150: The Best Way to Help a Teen Start a Side Hustle
Here’s how to help a teen start a side hustle with real-world examples, mindset shifts, and practical tips that build confidence, independence, life skills — and income — before they turn 18.
You can catch it on video too:
What if the teen in your life could build confidence, real-world skills, and earn income—all before turning 18?
In this episode, I sit down with Renee and Jonathan Harris, parents of nine kids , many of whom have already launched their own side hustles. We talk about how they’ve guided their kids to discover what they’re naturally good at, take ownership of their learning, and turn those interests into cash flow.
Whether you’re a parent, mentor, aunt, uncle, grandparent, or simply someone who cares about helping teens thrive, this conversation is full of honest, practical insight.
You’ll learn:
- How to recognize the difference between a teen’s interest and their underlying skill set
- Why starting within the household is often the best first step
- What to do when your teen receives no feedback—or negative feedback—on their efforts
- How to normalize both the hard seasons and the wins of entrepreneurship
- Why serving others is the key to turning a hobby into a side hustle
----
Do you like what you're hearing? Consider giving it a caffeinated thumbs up . We'd really appreciate it!
Need a little (and sometimes big) push to start and stay focused to grow your side hustle? Dive into my online Masterclass: How To Turn Your Thoughts Into Wanted Things .
----
Why Should Teens Start a Side Hustle?
Let’s face it: the world has changed. College isn’t the only path to a successful life — and it’s definitely not the cheapest. The Harris family recognized early on that helping their kids earn money before adulthood could build confidence, develop real skills, and even help fund education or business dreams.
But more importantly, side hustling gives teens hands-on experience in:
- Problem-solving
- Resilience
- Creativity
- Time management
- Serving others
These are life skills, not just business skills.
“Parent Their Passion”: The Method That Guided Their Teens Side Hustles
What’s refreshing about Renee and Jonathan’s approach is that it wasn’t born in a business school — it grew out of real life, necessity, and trial-and-error. After a layoff shook their household, they brought their kids into the journey of starting a skincare product business at a farmers’ market.
From that, they created a system they now call Parent Their Passion. Here’s how it works:
Step 1: Pay attention to what lights them up
It starts by observing — not assuming. A teen might say they want to be a race car driver, but what they’re really drawn to could be something else entirely. In the episode, Jonathan shares an example of how surface-level interests can often point to something deeper. A teen fascinated with race cars might not be dreaming of NASCAR, but instead showing signs of being mechanically inclined. Maybe they’re always fixing things around the house or taking apart the lawnmower just to see how it works.
As a parent, mentor, or supportive adult, it’s your job to look beyond the label. You’re not trying to shut down the dream—you’re just helping them uncover the skill set underneath it. That subtle shift from “racing” to “repairing” can reveal a side hustle path that’s more realistic and still deeply fulfilling.
Step 2: Marry their interest with available tools
What resources already exist in your home or network? Whether it’s an old camera, a relative with a useful skill, or even shared family equipment, the Harris method focuses on starting with what you have.
One of the most overlooked sources of opportunity is your own household. If your teen loves baking, could they make birthday treats for a younger sibling or a grandparent’s gathering? That’s how Renee and Jonathan got their daughter started—by letting her contribute in a way that was helpful to the family and built confidence at the same time.
It’s not just about monetizing right away—it’s about using real environments to develop the skills that will eventually serve others.
Step 3: Focus on serving, not just doing
A hobby becomes a hustle when it helps someone else. Teens often have interests that stay “just hobbies” because they aren’t connected to any real need. When teens start looking for how their skills can serve others, the whole game changes.
Serving could mean baking cupcakes for a neighbour’s party, helping a family friend organize their garage, or editing a cousin’s school project video. The activity might be fun — but when it’s helpful too, you’ve tapped into a side hustle mentality.
Real Examples: From Drone Videos to Bladesmithing
The Harris kids followed different paths:
- One son turned a love of drones into a production company
- Another became a bladesmith, starting in the garage and now owning a machine shop
- A daughter who loved graphic design found her niche in book cover design
None of this came from a perfect business plan—it came from experimenting, pivoting, and sometimes failing. They weren’t chasing trends—they were building skills in real-time, based on interests, tools at hand, and opportunities in front of them.
