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.

Sticks on Ice

A friend suggested I write about micro vs. macro.

These two words have related, but opposite meanings. Everything happening right now (micro) is transitory, yet these micro-moments coalesce into the story of our comprehensive progress (macro).

The distraction of each micro-moment is impossible to avoid, but the Canadian saying, keep your stick on the ice, reminds us to chill, keep it simple, and be ready for anything. No matter where stuff lands on the spectrum between good and bad, micro eventually accumulates into macro. Alright, take a deep breath, enjoy a sip, and let’s brew on how staying mindful of the macro, helps us appreciate the micro.

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Want me to lean into a topic on your mind? I’m ready when you are.

Last week’s writing on intrinsic motivations seemed to resonate, as it was encouraging to hear from many of you. After a few dispirited days, I was back at full speed with Global Entrepreneurship Week. Our web3dsm gathering, 1 Million Cups, an angel investor event, premiering our Techstars Iowa Accelerator 2022 Demo Day video, and watching friends like you bring so many things together, was a groovy way to celebrate entrepreneurs who serve their local communities and bolster the global economy.

A focal point for me, was an opportunity to speak at the United Fall Leadership Conference. To maximize the impact, I cranked up the volume in a new talk tuned specifically for students and educators. I call it “No Permission Required”. The energy of accelerating others is unmatched, but there’s an extra boost as we’re exploring education and making a ruckus to activate linchpins along the way! It was cool to connect with 200+ high school students from all around Iowa and one of my sessions was recorded, so here’s me sharing my heart in full effect.

Alright, by now you’re thinking, how does this have anything to do with micro vs. macro or staying ready for anything by keeping your stick on the ice?

Well, after this whirlwind of wonderful, the brutal cold season found it’s way into our home. The highs of so much stimulant collided with the lows of isolating sickness. As always, mental fitness was tested. Within the worry of caring for loved ones and the frustration of my own pain, the goodness from days before felt distant. Agitation is hard to fend off during tough times, but with sticks on the ice, we can better embrace the challenge, bend without breaking, and appreciate what makes good times great.

As we give thanks, keep your stick on the ice by recognizing how special each micro-moment is, as they compile into our own macro-moment called life. Happy Thanksgiving!

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.

Winterizing

As temperatures drop, those who live in seasonal climates start preparing for winter. Winterizing your world can mean many things. There are chores to do around the house, gatherings to coordinate, and year-end tasks to finish strong in business. These activities can be uplifting, but the cold that’s coming can also be disheartening.

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My favorite season is the transitional times between each season.

We often resist things we can not change, and this resistance causes suffering. To stay centered, find enjoyment in your changing reality. Celebrate the subtle elegance of winter and remember that all things have a beginning, but also an end. As we accept change, we become more resilient, which invites openness and more enjoyment within the moment. This makes the bitter cold feel refreshing and even in the coldest of winters, an invincible summer will burn from within.

100th

I’ve written into Roasted Reflections every week for almost two years and this is the 100th entry!

I put a lot of thought and energy into every one of these friendly jolts, each brewed to keep you building in different ways. Whether it’s taking the time to read, sharing a quick reply, crafting a caffeinated contribution, or just paying the good vibes forward, I want to thank everyone who starts your Wednesdays with me. As I reflect on this literary journey, here are things I’ve appreciated along with way.

Writing helps us understand ourselves.

– Translating ideas into words is easier the more you do it.

– Verbal dictation can produce a base, then a round of editing brings things together.

– Having a home to organize your writings is more lasting and easier to share anywhere.

– It’s challenging to keep writings concise, but this makes more impact in less time.

– Attention is hard to earn, let alone keep. Stay curious, listen to those you seek to serve, and diversify content creation to stay interesting.

– If you’ve written a book, a complimenting library of shorter entries make it easy to connect ideas back to the book while sharing organized thoughts based on the context of any conversation.

– The thesaurus is a fun tool thats helps us learn new ways to express ideas with fresh vocabulary.

– Publicly publishing your art creates connection.

– I enjoy encouraging others to write.

– Writing is not free. It costs time.

– Without much financial capital involved, the ROI of this type of initiative comes in the form of intellectual, human, cultural, and network capital that churns evolving layers of satisfying value.

– Even so, doubt creeps in. I find myself wondering if I’ll run out of meaningful things to write about every week. Would anyone care if I quit sharing these reflections? If I do decide to quit or reduce the frequency, what’s my why and how might I change the way I ship this art? Would I miss the sense of connection or somehow lose momentum? Perhaps there’s peace knowing the impact can continue being made without weekly additions? I plan to push through these dips as long as I continue to enjoy the challenge, but it can be lonely when we give our best, so please know that I always welcome support from those who have walked this path before.

– Consistency requires sacrifice.

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