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.

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.

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.

Die Empty

Graveyards are full of good intentions, untold ideas, disconnections, and missed opportunities.

As we celebrate year-end holidays and look to 2022, it’s easy to make audacious plans for what’s next, but perhaps it’s wise to pair big ideas with small actions?

This obviously means something different for everyone. For example, there are times in our lives when we seek to do so much more. It’s easy to feel overwhelmed when cool ideas, good intentions, and even positive action doesn’t lead to the anticipated outcome. For those who face this mental mountain, first give yourself grace by remembering that we either succeed or learn. This will help you find closure with past failure(s). As you push through this self-limiting mindset, lean back into your community of fellow founders. It’s even harder to show up when you’re experiencing a dip, but movement activates motivation and leaning into the prosperity of others will percolate helpful conversations. Pair this curiosity with a pinch of vulnerability and you’ll be reminded how generosity builds trust and helps you solve new problems.

In contrast, there are other times when a profound sense of accomplishment leaves us wondering what more can be done? This would seemingly be a privileged state, but our sense of purpose can waver when goals have been met. This can cause even the most ambitious spirit to feel lazy. A sense of achievement dysmorphia can also set in, which downplays our accomplishments in an effort to create space for more. Perhaps one way to counter this type of mental moment is to pair celebration with relaxation, creativity, and humility. Rejuvenation often emerges from self-care rooted in gratitude. This form of vulnerability brings peace, which often provides clarity on prolific ways to make a deeper impact on familiar fronts, or energy to explore brand new ways to fuel positive change.

The nudge you need will be dynamic based on the complexity of your ever-shifting environment, but a willingness to persist allows us all to keep building.

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The YDNTB audiobook was just released and listeners love it! It is now available as a direct download (with bonus features) in this special Holiday Bundle. It can also be found on Audible, iTunes, and Amazon.

It’s impossible to measure the amount of time and effort it took to narrate, edit, and professionally publish this 5-hour audiobook (here’s how I did it), but that’s not what matters. What matters is that I have a remarkable relic to be proud of forever. Enjoy the show my friends!

Along with what you’re able to undertake, appreciate all that you cannot. When idea machines have an opportunity surplus, it’s easy to over commit. It’s much harder to stay cognizant of our personal bandwidth when our connected era is always introducing new ways to spend your time. These are crossroads where you’re invited to be honest about your own purpose, by allowing the superpowers of others to activate something you can/should not. As you share the love, deliver ideas, resources, connections, and opportunities without hidden agendas. You can’t take such things with you, so boldly give them away with a sense of abundance and find renewing joy in helping others bring more good things to life.

My hope is that after reading this year-end reflection, you observe the blunt title less around loneliness, and more as positive encouragement for doing all that we can with our precious time in this life.

A sustainable cadence leads to longevity, but a profound legacy awaits those who exhaust all their love, intelligence, connectivity, and energy to leave satisfied in the end.

Slow & Fast

Slow is smooth, and smooth is fast.” -Kerty Levy

This tweetable thought randomly emerged over coffee today. It’s interesting how philosophies on life, wealth, and happiness evolve from entrepreneurial endeavors.

Perhaps it’s the personal nature of building your own business that causes such reflections? It might be the transformative skill of verbalizing your thoughts and ideas with others? Maybe it’s less about business and more like a beautiful side effect of mindfully aging?

The reason(s) and frequency at which you allow yourself to explore big ideas surely depends on the environment, people you interact with, and knowledge you pursue.

This makes me thankful for my own entrepreneurial experiences, but more important, the immeasurable blessing it can be to expand our minds by plugging into startup communities and entrepreneurial ecosystems. A willingness to show up and the trust built through such generosity has allowed me to become apart of so many other founder stories. As I mention throughout YDNTB, consistent action over the long run is required, but the remarkable insight we pick up along the way can provide a path toward true understanding for anyone, on almost any front. As we support entrepreneurs through the art of connection, the invitation to have more diverse discussions is unlocked more often. Whether it’s strategic, tactical or philosophical, what a gift this can become.

Along with stimulating conversations with agreeable people in a support network, it’s important to weave in perspectives from a challenge network. This is a group of disagreeable people we trust to point out blind spots, which helps us overcome our weaknesses with critical feedback we may not want, but need. Curious interactions within a challenge network also unlocks humbling opportunities to be wrong. This helps us avoid misguided confidence through intellectual humility, and brings us closer to the truth.

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Smart people change their mind all the time. Find joy in discovering you were wrong. You’re now less wrong than before, and when we admit it, we’re not less competent, we’re being honest and displaying a willingness to learn.