Mindset

Tinker

This is your invitation to tinker.

The Headline Trap is real, life can feel busy, and we all have existing responsibilities, but take a moment to hold your arm as high as you can. Go ahead, I’ll wait…

Extra Shot
Need fresh ideas?
Try this daily exercise.

…ok, now…hold your arm higher! I bet you found room to push further, eh? This is a fun reminder that we all have more to give. Tinkering requires initiative, but we all have extra gears to help us avoid feeling like we left something on the table. Yes, comfortable feels safe and easy is easy, but why not turn a few knobs to see your idea twinkle?

When we accept an invitation to tinker, financial capital can speed things up, but time is usually the primary capital required. It’s amazing how much happens by showing up and activating a few early moves. While more of everything will be needed to commercialize an idea, thinking about this exploration through an adaptive lens of seasonality also reduces the weight of side hustles.

If you’re having a hard time finding inspiration, force yourself into environments were others are tinkering too. Community events within an entrepreneurial ecosystem can provide energizing human, intellectual, and network capital, but classrooms, makerspaces, hackathons, and coworking spaces are where people are tinkering together.

Whether it’s at home or in the community, tinkering celebrates pure wonder and will nourish your innovative spirit. Even if the answer is “no”, at least you’ll know.

Extra Shot
Things you dedicate time to will grow.

By Ben McDougal, ago

Gimmies

Gimmies are illegal under the Rules of Golf.

So why is the gimmie so common on the golf course? Does picking up your golf ball without tapping that “unmissable” putt really save much time? What’s the harm in a clean finish? Isn’t it worth hearing the satisfying sound of your golf ball dropping into the cup?

If you’re like me, most gimmies are not unmissable. Here lies the truth. People give gimmies so they will be given a break on short putts they might miss. There’s nothing wrong with keeping things casual, but tacit assumptions leave room for misunderstandings.

Extra Shot

May your feet always stay in the fairway.

If we golf together, you know I’m 100% chill. I’ve learned golf is like a walk in the park with a small objective, but if you’re keeping score, see how it feels to not give or take gimmies. Appreciate the short putts you miss. Count those extra strokes, knowing an unequivocal finish feels good and builds confidence for when gifts aren’t up for grabs.

By Ben McDougal, ago

Not to Lose

I’ve been around soccer the majority of my life.

Whether it was traveling with the college team my dad coached as a kid, playing club soccer at an early age, focusing on the sport in high school, playing all through college, or being the product of my first entrepreneurial venture, soccer was a part of my identity for over 20 years. This team sport helped me push to be my best, but the sense of belonging is what made it special.

As I’ve enjoyed the World Cup in Qatar, I’m reminded how easy it can be to get ahead in a match, before slipping into a dangerous trap. Instead of staying sharp by maintaining the offensive pressure that earned an early lead, it’s tempting to start playing not to lose.

In soccer, this often means a team sinks back into an overly defensive formation. Less variety invites frantic desperation and the added pressure often leads to an equalizing goal being scored by the opposing squad. Even if the need for another goal shifts your team back into a more balanced attack, the momentum has shifted.

When applied to business, getting ahead and then playing not to lose can be seen all over the map. For instance, snagging a few early adopters, then assuming customer discovery is over. Hiring new talent, then hoping everyone can work together without initiative. Launching a new product with existing customers, then not supporting them through the chasm of change. Securing product-market fit, then avoiding innovation due to a misguided sense of risk. Finding generous mentors, then forgetting to nurture relationships. Those are just a few, but many leaders are lulled into this trap that’s defined by a sense of scarcity.

Tactics to stay ahead differ based on situational factors, but when in doubt, trust that uncertainty is certain. Be strategic to avoid recklessness, then stay on the offensive by leaning into the pain. As you find fresh ways to serve customers, continue celebrating milestones and stay ahead with initiative to keep building beyond the fear of losing.

