Five Barriers Between You and Your Life’s Next Chapter

Unless you’ve been living under a rock, it’s been impossible to avoid the media stories about the massive wave of baby boomers heading towards retirement. But underlying these stories are some striking facts that signal a major change in leadership in enterprises and institutions throughout the country. The median age for an S&P 500 CEO is 55. Three-fifths of senior federal executives are, or shortly will be, eligible for retirement. And, it’s estimated that two-thirds of our nation’s nonprofit leaders are age 60 or older.

As these leaders head towards the traditional retirement threshold, the situations and opportunities they face are dramatically different than those faced by any previous generation. For a host of reasons, traditional retirement is not the choice of many Boomers, nonprofit leaders included. Here are a few of those reasons:

  • Americans are living longer, and living in better health for longer.
  • The recent financial crisis and slow road to recovery have forced many to postpone the retirement decision.
  • Many love their work and don’t want to leave it.

Even so, many older leaders are more than ready to move into their next act. They want the freedom that they’ve been promised all these years, whether that’s the full-stop exit from the workforce of traditional retirement or a more improvisational, creatively constructed alternative. They want to move on, but many see barriers instead of pathways. This article looks at five common barriers and explores strategies to overcome them.

Barrier Buster #1: Ignore the myths and messages about age.

For years we’ve all been bombarded with the idea that retirement begins at 65, and that it means completely dropping out of the workforce. But when 65 was established as the retirement age for America’s earliest pension plans, it was based on the fact that life expectancy wasn’t much older than 65, if that. Social Security further cemented 65 as the “normal retirement” age by adopting it as the age at which one could draw full Social Security benefits (although Congress has bumped up the elegibility age slightly in recent years). Given changes in life expectancy, the reality is that your 65 is not at all like your parents’ 65, and it’s certainly not like your grandparents’ 65. Someone turning 65 today should be planning for at least another two decades of a very active life. (But, as they say, individual results may vary.) So, if you’re in your mid-60s, put your planning hat on. You have at least two decades to design, if not more.

What do you want to do with those “bonus years”? Thinking about your life as a portfolio may help you determine “what’s next” for you.

Barrier Buster #2: Re-balance your life portfolio.

Based on research and interviews with retired leaders, the folks who are happiest in post-career life are those who:

  1. Are in relatively good health and are paying attention to their well-being;
  2. Are involved in activities that connect them to the world in a significant way (something that is meaningful to them);
  3. Have meaningful contact with their social circle (people to whom they matter and who matter to them);
  4. Are in alignment with their spouse or significant other on finances, retirement goals, priorities, and their life together; and
  5. Have enough money for a reasonable level of financial security.

In short, they have successfully transitioned their portfolio of activities and concerns from career to post-career life.

David Corbett, the author of Portfolio Life, notes that as we go through life, we’re constantly rebalancing our life portfolio, with different elements naturally receiving different priority as we move from one stage to the next. For example, we might emphasize vocation earlier in life and family as we begin to have children. In his model, as we move toward post-career life, just as we rebalance our financial portfolio, we should also rebalance our life portfolio.

What does this mean for the exiting leader? Many executives tell me they don’t know what they would do in retirement. They say that much of their life’s meaning is tied up in their work; many of their friends are work-related, and even their avocations are linked to their profession. If you think preparing for post-career life is all about finances, think again. Look at the other four “success factors” outlined above. What can you start to do, right now, to build or expand those parts of your life portfolio?

Fear about income during retirement is often a specific and substantial barrier. As you assess the income element of your portfolio, analyze the messages that you’ve received about financial security. Many in the financial services industry say we should have resources sufficient to replace 80 percent of current income, while other sources say 40 to 50 percent is probably closer to reality, and more doable for many people. Consult a financial advisor to figure out what number works for you. Once you’ve determined your probable post-career income number, give it a trial run. Set that as your budget for the next 90 days or so.

That brings us to the nature of work after retirement. Retiring doesn’t have to mean the end of work – unless that’s what you want.

Barrier Buster #3: Get real about work after 65.

For many Boomers, the traditional “golden years” view of retirement – a time of endless leisure – is an archaic (and, maybe, even unpleasant) notion. Eight out of ten Boomers say that they plan to work at least part-time during their retirement years. Among nonprofit leaders, the numbers are higher. In a recent report, 95 percent of nonprofit executives rejected the “golden years” vision of retirement, and 60 percent said they plan to work full-time until age 70.

