Last week, I attended a three-day conference. Between conference sessions, evening events, client meetings, hallway conversations, coffee chats, and dinners, I talked to a lot of people.
Some were early in their careers trying to figure out what came next.
Some were seasoned leaders carrying the weight of growing firms and developing future leaders.
Some were thinking about retirement.
Some were considering starting businesses.
Others were wondering if it was finally time to leave a role they had outgrown.
What struck me wasn’t how different they were. It was how similar many of their conversations sounded.
One theme kept surfacing. People felt stuck. Not unsuccessful. Not unhappy. Not incapable. Just stuck.
As I listened, I found myself reflecting on my own career.
I know what burnout feels like.
I know what it’s like to wake up on Monday morning already exhausted by the week ahead.
I know how draining it can be to sit in a role you’ve outgrown. To feel capable of more but unable to fully use your strengths. To find yourself increasingly disconnected from the work, the leadership, or the direction of the organization.
I’ve experienced what it’s like when your values no longer align with company priorities. When you don’t have the support or resources needed to be successful. When you’re carrying responsibility without the authority to create change.
I’ve stayed too long at jobs.
I’ve also watched opportunities pass by and wondered what might have happened if I had acted sooner.
One crossroads in particular stands out.
In early 2025, I was wrestling with a decision. Should I look for another job? Or should I finally take the leap and start my own company?
Like many people facing a major career decision, I sought advice. I was hoping someone would tell me what to do.
Instead, one very wise person asked me a single question: “Would you regret not doing it?”
The answer came immediately. Yes! I would.
Ivi Gabales Consulting was born the next day.
Looking back, that conversation taught me something important.
Most people aren’t stuck because they lack options. They’re stuck because they lack clarity.
And that’s where I believe leaders need to pay attention. Because what I heard at that conference wasn’t just a collection of personal career challenges. It was a leadership challenge.
Every leader has people on their team who feel stuck. The high performer who has outgrown their role. The emerging leader who wants more responsibility but doesn’t know how to ask for it. The experienced professional who feels disconnected from the organization’s direction. The employee who stopped raising their hand because nobody seemed to listen.
When people feel stuck long enough, something happens. They stop growing. Then they stop engaging. Eventually, they leave.
Sometimes physically. Sometimes mentally long before they submit a resignation letter.
As leaders, we spend a lot of time talking about retention, engagement, succession planning, culture, and talent development. But underneath all of those conversations is a simpler question: Do our people feel like they are growing?
Because growth creates energy. Growth creates engagement. Growth creates optimism. And growth creates loyalty.
The opposite is also true. When growth stops, people begin looking elsewhere for it.
The same principle applies to organizations.
I’ve met firms that were stuck in old ways of thinking, old business models, old markets, and old assumptions about what made them successful. Just like people, organizations can outgrow the strategies that got them where they are.
The challenge is that growth often requires discomfort. A difficult conversation. A leadership change. A new market. A new service. A new way of thinking. Most meaningful growth comes with uncertainty attached.
That’s why one of my favorite questions remains the same one that changed my own career: Would you regret not doing it?
It’s a powerful question for individuals. But it’s equally powerful for leaders.
Would you regret not investing in your people?
Would you regret not addressing the culture issue everyone sees but nobody talks about?
Would you regret not developing your next generation of leaders?
Would you regret not pursuing the opportunity that could transform your business?
Sometimes clarity doesn’t arrive in the form of an answer. Sometimes it arrives in the form of a question.
And the leaders who ask the right questions often unlock growth not only for themselves, but for the people around them.
If there is one takeaway from all those conversations last week, it’s this: Pay attention to the people who seem stuck. Including yourself.
Because being stuck is often not a sign that something is wrong. It’s a sign that growth is trying to happen.
The question is whether you’ll recognize it before the opportunity passes by.
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Each week, I explore the intersection of leadership, business development, relationships, and trust. The conversations that happen before the proposal, before the promotion, and before the opportunity often determine what happens after.
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