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Advice / Career Paths / Exploring Careers

3 Steps You Need to Take to Actually Start a Side Hustle

Crea co-founders at launch event

You’ve heard it before, probably many, many times: If you’re passionate about what you do, work will never feel like work. But, what if your passion doesn’t completely align with your day job? Enter the side hustle—a gig you work on outside of your full-time job that fulfills whatever you’re passionate about.

That’s why Erin Petree, Circle Strategy and Operations Manager at Squarespace, started Crea with two friends. Crea (cray-uh) is a content publishing platform showcasing the work and stories of artists, architects, and designers with the intention of making their work more accessible.

“We’ve always worked in creative fields and consider ourselves 'creative laterals,' so we’re really excited to deepen that relationship supporting these people [designers, artists, and architects] with Crea,” Erin says.

But, starting a side gig isn’t as easy as creating a website, especially when you’re jumping in with both feet. And to be clear, having a website is paramount for most side hustles. It's not only where people can find and learn more about your business, but in some cases, like Erin's, it is the business. That’s why Erin gave us the dish on her best advice for getting a side hustle off the ground. Read on for her tips and experiences.

1. Find a Support System

Whether you’re looking to start a business with a like-minded friend, or planning on going solo, having a group of people that you can vent to or ask for guidance is key to making any venture a success.

In Erin’s case, having co-founders was paramount to getting Crea up and running. Like any good side hustle, Crea was born over a few glasses of wine, where Erin and Kate McTigue, Co-founder of Crea and Creative Strategist at NR2154, discussed their shared passion for supporting creatives. So, while many people go it alone, Erin suggests finding a partner you really gel with.

“I fed off Kate's energy," she says. "You have to be obsessed with each other to make something like this work.”

But if you do choose to fly solo, surround yourself with people you can talk to, bounce ideas off of, and get genuine feedback from. Scour your network for people in the same industry, reach out to mentors, and even ask close friends or co-workers for their honest opinions. From there, ask to be put in touch with other entrepreneurs and start connecting with people who are doing something similar to you.

2. Carve Out the Time

Another reason to make sure you have a support system in place? For the mornings (or nights) that you need to work on your side hustle, but maybe aren’t feeling the most motivated.

It shouldn’t come as a surprise that starting a side hustle will require a lot of, well, work on the side. We’re talking early mornings, late nights, and weekends spent finding time to dedicate to your new venture.

For Erin, Kate, and their third co-founder Meena Lee, whose day job is in Experiential Marketing and Site Activations at Industry City, that meant a standing coffee date at 8AM on Tuesday mornings, plus nightly solo work sessions, and regular blocks of time on Saturday mornings.

“Having a side hustle when you’re fully employed, that time doesn’t come out of nowhere, you’re taking time out from other things,” Erin says.

So, schedule time to work on your project. If you’re a morning person, maybe you have to forgo your morning run two days a week and work from 6AM-8AM. If you thrive at night, that may mean skipping dinner with friends and holing up from the time you get home from work to when you go to sleep.

And something that worked well for Erin and company was planning mini vacations or off-sites, where they had uninterrupted, extended time to work on Crea. They went on one in the very early stages where Erin and Kate worked on refining the idea, brainstorming their ideal audience and user personas, and creating a social media strategy. Then a bit further down the line, they had a second offsite to decide on a name.

“We took MetroNorth to Cold Springs, NY, stayed in an old, rickety attic in a house overlooking the Hudson River, and plastered the room in post-it notes,” Erin says.

3. Cover the Basics

After you have the idea fully fleshed out, it’s time to make it into a reality. Ensure your chosen name can be trademarked and there is a domain name available, then get started building your website. On Squarespace’s all-in-one platform, Erin registered the domain name and created the website in a weekend.

“I’ve built a fair number of sites so it was a no brainer to use Squarespace, but we also chose it because of the brand consistency, how your aesthetic is continued on every page,” she says.

Other Things to Remember When Starting a Side Hustle:

Secure social media handles

Have a distilled brand message and design

Consider having a newsletter sign up, creating an LLC, and trademarking your company name

...then launch! For Erin, Kate, and Meena it took just about 12 months for the whole thing to come together. Putting in the work upfront ensures (relatively) smooth sailing once your business is out in the world.

Starting a Side Hustle, A Timeline:

Months 1-3: Ideate. Decide who you are as a brand. Lock in your messaging and ideal audience. Go through the technical requirements of setting up a website and creating social media accounts.

Months 4-6: Put your pen to paper and design your brand.

Months 7-9: Get set up. Think about things like: a newsletter subscription, trademarking your name/logo, getting an EIN so you can write and receive checks, and establishing an LLC or sole proprietorship.

Months 10-12: The final launch cycle—this is when everything comes together. Tie up any loose ends, and get ready for launch so post-launch everything can run on its own, and is very organized.

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