Side Hustles

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

Minerva

The cosmic pursuit to find Pluto is a neat example of how imagination, obsession, and reason align what can be seen. After scientists at the Lowell Observatory finally discovered “Planet X” in 1930, the world weighed in on what to name it. Let’s brew on naming your project.

As discovery releases new realities, a great name established an identity. A name makes a project feel real and allows you to talk about your ideas with others. It also creates an identity to build your marketing around. If you’ve been thinking about your project for a while, a good name may emerge. If you’re struggling, here are three ways to land on something scalable.

1. Be descriptive. If it’s impossible to guess what you’re offering at first glance, you’re taking an early gamble. Hyper specific names may stand out in the moment, but too much definiteness can limit your ability to evolve. Attention is hard to earn, so avoid obscurity, names that may trap you, or anything that makes your business hard to remember.

2. Verify your name is available. It’s tough to set yourself apart while still being easy to remember. As you consider naming a business, get creative, but do your homework before you fall in love. Research existing trademarks, domain names, social media accounts, industry competitors, and funky spellings.

3. Think long-term. To withstand the test of time, consider how this name can support long-term growth. If the trend you’ve based a name around fades, might it make you look outdated? Will highlighting a specific location eliminate the ability to expand? In short, don’t corner yourself unless it’s on purpose.

Once you lock in a name, start using it within customer discovery to explore how it’s received by those you seek to serve. When a name clicks, align your marketing and overall vocabulary around the newly established identity. This will make your company recognizable and over time, connects you to more true fans.

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Pluto was the second choice of scientists who discovered this beloved dwarf planet. Minerva was the team’s favorite, but it was already taken by an existing asteroid.

By Ben McDougal, ago

Eclipsing 40

I sit atop this hill, soaking in the darkness of a total lunar eclipse, verbally dictating this short reflection to celebrate my own 40th trip around the Sun.

As our pale blue dot moved between the moon and our closest star, I first noticed the moving shadow’s blurry edge. As I think about the time we spend on Earth, so much of it is devoted to finding our place in the universe. Even when we are so close to perfect alignment, the blur of subtle distractions will remain constant.

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Perhaps this transitory quest for totality is the impossible pursuit that makes life so much fun.

Anticipation takes over as the final sliver of moonlight goes dark. The orange haze of this blood moon is now the only cloud in the sky. Even with the cool breeze, city lights, distant traffic, and frogs burping, the twinkling stars seem to serenade the silence of this moment. As the darkness holds time still, an eerie peacefulness is accompanied by a welcomed loneliness.

My thoughts soon sync into the shadow of this cosmic darkness. This makes it useless to resist the overwhelming appreciation I have for so many people who have given my life meaning. The past 40 years are a tribute to those who brought me to this place and to the family I’ve chosen every step of the way. Thank you.

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Jodie and Kate, you are the light of my life and my own totality. Together, you set me free to wonder and have taught me the meaning of life. I’m only 40 years old, so while I look forward to much more of our story being written, whenever I do turn my final page, know that I’ll always be with you and wouldn’t have changed a single thing. I appreciate these quiet tears, knowing that my greatest achievement will always be the honor of being part of US forever.

Within the darkness of totality, I’m soon struck by the discomfort I feel, not knowing when the moonlight may return. We’ve all heard how dark it is before the dawn, yet it still feels natural to consider things that have not gone to plan. Accepting past failures, broken relationships, and the future challenges we may face was not an expected emotion, but perspective determines how we respond. I’m thankful that it’s hard to think of anyone who may need to hear this, but if I’ve ever wronged you in anyway, I want to say that I am sorry and only wish the best for you.

As the first sliver of moonlight returns, eminence joy and assuring enthusiasm seemed to rush over my mind and body. It was as if the light of our cherished moon had never been brighter. The subsiding shadow of our planet slowly released moonlight back into the night sky, which lit renewed optimism for all that is still to come.

I am so blessed to have brewed 40 remarkable years into this life. As the full moon shown brighter than ever, so will my appreciation for all that we share.

By Ben McDougal, ago

Playforce

Work and play are often seen as distinct and different, but the expectation of top talent has evolved. People crave a connection to enjoyable activities that deliver a sense of purpose and belonging. When work feels like play, the fun environment invites people to take on bigger challenges. To support the future of work, students, educational organizations, employees, and employers must adapt together.

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Welcome to your first taste of a new community-driven initiative that will feature special guests sharing occasional contributions. Interested in collaborating? Let’s chat!

