9 Principles For Starting a Successful Side Hustle
Illustration by Sonny Ross

Many of us have pipe dreams of starting a side hustle for extra cash or just for fun. At the beginning of the process, it’s easy to succumb to overwhelm — to quit rather than to navigate a tangle of unknowns that accompany launching a new project and balancing two jobs.

There’s not one road to success for side hustlers, because passion projects can be so diverse, from dog-walking to opening an e-commerce shop. But there are some uniting principles that can serve as guardrails, no matter the road you’re on.

We spoke to 12 customer support pros to get the scoop on how they navigate everything a side gig brings along with their full-time jobs. Here are the nine principles that helped these professionals build a multi-hyphen career in — and beyond — the industry we love. Learn from them, and there’s nowhere you can’t go with your day job and your side hustle.

1. Know your “why”

Understand the heart behind the hustle

Chanita Simms People Ops at Help Scout; CEO of Melanin.Tech

In Chanita’s first role at a tech company, she struggled with the obvious lack of diversity and inclusion at the company as an African American woman. “I remember feeling very lonely most of the time, which stopped me from bringing my full self to work,” she says. “I couldn't find exactly what I was looking for, so I created a platform in hopes of preventing others from going through what I did.”

Soon, Chanita had founded Melanin.Tech, a community-based platform that empowers people of color in tech to learn skills, find job opportunities, build relationships, and boost diversity in the industry one job at a time. In her role as CEO, she guides a small team as a leader, which differs from her role as an individual player at Help Scout.

Switching back and forth between “player” and “coach,” all the while facing down the same systemic shortcomings she experienced in tech, requires deep emotional labor. Her recommendation? “Figure out your ‘why’ before you start. If it's for recognition, fame, or money, don't bother. But if it's because you have a vision of what a better world could look like, and you want to help it get there, go for it!” When bringing such big change into the world, you need help, too. She adds: “Also, get a therapist. It helps. Trust me.”

As for the overlap between her full-time role and side gig, it all comes down to empathy and advocating. Not only does Chanita credit support with strengthening empathy, she believes it has taught her how to problem solve, fight for what’s right, manage her time, and unapologetically ask questions when she needs more information.

Marco Yim Manager of Customer Success at inkbox; CEO at Extempra Toronto, Canada

Marco Yim founded Extempra, a communications training company, while working full time in support. Through his side gig, he helps professionals learn to speak with authenticity and credibility through one-on-one coaching and interactive workshops.

He didn’t have to look far for examples of great communicators. “Customer support folks are among the best communicators in all kinds of scenarios. We need to adapt and be able to stay authentic, show empathy, or explain complex things clearly. These skills are ones that I think a lot of people outside of our industry want to be great at,” says Marco.

When Marco took public speaking trainings at a former employer, he noticed they weren’t very effective at teaching teams how to communicate. He started developing a proprietary model that focused on self-discovery to help people shine in interviews and leverage public speaking skills for professional growth.

But before he even started articulating Extempra’s mission, he took the time to set a clear foundation. He shares: “I took a lot of time to develop my craft, do workshops for free, iterate on my services, and hone in on the things that made me really excited.”

Marco believes that being intentional should extend to considering the role the business will play in your life. “Are you hoping this will be your next career move, a passion project to develop your skills, or a way to earn some pocket money?” The answer will help guide you in a clear direction.

2. Choose joy

Invest in work that loves you back

Kirsten Penaloza Customer Experience Lead at Ellevate Network; founder at Bodhi Leaf Shop NYC New York, New York

Kirsten Penaloza works out of Ellevate Network’s New York City office (and sometimes, from her home in Queens) as a Customer Experience Lead. Helping customers every day taught her the value they bring to every aspect of a company: “They are the best marketing tool you have — and their feedback comes for free!”

When she came across a surprising fact — that many vegan and natural skincare products include potentially harmful chemicals and wasteful packaging — Kirsten saw an opportunity to combine her natural inclination to serve customers with a long-standing love of cosmetics. She started making vegan and natural skincare products, including lip balms, face toners, and serums – all of which she’s infused with Reiki energy. With each product, she includes “lucky charms” that inspire self-love and strength.

Working evenings and weekends with her hands while imagining how her products make other people happy grounds Kirsten every day after the intellectual work of customer support. “I gained a whole new self-esteem thanks to what I do, and I discovered skills I never thought I would have,” she says.

