5 Tips for Starting Your Side Hustle From Fashion Folks Who Did It

The #1 piece of advice? Just start.

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Whether it's a passion project, a way to "future-proof" one's career or simply an extra source of income — or a combination thereof — side hustles seem to be all the rage these days.

In an ideal world, we wouldn't even have to take on extra work or have a day job that isn't our true passion. Nevertheless, if you have an idea that feels worthwhile, now's as good a time as any to get the ball rolling. (Or not! No one should feel pressure to be productive with every moment of their day.)

Obviously, the pandemic has afforded many folks in the industry some extra time to pursue a new idea or take something they'd already dipped their toes into a little more seriously. It's also forced many of us to consider that our day jobs may not be as secure as we once thought. But having an idea and turning it into something real are two very different things. How do you make that jump?

To find out, we turned to three people from our extended fashion universe who did it, all while fulfilling the responsibilities of their day jobs.

Pre-pandemic, Vogue.com Senior Fashion Writer Liana Satenstein debuted her closet clean-out service, Schmatta Shrink, after she helped Sally Singer streamline her wardrobe. Word spread throughout Vogue and beyond of her closet-therapy abilities and, as we settled into our lives in quarantine, she started inviting fashion-industry friends onto Instagram Live for weekly #Neverworns, a sort of show-and-tell/interview hybrid where she advises stylish guests on whether or not they should keep certain rare designer goods.

Also pre-pandemic, Tembe Denton-Hurst, a staff writer at New York Magazine's shopping vertical The Strategist and former Nylon beauty editor, asked her aspiring-chef girlfriend Connay Bratton (a teacher by day) to make biscuits. She obliged, repeatedly, tweaking and improving the recipe every time. Denton-Hurst started inviting friends and family over to try the biscuits, recording their reactions — visual proof of the biscuits' overwhelming deliciousness — and then sharing them on Instagram. Her DMs quickly flooded with biscuit requests. She and Bratton did their first delivery drop at the very beginning of lockdown. They took a break for the summer, but then returned full steam ahead with Sundays Only (that's when they make and deliver orders), sometimes making, packing and delivering over 70 orders in one day throughout the boroughs.

Los Angeles-based fashion publicist Cory Sargeant started her side business, Lady Sargeant — through which she sold estate sale-sourced vintage jewelry on Etsy — five years ago, when she was working at an agency. She's since branched out and opened her own PR company, while Lady Sargeant has evolved to include hats and sweatshirts with her own artwork on them. Now, she's gearing up to launch a new product she's been working on in quarantine: Say It Do It, an aesthetically pleasing truth-or-dare-inspired card game "for the conscious gamer," as she puts it.

If you have a million-dollar idea or a hobby you'd like to turn into more, let them be your inspiration — and your guides. Check out their advice, below.

Just start

The most common piece of advice from those I spoke with was something that most entrepreneurs will tell you, but that doesn't make it any less true: Stop thinking about doing it and just start.

"This is the exact Schmatta analogy that I use — you can spend all day thinking about cleaning your room and [think,] 'Put that there, get rid of that thing, do The RealReal pickup,'" says Satenstein. "You can think about all these things and that's amazing but it's never gonna get done unless you do it so just do it. If it doesn't work, then great, but probably it will work if you just keep doing it."

Be passionate about what you're doing

There are two things are absolutely required for a side hustle, and those are time and energy. So, pursue something that naturally inspires you to turn off "Below Deck" and get to work during off-hours.

"You gotta really love it and have to be doing it for a reason other than, 'I just wanna start a business,'" Denton-Hurst explains. "You have to be clear about what you're doing, why you're doing it and just do it your own way."

"Listen to your body's response to it," advises Sargeant. "If it feels like something that you're really energized by and you have that force behind you... I find that I will make the time for something that lights me up that way."

"How can you dedicate time to something you're not passionate about it just doesn’t compute," Satenstein argues. "For this, I'm super passionate about it so all my energy comes naturally, which is crazy 'cause I've always felt low-energy just in general, but this is sort of a natural thing for me."

Get very organized

Energy isn't always enough to keep up with every task required of a day job and a side hustle — organization is key.

