Family

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

Totality

I sit atop this hill, soaking in the darkness of a lunar eclipse, reflecting as I celebrate 40 trips around the Sun. As our pale blue dot moves between the moon and our closest star, I first notice the moving shadow’s blurry edge. As I think about the time we spend on Earth, so much is devoted to finding our place in the universe. Even when we feel alignment, the blur of distractions will remain constant.

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. The twinkling stars seem to serenade the silence of this moment. As the darkness holds time still, an eerie peacefulness is accompanied by welcomed loneliness. My thoughts sync into the shadow of this cosmic darkness. It becomes useless to resist the overwhelming appreciation I have for so many people who have given my life meaning.

Extra Shot

Jodie and Kate, you are the light of my life and my own totality. My greatest achievement is us. We make each other better, have fun, and experience the meanings in life. One of my favorite things will remain writing life’s stories together, but when I do turn my final page, know that you’re both forever loved, I’ll be with you always, and I wouldn’t have changed a thing.

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 future challenges 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 any way, I want to say that I am sorry and wish only the best for you.

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Perhaps the transitory quest for totality is an impossible pursuit, but one that provides meaning and makes life fun.

As the first sliver of moonlight returns, eminent joy and assuring enthusiasm seem to rush over me. It’s as if the light of our moon has never been brighter. The subsiding shadow of our planet slowly releases the cherished moonlight back into the night sky, which lights renewed optimism. As the moon shines brighter than ever, so does my appreciation for all that we share. Now and forever, thank you.

Brewed From Within
#107 📖 Life & Happiness

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

The expectation of top talent has evolved. People crave a connection to time that delivers a sense of purpose and belonging. When work feels like play, the lively environment invites people to take on bigger challenges. To support the future of work, today’s students, educational organizations, employees, and employers must adapt together.

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 and to feel engaged. 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.

EXTRA SHOT

This contribution was written by Elizabeth Tweedale. Elizabeth is a founder who is passionate about technology education, AI, and preparing children for the future.

In addition to more flexibility and fair compensation, 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 they feel allows them to do their best work. This culture leads not only to more innovative productivity but also to lasting retention. It’s an oxymoron, but a playforce earns this lasting retention through a shared freedom to believe in the mission, people, target market, service/product potential, and timing.

Too often, attempts to optimize employees’ work-life balance stems from a flawed assumption that we must create boundaries to differentiate our life and our work. The idea of a “work-life balance” is a corporate illusion not suitable for the entrepreneurial lifestyle.

The neon future of work creates an experience where life and work coexist as one. This is possible when labor looks like work to others but feels like play to us. This activates a culture where retention is natural due to a genuine interest in a shared direction. This type of playforce environment welcomes anyone to leave when a quest is no longer the best opportunity for their life. This bizarre freedom is balanced because it’s shared by leaders who assume positive intent but can also make moves when an employee no longer aligns with the time. This mutual admiration transforms a team that shares a creative way of being.

As today’s workforce is transformed into tomorrow’s playforce, let’s consider the difference between work that feels like play, versus work with proverbial playgrounds nearby. When fun activities serve as a distraction, the facade of fun will wear off.

It’s also important to remember that what’s fun for one person could be more of a chore for others. Personality assessments and ongoing coopetition help leaders sense team dynamics. Acting professionally does not mean dimming one’s honest personality. We want people to be themselves.As professional comfort is paired with an eagerness to make things better, people can focus.

If the future of work is play, we must activate children with creativity, involvement, and adaptability. The future is their playground, and no permission is needed to contribute. Education can be about delivering access to culture, skills, tools, and purpose. When children connect, play, and learn with passion, they engage not because they have to but because they’re having fun. This supportive sandbox empowers students to win the game of education and then go beyond it. As students grow, Playforce Principles help them understand superpowers and build beside evolving interests.

This translates into employers and employees who enjoy significant roles that feel tailored for what they’re best at. Together, we can change the equation and make work our lifestyle, setting us free to have fun while making an impactful and lasting difference.

Brewed From Within
#56 📖 Leadership

By Ben McDougal, ago
You Don't Need This Book: Entrepreneurship In The Connected Era

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.

By Ben McDougal, ago