Kirsten hopes that self-esteem extends to her customers through each experience with her products. “When I started to work on building a positive mindset, I discovered how many people, especially women, perceive themselves as ugly or they hate their bodies. I wanted to change that, not just for myself but for others,” says Kirsten. “I hope to share a positive message with my lucky charms and contribute to other people's well-being and happiness with my products — it’s the most rewarding thing ever.”

Denise Twum Support Process Manager at SmugMug; owner at Nisey Knits San Francisco, California

In 2006, Denise Twum began knitting for fun. Her former supervisor taught her the craft, and years later, she launched her business designing and creating knitwear at Etsy — all while eight months pregnant.

Although Denise’s day job as a Support Process Manager often gets priority, she pencils in times to get creative around her schedule. Because it’s seasonal (work picks up before the holidays) she has a natural ebb and flow, so it’s not constant. Plus, she tries to outsource non-knitting aspects of Nisey Knits like bookkeeping and social media management, which cut down on admin time.

Ultimately, knitting is a form of self-care she gets to share with others. “Sometimes, I just pick up a ball of yarn and imagine all the things I can create with it, and that is enough to soothe me. Other times I may need to knit a few rows in order to get that sense of calm.” Sharing her handmade products with others is the icing on the cake, and her thriving business pulls heavily on her customer-first ethos (as shown by her 54 five-star reviews on Etsy). Over the last nine years, Denise has gained the respect of fellow knitters, too, publishing her knitting patterns in magazines and on Ravelry.com.

But the most striking thing about Nisey Knits is how it nurtures rather than inhibits work-life balance. “My side gig is my built-in relaxation therapy. I knit while traveling, and I also listen to audiobooks while knitting, which is a twofer,” she shares. Denise recommends choosing a side gig that enriches your life – and to give it a year before finding a different path if it’s not the right one for you.

3. Challenge yourself

See growth opportunities everywhere

Maria Górska Happiness Engineer at Automattic; columnist at Kosmos Dla Dziewczynek Warsaw, Poland

Kosmos Dla Dziewczynek, which translates to English as “Cosmos for the Girls,” is a Polish magazine that educates and supports children, particularly girls. When Maria Górska, a Happiness Engineer at Automattic, saw the publication’s Kickstarter campaign, she was so enthusiastic that she purchased a sponsor package that included a meeting with the editor.

The serendipitous encounter opened a new door. She explains, “I had previous experience with teaching kids to code, and I asked if they needed someone to write about coding. As it turned out, the person who was supposed to do it had just resigned a few days before. That’s what you call a cosmic coincidence!” Maria now serves as the science and tech columnist, writing about anything from space exploration to genetics and algorithms. Each column includes a puzzle or riddle that needs to engage children in a big age range — something that challenges Maria every time she works on a new piece.

Beyond her role as a columnist, Maria also helps the editorial team brainstorm the direction and voice of the magazine as a consultant. The best part is how connected Maria feels to the team’s mission. “It’s the voice of courage, empowerment, and wisdom I wish I had around me as a kid, in a world that is mostly obsessed with appearance,” she shares. “I’m grateful I can help deliver that message to thousands of children everywhere in Poland.”

Writing about complex, technical topics for the magazine not only brings her meaning, it has made her day job easier. “It’s impossible to write for kids without clarity and deep understanding of the topic — they can call out a bluff like no one else. The more I practice writing for kids, the better I become at communicating complex technical solutions to our customers.”

4. Build community

Learn and share with others

Craig Stoss Director of Platform Support at Arctic Wolf; founder of Technical Support Innovators P2P Waterloo, Canada

Craig Stoss belongs to a tech hub called Communitech based in Ontario. The group helps tech companies succeed — something Craig knows a lot about as the Director of Platform Support at Arctic Wolf Networks and a writer with Supported Content. Communitech often facilitates meetups, but Craig noticed one day that they didn’t have one for support.

He partnered with the wider Communitech community to develop a technical support group, booking venues and speakers alongside his co-leaders. “My reward is that I have become a stronger leader through learning different perspectives, have become a better presenter through speaking at our events, and have grown my network with some incredibly talented people who I can rely on for advice or just a social chat over a coffee or beer,” he says.

To get there, he had to be willing to step out of his comfort zone and build those connections from scratch. His best advice: “Approach people you might not have before. I have never been rejected when I've asked a leader out for a coffee to chat. Most people want to share their knowledge and learn from others. Doing so will help you to build a network, that once large enough is a great catalyst to make a consistent meetup such as this one,” says Craig.

Ultimately, Craig believes that no one’s challenges or problems are unique. Learning from each other is the key to creating an ecosystem that supports growth for each support pro, their company, and their customers.

