Not to Lose

Whether it was traveling with the teams my dad coached as a kid, playing club soccer at an early age, monopolizing my time in high school, playing all through college, or being the focus of my first entrepreneurial venture, soccer was a part of my identity for over 20 years. I’ve since shifted toward the more secret exercise of golf, but memories remain, and sports have so many playful metaphors.

Sports and other organized activities help us push to be our best, and the sense of belonging is the real magic.

No matter the sport, it can be easy to get ahead before slipping into a dangerous trap. Instead of staying sharp by maintaining the offensive pressure that earned an early advantage, it’s natural to start playing not to lose.

In soccer, this often means a team sinks back into an overly defensive formation. Less variety invites frantic desperation, and the added pressure often leads to the opposing squad scoring an equalizing goal. Even if the need for another goal shifts your team back into a more balanced attack, the momentum has shifted.

When applied to business, getting ahead and then playing not to lose can be seen all over the map. For instance, snagging a few early adopters, then assuming customer discovery is over. Hiring new talent, then just hoping everyone can work together. Launching a new product with existing customers, then not supporting them through the chasm of change. Securing product-market fit, then avoiding innovation due to a misguided sense of risk. Finding generous mentors, then forgetting to nurture relationships. Those are just a few ways we get ahead, then play to lose, but many leaders are lulled into this trap.

Tactics to stay ahead differ based on situational factors, but when in doubt, trust that uncertainty is certain. Be strategic to avoid recklessness, then maintain pressure and stay on the offensive by leaning into the pain.

As you find fresh ways to serve customers, continue celebrating milestones and stay ahead with more initiative to keep playing beyond the fear of losing.

By Ben McDougal, ago

Feng Shui

Peace awaits those who appreciate all that is without worrying about all that is not. That said, things will not just fall into place. It takes initiative, consistency, awareness, and sacrifice to find your own equanimity.

Similar to how we decorate our environment to harmonize with nature, we can connect elements of our career portfolio to feel the benefits of feng shui.

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It’s not a rainy day. It’s free water.

The world is loud, and endless distractions make us feel frantic when there’s so much to do. Being present along with a quiet appreciation of understated beauty keeps us centered. As mindfulness becomes part of our practice, it’s easier to slow down just enough to ensure we don’t miss life along the way.

The places we visit, the people we’re with, and the art we ship all connect through us. Over a lifetime, we become a destination for others, and this becomes our gift.

When there’s passion, humor, diversity, intellectual humility, and harmony within our own environment, the impact of our gifts are lasting and the way we invest time with others will add up in the end.

By Ben McDougal, ago

Tenured & Tired

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

Ideaworks

Our daily lives gobble up mental bandwidth. If you’re interested in building a business, compelling ideas may hit but lasting intention is needed to build momentum.

It’s unlikely that lightning will strike in a single brainstorm. Instead, combine detail-oriented initiative with pure wonder and open-mindedness to attract earned luck, thanks to serendipity. As ideas fueled by action create chemistry over time, different combinations will map more opportunities.

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We get what we repeat.

How might combining ideas be like a colorful fireworks show? Let’s begin with the anticipation a crowd feels before the show. Then a bright light flashes, and the sound of that first colorful explosion is celebrated.

To get color popping in the night sky, a fuse was required to spark early progress. Fuses such as linking slowness with urgency, actively listening, allowing new experiences to shift your perspective, and always staying curious give the idea machine more ways to continuously flip the switch.

As each fuse is lit, we hear that thump of a distant firework being shot into the sky. This sound of propulsion is like ideas darting into the limitless atmosphere of our mind.

With each idea sparked, there’s a thrilling hope that what’s about to pop is exactly what we’ve always wanted. Even if it’s not an absolute showstopper, each ideawork sparkles with different colors, shapes, and sounds that inspire the sky and connect into the broader experience.

Looking up into the stars, we appreciate each blast in different ways, based on the vantage point. This awakens the fact that every idea has value. Bad ideas lead to better ideas. This can spark great ideas that reverberate, and when given the space to merge, combine into a fantastic reality.

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Don’t wait for next year.

As ideas pop to create a tune, it’s like the grand finale a crowd waits for. The audience may scurry in different directions after the show, but they’ll keep talking about the experience long after that floating smoke clears.

When songs rhyme with a melody, the idea machine sparkles. When execution is a habit, even duds can’t stop a remarkable show from lighting up the sky.

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.

By Ben McDougal, ago