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.

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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Training Wheels

When training wheels come off a child’s bike, it’s a breakthrough moment.

Learning to ride a bicycle was not as easy as it looked. The early excitement of that new bike was bolstered by the comfort of training wheels. These little stabilizers provided balance, but eventually became self-limiting. Whether you remember learning to ride a bike or have helped a little one figure it out, the urge to remove such limitation forms fast.

Removing training wheels only takes a minute, but then fear sets in. The challenge of staying upright, maintaining speed, avoiding obstacles, and falling without getting hurt feels overwhelming. Even with the support of others, success seems out of reach, until it clicks. Like magic, trepidation transforms into gliding independence.

Moving beyond the comfort zone that training wheels provide children, reminders us how wonderful it feels to overcome hardships. Considering how easy it can be to leave training wheels on too long, also awakens thoughts of how contentment can lead to complacency.

Being content without becoming complacent is a constant test. One moment you’re grateful for all that is, then soon you’re wondering why you feel oddly stuck. Perhaps this is because the more complacent we become, the more rigid we get. This rigidity often devolves into a stronger fear of change. When the movement that comes with change becomes associated with risk, it’s common to feel stuck, stagnant, or even irrelevant.

If training wheels are holding you back, initiative can set you free and persistence will keep you moving. When movement is gratifying, even when it’s hard, you’re set free to keep shifting gears as you ride toward what’s next.

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It was energizing to see so many friends at #TSDemoDay! This was a community celebration and milestone moment for entrepreneurs pushing beyond their own comfort zones, as this 2022 class emerged from the Techstars experience.

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.

Winding Whys

Asking “why” seems to be innate.

As soon as kids learn to speak, the inquisitions begin. The first few whys may emerge from innocent curiosity, but it’s easy to tell when the game is underway.

It’s easy to see how endless whys may lead to frustration (especially when it’s bed time, eh), but I’ve found joy in making these winding whys into a fun challenge for myself. Instead of shutting things down, I enjoy trying to quickly answer every why with an accurate answer. Can I mindfully outlast the youngster’s attention span? What fun!

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I’ve enjoyed winding whys many times, but “Dad, why do you love me?” gave me pause. I found myself feeling appreciative as I tried to coalesce endless reasons into one answer.

As I poked around, it felt trite to reflect on how humans have so many whys we can not answer. Instead of going down the paradoxical path or leaning into understanding our own whys, I found the Five whys interesting.

Developed by system thinkers inside Toyota back in the 1980’s, this iterative Five whys technique was used to explore the cause-and-effect relationships underlying a particular problem. When following 14 specific rules, after exactly five whys, the last answer often points to a process that is not working well or does not exist. This rigid technique has critics and would seemingly lead to shortsighted interpretations, but it was fun learning about this historic use of why. Knowing the value of complexity vs. simplification, as well as, so many other methods like active listening, Socratic questioning, casual diagrams, storytelling, inverse charisma, and pure wonder, the Five whys may not answer all the winding whys of our world, but perhaps it’s another tactic to throw in the mix.

Why not?