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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