What’s Next?
When I was early in my career, I was all about the next challenge. More responsibility? Yes. Bigger team? Absolutely. A new problem to solve? Let’s go.
I was lucky to have a leader who interrupted that momentum with one simple question: “When you retire… from doing what? And why?”
It floored me. I was in my early thirties, not even close to thinking about retirement. But that question reframed everything. It forced me to stop thinking just about the next role and start thinking about the kind of work and life I actually wanted to build.
At the center of that work were values. Not just the ones that sound good on paper, but the ones that actually shape your choices. Values that act as a compass, not a box to check.
Before you figure out what’s next, you have to know what matters.
Before you make a decision, you have to know what’s non-negotiable.
Here’s the thing: your values will evolve. That’s healthy. You have to be in conversation with them—regularly, intentionally, honestly.
Reflection Prompt | Your Values Check-In
⟶ What do you want to stand for?
⟶ What are the top 3 values that guide your life and leadership today?
⟶ Where are you most aligned? Where are you off track?
Define The Legacy, Not Just The Ladder
Often, we build careers by default: the next role, the next rung, the next reward. Very few people stop to ask, Where is this ladder taking me? And is that where I’m trying to go?
Legacy isn’t something you think about at the end. It’s something you design toward.
It’s the impact you want to make. The problems you care most about solving. The story people will tell about how you showed up and what you made possible.
“…they will forget what you said, what you did, but they will never forget how you made them feel.” - Maya Angelou
When I finally allowed myself to name what I wanted, to say it out loud, it changed everything. Not just the long-term direction, but the decisions I made in the short term. I could see which experiences would stretch me, and which roles weren’t a fit, even if they looked impressive. And where I was chasing someone else’s version of success instead of my own. It took courage and the willingness to say I wanted something and work for it, something that, growing up, I would not have thought was possible.
Reflection Prompt: Design Toward Your Bold Future
⟶ What would make you proud 20 years from now?
⟶ What do you want to be known for?
⟶ If you weren’t afraid to say it out loud, what would you admit you really want?
Navigate The Messy Middle
There’s a space between clarity and action that feels like drift. It’s uncomfortable. It’s quiet. And it can feel dangerous when you’re used to being certain, decisive, and busy.
But the messy middle is where the real work happens.
It’s where you listen more than you plan.
It’s where you sit with your restlessness and ask whether it’s time to grow or time to let go.
In my experience, people often confuse:
⟶ Boredom with burnout
⟶ Being stuck with being still
⟶ Fear with unreadiness
And when leaders reach this phase, they’re often tempted to shake things up, change jobs, launch a new initiative, or take on more responsibilities. But if you move too quickly, you risk missing the signal amidst the noise.
Sometimes what’s needed isn’t a leap. It’s a deeper look. A chance to go inward.
Reflection Prompt: In The Fog? Try These Questions
⟶ What’s energizing you right now?
⟶ What are you avoiding?
⟶ What doesn’t energize you anymore?
⟶ What are you pretending not to know?
Give Yourself Permission To Evolve
You’re allowed to change your mind.
You’re allowed to grow out of goals that no longer fit.
You’re allowed to want something different now than you did five years ago.
The world will keep offering you a template: a bigger job, a faster pace, and more visibility. But you don’t have to follow it. In fact, some of the most aligned choices I’ve seen leaders make looked “smaller” from the outside, but transformational on the inside.
What’s next doesn’t have to be dramatic.
Sometimes, it’s an experiment: a stretch assignment, a sabbatical, a new conversation.
Sometimes, it’s a quiet decision to stop proving and start becoming.
Reflection Prompt: Try These Questions
Roles. What roles or identities do I want to lean into?
Rhythms. What pace and structure do I want for my life?
Relationships. Who do I want to spend more (or less) time with?
Results. What impact do I want to have?
Then ask: What’s one small next step I can take this quarter?
What’s Next Is Not A Title. It’s A Direction
This isn’t about having the perfect plan.
It’s about having the courage to ask the right questions.
It’s about honoring your values, naming your legacy, and moving forward with intention—even when the path ahead is unclear.
You don’t need to see the whole map.
Just take the next right step, grounded in self.
