When I made a call to my dad—then in his sixties—about joining my startup, it wasn’t about securing funding or advice. I made the call to ask him to serve as a cofounder. After 13 years climbing the corporate ladder at American Express (Amex), I was ready to walk away from everything predictable. The irony wasn’t lost on either of us.
To be clear, this decision didn’t happen overnight. The four years between leaving Amex and starting this new venture were a journey in themselves. I built a coaching business from scratch as a solopreneur, eventually matching my prior executive earnings by leveraging a novel peer-to-peer model. And in my experience coaching over 400 senior leaders, I saw a universal pattern—a deep need for connection and group support that traditional corporate structures couldn’t provide. That insight planted the seed that later grew into the business I wanted to build with my dad.
In the process, I discovered five valuable lessons. Leaders can draw on these when they want to evaluate their relationship with success, make major pivots, and build something meaningful, whether with family or anyone else you trust.
Use ‘the line’ to audit your life
My dad had a simple visualization that changed how I thought about time. Draw a horizontal line representing your life: 20 years of education, 45 years of working, and, if you’re lucky, 13 to 15 years of retirement. He’d pose the question, “Why would you ever want to struggle through those 45 years hoping you’re healthy enough to have a good 13?”
The math is sobering—you’ll spend more waking hours at work than with your family. Map your line and ask yourself. If you’re 35 with 30 working years left, are you optimizing these years for meaning, or just enduring them for some day? What percentage of your working hours energize versus drain you? If you continue your current path, who will you be at retirement? What would you regret not trying during these prime years?
Recognize when success becomes a cage
Corporate success is seductive because it’s measurable, whether that’s by your title, salary, or bonus structure. But these metrics can trap you in a life that looks impressive from the outside while slowly killing you inside.
My breaking point came while sitting in another quarterly planning meeting. I realized that I could predict exactly what the next five years would look like. The same conversations, bigger numbers, higher titles. The predictability that once felt like security now felt like suffocation.
Success in a cage looks like this: you can predict your next three career moves with frightening accuracy. You’re optimizing for external validation rather than internal fulfillment. You find yourself saying “I should be grateful” instead of “I’m grateful.” You’re waiting for the next promotion to feel satisfied.
The escape framework is simple: Instead of asking, “What if this new path doesn’t work?” ask, “What if I don’t try?” The risk of regret often outweighs the risk of failure.
Find your complementary partner (and your unbiased challenger)
The most successful pivots happen with the right partner—someone whose strengths complement your weaknesses and whose timeline balances your urgency.
My dad brought perspective, where I brought hunger. He’d already proven everything he needed to prove professionally. At 42, I was still driven to build something meaningful. This combination allowed us to make decisions that balanced bold moves with sustainable growth.
Look for someone who shares your values but brings a different experience. A person whose timeline complements yours but is currently at a different life stage can be an advantage. You want someone who can challenge your thinking without crushing your confidence, and who’s motivated by the mission rather than just potential rewards. Avoid partners who run from something rather than toward something, or those who need the venture to work for their financial survival.
But even the best partnerships create a bubble. While my dad believed I could do anything, I realized I needed to step outside our relationship to gain the final conviction to act. His support was unconditional, but it wasn’t the push I needed. That came from an external coach who could ask the hard questions I was avoiding, like, “What are you so afraid of?” Sometimes, it’s not enough to rely on your inner circle.
Redefine success metrics before you start
You need new ways to measure progress when you leave traditional career paths. Financial metrics matter, but they can’t be your only scorecard.
Working with family forced us to optimize for multiple dimensions simultaneously—business growth, relationship health, personal fulfillment, and long-term sustainability. This broader definition of success made better decisions inevitable.
Create your new success dashboard around impact, growth, relationships, and alignment. Ask yourself monthly: What energized me most? Where did I compromise my values for short-term gains? How has this journey changed how I think about my future? Are we solving real problems for real people? Are we becoming better versions of ourselves? Are our partnerships getting stronger under stress? Do our daily actions reflect our stated values?
Use family dynamics as business advantages
Building something with family isn’t just about personal relationships—it creates unique business advantages that can become competitive moats.
The trust advantage means that difficult conversations happen faster when you know the relationship will survive disagreements. My dad and I were able to debate strategy intensely because we weren’t worried about political fallout. The authenticity advantage emerges when you build something around authentic leadership while practicing it, and customers can sense the difference. The long-term advantage also shows up because family businesses naturally think in longer time horizons, which leads to more sustainable decisions.
If you’re not working with family, look for partners where you can be completely honest about fears, mistakes, and uncertainties. Your goal should be to create a judgment-free zone where you can address problems before they become crises.
Give yourself the permission to redefine everything
The most significant insight I gained from building something with my dad wasn’t about business. It was about permission. At 42, I was still subconsciously seeking approval to pursue what I wanted rather than what I was supposed to like.
Initially, I thought that permission had to come from someone I trusted (like my dad). Having someone I respected so deeply ready to join me was a powerful validator. But as I learned when I left the corporate world, the only validation that you need comes from yourself.
Your path forward starts with auditing your life. How many productive years do you have left, and how do you want to spend them? Don’t be afraid to design metrics that measure progress toward a life that matters, and permit yourself to ask: What would you try if you knew you couldn’t fail?
The hardest part about leaving corporate success isn’t the financial risk. It’s admitting that everything you’ve been working toward might not be what you want. But once you make that admission, everything becomes possible.
Remember, the question isn’t whether you can succeed in someone else’s system. It’s whether you dare to build something that reflects your personal vision of success.
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