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.

It’s easy to see how endless whys may lead to frustration (especially when it’s bed time, eh), but I’ve found joy in making these winding whys into a fun challenge for myself. Instead of shutting things down, I enjoy trying to quickly answer every why with an accurate answer. Can I mindfully outlast the youngster’s attention span? What fun!

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I’ve enjoyed winding whys many times, but “Dad, why do you love me?” gave me pause. I found myself feeling appreciative as I tried to coalesce endless reasons into one answer.

As I poked around, it felt trite to reflect on how humans have so many whys we can not answer. Instead of going down the paradoxical path or leaning into understanding our own whys, I found the Five whys interesting.

Developed by system thinkers inside Toyota back in the 1980’s, this iterative Five whys 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 rigid technique has critics and would seemingly lead to shortsighted interpretations, but it was fun learning about this historic use of why. Knowing the value of complexity vs. simplification, as well as, so many other methods like active listening, Socratic questioning, casual diagrams, storytelling, inverse charisma, and pure wonder, the Five whys may not answer all the winding whys of our world, but perhaps it’s another tactic to throw in the mix.

Why not?

Ideaworks

As color pops in the night sky, let’s brew on how sparking innovative business ideas might be similar to how we experience a breathtaking fireworks show.

Alright, so you’ve got the chaos of life all around you, but this moment’s focus is first directed toward finding a place to park. This frenzy has me reflecting on how our daily lives gobble up so much mental bandwidth. If you’re interested in building a new business, interesting ideas may strike within the madness all around you, but innovation takes intention. Such intention can lead to momentary movement, but it’s unlikely that lighting strikes just because we decide to brainstorm in single servings. Instead, making creative day dreaming a habit will invite serendipity in the mind. As ideas emerge and connect over time, different combinations will help map out more valuable opportunities.

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You get what you repeat. I’ve enjoyed hearing readers share how the ideation exercise featured in YDNTB provided the practice they needed to become an idea machine.

Alright, so you’ve found a spot to enjoy the fireworks? The anticipation has the crowd excited and then… a bright light flashes, right before the unmistakable sound of the first explosion arrives. The show is underway!

Shifting this spectacle back into our metaphor for innovative ideation, I think about the fuse that starts it all. There must be a way to catch fire, eh. Perhaps a willingness to slow down while maintaining urgency, actively listening, being open-minded, allowing new experiences to shift your perspective, leaning into community, and always staying curious gives the idea machine more ways to continuously flip the switch?

As each fuse is lit, we hear that thump of a firework being shot into the sky. This sound of propulsion is like ideas darting into the limitless atmosphere of our mind.

With each idea sparked, there’s a thrilling hope that what’s about to pop is exactly what we’ve always wanted. Even if it’s not the show-stopper we wanted, each “ideawork” releases different colors, shapes, and sounds that inspire the sky and connect into the broader experience. Each blast is also seen in different ways based on the vantage point. This awakens the fact that every idea has value. Bad ideas lead to better ideas. This can spark great ideas that reverberate and when given the space to merge, different ideas combine into what can be evolved into a fantastic reality.

As individual ideas pop to create a tune over time, it’s like the grand finale everyone waits for. The audience may scurry in different directions after the show, but they’ll keep talking about the impact long after the floating smoke clears. When we consistently invite different ideas to form a melody, it nourishes a system geared to be remarkable when the fuel of habitual action is applied. Keep sparkling my friends.

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Don’t wait for next year.

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

Perpetual

It’s hard to stop anything that repeats so frequently it seems endless. There’s infinite ways perpetuity could be good or bad, but never ending happiness, trust, love, hard work, fun, generosity, action, wonder, and learning seem like safe bets.

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It’s not whether you know how, it’s whether you will.

Being inspired by so many remarkable people (like you), has instilled a lasting appreciation for consistency within the entrepreneurial lifestyle. Perpetual feels like a cousin to persistence, so without airdropping the final chapter, here’s a short excerpt from the closing moments of You Don’t Need This Book: Entrepreneurship in the Connected Era.

As entrepreneurs traverse through the unknown, setbacks are inevitable. Each conquered setback makes an entrepreneur more resilient. As resiliency bonds with experiential knowledge, focused determination makes setbacks less distracting. Eventually, setbacks become more like interesting challenges for problem-solving entrepreneurs. This hardened mindset welcomes endless suffering. Such willingness to suffer unlocks a key to entrepreneurship. Passion.

Passion fuels persistence, and persistence is a wild card. Passionate persistence combined with obsession, allows anyone to achieve entrepreneurial success.

You’ll build when others don’t. You’ll savor projects longer and you’ll fight through dips that made others quit. You’ll be comfortable with uncomfortable and you’ll enjoy making a ruckus every step of the way.

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Belief in one’s self is contagious.

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.