The Importance of Side Hustles
By: Felicia C. Sullivan
Tags: Entrepreneurship, Work, Freelancing, Side Project, Creativity

I started out my career in the age of file cabinets and resumes on bond paper. Back in the day, you mailed your resume to the company you wanted to court, and prayed that yours would be the one to rise above the stack. This was an age when cold calls were verboten, and recommendations consisted of someone making phone calls on your behalf. There was no LinkedIn. Few used email. Who even owned a computer?

Throughout college, I interned at financial firms and investment banks. I was on scholarship and needed to eat, and banks paid well. I worked for Smith Barney, Merrill Lynch, and Reuters. The work was… tolerable. When I graduated, I took a job at Chase because this was what we did — we went along with the predefined plan. We didn’t question the trajectory. Even if I hated the wool suits that made my arms itch. Even though I knew I wasn’t doing anything more than shuttling money around. I spent a year at Chase and two at Morgan Stanley staring at spreadsheets. We expensed client dinners and went on Starbucks runs. We clawed and competed.

One day I rode the subway to work and thought this was a bucket of crazy. I didn’t want to work in a bank for the rest of my life — regardless of the lucrative stock purchase plans and the illusion of financial stability. I wanted to flee the joint.

I called recruiters, who told me I could only get jobs in banking. Why would I want to waste the past three years? The last seven if you included the laundry list of internships. I’d have to start over because I didn’t have experience in any other industry. To which I responded, that’s stupid.

At the time, I’d been routinely hitting up sample sales, traveling to clothing outlets, and selling items on eBay. It occurred to me that there was no outlet for designer resale, though a market existed. A hungry one. Online stores were new. This was the era of Geocities and AOL. There were parts of the country, the world, where people didn’t have access to designer clothes at a discount. After recruiters laughed at my desire for a career change, I returned to work and decided to create an experience where none existed. I filed papers for an LLC, managed my own accounting, built a website (this was not easy in 1999), purchased a camera, and scouted sample sales for inventory. I was the small-fry Nordstrom Rack.

If I hadn’t built a business from scratch, I wouldn’t have realized that I was more than the sum of my parts.

What I hadn’t predicted was my love of digital and marketing, and how much I would learn while building a business. My online shop caught the attention of my next employer, who hired me as a project manager for a burgeoning luxury goods dot-com.

That’s when I first learned about the importance of a side hustle. That’s when I learned how to say, fuck you and your ‘no,’ out loud.

If I hadn’t built a business from scratch, I wouldn’t have realized that I was more than the sum of my parts. I wouldn’t have realized that shifting gears was possible. Cultivating experience by doing was possible. I didn’t have to spend a lifetime in investment banking. There are thousands of people out there pushing paper and going through the motions because they think that’s what they have to do. They don’t want to go off book, and that’s perfectly fine. However, it’s possible to design a career of your own making like I did. Side hustles have moxie. They make for a good first conversation. They make people do a double-take. I’ve been on the other side of the hiring spectrum, and I’ve looked for ingenuity and side projects. Because when it comes down to it, people hire people, not paper.

Every job I’ve gotten in my two-decade career has been a result of my side projects. They’ve gotten me through doors that would have otherwise remained closed. They’ve given me supplemental income. Side projects have saved me from the cubicle and empowered me to learn skills that I wouldn’t have gained in a traditional office environment. My hustles have expanded my network and put me in front of people who have become lifelong friends. I’ve launched literary magazines and websites, hosted events, and started organizations — all because I wanted to build and see where that work would bring me next. My work has allowed me to build an impressive toolkit of skills beyond the financial track that felt so confining at the start of my career.

More importantly, side hustles have given me hope when none existed. They’ve made me believe that constant reinvention is possible, even as I get older.

How to Start Your Hustle

Start from a place of curiosity

Pursue something that excites you. I like to think of how children play and create. They do it for the joy of it, and also because they’re driven by a primal need to question things.

Studies show that curiosity is a marker for academic success. Besides, you’ll have more fun with your project and flex varying brain muscles if you know your income doesn’t depend on it. You’ll start to notice how this passion and new skill informs or augments what you’re doing in your professional life. Or, it might take you in a completely different direction. You always know where you start, but the joy comes from accepting the uncertainty of where you’ll end up.

Start small

My early side hustles were inspired by my friend Jeff’s book, 52 Projects. Sometimes we get subsumed by the notion of BIG when we need to start small. Explore your creative and practical self through small, fun assignments or hobbies — baking a batch of cookies, for example, or learning how to write simple software programs. You don’t need to conquer the world from the get-go.

Recently, I was listening to a podcast when I heard a powerful quote from Silicon Valley investor Paul Graham. He said, “Don’t build things that scale.” Although I’m loath to share jargon, I like the idea of starting with something we can bury ourselves in. Something that can’t yet be automated or turned into a process. The beginnings are always about exploration, depth, inefficiency, getting lost — allow that to happen because that’s where you find the greater truth and love in what you’re pursuing.

Take classes

From local continuing ed classes to online education, I’m always learning new skills or strengthening my existing ones. Most online classes are affordable or free. I love Skillshare, anything Lynda, and Udemy. This list of free classes is also pretty incredible. Right now, I’m immersed in podcasting tutorials, entrepreneur classes, and email marketing and SEM.

Raise your hand

Throughout my career, I’ve gone out of my way to connect with people in different departments and volunteer to help on projects where I have less experience. Consider it an informal apprenticeship, but I’ve found it so helpful to learn about analytics by sitting with an analyst, watching her run reports and synthesize data. I learned so much about photography by helping a friend out on a project. I have also traded skills with friends. I teach social or cooking, and they help me navigate CRM and data.

Take the time

People always say they’re “so busy,” but they sure have time to binge six hours of Black Mirror. Schedule your side project. Block off time on your calendar and treat it like any other appointment. Making time for your passion project will energize you when you have to return to the daily grind.

The Best Advice I Can Offer Anyone: Be a Student

You’re never an expert because there’s always something new to master. A yoga teacher once told me that the mark of an advanced practitioner is one who goes back to a basics class to relearn the poses. That stayed with me for years. Even though I consider myself pretty darn smart and talented, I want to keep learning. My side projects allow for that growth.

Right now, I’m downloading e-marketing tutorials, entrepreneurship classes, podcasting tips, etc. I tell you, it feels good to be hungry. It feels good to never stop learning.