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Consider a Side Hustle Year to Begin Early Retirement

For years when we were saving for early retirement, we were adamant: We do not want to have to work after we leave our careers.

Actually, a more accurate depiction of our feelings on the question would be to picture a toddler throwing a tantrum: “No more work! No! No! Waaahhhhhh!”

But along the way, two things changed:

1. We realized that having to work is a whole lot different from choosing to work. Work itself is noble, and acting like any work is bad is ridiculous. Sure, lots of work is overly demanding, harmful to our health or just boring, but some of it can be downright fun or come with nice perks – especially if it’s not forever.

2. We retired nearly nine years into one of the longest bull markets in history, making our likelihood of getting hit with a bad sequence of returns much higher than most. That could sink our retirement, or at least phase 1 of our retirement.

And so even though we saved beyond our original magic number (because we saved faster than expected, not because we worked any longer than we planned or preferred, Steve) ;-) we have still had sequence of returns risk on our minds in a big way for the last year or more. At the same time, all last year, the last year of my career, I kept feeling these pangs that, while I knew I still wanted to retire, I’d miss certain parts of the work. (Not of the job. Just of the work.)

And with that risk on our minds and those pangs on mine, some fun opportunities have come our way since retiring late last year that don’t involve shoving ads in your face here on the blog or pushing you to click on affiliate links. And we said yes. Because here’s the magical thing:

By taking on only a couple of small projects this year, we’re completely covering our expenses for 2018, allowing us to stretch our cash cushion and investments even farther. As far as I’m concerned, we’re now as close to sequence risk-proof as we could be without working for an unnecessarily long time.

I’m definitely sleeping well at night, knowing that.

And while I know a lot of us are just trying to make that work exit as quickly as possible, and don’t want to think too much about work later on, I have a case to make about why side hustling for only your first year or two of early retirement could be a super smart decision. Read on!

Consider a side hustle year to begin early retirement // Our Next Life // It's easy to observe that a lot of people -- not just bloggers -- end up working more than they expect to in early retirement or financial independence, in large part because work feels very different when it's by choice than when it's by necessity. So why not plan for that and make your first year of early retirement a side hustle year? The benefits of doing so are potentially huge.

The Freedom of Working for Yourself in Early Retirement

Early on in our saving years, Mark was game to quit a little sooner if we could work a little bit in retirement, but I thought about it only in terms of the hourly rate we’d make through traditional employment, insisting, “We’ll never have as high an hourly rate as we have now. I’d rather work fewer hours now and then never need to again than have to work more hours at a lower rate later.”

It was sound reasoning on my part, but I was only looking at traditional employment, which I now realize was way too limited.

Whether you’re fully retired, semi-retired, mini-retired or just branching out into the brave new world of entrepreneurship, you have the potential to earn a much higher rate per unit of your time working for yourself than you do working for someone else.

Working for yourself comes with more risk and no safety net, and that’s one of many reasons we opted to stay with our traditional careers and traditional employers until we hit our magic number and magic date. We also knew we’d have to hustle like crazy to earn enough working for ourselves to replace the well-above-average income we were making in our careers. I’m more risk-averse than many, and so you may not feel the need to make the same choice, but there is a lot of comfort in knowing that you’re likely to keep earning about the same amount while you’re saving, perhaps with little bumps in pay along the way to help speed you along.

But, if you are diligent about saving and hit whatever number feels like your comfortable cushion, you no longer need the stability of a regular income, and dipping a toe into the world of self-employment or entrepreneurship isn’t really taking on any risk at all, assuming you don’t need to make a large upfront investment to get your business going. You don’t need to replicate an income large enough to let you save for early retirement, you only need to cover your living expenses, or perhaps only part of them.

It’s why I have started thinking of many early retirees not as retirees but instead as super conservative entrepreneurs, because what they actually end up doing in retirement is working on the things they find fun and interesting – for pay – but without putting any of their financial future on the line because they already saved their cushion.

(No, I’m not joining the internet retirement police. I still think you get to call yourself retired if you damn well feel like it, and here’s a thought experiment to read if you get caught up in whether someone “gets to” claim to be retired or not.)

So if you have a job or career now that you could potentially do, say, 10 percent of, but for a higher hourly rate because you get to subtract all the employer overhead (and you can do nearly all the work at home wearing a mouse onesie), would you consider doing that for a year or two in early retirement? If you would, keep reading.

The Benefits of a Side Hustle Year

The funny thing is that I’m on the record talking about quitting my side hustle, and lamenting that my side hustle of choice was in an especially exploited field. But then I was talking about side hustling while also working, and my part-time work was holding me back from advancing in my full-time career. By ditching my side gig after doing it for 10 years, I was able to commit more fully at work and climb the ladder faster, making it totally worthwhile in our last few years of saving.

But that’s not what we’re talking about here. We’re talking about when your main career is in the rear-view mirror, you have a cushion and don’t ever need to work again, but can make the choice to work in very small doses if you feel like it. Especially for a discrete time, not indefinitely.

