How To Retire? ‘Declare Victory And Find Out What Else Is In You’

I loved my 40-year career in corporate America. Loved it. I started at the very lowest pay grade and made it to CEO.

Then, at 61, sooner than I thought, it was time to retire.

My dad always told me to be careful what I asked for. I certainly asked to become a CEO. I am not sure I knew what all came with that title. In my case, it consumed almost all of my time and energy. Stimulating and rewarding as the CEO job was, it felt like I was holding onto the tail of a galloping horse.

I had travelled all of my life and during long stints at Allstate Insurance and Reliance National. But travel was on another level during my 11 years at Zurich Financial Services, including my last job as CEO/President of their Zurich Middle Markets Insurance Company—through 9/11, the financial meltdown of 2008, the Katrina hurricane and more. We had offices all over the country. We had a need to travel overseas to Switzerland and elsewhere. I was always on a plane.

Just to add to the complexity of my life at that time, I had a big-time bout with cancer, requiring surgery and 45 rounds of radiation. Thankfully, it saved my life and I am still around some 20 years later.

Politically we had two notable events during my tenure, too: A change of our worldwide CEO and a significant engagement with an outside consulting firm. Both shifted the direction of our organization. It was absolutely for the better of the company, but not as good for those of us who might have been seen as legacy leaders. It led to me deciding to retire a year earlier than my long-held goal for holding off until age 62.

Now What?

Most of the CEOs I have known are just too darn busy to give much time to thinking through how they will shape their retirements. In fact, most don’t need to do much planning. They will stop working day-in, day-out, become “Of Counsel” or move on to a board position, never physically move (except for the winter home in Florida) and continue their lives happily, with more time and much less responsibility. Life will be good.

I was lucky—I had the time to think it through more deeply. There was a period between when I announced my retirement and when actually left that allowed for serious consideration about what would come next—what I wanted to come next.

I know that will not be possible for some of you. Often, a busy-to-the-end CEO will need to actually retire before they can find the time to do the planning. Whatever your situation, I urge you to put yourself first and find time as soon as practical.

Some of the planning I did by myself. Some I did with my wife. Together, we decided to find out what else we had in us. I would not seek another position in the industry. I would not accept any of the offers that came my way. After 40 years, I felt fulfilled in my corporate career, so I declared victory and we moved on to shape our life around exactly what we wanted to do.

A 10-Point Plan

We moved to Hawaii. How we came to that decision is in two of the three books I’ve written on the subject of retirement. I am a process-driven guy, so I invented a simple framework that focused us on 10 things we each wanted during the next phase of our lives.

Your list will be different, but here is ours:

1. We wanted to be warm 365 days of the year, warm enough to be outside for a walk without a jacket.
2. We wanted to be within a 30-minute drive to a good airport.
3. A warm, tropical ocean needed to be no more than 15 minutes from our house.
4. We need a Costco, Walmart or other adequate shopping within a 30-minute drive.
5. We decided to simplify our life significantly. No second home, just a single one-story house. We got rid of stuff we did not use.
6. We would exercise, run/walk/swim, stretch and lift light weights on a disciplined schedule.
7. We would find and develop a diverse set of friends and neighbors. The diversity choice was intentional, based on the fact that my older friends were starting to fade or pass. I am very thankful for the younger, stronger, talented friends that have become part of my life. Never thought I might need their help, but, as I age, I do. And they are there for us. And they have widened our view of people and cultures.
8. We needed easy access to great healthcare. To be honest, we do not have that where we live, but can get to it quickly on Oahu, about 45 minutes away by plane. We live on the Big Island of Hawaii where health care is not great. We recognize that as a significant downside to our plan. No plan is perfect.
9. We would pursue the things that had interested us for all of our lives, but that we had never had time to pursue: photography, writing, travel, my bad golf game.
10. We decided to front-load our retirement with some very adventurous things we had always wanted to do while we were still young enough to do them safely (my wife was 59 at the time we retired). I wrote a book on that called The Geezer’s Guide to Adventure. We have learned to push our physical limits and have fun succeeding and failing in the things we attempt.

Some of those adventures would cause you to question our sanity—swimming with salt-water crocodiles with no protection comes to mind. So does my recent swim next to a dead sperm whale that was being eaten by some of the largest sharks in the ocean. And then there are our frequent lava adventures.

Our retirement years have been our risk-taking, “let’s see if we can do this safely” years and we love that part of our lives.

‘Zero Fear of Retirement’

When we added all of those up, they led us to Hawaii. We have a long family history with the Big Island, so the choice was easy. We rented for six months to make sure our decision was a good one, a “try before you buy” time.

It was everything we had hoped it would be. We are still here nearly 20 years later. Both my wife and I love our re-invented lives and we are thankful for trying the old Monty Python thing “And now, for something completely different.”

Have zero fear of retirement. I always advise: Don’t rush to get out the door. Honor your best earning years and stay until you feel fulfilled. Make sure you have enough money put away to see you through to the finish line.

But when the time comes, give some consideration to finding out what else you have in you. Push your limits to explore all the things you have only seen others do. Whether you succeed in those new ventures or fail, you will enjoy the ride. I wish you well. Aloha.