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.
Extra Shot
“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
1 Comment
Ben McDougal · September 14, 2026 at 4:17 PM
ORIGINAL – 9/5/22
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.
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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