Then, a side hustle for only a year or two might be a great thing, for a whole bunch of reasons:

You can earn better money – Assuming the economy is booming (not always true, of course), there is good money to be made working for yourself. If you can eliminate employer overhead and offer your services directly to clients, you can save them money by costing less than a larger company but still keep a higher percentage of the billings for yourself. Plus there’s that whole hard-to-get factor: if they know you’re retired and don’t need the money, they might be willing to pay more to get you. (I have seen enough cases to believe that this is very real for many folks. I’m not talking about bloggers.)

You get a great sequence risk hedge – Which would you rather do to head off sequence of returns risk: work one more year, or work a tiny fraction of your first retired year? That’s your call to make, but if you think in basic four percent rule terms (though you know I think there are problems with that), holding off on spending any of your assets for a year gives them a year to grow (or to avoid getting further depleted in a down market, if you hit a bad sequence right out of the gate). And that could mean either having more to spend in subsequent years if you keep your withdrawal rate the same, or being able to use a lower withdrawal rate when you do start tapping principle, which increases your chances of your money lasting.

You avoid creating a resume gap – While any early retiree who intends to truly stop working is going to face the resume gap at some point, it’s smart to delay creating a gap for a little bit while you figure out if you’re actually cut out for this early retired life after all. I’ve heard from a lot of people over the years who’ve ended up going back to work, and if you do some side hustling for yourself while you feel things out, it would make the re-entry to traditional employment much easier than if you make a clean break.

It could let you beef up your cash cushion – This didn’t apply to us because we went into early retirement with nearly three years worth of cash already in place (which seems a little high now, knowing what we know about this year’s income, to be honest), but if you didn’t want to divert some of your accumulation funds away from investments and into cash savings, you could use your first year of retirement side hustle as an opportunity to pad your cash stockpile.

You can tailor it to replicate the aspects of work you’re best at – Because you don’t need the money, you’re in total control of what kind of work you’ll take on. And that means leaning into those areas or tasks where you know you rock, or that make you feel most fulfilled. Like speaking and presenting was always my favorite part of work, so I can say yes to a select number of those opportunities now and no to work that I know will not play to my strengths.

You can be picky and only take work that’s fun to you – Whatever that looks like! Work that is truly fun feels like a scam. “Really, they want to pay me for this?!”

It could involve travel or other perks – If you’re lucky, and we have been, the side hustle work could involve some nice side benefits like travel or the chance to do something you’ve always wanted to do. I didn’t quite make it to United million miler before we retired, and so every mile that someone else wants to pay for to get me there is money we don’t have to spend.

Consider a side hustle year to begin early retirement // Our Next Life // It's easy to observe that a lot of people -- not just bloggers -- end up working more than they expect to in early retirement or financial independence, in large part because work feels very different when it's by choice than when it's by necessity. So why not plan for that and make your first year of early retirement a side hustle year? The benefits of doing so are potentially huge.

Our side hustle year still includes lots of time for this.

Our Side Hustle Year

It was important to me to specify earlier that the side hustles we’re doing this year to cover our expenses aren’t about monetizing the blog. Rightfully, FIRE blog readers are beginning to question whether the confidence many bloggers have in early retirement is justified, or is the result of those same bloggers having a much larger hedge than “normal” early retirees in the form of their blog income, especially if they don’t disclose it, and most especially if that income comes from pushing certain products or services that may or may not be in readers’ best interest. It’s a critical question to ask, and I’ll have a lot more to say about this on Wednesday. (Heads up: It will be feisty. This one’s been brewing for a while.)

Instead, we’ve each taken on very small projects related to the careers we just left, and together those are all we need to cover us for the year. But it has all been on our terms:

It’s extremely limited in scope – Anything open-ended is a hard no for us. But something that’s very part-time for a month or two and can be done on our own time? Great.

It’s fun work – Clients we like and interesting problems to solve make for good side hustle work.

It’s work we feel awesome at – We’ve turned down projects that we could technically do but that aren’t in the areas of our expertise where we really shine. But when opportunities arose that would let us feel like rock stars, it was easy to say yes.

It comes with perks – The projects we’ve said yes to have involved travel to places we’ve been stoked to visit.

It fits our high school rule – It’s work that’s fun and that we feel good at, and that doesn’t come with a lot of busy work or logistical headaches. Easy yes.

The best part is: while we already achieved a point at which we’d never have to work again under all but the worst sequences of returns, we’re now rock solid for good. After these projects wrap, we’ll feel fine about embracing a big resume gap. I’m sure we’ll work again, but it might not be for a looooong time, and it won’t ever be because we have to.

Share Your Thoughts!

What do you think about doing a side hustle year to begin early retirement? Or are you a bigger fan of the entrepreneur life and going for a longer-term side hustle (or main hustle) to get out of traditional work sooner? For folks who’ve already retired, have you found yourself wanting to work more than you expected? Have you parlayed that into a profitable short- or long-term side hustle? Let’s discuss it all in the comments!

