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

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.

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.

Ship It

We are all artists. No matter what you create, there’s a distinction between creating art and shipping it.

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Here’s a useful definition of art. How does (re)defining art this way change the way you think about your own contributions? What is your art?

My favorite author, Seth Godin, often writes about going beyond the status quo by creating remarkable art. As we explore and expand our creative practice, Godin also suggests that if we don’t ship our art (i.e. send it out into the world), that it is all for naught. He leans on how art is all is about connection, and if nothing is shipped, there cannot be connection.

Entrepreneurs, intrapreneurs, side hustlers, students, and community builders willing to ship, fuel positive change with their art. Unfortunately, the ego often fears external evaluation. This fear is compounded when a lack of success may occur, which is always possible. As apprehension calcifies over time, it becomes tough to resit the temptation of hiding our thoughts, emotions, and activities within the safety of solitude.

Creating art to enjoy by yourself can build skills and provides internal layers of sentimental value, but to go beyond the status quo, push past the fear of feedback.

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Failure is an illusion. We either succeed or learn.

The world is loud, so avoid wasting time shouting just to make noise, but know that we need you to ship your art. This encouragement is not an excuse to rush into bad ideas, ship something that hasn’t received proper attention, or not deliver on a promise. It is however, a friendly reminder that pursuing perfection can devolve into an enemy of progress.

We’ve all heard inspiration like that before, but listen to those you admire. Perfection is rarely required when all you need is enough success to continue creating art. Let such liberation fuel confidence. Translate expanding confidence into fresh curiosity. Augment this curiosity with creative action. Rinse and repeat.

As belief in oneself grows, one interesting hesitation is disguised by good intention. We tell ourselves it’s not wise to be too self-serving. This is virtuous, but sometimes endless humility makes silence feel safe. As we protect ourselves by staying quiet, a self-limiting restraint develops. For example, many people find writing into journal to be therapeutic, but are quick to dismiss the idea of sharing these beautifully raw writings with others. Of course it’s good to internalize some things, but as you learn more about yourself through writing, know your art can make an expanded impact when it ships.

Ready to ship your art? Think about your own super powers and the people you care about. How might connecting these two things provide value? Experiment with small actions and as this develops into a practice, expand the connected nature of your creativity. As your art connects with those who care, find a cadence that allows you to be consistent. Seth Godin suggests that we all ship something daily, but one size does not fit all and the right tempo depends on the art you’re planning to ship. To find your own signal, consider your personal bandwidth and the audience you seek to serve. Talk with others and experiment, then tweak your timing to find the right rhythm.

If you’re shipping art, I’d love to hear what makes it remarkable and how you stay consistent. If you’re looking for new ways to make a ruckus, the Roasted Reflections library and my curated Resources page will help spark fresh movement.

No matter your current state of now, thank you for continuing to create art. More important, thank you for being courageous enough to ship it.