new things so when I retire I want to just search for different jobs and see what they are like. Sort of like Mike Rowe on Dirty Jobs.

    • retirebyforty August 31, 2017, 11:00 am

      I like your idea, but many of those jobs would involve a boss… Maybe it’d be fun to try for a few months and then go the self employment route if it’s fun. I’ve only seen a few episodes of Dirty Jobs and I didn’t like any of those jobs. 🙂

  • Dads Dollars Debts August 31, 2017, 6:24 am

    I think I would enjoy teaching kung fu/tai chi. I have been doing kung fu in some form for the last 4 years and can not speak highly enough for the benefits on my body. Better posture and flexibility, less joint pain, and I can kick A$$…well I am not sure about that last bit as I try not to fight.

    Oh, side gig #11, get someone to pay you $30 million to get in the boxing ring and get hit once or twice…I would do that for sure.

    • retirebyforty August 31, 2017, 11:01 am

      Great! I’d like to get back into Tai Chi and Yoga someday. Life is just too busy right now with the kid.
      I’m okay with #11 too. I’d probably go down very quickly. McGregor lasted longer than most people thought. Nice payday.

  • Mrs. Picky Pincher August 31, 2017, 6:27 am

    Crafting is a lot of fun, too! My sister is a SAHM, but she makes a killing selling her crochet projects on Etsy.

    • retirebyforty August 31, 2017, 11:02 am

      That’s great. Mrs. RB40 enjoys origami. I don’t know how she can make money with that hobby, though.

  • Tim Kim @ Tub of Cash August 31, 2017, 7:41 am

    Joe this is exactly the view I take on FIRE. And I think it’s the same for most of us. Because we’re all so burned out and tired of the commutes, the bosses, the lack of autonomy, etc; I think we over-correct and automatically associate “work” with stress and unfulfillment. By what we really want is work that is satisfying, engaging, and productive. So that’s why I think the concept of FI is really what people are wanting. Because you’re right, there’s only so many days you wanna just sit and watch tv and play video games. That’s depressing. Btw I can attest to the coaching & training being a good side job. It’s extremely satisfying and lucrative at the same time!

    • retirebyforty August 31, 2017, 11:05 am

      You’re right. A lot of people misunderstood FI and early retirement. That’s not the time to shut down, it’s time to explore your interest. Sounds like an interesting blog post. 🙂
      I’d like to hear more about your fitness coaching business. That sounds like fun if you’re good at it.

  • Martin August 31, 2017, 8:01 am

    My Dad tried some side hustles when he was young just to get by, such as window cleaning and working behind a bar, he is an RB75! As an RB51, side hustles for me are any ‘job’ – be it compensated or not that fulfills me in some way. If you can be FI, turn a hobby into a ‘job’ then you have reached the ultimate goal. I’m still searching for that one!

    • retirebyforty August 31, 2017, 11:11 am

      I was going to use side hustles in the title, but I don’t think it would do well in Google search. Mrs. RB40 just need to figure out how to turn her hobby into a money making endeavor. That would be perfect.

  • Solitary Diner August 31, 2017, 8:22 am

    Volunteering can also be a way of getting some of the perks of work without the downsides. Even though I’m still in the thick of working, I volunteer at our local theatre festival every year. It is a great way to meet new people, including a lot of the performers, and it’s low-stress and fun. Plus they give out free tickets in exchange for volunteering, so it’s also good for the budget.

    • retirebyforty August 31, 2017, 11:12 am

      Volunteering is a great idea. You make a lot of local connections that way. It’s a great fit for extroverts.

  • Fromusa August 31, 2017, 8:41 am

    Joe, if Intel had presented to you the option of working part time (let’s say 20 hours/week), would you have considered continue working there at your old job? Just curious.
    I’m thinking about maybe staying as a part time contractor at my place if/when I decide to “retire.”

    • retirebyforty August 31, 2017, 11:13 am

      No, I would not consider part time at Intel. I might have considered it if that offer came 5 years before I retired. By 2012, there was just too much bad blood.
      You should try part time and see if it works. Good luck!

  • Lily @ The Frugal Gene August 31, 2017, 9:22 am

    I’m doing 2 out of 10 already! All I need is retirement to get here. Busking sounds like a great way to make side money! It sounds really fun too. In San Fran, there’s these old guys that sit out in the sun near busy Irving st. playing Chinese ‘erhu’ – making some dollars and enjoying themselves. It’s cute!

    • retirebyforty August 31, 2017, 11:14 am

      Busking sounds like fun to me too. I’m just not good enough with any instrument. 🙂

  • Dividend Diplomats August 31, 2017, 9:38 am

    RB40 –

    Love the post and is timely for sure. Blogging of course is up there on the list and I would love to be a face-to-face personal finance individual for those in need of guidance, help, structure of their budget/investment plan. I would love to do that.


    • retirebyforty August 31, 2017, 11:15 am

      You probably can start coaching now. Try it out and see if you like it. You already have a platform, right? Good luck!

  • Jason In Vancouver August 31, 2017, 11:57 am

    I think flexibility component would be key for me because I want to be able to travel on whim. And I’m working those extra few years so that extra income isn’t needed at all so the job would have be fun. The jobs that I’ve been thinking of are Uber driver, movie extra, and travel agent. I love driving but Uber isn’t in Vancouver yet. Working in the local movie in Vancouver seems fun.