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105 replies »

  1. Smart move I think! Like the fact that you mention the sequence of return risk here, which will apply to many folks in your position at this time in the bull market. Hustling a bit on the side, while having fun and not having too many strings attached is a good idea! Have fun.

    • I think the timing is a really key part of it. If we were a year or two into a recovery, or even a few more, we wouldn’t feel like a correction is inevitable, but we sure do now!

  2. We have planned for at least five of those :)

    We will have to live in our current home for another five more years (until our son finishes high school). It means a property tax of at least 8000-9000 dollars a year that we haven’t included in our 4% number.

    Plus we already set a date. We may not get to FI unless the market cooperates. So yes, five years of side hustles…

    • That’s great! Though I think you’re technically aiming for a slightly different model, though still a fantastic one if it suits you and your work! I’m guessing that you guys are making the trade-off between working full-time a little longer vs. quitting sooner but then working part-time for five years. And especially with a kid at home, I don’t blame you for wanting to free up more of your time sooner rather than later!

  3. In my push for FIRE I feel that after I reach the finish line I will never want to work again, but I know it’s not true. So as a side, unpaid yet, gig I started planning getting into the sustainable urban development movement. I seem to have the right ideas, get into radio and newspapers offer enough that my name begins to resonate, and with my small non-profit social movement I have enough power to change something. So who knows, perhaps when I finally pull the plug, this is what I will work on?

    Another thing is teaching: for now it’s a side gig. I enjoy it, it pays well, but I always need to cram it into my weekend calendar and end up too tired to really have fun with the students. I definitely want to continue doing it after FIRE, but to do this, I need the program to continue, and therefore need to keep working now, making it less fun.

    Overall, the end line can’t come soon enough. I will be ready to take on another challenge, without the payments as number one reason for it!

    • Oh I totally remember that feeling! It was a huge surprise when it went away. :-) The good thing is you don’t have to know now what your future side hustle might be… even a year ago, I wouldn’t have guessed that we’d be doing what we’re doing in tiny doses now. ;-)

  4. Hi! This post couldn’t have come at a better time for us. We were just discussing this weekend our options:
    * Work for five to seven more years and retire
    * Work for three more years and semi-retire after a career break (travel with our 18 year old for a month or so, travel the two of us across the country, and settle in to new side hustles, and/or work projects)
    * Work for seventeen years with full pension (including health benefits)

    Most of our peers find even the third option too risky and feel they have to work through to social security retirement age. For, us I’m looking at the second option. We definitely want to use some of our skills in retirement (we worked hard for those skills and pursued them for a reason), but don’t want to be tied to a desk 24/7. Plus, relocating when our little one heads off to college (three years) is important to us. We miss our California family and lifestyle. We’re just exploring this third option, and as professionals in our fields of choice I think we can make a go of it!

    Thanks for the success story/inspiration.

    • I’m glad this was so well timed for you! I know in our case we wouldn’t have been comfortable doing your second option, because we wanted to have our full number saved before we left lucrative careers. But given where the markets are and how overdue they are for a correction, having a little padding feels very comforting! :-)

  5. Great post — I’m older and probably can quit my traditional job soon. I’m worried about health insurance so I do hold on for my employer’s health plan. But I am experimenting with side hustles. Unlike you, I enjoy teaching yoga and have found ways to make good money on the side. I also pick up writing gigs that I can finish in the early mornings and weekends. I made so much side hustle income in 2017 that I created a S corporation a few months ago. When I do stop working full-time, I plan to adhere to your fun-only philosophy and only take on work I enjoy. I have the tax structure in place. But I will have to figure out health insurance!

    • Experimenting is a great way to figure out side hustles you might like! Re health insurance, make sure you price out what it would be if you’re eligible for subsidies – it was less than I thought in Minnesota (and one reason, like ONL, that we’re ok with paying our state’s income taxes in retirement – we have great health care options). Lastly, where did you find writing gigs? That’s something I’d like to pursue (my last day is this Friday). :)

    • Oh I get holding on for health insurance! That was probably the hardest thing to let go of. And I LOVED teaching yoga — I just didn’t love that I felt exploited by the studios where I taught. ;-) And I am not rushing back to it because I want to keep my schedule flexible and weekly classes would cramp my style. Hahaha.

  6. Love it. I Conservative Entrepreneurs! That is tee-shirt territory right there, Tanja. I like to call it “retirement from employment at-will”, or, avoiding any work you can get fired or laid off from. And as you describe, working as a contractor has a lot of pros to it. I’m not sure if you can treat that income as pass-through via an LLC, but I’ve given myself something to research now…

    Can’t wait for your feistiness on monetizing. I’m trying a bit harder these days to promote mostly things that have worked for me (hosting service, airbnb, etc.)

    • Definitely take a look at the new tax rules for pass-throughs. We decided NOT to form an LLC based on that because it was just higher costs for no real benefit other than being able to time income, and we’re talking about fairly small amounts, so not anything we’d need to split over multiple years. And sole proprietorship requires no extra tax filings, which is fab. :-)

        • I hope it was just published, or some of it could be out of date based on the new tax law. And pass-throughs get new benefits, so you don’t even need an LLC anymore to get the big write-off — they’re giving that benefit to sole proprietorships now.

