I’m a serial entrepreneur — and apparently I always have been.
My first side business started when I was about four years old, picking dandelions and selling them to neighbors who were more than happy to pay a few coins for a tidy yard. I didn’t know words like pricing, margins, or customer service — but I understood effort, value, and pride in earning something on my own.
That nickel-a-bucket dandelion business was just the beginning.
I liked being self‑employed. I liked being in charge of my own destiny. Pet sitting came next , then babysitting. Then selling art. Later, hosting and producing large‑scale events for the tech industry. Entrepreneurship wasn’t a phase — it was a through‑line.
Part of that isn’t surprising. My father was an entrepreneur. My grandfather was an entrepreneur. And his father before him. So when my own children started showing that same spark — wanting something badly enough to work for it — I recognized it immediately.
Years later, as a market organizer watching hundreds of vendors — including kids — step into entrepreneurship for the first time, I’ve learned this: selling is the easy part. The real value is everything kids learn around the sale.
If your child wants to sell their art, baked goods, crafts, or creations at a market, this post is for you. Not as a cheerleader shouting “hustle harder,” but as a practical guide to helping your child grow confidence, responsibility, and resilience — while still keeping it fun.
This is based on real market experience, real families, and real kids.
1. Pricing: Let It Be a Learning Tool (Not a Parent Decision)
One of my favorite family stories comes from when my youngest was about five years old. He announced that he had a dream: he wanted to play the violin.
So we helped him figure out how to make that happen. He collected cans, molded and recycled what he could, and walked the neighborhood selling flowers planted in soup cans. In about a month, he had raised enough money for violin lessons — and eventually, a full year of them.
Thirty years later, a few violins later, that lesson still matters.
Pricing wasn’t about perfection. It was about helping a child connect effort to outcome.
Pricing is often the first place parents want to step in — usually to help. Resist the urge to fix it.
Instead, walk your child through:
- Cost of Goods (COGS): What did it actually cost to make the item?
- Time: How long did it take?
- Market reality: What are similar items selling for?
Let them choose the final price — even if it’s imperfect.
Why this matters:
- Kids learn quickly when something doesn’t sell
- They learn even faster when something sells out too fast
- Both outcomes are valuable
Markets are a low-risk classroom. The lesson is more important than the dollar amount.
2. Responsibility: It’s Their Business
Earlier in my life, I spent time working as a part‑time nanny. The kids I cared for loved creating art. Every week after Kung Fu class, they’d bring home the wooden boards they had broken during practice, and instead of tossing them aside, they turned them into canvases.
We transformed the hallway into a gallery. The kids labeled their work, added price tags, and proudly displayed their masterpieces. Some were priced at a million dollars.
Ten years later, that hallway still looks exactly the same — price tags and all. The parents told the kids they couldn’t sell the pieces for that much, not because they weren’t valuable, but because they were too special.
That experience taught me something I still see play out at markets today: when kids are trusted to own their work — even playfully — they take pride in it. Responsibility doesn’t always start with money changing hands. Sometimes it starts with being taken seriously.
One of the biggest growth moments I see is when a child realizes:
“This isn’t my parent’s booth. This is mine.”
Encourage responsibility by having your child:
- Set up their own display (with guidance)
- Greet customers themselves
- Handle transactions appropriate to their age
- Track inventory before and after the market
Parents should be supportive, not the salesperson.
If a child walks away from the booth constantly, forgets pricing, or doesn’t engage — that’s not failure. That’s feedback.
3. Confidence: Built One Conversation at a Time
Confidence doesn’t come from selling out. It comes from repetition.
Markets teach kids how to:
- Make eye contact
- Answer questions
- Explain their work
- Hear “no thank you” without taking it personally
Pro tip from the market floor:
Start with a simple script your child feels comfortable saying, such as:
“Hi, I made these myself.”
Everything grows from there.
Confidence earned this way sticks.
4. Failure: Normalize It Early
Not every market is a good market. Not every product is a hit. And not every day is fun.
That’s okay.
After a slow market, ask:
- What surprised you?
- What would you change next time?
- What did you still enjoy?
Avoid:
- Blaming the event
- Blaming customers
- Immediately quitting
Failure at this age isn’t discouraging — it’s formative.
Kids who learn to adjust instead of giving up are learning entrepreneurship the right way.
5. Taxes (Lightly): Awareness, Not Anxiety
No one expects kids to become tax experts — but awareness matters.
At an age-appropriate level, explain:
- Income should be tracked
- Expenses matter
- Some money may need to be set aside
This can be as simple as:
- A notebook
- A spreadsheet
- A conversation at the end of the season
The goal isn’t compliance perfection — it’s understanding that business has responsibilities, not just rewards.
6. Don’t Forget the Fun
My oldest is probably the most entrepreneurial of all three of my children. He’s always trying something new, usually centered around things he genuinely loves. Watching that has reinforced something I believe deeply: entrepreneurship works best when it’s rooted in curiosity and joy, not pressure.
If it stops being fun, something needs adjusting.
Watch for signs of burnout:
- Pressure to perform
- Too many markets
- Adult expectations creeping in
Remember:
- This is not a college application
- This is not a brand strategy
- This is not about maximizing profit
It is about creativity, pride, learning, and joy.
Some kids will grow into lifelong entrepreneurs.
Others will take these skills into completely different paths.
Both outcomes are wins.
Final Thought From the Market Floor
I’ve lived this story from every side — as a child who loved being self‑employed, as a parent guiding kids through their own ideas, and as a market organizer watching the next generation take their first brave steps.
What I know for sure is this: it’s never too young to let kids try. When they’re young, we’re still close enough to offer guidance, keep them safe, and remind them that their worth isn’t tied to sales. Some will grow up wanting the security of a 9‑to‑5 or a corporate role, and that’s perfectly okay. Others will keep building, experimenting, and dreaming.
The goal isn’t to raise entrepreneurs.
The goal is to raise capable, confident humans who know they can work for something they want — and figure out how to get there.
Markets don’t just sell goods.
They grow people.
