My Satisfying Retirement : How Retirement Starts

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I recently shared a post about my continuing valent attempts to paint. That reminded me that eleven years ago I wrote that retirement begins like a blank canvas.  You’ll buy all the paints and brushes but will have no idea what it will look like until you start applying the paint. Update: Over the years, I have learned this is not a very accurate depiction of what happens.

At the time, the empty canvas seemed as valid a metaphor as any. In theory, we all begin our time after full-time work unsure of what is going to happen. Sure, we made plans. Obviously, we have ideas about what a satisfying retirement will look like. We collect opinions from friends and family. We probably have read a few books.


Like me, maybe you were convinced you had it all figured out. Step A will be followed by Step B. This will happen, and then the next thing on your retirement to-do list will occur. So, the idea of starting with a blank canvas and creating what you want from scratch made sense.

Yet, rarely does it work that way.  Life has a nasty habit of messing with our plans. Things completely out of our control suddenly pop up in the path ahead of us. You are not going to know what your life really looks like until you are into it. Add to that the reality that life is really nothing but a series of changes. Maybe an etch-a-sketch would be a better visual prop.

Create what looks good to you at this moment. Then, you realize that whatever is before you isn’t working. Your financial foundation begins to show a few cracks. A relationship that seemed destined for a long run starts to veer off course. 

That volunteer work that made you feel complete and helpful began to take over more of your time than felt right. A hobby that once made spare time fly by became more of an obligation.  I better keep playing the guitar, not because it is fun but I don’t want to waste the money I spent to buy it, an example of the sunk cost fallacy, where someone irrationally clings to things that have already cost something.

I have had an idea for a side hustle that combines my love of woodworking with a shot at making some extra income. I seem to be pretty good at identifying stocks that will increase in value. Should I spend more time learning about self-investing?

My mom is getting sicker. I really have to make arrangements to get her into a safer environment and spend extra time visiting her. 

I really, really love to travel, explore places I have never been to, and meet people who can teach me about a different way to live. 

The examples are endless, but the point is a retired life, lived to its fullest, can’t be permanently portrayed by paint on canvas, or anything that is permanent. My metaphor doesn’t hold up well to reality, except in one regard.

I described the canvas as having lots of open space left after you had filled in what you wanted to happen. That part of the analogy still works. I wrote, ” There is still a lot of open space left. The canvas is still more than half empty. Why? Because every single day you have the chance to add something to your life. If you approach retirement as an adventure that is open to additions and recreations, the canvas will never be finished. Just like a good artist, you believe you can always add a dash here or a blob there to improve the painting and your life.”

Over twenty years of retirement and almost twelve years of writing about it has taught me a lot. It has opened my eyes and it has shocked and disappointed me on more than a few occasions. 

It has also amazed me with the resiliency of the human spirit and the will to grow. It has proven that no life is meant to be a blank canvas we complete just after retirement. A photograph is just one second in time. 

Our journey in this third stage of life is impossible to capture in all its fullness and complexity with any one idea, one representation, one approach. Forget trying to fill in the blank canvas. Instead, embrace the spaces still left to discover.

Every once in a while, give your etch-a-sketch a good shake.

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