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.

Airport Foot Massage

I’m not a huge fan of scripted ice breakers, but one that caught my attention, invites people to share something that others in the group may not know about you.

There are many ways to approach such a prompt, but a fun response I once threw in the mix, was my unassuming indulgence of foot massages in airports. There’s something luxurious about having your tired feet rubbed while endless strangers pass by, lol! Along with a very public layer of mental relation, the tightness of your body is basically fixed after a conference, golfcation, snowboarding, or any time you had fun while being away on travel.

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Now that you’re smiling, and also secretly planning to try this next time you fly, follow along to reflect on how we approach our endless transitions.

The thought of “transition” came to mind when a recent airport masseuse was melting my feet into mashed potatoes. The subtle tension of this mini moment arrived as the artisan prepared to switch from one foot to the next. There was an undercurrent of disappointment in that one foot’s rub was coming to end, yet this feeling disappeared when the next foot received its first touch of attention. This is quite a stretch, haha, but this tiny transition made me want to explore these kaleidoscopic moments.

Unconscious transitions are constantly happening all around us, yet some transitions bring forth extra weight or take more time than expected. The path for a smooth transition will be different for every situation, but here’s one tactic to try as you navigate your next transition: Acknowledge the past, then use the present to concentrate energy toward what’s next.

This seems obvious, but such centering can be challenging, as the ego often tries to pull us back to what we may be leaving behind. To surpass these ornery moments, take immediate action toward your forthcoming future.

For example, I think back to when we were first building the Regional Rep role for 1 Million Cups. I remember how hard it was transitioning out of my role as a lead 1MC organizer within the local startup community I care so much about. I had loved organizing 1MC in Des Moines for so many years, and every Wednesday morning felt like a ritual that never got old. As I transitioned into my expanded responsibility, whenever a sense of lose or thoughts of “what if” arose, I took abrupt action. Instead of dwelling on the comfort of what I was stepping away from, I twisted toward my own next. In these moments of uncertainty, I left a sense of lose behind by brewing new connections with more 1MC organizers I was excited to support/connect in the new Regional Rep role. This progressive action helped build relationships and a lot of constructive momentum. Over time, what first felt transitional, soon became my practice. This clarified my new role while also providing space to evolve for the new 1MC organizing team in Des Moines.

Wow. That was over four years ago! I’ll always be a 1MC organizer in Des Moines, but that progressive action helped me move forward and released personal bandwidth needed to help build my new role with the Kauffman Foundation. Fast forward to now. I’m still an active 1MC attendee here in Iowa, but I’m also blessed to collaborate with hundreds of remarkable community builders, ecosystem builders, and 1MC organizers throughout all 12 states that make up @1MCMidwest. Even more, after years of complex work with 1MCHQ and the other four Regional Reps, #1MCNation is now more aligned and supported within it’s connected era. As with most ventures, there will always be more to do and everything will continue to evolve, but it’s such a gift knowing so many lifelong friends are enjoying coffee every Wednesday morning, in over a hundred 1MC communities nationwide.

Hopefully the lighthearted ice breaker, followed by that oddly connected reflection, inspires you to stay energized as you grow from within your next transition.

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To celebrate Valentine’s Day, here’s a telepathic gift. Think back to when you enjoyed a relaxing massage, yoga, workout, or meditation. Alright, in that peaceful state of mind, close your eyes and enjoy five deep breaths. Ahhh…alright, get back to building.

Anticipation

The present is a gift, but it often feels like a window that reflects past experiences into what may come next.

The temporary nature of each moment makes it hard to hold onto. For those who like to build, it can feel lazy if we’re not constantly evolving from things we’ve learned in the past while also actively planning for the future. While staying in the moment provides peace and limitless space to appreciate the entire spectrum of now, mashing this mindfulness with an ability to explore and create fresh things is healthy and often creates the common sense of anticipation.

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This was written on a plane, right before I recorded Landing in Salt Lake City, followed by two days snowboarding in Park City, and then my first time having coffee with 1MC Salt Lake City.

Sometimes anticipation can be confused with worrying too much, but it’s quite different. Worrying is like agreeing to be unhappy until the present delivers whatever originally concerned you. These two feelings do have one key attribute in common: they are both focused on the future. This is one reason why anticipation flies in a similar orbit with worrying. In contrast though, a key difference that anticipation has going for it, is how it often has a more positive spin.

The positive nature of anticipation can be a signal of purpose and progress. It emerges all around us. It might be that new startup your building toward launch. A first date, booking travel, having a baby, the first day of school, or basically the first time trying anything new delivers different levels of this same sensation.

Another positive effect of anticipation, is how it can help guide proper planning. Creating moments in a business that allow the team to feel anticipation can fuel purpose and over time, this converts into a shared conviction. This leads to the potential to unlock a wonderful wild card: persistent. In business and in life, a strategic effort up front, without overdoing it or getting caught up in things you can’t control, may allow the anticipation of a future moment to soon land exactly the way it was meant to be.

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After whatever created the initial anticipation, it  sure feels great when a small amount of planning is paired with an open mindset and everything turns out just right.

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.

Open to Next

Setting goals and honest resolutions provide a useful purview into what’s next. It’s no secret that appreciating the past and planning for the future can provide a fresh boost during transition times. As this introspective activity warms your thoughts and emotions, joy awaits those who translate such enthusiasm into heartfelt energy that fuels sustained action.

As we look forward, dare to be different by also staying open to things not in the plan. This fluidity helps us avoid the limiting effect of being too rigid.

There are times to remain stringent in order to stay on course, but embracing the plot twists of life ensures that perseverance does not become misguided. Most people like the idea of being a free spirit, but openness can be fleeting, because we find solace by way of control. Think about the last big trip you planned. You locked in travel, accommodations, and maybe even a collection of planned activities. You basically craft a scripted adventure to experience for yourself. If all goes to plan, you’ll surely enjoy the trip, but how often does everything go exactly to plan? Almost never, yet the unexpected detours often lead to the best stories.

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Higher the contrast, better the story.

Openness laced through different types of short and long-term goals, activated by habits that churn goals into surpassing accomplishment, provides clarifying direction with space left over to welcome serendipity. Letting go to stay open can become a source of anxiety, but the unknown can be an exciting place where possibility allows us to discover what’s next.