Retirement

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.

By Ben McDougal, ago

Hole-In-One

I grew up playing golf, but inadvertently fell out of the game due to work and other priorities. I‘d been longing to get back into the game, but kept procrastinating. So, when my friend Ben asked me to join him for 9 holes to celebrate his 40th birthday at Glen Oaks, I thought… here’s my chance! (LESSON #1: yes = adventure)

At first, I was intimidated and hesitant to have my first round in 8 years be at a fancy country club. I mean, I didn’t even have golf clothes, a glove, or shoes anymore, but I figured this would be a great way to dive in head first and get back out there. So, I quickly went shopping and got a few practice swings in at the driving range. (LESSON #2: now > later)

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This caffeinated contribution was written by Derek Brooks. Derek is a 40.79 year old midwestern American dude who enjoys building, traveling, partying, extremish sports, and can be found in our Roasted Reflections group on Discord.

On Ben’s birthday, I showed up to find him sipping on a Miami Vice cocktail with his buddy and business partner, Sinclair. This immediately set the stage that we were going to have some fun. Golfing with Ben was awesome. Whether it was his general demeanor, his lack of grabbing a scorecard, the way we strolled around the clubhouse, or laughs along the way, this freshly minted 40 year old was a constant reminder that we were here to relax. (LESSON #3: fun > serious)

For the first 5 holes on the back 9, my subconscious nerves were getting in the way. My hits weren’t clean and the strong winds certainly weren’t helping… But despite all the double bogeys, I was still having fun and it felt great being back on the course. (LESSON #4: fun + humility + patience = growth)

Halfway through the round, I could feel the groove coming back. On hole 15, I finally snagged my first par (Ben caught a birdie, haha). After that, we walked up to Hole 16, a 168-yard par 3, with wind in our face. Feeling incredibly relaxed, I lined up with my 7-iron and hit a super clean shot. It felt great and looked even better. The ball dropped just short and left of the pin, took 2 small hops, and then smoothly rolled right into the hole. A freakin hole-in-one. (LESSON #5: openness + growth + serendipity = opportunity)

I couldn’t believe what I’d just seen. Ben and I started screaming and laughing as we ran around the tee box. We full-on bear hugged and I think he even picked me up at one point. Neither of us knew what to do or how to act, so I just threw my gold chain on and giggled while Ben pulled out his GoPro to capture the moment.

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Watch this magical moment!

After that ace, the next hole was a complete blur, but I ended the round with a birdie on 18. If I hadn’t set my nerves/ego aside and took that opportunity to get back into the game by having my first round in 8 years at an intimidating country club, I’d still be in that procrastination loop. I would’ve never gotten my first hole-in-one or shared this incredible experience on Ben’s 40th birthday. (LESSON #6: yes + growth = celebrate)

When I think about this experience through the lens of my career as a technologist, I’m reminded that getting in over-my-head has always been the fastest way for me to grow and move forward. I’m not expecting to be cranking out hole-in-ones from here, but once again, jumping back in head first is something that I will never regret. This memorable day was the reminder I needed to push outside comfort zones, enjoy the moments, and celebrate always.

By Ben McDougal, ago

Eclipsing 40

I sit atop this hill, soaking in the darkness of a total lunar eclipse, verbally dictating this short reflection to celebrate my own 40th trip around the Sun.

As our pale blue dot moved between the moon and our closest star, I first noticed the moving shadow’s blurry edge. As I think about the time we spend on Earth, so much of it is devoted to finding our place in the universe. Even when we are so close to perfect alignment, the blur of subtle distractions will remain constant.

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Perhaps this transitory quest for totality is the impossible pursuit that makes life so much fun.

Anticipation takes over as the final sliver of moonlight goes dark. The orange haze of this blood moon is now the only cloud in the sky. Even with the cool breeze, city lights, distant traffic, and frogs burping, the twinkling stars seem to serenade the silence of this moment. As the darkness holds time still, an eerie peacefulness is accompanied by a welcomed loneliness.

My thoughts soon sync into the shadow of this cosmic darkness. This makes it useless to resist the overwhelming appreciation I have for so many people who have given my life meaning. The past 40 years are a tribute to those who brought me to this place and to the family I’ve chosen every step of the way. Thank you.

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Jodie and Kate, you are the light of my life and my own totality. Together, you set me free to wonder and have taught me the meaning of life. I’m only 40 years old, so while I look forward to much more of our story being written, whenever I do turn my final page, know that I’ll always be with you and wouldn’t have changed a single thing. I appreciate these quiet tears, knowing that my greatest achievement will always be the honor of being part of US forever.

Within the darkness of totality, I’m soon struck by the discomfort I feel, not knowing when the moonlight may return. We’ve all heard how dark it is before the dawn, yet it still feels natural to consider things that have not gone to plan. Accepting past failures, broken relationships, and the future challenges we may face was not an expected emotion, but perspective determines how we respond. I’m thankful that it’s hard to think of anyone who may need to hear this, but if I’ve ever wronged you in anyway, I want to say that I am sorry and only wish the best for you.

