How to Use Your Biggest Losses for Guaranteed Future Success
Kurt Donnell, CEO of Freestar
Redefining Success Beyond the Career Ladder
In a candid conversation on the Break Free Podcast, Freestar CEO Kurt Donnell shared powerful insights that challenge conventional wisdom about career growth, failure, and finding success. Donnell’s journey from a high-powered M&A lawyer to a successful tech executive reveals that the true path to leadership is anything but straight. Here are five lessons to transform your approach to business and entrepreneurship.
Ditch the Ladder, Embrace the Lattice
Forget the rigid career ladder; successful careers are built on a career lattice. Kurt Donnell emphasizes that growth isn't always straight up. There are moments when you'll be climbing sideways, sometimes even down and around. If you feel you've hit your peak or learned everything you can, don't stagnate. Slide over to a new area—a different "swim lane"—and you'll find a fresh vertical path waiting for you. This mindset of lifelong learning is what keeps you growing and prevents you from "rotting".
Your Greatest Failure Is Your Greatest Lesson
The biggest turning points in life often disguise themselves as catastrophic failures. Donnell initially viewed his time spent as a lawyer, which left him unhappy and seeking therapy, as a failure. However, in hindsight, that experience was one of the best things he ever did. It acted as a mini-MBA, exposing him to 50 to 100 different business models and teaching him crucial lessons he applied to his CEO role. Remember: you learn so much more from the losses than the wins every time. When you reframe setbacks as learning opportunities, you are always either winning or learning.
Focus on A to A+, Not B to C
Where do you focus your limited time and energy? Donnell advises against spending energy trying to move an area where you’re weak (a B) to just a passing grade (a C). Instead, dedicate your effort to the things that take you from an A to an A+. This is the difference between being good at something and being truly great. In business, this means identifying your highest and best use , sharpening those core skill sets , and partnering with or hiring your deficiencies. Don’t dilute your efforts trying to "boil the ocean".
Every "Yes" is a "No"
This lesson is a crucial personal reminder for every ambitious entrepreneur. Donnell notes that every time you say "yes" to something, you are saying "no" to something else. That extra work trip or late-night happy hour means saying "no" to seeing your kids or putting them to bed. For leaders who often struggle with stress and burnout, running every decision through this filter is vital for maintaining a sustainable life. Donnell advises saying "yes" to everything you can until about age 40, and then start saying "no" to a lot more things after that.
The Strength in Seeking Help
Leadership at the top can be lonely and demanding, making mental well-being paramount. Donnell stressed a crucial message: "If you ever think you need therapy, you need therapy. Go talk to somebody". This isn't about being "broken"; it's about a preventative tune-up to make sure the "brakes are working". If formal therapy isn't for you, find that supportive, confidential peer group (like YPO or a faith community) where you can be your authentic self and know someone is listening. This act of vulnerability is a sign of strength and is essential for enduring success.
Written by Jovilyn Dela Cruz
“I really think of [a career] more like a career lattice because there’s moments where you’re climbing sideways sometimes down and around and up and all that stuff. And I think if you ever feel like you’ve kind of hit your peak and you’ve learned everything you can, you slide over a little bit and there’s probably somewhere else you can keep going up after that if you stay ambitious and keep learning.”
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