5. Leverage technical skills

Apply support experience in new ways

Aaron Sachs Customer Reliability Engineer at Sensu, home brewer Chattanooga, Tennessee

In his own words, Aaron Sachs “makes Sensu customers look like badasses to their customers.” Through training, support, implementation, and product documentation, he supports a product that can monitor everything, but particularly IT infrastructure and applications. In his prior job, Aaron felt himself edging toward burnout. A mentor suggested he pursue a hobby, so Aaron took a week off and learned how to brew beer at home.

Four years later, he’s still doing it. “Ultimately, I love brewing because it was a salvation of sorts. When I was burnt out, I was becoming a bit of a bear, and I didn’t like who I was becoming,” says Aaron, “Homebrewing encouraged me to step away and have something to focus my energy on that’s not answering tickets, writing technical documentation, or consulting on an implementation.”

That didn’t mean he was leaving his tech skills behind. “In the course of home brewing, I decided to mix what I do professionally and use Sensu to monitor my kegerator. So it’s monitored for things like temperature changes, whether I leave the door open, and how much beer I have left in the kegs (still a work in progress). I’ve got fancy graphs that I can now look at and get some visualizations for the data, so that’s been fun,” says Sachs.

If you’re thinking about home brewing, check out his blog and Sensu beer-tracking docs. It takes less than the cost of a 12-pack of craft beer to get started, but don’t do it alone. The process (and the product) are meant to be shared, so get your friends and family involved, too.

6. Prioritize flexibility

Scale up or down as needed

Lance Conzett Business Operations Manager at Postmates; Freelance Journalist and Photographer Nashville, Tennessee

Lance Conzett works as Business Operations Manager at Postmates, where he leads the Customer Experience Tools team. As Lance puts it, “We support our support teams through technology, process management, and clever problem-solving.” Outside of his day job, Lance works as a freelance journalist and photographer in pop culture and music in Nashville.

He got his start writing reviews and news about punk bands as a teenager and taking photographs with a $50 lens. “I've interviewed tons of interesting people about the art that they create—folks like Aziz Ansari, William Shatner, ‘Weird’ Al Yankovic, Josh Ritter, Craig Finn from The Hold Steady, Greg Gillis from Girl Talk, and many, many more,” says Lance. “I've also shot over 600 different bands and more than 50 venues, including festivals like Bonnaroo, South by Southwest, and Forecastle — everything from Elvis Costello to Kendrick Lamar to local punk bands with names like ‘Diarrhea Planet.’”

Lance credits his work in support with strengthening problem-solving skills that make for great concert photos:

“Concert photography is kind of a problem to be solved — there are things you can't control (the band, the lights, the crowd), which means that it's completely on you to figure out where to move, what lens to shoot with, and what settings to use, and to solve the problem while everything around you keeps moving. Support helps you learn how to keep the plates spinning because nobody's going to stop for you.”

The dynamism that flows through Lance’s moment-to-moment work as a photographer also translates to his balance as a professional with two thriving careers. He can pick up the camera when he’s craving a creative outlet and put it down when he’s busy at Postmates. “The main thing is knowing that I don't have to do the extra work,” shares Lance.

7. Plan for seasonality

Request PTO during busy seasons

Rhoda Meek former Director of Customer Service, now Product Manager at Olark; crofter and farmer Isle of Tiree, Scotland

Rhoda Meek lives on the remote Isle of Tiree off the western coast of Scotland. Although she didn’t grow up on her family’s croft (a small Scottish farm), Rhoda always wanted to make it her permanent home. Rhoda’s childhood dream came true, and she intentionally pursued a career in support, knowing it would offer great remote opportunities that would complement her work on the farm.

She recently transitioned from Director of Customer Service to Product Manager at Olark. “I loved the challenge of leading a team — but I think the best bit was watching a team grow into an incredible group of natural leaders who were going to be just fine when I moved on into a new role,” says Meek.

When Rhoda’s not working at Olark, she’s raising sheep, ducks, and hens while managing a small market garden with a neighbor on her family farm. She’s written a farmers series for Olark’s blog about the unexpected crossover between customer support and crofting. She says the hardest part is when there are unexpected emergencies in either role that make the normal day-to-day in her other job seem impossible. That’s especially the case during lambing season when the circle of life starts again, and she often has to make heartbreaking decisions on the spot. Rhoda recommends that anyone who raises sheep (or has a seasonal side gig) proactively take time off during these unavoidably busy times.

