Mental Modeling

Maverick

“I don’t like that look…”
“It’s the only one I got.”

Entrepreneurs enjoy the ride on our highways to the danger zone. There’s a comfort in uncomfortable and the edge is where’s it at. Skills and tactics can be learned, but steady action, confidence, humility, and long-term persistence are just a few things required to embrace entrepreneurship as what it needs to be: a lifestyle.

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Everyone has a creative spirit. When an appetite for (calculated) risk is applied, the entrepreneurial spirit is unlocked. This can be nurtured by community and work that feels like play. This grows the entrepreneurial spirit until it becomes a way of life.

When building becomes a part of who you are, the result is not authenticity, it’s consistency. As open-mindedness and generosity lathers into long-term consistency, trust bubbles. Trusted community members who then invest toward understanding those they serve, will almost always find some form of success. This might be the side hustle they love talking about, the innovative role they build as a linchpin inside an existing organization, or that first hire that grows into a whole new business.

As Top Gun: Maverick reminds us, it takes commitment to feel your way through this mission. Don’t think. Make entrepreneurship a lifestyle to keep learning, building, and having fun on your way past hypersonic.

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“Talk to me, Goose.” —Maverick

By Ben McDougal, ago

Hole-In-One

I grew up playing golf, but inadvertently fell out of the game due to work and other priorities. I‘d been longing to get back into the game, but kept procrastinating. So, when my friend Ben asked me to join him for 9 holes to celebrate his 40th birthday at Glen Oaks, I thought… here’s my chance! (LESSON #1: yes = adventure)

At first, I was intimidated and hesitant to have my first round in 8 years be at a fancy country club. I mean, I didn’t even have golf clothes, a glove, or shoes anymore, but I figured this would be a great way to dive in head first and get back out there. So, I quickly went shopping and got a few practice swings in at the driving range. (LESSON #2: now > later)

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This caffeinated contribution was written by Derek Brooks. Derek is a 40.79 year old midwestern American dude who enjoys building, traveling, partying, extremish sports, and can be found in our Roasted Reflections group on Discord.

On Ben’s birthday, I showed up to find him sipping on a Miami Vice cocktail with his buddy and business partner, Sinclair. This immediately set the stage that we were going to have some fun. Golfing with Ben was awesome. Whether it was his general demeanor, his lack of grabbing a scorecard, the way we strolled around the clubhouse, or laughs along the way, this freshly minted 40 year old was a constant reminder that we were here to relax. (LESSON #3: fun > serious)

For the first 5 holes on the back 9, my subconscious nerves were getting in the way. My hits weren’t clean and the strong winds certainly weren’t helping… But despite all the double bogeys, I was still having fun and it felt great being back on the course. (LESSON #4: fun + humility + patience = growth)

Halfway through the round, I could feel the groove coming back. On hole 15, I finally snagged my first par (Ben caught a birdie, haha). After that, we walked up to Hole 16, a 168-yard par 3, with wind in our face. Feeling incredibly relaxed, I lined up with my 7-iron and hit a super clean shot. It felt great and looked even better. The ball dropped just short and left of the pin, took 2 small hops, and then smoothly rolled right into the hole. A freakin hole-in-one. (LESSON #5: openness + growth + serendipity = opportunity)

I couldn’t believe what I’d just seen. Ben and I started screaming and laughing as we ran around the tee box. We full-on bear hugged and I think he even picked me up at one point. Neither of us knew what to do or how to act, so I just threw my gold chain on and giggled while Ben pulled out his GoPro to capture the moment.

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Watch this magical moment!

After that ace, the next hole was a complete blur, but I ended the round with a birdie on 18. If I hadn’t set my nerves/ego aside and took that opportunity to get back into the game by having my first round in 8 years at an intimidating country club, I’d still be in that procrastination loop. I would’ve never gotten my first hole-in-one or shared this incredible experience on Ben’s 40th birthday. (LESSON #6: yes + growth = celebrate)

When I think about this experience through the lens of my career as a technologist, I’m reminded that getting in over-my-head has always been the fastest way for me to grow and move forward. I’m not expecting to be cranking out hole-in-ones from here, but once again, jumping back in head first is something that I will never regret. This memorable day was the reminder I needed to push outside comfort zones, enjoy the moments, and celebrate always.