  7. Love to hear the opportunities coming at you – I’m assuming part of the reason you didn’t / couldn’t start planning this side hustle income is the projects are in your same field as full time employment. That could have created a conflict with your prior employer if you’re investing time elsewhere. Good thoughts

    • Mark’s work is directly tied to his old work and is with the blessing of his old employer, and it’s an extremely short-term opportunity that couldn’t have been planned for and just popped up. Mine is sort of in the same sphere, but wasn’t something I could have planned either. ;-)

  8. We are definitely looking at a side hustle once we hit FI, but it’s mainly going to be to break even on hobbies that we’d be doing anyway. We both enjoy making things and materials can be expensive. So while we have a hobby line built into the budget, if someone wants to pay us to make some stuff for them and it looks like an interesting and fun project, it’ll cover the materials costs for stuff we’d be making for us, family, or charity. We figure we’ll be able to ramp up or ramp down if a) we need extra cash as a hedge or b) making stuff for a customer isn’t as much fun as we thought it would be.

  9. This is pretty much my plan. Once I’m done working full time I’m going to probably consult for a little bit. I figure cutting back to half-time or something would be a nice transition, and it could probably still cover all of our expenses which is nice. I am sure my plans will change though, because that’s pretty far in the future.

    Who knows, maybe I’ll have a more legit side hustle then and focus on that instead of the consulting plan.

    Glad to hear things are working out well for you guys!

    • Thanks, Dave! I think your plan sounds great, and going from full-time to half time or less will still feel suuuuper luxurious. (And we’re working like 5% time, so that’s even better. I endorse that approach!) ;-)

  10. I needed this post! This is exactly how the reality hit -we want to work, we love our careers, we found our ‘work calling’ but want to do this on our terms. I love Conservative Enterpreneus!

    • Glad this resonated with you! :-D And yeah, I think for folks like you who are lucky enough to find your calling through work, wanting to do it on your own terms makes TONS of sense!

  11. I really like this approach to FI. The side hustle turned “fun job” seems like a great way to step into retirement and begin to dictate your life while still having social interaction, mental stimulation, and a bit of income to boot! I can’t wait to hear more about your side hustle!!

  12. We’re definitely planning on something similar. 😃

    Even if we don’t have plans to return at all, I’ll likely at least go on a part time on call arrangement at work, for instance. That way, I don’t need to work a certain number of hours, and I can only take on projects that sound super interesting (and are short term), yet I don’t need to go through a hiring rigamarole / onboarding process each time. Plenty of folks at work have done something similar if taking a year off to travel or the like, and it makes coming back to full time work much easier if needed.

  13. A side hustle is a wonderful thing to have in early retirement, especially early on. I’m getting to do what I’ve always enjoyed doing, just without that huge cloak of “I have no choice but to do this” all around it. It’s a magical thing!

    And, I guess I just assumed that, all else equal, you would have preferred to retire even sooner than you did. If that’s not true, I’d be happy to re-word that for ya so it’s more accurate. :)

    • I definitely struggled at the end of 2016 (for reasons that are probably obvious to everyone now!) ;-) but we were happy with our quit date and were just stoked to finish ahead of our goal! :-)

  14. I figured you would both be doing a little part-time work in your retirement! The right work is fun and rewarding. I share your concern about sequence-of-return risk. A little income that brings the withdrawal rate down from 4% to 2 or 3% goes a long way to reducing that risk.

    You are both a long way from drawing Social Security and enrolling in Medicare. Your income will be lower and healthcare expenses higher until you do. Some part-time work helps balance the finances out in the meantime.

    I’m looking forward to future posts where you tell us more about how the side gigs are going.

    • I’ll keep you posted! And yes, all true. I love how you put it: the right work is fun and rewarding. Absolutely! Working just to work defeats the whole purpose of having saved up to achieve FI, so the best part if that even if you do want to earn a little money, you can be suuuuper picky about how to do so. :-)

  15. The market has been unusually high. I am concerned about a lot of people in the FI community who are retiring right now because of the Sequence of Return Risk. I love the “high school rule”. Nice way to look at your decision.

    • Thanks, Susan! And yeah, I hope that folks have some solid contingencies in place and are ready to be flexible because the next correction could be quite unkind to those who have already left their careers.

  16. Another good, thought provoking post. I’m 10 days from retirement and the question I get asked the second most, after when is your date again, is are you really retiring or will you start looking for work again once you have finished your current gig. Like you, I’m sitting on 4 years of after tax money (basically cash) so we don’t have to touch any investments should the market correct What we plan on doing is taking enough out of our investments to keep us in the 12% tax bracket for the next 8-10 years. If the market takes a bad turn we will leave the money in retirement accounts alone to give them some time to recover. My current plan is to make the remainder of 2018 the year of family, faith and me. Keeping commitments for work to a minimum being open to interesting short term opportunities.

