A little bit ago, I sat down with Richard Watts—a lawyer, advisor, and author who’s spent decades helping families wrestle with their legacy.
We didn’t talk about trusts or tax brackets. Instead, Richard told me a story that landed like a gut punch, about what happens when love becomes over-accommodation, and how easy it is for parents to unintentionally rob their kids of some of life’s most important gifts.
He described watching, again and again, as families with the best intentions pass down wealth hoping to secure their children’s futures—only to find the exact opposite:
“Anytime you let somebody up from doing the work themselves… there’s a certain amount of entitlement that occurs and you’re actually going to take away some of their joy.”
Or as another friend told me, “why rob your kids of the opportunity to do it themselves.”
I thought about this a lot after our conversation. My instinct as a parent is to help, to smooth out the bumps, to say yes when I can. But Richard’s stories kept reminding me: Pride and resilience are built by climbing the mountain, not by being helicoptered onto the summit.
Intention matters.
Not just in what we give our kids, but in what we withhold. Richard has seen firsthand the subtle damage that comes from removing every hurdle. It might feel loving in the short term—but in the long run, as he put it, “for everything you give your child, you take something away.”
The core lesson? It’s tempting to want to give our kids everything we didn’t have. But we can’t afford to forget the value of what we did have—the grit, the hunger, the sense of achievement that only comes from trying, failing, and getting back up.
When we set clear expectations, talk openly about money, and hold the line on what support looks like, we show our kids that our intention is not just to make life easy—but to help them build the skills and the confidence to stand on their own two feet.
This conversation reshaped how I think about intentional parenting, especially when life doesn’t tell you no. Here’s a simple approach distilled from Richard’s wisdom—practical whether you’re managing a trust fund or just working through allowance debates:
1. Name the Limit – Decide, and clearly communicate, what support you will and won’t provide. This goes for everything from help with cars to college tuition. Avoid surprises by being upfront (“When you go to college, I’ll cover tuition and board, but after that, rent’s on you”).
2. Invite Struggle – Don’t jump in to solve every problem. Let your kids experience setbacks and figure things out (“I’ll match what you earn toward your first car”, “If you want something beyond the basics—we’ll brainstorm how you can earn it.”) Remind yourself: you’re not just withholding, you’re giving them a chance for real pride.
3. Model & Talk About It Early – Start the conversation about expectations, responsibility, and money when your kids are young—not at the last minute. Talk openly about both the support you received (and didn’t), and what helped you become who you are.
One of our experiences at Factory for Good helps with this framing. The Bank of Mom and Dad—where the family acts as lender, not a limitless ATM, and every dollar comes with clear terms and lessons attached.
I hope Richard’s stories leave you thinking, and maybe re-evaluating some of your own family policies—as I have. Here’s to being intentional, to balancing support with struggle, and to helping those we love the most grow into the people they’re proud to be.
If you want to learn from more leaders like Richard—and build intentional frameworks for your family, business, and life—subscribe to Factory Friday, our weekly newsletter for people shaping a legacy that lasts.
- Alex
