Putting STRIVE into play: Advice from a gold medalist, NFL star, and two high-growth CEOs

When CEOs think about becoming better leaders, they often focus on signals of external validation — higher valuations, better products, or hitting new revenue milestones. However, there's another path to transformational leadership: cultivating self-compassion and empathy to build deeper relationships with the people and teams helping bring your vision to life. It’s tough to pin a KPI to those types of achievements, but their impact is longstanding and goes on to influence the ethos and culture of a company.

Emotional regulation and discipline are hallmarks of exceptional leadership. But keep in mind that as a CEO, you’re still human, with your own unique challenges and areas of development. Which is why Bessemer and Exos brought together top athletes and executives to discuss how they manage their well-being at our STRIVE event.

Transformational leadership stems from self compassion and empathy. 

This panel, led by Ryan Nece, Managing Partner at Next Legacy, was an opportunity for these four leaders to open up on real challenges, how they overcome them on a daily basis, and uncover the strategies they’ve developed throughout their careers.

Here, we share Brenna Huckaby’s story of overcoming insurmountable adversity as a gold medal Paralympian and Tony Smith’s experiences balancing family and business as CEO and co-founder of Restaurant365. Maria Colacurcio, CEO of the HR analytics startup Syndio, offers advice on motivating teams through compassion, while NFL defensive lineman Arik Armstead opens up about the mental health support systems that help him excel on and off the field.

Each leader stayed true to their own vision and developed personalized regimens to support their unique STRIVE journeys. They offer valuable insights into cultivating a mind-body-spirit connection that empowers you to show up as your best self in life and leadership.

TLDR

Brenna Huckaby, a three-time gold medal paralympian, shares how overcoming adversity taught her that her self-worth transcends achievement. Tony Smith, CEO and co-founder of Restaurant365, has found that what matters is keeping family time sacred. Arik Armstead balances critique with self-praise, and watches his tapes, but also his highlight reels. And Maria Colacurcio keeps up positive text conversations with other leaders because when she’s feeling down, sometimes that positive note is just the thing to buoy her spirits.

The consensus? Prioritizing wellness helps us show up as our best selves for our teams and loved ones. And you’re not alone: Even high performers feel these seven ways when it comes to wellness

1. It’s hard to practice how you play, but it’s worth it

We are what we practice repeatedly and if you want to show up as your best self when the stakes are high, pretend the stakes are high when they aren’t. Take “practice time” seriously — show up on time and give like you’d give in a real game.

Take practice seriously. 

“If you laze off in practice, you won’t do well in the game. Leadership is similar,” Maria explains, “I realized that if I gave feedback and had difficult conversations when the stakes were low, then when the stakes were high, I didn’t feel anxious about my ability to manage tough conversations with my managers.”

This means devoting yourself to practicing small, yet difficult things on a consistent basis — like having nuanced and vulnerable work conversations, committing to your exercise regimen, or having good sleep hygiene — so when it’s a big moment, you’re ready. Any leader can apply this approach to their health routine, too, including your sleep, training, eating habits, and managing your emotions. Everyday is an opportunity to practice and be 1% better.

Guiding question: How am I taking small, consistent steps to get closer to my goal?

2. Finding balance means guarding your downtime

Balancing family and relationships with a successful, fast-paced career is a constant challenge. Sometimes that requires padding. Tony keeps Saturdays sacred for this very reason. Their family routine includes a homemade breakfast and vintage movie marathons, before they end the day together playing basketball or exercising together. “We’ve done that Saturday ritual every weekend for 19 years, and I have no plans to stop now,” Tony says.

Finding ways to be present with your loved ones can help enable that restorative time, which is a type of non-sleep rest that everyone needs.

For Maria, technology helps keep her and her family present. Two nights a week, every member of the Colacurcio leaves their phones out of reach and locked down with the help of an app called Opal. “I found it so hard at first. You can spend all day and night on emails, Slack, and Google Docs. This intentional time helped all of us to really connect with each other for a few hours each week,” Maria shares.

But even on your best days, it’s easy to feel like you’re not doing enough, especially when you’ve got a family and a business to run. Or in Arik’s case, a wife, two daughters, and an entire football team. “Don’t get me wrong, it’s hard to balance. I worry I’m not being a good dad when I’m working, and that I’m not being the best player when I’m with my family,” Arik explains, “But it’s an impossible standard to be perfect at everything. Just be intentional, wherever you are.” Sometimes the best advice is that releasing yourself from being perfect at work, family and relationships will free you to be good instead. As the old adage says, don’t let perfect be the enemy of good.

Guiding question: Where in my week can I be present with my loved ones without distractions?

3. Being at the top of your game can be lonely

You didn’t get to where you are by doing things like everyone else. But originality can sometimes be lonely. Whether it’s being the only woman in the C-suite or defending your ideas to a boardroom full of cynics. But if you can recognize when you’re feeling isolated and name it, you can help alleviate that feeling.

Maria’s approach is to look outwards, at the people on her team, and to surround herself with people who reflect the values she admires. After all, celebrating others builds team momentum.

“There’s a saying I repeat often: The most wonderful light to stand in is reflected light. When those you lead do amazing things — when they excel and feel empowered — that light reflects on you. So surround yourself with those people and give them autonomy to grow and flourish. And then watch as light surrounds you too,” she says.

"The most wonderful light to stand in is reflected light."

On the other hand, isolation can be a helpful tool of self-reflection. As Arik explains, “Sometimes, I enjoy being in those moments of isolation. It forces me to look at myself, how I operate, and my decisions. Then I remember why I made those choices and why the sacrifices have been worth it. When it’s quiet, I have the time to think.”