    I agree that short term work in your area of expertise is the easiest to maximum the earning and minimizing effort. I may also consider doing something that will teach me a skill in an area that may benefit me or my family/friends in the future – say in a trade. I’m a white collar worker now and getting back outside and working with my hands (carpentry, electrical, HVAC repair, plumbing, auto repair) may be something that I would consider. I have basic skills in all of these areas but I may consider helping out to earn a bit of money and improve my skills beyond my current level.

    I think it was one of your earlier posts that the touched on the concept of letting yourself get a bit bored so you can really explore what you may want to do with the next chapter of your life. That is where I sit as of today…

    • Your approach to work totally matches ours. I can’t IMAGINE, after all those years of saving, agreeing to something that would require more than a month or two of part-time work. What would have been the point, then?! But if it’s fun, interesting, rewarding and short-term? Then why would we NOT want to take it on, especially given the state of the markets?

      And I still totally agree with that sentiment about letting yourself get bored, but I have not yet experienced one second of that. ;-)

  17. I have a half baked idea for a side hustle experiment, where I take very low paying jobs in my community: helping out at the local board game store, working as a cook at McDonalds again, maybe putting back books at the library. Basically: something that doesn’t take up any space in my mind when I clock out, hopefully.

    The low pay is obviously a drawback but I do remember (naively?) that I was still happy working those jobs years ago…

    • Also, I’m working my way through Big ERNS series on sequence of return risk and, um, yeah, we all probably should be pretty conservative if we’re thinking of retiring for 60 years or so in this environment. CAPE’s above 30!

    • I think doing that as an experiment could be interesting, but not as a side hustle. ;-) Those minimum wage jobs just require so much work to earn peanuts and you can’t control much about your schedule. (It makes me super sad for those for whom this the entirety of their economic options.) But if your goal is to get in touch with those at the lower end of the economic spectrum that way, then I fully support it… so long as unemployment is low and you aren’t taking a job from someone who truly needs it. ;-)

  18. Would I do the job in High School?
    LOL well maybe not the writing but the photography is a blast and I’m having fun doing both.
    I am doing my side hustle work because honestly it is still a bit of fear that wants me to preserve my savings.
    Early Retirement is enjoyable and I have loved it so far, always looking to your blogs as a affirmation on my path.
    Have an awesome week both of you :)

  19. interesting article here. mrs. smidlap hasn’t worked in about a year since the record label closed. i still come here to my low stress job 40 hours and not a minute more, but i think she’s bored at home, even with the art projects. she is a marketing expert in music but i think will work part time for our wine store friends setting up some systems for them and getting some education on that. we were even talking about maybe moving to the west coast wine country where we might have to work a little in sonoma, or willamette, or even some goofball central coast spot like solvang. like y’all, i think we could work enough to cover living expenses without having to continue saving/investing but not drawing down right away. plus, those are good social jobs mostly.

  20. Looking forward to Wednesday’s feisty post. Sometimes I look at blogger’s income reports and think that maybe I would like to start a blog, but then I realize that I would have to find a way to drop a link to Personal Capital and Mint into every single post and THAT’S NO WAY TO LIVE.

  21. YES! I have been thinking a LOT recently that FIRE is often super safe entrepreneurship for many people and honestly, that almost sounds more fun at this time. Being able to make just enough money doing only things you love because you’re not focused on trying to save FOR retirement. Thank you for saying exactly what I’ve been noticing.

    • Great minds think alike! :-) And it’s a world of difference working this way when you already have your whole cushion saved than it would be earning the same amount and covering expenses but having to worry about the future and retirement. It is a MASSIVE blessing to be free of that worry.

  22. Side hustles are talked about quite a bit in the FIRE community, but they seem quite mysterious to me. I’m wondering if you could expand a bit on where they actually come from? You make it sound super easy, like a side hustle just magically appears in one’s life, or it is assumed that one’s interests will naturally result in income-generating work. However, I have zero confidence that this will be the case for me. I am a software engineer (currently in a management position) and have always worked in a salaried, full-time position. I have never had any thought or idea of anything I would do that is entrepreneurial in nature. My interests outside of work (that I would like to spend more time on after FIREing) are unlikely to result in income. I know that there are people who do consultant or contract work in software, but breaking into that seems like something that would take quite a bit of effort, networking, and possibility new skill development. Any thoughts/advice on this front?

    Your arguments for side hustles in the first year make a lot of sense. We are looking at FIREing as soon as this summer (!) and I am also concerned about sequence of returns risk. However, we are both super burnt out on our jobs/working, and the prospect of actually making a point of picking up work in the first year seems daunting and unfeasible. I don’t currently have the energy to do the sort of networking and possibly skill development that might be required for me to develop the real possibility of a side hustle in my field, and I have no idea if/when I will regain interest/energy for that after FIREing (it does seem likely I will regain it eventually, but I’m not confident that would be in the first year). I’m curious what your thoughts are on burn out/recovery from full-time work in relation to side hustles in the first year?