By Ben McDougal, ago

Anxiety

Our mind is divine. It gives everyone super powers and the dots we electrochemically connect makes us human. Such biological capacity allows us to achieve extraordinary things. At the same time, this mysterious grey matter can also hold us back, even cause havoc.

Anxiety is assuming failure in advance. As a mental cousin to fear, anticipation, worrying, and perhaps even desire, anxiety is like an unspoken agreement you make with yourself to be unhappy until you get what you want. While some may argue that this exhausting emotion is all in your head, the way anxiety effects your body can be absolutely real.

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“With great power comes great responsibility.” -Uncle Ben, Spider-Man

The connected era has made the world smarter, stronger, and more efficient, but the pressure of never-ending progress leaves us vulnerable to fear and anxiety. For those who pursue greatness (which I might suggest is anyone reading this), the more we try to achieve, the tighter we wind the strings of life. When harnessed, this creates strength, artistry, grit, and persistence. As the tension tightens however, there’s bound to be a break. Being mindful of your personal bandwidth will help reduce the frequency and severity of such breakdowns, but it seems impossible to completely avoid anxiety.

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Accepting that anxiety is inevitable, may be a secret to finding equanimity.

The most common way we attempt to manage such angst, is to stop the pain by seeking reassurance. The nourishment of overthinking every scenario in an unknown future may satisfy  the moment, but scratching this itch usually makes things worse. Even if we answer every possible question, the willingness to indulge the worry sets a precedent that keeps you coming back to what can become an endless loop.

It’s much harder, but an alternate approach is to acknowledge the suffering. Don’t run from it. Appreciate the relentless internal narrative you’re dealing with. Breathe. Be thankful for having something you care this much about. Find peace knowing you’ve done your best to tip odds in your favor, but invite doubt and welcome an opportunity to be wrong. The anxiety is here and it’s dramatic, but it’s also normal. Let thoughts float by, focus your attention on what’s good, and allow time to heal the pain. Yes, this is like letting a forest fire burn without soothing it with water. It will get wild at first, but eventually burn itself out. The scorched land is then ripe for renewal and less likely to burn again. When we acknowledge anxiety this way, the resulting clarity provides an awareness that helps us understand this energy. Our courage also helps to break the cycle and over time, often reduces the frequency of such misery.

The ability to appreciate anxiety, an eagerness to lean on those who support you, and confidence in knowing the temporary pain will pass, allows the mind to need less dramatic swings to stay centered.

By Ben McDougal, ago

Listen

Listening is louder than it sounds.

Most entrepreneurs like to talk and the more obsessed we are, the more vociferous we seem to get. Idea machines must be willing to share compelling stories, but listening is a key part of any transmission. This may seem obvious, but with precious air time up for grabs and knowing so much about our own interests, listening can devolve into feeling like a required distraction.

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Hearing is passive. Listening is active.

As we guide people through the layers of understanding, active listening forms a bond much faster than forcing yourself to be heard. The fear of not having time to deliver your message will linger, but when we truly tune into what another person is saying, it shows we care. It also helps us better harmonize our thoughts within the moment and counters the common mistake of overloading others with too much numbing details all at once. Knowing each conversation is part of a broader relationship and community-building journey, good listeners are almost always given a chance to make a bigger impact.

Ready for an experiment? The next time you meet someone new, embrace your inner scientist. Set your introverted/extroverted mindset aside and focus your attention on asking as many thoughtful questions as you can. The less you talk, the better. This will feel awkward if you just fire question after question, so be concise with each response, then return to more thoughtful questions for a more natural interaction. Consider expanding this social experiment by purposely doing this throughout an entire networking event. Remember who you talked with and track how the listening-focused conversations evolve. Over time, how do these relationships built on listening, compare to others where you’ve been more outspoken? Here are a few tactics to support your practice.

