What Your Kids Will Remember About You
Building Generational HabitsInside this issue
On My MindMost conversations about legacy eventually end up in the same place: money. Building wealth. Leaving something behind. Creating opportunities for your kids. Those things matter. Of course they do, but my conversation this week with Jason VanDevere pushed me toward a different question: What habits are our kids inheriting from us right now? Jason grew up around a successful family business. His family owns multiple car dealerships in Ohio, and for a long time, the expectation was that he’d eventually step into that world himself. He worked in the business, learned the systems, and by his own admission, he was good at it. But he didn’t love it. He kept returning to the idea that he wanted to build something aligned with the life he actually wanted to live and the kind of father he wanted to become. Walking away from the family business wasn’t really about escaping the car industry. It was about creating a life where work supported his priorities instead of controlling them. I think a lot of dads wrestle with that tension, whether they own a business or not. It’s easy to tell ourselves we’re sacrificing time, energy, and attention for our families while ignoring how those same sacrifices shape the environment our kids grow up inside of. Eventually, work can start influencing the family more than supporting it. Kids notice that. They notice whether we’re mentally present or constantly distracted. They notice how we react under pressure, how we talk to our spouse, how we handle disappointment, and whether we actually live the values we claim matter most. Long before kids understand our careers, they understand our patterns. One of the most meaningful parts of the conversation came when Jason said, “What you’re really aiming for is generational habits.”  That idea carries a lot of weight. Most of the habits our kids inherit won’t come from lectures or advice. They’ll come from repetition. From watching how we move through life every single day. The way we manage stress. The way we treat people. The way we spend our time. The way we recover from mistakes. The way we show up when we’re exhausted. That’s legacy, too. And in a lot of ways, it’s probably the part that lasts the longest. Define the Lifestyle FirstJason shared that too many people treat work as the destination instead of the tool. The result is predictable. Work expands until it consumes the exact life it was supposed to support. Jason took the opposite approach. Before scaling his businesses, he got clear on the kind of lifestyle he actually wanted to build:
Then he built systems around those constraints. Why it MattersIf you never define what “enough” looks like, work keeps moving the target.
Without constraints, there’s always another reason to stay online longer, answer one more email, or sacrifice another evening at home. Why it WorksConstraints force better decisions. Jason talked about setting hard office hours and treating them seriously. That structure forced him to become more intentional with his time, delegate better, and focus on higher-value work. Instead of asking, “How much can I fit into my life?”; ask, “What kind of life am I trying to protect?” That question changes the way you build everything around it. How to StartTake 15 minutes this weekend and write down:
Don’t start with career goals. Start with the life those goals are supposed to support. Pro TipYou don’t need perfect balance. You need intentional boundaries that people can count on. The End-of-Workday ResetJason built a deliberate transition between work mode and dad mode. Since he works from home, there’s no commute separating business owner mode from family life. So instead of letting work bleed into the rest of the evening, he created a simple shutdown routine at the end of every day. Every afternoon at 4:35 PM, an alarm goes off signaling that the workday is ending. From there, he spends about 10 minutes:
Simple, but incredibly effective. Why it Matters A lot of us technically stop working without ever mentally leaving work. You might be sitting in the living room while still replaying conversations, solving problems, or mentally responding to emails. Your body’s home, but your attention isn’t. That disconnect adds up over time. Why it Works The routine creates separation. Instead of carrying unfinished work mentally into the evening, you create a clean stopping point. That gives your brain permission to transition into the next role instead of trying to hold both at the same time. It also creates consistency for the people around you. Your family starts to trust that when work is done, you’re actually present. How to Try It Create your own 10-minute shutdown routine this week. Keep it simple:
The activity itself matters less than the repetition. Pro Tip Use a timer or recurring alarm. Good routines usually fail without a clear trigger. Time to Sprint: Get Out of Survival ModeA lot of dads are living in survival mode without realizing it. During the conversation, Jason said, “If you don’t dream, you don’t have meaningful goals. You end up in survival mode.”  Survival mode doesn’t often look dramatic. It usually looks like moving from one obligation to the next without ever slowing down long enough to ask what you actually want your life to become. Why it Matters When every decision is reactive, it’s hard to build anything with intention. You end up chasing deadlines, responsibilities, and other people’s expectations while your own priorities slowly disappear into the background. Why it Works Clarity creates momentum. The moment you start naming what you actually want, your decisions become easier. You stop saying yes to everything. You stop building blindly. You start noticing which opportunities align with the life you’re trying to create. How to Do It Minutes 0–15: Dream Without Editing Grab a notebook and answer these questions without filtering yourself:
Don’t worry about practicality yet. The goal here is clarity, not logistics. Minutes 15–20: Look for Patterns Review what you wrote and circle:
Most people already know what matters to them. They just rarely slow down long enough to hear it clearly. Bonus 5 Minutes: Choose One Directional Change Not a five-year plan. Just one directional shift. Examples:
Momentum usually starts smaller than people think. Pro Tip Pay attention to the ideas that keep resurfacing. Those recurring thoughts usually point toward something that matters more deeply than we want to admit. Your MoveWhat’s one habit you’re intentionally trying to model for your kids right now? Hit reply and let me know. I read every response. Connect with JasonThis week’s guest is Jason VanDevere, entrepreneur, real estate investor, and founder of Goal Crazy. What I appreciated about Jason’s perspective is that he talks about entrepreneurship in a very grounded way. Not as some shortcut to freedom or status, but as a tool for building a more intentional life and creating the kind of environment he wants his kids to grow up inside of. If you’re interested in business ownership, goal-setting, productivity, or building systems around the life you actually want, his work is worth checking out. Follow Jason On his website: https://goalcrazy.com/ On Instagram: https://www.instagram.com/goal.crazy Goal Crazy on Amazon: https://amzn.to/4v8Lo3w Read his book, Dream Driven: https://amzn.to/4dK7lPj Grab the Idea to Profit Blueprint: https://www.goalcrazy.com/blueprint Check out his podcast: https://podcasts.apple.com/us/podcast/goal-crazy-how-to-start-and-grow-a-dream-driven-business/id1636934991 On the Show This WeekContinue the ConversationAt its core, this week’s conversation is about building a life that your work supports instead of consumes. Jason and I talked about the pressure a lot of dads feel to keep achieving, providing, and pushing forward while also trying to stay present at home. We also talked about how fatherhood changes ambition itself. The goals don’t necessarily disappear, but the reason behind them starts to shift. The conversation dives into:
There’s a lot in this episode for dads trying to build meaningful work without losing themselves or their families in the process. Check it Out🎧 Jason VanDevere on Building Generational Habits Through Fatherhood and Entrepreneurship Listen on your favorite podcast platform The Last LaughCareful what you take from your kids or you could end up the subject of an R&B jam. |
