Not to Lose

I’ve been around soccer the majority of my life.

Whether it was traveling with the college team my dad coached as a kid, playing club soccer at an early age, focusing on the sport in high school, playing all through college, or being the product of my first entrepreneurial venture, soccer was a part of my identity for over 20 years. This team sport helped me push to be my best, but the sense of belonging is what made it special.

As I’ve enjoyed the World Cup in Qatar, I’m reminded how easy it can be to get ahead in a match, before slipping into a dangerous trap. Instead of staying sharp by maintaining the offensive pressure that earned an early lead, it’s tempting to start playing not to lose.

In soccer, this often means a team sinks back into an overly defensive formation. Less variety invites frantic desperation and the added pressure often leads to an equalizing goal being scored by the opposing squad. Even if the need for another goal shifts your team back into a more balanced attack, the momentum has shifted.

When applied to business, getting ahead and then playing not to lose can be seen all over the map. For instance, snagging a few early adopters, then assuming customer discovery is over. Hiring new talent, then hoping everyone can work together without initiative. Launching a new product with existing customers, then not supporting them through the chasm of change. Securing product-market fit, then avoiding innovation due to a misguided sense of risk. Finding generous mentors, then forgetting to nurture relationships. Those are just a few, but many leaders are lulled into this trap that’s defined by a sense of scarcity.

Tactics to stay ahead differ based on situational factors, but when in doubt, trust that uncertainty is certain. Be strategic to avoid recklessness, then stay on the offensive by leaning into the pain. As you find fresh ways to serve customers, continue celebrating milestones and stay ahead with initiative to keep building beyond the fear of losing.

Intrinsic

We all have bad days. When they string together, the stress gets heavy. This mental weight becomes especially unwieldy when the cause is unclear. After a couple down days, I went searching for the origin of my cloudy mood.

Along with insight on entrepreneurship, venture capital, and community building, Brad Feld talks a lot about mental fitness. The entrepreneurial lifestyle is a lonely roller coaster and I’m thankful for leaders like Brad (and many others), who have helped destigmatize the complex circuitry between leadership and mental health.

I found this entrepreneurship & mental health series from Techstars helpful, then wove in this 2015 interview to translate my temporary despair. Brad talked about how he’s gone through serious bouts with depression and through those challenging times, he’s been able to identify one of his intrinsic motivations to be perpetual learning. He went on to describe how even when he was busy and perceived to be successful, if boredom began to set in, an isolating absent of joy may soon follow.

This gave me clarity. I realized that one layer of my own intrinsic motivation is also learning. I like being in situations where I’m exposed to new things, thinking about fresh ideas, solving interesting problems, hearing stories from different people, and building into things I really care about. When there’s a lull in the action, it’s easy to think the ride is over. While this thought is misguided and untrue, it’s still disheartening. Mental fitness means something different for everyone, but here are a few exercises I plan to maintain within my practice.

  • Link learning with teaching.
  • Recognize that the storm will pass.
  • Find trusted peers to release tension.
  • Use this stimuli of stress to focus.

Adam Grant reminds us that strength does not come from ignoring pain. It stems from knowing that your past self has hurt and your future self will heal. Within the crucible of entrepreneurship, hardship is inevitable. Radical self inquiry keeps leaders aware of their mental fortitude. Such awareness then helps us maintain and uncover new stepping stones that illuminate our own path to thrive beyond momentary setbacks.

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Calm is one of my favorite apps. The guided meditations and sleep stories are a healthy aspect of my daily routine. Here are 10 ways to boost your mental fitness, a mental fitness training guide, and free mindfulness resources from these focused friends.

Tenured

Recognize, connect, and support those who consistently delight those they serve over a prolonged period of time. Rewarding such an initiative makes sense, but at what point does the comfort of a rewarded role devolve into a willingness to sail into the sunset?

When starters run into the aloof, misaligned energy can lead to a standoff. Time is the ultimate release, but what if progress is needed now? Every situation is different because of the complexity of an environment and the people/organizations involved, but here are tactics that seem to work no matter the circumstance.