        • My ‘side hustle’ after retirement would look more like cutting back at work to maybe 2 days per week, IF my employer was open to that. Not ideal, would still need to show up at work, doing things I’m not excited about. But hoping to retire at the end of 2018 and sequence risk is causing me to seriously consider this. Not able to think of other things I could do with a lot of freedom built in to make some income after I leave my job…..Open to ideas!

        • Is there any natural consulting you could do that would play to your experience? That is the most natural starting place. And I get your nervousness on retirement timing 100%. Just make sure you pad your cash cushion this year so you aren’t reliant on a side hustle to do that for you, and consider saving a little more if you can than you’d planned, to help ride out market dips. :-)

    • Great question! I think you’ll want to take at least a month or two off completely, if not longer, before you contemplate side hustles, so you can sleep off some of that burnout and get the jumping on the bed stage of early retirement out of your system. ;-) And then you have two options: either do a side hustle unrelated to your current career, or do one that’s a bit more of an offshoot from it. Mark’s is directly related — old clients came to him with a new project and he said sure. Mine is more peripherally related, but also kind of fell in my lap. I wonder if you could ask a friend or colleague out to coffee who does software consulting and get their advice on how to break into it if you feel you don’t already have a few relationships you could tap. That might also tell you whether retraining would be required, and then you could decide whether that’s worth it or not. And if you go an unrelated route, then the sky is kind of the limit. Is there another career path you’ve always wished you could pursue instead? If there something you enjoy making that you could sell on Etsy? Is there some other skill you possess that you could teach others to do? My side hustle for years was teaching yoga and spinning, and a fitness certification is pretty easy to get. I’d do that again if I wasn’t so averse to getting locked into a schedule at this point. ;-) Every path is going to look different in terms of what kind of preparation you’d need and what it would take to get started, and if all of that sounds too daunting, maybe the best option is just to get a part-time job at a bookstore or somewhere where you’d get some worthwhile perks. ;-) (Like how we say we’d work as lifties at the ski resorts if our investments tanked so we’d at least get free season passes.)

  23. In my view, post FI, a side hustle which does good to the world or others is most valuable. I tutor English on the side. It’s a pain in the ass to get to one student. But I was late this week, and realized that she needs this more than I need to $30 I’m changing her. That mind shift changed my thoughts to doing good even if it’s not that lucrative.

    • A woman after my own heart. :-) That’s awesome that you tutor English as your side hustle! It sounds hard to scale, though, like when I taught yoga. You can’t teach five classes in a row, so it’s often a lot of travel for one hour or at most two hours of work. But I love your mindset of it also being a service.

  24. I’m always wary of recommending side hustles as the first step to getting finances in order, but they 100% make sense in this situation. I do keep a few myself, but mostly because I find them fulfilling, not because of the money. You do still need to make sure you get some kind of return on your effort!

    • I agree! And I would NOT advocate retiring before you hit your number to side hustle. But if you’ve already hit your number and you just want to hedge your bets a year or two, I think that’s totally different.

  25. I’d be very curious for a post on how you assess job opportunities against the need to keep your income below a certain threshold for your health care subsidies. Also, do you think you will contribute to an IRA this year?

    • Good question! I mean, we basically have a number we’d like to stay under that is what we submitted on our health care application, we know approximately what our rental and dividend income will be, and so we’re not planning to say yes to anything that would put us above that number in total. So we’ll basically be at that number by June and will be done side hustling for the year. ;-) And if we go over that, then yes, we’ll put the rest in an IRA or two.

  26. This is similar to our plan. We have a partial FIRE number to hit, after which we plan to switch to traveling 6 months and working the other 6. I calculated that even if we were each only making minimum wage (which is unlikely) that we’d still make enough to only need to do that for a max of 5 more years. And if I’m wrong, that’s still a fine way to live until we do hit our real FIRE number or become eligible for SS, whichever comes first.

    Rather than consulting work, I have in mind things like getting a job at a winery or learning to make and sell pottery, finding out if knitting baby accessories is as lucrative as I think; things I’ve never done, but want to take a whack at because it wouldn’t matter if I made a ton of money.

    • I’m so curious — if you stayed with your careers, say, one year longer than you’re planning, then how many years would you have to do your 50% work plan? I think your plan sounds like a nice way to get some time freedom sooner, but I also know I’d freak out about leaving a career before we were rock solid. (I know that’s just me, though.) ;-)

  27. Great post Tanja. In my case I can’t make nearly as much in my side hustle as I can in my now part time job since I chose a side-hustle that involves an artistic angle and I’m a marginally-talented artist. But I enjoy it so that’s what matters. I don’t really need the money either, so the small monthly amounts I’ve been making are just a nice bonus.

    • Thanks, friend! I think in your case your part-time job is the equivalent of our side hustles (although we might be spending less time doing them — not sure!). So long as you have a way to shore up your savings a bit — and you have at least two ways to do that! — you’re good.

