Family

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.

By Ben McDougal, ago

Feng Shui

Welcoming the unpredictable forces of life, provides ease and creates space for energizing adaptation. Peace awaits those who appreciate all that is, without worrying so much about all that is not. That said, we know this doesn’t mean everything just falls into place. It takes initiative, consistency, awareness, and sacrifice to find your own version of equanimity.

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It’s not a rainy day. It’s free water.

As I felt the warm wind of this sunset cruise on a glass lake, Kid Cudi mentioned feng shui and got me thinking about this week’s writing. Similar to how one may setup the space of a home to harmonize with nature, we can connect elements of our own career portfolio to feel the universal benefits of feng shui.

The places you visit, the people you’re with, and the art you generously create all connect through you. Over a lifetime, you become an environment for others, and this becomes your legacy. If there’s passion, diversity, intellectual humility, and overall harmony within your environment, your impact on the universe can be serendipitous and my hope is that the way you spend your time, will add up in the end.

By Ben McDougal, ago

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?

By Ben McDougal, ago

Milestones

Big or small, internal or external, milestones help people identify with progress. They draw lines in the sand. This clarifies goals while supporting short-term accountability and long-term motivation.

Entrepreneurship is a community sport, but creative problem-solvers working to build a business are still competitive. Milestones tap into this competitive spirit by gamifying a performance-based culture. Recognizing milestone achievements can also boost morale and further unite a team. If you’re collaborating with mentors and/or an advisory team, milestones help keep everyone on the same page as well.

As milestones are established, be sensitive to the diversity of your team. Find creative ways to equitably encourage new and more experienced team members. One easy way to do this, is to establish a few tiered categories for different types of milestones. As you diversify milestones, we’re not creating so many that they become pointless. Instead, you’re curating a variety of dynamic signals that can activate different emotions along a connected and sustained timeline.

As milestones are completed, the culture is nourished with celebration, which we’ll sip on next week!

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