How to Start a Side Hustle: Take the First Step

The first step to starting a side hustle is the scariest, toughest, and most necessary. Here's how to get going.
How to Start a Side Hustle: Take the First Step
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CEO of Perell Ventures
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This story appears in the March 2021 issue of Entrepreneur. Subscribe »

I started my first side hustle at my kitchen table more than 20 years ago. At the time, I was broke, inexperienced, and overwhelmed.

Where to begin? The answer is so simple that it’ll sound stupid: You make the decision to begin. Everything stems from a commitment to take the first steps. You can make excuses all day — too busy, too tired, too cash-strapped — but remember than nearly half of U.S. workers already have some kind of side hustle. They have struggles, too. But they’re pushing ahead. Here are the steps that helped me get going, and that can help you, too.

Related: Moonlighting Your Way to Millions: 4 Tips to Turn Your Side Hustle into a Successful New Business

Step 1 Ask these questions.

It’s important to find a side hustle that is a good fit for your skills and lifestyle. Ask yourself this…

→ How much time can I dedicate to this? Establish this up front and commit to it.

→ How much income do I need to make this worthwhile? This isn’t a goal; this is a reality check. Be realistic about it, write it down, and refer to it often. You’ll want to know if your time is being well-spent.

→ What skills do I have that can make this work? Don’t know? Ask a friend what they think you’re good at. Shoot to create a list of three.

Step 2   Create a structure.

Some people hate structure. Maybe they dream of being an entrepreneur so they can escape the structure of their jobs! But I’m telling you: Structure is freedom. It’s the ground that you build upon. Here’s how to create it:

→ Set a goal. I like to make SMART goals — specific, measurable, attainable, relevant, and timely. Each element is critical. You need goals you can work toward, and that you can track your progress on. Once you know this, you’ll start to have a sense of what’s required to get there.

→ Create a schedule. If you’re committing 10 weekly hours, put them in your calendar and stick to it.

→ Find your tools. There are many platforms and services that can help you launch. Take a look at places like Upwork, eBay, Etsy. Start offering your product or service, and learn your marketplace at low risk.

Related: 9 Lessons From 9 Years in the Side Hustle Trenches

Step 3   Foster great relationships.

When starting anything new, it’s helpful to surround yourself with people who have walked in your shoes—and even better if they are a few miles ahead of you! Search for two kinds of people:

→ Mentors. A mentor isn’t a job description; you don’t need people who agree to some formalized role. Instead, build a network of mini-mentors — friends or former colleagues who have expertise and insights.

→ Accountability partners. Find someone who’s on a similar path as you, and buddy up. You can help each other stay on track. When you’re your own boss, it’s helpful to keep up with other bosses.

Now comes the most important part: Instead of questioning yourself or waiting for the perfect moment, it’s time to go. Everything that comes next will help you grow.

How Three Side Hustlers Did It

Find (Free) Marketing

“In February 2020, I launched a line of functional chewing gum, made with plant-based vitamins and adaptogens. I don’t come from a family of entrepreneurs, so I didn’t know what being an entrepreneur should look like. I come from an immigrant family, and I’m 40 — so my parents were confused about why I would take focus off a well-paying career to sell chewing gum, and I felt too old to be a carefree entrepreneur. But I developed the product and had to think smart to get it out in the world. I did some Instagram stalking and found a few people with a solid following who I thought might be interested in Mighty Gum. I cold-emailed them and asked if I could send them some product. They said yes, and when they mentioned it on their social channels, the surge we saw in demand was truly surreal. I’d always underestimated the power of partnering with the right influencer, but it was key to our launch.” — Mathew Thalakotur, founder, Mighty Gum

Related: How to Start a Side Hustle With Little or No Money

Draw from Experience

“Just before I graduated college, a part-time consulting gig made me aware of the completely underserved market of tattoo aftercare. I wanted to create a brand to fill that gap, and I brought the idea to my partner, Selom Agbitor. We’d worked together before, drop-shipping women’s swimsuits out of my apartment, and had learned a lot about operating without the hassle of inventory and creating reliable branding and customer service. Now we felt equipped to take on a bigger project. We formulated our product, spent $600 on ad spend, and recruited our neighbors to help us with fulfillment as orders started to roll in. Our goal was to grow fast enough that we could afford to hire manufacturers by the time we graduated — we’d both accepted full-time jobs, after all. That initial $600 proved money well-spent — it got us off the ground, and from there, orders were reliable enough that we could continue funding increasingly large ingredient purchases and boosting ad spend.” — Oliver Zak, cofounder, Mad Rabbit Tattoo

Test Your Product

“During lockdown, I was the conference ambassador for the virtual Women Tech Global Conference 2020. I interviewed the speakers and, after the event, posted the conversations on YouTube. I got so much great feedback, I realized that I could share even more great insight with my community by launching a series in which I interviewed smart leaders on a regular basis. This was a big experiment, so I didn’t want to invest any money at first. Because of that, I eliminated podcasts as an option. Then I realized that a video podcast could be shared on YouTube, which would allow me to analyze feedback—for free. Once it gained momentum, I felt more comfortable investing in webcams, lights, and a proper microphone. Now the series, called Personal Branding for Professionals, is growing — and my future plans now include a traditional podcast.” — Ketaki Vaidya, host, Personal Branding for Professionals

Want to start your own side hustle? Check out our Side Hustle Accelerator and get going today! 

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