Tough Stuff: Why A Side Hustle *at* Your Full-Time Job Is the Key to Career Happiness

At C&C, we know being a woman in business isn’t always sunshine and rainbows. That’s why we started a new monthly series called Tough Stuff (see last month’s post here), where we talk about some of the less glamorous parts of having a killer career. Below, Lily Comba shares how she turned her restlessness into a great opportunity—without leaving her job.

Let me start by saying: I love my full-time job. It took several years of trial-and-error to land on a career that I am wholeheartedly happy with, which I feel grateful for every day. But let me also say: when I hit the one year mark, an all-too-familiar suspicion that something better was on the horizon came back.

I began to crave something more. Something that I couldn’t quite pinpoint or identify, but knowing nonetheless that I needed to make a change. The hard part? I didn’t want to leave my company or my team. My initial reaction was that of nervousness — would I be like most millenials, who can’t hold a job for a year due to restlessness? After all, one CareerBuilder survey shared that employers “expect 45% of their newly hired college grads would remain with the company for under two years” and 25% of people under the age of 35 to “have worked five jobs.”

Where To Begin

I went back to square one. Before finding the job I have now, I looked at my career from a bird’s eye view. I asked: What was I good at? What work did I enjoy doing? And which jobs would allow me to be paid to do it all full-time? So when I hit this slow spot in my career, I asked the same questions but with a slight twist. How could I find a new form of fulfillment while remaining at the same company?

I started looking at other teams. In my current role, I’m lucky enough to have the opportunity to work cross-departmentally, so I can really see the types of projects being worked on. And based on these interactions, I knew that a new content strategy team was being created. That immediately piqued my interest. I’ve always wanted to be a writer. And what better way to write a little bit more than to write for a company I already love? So when the director of this new team was officially hired, my gut was telling me to act.

Finding Your Side Hustle

More often than not, your role has the ability to collaborate with other teams. Start by broadening the scope of your work—which meetings are you excited to attend? Which teams are working on projects that you want to learn more about, or could be good at? Take your mind out of your current workload and simply observe. Then, dive into a plan, which we will cover in a moment. But first, let’s help those who are in roles that really don’t allow for much cross-department collaboration. If you’re confined to your role and your team, I encourage you to use your lunch breaks for further development. Set up quick coffee chats or lunch meetings to learn about what others are doing at the company. You’ll be surprised at how willing people are to teach you about their work. Either send an email with your request (keep it short, sweet, and clear about what you’re looking to learn) or add time to their calendar directly (being sure to add context to the event description).

How To Ask For It

I first started writing this article in October, nearly five months ago. Why is this important for you to know? Because fear is a big part of this journey. I was scared it wouldn’t work out. That I would ask the new director of the content team if I could collaborate or contribute to the blog, and she would say “no.” It would be frowned upon by my own team. It all came down to the fear of rejection.  

But I knew I had to get over craving something more,  so I asked for what I wanted. I started by setting up time on the new director’s calendar. After a few back-and-forth interactions in the communal kitchen, we’d developed a friendly relationship, making it easy to ask for time to chat about collaborating. But regardless of our friendly relationship, I came prepared for our meeting. I’d developed a list of five to 10 ways I could bring our partners to the blog, and how I could spearhead the initiative without putting too much on her plate. Her response? “People very rarely raise their hands to take on more, especially when it’s different than what they’re already doing, so thank you for leading the charge on this.” I am forever grateful to this director for taking a chance, having barely known me at the time.

While I still spend the majority of my time in partnerships marketing, I now spend a few hours a week writing partner interviews for the blog. The content relates to my primary role, but I’m simultaneously fulfilling a project that I needed to take on—for my professional and personal happiness.

The Importance

If you find yourself in a similar situation—of loving your job enough to stay but feeling the urge to change—think about how you can take on something different. You may have to move things around on your calendar, maybe even take your side work offline. But by pursuing what you truly want out of you career, and ultimately your life, you will discover a level of gratitude only found when your purpose and practice collide.


By day, Lily Comba works in business development for an online marketplace. By night, Lily lives an entrepreneurial life. After working as a career consultant at her alma mater, Lily developed a passion for helping women in their careers. She embodies the mantra, “If not me, who? If not now, when?” in her work as a writer and business strategist for fellow entrepreneurs. Catch her running around Los Angeles or at