And even when she has a full plate with both roles, she advocates for finding your peace. “When I do need some time away from everything, I go fishing in my wee boat and rock to and fro in the waves with a sandwich and a coffee — just me and the sea,” she says.

8. Create a schedule

Stay organized to maximize your time

When Mercer Smith began working remotely in support, she felt lonely. She thought yoga could be a great way to be around other people while giving her the opportunity to wind down. Five years ago, she felt inspired to take the next step and invest in yoga instructor training. Since then, she’s been balancing her full-time support career with a thriving yoga practice that has continued to evolve with her interests.

In her spare time, Mercer now teaches yoga and leads teacher trainings, guides people through meditations and moon circles, serves as a corrective exercise specialist for both pre- and post-partum parents, and still manages to serve as a support consultant, writer, and a single mother to a toddler.

Mercer’s practice as a teacher and guide fulfills her spiritual side, while her role as Head of Support at Appcues nurtures her drive. Both positions revolve around helping people; the contrast and overlap between responsibilities is ideal. “I love seeing people who are where I used to be and helping them to realize their goals in personal growth. In that way, it's very similar to support — most of my side hustles focus on helping people get better at the things they want to get better at,” says Mercer.

Mercer finds that a rigorous personal schedule gives her the freedom to fulfill these jobs while taking care of herself. “I definitely am all-go between 6 a.m. and 10:30 p.m. (when I go to bed), but not all of that ‘going’ is specifically work or productivity-related. While it means that most of my time is technically booked up on my calendar, some of those slots are for things like reading for 45 minutes a day, or spending time with my son in the morning and evenings,” she says. Follow Mercer’s lead and book yourself in for things you love.

9. Don’t limit yourself

Leave behind the myth of “one” career

Liz Sherman Director of Expert Support at Teikametrics; owner and head baker at Boston Frostin’ Boston, Massachusetts

Liz Sherman started baking with her mom at age three, and she transformed her love of the craft into a business 19 years later when her aunt asked her to bake six dozen cupcakes for a graduation party. Although she took a hiatus from baking while working in NYC, after moving to Boston, Liz launched Boston Frostin’, a gourmet cupcake company.

She also works as the Director of Expert Support at Teikametrics and reserves baking for her off hours. Time is the biggest challenge, and sometimes she ends up sacrificing nights out with friends or weekends to bake. As her business expanded and she worked more hours baking, Liz learned something unexpected: she didn’t want to leave her support role. “By pursuing your side passion, you'll realize if that's what you should be doing full time, or if doing it on the side fulfills that passion enough for you,” says Liz.

Liz’s side gig has not only affirmed her career in tech, it’s deepened her connection to the Teikametrics’ customers. “Being an entrepreneur myself gives me extreme empathy for my software customers. I've historically supported customers from small, entrepreneurial, oftentimes scrappy businesses — my job is to help make them successful,” says Liz.

Tory Corless Deputy Director for Admin Support at ActBlue; singer with the band VQnC Somerville, Massachusetts

Tory is a multi-talented artist, vintage clothing seller, and photographer who just released her band VQnC’s debut album, Freedom, in April 2019 — all the while working as the Deputy Director for Admin Support at ActBlue. Growing up, she watched her parents balance full-time jobs with performing in professional music groups, which gave her a framework for pursuing a multi-hyphen career. “They definitely impacted the way that I saw ‘adulthood’ and having the capacity to have multiple passions at once,” says Tory.

Tory describes VQnC as a nu-disco project that has distinct bass lines, catchy melodies, and meditative repetitions that celebrate self-care, self-love, and natural imperfections. Writing and performing music gives Tory the chance to explore the intersection of those ideas within her own life while inspiring others to do the same.

Like support, music is a people-focused industry where organization and communication are key, especially because Tory acts as her own manager and booking agent. The crossover skills go both ways: “While my role in support isn’t centered in the arts, I still find ways to bring my creativity into the workplace as I love solving tough questions by thinking outside the box and using creative solutions. Also, my energy is undoubtedly creative so bringing that into the office definitely shakes things up for the better.”

Some people assume that Tory is working to transition to music (or fashion) full-time. But that’s not the case. “The thing is,” she says, “I love being able to do multiple things at once and being able to express all aspects of myself on a daily basis. This is what makes me ME!”

Every side hustle starts with an idea

This group of diverse, inspiring customer support pros all began their passion projects with an idea, and look where they are now! Starting your side hustle can be as simple as following a hunch or solving a problem. By applying your support skills to a new project, you can leverage everything you’ve learned to serve your dreams — and a new community — in a powerful way.

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