Side hustles and second jobs – are they even worth it?

I was recently discussing side hustles with a friend, who was considering starting a small business alongside her day job. This topic has been discussed over and over within the FI world, and with good reason: side hustles are both interesting and a chance to make some extra moolah!

But I’ve always had a love/hate relationship with the idea of side hustles. Often I hear about someone’s side hustle and I think, “dude, that’s just a boring second job – who wants that!?” Other times I’m like “yee-ha, that sounds cool! Even if it pays crap, I want to try it”.

So why my hesitation? I think it’s because I see side-hustles as both a potential outlet for passion, and a potential trap for disappointment. Let me explain:

What I love about side hustles

  • it’s a chance to spend time doing something you are good at and enjoy. This is the primary benefit in my eyes, as hopefully money doesn’t dictate our lives
  • it’s a chance to make some extra $ in your life, potentially with tax benefits superior to employee compensation
  • Having 2 sources of income adds a back-up in case your primary job slips. Or, your side hustle could potentially grow big enough to be your main gig. 

What I don’t like about side hustles

  • Often it’s just a second job. You end up trading time for money doing something you dislike. For example, I personally don’t enjoy cleaning floors, so I’d call a night-gig as a janitor a second job, not a fun side hustle. This wouldn’t add happiness to my life.
  • Sometimes turning your hobby into a ‘job’ can kill the passion. For example, if I sold my painted rocks on Etsy, it might bring a few hundred dollars a month in revenue, but it completely kills the joy I get from giving my art away for free.

Why do I feel this way?

Mostly, I personally feel a potential trap to miss out on life.

Here’s a real-life example: during college my brother worked a night gig at a bank, reviewing mortgage applications for a year. This was tangentially related to his college studies and he made a small fortune for a college kid. Cool, right? 

Well, he tells me he “missed every sunset of 2006 at the age of 23”. That supposed small fortune of money is now inconsequential to him, and he’s never going to be 23 again. In hindsight, he says the tradeoff wasn’t worth it.

But, I LOVE hearing about side gigs and second jobs that allow people to live more of life, not less. I do believe that side hustles can be a tradeoff worth making.

Here’s a happy example: my friend works for a pharmaceutical company, and she can pick up work at CVS as a pharmacist on Sundays (earning double-time!). For a few years in her early career she worked on Sundays at CVS, even though her primary job paid well. She never relied on this job, and she eventually bought an investment property and left that side gig. She’s happy with the trade-off she made, and genuinely enjoys what she does. 

So what’s a good side hustle?

In my mind, the ideal side hustle would be both highly enjoyable and lucrative for the time input. In reality, I think many side hustles end up being a tradeoff between one or the other, which is just part of life I guess. And since life is full of tradeoffs, let’s not get discouraged when searching for a great side gig.

Side hustles of my past – the good, the bad and the meh

GOOD: Freelance bartender: I used to serve drinks at weddings when I was in my early 20’s, when my primary job was sales. I loved it! Pouring drinks, laughing, even dancing with people who were all celebrating – what’s not to love? But eventually I kind of grew out of it and focused on my sales career. I guess life moved on, but I have great memories from that time!

BAD: “Family conveyor belt”. In hindsight, this is more funny than bad. As a young teenager I took on a paper route. Unlike the movies, where a cute kid rides a bike to deliver newspapers, this job was delivering junk mail and it wore out the whole family! Mum had to drive me to pick up thousands of flyers, my 3 siblings and I set up a conveyor belt system on the kitchen table, and then as a family we packaged hundreds of stacks of different junk mail for delivery. The job paid almost nothing, and it literally took all 6 of us (parents helping too) to achieve the crazy-high quota of junk mail delivery I had. We all laugh about it now.

MEH: Second job at Post Office: I spent 6 months working nights doing postal sorting in my youth. Similar to my brother, I made what I thought was a buttload of money at the time. But I worked every night, ignored my friends, and missed out on some opportunities to enjoy life at that age. I have no regrets, but won’t be doing a hustle like that ever again.

