The Momentum Files #77
.. Rethinking What's Next
The question isn't whether to stay or go.
It's whether the path you've been following still fits.
Over the past several months, I've been having a version of the same conversation with former clients, experienced leaders, and HR colleagues.
It usually starts with something specific. A voluntary exit package. An organizational restructuring. A leadership change. Or an opportunity that once would have been an easy yes, but now isn't.
The circumstances are different, but there's often a bigger question underneath:
Is the professional path I've been following still the right one for where I am today?
That's a different question from "Should I take the package?" or "Should I start looking?" And it's the one I think deserves more attention.
Recent workforce changes, including Microsoft's voluntary exit announcements here in the Seattle area, have brought these conversations into sharper focus.
The financial questions are real, and they matter.
A financial planner I spoke with recently mentioned how busy they've been fielding calls from professionals evaluating exit packages. And I've been hearing from professionals working through what those decisions mean for their careers.
Can I afford to leave? What would I do next? After decades of building a career, do I really want to start over? And if I stay, what am I staying for?
These aren't always easy questions, even for people who have spent their careers making difficult decisions.
When the Opportunity You Wanted No Longer Fits
I was recently talking with a client in a senior leadership role about a potential opportunity that would involve significantly greater responsibility.
A couple of years ago, this would have been exactly the kind of opportunity they wanted. They would have jumped at the chance.
Now? Not so sure.
It wasn't a question of capability or readiness. The hesitation was about the demands and trade-offs that would come with the expanded responsibility.
That led us into a different conversation.
Not whether the client could do the job, but whether they still wanted what came with it.
We're accustomed to thinking about career growth as moving up, taking on more, increasing our influence, and accepting the next big challenge.
But what if your definition of success has changed?
What if the responsibilities that once energized you now come with trade-offs you're less willing to make?
An opportunity can be a good one without being the right one for you, right now.
That doesn't mean you've lost your ambition or stopped growing. It may simply mean you're evaluating opportunities through a different lens than you were several years ago.
Worth understanding before you say yes.
Financial Readiness Isn't the Same as Professional Readiness
When an exit package is on the table, it's natural to start with the numbers.
Can I afford to leave? What happens to my benefits? How does this affect retirement? How long could I go without another paycheck?
Those questions matter. And they're best explored with a qualified financial advisor.
But being financially prepared to leave doesn't necessarily mean you're clear about what you want to do next.
I was reminded of this in another coaching conversation.
A client who had been away from the workforce for some time told me they really needed to get back to work.
My question was: What does needing to work actually mean?
Was it about earning money? Having structure? Staying engaged? Feeling productive? Having something meaningful to contribute?
As we talked, we explored both the financial and nonfinancial needs behind that statement.
And here's what made the conversation interesting: earning a professional-level salary wasn't essential.
That opened up a very different set of possibilities.
If the next opportunity didn't need to replace a previous salary, did it really need to resemble the client's former career? Could a different kind of work provide the income, engagement, and purpose they wanted?
We hadn't settled on an answer. But we were no longer assuming that returning to a familiar kind of job was the only solution.
Before you decide what to do, make sure you understand what you actually need.
There's another consideration, particularly for professionals who have spent decades building a career: identity.
When you've been known for a particular role, title, or area of expertise, imagining yourself doing something different isn't always easy.
I've explored this in a prior article titled The Identity Shift No One Talks About During Career Transitions.
Sometimes the financial decision is relatively clear. It's the professional and personal questions that take more time.
Staying Is a Decision, Too
Much of the conversation around voluntary exit packages focuses on the people considering leaving.
But what about those who stay?
Organizational changes don't stop affecting you simply because you've decided to remain.
You may be leading a larger team with fewer resources. Your responsibilities may have expanded. Priorities may have shifted while performance expectations remain unchanged.
Having spent 16 years in executive leadership, I know how quickly organizational changes can reshape what a role requires.
And I've seen how easy it is for capable leaders to absorb more responsibility without stopping to reconsider what is realistic, sustainable, or even desirable.
Staying doesn't necessarily mean continuing as before.
In fact, staying may require some of the same questions you'd ask if you were considering leaving.
Do I still want this role, given what it now requires? What would need to change for staying to be the right choice? Am I staying because this is genuinely where I want to be, or because leaving feels more complicated?
Staying deserves the same intentionality as leaving.
For some professionals, asking these questions may lead to a different conversation with their manager, a reassessment of priorities, or a new approach to leading their team.
For others, it may clarify that leaving is the right direction, even if the timing isn't right yet.
Either way, staying becomes a choice rather than simply the default.
And if the honest answer is that you're staying because leaving feels complicated rather than because staying feels right, that's worth knowing.
Are You Solving the Right Problem?
One thing I've noticed over more than 15 years of coaching is how quickly accomplished professionals move into problem-solving mode.
Someone considering an exit package begins updating their résumé. Someone thinking about retirement starts calculating dates. Someone questioning their current role begins looking at job postings.
They're taking action. But have they spent enough time understanding what they're trying to accomplish?
That's where I often challenge clients to think differently.
Are you looking for another job, or are you looking for a different professional experience?
Do you want more responsibility, or do you want more influence over the work that matters to you?
Are you ready to leave your organization, or are you ready to change something about how you're working within it?
And are you evaluating your options based on what you want today, or what you've always assumed should come next?
Sometimes we need to consider possibilities beyond the career paths we already know. I've explored this in an earlier article about creating a professional future that fits who you are today.
Your next step might be another senior leadership role. It might be consulting, advisory work, a different kind of organization, or a new balance between professional and personal priorities.
Or it might mean staying where you are, but approaching your work differently.
The point isn't to create more options just for the sake of having them. It's to make sure you're not choosing among too few.
You don't need answers to all these questions before you move forward. You do need to know which ones you've been avoiding.
One Final Thought
Whether you're considering an exit package, questioning your current role, or evaluating an opportunity that once would have been an easy yes, don't assume the next step is obvious simply because you've been successful at the last one.
Sometimes the most valuable thing you can do before making a decision is question the assumptions behind it.
So rather than asking only whether you should stay or go, consider this:
Knowing what I know today, what would I choose for myself now?
If You're Working Through a Decision Like This
You don't have to work through it alone, or figure out where to start.
I offer a complimentary Executive Career Blueprint Call, a 30-minute conversation focused on one specific professional challenge, followed by a written Blueprint plan delivered within 24 hours.
It's designed for experienced professionals at a crossroads. Not to tell you what to decide, but to help you understand what you're actually deciding and identify a useful next step.
Reserve Your Complimentary Executive Career Blueprint Call
I open a limited number of sessions each month.
Recommended Next Read
Before pursuing your next opportunity, consider whether it's a role you genuinely want or simply the next logical step in a familiar career path.