When we think about work that feels like play, it’s not just pinball all day. The definition of “fun” is to spend time doing an enjoyable activity. When a team has fun with satisfying work that matters, the group’s true potential is unlocked and individuals are more likely to become indispensable. This leads to more generosity, laughter, caring, scientific questions, learning, gift-giving, and mapmakers eager to go beyond what’s expected.

A recent study identified 16 trends that are shaping the future of work. It found that, in addition to more flexibility and fair wages, employees want greater autonomy. Employees want the freedom to be creative and to find purpose in the way they spend their time. When this balance is achieved, people are happy and the sense of satisfaction allows them to do their best work. Along with more innovative productivity, this culture also leads to lasting retention.

As today’s workforce is transformed into tomorrow’s playforce, it’s important to consider the difference between work that feels like play, compared to work with playgrounds nearby. When fun activities only serve as a distraction, the facade of fun will wear off. It’s also good to remember that what’s fun for one person could be more of a chore for others. Personality assessments and ongoing interactivity will help you understand individuals and the part they play within the system. The better people know each other, the more inclined they’ll be to act themselves. Acting professionally shouldn’t mean dimming one’s personality. The more comfortable people feel at work, the better they’ll be able to focus on what’s important. Too often, attempts to optimize employees’ work-life balance stem from a flawed assumption that we must create boundaries to differentiate life and our work. Perhaps the opportunity and the future of work, is to create an experience where the two coexist as one?

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This caffeinated contribution was written by Elizabeth Tweedale. Elizabeth has (co)authored six books, exited an AI company called GoSpace, and is now the CEO of Cypher Coders, the UK’s leading coding school for children. She’s passionate about family, preparing kids for the future, and can be found in our Roasted Reflections group.

If the future of work is fun, we must guide children away from an outdated “workforce” and toward a “playforce” to activate creativity, productivity, satisfaction, involvement, and purpose. The world is their playground and no permission is needed to contribute. Education can be about delivering access to skills, tools, and community. When children are encouraged to connect, play games, be kind, and learn with passion, they engage not because they have to, but because they’re having fun. This empowers students and as they reach the playforce, they’ll understand the superpowers they’ve nurtured in their own areas of interest. Beyond the classroom, this translates into employees and employers who are more likely to enjoy their work when given the opportunity to do what they’re best at.

As we see/hear in the closing chapter of YDNTB, “life is too short not to enjoy your work.” Together, let’s change the equation to make work a lifestyle, which sets us free to have fun making a difference.

By Ben McDougal, ago

First in Line

There’s something special about being first in line.

Being at the front of a line means you’re committed. You’ve made some form of sacrifice to ensure you’re first to experience something you care about. The unknowns of arriving in time to secure this coveted spot requires a concerted effort, but a sense of pride materializes when everything goes to plan. When was the last time you where first in a long line? My hope is that the wait was worth it!

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FliteBrite is bringing our beer festival app out of hibernation. Here’s the line that inspired this week’s writing.

When I think about being first through the lens of innovation, first in line is not such a desired position. Being first gives entrepreneurs a chance to take an early lead, but early leaders don’t always win in the end. The headwind is strongest when you’re in front. When your art involves creating something the world has never seen before, enthusiasm from early adopters is often met with pernicious friction. One common source of friction is the almost endless time spent educating the prevailing market. This protracted process wears on even the most resilient and exhausts resources every step of the way. Along with frictions that come with being first, without any clues from past success/failures, it’s harder to avoid potential pitfalls as well.

There’s value in a head start, but the early market leader often falls behind the innovation curve. Please, never hesitate to forge into the unknown, but remember that when you lead, others will always be chasing you. If you’re building in front, stay ahead with epistemic humility, a challenge network that invites you to be wrong by avoiding groupthink, a genuine desire to accelerate others, and bold leadership that allows intrapreneurs to stay wild. If you’re the one chasing, which is far more common, you’ll need to be innovative to find product-market fit, but it’s nice knowing there’s an existing path with fresh opportunities to champion change in an existing environment.

Alright, let’s add some sugar.

What if we don’t have to be in the line at all?

The front of any line may be a traditional way of getting ahead, but this requires time with no guarantees and you’re still relying on some else to let you in. If this activity is something you really enjoy, be conscious of how business can sometimes kill your passion, but there’s usually a way to be less of a spectator by getting more involved. One way to do this is by combining your creative skills and an entrepreneurial spirit to wedge yourself into the experience itself. This requires initiative, but volunteering, building into a side hustle, or using content creation skills can quickly become your ticket to skip the line all together.

By Ben McDougal, ago