Do you even want to retire?


I talked last time about the need for a plan for your time in retirement.

Of course, for many of us, the idea of retirement seems a fantasy, and a cruel one at that. Who is going to have the money for that, aside from the 1%?

My answer to that, if you’ve been reading this site at all for any period of time, is that almost anyone can retire if they want to. Even you. And this isn’t even taking into account Social Security. You just need to get on a plan, discover the secret life of your money, and stay focused. In fact, I believe that anyone who has a few decades of working life left can become a millionaire.

Yes, you may need to ditch some of the Do What You Love aesthetic for a little while, and actually get a real paying job, but it’s temporary, and worth it over the longer term.

But here’s a question fewer people are asking: Do you even want to retire?

What we talk about when we talk about retirement

It’s worth thinking about what we even mean when we talk about retirement.

Merriam-Webster gives the following definitions:

: the act of ending your working or professional career

: the period after you have permanently stopped your job or profession

If I’m to use my own definition, it would be the time of your life at which you stop working because you “have to”.

This sounds great in theory, especially after an incredibly stressful day or week (or month (or career)).

But maybe it’s worth looking back at the sharp distinction between the two phases of life: B.R. (Before Retirement) and A.R. (After Retirement). I object to the sharp distinction, on the grounds that it bills work as something akin to holding your breath, and at some point you exhale and let it all out.

Instead I wish to see a more transitional status in our consciousness about this topic. Rather than a single event, we might be better off thinking about a process, one that may last years.

Pleasures and sorrows

This is assuming that the gradient even interests you. Unless you have a truly horrible work situation, which I’d like to think you could eventually overcome, there is a kind of joy in working, even if it’s for an entity that you’re not entirely in alignment with.

As Alain de Botton writes in “The Pleasures and Sorrows of Work

Death is hard to keep in mind when there is work to be done. … Work does not by its nature permit us to do anything other than take it too seriously. It must destroy our sense of perspective, and we should be grateful to it for precisely this reason … What is interesting is that we may take it upon ourselves to approach tasks with utter determination and gravity even when their wider non-sense is clear. The impulse to exaggerate the significance of what we are doing, far from being an intellectual error, is really life itself coursing through us.

I’m not saying that we work to avoid death, just that there is a satisfaction in working toward something. Even if we never achieve this something, the working toward it is a fuel that motivates us. And being motivated in one area of our life can keep us motivated in other areas as well.

And at what point in your life do you want to not be motivated for anything?

Grief and change

My dad, who is recently retired, spoke of retirement as containing a kind of grieving process. I never thought about it that way, but it makes sense, in that any change involves loss. And for some people for whom work imparts a kind of identity, the loss of this may prove painful. (I know a lot of about losing identity myself, and I’m not even retired.)

All of this leads me to think that thinking of retirement in the traditional sense as an event and not a process is not beneficial to us.

A better way is to think of it as just another transition in your life. One that you can, in most cases, control. Which means you decide how you want it to look. Or if you want to do it at all.

In the meantime, it’s back to work. We life more life to course through us yet.


  1. Heidi

    Great points! I totally agree that retirement is one of the major transitions that most people, in some form or another, eventually go through, and we don’t talk enough about the challenges that come up with it. However, I’m not sure we can “control” transitions… Or at least, once they start, we don’t always have control over where they will take us. I love what William Bridges has to say about transitions, and I think it totally applies: “Change is situational. Transition, on the other hand, is psychological. It is not those events, but rather the inner reorientation and self-redefinition that you have to go through in order to incorporate any of those changes into your life. Without a transition, a change is just a rearrangement of the furniture. Unless transition happens, the change won’t work, because it doesn’t ‘take’.”

    • Mike @ Unlikely Radical

      Hi Heidi. Thanks so much for the perspective. I guess I never really thought about the distinction between “change” and “transition”. But you’re right: if we define “change” as an external process, and “transition” as an internal reaction to that process, then it clears up any ambiguity.

      Stopping work is the change. The process of adjusting to this new life, and possibly redefining who you are as a person, that’s the transition. I like it.

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