    I’d like to chat with people about personal finance but I wouldn’t want to take money for it. What I find enjoyable is talking about the various concepts out there but it’s too stressful helping a person make a decision that could ultimately lose them money.

    • retirebyforty September 1, 2017, 2:19 pm

      I’d like to be an extra someday too. It sounds like fun if you don’t need the money. Driving is such a chore for me so being a driver is out.

  • Mr. Tako August 31, 2017, 12:08 pm

    Great list Joe! Really any side hustle can keep an early retiree still “engaged” in life. The money part is less important than staying active.

    The only problem is hobbies that were fun can become not-fun when it’s a job. I think the key is fewer hours than a “real” job and having significant flexibility. That’s the beauty of early retirement though…you get to design your own life!

    • retirebyforty September 1, 2017, 2:21 pm

      I don’t know if it would become a chore. If you get to work at your own pace, I think it would be good for a long time. Like blogging. I could always cut back a bit if it become too much work.

  • Working Optional August 31, 2017, 12:55 pm

    Some of the items on this list definitely resonated with me.
    I wouldn’t mind house-sitting, becoming a drone pilot or an AirBnb if I had the space. Chances are volunteering and learning a new skill/hobby (like Woodworking or Drums) are probably going to be one of the first few I attempt. Funnily enough, I’m also impatient but I think its more so with my own kids than with others’ so maybe there’s something there.

  • Mrs. Adventure Rich August 31, 2017, 1:13 pm

    I’m hoping to spend time coaching youth/middle/high school sports (specifically- running, skiing and mountain biking… maybe basketball or soccer?) and maybe teaching ski lessons. Active, fun jobs that allow me to share my passion for outdoor activities with youth 🙂

  • GYM August 31, 2017, 3:28 pm

    I love # 1 of course and I like the idea of Airbnb. I think a lot of people in Vancouver do Airbnb hosting for their main gig and are basically ‘financially free’ with respect to not working a 9-5 job. I would also like to dog walk or pet sit, might as well have some more dog buddies for my dog to play with and make a little cash from that too!

    • retirebyforty September 1, 2017, 2:22 pm

      Interesting. It must be expensive to visit Vancouver now. We haven’t been in a long time.

  • Jason August 31, 2017, 4:01 pm

    I think this is a great list, but another one could be teaching a class or two at a university. You get to teach and don’t have to deal with the BS of advising, research, meetings, department chairs. I actually hope to that when I am FI. Actually, what I want to do is a series of posts at universities across Europe where we spend a year, I teach, and we just relax.

    • retirebyforty September 1, 2017, 2:22 pm

      My boss teaches at a community college. He enjoyed it much more than working at Intel. It sounds like a relaxing lifestyle.

  • [email protected] September 1, 2017, 1:45 am

    Your comments about being your own boss & choosing what to do with your time and intellect are the key items that resonate with my plans.

    I love working with data & try to post at least one chart a day to my blog: http://ak37.org/chart-picture-day/. All this data is publicly available, but so hard to find in the easily readable format at one place. Not only they satisfy my own curiosity, I have seen lot of people saying they love seeing them. Let me know what you think.

  • Turning Point Money September 1, 2017, 4:20 am

    Great list, I think a Starter on a golf course would be fun. Best part is free golf. Coaching would be fun also, I just wouldn’t do it for money.

  • [email protected] September 1, 2017, 6:24 am

    Blogging definitely appeals to me but I’ve yet to learn how to actually earn a decent income from it. Maybe if I didn’t have my 9-5…I’d have more time to work on it =)

  • MartinM September 2, 2017, 6:09 pm

    Hi Joe,
    Awesome blog. First time post, been reading for over a year.
    I reckon I’m cut from same cloth as you… highly capable smart engineer, but don’t like relentless stress and Corp BS. I was planning on quitting similar job to yours at engrg megacorp, due workload & stress, lack of family time (2toddlers), but ended up winning with redundancy.
    There was bad blood too, and spent months out of work looking. Then megacorp rang me back to do PT work 3D p.w. I went back as I missed the product most of all. This is now what I am back doing…..working with the product that I had forgotten all about dealing with the above….that completely turned me off work!
    Anyhow been doing it for over 6m, and enjoying it ok. Really rekindled my love for the product. Could come to a halt tomorrow as a contractor but that’s life in the hustle world.
    Then I might do dog walking! Thanks for all your hard work on this great blog.

  • Mr. EH September 9, 2017, 7:32 pm

    Enjoyed the article but why limit them to early retirees? These are great side hustles for traditional retirees looking for extra income and the benefits of staying engaged and active.

    • retirebyforty September 9, 2017, 9:15 pm

      I agree completely. If you’re healthy, then a fun job is really good for you.

  • Amy @ LifeZemplified September 16, 2017, 5:32 am

    Nice list, Joe. Being a professional house sitter sounds great to me. There are many on this list that are really appealing, and I’m already trying a couple now in hopes they carry over in retirement.

  • Susan Tull February 5, 2018, 6:46 am

    I love to cook, so I’d like to maybe work in a restaurant, or teach cooking. Ideally, I’d love to mass produce my sauce that my family and friends love but don’t know how to go about doing it.

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