Generosity

100th

I’ve written into Roasted Reflections every week for almost two years and this is the 100th entry!

I put a lot of thought and energy into every one of these friendly jolts, each brewed to keep you building in different ways. Whether it’s taking the time to read, sharing a quick reply, crafting a caffeinated contribution, or just paying the good vibes forward, I want to thank everyone who starts your Wednesdays with me. As I reflect on this literary journey, here are things I’ve appreciated along with way.

– Writing helps us understand ourselves.

– Translating ideas into words is easier the more you do it.

– Verbal dictation can produce a base, then a round of editing brings things together.

– Having a home to organize your writings is more lasting and easier to share anywhere.

– It’s challenging to keep writings concise, but this makes more impact in less time.

– Attention is hard to earn, let alone keep. Stay curious, listen to those you seek to serve, and diversify content creation to stay interesting.

– If you’ve written a book, a complimenting library of shorter entries make it easy to connect ideas back to the book while sharing organized thoughts based on the context of any conversation.

– The thesaurus is a fun tool thats helps us learn new ways to express ideas with fresh vocabulary.

– Publicly publishing your art creates connection.

– I enjoy encouraging others to write.

– Writing is not free. It costs time.

– Without much financial capital involved, the ROI of this type of initiative comes in the form of intellectual, human, cultural, and network capital that churns evolving layers of satisfying value.

– Even so, doubt creeps in. I find myself wondering if I’ll run out of meaningful things to write about every week. Would anyone care if I quit sharing these reflections? If I do decide to quit or reduce the frequency, what’s my why and how might I change the way I ship this art? Would I miss the sense of connection or somehow lose momentum? Perhaps there’s peace knowing the impact can continue being made without weekly additions? I plan to push through these dips as long as I continue to enjoy the challenge, but it can be lonely when we give our best, so please know that I always welcome support from those who have walked this path before.

– Consistency requires sacrifice.

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By Ben McDougal, ago

Tenured

Recognize, connect, and support those who consistently delight those they serve over a prolonged period of time. Rewarding such an initiative makes sense, but at what point does the comfort of a rewarded role devolve into a willingness to sail into the sunset?

When starters run into the aloof, misaligned energy can lead to a standoff. Time is the ultimate release, but what if progress is needed now? Every situation is different because of the complexity of an environment and the people/organizations involved, but here are tactics that seem to work no matter the circumstance.

The first uses social currency. It requires a change maker to set their ego aside, and instead, celebrate all that’s been achieved by the accomplished, yet tired gatekeeper. Use respect, kindness, and appreciation to form a bond. Relationships that feel less transactional often create leniency toward new ideas. When a crack in the wall of inactivity is created, be glue that maintains the integrity of the existing system. For example, “I’m too busy” is a common qualm, so lean into that pain by offering to execute on the idea that has sparked mutual interest. It’s important to be realistic in these moments, because when promises are made, credibility is on the line. As you not only light a path toward progress, but also champion change by evolving ideas into reality, trust is gained and your ability to continue making a ruckus increases. Want to extend your leash further? Take responsibility for failures, but give all the credit away when success is achieved.

If a larger organization is involved, another interesting tactic invites the tenured leader to level up the team by activating a colleague. This provides a new hire the chance to get involved within the entrepreneurial ecosystem, while the organization is seen as engaged within their community. It’s hard for some to understand that time spent in the wild is often more valuable than clocking time in the office, but if the organization allows this person to show up without limitation, everyone wins. The new community member feels the innovative energy and brings more intrapreneurial vibes into the organization, while the community benefits by having another trusted organization in the mix.

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“The way we make things better is by caring enough about those we serve to imagine the story that they need to hear.” -Seth Godin

If you’re reading this, you may be tenured, but it’s unlikely you’re tired. That said, we’ve all found ourselves in a motivational rut or lacking a clear sense of purpose. Along with a few solid sleeps, when I feel the urge to settle, it helps to have fun, build into other areas of your career portfolio, take a few days to rest if necessary, and then get back into the startup community. This creates opportunities to #GiveFirst, ask for help, or get extra curious about the creative work of others. Soon you’ll find new opportunities to collaborate.

New connections that emerge can bring you out of the motivational rut. They can boost your care meter and will add fresh personality to your work. Along with sparking fresh direction(s), you’ll be motivated by others and soon find new ways to be generous with your art. If you’re still thirsty for motivation after tapping into the entrepreneurial ecosystem, I’m here for you as well. Together, we can refuel the idea machine to avoid wasting any more time with being tenured, but tired. Sleep when you’re dead, my friends. Let’s keep building.

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“There will come a time when you believe everything is finished. That will be the beginning.” -Louis L’Amour

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

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

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