20. Redefining Retirement for the Woodstock Generation


Lately, HR Strategists have been boldly resetting their workforce horizons by listening to the Woodstock Generation’s advice to let them help redesign the details of their work for the benefit of themselves and their employer. This dynamic approach retains maturity, ensures workplace stability, increases productivity and creates a culture of comradery.

This approach takes the awkwardness out of the executive retirement discussion. It makes the succession plan come alive with many new and innovative ways to take advantage of the mature executive’s knowledge base to solve a host of workforce challenges.

This culture of comradery can take care of unexpected or temporary vacancies brought about by someone needing to take a leave of absence, an unexpected resignation, or maybe a special project can benefit greatly from the wisdom of this particular executive. These are all examples where maturity can be useful to the company.

You may be thinking that there’s no way a senior executive would ever be willing to take a lesser position, for less pay, to do the work they did years ago. How do you know that? Have you asked a potential retiree if they would like to work in a special way for the company when it’s time to move on from their current role? Probably not. You simply assume — and you know what that can do.


The succession coaching talk could go like this:

  • “The company is considering a rather bold and innovate way to deal with some workforce issues and we would like your input.”
  • “Being a senior and experienced team member, what would you think about helping us construct a plan of how to deal with unexpected resignations, leaves of absences, and special projects?”
  • “We need your insights and wisdom on how to create a role here that would help us fill those temporary vacancies with someone like yourself. Someone that has the background knowledge, flexibility, and desire to help out the company and to stay tethered to the company as they slowly move into their next phase of life.”
  • “We need your input on what this position would look like so, if you wish, you could own it for as long as you wanted too after a well-defined transition period occurs from your current situation. You would be a pioneering executive redefining our world of work”. What do you think?”

Here is what they would think with a positive mindset. “Ok the company is signaling to me that it’s time to retire, but they see me as having value. In fact, they see me as having such value they are offering me a new and innovative purpose while allowing me the time to transition from my current role. This could be good. I really do not want to stop working but I am tired of the grind and this would allow me input into what I would be doing, how much I’d be paid and I would be able to tell them when I would be available to them.”

If they have a negative mindset or they really want to do something outside of the company, you have sent the time to retire message and you move along to the transition discussion.

Either way, the executive has been given the respect they deserve — a way to stay with the company that benefits both — and the executive has been given recognition that they have value.

For other innovative thought processes regarding the idea of retirement go to www.Legacytransitions.org or contact Bob Foley at

[email protected]


If you haven’t saved enough for retirement, consider the following:

I’ve read the various surveys reporting that many Baby Boomers feel that they have not saved enough for retirement. Many say the reason is their 60’s just crept up on them and other expenses like their children’s college education, the cost of housing, and the 2008 market crash were obstacles to saving. Some even had to deal with unexpected medical expenses that soaked up all the funds they were trying to put away.

So now, as they age, the need to retire gets closer and the funds necessary to augment social security just aren’t there. This causes fear, anxiety, and helplessness. It puts many into the dark hole of denial, a place that only causes a downward spiral. Many hold on to the jobs they have and plan to stay with it as long as they can. But they know the end is in sight. 


So what can they do?


Well, just like they did in their early 20’s, it’s time to stop panicking, reflect, and get some advice. Remember when you were first starting out it in your career? It felt hopeless as you started to interview for jobs and you were terrible at it. But over time, you started to become a better interviewee and you grew your networking until you had your foot in the door.

Well, it’s time to do that again! But this time, you bring a boatload of experience, you actually can show how you can bring value to your employer, and you have the wisdom of your years to share.

If your current situation can sustain you and you like what you do, keep doing it for as long as they will have you. When your annual review comes along, have a heart to heart with your company. Tell them about how you would like to continue in your role for X years and then pull back into a consulting or a specialist role at market rate for as long as it is good for both. As long as you continue to bring high-quality value to your workplace, why wouldn’t they keep you around?

The big thing is that you have to set up a trusting relationship with your employer. The head games that you imagined disappear because you are dealing with the company upfront. You are in control. Now, if the company for some reason has to pull back on their commitment, for whatever reason, nefarious or not, you simply negotiate a good severance and do what you did in the past – network, network, network until that next opportunity appears. But before you start that networking stage, step back and reflect on what it is you really want to do, not what you can do because you’ve done it before.

Today, many people I coach feel it’s their age that is against them, when actually it is their inability to see change in their short term future. They fail to seek out the new skills necessary to bring value to what they are doing. Remember, the company does not want turnover because it’s an expense. What they want is all employees getting behind the vision, and you bringing value that will sustain said vision.

In order to reenter the workforce, decide what you really want to do. Research the long term value skills necessary to do that job. Make sure you have those new skills. Or, if not, go back to school or get a certification in order to show your potential employer that you are relevant and you can bring big value and wisdom to their workplace.

But in choosing this new workplace, it’s not only about skills. It’s also about how the place feels and what their corporate values look like. When you check out their website, can you see yourself on that site a year from now? In other words, are you representative of their culture. 

Now, there are also alternatives to joining “the man” again. In deciding what you want to do, you should also check out other ways of generating revenue for Y-O-U!

Are you ready, willing, and able to be an entrepreneur? Ok then go talk to several Business Brokers to see what opportunities they have. Or, if what you are looking for isn’t for sale, seek out a Franchise Coach. They can show you the various franchises that may appeal to you.

If you have the “knack” to run your own business successfully, the entrepreneur track can help relieve the long term stability fear and set you up on a 20 year “revenue for me stream,” working as much or as little as you want. There are also significant 401k savings rules that are available to you as an “entrepreneur” that are not there as an “employee,” on top of your “revenue stream for me.”

Finally, on top of deciding what you want to do and finding it, you need to take care of yourself physically. You need to understand that it is all about “Intake.” It’s about what you eat, how often you exercise, and regular visits with medical personnel to bring surety to the way you look and feel.

If you are in the lacking position we spoke of in the beginning of this piece, stop, reflect, and take action. You are in control of your life — just give yourself the chance to do it right. And if you need some advice or help, you can reach me at [email protected]

Your future is as bright or as bleak as you make it. Just give yourself the chance to decide what you want and then go for it.