Everyone’s had one… or at least it feels that way.
We’re talking about the side hustle – freelancing after work, running an Etsy shop from your kitchen table, consulting on weekends, or quietly building something bigger in the background.
On this episode of Behind the Brand, Taylor, Kelly, and Mo Moxie sat down to talk about their real experiences with side hustles: the wins, the burnout, and what hustle culture looks like now. This blog recaps that conversation and pulls out some takeaways for small business owners, solopreneurs, and creatives who are trying to decide if a side hustle actually fits their life (and their energy).
Why Did Side Hustles Become the “New Normal”?
According to Kelly, the whole idea of side hustles really exploded with millennials.
As a Gen X-er, she remembers a time when you got a job… and that was your thing. You showed up, worked hard, and maybe someday started your own business. There wasn’t the same expectation that everybody should have “three different streams of income” and a brand on the side.
Some of the reasons side hustles took off:
- The Great Recession & financial insecurity
A lot of millennials watched their parents struggle through layoffs, shrinking retirement accounts, and general instability. That kind of financial trauma sticks. Having a side hustle feels like a safety net. - Wage gaps & cost of living
In many fields, people simply weren’t making enough to feel stable. A side hustle became a way to add an extra $200–$500 a month just to breathe a little easier. - The rise of online work
With social media, e-commerce, and remote tools, it suddenly felt possible to sell almost anything from anywhere: coaching, content, templates, handmade products, virtual assistant services… you name it.
Add in a lot of content from financial “gurus” telling people they should have multiple income streams, and you’ve got the perfect recipe for hustle culture.
The Upside: When your Side Hustle Actually Fills your Cup
At Moxie, we’re not anti–side hustle. In fact, all three of us have had them.
For Mo, design is both his career and his happy place. Before joining Moxie Creative, he spent a lot of time freelancing and building up a portfolio. Even now, he’s had clients from years ago who still love working with him and want to keep collaborating.
For Kelly, creative work outside of “official” work tends to take the shape of:
- Interior design and event design
- Decorating and styling spaces
- Craft projects she could sell, but usually just keeps or gives away
Most of that doesn’t happen for money – it’s more of a passion project that still feeds into her creativity as a marketing agency owner.
For Taylor, side hustles started because she wanted:
- To make more money, and
- To do work that actually felt creative and fulfilling.
She tried a few paths:
- An MLM right out of college (hello, skincare obsession)
- Social media management before it was a widely recognized role
- A handmade shop selling pacifier clips, teething rings, and wristlets
Some of those ventures didn’t make much money (or even lost money), but they gave her something important: a creative outlet when her full-time job wasn’t cutting it.
Taken the right way, a side hustle can:
- Fuel your creativity
- Help you build a portfolio
- Introduce you to new people and opportunities
- Let you experiment with a business idea before going all-in
- Give you something that is just yours when your day job feels draining
And sometimes, like it did for Kelly’s husband, a side hustle becomes your full-time business.
The Downside: Burnout, Split Focus, and Doing too Much
Here’s the part we don’t like to glamorize: side hustles can also stretch you way too thin.
Kelly summed it up simply:
“Why do we have to do so much all the time?”
She once tried to run an interior design store on top of working full-time. On paper it sounded exciting. In reality, it felt like running two businesses. She was exhausted and didn’t feel like she was doing well in either space.
Mo has felt it too. Between a full-time role at Moxie, teaching in the past, two little kids, volunteering, and the occasional freelance project, it got to a point where there just wasn’t enough time or mental bandwidth.
Some of the biggest cons of side hustles we see:
- Burnout
Working all day and then logging on at night to do the same type of work is a quick way to lose your spark. - Split attention
Two jobs = two sets of deadlines, two sets of clients, and two sets of expectations. Something will eventually suffer. - Money that doesn’t math
By the time you buy supplies, pay for software, ship products, and give up your free time, you might discover you’re actually losing money on what was supposed to be your “extra income.” - Feeling like you have to hustle
It’s one thing to do a passion project because you love it. It’s another to feel like you’re failing if you’re not always monetizing every spare moment.
That’s where the hustle culture myth starts to crack. Working more doesn’t automatically mean you’re winning.
Hustle Culture, Generational Trauma, and “Being Enough”
A big thread in this conversation was how much money stories and generational expectations shape our relationship with side hustles.
For Taylor, there was pressure (spoken and unspoken) to be the kid who doesn’t ask for money, who makes her parents proud by “doing everything right.” Hustling, taking on more, and finding ways to earn extra income felt like part of that.
For Kelly’s husband, growing up with scarcity meant he’s constantly watching the bank account, always thinking a step ahead financially. Side projects, cooking for events, and extra work are partly rooted in not wanting to go back to that feeling of not having enough.
Those stories are real. But so is this reminder:
You can hustle at one job. You don’t have to hustle at two.
The culture of “just work harder and you’ll be fine” is breaking down. After COVID especially, a lot of people realized how little joy there was in running nonstop with very little payoff. Many chose to intentionally step back from their side gigs and refocus on rest, family, or one solid, sustainable path.
So… Should you Start a Side Hustle?
Side hustles aren’t inherently good or bad. They’re tools. The key is how (and why) you use them.
If you’re considering starting or continuing a side hustle, here are a few questions to ask yourself:
- Is this a business or a hobby?
If it costs you more than it makes you – and you’re okay with that – call it what it is: a hobby you love. That’s allowed. - Is this filling my cup or draining it?
Do you feel more energized and inspired after working on it? Or constantly tired and resentful? - Is it aligned with my long-term goals?
Are you using it to build skills, a portfolio, or a future business you want? Or just saying yes because you feel like you “should” be doing more? - What are my boundaries?
How many hours a week will you realistically commit? What types of projects will you say no to? What happens if your full-time job or family needs more from you? - Can I try it and ditch it if I need to?
You’re allowed to experiment. You’re also allowed to walk away when it no longer serves you.
At the end of the day, our take is this:
If you want a side hustle, be intentional.
Set clear parameters. Try it. And don’t be afraid to let it go.
Where Moxie Fits into your Side Hustle Story
Whether your side hustle is becoming your main gig, or you’re an established small business tired of wearing every hat, you don’t have to do it all alone.
At Moxie Creative, our team (yes, including Kelly, Taylor, and Mo Moxie) helps:
- Side hustlers who are turning their idea into a real brand
- Small business owners who want to step out of hustle mode and into a sustainable marketing strategy
- Nonprofits and local organizations who need strong branding without burning out their staff or volunteers
We handle the branding, design, websites, and marketing strategy, so you can put your energy back where it belongs: serving your clients, customers, and community.
Tune In and Get Inspired
If you loved this convo (or even mildly tolerated it), give the full episode a listen. And if you’re ready to stop hustling alone and start building a brand with actual support? Moxie’s your team. Let’s make cool things together.