As the first sliver of moonlight returns, eminence joy and assuring enthusiasm seemed to rush over my mind and body. It was as if the light of our cherished moon had never been brighter. The subsiding shadow of our planet slowly released moonlight back into the night sky, which lit renewed optimism for all that is still to come.

I am so blessed to have brewed 40 remarkable years into this life. As the full moon shown brighter than ever, so will my appreciation for all that we share.

By Ben McDougal, ago

Serendipitist

Do things always seem to work out for you?

Our internal narratives and external experiences make the cultural consequences of serendipity hard to refute. Serendipity may be pseudoscientific, but it makes sense that things we dedicate our focus and attention to, naturally attracts more of the same.

This mental model can be established in many ways. For me, the appetite for welcoming serendipitous collisions has been brewed from the eternal optimism that an entrepreneurial lifestyle constructs. No matter the source, I believe many of us are, or have the potential to be serendipitists.

Serendipitists seek adventures that invite, sometimes even require different layers of serendipity. The extend at which you control what you’re able to control (a dichotomy within stoicism), while also letting the winds of happenstance guide you through a sense of abundance, determines how often/deeply we experience this charming phenomenon.

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What’s normal for a spider, is chaos for the fly.

In the moment, not everything will work out. This is why serendipitists are often confused with just being lucky. Serendipity and luck both require preparation, openness, and opportunity. The difference between serendipity and luck, is perseverance. Over time, serendipitists share similar energies within their practice.

Serendipitists say “yes” more often.
Serendipitists consistently show up.
Serendipitists assume positive intent.
Serendipitists seek to understand.
Serendipitists are empathetic.
Serendipitists are generous.
Serendipitists stay curious.
Serendipitists fuel positive change.
Serendipitists play long-term games.
Serendipitists have fun and die empty.

As we experience serendipity, celebrate it. Recognize the random awesomeness that comes from the positivity you squeeze into the universe. Continue connecting dots, appreciate how things come together, and keep making a ruckus to feel it even more.

By Ben McDougal, ago

Hybridize

Think back to when you were a kid. Remember that feeling of waking up to a winter wonderland? It’s a snow day! Fresh powder may cause mayhem for some, but all that mattered back then, was how quickly we could get outside to enjoy the day’s frosty gift.

This week we received a few feet of fresh snow. I love the feeling of a blank canvas this provides. I also like to think that one signal for success as an adult, is found in those who have not lost their childhood spirit, so when our little one gets excited about playing in the snow, I make it a priority as well.

After a rushed breakfast, we spent much of the day on a sledding hill. I found myself reflecting on the interactions of this momentary community. The actors are always different people, yet often play the same roles. You have the first-time sledders who are curious, excited, and afraid. In contrast, the action junkies are pushing to always go faster and higher. The adults are on snow patrol, but the personality that I find most interesting, are the hybrids. These are the kids who appreciate the exhilarating activity, but unite others by creating space to ensure newcomers are safe and also having fun. There’s an empathetic maturity in their welcoming enthusiasm.

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The original title was Snow Days.

Fast forward and these hybrids continues to bring things together. We see them in technology, translating nerd to normal, then back from normal to nerd. They are the teachers who inspire our next generation and encouraging children to think differently. Community builders are often hybrids too, as it takes a metaphoric spider to weave, explore, and tighten a collaborative web of actors, factors, and instigators together.

There are many other examples of hybrids connecting dots in almost any environment and they’re all valuable connectors that play important roles. When we think through the lens of complex adaptive systems, hybrids are those who can inclusively identify all that may be possible. They appreciate the entire spectrum of different parts within the system, as well as, the interactions between everything. Almost like chameleons, hybrids have the ability to take different shapes in order to facilitate positive interactions between different perspectives. When this skill is applied through a holistic, positive-sum lens, the effect can be surprisingly wonderful.

For those already hybridizing, thank you, stay curious, and don’t underestimate the limitless value you bring. For those who may not feel such a blended spirit, continue to lead the tribes you trust, but allow intellectual humility to welcome doubt. Such empathy paired with a genuine interest in collaboration, will inevitably unlock fresh ways for those you care about to achieve even more.

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This year-end Tweetstorm was epic and left behind some updates to my website, including a linked library to explore all my Roasted Reflections – https://BenMcDougal.com/Roasted-Reflections

As we reach the end of this wintry ride, I’m grateful for snow days that provide an unexpected chance to slow down. These cozy times provide us a chance to rest and have some fun, while also reflecting on all that’s good. Cheers to these mini moments chilled in our memories, but also to allowing the freeze to melt as we let thoughts pass and stay open to next.

By Ben McDougal, ago