It doesn’t have to be like this. We often find ourselves at a career crossroads, much like a client of mine, an Executive Director leading an organization poised for significant growth. The question looms: is she ready to steer this expanded ship? Her honest answer? Uncertainty.
To help her visualize her path, I posed a question: “Imagine an Etch-A-Sketch. Wipe away your current organization. Now, draw me your ideal next role. Could that role exist within this evolving organization?” Her response was twofold: “(1) I have no idea and (2) I really haven’t given it any thought.”
This moment of pause isn’t unique to her. It highlights a common challenge for many professionals: recognizing when it’s time to leave a job. It’s not always a clear-cut decision, and it’s certainly more nuanced than simply escaping burnout.
My own journey with GLAAD offers some perspective. After eight fulfilling years, I decided against renewing my contract, a full nine months before it was set to expire. This wasn’t a rash decision, but one driven by several key factors.
WHY I LEFT GLAAD: My Personal Crossroads
My decision to leave GLAAD wasn’t born of dissatisfaction, but of evolving priorities and a clear vision for the future – both for myself and the organization. Three main reasons crystallized my choice:
-
Family First. My family became the undeniable focal point. A growing sense of responsibility towards my partner and children weighed heavily on me. How could I passionately advocate for an entire marginalized community while feeling like I was falling short for my own kids navigating the complexities of adolescence? This internal conflict became impossible to ignore. My commitment to family was signaling it was time for a shift.
-
The Future Was Already in Sight. This isn’t about having a designated successor waiting in the wings – in fact, my replacement was an external hire. It’s about recognizing the burgeoning talent within the organization and understanding when it’s time to empower the next generation.
[alt]: Joan Garry in a meeting, discussing with team members, illustrating leadership and succession planning.
I vividly recall a pivotal meeting. As I wrestled with my decision, a staff member eagerly introduced me to a candidate for an open position on her team, someone she believed was exceptional. The three of us sat together, and it was immediately apparent – he was a rock star. And so was she, the staff member who brought him in. The conversation was dynamic, insightful, and I found myself learning from both of them.
In that moment, clarity struck. I wasn’t just confident in passing the baton to individuals like them; I realized I should. The future of the organization was bright, and it was time for fresh leadership to guide it.
- Mission Accomplished, No Regrets. I had achieved what I set out to do at GLAAD. We had collectively rebuilt the organization, launching impactful programs and campaigns that made a tangible difference. I firmly believed two things: first, that fresh perspectives are invaluable for any organization’s continued growth, and second, that GLAAD’s future strategy, particularly in the rapidly evolving media landscape, might be better shaped and executed by someone with a different, perhaps more future-oriented skillset than my own. I left knowing I had contributed significantly and that the organization was ready for its next chapter.
That’s my story. But what about you? What are the signals to watch for in your own career? How should you approach thinking about your professional future and knowing when “This Is Where I Leave You” becomes the right decision?
IS IT TIME TO PLAN YOUR EXIT STRATEGY? Key Questions to Ask Yourself
Reflect on the following questions. Your honest answers can illuminate whether it’s time to consider your exit strategy.
-
Are you still learning and growing? People thrive in roles long-term for two reasons. The healthy reason: the job evolves, offering new challenges and opportunities for growth. You’re constantly stretching and developing new skills. The unhealthy reason can be summed up in one word: inertia. Are you actively learning, or are you simply comfortable?
-
Do you frequently find yourself saying, “That’s not how we do it here?” or “We tried that before and it didn’t work?” Resistance to new ideas and a reliance on past practices can be a major red flag. Inability to envision or embrace new approaches is a strong indicator of stagnation, both for you and potentially for your organization. If innovation feels foreign, it’s time to introspect.
-
Is your passion for work overshadowing your passion for family? This is a crucial question that demands input beyond your own perspective. Engage your family in this conversation. Has ‘saving the world’ begun to consistently outweigh important family moments – school plays, family dinners, even seemingly minor occasions? It’s possible your family has been signaling their feelings about your work-life balance, and it’s time to listen.
-
Are you primarily concerned about who will replace you? Let’s be direct. This concern often masks deeper issues: inertia and fear of the unknown next step for yourself. Worrying about your successor can be a convenient distraction. Remove this worry from your decision-making process. Holding on for this reason will likely lead to overstaying your welcome and hindering both your own growth and the organization’s progress.
-
Are you experiencing burnout? Please, don’t let burnout be the defining factor that forces your departure. Burnout is detrimental to you and sets a negative example. Remember, others are observing. Leadership roles need to be perceived as sustainable to attract high-caliber candidates. Burnout can breed resentment towards the very organization you care about. And importantly, recognize that burnout is often self-imposed. Take responsibility and don’t place blame elsewhere.
[alt]: A person looking stressed and overwhelmed at their desk, symbolizing burnout and the need for career reflection.
- Ask yourself the most challenging question: Are you staying simply because you lack a vision for what’s next? This is perhaps the least justifiable reason to stay. It’s a decision rooted in personal fear, not in the best interests of the organization. Staying because of uncertainty about your future is a disservice to both yourself and your organization.
I’m not advocating for impulsive job abandonment. However, I urge leaders to be proactive, honest with themselves, cultivate leadership within their organizations, and develop a preliminary exit strategy.
People invest significant thought into job searches – meticulously seeking roles that align with their skills and aspirations.
Why not apply the same thoughtfulness to recognizing when it’s time to transition out of a role?
As a leader, you’ve dedicated immense effort, passion, and commitment to your organization’s mission. It’s essential to evaluate your own tenure with the same critical and strategic lens.
WHAT NEXT? Taking Action After “This Is Where I Leave You”
Firstly, if you know someone grappling with these very questions, feeling burned out and uncertain about their future, share this article. It might offer valuable guidance and validation.
Finally, if you haven’t already, subscribe to receive more leadership insights and advice like this. You can click the link here. Thank you for reading.