Side hustles I wouldn’t mind trying

  • Part time tax preparer – I like this idea because by helping others file taxes, I can take on work seasonally as it suits me. It helps others and is a valuable, marketable skill. I’m a nerd and I find taxes kind of fun.
  • Nursing home assistant – a friend of mine picked up casual work caring for elderly during college while studying to be a Registered Nurse. Casual work paid well and the experience was valuable after she graduated. I do volunteering now, and can see myself stepping up to a caring role some day. Maybe.
  • Sports umpire – 2 different friends in my life have been football umpires, and both really enjoyed the job. In one case it was Australian football, where the umpires need to run A LOT! Not sure if I’d be fit enough.

Side hustles I probably will never try

  • Medical experiments. A friend of mine took part in a few drug trials during their college years for a few dollars. She ended up getting a weird unexplainable rash from it. The compensation was small. I’m all for medical advancement, but not sure I’m ready to sacrifice my health.
  • MLM’s. Ever had a call from a friend who wants you to try a new product, and then start selling it too? I can’t fathom selling to my friends and family, no matter how good the product or service is. I know MLM’s work for some people, but they’re not for me :)
  • AirBnB my house or spare bedroom. One of the reasons my wife and I are selling our rental properties is to get out of tenant management and dealing with renters. No matter how much we can make, renting out our home brings on too much stress for what it’s worth IMO.

What do a lot of successful side hustles have in common? 

I think a few things. 

  1. Lucrative side gigs often exploit a unique skill or qualification a person might have, which usually allows them to offer services that demand a premium over minimum wage. Often that skill or qualification was gained from their primary job. 
  2. The side-gig often brings a benefit to a person’s primary job. This means that there are non-monetary benefits from the side-gig, like hands-on experience or widening your network, that are in turn leveraged by the primary job. 
  3. I think side gigs are often temporary in nature, like my pharmacist friend who worked toward a goal with her second job, achieved it, and then moved on.

FI people love the book “Your Money or Your Life” by Vicki Robin. Among other things, it discusses similarities between work and hobbies. One takeaway for me was that if you don’t consider getting paid, everything that you can get from a job can also be found in a hobby. That means passion, achievement, teamwork, socializing and serving others – all of these things can be found when you’re working for free!

So, are side hustles worth it?

I guess at the end of the day it all depends on your “why”.

Side hustles are a great opportunity to learn, follow our passions, and hopefully earn some extra $ on the side! But also, I often suspect that if we put that extra effort into our primary job or career development, we might be able to increase our primary income without a side hustle.

So personally, here’s my advice: if you need extra money and are looking for a side hustle, start by looking at your primary job. Can you put in the hours for a promotion or job change? Or is there a related service you can offer? Working in an area you already specialize in can lead to more income.

If not for money, think about your passions. Is there a way you can find casual work in this passion? If you never make any big money from your passion, will it still be time well spent? Probably!

Don’t forget – the world always needs more volunteers, and trust me there will be a rewarding role you can fit that is always worth your efforts.

Wishing you all a great week ahead, doing what you love.

– Joel

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  1. industrialbagels January 31, 2022 at 12:29 PM

    “AirBnB my house or spare bedroom. One of the reasons my wife and I are selling our rental properties is to get out of tenant management and dealing with renters. No matter how much we can make, renting out our home brings on too much stress for what it’s worth IMO.”

    If you’re still into real estate but are adament against the hassle of being a landlord I’d look into retail real estate. The leases there are for the most part NNN. All the responsibilites are passed onto the tenant and all you do is collect a fat check at the end of the month. 250 million dollar man Ben Mallah has a really good episode on this:

    Love, industrialbagels

    1. Joel January 31, 2022 at 5:34 PM

      Very cool. I’ve looked at some of these retail deals (as part of larger syndications) but haven’t seen one I really like yet. I’m still very much into real estate investing, just needs to be completely passive :)

  2. Jesse Cramer February 1, 2022 at 9:19 AM

    I can hear your silky Aussie inner monologue weaving its way through these pros and cons.

    Well explained and well written, Joel!

    1. Joel February 1, 2022 at 10:07 AM

      I might start a podcast.. my inner monologue has more random thoughts to share haha!

      Have a great week Jesse!!

  3. Accidentally Retired February 1, 2022 at 12:16 PM

    I agree with where you landed. Obviously “it depends” is the answer the question, but I don’t think you can go wrong with pursuing your passion as a side hustle. If it makes money, great, if not, no biggie.

