5 exercises to find your ideal 'grand-slam success' side hustle

"You'll find that idea you just can't stop thinking about."

Jen Glantz is the founder of Bridesmaid for Hire.
Photo by Susan Shek Photography

Before I started my first side hustle in 2014, I had notebooks filled with ideas I never acted on and longtime dreams of being an entrepreneur. 

I spent many afternoons researching business ideas and writing down the ones I couldn't stop thinking about. I came close to launching a couple that seemed straightforward enough to run, like a dropshipping store or a resume writing service. But I couldn't maintain the enthusiasm to follow through. Figuring out which ventures to really invest my time and effort into was a challenge. 

Around this time, I had a problem that I couldn't quite shake. After being in more than a dozen bridal parties, I had gained a reputation for being a reliable bridesmaid. I loved doing it, but at this point, more than a half a dozen distant friends had asked me to be in their weddings when they didn't have anyone else to ask. That was when I came up with a new idea: a business where strangers could hire me to be there for them as their bridesmaid. 

I didn't know if the idea would be a grand-slam success, but clearly, I had a skill set that was in demand. I knew it was something I couldn't stop thinking about. And I knew that my experience plus my love of helping strangers would motivate me to bring the idea to life. But seven years later, I've turned that inkling of a side hustle into a six-figure business, hired a team of independent contractors, and helped hundreds of brides. 

If you're like me and have struggled with figuring out which side hustle is the right one for you, here are five challenges that can help you get started in 2021.

Conduct a personal strengths and skills inventory

To be an entrepreneur and run a business, it's important to have a good grasp on what your strengths are and what your unique value is. That way, you can find ways to make your business stand out and you lead it authentically. 

Knowing this information might make you narrow down a list of side hustle ideas or help spark one that you never thought of.

Go over the last decade of your life and make lists of 10 strengths, 10 skills, 10 life accomplishments, 10 areas of improvements, 10 interests, 10 hobbies, and 10 passions you have. Having these lists to refer to can help you feel more organized and might even reveal a clearer focus on an area, industry, or idea for your side hustle. 

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Phone a friend

It can be hard to self-reflect on the questions around our strengths, skills, and unique values. That's where your network comes in. 

Make a list of 10 people in your life you can contact for an honest assessment. Make sure this list has variety in it: Include friends, family members, past co-workers, people you met from volunteering, etc. 

When you contact them, ask them questions about your strength, skills, and unique values, and write down their answers. You might even ask what kind of business they can see you starting. 

Use this information to find similarities within the answers and write down three to five side hustle ideas that you can think of based on what they shared with you. 

Study other side hustles and business models

Find other businesses that fascinate or interest you. Even if these are side hustles in industries you have no interest in jumping into, they might have a business model that inspires you to take a certain direction or that influences how you can make your product or service stand out in your own industry.

Let's say there's a beverage company with branding you admire or a shoe company with a limited launch schedule you find intriguing. Take note of this and see how you can take these strategies and use them to elevate an idea you have.

To help you find interesting businesses out there, listen to podcasts (such as NPR'S "How I Built This" or "My First Million"), watch business TV shows (such as "The Profit" or "Shark Tank"), or read memoirs or blogs from entrepreneurs you admire. 

This may help you get the full picture on how they started well-known companies, what gave them the idea, and how they brought it to life. 

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Write down 10 problems a day for 10 Days

Successful businesses and side hustles address problems people have, and solve them in unique and beneficial ways. If you're struggling to come up with ideas, start writing down everyday problems that you or people around you are experiencing. Challenge yourself to write a list of 10 problems a day for 10 days. 

For example, maybe you hear your friends share how much time they spend on Sunday meal prepping and use that problem to spin off a list of solutions that could turn into side hustles. Maybe you're fed up with having to stand in a long line to drop packages off at the post office. Use that as a scenario that helps you brainstorm what solutions are out there and what might be missing. My business was created after I witnessed a problem inside the wedding industry that nobody else had solved.

At the end of 10 days, circle the problems that you want to dive into more. Investigate who is already attempting to solve this and what else can be created to solve it even better or differently. 

From there, you'll have ideas you can narrow down based on what you find and what you're the most interested in pursuing. 

Successful businesses and side hustles address problems people have and solve them in unique and beneficial ways.

Ask yourself, who do you want to be the hero to?

Another way to approach this side hustle brainstorm is to look beyond the problem and figure out who you want your audience to be. I love the idea of thinking about who you want to be the hero to with the product or service that you create, because it allows you to think about a strong purpose and a clear audience.

Once you have that, you can dive into the needs, problems, or challenges that the audience might have (with social media research or industry trend research) and determine a side hustle idea that will benefit them or bring value to their lives. 

While you might be eager to come up with a side hustle idea, it's better not to rush to the finish line of picking something and moving forward with it until you're sure that there is a strong need for this idea and you're equally passionate about pursuing it.

But if starting a side hustle is high up on your 2021 to-do list, pick some of these challenges and set deadlines of a week per challenge to see what comes from going through the motions of thinking, exploring, and researching. Before you know it, you'll find that idea you just can't stop thinking about. 

Jen Glantz is the founder and CEO of the business Bridesmaid for Hire, the voice of the podcast "You're Not Getting Any Younger,″ and the author of the Amazon-bestselling books "All My Friends Are Engaged and "Always a Bridesmaid for Hire."

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