In 2010, when my wife was pregnant with our second child, I had a side hustle that almost got me fired from my corporate cubicle job. I started freelancing on the side on a website called Elance (now Upwork).
And I loved it! Making extra money on my nights and weekends, while working from home with a flexible schedule, was the most empowering feeling I’d ever had. I still remember how exuberant I felt when I saw my first side hustle business income arrive in my bank account: “I just got money from the internet!” I shouted. “Maybe I can make enough money this way to support my family.”
I even won the Grand Prize in a contest on Elance/Upwork where I wrote a blog article about why I loved freelancing — I got paid $10,000 for that single blog post. I was triumphant! Nothing could stop me! But then, my day job found out about my side hustle.
Here’s the story of how my side hustle almost got me fired from Corporate America — and why it was worth it.
Beware of HR policies about moonlighting
I did not violate any company policies with my freelance side hustle. (I double-checked the fine print in the HR handbook before I started). I was not working for competitors, using company time or company resources for my side hustle, or otherwise breaking the rules of my full-time employment.
But still: Many corporate employers don’t look fondly at moonlighting side hustles. Freelancing or working a remote side job while holding down a full-time paycheck might not get you fired, but your boss might question your loyalties — “if you have all this extra time and energy to do side hustles, what are we paying you for?”
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That’s what happened to me: I got put on a 30-day termination notice at my day job because of my freelancing at night. Oh well!
Don’t burn the candle at both ends
Another pitfall of side hustles is that you might spend so much time and effort on side projects that your performance suffers at your day job. This started to happen to me, too. I was getting burned out at my day job and my side hustle started to seem more appealing.
Burning the midnight oil on freelance projects was exciting and profitable, but it made it harder for me to wake up early to go to work at my corporate cubicle job. And once again, my boss noticed.
Sometimes you just have to quit your job
It turns out that I had a happy ending with my corporate job: I rallied under pressure, started showing up on time and working harder, and I didn’t get fired. Right after our second child was born, I took unpaid FMLA leave — and then I quit my job to pursue my own business full-time.
I had built up a few months’ worth of cash savings in the bank and I had a few freelance projects all ready to go. I left my corporate job on good terms and with no hard feelings. And I’ve never looked back.
The process of leaving my corporate job was stressful, but it was the right thing to do. Sometimes it’s hard to choose the right time to quit your job to start a business. Lots of people don’t get to choose. Leaving a corporate job to start a business isn’t always a neat, tidy process.
I did the best I could. If anything, my only regret is that I didn’t quit my job a year earlier — because I could’ve had another year to build up my small business and get to a better level of income and career fulfillment.
Why side hustles are worth the risks
As I look back on my corporate career, I’m grateful that I never got fired from a job (despite a few close calls). But even if I had gotten fired because of my side hustle, pursuing a side hustle and starting my own business still would have been the right choice.
By starting my own business, I’ve gone on to make more money, have more fun, and travel all over the world in ways that never would have been possible at a corporate cubicle job. I’ve taken my family to places like London, Berlin, Tokyo, Paris, and Montréal. I’ve been able to be productive and make money 365 days per year, from anywhere with wifi, on my own schedule, on my own terms.
And some people might think that leaving a corporate job is too risky. But as a small business owner, especially if you’re an online freelancer, consultant, or e-commerce business owner, your money can come from the entire internet, instead of from one cubicle, one office building, and one boss. Which deal sounds like better financial security to you?
Bottom line
Sometimes in life, you can’t wait for a corporation to give you permission to make your dreams come true. You have to do what’s right for you and your loved ones. If you value the perceived stability of having a steady paycheck from a full-time job, that’s totally fair — but if you have the hustle, skills, curiosity, and relentless spirit of an entrepreneur, you might want to put more time into your side hustle instead.
Turning your side hustle into a full-time business can deliver bigger income in your bank account, and blissful freedom in your everyday life.
