Do I Need a Plan for the Rest of My Life?

by Dennis Blank

Every article or book on retirement says you must. I was committed to staying at my job until I had one. But then I began to see that I might be stuck at my desk at 75, still trying to come up with one.

Back when the media business was thriving I used to really look forward to the annual sales meeting. It was always someplace nice: Lyford Cay, Aspen, Ireland, Palm Beach or Puerto Rico. Late in my career, after most of my contemporaries had left, I didn’t look forward to these events the same way, but through the ’80s and ’90s they still had a “pinch me” quality to them. 

“OK, so I don’t have to work this week and you’re going to fly me to Arizona and put me up in a five-star hotel, feed me four times a day, pick up my greens fees and then pummel me with alcohol and music all night long? And in return I have to be in my chair in the meeting room from 8:00 a.m. until noon every day, although I don’t really have to pretend to be anything close to 100%—is that about it?” I could do that. I still could if someone would make me the offer.

There was a lot of ritual associated with these events, and the longer one worked there the more responsible one became for upholding, embellishing and perpetuating it. Of all the sales meeting rituals, my favorite was a recurring event in the late ’80s. One of our guys was an accomplished public speaker who could step up onto a stage and be smart and entertaining for 15 minutes without any real preparation. Each year the publisher would call him to the podium to make a few comments. It was always late enough so that the crowd was well oiled—but never so late that inhibitions were too low, or sensitivities too high.

By this point in the meeting we’d had hours of indoctrination on the plan for the upcoming year. So our speaker would be asked to make a few remarks on how we were doing against the current plan. He’d begin by complementing the magazine’s management on the brilliance of the new plan, and would then tick off a dozen or so of the most absurd and perplexing management moves of the past year, assuring us these events had always been a part of some larger management vision that we mortals were only just barely able to comprehend. It was hilarious.

By the time he finished we’d be in tears, and we’d be bonded in the knowledge that even the bosses knew the truth of the matter, that while it is all well and good to have a plan, the unexpected is going to happen along the way. Some of it will make you laugh, and some of it will make you cry, but most of it will not be what you expected or what you planned for. As the saying goes: If you want to make God laugh, make a plan.

Every article or book on the subject of retirement says emphatically that you must have a plan in order to have a successful retirement. I’m sure it’s so. In fact, at one point I was committed to continuing at my job until I had a plan in place. But then I began to contemplate the possibility that I might still be stuck at my desk at 75, trying to come up with one. 

So I quit. But the rock and hard place I find myself wedged between are the idea that I need a plan for the rest of my life, and the conviction that it is a folly to create one.

So, Coach Lou, should I even bother? Life is so unpredictable, what is the point of agonizing over a plan? Why shouldn’t I just wing it?

Your pal, d


Coach Lou responds...


Dear d, 

Well it is apparent that you are in a bit of a pickle. Now how do we get you out of the barrel?

The validity in the books is that having “a plan” is always a good idea, but it isn’t a business plan. The variables, as a retired person, are certainly fewer. Your plan might be more about who you want to “be” rather than what you want to “do.”

It is obvious that you are still harboring some nostalgia for the good ol’ days, and rightly so. You spent 30 years at Jumbo Corp. carving out a reputation, making a living and having some fun while doing it. While that comes with its own complications, it also gave you identity and community. Those are pretty powerful things to change or lose.

I want you to relish how you have spent the first two thirds of your life. Take the time to reflect on what you have created. That is by no means a trivial matter. You will see that all you learned along the way will now serve what you choose for the next part of your life. 

Let’s not think of this as a plan, but a journey. First thing I want you to do is create a two-column list. In the left column, list all of the skills you have gained over the past 30 years (good golfer and connoisseur of fine whiskey counts). In the right column, list those items in the first column that you truly enjoy and won’t give up. We’ll check in on that in a later post.

In the meantime, just relish the good fortune of this dilemma, which is bringing two good friends together again to frustrate, entertain and support each other. Just like when we were kids.

Coach Lou


Coach Lou is a co-founder of Chain Reaction Partners, an executive and leadership training consultancy in Boulder, Colo. d’blank is the author of The Daily Blank blog.

by Dennis Blank | Saturday, March 20, 2010 | Career Change, Dream Careers, Hiring a Life Coach

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