Having a Side Hustle Can Transform Your Career

I am a staunch advocate for side hustles. There are lots of stories about how Gen Z and Millennials are increasingly taking on second jobs and side gigs. The main reason is usually to earn extra cash, but there are also other benefits, like learning new skills and making connections.

Starting a side hustle was hugely beneficial for my own career and wellbeing. I spent my 20s working in different tech teams and feeling overworked, underpaid and out of place. I struggled with a toxic work culture where offensive jokes were constantly made and brushed off as “banter,” where I received more comments about my outfit choices than the goals I reached, and where all-male groups would often exclude me from social events.

Having my own business helped me pursue work I found meaningful, express my values and ambition and maximize my earnings potential. It took me from being “just another woman of color” in tech to being a recognized entrepreneur, opening up opportunities I couldn’t have imagined.

In the process I learned that having a side business comes with its own risks and challenges. It can certainly take a toll on your full-time job and your health. But if you approach with care, you can build something sustainable. Here’s what I wish I knew.

Have a clear picture of your goals. In 2016 I quit my job at a tech startup after realizing just how much its culture was affecting me. I wanted to stay in tech, because I thought the industry offered the best path for maximizing my earnings (compensation packages tend to include equity stakes on top of salaries). But I didn’t want to join another company and team that looked great on the surface only to be toxic underneath. I also wanted a greater degree of flexibility.

So I decided to forgo full-time employment, and initially even the side-hustle route, and instead commit to starting my own business. Being based in the U.K. made this decision easier (I could access free healthcare), as did being in my 20s, since I wasn’t yet all that worried about saving for retirement.

Be flexible. Over the course of a year working as a full-time entrepreneur, I tried and failed to raise funding dozens of times. The setbacks made me miss a lot of things about working for an employer: being part of a team, having people around to solve problems with, getting a regular paycheck and benefits.

I decided to go back to working for a company while continuing my business on the side. Being an entrepreneur doesn’t have to be all or nothing. For me, having a side hustle was the best of both worlds: I got the chance to be my own boss sometimes, but with greater financial security overall. I didn’t have to pour as much time and money into my venture, and I found the payoff to be just as satisfying. The key is, if you’re not achieving the results you want, think about what can change.

Work on a problem close to your heart. One of the most common questions I get about side hustles is, what should mine be? Well, consider what you care about. Creating a product or service based around a personal experience makes it a lot easier to tell a compelling brand story and connect with prospective customers and clients.

For me, I wanted to help teams tackle bias so I created workshops to promote inclusion. I would write LinkedIn and Medium posts focused on the lack of diversity in tech, talking about the frustrations I’d faced in my career. These resonated with other underrepresented professionals on the internet — and they became my first community members, helping me promote my brand within their companies and land my first training clients.

Be proactive with your employer. More and more employers recognize that folks have multi-hyphen careers, but it’s best to get ahead of any potential issues. Read your employment contract carefully to ensure you can embark on your venture, or ask your manager. If you need to obtain permission, write a simple one-pager explaining what your business will sell and why it won’t affect your work.

Some managers may encourage your outside gig. When my former employer Product Hunt was struggling to recruit more women for its engineering team and wanted diversity and inclusion training, my boss suggested they fly me out for that task. I was invited to deliver training to the San Francisco and New York offices. This led to more tech firms in the U.S. booking my business.

Of course, not all employers or managers will be supportive, so prepare to address concerns. Clarify that you will only work on your business on your own time and on your own personal devices. Create a firm separation between your job and your business. You shouldn’t be promoting your hustle on work channels unless you have permission to do so.

Create boundaries and stick to them. While you don’t want your side hustle cutting into your regular job, you will need to find enough time and energy to dedicate to your project to see results. In my case, I separate my side hustle from my main job and my personal life. I aim to work a finite amount of time on my business each week (and keep some of my weekends free), and I’ve created realistic time-bound milestones to measure my progress.

The side hustle route let me build a business at a sustainable pace with the safety net of a salary. I’m not letting it go anytime soon.

This column does not necessarily reflect the opinion of the editorial board or Bloomberg LP and its owners.

Abadesi Osunsade is the founder and chief executive officer of Hustle Crew. She is the co-host of the Techish podcast and author of "Dream Big. Hustle Hard: The Millennial Woman’s Guide to Success in Tech."

©2021 Bloomberg L.P.

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