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.

Extra Shot

“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.

Extra Shot

“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.

Extra Shot

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.

Extra Shot

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

Minerva

The 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.

Extra Shot

Pluto was the second choice of scientists who discovered this beloved dwarf planet. Minerva was the team’s first choice, but it was already taken by an existing asteroid.

A name makes a project feel real. It creates identity. If you’ve been thinking about something for a while, a name may naturally emerge. If you’re struggling or feel uneasy about the name you have in mind, here’s how to fuel confidence and land on something scalable.

Be descriptive. If it’s impossible to guess what you’re offering, 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 trap you, or anything that makes the business hard to remember.

Verify availability. It’s tough to set yourself apart while still being memorable. As you consider naming a business, get creative, but do your homework before falling in love. Do not hope something may not exist; try to find it. Boldly research existing trademarks, domain names, social media accounts, industry competitors, and funky spellings. The result can be a name that is all yours versus something that may be catchy but could spawn future liabilities.

Think long-term. To withstand the test of time, consider how this name supports lasting growth. If the trend upon which you’ve based a name fades, might you look outdated? Will highlighting a 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 it connects you to more true fans.

By Ben McDougal, ago

Hole-In-One

I grew up playing golf, but inadvertently fell out of the game due to work and other priorities. I‘d been longing to get back into the game, but kept procrastinating. So, when my friend Ben asked me to join him for 9 holes to celebrate his 40th birthday at Glen Oaks, I thought… here’s my chance! (LESSON #1: yes = adventure)

At first, I was intimidated and hesitant to have my first round in 8 years be at a fancy country club. I mean, I didn’t even have golf clothes, a glove, or shoes anymore, but I figured this would be a great way to dive in head first and get back out there. So, I quickly went shopping and got a few practice swings in at the driving range. (LESSON #2: now > later)

Extra Shot

This caffeinated contribution was written by Derek Brooks. Derek is a 40.79 year old midwestern American dude who enjoys building, traveling, partying, extremish sports, and can be found in our Roasted Reflections group on Discord.

On Ben’s birthday, I showed up to find him sipping on a Miami Vice cocktail with his buddy and business partner, Sinclair. This immediately set the stage that we were going to have some fun. Golfing with Ben was awesome. Whether it was his general demeanor, his lack of grabbing a scorecard, the way we strolled around the clubhouse, or laughs along the way, this freshly minted 40 year old was a constant reminder that we were here to relax. (LESSON #3: fun > serious)

For the first 5 holes on the back 9, my subconscious nerves were getting in the way. My hits weren’t clean and the strong winds certainly weren’t helping… But despite all the double bogeys, I was still having fun and it felt great being back on the course. (LESSON #4: fun + humility + patience = growth)

Halfway through the round, I could feel the groove coming back. On hole 15, I finally snagged my first par (Ben caught a birdie, haha). After that, we walked up to Hole 16, a 168-yard par 3, with wind in our face. Feeling incredibly relaxed, I lined up with my 7-iron and hit a super clean shot. It felt great and looked even better. The ball dropped just short and left of the pin, took 2 small hops, and then smoothly rolled right into the hole. A freakin hole-in-one. (LESSON #5: openness + growth + serendipity = opportunity)

I couldn’t believe what I’d just seen. Ben and I started screaming and laughing as we ran around the tee box. We full-on bear hugged and I think he even picked me up at one point. Neither of us knew what to do or how to act, so I just threw my gold chain on and giggled while Ben pulled out his GoPro to capture the moment.

After that ace, the next hole was a complete blur, but I ended the round with a birdie on 18. If I hadn’t set my nerves/ego aside and took that opportunity to get back into the game by having my first round in 8 years at an intimidating country club, I’d still be in that procrastination loop. I would’ve never gotten my first hole-in-one or shared this incredible experience on Ben’s 40th birthday. (LESSON #6: yes + growth = celebrate)

When I think about this experience through the lens of my career as a technologist, I’m reminded that getting in over-my-head has always been the fastest way for me to grow and move forward. I’m not expecting to be cranking out hole-in-ones from here, but once again, jumping back in head first is something that I will never regret. This memorable day was the reminder I needed to push outside comfort zones, enjoy the moments, and celebrate always.

By Ben McDougal, ago