16 Lessons on Selling (and Life) from My 5-Year-Old
a little Sunday treat to celebrate Dev's first Donut Hat sale

Happy Sunday, friends! Earlier this week, X announced a $1 million article prize. I don't typically write the kind of content that could win such a contest—listicles filled with life lessons and advice. But then, wouldn't you know it, my son Dev learned how to sell yesterday morning, and he has been dropping wisdom bombs for me to write down. We ended up with sixteen of them. Now, they're on X (go like, comment, and share—we need the $1 million, Dev has a world to build). I really liked how it came out, so I wanted to share it with you all too. It's kind of a co-written essay with a 5-year-old, who I hope becomes a more frequent contributor. I think I'll start writing more short things and sharing them in the paid, not boring world, so join us if you want the full spectrum of not boring, means to meaning. Subscribe now.
This morning, my five-year-old son made his first two-dollar sale and dropped sixteen lessons on selling and life that are more practical than any of the slop you'll find on LinkedIn. I'll share them with you, but first, I need to tell you about Dev, about his Donut Hats, and about his world.
One day when Dev was three, he told me that he wanted to build worlds. Real ones. Big ones. Planets. Like, actual, physical planets. "Then you're going to have to study buddy," I replied. "What do I need to learn?" he asked. Math, physics, engineering, business. No one's ever built a world before, so you're going to have to study really hard. And then he did. He asked me for math problems, then harder ones, then harder ones. The kid does 90 minutes of Russian Math every Sunday and loves it. Physics, he always liked. Gravity was one of his first words, and one of the first concepts he grokked. "Why did the cup drop, bud?" "Gravity," he'd respond.
We read a little bit of Richard Feynman's lectures together, and he devoured them. Dev's fascination with building worlds led him to understand the importance of learning and applying knowledge. He's always been curious, always eager to learn.
But let's get back to the lessons. Dev's first sale involved selling Donut Hats. He had crafted two hats from cardboard and colored paper, and he set up a small stand in our living room. His target audience was his sister and me. "How much do you want for the hat?" I asked, intrigued by his entrepreneurial spirit. He thought for a moment and replied, "Two dollars."
I bought one for him, and he proudly wore it. Then, he turned to his sister and asked, "How much do you want to pay for this hat?" She hesitated, unsure of the value. Dev patiently waited, and then he offered, "I'll sell it to you for one dollar." She agreed, and the sale was complete.
Dev's first two-dollar sale taught him a lot about negotiation, pricing, and customer satisfaction. Over the next few days, he refined his approach and shared his insights with me. Here are the sixteen lessons on selling (and life) from my 5-year-old:
1. **Know your product's worth:** Dev started by pricing his hat at two dollars, based on the time and materials he invested. He understood that his creation had value, and he wanted to be fair in his pricing.
2. **Be patient:** When his sister hesitated, Dev waited calmly, showing that he understood the importance of patience in negotiations.
3. **Adapt and adjust:** Dev lowered the price from two dollars to one dollar for his sister, demonstrating flexibility and the ability to adapt to different customers' needs and budgets.
4. **Focus on customer satisfaction:** Dev's goal was to make his sister happy, even if it meant selling the hat for less. He prioritized her happiness over a higher profit.
5. **Leverage relationships:** Dev knew his sister well and understood her willingness to pay. He used his relationship with her to his advantage.
6. **Be confident:** Dev's initial price of two dollars showed confidence in his product. He believed in its value and was willing to stand by his pricing.
7. **Understand the market:** Dev knew that his target audience was his sister and me, and he priced his hat accordingly. He understood the limited market for his product.
8. **Provide value:** Dev's hats were handmade and personalized, which added value to his product. He knew that his creativity and effort made his hats unique.
9. **Be honest:** Dev didn't try to overprice his hat. He was upfront about its value and adjusted the price when necessary.
10. **Learn from experience:** After his first sale, Dev reflected on his approach and adjusted his strategy for future sales.
11. **Stay positive:** Dev's enthusiasm for selling his hats was contagious. His positive attitude made the experience enjoyable for everyone involved.
12. **Be resilient:** If Dev had faced more hesitation or rejections, he would have needed to be resilient. He would have had to keep trying and adapting his approach.
13. **Value your time:** Dev's time and effort in creating the hats were important. He recognized that his investment in the product was worth the price he set.
14. **Understand the customer's perspective:** Dev considered his sister's budget and her desire for the hat. He adjusted his price to make the sale work for both parties.
15. **Be creative:** Dev's hats were a creative expression of his passion for building worlds. His creativity made his product unique and appealing.
16. **Embrace failure as a learning opportunity:** If Dev hadn't sold his hats, he would have learned from the experience and adjusted his approach. He would have understood that not every sale is successful, but that's part of the learning process.
These lessons from a 5-year-old are not just about selling; they're about life. They teach us about negotiation, adaptability, customer focus, and the value of relationships. Dev's approach to selling his hats mirrors the strategies we use in our daily lives—whether it's negotiating a salary, building a business, or connecting with others.
As Dev grows older, his world-building aspirations will likely evolve. He'll continue to learn and adapt, just as he did when selling his Donut Hats. His lessons serve as a reminder that curiosity, patience, and a willingness to learn are the keys to success in any endeavor.
Join Dev and me on X (go like, comment, and share—we need the $1 million, Dev has a world to build) to read the full article and see how these lessons can apply to your life. Subscribe now to stay updated on more not-boring, meaningful content from us.









