The Executive Suite: Moonlighting: 5 tips from entrepreneurs who've been there

It takes a special kind of person to willingly take on the stressors that come with moonlighting. Those passionate enough to launch their startup after putting in their hours at a typical nine-to-five don’t often regret it — but they do have some tales to tell. These tips from the trenches will help moonlighting entrepreneurs succeed in the long journey that is transitioning a night job into a day job.

1. Find a free office

“Understand the nature of the work you are trying to do and think about what is necessary for you to accomplish this work,” says 27-year-old Scott Dettman, a senior data scientist and PhD candidate in Milwaukee, Wisconsin. Those launching a startup might be intrigued by a trendy co-working space, but all that’s really needed are tables, coffee, food, outlets and Wi-Fi.

“You can swap out an office for a lot of different places. Being entrepreneurial means you are able to find solutions to relatively widespread problems and be creative,” he says. “Maybe you don’t need to spend the funds on a co-working space right away. Maybe you don’t need to spend the funds on a co-working space right away.”
Dettman works on his startup, VoxDel, with friends, so he simply looks for a place where they’d like to hang out like on campus, at a bar, in a park or at a 24-hour restaurant. “I don’t believe we need an office space — I look at that as a luxury,” he says. “I’d rather have one more sales person as opposed to having some great office.”

2. Make your day job work for you

While burning the candle at both ends is not ideal, there are multiple benefits to keeping your day job. For Jerry Lee of Los Angeles, his day job as a web developer eventually turned into a catalyst for his night job as founder of StoryLeather, an online retailer specializing in custom-made leather goods.

“Do something that is relevant to your day job so that you can build synergy between your day and night job,” Lee, 37, says. “For me, I engage on web development projects with companies that may become StoryLeather’s business partner or customer.”

Because of this synergy, Lee’s situation made a switch for the better: He now works on StoryLeather during the day and moonlights as web developer after hours.

3. Change up your environment

“Some days I felt like Superman,” says Vannessa Wade, an adult ESL teacher who moonlights as a public relations specialist. The 33-year-old entrepreneur from Houston, Texas, tried settling in a co-working space to get her public relations work done, but found herself needing a change of scenery.

“I’ve also frequented parks for inspiration, business centers, restaurants and coffee shops,” she says. But it turns out changing locations was beneficial for more than just idea generation and a chance to discover the city — it was great way to meet new people. “You never know who may need your services,” she adds.

Sites like Coffices.co can help you find places with free wifi in your area.

4. Work anywhere and everywhere

Advertising account executive Samantha Cole of Virginia Beach, Virginia moonlights as founder of Samantha Cole Digital Labs. The 27-year-old mother negotiates contracts outside of her son’s wrestling practice and runs content-planning meetings in the middle of a pedicure.

“I work mostly from my kitchen table, my car and on the go before work, during my lunch break and every night,” says Cole. “

I pack up each morning to leave the house with everything I need — for any client.

I pack up each morning to leave the house with everything I need — for any client.”
Cole also recommends keeping all appointments and deadlines written or typed up in the same place. “Don’t try to separate daytime life with nighttime life — you’re always working on all of them,” she says.

5. Network, network, network

For Asha, the 33-year-old who runs FoodLY during the day and publishes NOURISHED Magazine at night, the day is reserved for teaching cooking classes and offering personal consultations. Her early evenings, however, are reserved for writing at a co-working space in Manhattan, which allows her to network with entrepreneurs who are just ending their day.

“The aspect of networking does not exist when you go to a free space — there are benefits of being part of a community and it’s a lot more than just a desk,” she says. Solopreneurs can find co-working spaces especially useful as sounding boards. “It’s very important to meet people, get ideas and collaborate, even if you’re not working with them,” she adds.