Position: Supine

Bob Iger’s return as Disney’s CEO 11 months after handing the reins to his erstwhile successor proves both he and Disney’s board lack any imagination. At 71 Iger should be retired and pottering around his mansion. Instead, when the call came, he dropped his mimosa in the pool and scurried back to his office, his seat presumably still warm. Bob never retired, and probably never will. They will drag him feet first from the boardroom. When they do, Disney will still have a succession problem.

My point is, if you don’t have anything else to achieve in life, work is the less difficult, less imaginative answer to how you fill your days in retirement. It is structured, hierarchical (you have to do as you’re told), and you have to please others, not satisfy yourself. When I worked in the operating theatres of England’s National Health Service, I heard stories of surgeons who had died within months of retirement. The change in status, upset to routine and relief from the daily pressure of saving lives seemingly too much for them.

The lesson stuck with me. I understood early I needed to decide what I was going to do with the last third of my life. Circumnavigating the world on a sailboat kept bubbling up to the top of my list. That along with making a movie, writing a book, mastering digital photography, building a house with my own hands, and riding a motorcycle from Alaska to Argentina. I guess I was a proto-Millennial after all.



Internet pundits say there are anywhere from 3 to 15 stages of retirement. Financial advisors talk about saving, preparing, administering, and finally spending your money, if you’re lucky enough to have any. Yes, but spend it on what? That begs a different question. What do you want to do in retirement? Where do you see yourself in five years’ time? To help answer that question, let’s review retirement’s four emotional phases outlined by Riley Moynes in his recent TEDx talk.

Phase 1: Vacation – You’re on holiday! Woohoo! You don’t have to answer to anyone, you get up when you want, you can travel, lounge around and be self-indulgent. For as long as you can afford it. For many this phase lasts around a year, or more. At some point it loses its appeal. Some get bored, some miss the structure of the office, some wake up to the loss of their workaday routine and purpose.

Phase 2: Loss – Parents understand the loss of their children (finally) leaving home and striking out on their own. Retirees go through a round of similar losses. Just like when the kids leave, when you retire you give up routines, an identity, working relationships, often a sense of purpose, and for some a loss of power. Once your colleagues show you the door, all that goes “poof!” Couple that with inevitable physical and mental decline, it is easy to feel depressed, even anxious about the future. There may be another 30 years of that to look forward to.

Phase 3: Trial and Error – In this phase it is normal to explore questions about how to make your life meaningful again. How can you make a contribution? Moynes encourages retirees in this phase to experiment. Try different things, he admonishes. Find something that gets you up in the morning full of excitement, otherwise you risk falling back into phase 2. This isn’t very different from our teens when many of us took jobs we never wanted to do again. Those formative experiences directly or indirectly guided us towards our careers.

Phase 4: Reinvent and Rewire – Assuming phase 3 yielded some success, even by process of elimination, phase 4 is the time to focus on the things that give you a sense of accomplishment. In Moynes’ words, how to squeeze the juice out of retirement. That sounds like exsanguination to me, but the gist is embracing the opportunity to do something that you’re passionate about and reward yourself by doing it.

Believe It

The truth is many people refuse to retire even though they have the means to. (I’m talking to you Bob.) But for a moment, let’s assume you’re fortunate enough to have planned well after a successful career and believe you have enough money to retire. Furthermore, you’re mentally prepared for the emotional transition and know what to expect. Even better, you’ve already been through a few of life’s big transitions (job changes, relocation, launching children) and can comfortably draw on those experiences to guide you. You’ve completed your vision board with its list of goals. You’re ready – almost. The last cog in the retirement machine is your physical abilities.

You Can’t Fight Physics


As you look at your long list of ambitious objectives, our recommendation is you prioritize the physically demanding things first. We decided to jump into an ‘early’ retirement because we chose sailing around the world as our primary activity. Both Carol and I know what it’s like to be physically fit. We know what recovery is and it takes longer than ever these days. In the five years we’ve been enjoying our extended vacation phase we can tell you things aren’t getting easier.

When we bought Aleta at least a third of the boats we looked at were being sold by people with a lifelong goal of sailing off into the sunset, but who had never left the harbour. The most common reason was one or both partners fell ill, or they no longer felt strong enough. As brokers reminded us, their loss is your opportunity. (Ah, the brutality of capitalism speaks… – ed.)

From the start, and without much preplanning, we agreed that we’d give it a year. See how it went. Then give it another year. We also talked about a rough five-year goal for making it all the way around the world. Then we’d take stock and review our list(s) and decide what we’d do next. If we had to work, we’d do that. If we found a place we loved and could save money living there, we’d consider that too. We hadn’t planned on Covid, or Brexit, but we also know all plans change as soon as they’re implemented. After five years, my sense of urgency for completing the hard, physical part of our journey is increasing. Like I said, it’s not getting easier.

Get Off The Dock

Are we just in an extended vacation phase? Are we simply denying the other emotional challenges of retirement? Not entirely. Having spent so long thinking about circumnavigating, I still have my long list of other goals to address at some point. After all, this blog is over 250,000 words long and I know there’s a book in here someplace. Perhaps even a film.

You can wait forever to retire. Or simply not bother. That’s fine. It’s your life and, frankly, I don’t care what you do with it. But if you’re delaying a dream you’re running out of time. At some point you have to choose between pursuing that dream or living with the disappointment of never having left the dock.



  1. yep,
    I keep telling a few friends of mine that if they think lining up all of their ducks is the path to retirement, they will never line up all the ducks. I am older than most of my friends by 5 years, and Ward by 2 years. I exercise, eat right, and try to follow a path of keeping this machine of mine engaged. Building this house was without a doubt the hardest work I have ever done, and we did it. That makes me happy, and as you say, no one could have planned on Covid, a conundrum. The future is hard to predict. Come visit when you can, we are here now, enjoying life large. This retirement story is still evolving.

    1. Thanks Patti – you guys are truly living the a dream you planned on and executed with determination. Building your dream house on a Hawaiian island must draw the admiration of everyone you meet. And I’m sure your artistic biases must have helped make your vision a practical reality. We’re coming to visit and when we do, you’ll come for a sail, I hope.

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