When There’s No Feedback—or Worse, Negative Feedback
What happens when your teen puts something out there and… nothing happens? Or worse, someone criticizes their work? It’s such a valuable piece of the puzzle.
Renee and Jonathan stressed that it’s critical to normalize this experience early. Feedback — or lack of it—is part of the learning process. Instead of seeing silence or criticism as failure, they encouraged their kids to see it as data. Does the product need tweaking? Is it being shared with the right people? Did we ask for input directly?
Sometimes, people won’t say anything simply because they don’t know how to respond. That doesn’t mean your teen’s idea is bad. It means the next step is to ask questions, observe what’s working, and keep going.
As a supportive adult, you can help reframe these moments. Remind them: This is part of building something real. It doesn’t mean stop—it means adjust.
Celebrate the Wins—Not Just the Struggles
Renee made a powerful point in the episode: if all our kids hear is how hard it is to run a business, why would they ever want to do it? Yes, there are tough seasons—long days, low feedback, financial pressure—but there are also wins worth celebrating. She encouraged parents to talk about both.
If you land a new client, finally hit a goal, or even just feel proud of how you handled a challenge—say it out loud. Let your teen see that entrepreneurship isn’t just sacrifice. It can be rewarding, energizing, and meaningful. When they see the joy that comes from the wins, they’re more likely to stick with it through the tough parts.
What If the Teen Isn’t Interested in Business?
Not every teen loves the “business side” of things. Renee and Jonathan suggest a powerful strategy—don’t buy the tools for them.
If they want a $500 microphone, great. How are they going to earn the money for it? This not only builds responsibility but often motivates them to get creative and look for ways to earn — without pressure or lectures.
The goal isn’t to push kids into becoming entrepreneurs. It’s to help them recognize that their time, energy, and skills have value, and they can start realizing that sooner than they think.
Pro Tip from the Episode: Start with Your Own Environment
Even if you don’t have a business or side hustle yourself, you can still offer support by simply looking around your home. What needs doing? What could your teen help with that would make life easier for someone else in the family?
Maybe they could digitize old family photos. Or design a birthday invite in Canva. Or take over video-editing chores for a younger sibling’s school project. These aren’t side hustles yet—butthey build confidence and develop marketable skills.
As Renee and Jonathan shared, several of their kids’ first side hustles started by helping within the home. From graphic design to product photography, the value started right under their roof.
What This Made Me Reflect On…
While editing this episode, it made me think back to a moment in my own teenage years that shaped how I think about possibility today.
When I was 16, I had the chance to buy a beautiful thoroughbred horse for $500. I know, $500 sounds low for a horse—but at the time, for me, it was huge. I had worked for free at a farm for months to earn the opportunity, and when the chance came, my parents offered to cover half if I could come up with the other $250. So I got a part-time job, saved my birthday money, hustled any side ventures I could come up with and made it happen.
Her stable name was Peanut. She had a longer, fancier registered name, but to me, she was just Peanut. I didn’t know it then, but that was probably the first time I experienced the mindset of making things happen instead of waiting for them.
Years later, when kayaks were becoming a trend, I wanted one—but didn’t want to pay full price. So I asked: how many would I need to sell in order to get two for free? I realized that if we sold six or seven, our two would be covered. We did, and they were.
And now that I’m putting the finishing touches on a new guide for side hustlers, I’m wondering - did that belief start with Peanut?
Free Resource: Coming Soon
In the next week or so, I’ll be releasing the free 28-page guide called Smart Start: From ‘Idea’ to ‘It’s Live’ in 7 Steps – A Beginner’s Guide to Launching Your Side Hustle with Confidence.
In it, I actually include that kayak story—and walk you through a clear, practical path to bringing your own idea to life. Whether it’s for you or a teen you care about, it’ll help you think differently about how to get started.
Whether you’re just starting or already helping a teen start a side hustle, this guide will give you a clear, doable path forward.
Final Thought
Helping a teen start a side hustle isn’t just about the money. It’s about giving them a head start in confidence, clarity, and creativity. And as Renee and Jonathan reminded us, when you help a teen learn how to serve others with their skills, you’re setting them up for a lifetime of possibility.
Connect with Renee & Jonathan:
Parent Their Passion Website
Connect with Joan:
Be on the show!
Tell us about your side hustle success story!
