Winding Whys

Asking “why” seems to be innate.

As soon as kids learn to speak, the inquisitions begin. The first few whys may emerge from innocent curiosity, but it’s easy to tell when the game is underway.

Endless whys may lead to frustration (especially when it’s bedtime, eh), but why not find joy in making these winding whys into a fun challenge. Instead of shutting things down, try to quickly answer every why. Can we mindfully outlast a youngster’s attention span?

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“Mom… Dad… why do you love me?”
After countless rounds of winding whys, what a fun chance to coalesce endless reasons into one run-on sentence.

As we zoom out, it feels trite to reflect on how humans have so many whys we cannot answer. Instead of the paradoxical path or trying to understand all of our own whys, the five whys from Toyota is an interesting tactic.

Developed by system thinkers inside Toyota back in the 1980s, this iterative technique was used to explore the cause-and-effect relationships underlying a particular problem. When following 14 specific rules after exactly five whys, the last answer often points to a process that is not working well or does not exist. This technique has critics and can lead to rigid, even shortsighted interpretations. That may be the case, but more often than not, our own willingness to go deeper helps move past easy answers.

The five whys may not solve all our winding whys, but the idea behind this historic tactic can be fun to use at home. We also know playing with why is helpful for decision making and culture building in business.

As winding whys carve through your mind, appreciate the difference between complex, complicated, and simple ideas. Socratic questioning, active listening, real-time doodles, media-supported storytelling, inverse charisma, laughing, and of course, child-like wanderlust all add a twist. Why not?

Brewed From Within
#119 📖 Life & Happiness

By Ben McDougal, ago

Hole-In-One

I hadn’t touched a golf club in eight years, until Ben invited me to 9 holes to celebrate his 40th birthday.

LESSON #1: yes = adventure

After being away from a game I once loved, the first round back was intimidating, but why not? I picked up some golf gear and hit a driving range.

LESSON #2: now > later

When the day came, I arrived to find my friend sipping a Miami Vice with his good buddy and business partner. This set the scene. Whether it was strolling around the clubhouse or our carefree laughter along the way, it was clear we were here to have a good time.

LESSON #3: fun > serious

Even with a relaxing vibe, my nerves got the best of me the first 5 holes. My shots were timid, and the wind wasn’t helping. Despite the double bogeys, I was having fun and it felt good being back on the golf course.

LESSON #4: humility + patience + fun = growth

Halfway through, a groove was returning. On Hole 15, Ben caught a birdie and I hit my first par. We then rolled up to Hole 16 at Glen Oaks Country Club, a 168-yard par 3. Feeling relaxed, I grabbed my 7-iron and hit a clean tee shot. It felt great and looked even better. The ball dropped on that freshly aerated green, just short and left of the pin. It took two small hops, then silently rolled into the cup. A freakin’ hole-in-one!

LESSON #5: growth + openness = opportunity

We started dancing in disbelief. Neither of us knew what to do. I threw on my giant fake gold chain and giggled while Ben captured the moment. The rest of our day was a blur, and we’ve continued to celebrate ever since. Without this yes to adventure, I never would have gotten my first hole-in-one or shared this epic experience on my fun friend’s 40th birthday.

LESSON #6: growth + opportunity = celebrate

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This contribution is from Derek Brooks, a Midwestern American software engineer who enjoys thinking, building, fixing, traveling, camping, rocking, and once again, golfing.

As I appreciate these life lessons through the lens of my career as a technologist, I’m reminded that getting in over my head has been the fastest way to grow and move forward. When we push outside comfort zones and always celebrate in style, we have fewer regerts.

Brewed From Within
#111 📖 Life & Happiness

By Ben McDougal, ago

Slow & Fast

Slow is smooth, and smooth is fast. This sounds like a contranym, but when we slow down, it’s easier to find a rhythm that activates kinematics to add elegant speed.

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Accuracy sparkles within rhythm.

This concept serves founders who are building with a turbulent sense of urgency. For example, startup life in an accelerator is a compressed environment for ideas to flourish. When mentors and investors are dedicated to helping founders succeed, milestones will be achieved, but growing too fast can leave the team feeling hollow.

With decisions at every turn, relationships still take time. Early hires are delicate. Financial modeling is complicated. Sometimes the product isn’t even fully baked. This is when slowness adds a healthy thickness. Patience leads to deeper understanding, which bonds to the urgency. Momentum is not only then accelerated; it’s also geared to scale.

Brewed From Within
#11 📖 Entrepreneurship

By Ben McDougal, ago

Pain Relievers vs. Vitamins

In agony, we reach for pain relievers made to kill the torment. When everything feels normal, we may pop vitamins to support a healthy lifestyle, but missing a day is not a problem. For every vitamin, the medicine cabinet has just as many intentions collecting dust.

As we study a team/product/service, is true pain for real customers being relieved, or it a nice-to-have idea that may (or may not) provide unquestioned value?

When people like the idea but hesitate to buy, you have a vitamin. If you always have to explain why someone needs it, you have a vitamin. If it’s unclear what you have, you have a vitamin. Pain killers are easy to spot. They sell as fast as supply can keep up with demand.

Ongoing customer discovery keeps a pulse on demand and helps us build with product-market fit. As we ease true pain, stories that sell (marketing) should highlight the results that target customers desire without question. Forget the jargon, impressive features, and pretending to be passionate. Lean into the pain.

Brewed From Within
#6 📖 Entrepreneurship

By Ben McDougal, ago

Super Sentence

Football is a battle between modern gladiators. Did you know there are only 11 minutes of live action in an average game? Even with such a small window of actual gameplay, think about the endless pregame analysis, commentary, predictions, production, and post-game highlights.

Each week, this machine churns attention, but the Super Bowl takes it to another level. With two weeks leading up to game day and another week for post-game highlights, the Super Bowl lasts three weeks. That’s up to 30,240 minutes of potential attention the National Football League can earn from each consumer. With those 11 minutes of live action representing only 0.04% of this three-week long spectacle, clearly the Super Bowl is about more than the game. It’s also about the host city coming to life, a stadium full of fans, the TV commercials, the halftime show, the food, and everyone sharing the spectacle together.

This is not by accident. The NFL understands their audience. They’ve achieved product-market fit, and since 1920, they’ve built around what they do best. This entertainment behemoth does American football really well, but $15 billion in annual revenue doesn’t come from 150 snaps per game. It comes from being outstanding at one thing, while not getting complacent. This strengthens an existing fan base while allowing experimentation to guide strategic initiatives to further increase the audience.

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If your company was given a free Super Bowl commercial, who would be your target audience? What story would you tell? What action would you want viewers to take, and would you be ready to convert attention into trust when they took that action?

The NFL makes product-market fit look easy, but building something that satisfies true demand is harder than it sounds. Avoid getting sacked by admitting that your idea isn’t special and the future of your business relies on your ability to consistently execute. Trust that early success relies on clarifying your value proposition and evolving your business based on continued customer discovery and your ability to collaborate with those around you. This takes finesse, thick skin and a peculiar combination of urgency mixed with patience. As you secure more paying customers, you may be given a chance to broaden the impact.

Can you describe what you do in one super sentence? Now, what’s another concise sentence to highlight your current quest? Let’s have a sequenced follow up. Finally, articulate how this work feels like play, celebrate members of the team, or highlight other fundamental elements of the business.

When these super sentences come together, you’ll have a playbook to better understand the realities of your work and how to earn first downs in the market. Over time, with an advancing playbook, small wins lead to larger victories on and off the field.

Brewed From Within
#16 📖 Entrepreneurship

By Ben McDougal, ago