    Really, this is exactly how I managed to turn my side hustles into selling two businesses. I started small, and good things happened. But even if nothing had happened, I loved what I was doing at the time, and that is really the key. If you are doing something you won’t regret, then it is worth it. If you already regret what you are missing out on in the moment, then I would ditch that side hustle!

    1. Joel February 1, 2022 at 3:18 PM

      We are very like-minded, AR… That’s why I enjoy reading your blog too! It’s more about the happiness and enjoying the time vs. extra money.

  4. Olaf, the Mile High Finance Guy February 1, 2022 at 2:29 PM

    I wonder if there is a correlation between side hustles and being childless, Joel? I would assume that those who are single or married, but without kids, have more time to devote to side hustles. Furthermore, once you have kids, I would assume that the trade off of time for extra money increases greatly, since you want to see them grow up. What do you think?

    1. Joel February 1, 2022 at 3:26 PM

      Interesting thought! I actually know a ton of busy parents that want a side hustle to keep the distracted, relaxed, and give them something else to focus on rather than just the family. Depending on the activity, it can be a needed break.

  5. IF - Impersonal Finances February 1, 2022 at 5:34 PM

    Very much depends on the gig, for sure. I know people can make money messing around with various apps or filling out surveys, but to me those are zero enjoyment activities that bring little in return. I try to avoid time sucks like that, but am open to

    Something in my personality just likes to find arbitrage opportunities and feel like I got one over on… someone. Not sure who. Maybe flipping houses is the final boss stage of this trait.

    And you’re being polite on MLMs haha.

    1. Joel February 1, 2022 at 6:10 PM

      The thrill of making a sneaky profit… I know it well! Sometimes I waste 2-3 hours flipping something for a $40 profit. Definitely not worth my time, but I just love doing it for funsies!

  6. KL February 2, 2022 at 2:12 AM

    Side hustles are good for people who enjoy them, don’t care about their job, have limited income or income growth potential or feel their main job is precarious. I’ve been left cold by the side hustle culture though – never seen the appeal.

    To illustrate my point of view, I’m working in an very well paid job in a domain I really like with both potential to advancement and pay raises. I make enough that a few percentage point raise will trump pretty much any side hustle I could come up with. Moreover, spending that little extra time in advancing my skills related to my job instead of dog-walking will have even better chance of higher pay (so I guess you could call that a job-hustle?). It also increases my overall skills and marketability, plus I find it fun.

    I do own investment properties and in fact also have a company on the side, just currently not spending much time on it. (The side company does exactly the same stuff I do at my day job.) But I guess from my point of view almost any side hustles are jobs I’d hate – I don’t want to walk dogs, I would never want to work in customer service, I cringe at the thought of being and Uber driver or grocery delivery person and I most certainly don’t want to start monetizing social media.

    I think people need to find stuff they like to do, whether it’s writing stuff on the internet, doing a “day job” in a domain that they find interesting, or walking dogs. But I don’t really see side hustles to be for me – unless you count that one day I might go out freelancing, in which case I’d just ramp up that side company of mine. (So I guess I’m inadvertedly anyway counted in the side hustle gang?)

    1. Joel February 2, 2022 at 10:23 AM

      So happy to hear that you love what you do and have opportunity for advancement. Sounds like you’ve already got the best of both worlds, so there’s definitely no point in hustling on something you don’t enjoy!

  7. Small Budget Retirement February 5, 2022 at 12:24 AM

    Great post. I agree with you and the side hustles. Sometimes it can even kill your passion if that’s what you’re doing as side hustle.
    I used to do wedding photography on the side and i gave it up. People want to hire you to shoot the engagement, a 12 hour event, an album, a house and the divorce for $500.
    Thanks for sharing those numbers. The first time I heard about NW was on this blog. At that time, it seemed to me unreal the idea of individuals like me even thinking about net worth; like that was reserved for just rich people. My credit cards were in the red, plus a student loan and all that.
    After becoming financially literate and working on my numbers for very few years I ust can’t believe what a difference it makes when you pay attention to your NW.
    We need these stories in front more people.

    1. Joel February 5, 2022 at 11:59 AM

      Maybe after you hit FI you could start up photography again and offer your services for free (but only to people that can’t afford big weddings)? Could be a good way to renew your hobby, help others, and have some fun in the process? just a thought!

      Congrats on your NW increases for 2020 and 2021!!!! I checked out your blog and love that you are documenting your journey! Have a great weekend :)