When the Day to Day Gets Boring: What’s Next for Senior Leaders?

After I’ve worked with someone for a few months, our conversations naturally start to shift to a more existential direction. They learn new skills, things start humming along but the results just aren’t personally exciting. Like all things in life, you have to adapt and grow or you’ll get bored and frustrated.

What happens when the job is going fine, the results are strong, but the work itself starts to feel boring?

At a certain point in a career, the tactical challenges have been solved a dozen times over. You know how to drive revenue, manage teams, and deliver quarterly results. What you don’t know is what will keep you motivated and engaged for the next five, ten, or even twenty years.

More and more people want to work later into their lives. This poses an interesting and relatively new challenge. When most people would have mastered all the tactical and dabbled in the cultural for a few years, it’s time to retire. But if you want to stay in the game longer…..how do you stay interested? What is the next level?

For senior and executive leaders, there are usually several directions available. Stay and pursue ownership through equity or a board seat. Leave for a bigger title at another company. Strike out on your own as an entrepreneur or consultant. Leverage your ability to get results fast and “mail it in” while giving more energy to your personal life.

This menu of options can be both exciting and paralyzing. Paralysis can lead to apathy.

Apathy isn’t pretty.

So how can you lock in and move forward at the same time?

In coaching sessions we ask:

What will keep me engaged when the scorecard is no longer enough? Where can I use the wisdom I’ve built to make a real impact?What kind of culture do I want to build for myself and the next generation?

For many, this means implementing two scorecards. One for performance, with the financial and operational results you’ve always been measured on and a new one for culture, with the legacy of leaders you develop, the systems you institutionalize, and the environment you shape.

What’s really cool here is that you don’t just adopt the culture of the company as it is today. When you reach the top, you get to create a personal vision statement and blend the two together.

This is what people really mean when they talk about legacy. They create something they really want to be a part of and they make it better for the next team. You can only do this with decades of experience behind you.

When we move into this work, we see personal energy return, even in a role you’ve held for years. It’s not about waiting for something new to appear. It’s about shaping what payoff looks like for you. That might be equity, influence, or simply knowing you’ve passed on your wisdom to the next generation.

That’s the next level.

These conversations are some of my favorites. They’re not about fixing the quarterly forecast or solving a people issue. They’re about the real stuff. The “what’s next for me” stuff. And that’s what people really want out of coaching.

There’s no single right answer. Some leaders lean into ownership. Others chase a bigger title. Some reinvent themselves completely. The common thread is that the ones who thrive decide they have some say in the matter.

So if your day to day feels a little boring right now, maybe that’s not a sign you’re stuck. Maybe it’s just an invitation to start playing a more advanced game.

Fun read on this topic: Arthur Brooks, From Strength to Strength.

Live & LeadWell,

~E