Some Boomers will continue to work due to lack of sufficient income to cover basic retirement expenditures and health care costs. According to the Urban Institute, about four out of ten will need to continue to work. If you’re in this boat, you won’t be alone, and you won’t be venturing into new territory. According to the same report, this is actually not much different from the financial position most Boomers’ parents were in upon their retirement.

For these reasons, bridge employment and encore careers are rapidly becoming the new norm. Mark Freedman, author and CEO of, lays out three typical approaches to an encore career:

  • Career recyclers– those who take skills and experience from one field and apply them to the next, such as a salesperson who becomes a director of development for a nonprofit organization.
  • Career changers– those who make a fresh start in a completely unrelated field, perhaps returning to school for new skills or credentials.
  • Career makers– those who take a lifelong interest and turn it into a job, perhaps converting a hobby or avocation into a busi

Retirement needn’t be an “on-off switch.” You may choose a phased retirement, shifting gradually into “what’s next.”

Essentially, phased retirement is an arrangement to continue working for your current employer, typically with a reduced workload as a transition from full-time work to full-time retirement. These arrangements may also involve part-time work, seasonal work, temporary work, or job sharing. Such arrangements may be win-win. They can benefit you by providing a higher income than what you might earn performing similar activities for another employer. Meanwhile, they help your employer by preserving needed skills and organizational memory while reducing training and onboarding costs.

But there are limitations to this approach. First, for phased retirement to work, it has to work for your successor. You don’t want to cast a shadow or clutter your successor’s leadership path. In this regard, chemistry can be a huge factor. Success often hinges on the personalities of the departing and arriving leaders. As the departing executive, you need to give space for the successor to assume leadership. This may mean working off-site for a significant period of time, perhaps permanently. You should also set up a neutral process to assess if the arrangement is working, and you must be willing to move on if it’s not.

As ready as you may be, your organization may not be ready for you to leave. That’s where the next step is critical.

Barrier Buster #4: Prepare your organization.

I frequently hear, “My organization is not ready for me to move on,” and its close cousin, “I’ll be ready to move on after (fill in the blank).” Certainly some times are better than others for a leadership transition to take place. Of course, you wouldn’t want to announce a transition when you’re in the middle of a substantial expansion project or when a major contract renewal is looming. But every organization and executive I’ve worked with always has “one more thing” on the agenda. The question to ask yourself is whether the timing for that one more thing is critical, or if that one more thing is crucial to fulfilling the promise of your tenure as the leader. More often, it’s just a good excuse for avoiding the scary prospect of “what’s next.”

As you head towards your next chapter of life, you have three essential tasks: continue to lead the organization, prepare the organization for the transition, and create a plan for the post-career phase of your life. With over 20 years of advising leaders on succession and transition, I’ve learned that it’s virtually impossible for an executive to move on if they don’t have something that they’re moving toward and are excited about the prospects they’ve created for themselves. If you’re serious about a well-planned departure, you need to invest your energy in all three tasks – leading, preparing the organization, and planning the next great phase of your life.

There may be one remaining barrier between you and moving ahead: fear. You need to grapple with uncertainty in order to ready yourself and the organization for the transition.

Barrier Buster #5: Overcome your fear of the unknown.

The familiarity of day-to-day routines helps many of us feel safe and grounded. Shaking up those routines shakes us up as well. Unfortunately, that fear can thwart actions we know we must take. The solution is a good, solid game plan that mitigates this concern — a solid exit strategy that prepares you and your organization for life’s next chapter.

Finally, we encourage you to take full responsibility for your own “what’s next” question and sort out the right time to move on, and in a way that works for you and your organization. Unfortunately, over the past 20 years, I’ve seen numerous examples of executives who did not take on the full mantle of this responsibility. Sadly, some became stale in the saddle, and the board or upper management stepped in to answer the “what’s next” question for them. You don’t want to be there. Leading well eventually includes leaving well, so plan your exit while you’re still on top.


Corbett, D. D., & Higgins, R. (2007). Portfolio Life: The New Path to Work, Purpose, and Passion After 50. San Francisco, CA: Jossey-Bass.

Favreault, M. M., Johnson, R. W., Smith, K. E., & Zedlewski, S. R. (2012). Boomers’ Retirement Income Prospects. Washington, DC: Urban Institute.

Freedman, M. (2007). Encore: Finding Work That Matters In The Second Half of Life (1st ed.). New York: PublicAffairs.

Kunreuther, F., Segal, P., & Clohsey, S. (2012). The New Lifecycle of Work – Long-Term Nonprofit Leaders Prepare for the Future. New York, NY: Building Movement Project.

Rein, L. (August 26, 2013). “Wave of retirements hitting federal workforce,” Washington Post. Retrieved from