The first uses social currency. It requires a change maker to set their ego aside, and instead, celebrate all that’s been achieved by the accomplished, yet tired gatekeeper. Use respect, kindness, and appreciation to form a bond. Relationships that feel less transactional often create leniency toward new ideas. When a crack in the wall of inactivity is created, be glue that maintains the integrity of the existing system. For example, “I’m too busy” is a common qualm, so lean into that pain by offering to execute on the idea that has sparked mutual interest. It’s important to be realistic in these moments, because when promises are made, credibility is on the line. As you not only light a path toward progress, but also champion change by evolving ideas into reality, trust is gained and your ability to continue making a ruckus increases. Want to extend your leash further? Take responsibility for failures, but give all the credit away when success is achieved.

If a larger organization is involved, another interesting tactic invites the tenured leader to level up the team by activating a colleague. This provides a new hire the chance to get involved within the entrepreneurial ecosystem, while the organization is seen as engaged within their community. It’s hard for some to understand that time spent in the wild is often more valuable than clocking time in the office, but if the organization allows this person to show up without limitation, everyone wins. The new community member feels the innovative energy and brings more intrapreneurial vibes into the organization, while the community benefits by having another trusted organization in the mix.

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“The way we make things better is by caring enough about those we serve to imagine the story that they need to hear.” -Seth Godin

If you’re reading this, you may be tenured, but it’s unlikely you’re tired. That said, we’ve all found ourselves in a motivational rut or lacking a clear sense of purpose. Along with a few solid sleeps, when I feel the urge to settle, it helps to have fun, build into other areas of your career portfolio, take a few days to rest if necessary, and then get back into the startup community. This creates opportunities to #GiveFirst, ask for help, or get extra curious about the creative work of others. Soon you’ll find new opportunities to collaborate.

New connections that emerge can bring you out of the motivational rut. They can boost your care meter and will add fresh personality to your work. Along with sparking fresh direction(s), you’ll be motivated by others and soon find new ways to be generous with your art. If you’re still thirsty for motivation after tapping into the entrepreneurial ecosystem, I’m here for you as well. Together, we can refuel the idea machine to avoid wasting any more time with being tenured, but tired. Sleep when you’re dead, my friends. Let’s keep building.

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“There will come a time when you believe everything is finished. That will be the beginning.” -Louis L’Amour

Bloop

Imagine yourself as a circle.

It’s tempting to suggest a sphere, but the added dimension is not necessary for this metaphor. Alright, with your circular self, take a tiny portion of the arc and “bloop”… push it beyond the circle’s circumference. Even the smallest nudge gives the entire circle space to expand.

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I had fun making all sorts of sounds as I considered the title for this reflection, but I’d love to hear how you’d describe the sound of such an expansion. Also, since I had to look up the terms to ensure this metaphor was translated correctly, here are the parts of a circle.

There’s plenty of research behind the idea of small improvements adding up. As we hear from inspired speakers and read about in Atomic Habits by James Clear, if you get one percent better each day, you’ll end up thirty-seven times better by the end of a year. It’s hard to define “better” and such steady progress would surely require sacrifice, but most will agree that small choices don’t make much of a difference, until they add up.

While establishing systems that support good habits and compiled improvements are great, this reflection is more about welcoming singular moments of exploration and growth, even when it seems unrelated, weird, or insignificant.

Perhaps it’s trying something new without preconceptions, saying yes when no is status quo, or being the initiator when movement is seen as risk? As we poke the box and invite a bit more bloop in our life, we give ourselves an opportunity to grow as our own circles expand.

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To thank those who have enjoyed brewing on these Roasted Reflections every week for almost two years AND to say hello to some new friends, here’s a free gift just for fun!

Shifting Gears

Can you hear a distant motorcycle bolting into the night?

Hearing the sound of speed puts that wind in my face, but twas the night before we kicked off the 2022 class for Techstars Iowa Accelerator. This had me reflecting on the gear shifting that occurs in any growth process.

That first gear of any manual transmission is dedicated to initiating motion. It won’t get you very far, but as the red line arrives, a shift bring you into the next gear that builds on the momentum. As that next gear tops out, yet another shifts moves you further, with higher gears that eventually brings you to full speed.

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I owned a fast motorcycle in college. I treated the danger with redeeming respect, but after pushing this Yamaha FZR600 to 150mph, it was time to sell it…on eBay. In addition to speeding up, shifting gears also helps us slow down. Now I’m more of a convertible guy, cruising toward that wonderful wind in my face.

Any journey is a dance, but your destination would not have been reached without an ability to temporarily lose power in exchange for more lasting capacity.  Whether it’s personal or business growth, intellectual humility and recognizing when you’ve reached a limit, provides awareness required to drop the clutch.