Being at the top can be lonely. But it’s also where you can stand in the light of other leaders, when you need it. Quiet reflection can also be purposeful and solidify who you are and where you’re going.

Guiding questions: Who can I celebrate this week for demonstrating the values I admire and want to cultivate within my team? Where can I schedule time for quiet reflection to stay focused on my vision?

4. Adversity can teach us how we grow

Too much adversity all at once can be devastating and ultimately hinder our growth. But when we have the proper mental health support and wellness practices, we can channel adversity into the drive necessary to propel us forward toward a dream.

Brenna Huckaby’s story of striving has the contours of both. After an athletic career in gymnastics came to an untimely end, due to the loss of her leg in 2010, she had to grapple with devastating grief. However, it was during that life-altering crucible that Brenna discovered snowboarding. Her vision for gold persisted, and, as she puts it, made the 2018 Paralympics her whole personality.

“I dedicated the majority of my life from that point on to winning gold. I firmly believed that once I won, everything I went through would be worth it. But instead, I won those gold medals and I fell into the deepest depression of my life,” she shares, “I finally realized that achieving my goal didn’t fix anything in my life.” She thought adversity, and her efforts to overcome it, would be enough to fix her mental and emotional state. And when it didn’t, she had to step back and reflect, with the help of a therapist among other resources.

As a result, she went on a healing journey to deepen her relationship with herself. She worked to understand her worth outside of her accomplishments, to love her body outside of its abilities, and to find the mental health support she needed. Then, when she felt confident in her physical, emotional and mental wellness, she decided to compete in another Paralympics. “Whether or not I won, I had a completely different mindset. I remembered what it felt like to get everything I wanted and not be able to savor it. So, when I won again — a gold and a bronze medal — it was so much sweeter. I wasn’t trying to prove anything anymore,” Brenna exclaims.

The heart of a champion is earned through seeking self-worth. 

Brenna’s inspiring story of overcoming adversity demonstrates how the heart of a champion is earned through not just the medals around one’s neck, but also being committed to seeking self-worth and self compassion.

Guiding question: Outside of your abilities and accomplishments, where do you derive your self worth?

5. You may find critique comes easier than celebrating your wins

Those daring greatly and “in the arena,” as Brené Brown says, may feel like living under a microscope. Whether you’re playing in front of millions of adoring fans or sitting in front of a Zoom call full of questioning eyes, these situations can get anyone feeling stressed and anxious, no matter their title. But learning to metabolize criticism into fuel for growth is what defines your success as a leader. And the only way to develop that emotional skill is to learn how to process difficult emotions on a regular basis. But, in the hustle of everyday life, don’t forget to celebrate your wins.

“As an athlete, wins are very important for your confidence. We spend all day rewatching film of every little movement we make. But sometimes I go back and watch my highlights instead. You have to remind yourself why you’re here. You’re good enough to be in the position you are right now,” Arik says.

But you don’t need a highlight reel to recall your wins. Amongst her peers, Maria exchanges text messages of support and encouragement, from one leader to another. “These texts come at the exact right moment, when I’m feeling low. And it’s always what I need to hear. So I carry that energy forward, I send a message to someone else with a bit of encouragement too. You never know what people are going through. And those exchanges always give me the push I need,” she says.

Guiding question: What is a win from this week you can relish in?

6. Admiration can be a source of inspiration

Comparison can be the thief of joy, but it can also be an inroad to developing self esteem, when framed correctly. For Tony, comparison can be healthy if it causes us to emulate the positive virtues we see in others.

Instead of leaning into envy, he suggests that whenever you’re in the position to interact with someone who you admire, lean into those comparisons.

“Treat every interaction as an opportunity to learn from them. Acknowledge they may be better than you in a particular area and then focus that energy into observing, learning, and applying their approach to your own journey,” Tony explains, “There’s no room for wallowing when you’re learning from someone you admire.” Instead of letting comparison steal your joy, flip that emotional energy around and see how you could mirror someone’s habits and make them your own.

Guiding questions: Who is your role model? What do you want to learn from them? What outlook or habit could you adopt to be more like them?

7. Asking for help is part of every wellness journey

Having a support system is vital. For athletes like Brenna and Arik they’ve paired their physical regimen with a mental and emotional one. For executives, you may not need a sports psychologist, but regular therapy, meditation, and self-reflection can help you regulate your nervous system and manage mental challenges as they arise.

You can start by asking trusted colleagues who they turn to for support — whether that’s a personal trainer to keep a consistent regimen, a therapist that understands the specific needs of high performers, or a nutritionist who can help you build a sustainable intake plan. Everyone needs different support, the key is to choose the ones that work for your wellness journey.

Guiding questions: What pillar in our STRIVE program — Sleep, Training, Regimen, Intake, Vision, Emotional Regulation — do you want to further develop for your well-being? Are you looking for an accountability partner, therapist, trainer, or another type of expert to help you?

You’re a human first and a high-performer second

Wellness isn't just a buzzword — it's a crucial element for high performers across all fields. Whether you're crushing it on the football field like Arik Armstead or leading a tech company like Maria Colacurcio, taking care of your mental and emotional health is key to sustained success. Leaders like Tony and his family’s Saturday rituals remind us that balance isn't just possible, it's necessary. While Brenna Huckaby's journey reveals that even gold medals can't fill the void if you're not right with yourself.

The takeaway for leaders? Never strive alone. Whether it's therapy, family time, or a quick encouraging text, we all need support. So, take some advice from these leaders — practice self-compassion, celebrate your wins, and remember that your wellness journey is just as important as your professional one. After all, you're human first.