By Ben McDougal, ago

Intrinsic

We all have bad days. When they string together, the stress gets heavy. This mental weight becomes especially unwieldy when the cause is unclear. After a couple down days, I went searching for the origin of my cloudy mood.

Along with insight on entrepreneurship, venture capital, and community building, Brad Feld talks a lot about mental fitness. The entrepreneurial lifestyle is a lonely roller coaster and I’m thankful for leaders like Brad (and many others), who have helped destigmatize the complex circuitry between leadership and mental health.

I found this entrepreneurship & mental health series from Techstars helpful, then wove in this 2015 interview to translate my temporary despair. Brad talked about how he’s gone through serious bouts with depression and through those challenging times, he’s been able to identify one of his intrinsic motivations to be perpetual learning. He went on to describe how even when he was busy and perceived to be successful, if boredom began to set in, an isolating absent of joy may soon follow.

This gave me clarity. I realized that one layer of my own intrinsic motivation is also learning. I like being in situations where I’m exposed to new things, thinking about fresh ideas, solving interesting problems, hearing stories from different people, and building into things I really care about. When there’s a lull in the action, it’s easy to think the ride is over. While this thought is misguided and untrue, it’s still disheartening. Mental fitness means something different for everyone, but here are a few exercises I plan to maintain within my practice.

  • Link learning with teaching.
  • Recognize that the storm will pass.
  • Find trusted peers to release tension.
  • Use this stimuli of stress to focus.

Adam Grant reminds us that strength does not come from ignoring pain. It stems from knowing that your past self has hurt and your future self will heal. Within the crucible of entrepreneurship, hardship is inevitable. Radical self inquiry keeps leaders aware of their mental fortitude. Such awareness then helps us maintain and uncover new stepping stones that illuminate our own path to thrive beyond momentary setbacks.

Extra Shot

Calm is one of my favorite apps. The guided meditations and sleep stories are a healthy aspect of my daily routine. Here are 10 ways to boost your mental fitness, a mental fitness training guide, and free mindfulness resources from these focused friends.

By Ben McDougal, ago

Exploring Education

Educational organizations are key actors within entrepreneurial ecosystems. As a community builder, collaborating with students and leaders within educational organizations has been enlightening.

While I’ve always enjoyed exploring the intersections between entrepreneurship, innovation and education, it feels like I’ve been thinking and talking about the future education a lot more lately.

Perhaps it’s my Regional Rep role for an educational program like 1 Million Cups? Maybe it’s how many caffeinated community builders I’m supporting, who also work in this space? Blunt thought provocations from Naval Ravikant keep me on the edge of my seat and having a daughter who’s about to experience the classroom for the first time has to play into my heighten curiosity as well. It’s clear that my interest in education does not emerge from a single source. It’s the collective interactions. It’s my interest in accelerating others. It’s wanting the best for my little startup that pays in love. Even deeper, it’s an optimistic enthusiasm for our future.

Extra Shot

I’m envious of students who are being encouraged to explore their entrepreneurial spirit so much earlier. I only regret two things from my experience in college: not starting a business and not understanding the value of an engaged network.

Our connected era and the rising cost of higher education seems to be signalling a cultural shift. It’s less about earning a piece of paper so you can work for someone else. The future of education feels more like providing a safe space to explore knowledge, social interactions and what creative activities feel like play to you, but look like work to others.

We learn, earn and then give back. My hope is that we can inspire future generations to go beyond what we think is possible. Can we leave behind parts of the system that feel like day care and replace them with curricula that reward pure wonder, initiative and skills that help more people evolve ideas into reality? Outside the classroom, can we celebrate life-long learning and those who break down barriers so more people are set free to push past the status quo?

As Greg Horowitt said in our conversational jazz, without order nothing can exist, but without chaos, nothing can evolve. Let’s build for the sake of our future, by never fearing unicorns in our balloon factories.

By Ben McDougal, ago