  28. So glad you’ve found ways to minimize your sequence of returns risk while doing work you love that’s totally on your terms. That’s awesome. We’ve always imagined we’d do some very part-time, flexible work in early retirement. Or something closely related to our passions that we volunteer for now, but maybe for some money if there was a greater commitment level. Not sure what it’ll look like but I’ve never been opposed to it and don’t think it means you’re “not retired.” It does seem like the people with the work ethic, drive, and skills to retire early are the least likely to quit working altogether!

    • I so agree with that. I’m realizing now how hard it is to go from being a pedal to the metal careerist to a… nothing. ;-) Not that some haven’t clearly mastered it (or that some who’ve reached FI weren’t actually especially committed to their careers, and I think they’d admit that!), but at least for us, it’s hard to know that we have skills and talents and use them for nothing at all. So if opportunities come along that are short-term, interesting, fun and align to our purpose and pay well, it’s sooo easy to say yes!

  29. Oh, i can’t wait for your Wed. post. Like the bloggers who say they don’t monetize their blog but there is an Amazon link to everything they buy or want or like? I don’t ‘mind’ the monetizing portion when they’re open but I don’t like the lies :(.

    Consultants can make killer $$$ on their side gigs. I was an administrator for a healthcare consulting firm and I was always amazed at the rates they could command…

    • That’s new to me — there are people who straight up say they don’t monetize but then have links all over the place?! I definitely have a few links here, but try to be transparent about my policy on them (covering expenses and nothing more).

      And YES to consulting. It’s definitely something folks should keep in mind.

  30. Thought provoking post – thanks. I wonder though – where does it end? Will one year turn into two? You obviously have projects that you love and meet your hell yeah criteria which is fantastic. For me, I have been driven more by the money than the career satisfaction all these years to get to a few years out from FI – and that’s a hard thing to turn off. I’m wondering if it would be easier for some people to just draw a line. It’s an awful phrase, but some people are coin operated during their working lives and I think sometimes it’s hard if you’ve been one way all of your life to turn into someone that can selectively choose some projects and turn away others.

    • I think that’s a really important question to ask yourself! And that’s why I decided to create the high school rule for myself. You’d obviously come up with your own criteria and/or time limits, but having some way to judge whether a post-ER project is truly worth your while or if you’re just taking it reflexively is super important. We’re committed to being done after this year so we can focus on volunteer stuff, but I also wouldn’t ever want to close the door completely. If the world’s coolest project came along in a few years, I can’t see myself turning it down if I could do it on my own terms.

  31. Hi there! The “side hustle after retirement” is exactly what we call “An Encore Voyage.” We have actually had our own business (architectural consulting) operating for the past 7 years. The importance is that we don’t “have to” make a ton of money, (we’re in the same FIRE position as you, in the same bull market.) The beauty is that we get to decide what to make of each day. We get to decide what clients to accept, what projects to choose, and quite frankly, how much work we want to do at any given time. We have many project opportunities that we can base from nearly anywhere there is an airline, and much of our work can be done digitally. And almost every morning, we tell each other, “This is a good gig!” Quite frankly, we don’t know if we’ll ever “retire” in the conventional sense of the word – just move on to a different Encore! ~ Lynn

    • It’s so awesome, Lynn, that you guys have figured out an encore career that works so well for you! That’s all that’s important. Having a continuous stream of clients would make me feel not especially retired, I think, but that’s just me, and my opinion is irrelevant here. ;-) Congrats!

  32. My side hustle for the past two months has been reading from Hiya to this latest post. :-)

    It’s been great fun seeing your story unfold. So happy for you. And I’m finally caught up to the present!

    You usually seem to make me think about things in ways I hadn’t thought before. Looking forward to more insightful posts.

  33. I’m very risk-averse. Leaving your marriage with 4 kids under 5 and only $60 cash will do that to you.
    dI’m looking at retiring in 4 or 5 years, when I can access my super. (401K sort of equivalent, for you Americans.)
    But teaching offers a lot of options to soften the ride into full retirement. Work all the year but part-time? Work a term or two or 3 covering people going on long-service leave, then travelling etc on the time that’s left for me. Working an extra year full-time and then stopping work cold.
    I’m lucky. I work in a lovely school where the kids are gorgeous and I love teaching them. After my geo-arbitrage the commute is a bit of a bitch but I can handle it. (Thank God for podcasts.) Retirement will more than likely be something I’ll ease into into, rather than just leap into cold turkey.
    I’m interested reading about how your adjustment is going. :)

    • I can see that you would be risk-averse! Bravo for being willing to consider early retirement at all — that’s tough for us risk-averse folks. ;-) That’s wonderful that teaching gives you so much flexibility. Given that, I think your plan to ease into retirement sounds spectacular!

  34. Love this! I’ve made no secret that I want to transition to my side-hustle half-time or less once my money situation is there. Only taking the clients I want to serve and only so many. A nice slow year and time to do what I want. I’m also trying to build my CV now so I get invited to do more cool things. My favorite trips have always been the ones I’ve gotten other entities to pay for. I want to up that game.

