What a Lemonade Stand Taught Me About Being a W2 CEO

This summer, my 7-year-old son did something I’ve been talking about for years, but hadn’t truly internalized: he took action on an idea.

All spring, he talked about running a lemonade stand. And as soon as the warm weather hit, he was out there with his folding table, his paper signs, and his giant grin serving up plastic cups of lemonade to passersby. First weekend? He made $52.

At first, it was just a fun summer activity. But it quickly became something more.

I wanted to turn this into a long-term lesson. So we created five buckets for his earnings:

1. Buy something fun – a small, guilt-free purchase
2. Save for something big – something he can look forward to
3. Give to others – to build generosity and gratitude
4. Invest for the long term – to understand compounding
5. Reinvest in the business – to think like an owner

Each week, we sit down with a simple sheet of paper.We record the starting balance for each bucket, track what came in, what went out, and calculate the ending balances. It’s not fancy. Most weeks we don't run the lemonade stand, so there isn't much to record. But it’s already become a powerful tool to have real conversations about money. These were conversations I didn't start having until adulthood, and even now I rarely have with peers!

And for his “investment” bucket, I’ve been giving him 10% interest per week. Yes, it’s outrageously high. But 10% of $10 is $1, a small price to teach him about compounding early, and get him excited about watching his money grow. (I'm hoping that this lesson sinks in before it bankrupts me!)

He’s already started asking the right questions. What does it cost to make cookies if he wants to sell them? Should he invest in a cotton candy machine? How many weekends would it take to make that money back? Will people still want lemonade as summer ends, or should he pivot to hot chocolate or apple cider?

Even though I’m a W2 employee, and proud of the work I do, I realized I wasn’t really practicing what I’ve been teaching him. I hadn’t built multiple income streams. I wasn’t regularly reinvesting in myself or my skills. I’d grown risk-averse. Focused. Responsible. Efficient. But maybe too cautious.

Meanwhile, my son? He just tries things. He puts himself out there. It’s not perfect. He doesn’t overthink it. He makes adjustments as he goes. And most importantly, he adds value. That’s the part that really hit me.

What struck me most wasn’t his enthusiasm or even his willingness to take a risk. It was his instinct to explore, to test, to learn in motion. There was no paralysis. No waiting for the perfect market research, business plan, or logo. No fear of looking stupid. He saw an opportunity and stepped into it, and then figured out the rest in real time.

And here’s the truth: most of us unlearn that. We trade curiosity for competence. We swap play for productivity. Somewhere along the way, we start to believe that we’re only allowed to act if we already know the outcome. That mindset might help you climb a corporate ladder—but it’s poison if you’re trying to build anything of your own.

So this summer, watching him made me confront a hard question: Why don’t I run my own financial life with the same creativity, urgency, and flexibility I’m trying to teach him?

The honest answer? I think I got good at playing the W2 game. And I forgot it is a game.

I know how to budget. I know how to invest. I know how to optimize taxes and 401(k) contributions. But somewhere in there, I stopped playing. I stopped exploring new ways to earn, new ways to grow, new ways to challenge myself. And I certainly wasn’t treating capital—my time, my energy, my attention—as something to be allocated like a CEO.

That’s what the lemonade stand revealed to me. This wasn’t just a money lesson for my son. It was a wake-up call for me.

Because building a life with options—real options, not just better titles and bonuses—requires the same skills we’re practicing at our kitchen table each week:

• Set up systems that make your decisions visible
• Allocate intentionally, not reactively
• Create a feedback loop so you can course-correct
• Reinvest your wins
• And when in doubt, experiment

The buckets my son uses? I need them too. Not just financially, but mentally.

I need a bucket for joy, so I don’t forget to spend in ways that actually make life better.

I need a bucket for big dreams, so I don’t shrink my future just because my present is comfortable.

I need a bucket for giving, because generosity forces you to remember you have enough.

I need a bucket for investing, not just in markets, but in skills, in people, in asymmetric bets that might not pay off immediately—but could compound in ways that matter.

And I need a bucket for the business—for building something that is mine, that creates value beyond my hours, that teaches me just as much as it teaches others.

The reality is, most of us aren’t taught to think this way. We’re taught to earn, to save, to consume. But not to allocate like an owner. Not to experiment. Not to trust ourselves with the responsibility of building something from scratch.

That’s what I’m trying to re-learn now. Not just for my own sake—but so when my son eventually asks me how I make these decisions with my money, I have an answer worth giving.

This lemonade stand is small. But the conversations, the choices, the patterns? They’re the whole game.

And they start at $52.