Oversubscribed

It’s a go-go world of busy, busy, busy.

With days scheduled from start to finish, what time is left for random acts of conspicuous kindness, welcoming serendipity, or just saying yes to more adventure?

Thoughtful preparation is often required to coordinate whatever it may be. There’s value in staying organized, but over planning is a trap. The thirst for productivity has made busy look to be successful. How often do we hear pride disguised as disgust, as someone complains about the constrictions of their frantic calendar? Yes, prerequisites include boundless hard work, a healthy obsession, and endless sequencing to be remarkable, but unexpected opportunities emerge when we’re not captive to a calendar.

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Planning is based in fear.

Doing is based in success.

Renting time can be lucrative, but in our connected era, there are ways to efficiently get things done without falling victim to a stacked routine of back-to-back everything.

Meetings led by talking heads, fracturing lunch affairs, and youth sports are all common versions of this trap. Each activity is cool, but when combined, days are booked and every night has something. A few hacks for each include less scheduled meetings throughout the week, but an eagerness to meet anytime. Instead of lunch, meet folks for a brew on either side of the day and consider more adventurous ways to share time. Audibles include parlaying a first meeting with an event, going for a walk and talk, or adding nature into the interaction. This breaks routine and conversations can be more provocative as a shared encounter adds depth to any relationship. Lastly, appreciate limitless play, but organized sports will not define a child’s future. In fact, it more commonly limits the experiences a family enjoys together. The entire game resets at puberty and even at high levels, the idea that sports provide a lasting future is one of society’s biggest fallacies. Organized sports deliver camaraderie, fitness, teamwork, loyalty, problem solving, business opportunities, and a competitive rush, but camps provide these benefits with less time and cost required.

Comfort without a plan leaves space for the unexpected. Things will not always come together, but if the calendar is a tool to keep promises while staying quietly organized, complacency gets replaced with unplanned marvel. If you feel oversubscribed, try flying without a plan. May the voids filled with no agenda unravel a freedom to be your best.

By Ben McDougal, ago

Triangulation

Cross-checking helps determine distance, maneuver around obstacles, and identify missing objects. Alongside the math, a triangulated team diversifies real skills and increases dependability.

With more distinct perspectives, entrepreneurs add synergy that accelerates forward movement and increases confidence when the same problem is attacked from multiple angles. This nimbleness can be leveraged as co-founders also create an invigorating culture that makes each person feel significant. With back-to-back episodes of You Don’t Need This Podcast featuring my two co-founders in FliteBrite, what a wonderful chance to reflect on talented friends who build as one.

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“One’s company, two’s a crowd,
and three’s a party.” -Andy Warhol

If you’re on the prowl for co-founders, consider the value of triangular patterns. Connectors become connected, so show up and be quick to make interesting introductions. Even when the first degree of contact lacks obvious opportunity, remember it’s often the second and third degree of connectivity that delivers more precision. Over time, generosity within an entrepreneurial ecosystem will expand and tighten engaged networks. Instead of forcefully recruiting co-founders, the open-ended activity of a serendipitist will have us colliding with friends we simply haven’t met yet.

When it’s time to build, bonds that formed naturally will support lasting collaboration with people you already respect. That said, established trust is not an excuse to get complacent. From start to finish, be honest and transparent. Every story ends, so invite difficult discussions early and often. Agree on terms, leave space for change, structure the business, maintain an operating agreement to ensure clarity with less tension, and lead by nurturing the power of triangulation.

  • commit to abundant communication
  • invite responsibility, keep the promise
  • remain attentive to details
  • take blame, give credit
  • celebrate in style

Lone wolves can move mountains and rare resources are required with more human capital brewed in, but the expanded capacity and ongoing resilience makes this odyssey worthwhile. When long-term players play long-term games together, the chemical reaction is an affinity toward work that feels like play. Cheers!

By Ben McDougal, ago

Blocked

“How do you write every week for three years?”

Endless community-driven experiences, the privilege of time, building into connecting things I care about, metrics beyond money, publishing YDNTB, staying curious, finding comfort in uncertainty, and an efficiency that comes with consistency helps me continue to articulate written relics I’ll always be proud of.

Writing has become a part of my practice, but it’s not easy and never will be. Life is beautifully busy and what happens when there’s seemingly nothing to write about?

Can I call it writer’s block and hope nobody cares when Roasted Reflections doesn’t land in their inbox on Wednesday? No. Writer’s block is an illusion. An excuse not to ship. This paralysis is a symptom of prioritization within our practice.

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Don’t wait for inspiration.
Let the work inspire you.

Whether you listen to yourself in private (journalling) or share your heart in public, when you know you’re going to get it done, you become more consciously introspective. You stay more in-tune with what needs to be synthesized, while recursion and the indexing effect helps sustain a healthy obsession. Even when the moment’s thesis is not obvious, you’re strong enough to explore what needs to be said. This becomes a habit that invites anyone to reach higher without fearing the generous act of making a ruckus by shipping the art.

By Ben McDougal, ago

Future of Work

Nancy Mwirotsi is a nationally recognized wayfinder who inspired students to lead by outfitting them with skills in technology and innovation. Over the past 10 years, Pi515 has promoted diversity in STEM careers and graduated hundreds of students, with free programs geared toward refugees, young women, and people of color.

The real skills we talk about in this episode of #YDNTP defines the future of work and empower students to thrive through science, technology, engineering, and mathematics. Have fun!

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By Ben McDougal, ago