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 & Tired

Consistent action transforms opportunity into potential. As experience expands, successful leaders are rewarded with increased capacity, attention, and control. Along with many cultural motivations, financial capital is often involved as well. These alluring incentives make it no surprise that many prominent positions are held for too long. Leadership calls for lasting commitment, and long-term leaders can sustain longstanding progress.

But how can we interact with complacent leaders who have become tenured and tired? People who are coasting. People who act as gatekeepers to progress. People who hold on to power from the past.

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

The first leans on social currency. It requires us to set the ego aside and instead celebrate all that the accomplished, yet stubborn gatekeeper has achieved. 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 the 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 ideas that sparked mutual interest.

It’s important to be realistic in these moments, because when promises are made, credibility is at stake. As you light a path toward progress while you also champion change by evolving ideas into reality, trust is gained and your ability to continue making a ruckus increases. Along the way, take responsibility for failure, but give credit away when success is achieved.

If an organization is involved, another tactic invites the tenured leader to level up their team by activating a colleague. This provides a new hire the chance to get personally involved within the startup community, while the organization is seen as being engaged within the entrepreneurial ecosystem. It’s hard for some to understand that time spent in the wild is more valuable than clocking time in the office, but if the organization allows this person to show up, everyone wins. The new community member feels a boost of innovative energy and brings intrapreneurial vibes into the organization, while the startup community benefits from fresh perspectives and expanded support.

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“Make things better by caring enough for those we serve, to imagine the story they need to hear.” –Seth Godin

If you’re tenured and feeling tired, you’re not alone. We all experience motivational ruts and emotional dips. Even in ideal situations, leading for any length of time is depleting. Markets, products, services, teams, strategies, and cultures change as well, which shifts how your own interests and skills align over time. If haphazardness is left untamed, a lack of purpose impacts your attitude and everything around you. When the urge to settle drags us away from being our best, setting new milestones helps to spark fresh enthusiasm. Other galvanizing tactics include trying something new, developing other areas of your career portfolio, resting, reading, writing, hibernating for a longer break, or quitting if it’s time to write a new chapter. Even if it’s challenging, make an effort to find fun and be wary of consuming more than you create.

Once rejuvenated, get back into the startup community. Even if we’re just listening, we can feel invigorating energy from the creative ambition of others. New opportunities will emerge for experienced leaders, but there’s no rush. Instead, adopt the inspiration. Let others lead, and use fresh intensity to break through emotional lulls as you uncover more ways to make an impact with your art.

Brewed From Within
#61 📖 Leadership

By Ben McDougal, ago

Maverick

Founders ride highways to the danger zone. They’re good in discomfort and look to horizons, knowing the edge is where it’s at. Tactics can be learned, but steady action, confidence, humility, and persistence help us embrace entrepreneurship for what it is: a lifestyle.

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.

As we build at the speed of trust, we work to understand those we serve, which almost always leads to some form of success. This may be relentless customer discovery, a side hustle that brings us to life, the innovative role we build as a linchpin inside an existing organization, or that first hire who grows a scaling business. Every mission is impossible, until lasting commitment helps us feel our way through it.

As we fly beyond our own limits, don’t think. Make entrepreneurship a lifestyle of continuous learning and stay supersonic to become prolific in all that we create.

Brewed From Within
#3 📖 Entrepreneurship

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

Serendipitist

Do things always seem to work out for you?

Internal narratives and external experiences make the cultural consequences of serendipity hard to refute. Serendipity may be pseudoscientific, but things we dedicate attention to will attract more of the same.

The appetite for welcoming serendipitous collisions is often enhanced by the optimism that an entrepreneurial lifestyle constructs. No matter the source or how often stars align, many of us are or have the potential to be a serendipitist.

Serendipitists seek adventures that invite, sometimes even require, different layers of serendipity. The extent to 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 we experience this charming phenomenon.

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What’s normal for a spider is chaos for the fly.

Leaders who manifest serendipity are often called lucky. Both require proficient preparation, openness, and timeliness, but serendipity is deeper. It calls for earned trust and perseverance. Serendipitists realize good fortune is not an accident and they share this mantra in their creative practice.

Serendipitists show up.
Serendipitists say yes more often.
Serendipitists assume positive intent.
Serendipitists seek to understand.
Serendipitists are empathetic.
Serendipitists stay curious.
Serendipitists are generous.
Serendipitists kill with kindness.
Serendipitists fuel positive change.
Serendipitists have fun and die empty.
Serendipitists play long-term games.
Serendipitists are consistent.

When you sense serendipity, recognize the blessings that come from this positivity we squeeze into the universe. As we keep serendipity brewing, we make new dots to connect and can invite others to turn up their own serendipity even more.

Brewed From Within
#112 📖 Life & Happiness

By Ben McDougal, ago