  • Center your internal attention.
  • Stay engaged with eye contact.
  • Use jarring questions to dodge small talk.
  • Don’t interrupt or jump to conclusions.
  • Occasionally paraphrase what was said.
  • Avoid the urge to make it about you.
  • Ask curious questions to go deeper.
  • Exit gracefully, without a sense of rush.

This type of active listening will extend your ability to hear more, but also make your responses more in-tune with what others are thinking, versus always trying to prove your point. Selflessness may keep a conversation from landing exactly where you want in that moment, but as you move from one topic to the next, you’ll learn how others work. When done well, an unspoken bond forms. This synchronization creates space to explore more directions you’d like to take future conversations, but now with the priceless ingredient of shared enthusiasm.

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Listening within a support network ignites optimism, connection, and motivation. A healthy balance is to also listen to your challenge network, which keeps us intellectually humble and rooted in reality.

By Ben McDougal, ago

Linchpin

We are often told being extraordinary makes us special. We each write our own story in life, but as Neil deGrasse Tyson suggests, perhaps the sameness of our cosmic composition is what makes each of us fundamentally special from start to finish? This eliminates the need for permission and invites us all to be remarkable.

Our connected era has evolved society away from the industrial age. The factory (existing organizations that have an established system in place) and replaceable cogs that follow instructions to keep the vast machine churning has faded in favor of those who unite tribes, are champions of change, and willing to make a ruckus. Back in 2010, Seth Godin gave those who choose to be indispensable a name: Linchpins.

Linchpins are artists who consciously care enough to go beyond mediocre. Linchpins solve interesting problems and make judgement calls without a map. They welcome weird. They are scientists who stay curious. They are generous and passionate about the art of connection. Through an inclusive, positive-sum lens, linchpins lead and let others lead without seeking credit. They are fearless, in that they are unafraid of things they don’t need to be afraid of. Linchpins leave resumes behind with work that transcends time as they build at speed of trust and relentlessly #givefirst, knowing that accelerating others generates unmatched energy.

The skills of a linchpin are hard to quantify with tradition metrics, but a willingness to bring your true genius to work is an open invitation for us all. Over time, the linchpin’s art often becomes meaningful to many, which makes work less about trading time for money. In this centered state of career nirvana, nobody can compete with being you. Cogs in a machine are replaceable and can therefore be paid less. When you are a linchpin, you have leverage and there is no option but to reward you for work that is a creative expression rooted in lasting purpose.

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“Leaders don’t get a map or a set of rules. Living life without a map requires a different attitude. It requires you to be a linchpin.” -Seth Godin

If indispensability is so accessible, why doesn’t everyone accept the invitation to be a linchpin?

One primal reason is the indoctrination of an education system that was designed to produce factory workers. From an early age, we are brainwashed to pursue perfection, to color in the lines, to follow instructions, to care what others think, and to define success by worldly consumption. Educational transformations are all around us and great teachers willing to be linchpins are activating students to go beyond the system. Instead of molding obedient factory workers who’s only hoping to be taken care of by factories built on promises of the past, we can teach people to take initiative. To invite doubt. To passionately explore one’s superpowers. To solve interesting problems while leading us with reverse charisma and confident humility.

Another reason why some stay complaisant, is the outdated promise of an American Dream. Gone are the days of clocking in on time and keeping your head down just long enough to climb a ladder built to resist change. The factory worker’s willingness to play it safe may extend a sense of temporary security, but this is a choice that makes you easy to replace with cheaper labor, faster tools, and advancing technology. Whether it’s fueling innovative action as an intrapreneur at an organization that prefers linchpins over factory workers, diversifying your career portfolio with an inventive side hustle, or building pain-killing projects as an entrepreneur, we may only live once and life is too short not to enjoy your work.

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What makes you indispensable?

By Ben McDougal, ago