6 Signs That It’s Time to Move On

Deciding when to move on – that it’s time to retire, shift into an encore career, or otherwise leave your leadership role – and head toward life’s next chapter may be the most challenging decision of your career. Some leaders make this decision easily and move forward gracefully. Others delay, postpone, and defer until circumstances take over. They hang on too long until the “it’s time to leave” signals become so blindingly obvious that they can no longer be avoided. Still other executives never seem to get the message and have to be subtly, or sometimes not so subtly, forced out of their positions. This article covers six classic signs that it might be time to prepare your exit plan.

Leading well includes leaving well, and that means taking charge of your exit and leaving on a high note. Choosing how to exit your role may be the ultimate act of leadership. The first step is determining when it’s time to move on.

Unless the change is thrust upon us, choosing when and how to move toward life’s next chapter involves satisfying both the head and the heart. The head needs a plan. The heart needs time to process, to come to terms with the change. It may also require some courage – the courage to act, to disrupt the status quo. Courage to leave the safe harbor of the present and step into the unknown.

Planning your move can be similar to strategic planning or strategizing a new initiative. It’s a process of assessing the current landscape, exploring options, making sense of your choices, creating a vision for what’s next, and developing a strategy to pursue your vision.

Processing your plan and options with your spouse, your colleagues, or your business coach can begin to satisfy the heart. You have to get comfortable with the fact that change is coming.

Career paths – and much of life, for that matter – rarely take a straight line. As you consider what’s next, make room for serendipity. Your insights about which path to take next might come from unexpected places, but you have to be open to the message.

If you’ve always had a clear departure date in mind, that’s great. For retiring executives, the question of timing is often made easier because of age- or date-related milestones, e.g., turning 65 or an organization anniversary date. A recent report found that for 39% of current retirees, reaching a certain age was their move-on threshold. (Interestingly, only 7% said it was triggered by having saved a specific amount of money.)[i]

Choosing to move on involves the head and the heart.
The head needs a plan. The heart needs time to process.

For others, the decision may involve a triggering event, such as a change in health status or a change in life circumstances, like the need to become a caregiver. But for many of us, the decision involves a gradual sorting-out process.

Initially, the time-to-move-on signals can be relatively weak, but eventually, you’ll sense they’re building in intensity. Much like the end of a long relationship, it often doesn’t happen instantly, but may involve a recognition growing over time that change is needed. As one recently retired executive told me, “I noticed that my work life is a bit like a Ferris Wheel, with two- to three-year cycles tied to our strategic plan. I recognized that if I didn’t get off the next time we reached the platform, I was signing on for another cycle.”

Whether your decision is based on approaching a specific date, a change in life’s circumstances, or a growing realization, the heart may not be ready to let you out of the woods just yet. For the past 20 years, I’ve watched a great many executives approach this decision, almost all with some degree of ambivalence, even those who had an anchor date firmly in mind. With any change, some level of uncertainty comes with the territory. Facing doubts (and fears) can be easier if you have a desirable project or circumstance waiting for you on the other side of the threshold – it’s easier if you have a magnetic project pulling you forward rather than a feeling of being pushed out of your role. The healthiest transitions are those that focus on moving forward – looking toward new aspirations rather than looking back at job or role that you’re leaving behind.

The healthiest transitions focus on moving forward –
toward new aspirations, not what you’re leaving behind.

Deciding to leave not only stirs our emotions, but it can also magnify our regrets about the unfinished business that every leader has on his or her horizon. (After all, what is a leader for but to shape the future?) Don’t let the “woulda-shoulda-coulda” voice in your head grow out of proportion. This is the time to focus on what you’ve accomplished, and more importantly, what’s on the road ahead.

So, how do you know when it’s time to move on? Here are the top six signs I’ve seen in my work with departing executives.

