What Could You Charge Somebody $50 for Tomorrow? Starting a Side Hustle with Expert Jessica Williams

woman photographing her creative work

Side hustles have come in clutch for me over the last decade. They’ve provided income, flexibility, stability, and even career opportunities. But they can also be frustrating, and sometimes feel like they’re not worth it.

Here to break down myths, help us find our next side hustle, and reframe how we think about our time and energy, is side hustle expert and curator of the popular #jesspicks newsletter, Jessica Williams.

The Big Side Hustle Mistake Jessica Sees People Making

Side hustles are great for diversifying your income and growing wealth. They can also serve as creative paths to entrepreneurship, especially since it’s still so difficult for women startup founders to get funded.

Jessica says, “not everybody needs to be an entrepreneur. I feel like there's a lot of glamorizing of entrepreneurship. It’s not easy. But if you have the entrepreneurial bug, if there's always something that you wanted to try, absolutely give a side hustle a try.”

But the mistake she doesn’t want you to make with your side hustle? Turning a passion into a job.

“The thing that I don't want people to do is feel like they have to monetize everything they do. You're allowed to have hobbies. You're allowed to do things you love to do without trying to make a buck off of them.”

How to Go at Your Own Pace

Two women on the ground helping each other up to workout

Something about being an entrepreneur or a side hustler immediately brings up insecurities and fears, but Jessica encourages her followers to think about what success looks like for them. “There's a lot of pressure in this world: oh my God, you have to spend five hours a day on your side hustle! You have to give up sleep! That's just not my style at all.”

Jessica explains, “I approach side hustles from the angle of not necessarily wanting to make more money because money is good, but what is that thing you kind of always wanted to do or explore? Make time for that.”

Ask Yourself These Two Questions to Help You Find Your Side Hustle

Want to start a side hustle but not sure what? Jessica says to ask these two questions:

  • What could you charge somebody $50 an hour for tomorrow?
  • What could you talk about for thirty minutes with no prep?

If you’re still stuck, think about what you’re passionate about. What kind of books do you read? What did you like to do when you were a kid? Then, go crazy and brainstorm!

“Come up with a list of ten ideas. Pick one to create an offer for. A one-hour coaching call, a one-hour class. Whatever it is, is there a small way we can test this out?”

The goal, BTW, is testing and tweaking, not perfection:

“Ultimately we think we want to do something, but then we get in it and we're like, no. You have to test it out and see how it goes and tweak it from there. You have to get that feedback and say, okay, does this make sense? Do I want to move forward with this? So much of this is experimentation. You have to say: whatever happens, I'm going to learn from it.”

Jessica’s #1 Piece of Advice for the Struggling Side Hustler

Side hustlers often struggle with what Jessica calls “the juggle.” She says, “I think it's a matter of getting really honest about the amount of time you have. If you only have 30 minutes a day, that's okay. You can actually get a lot done in 30 minutes. Reframing this idea of time and energy and how you can use it is so important.”

“I feel like a lot of it too is just giving yourself permission to create your business in a way that works for you. And to just try to grow it as you have more time, as you have more energy, as you have more information.”

Thanks so much for sharing your wisdom with us, Jessica!

Sarah Guerrero
Sarah Guerrero
Sarah Guerrero is a freelance writer and contributor to Slow North. She has a degree in international business from St. Mary’s University in San Antonio, Texas, and writes about sustainable business practices and ethical living.