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Balancing Your Creator Side Hustle With A Full-Time Job

Balancing Your Creator Side Hustle With A Full-Time Job

Jessica Williams is the creator behind #jesspicks, a curated newsletter built on the belief that you don’t have to quit your day job to become an entrepreneur.

We sat down with Jessica to talk about going full-time as a creator, how to balance your side-hustle with a job, and newsletter growth strategies.

Finding an audience of side hustlers

Jessica began writing her newsletter when she realised not all entrepreneurs could leave their jobs. "I kept hearing that you had to quit your day job and go all in, but this isn’t always an option. Not for me, as a caregiver, for example". She decided to add to the conversation: "My newsletter became a vehicle for connecting side hustlers with resources and tips to get started".

Going all in vs. having a side hustle

Going full-time might sound like the ultimate goal, but Jessica thinks creators should be aware of the challenges that come with it. "You might not get as much time to experiment when you have to think about the money more and your livelihood is at stake." Drawing from her own experience, she advised, "I recommend sticking to a side hustle first. Get clarity on what you’re doing and what you want before going full-time."

Jessica stresses that every creator’s journey is different. "Some folks can save up their income and pursue their dreams full-time. It’s almost like "jump, and the net will appear". That’s motivating for some and scary for others."

Only you know what’s right for you. "If you want to keep it small and keep your job, that's an option. If you want to take it full-time, that's also an option." Ultimately, you have to carve out your own path rather than the one you think you should be on.

How to balance your side hustle with a job

Jessica shares her advice for anyone who’s trying to balance being a creator with a job:

  • Get honest about the amount of time you have. "If I only have 30 minutes to work on my business on any given day, that’s okay. I’ve learned that you can get a lot done in 15 minutes," Jessica explains.
  • Break down tasks into small, manageable steps. Not sure what you’re doing? Just focus on the one thing you can do to move things forward.
  • Redefine what success looks like. "I’ve stripped down my side hustle to running a newsletter and adding other things when I have the capacity. If I’m getting my newsletter out every week, I consider that a win."
  • Understand your priorities will shift at any given moment. As someone juggling multiple things, you need to consider what needs your attention the most.

Newsletter growth

Despite keeping her newsletter as a side hustle, Jessica has grown her audience to over 2500 subscribers and monetised it. Jessica credits this to consistent calls to action. "If I were on a podcast, at an event, or doing a workshop, my parting words would be: please join my #jesspicks newsletter."

By consistently writing a valuable newsletter, Jessica has also been able to grow her email list through word of mouth and shout-outs from creators like Josh Spector. Getting listed on newsletters, participating in bundles, and being active on Twitter, Facebook, and Reddit have also helped.


For a long time, Jessica thought she needed at least 1000 subscribers to monetise with sponsorships. "After I shared this with other newsletter creators, they advised me to start where I was, which was 500 subscribers, with classified ads”. Now Jessica monetises her newsletter in 4 ways:

  1. Advertising with sponsored and classified ads
  2. Tips/Donations
  3. Affiliate Marketing
  4. 1:1 Coaching

Finding Sponsors

Jessica finds sponsors for her newsletter through marketplaces like Hecto, Swapstack, and Paved, and referrals from her readers.

Jessica’s Passionfroot page also attracts sponsors and secures more bookings. "Jamie’s Minimalist Hustler sponsorship page caught my attention. I was intrigued by having a platform to navigate the sponsorship process instead of dealing with the back-and-forth of email".

If you’d like to have your own page to streamline sponsorships, sign up for early access to Passionfroot.