Entrepreneurship

Milestones

Big or small, internal or external, milestones help people identify with progress. They draw lines in the sand. This clarifies goals while supporting short-term accountability and long-term motivation.

Entrepreneurship is a community sport, but creative problem-solvers working to build a business are still competitive. Milestones tap into this competitive spirit by gamifying a performance-based culture. Recognizing milestone achievements can also boost morale and further unite a team. If you’re collaborating with mentors and/or an advisory team, milestones help keep everyone on the same page as well.

As milestones are established, be sensitive to the diversity of your team. Find creative ways to equitably encourage new and more experienced team members. One easy way to do this, is to establish a few tiered categories for different types of milestones. As you diversify milestones, we’re not creating so many that they become pointless. Instead, you’re curating a variety of dynamic signals that can activate different emotions along a connected and sustained timeline.

As milestones are completed, the culture is nourished with celebration, which we’ll sip on next week!

By Ben McDougal, ago

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

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

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