  1. Do you dread going to work? Are you waking up most mornings with some part of you dreading going to work? When you think about work, what percentage of those thoughts fills you with joy versus anxiety or boredom? If you’ve grown tired of the role, don’t let your feelings of obligation to your organization override the need to take care of your own health and happiness – and your stewardship of the organization.Even on days when your internal voice of discontent isn’t that loud, you can’t hide your true feelings for long. As the leader, your mood and outlook have a significant effect on your group’s vibe. Your pent-up dissatisfaction is bound to manifest in different ways, and will eventually have a negative impact on your team and possibly your organization.
  2. Is your energy or attention drawn elsewhere? What percentage of the time do you find yourself fantasizing about what’s next as opposed to dealing with matters at hand? Has that urge to see the world become more appealing (and feasible)? Have your family demands changed? Are you being called to care for aging parents, an ill spouse, or other family members in need? Or do you find yourself increasingly drawn toward your volunteer roles or spending time with your grandchildren?The urge to contribute, to be generative, is important throughout adulthood, but later in life, the focus of our generativity often shifts from career pursuits to other aspects of our lives. The key is not to let our wandering interests lead to on-the-job disengagement. If your interests are wandering, it may be time to follow them.
  3. Are you getting signals that you no longer fit the role? Are you sensing that there’s a growing gap between the leadership needs of the organization and what you’re interested in providing or able to provide? Deep inside, do you know that the job has grown beyond your capacity – or maybe just your interest – to manage it effectively?This doesn’t necessarily have to do with your abilities as a leader. It could simply be that you no longer have the drive to deal with the demands of your position. It may be a matter of appetite, not capacity. If you and your job have grown apart, it isn’t a character flaw. However, sticking around too long might be.
  4. Are you at odds with your board over the big stuff? Do you see a widening gap between yourself and your board about major factors, such as the direction of your organization? Are your vision or professional values starting to clash?Boards and executives sometimes grow apart. Changes in board leadership can have, shall we say, unexpected consequences. Don’t blame yourself for the differences. But denying changes in your organization, especially those that don’t line up with your values, can have a disheartening effect. If you can’t change the circumstances, you might need to change the venue – and move on.
  5. Is your job making you sick? Has your health changed significantly in recent months or years? Maybe this is your body’s way of telling you that you need a change of pace. If you’re holding in a lot of stress or feeling a lot of inner conflict about your role as a leader, that discomfort could eventually impact your well-being.
  6. In your heart, do you know it’s time? Can you afford to retire? Are there other interests or other parts of your personality yearning to be expressed? Has the benefit of moving on exceeded that of staying put? You’re more than your role, and you know it. Make sure the world knows it, too. Maybe it’s time to strut your stuff elsewhere.

If you answered “yes” to several of the six questions, you’re probably ready to move on. Now, take a deep breath and give yourself permission to take the leap.

Getting a read on your situation

For many of us, in the rush and crush of our daily responsibilities, it’s easy to ignore signals until they become blatantly obvious. Poet Robert Burns wrote, “O would some power to give us the gift to see ourselves as others see us.”[ii] Often those close to us see the need for change before we do. Are family members or colleagues suggesting it’s time for a change? When you’re out for a walk, what is your inner wisdom telling you?

Now it’s a matter of timing

Beyond readiness, the choice of when and how to move on is also a matter of timing—personal, professional, and organizational.

  • Personal timing – Are you financially, emotionally, and socially ready to move on? Financially – have you reviewed the financial implications? Emotionally – have you considered how much of your identity is wrapped up in your current role, and have you considered how to supplant that in your future role or post-career life? Socially – how will moving on affect your family, especially the members of your family who rely on you for financial support? Is your spouse supportive of your decision to transition out of your current job? If you’re retiring, have you built a social network outside of your work?
  • Professional timing – Is there something else you want to accomplish in your current role that’s really important to you that you want to put on the agenda before you leave? And is your current role the best platform to accomplish that goal, or is this a potential project for your next chapter?
  • Organizational timing You will also need to consider how the organization will handle your departure. Are your people ready to step up to the plate when your organization transitions to a new executive? The less prepared your organization is for a leadership shift of this magnitude, the more advance notice you should offer. There’s never a perfect time to leave, but some times are better than others. A major contract renewal or completion of a capital campaign might be among the good reasons to delay your departure. On the other hand, initiatives better left to your successor, such as a major expansion, might be a reason to accelerate your departure plans.

Choosing versus deciding

Determining when to move on involves both choices and decisions. Decisions are made by the head, and tend to be supported by facts. Choices are more often made by the heart, based on impressions and feelings rather than hard data. You can decide if you have enough financial resources to retire by checking the facts – looking at your estimated Social Security payout, projecting the draw-down on savings over the years you expect to live, and so on. Based on these facts, you can make a decision about whether you’re financially prepared to retire.

Choosing to move on is underpinned by decisions about personal, professional, and organizational readiness, but when it comes right down to it, it’s a choice – a choice based on your assessment of where you are and your readiness to move on, a choice supported by the head and made by the heart.

A graceful exit builds towards a conclusion that
feels natural, with the head and the heart aligned.

A graceful exit builds towards a conclusion that feels natural, with the head and the heart aligned. There’s no such thing as perfect timing, or perfect conditions to move on. But there is a leaderful way to approach it, and that begins with recognizing that it’s time to move on and having the courage to step toward what’s next.

Do you think it’s time to move on to life’s next chapter? See the signup box on the right for a free eBook on how to take charge of your exit and make the most of this leadership change – for yourself and your organization.


[i]           Collinson, C. 2015. The Current State of Retirement: Pre-Retiree’s Expectations and Retiree Realities. Transamerica Center for Retirement Studies. www.transamericacenter.org/retirement-research/retiree-survey.

[ii]           Burns, R. 1786. “For a Louse,” verse 8. English translation from the Scottish dialect. www.robertburns.org/works/97.shtml.