Hi, I’m Jessica — side hustle cheerleader, speaker and wearer of many hats (sometimes all at once).
I speak to people who are juggling a lot: caregiving (or parenting), full-time jobs, messy schedules, and still want to build something of their own.
My talks are part pep talk, part strategy session, and 100% rooted in real life. help audiences feel less behind, more equipped, and genuinely excited to take the next step.
I'm a great fit for:
- Coworking spaces and creative communities
- University events and student entrepreneurship groups
- Corporate employee resource groups (ERGs)
- Virtual summits, podcasts, and panels
- Anyone who wants inspiration with instructions — and a little cheerleading on the side 💁🏾♀️
Michelle Ward
“When my community asked for a session on side hustling, only one person came to mind to bring in: Jessica Williams! She hosted an AMA for my clients and covered mindset, quitting plans, time management, work/life balance, and more. Everyone walked away inspired, seen, supported and comforted, with lots of gems of wisdom to tuck away. Jessica is a wonderful speaker I'd recommend highly – I'd have her back anytime!”
“Your side hustle session was FABULOUS! Thank you so much! I think the ladies really enjoyed it and got some good tips — I resonated with a lot of what you said in my own journey too. Also, your slides were amazing!”
Chloe Daniels
Are You Side-Curious?
How to Launch a Side Hustle Without Burning Out
If you’ve ever thought, “I kinda want a business… but I also like having a steady paycheck,” this one’s for you.
In this talk, I’ll help you explore what a side hustle could look like for you, without the pressure to go all-in. I walk through how to get started, manage your time, and keep going in a way that feels doable, not draining.
“I really like how practical your side hustle session was with your tips and advice, and advocating for the experimental framework and mindset so that it doesn’t become one big scary thing.”
Inbox Goals
How I Built a 2500+ Subscriber Newsletter (Without Writing a Ton)
What if you didn’t have to write essays to grow a newsletter people love? In this session, I share the behind-the-scenes of #jesspicks — my curated newsletter that’s now 400+ issues strong — and how you can grow your audience through consistency, curation, and community.
Start Where You Are
Tiny Truths for a Life That’s Yours
This one’s for the late bloomers, the stop-and-starters, the people building their dreams in the margins of caregiving, day jobs, and full calendars.
Through personal stories, gentle humor, and some real talk, I invite you to rethink what progress really looks like, embrace imperfect starts, and remember that small moves still count. Whether you're feeling stuck, starting over, or simply searching for a path that fits, this talk is your permission slip to begin exactly where you are.
Need bios, headshots, logos, or photos? Head to the media kit.
Booking Inquiry
I’m based in Chicago and speak virtually everywhere.
Ready to bring me to your event, team, or community? Fill out the form below and I’ll be in touch.
(And if I’m not the right fit, I’ll happily connect you with someone amazing.)