One thing that works for Sargeant is treating her own brand as she would one of her PR clients. "Each morning I write down each client and what work I need to get done for the week, so I added in Lady Sargeant," she says. "That's really helped me stay on track, having more structure around it, because I was finding at the beginning I wasn't putting enough time into it." Sargeant does have the advantage of being self-employed and thus having some flexibility with how she chooses to structure her day or week.

"I bought a whiteboard," Satenstein tells me with a tone of disbelief at her own purchase. Juggling multiple gigs has forced her to get "hyper organized," she explains: "This is not me at all. I'm not a white board girl, I'm a girl who writes on a napkin and loses the napkin and finds it a month late in some pocket. I had to buy a whiteboard to keep myself organized and updated, both for Neverworns and for Vogue." She uses it for to-do lists, scheduling, keeping track of receipts. "Actually, everyone should have one; it's kind of a life changer," she adds.

For Denson-Hurst, keeping track of orders — which she takes via Google Forms — and planning delivery routes require the biggest use of her organizational skills. Luckily, she's used to juggling a lot of things. "If I'm not doing 100 things at once I'm like, what am I doing?" she admits. "Adding yet another task on my list of never-ending things didn't seem odd to me. I love to manifest my passions into various things so it's just always like this."

Lean on your community

While Satenstein's and Sargeant's side hustles are independent, solo endeavors — and Denson-Hurst works only with her partner — they've all leaned on their networks for support.

Denson-Hurst says it was having an engaged community of food-loving Instagram followers that gave her and her partner an advantage with launching Sundays Only. "I had already built up a community in a sense because we had been posting these videos — I didn't have to convince people about the biscuits because they were growing their own little cult following," she explains. "Someone who's starting a new business, I would say focus on community."

With Satenstein, her Schmatta Shrink customer base started with coworkers; for Neverworns, she tapped a digital community of fashion friends as guests. With Say It Do It, Sargeant wanted to take things "a little more seriously" than she had past projects, hiring people for things like graphic design and copy editing plus asking friends to play "mock games," which helped smooth out any kinks with the way questions were phrased or confusion around the instructions. She's also planning a photo shoot in collaboration with a creative-director friend of hers where her sister and friend will be the subjects.

"I definitely started with reaching out to my community and I have a lot of talented friends that I've helped over the years with different things, so it's been fun to reach out to them," Sargeant notes.

Expect challenges and mistakes

It won't all be smooth sailing. Denson-Hurst and Bratton have struggled navigating the complexities of scaling a food-delivery business. After trying to coordinate 45 deliveries in New York City in one day, it became clear that that part of the business would ultimately need to be outsourced.

"It's quickly becoming like, oh, this is getting complicated for us to just run around on our own," she explains. "Finding a delivery service that can do what we're trying to do has proved to be difficult but we do want to make it a real thing."

Already, they're spread pretty thin on the weekends on which they do Sundays Only. "We sleep probably between us six hours total [all weekend]; she's waking up at 3:00 a.m. to bake because she wants them to have the biscuits fresh," Denson-Hurst adds. On Valentine's Day Weekend, she made over 500: "It's an incredible amount of biscuits for a small place, but you're also not making enough money to where renting out a kitchen makes sense. It's complicated because you're trying to figure out how to have as many people as possible experience this while also trying not to go crazy."

Something else that can be time consuming is running social-media accounts. When you're starting out, it might be best to keep things simple there.

"I can't get fancy and post photos of Queen Elizabeth eating a biscuit and being like, 'biscuit vibes,'" explains Denson-Hurst, who mainly uses the Sundays Only Instagram to announce drops. "I just don't have the mental capacity to do social in that way."

Another common challenge is money. Obviously, everyone's financial situation is different, and so is the amount of overhead required for any given side hustle. Schmatta Shrink and Neverworns are pretty low-overhead projects; Satenstein will charge clients for the former on a case-by-case basis, particularly if she has to hire an assistant and haul things away herself. Sargeant is spending a little more on the card game than she had on other projects and says she's been putting a little money towards it each month.

A general rule of thumb, per Denson-Hurst: "Do what you can with what you have."

Homepage photo: Fernanda Calfat/Getty Images for NYFW: The Shows

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