  35. We are in year one of early retirement plan and doing exactly this – working our side hustle which is contract/consulting in our fields, about 3 days per week, minus some long breaks. we are treating it as a transition year, both in terms of getting used to having lots of free time and to let our capital grow untouched even if we aren’t adding to it. We are also using earnings this year to pay for some lifestyle things we want, rather than use capital ( caravan, boat and renovating the house we’ve downsized to). When each of us resigned, we both got asked to contract back to our employers for specific projects. I’ve moved on to other things as well. We earn double our previous hourly rate and run it as a business, not wages. What we’ve learnt as our need for a monthly income has gone and our capital has grown is that if gives you choices at every turn – don’t need that job ( as it turns out they’d need us more than we need them), don’t want to work That week, do want to buy that caravan, do want to put money into that investment. We do real estate investments and our cash purchasing ability gets us most deals we want.

    • That’s great you guys have figured out a part-time work arrangement that’s working well for you! And even better that you feel you can walk away whenever you feel like it. :-)

  36. The aesthetic of your blog is much improved because it is not heavily monetized. Thank you and bravo for that!

    Planning to provide vacation coverage for other doctors once I “FIRE”. This will facilitate travel around the country (sometimes there are opportunities in Guam or NZ or Caribbean, too), allow me to work completely on my own terms (ie I think I’ll take the whole summer off and I don’t have to ask anyone’s permission!), and still get the rewarding interactions with patients with a lot less of the politics and committees/additional duties that come along with a full time position.

    Currently locums in my specialty pays about $1200-1500/8 hr day – so won’t have to work too many of those a year to provide some solid income. And I can flex up or down, taking more or less jobs, based on how the market is doing, or how much our expenses are varying from the expected.

    Not exactly a “side hustle” or particularly entrepreneurial but a nice way to slide out of full time practice and eventually into full-time retirement, available for physicians and nurses – and probably other health care professionals, too!

    • Thanks, friend! Glad it makes for a better reading experience. :-) I think that totally counts as a side hustle, given that you don’t have to work much to cover a good chunk of expenses, and especially if you also get travel perks out of it! For someone like you who has a meaningful job in an important profession, it’s great you’re planning to keep a toe in your work after you retire.

  37. Great article! I did the move to part-time, consulting work almost 1 year ago with the following mindset: covering the expenses while letting the eggnest grow. I can say that its been better than I thought. Got a big contract recently giving me 800 hr of work with a highly flexible work schedule for the following year. But since it’s the type of work that totally plays to my strengths, it totally feels like a scam, as you said!

    I agree with lots of your points: I make 50% more per hour. I also get paid when I travel (as opposed to be expected to travel on my personal time when being full time staff). However, you need to factor in a bit of admin time for invoices, expenses, etc. that brings the mentioned percentage lower. I see this as a great learning experience since I want to potentially start a totally different side-hustle later this year that will also require me to invoice clients, etc, So the hassle is definitely worth it!

    And with the markets presently plunging, I sleep well at night knowing that this gig more than covers all of our expenses. It’s even allowing us to invest a bit more.

    But I feel the most important point you made is about work choices. Yes, you can choose work that plays to your strength, that speaks to you (i.e. that feels like a scam!) That’s really awesome! Furthermore, I think you NEED to choose work that plays to your strengths ( at first anyway). As Im learning now, an independent consultant doesn’t have a ton of margin in terms of work performance and results. A client doesn’t like your work: you’re gone. As simple as that. When I started my self-employment journey almost a year ago, work was scarce and it took me quite a while to get a rhythm going. At one point, I almost accepted work that was high stress and demanded skills that were far from my personal preferences and personality style. I think knowing that we had a very good cash cushion to ride the wave (18 months) allowed be to be patient and really think things through. I’m so glad that I refused the work at the end! Today, I’m turning down fun work on a regular basis. Great problem to have!

    As you said, fun projects, some free travel and more free time for other adventures. Got 32 days of powder skiing under my belt this year (epic snow year in Western Canada!). Keep up the good work on your blog. Rock on!

    • Soooo jealous of all that powder!!! We’ve been having an incredible March, but it was dry until a few weeks ago.

      All great points on the up and downsides of side hustling. We are treating it as true gravy, so if things didn’t come through, we’d be a-okay, but I definitely see the other side of that if you need a little more work to make your FI plan work out. Glad you now have the best problem possible and turn down fun work!

  38. Early retirement is still a dream for me. But, considering a side hustle helped me a lot to get out of my debt troubles. I started working as a freelance blogger to earn some extra money. You won’t believe, I started earning so well, that I had decided to pay off my debts on my own. After 1.5 years, I paid off my credit cards debts, Yes, to earn some more extra, I sold my expensive car and rented the garage as well. After that, I paid off my student loan debt recently. Now, I am working hard to save more to build an emergency fund. My target is to avoid debt and secure financial life. Wish me luck!

  39. Also, a side hustle at retirement let’s one roll over your built up retirement funds into a newly created solo 401k instead of a tIRA – which then allows a non-deductible tIRA contribution, and then an immediate tax-free Roth conversion of that IRA contribution $ each year (as well as your new 401k contribution).

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