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I spent at least five years planning for it before I actually retired. I carefully met with financial advisers, I made sure my successor knew everything he needed to know to take over the job, and I started a second grad program a year before retirement because I knew I would need the transition time. You might even say I was smug about how well prepared I was.

A little more than a year later, I still think I did a good job organizing myself for everything I could imagine I would need and want. The problem, I now realize, is that you can’t prepare for what you don’t know, and what I wasn’t completely aware of was how much I would need to build a new person from the ground up. Of course that’s an exaggeration because much of who I am and what I do is unchanged since retirement.

I am happily married, I have a lovely home, I work out every day, and I enjoy a great group of supportive friends. Still, having been a workaholic for more than 30 years didn’t exactly set me up for a life that didn’t include work. Quite simply, work is what I know best in terms of what to do with my time. And, it’s how I have identified myself since I began identifying myself in the first place. So I’m searching around for guidance about how to create a meaningful life that isn’t focused almost entirely on work. I’m building and re-building, adding on, remodeling.

Most retirement experts say to look below the surface, beyond the actual work you did, to the skills you possess and the activities you enjoy. I started out years ago to be a writer and, once I realized how difficult it was to make a living doing that, gravitated quite quickly to teaching writing and communication. It made a great career, and I still enjoy those activities, so writing—and taking myself seriously as a writer—is top on my list. Since I have a comfortable retirement wage, I can work on what I really want to write without having to fill in with money-making gigs that I don’t really enjoy. No more gift guides for the local city magazine like I did back in my 20s.

But there are things that interest me that don’t have anything to do with work, and this is obviously the time to pursue those. I’d love to learn French, for example, and I fantasize about looking for new outlets for myself as a photographer. I even dream of making a short film and of living in other cities for a few months at a time. But I realize as I think of these things that I want to be careful not to get myself right back into a rigid schedule with little open time. That is one of the parts of working that finally convinced me to retire when I did. There was rarely a chance for exploration and, if I did stumble on something I wanted to pursue, there wasn’t any kind of unstructured expanse in which to do it.

I’m discovering that an important part of this process will be going slowly and not committing to something just because it reduces my anxiety. When I look back on my career, and my lack of deliberate direction when I was young, I feel lucky that I ended up doing something I enjoyed, but I think there is a deeper pleasure out there for me, and my big challenge now is reining myself in enough to truly figure that out.

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