Sometimes I think I enjoy planning life more than I enjoy living it

When it comes to going to the gym, while I do genuinely like the act of lifting weights, what I really like is sitting down the week before and planning out which days I'll be working out and exactly which exercises I'll perform (with the attendant number of reps, sets, etc.)

In the same vein, Sunday afternoon is one of my favorite times because it's when I sit down and type my to-do list for the coming week into Microsoft OneNote.

And while I've never really had a vacation I didn't enjoy, to me nothing beats the fun and excitement of actually planning the vacation.

Do you see a pattern here?

I am by nature a planner. This is good thing to be in many respects, as it provides some degree of control – or at least the illusion of control – in an otherwise chaotic world.

But the drawbacks of being an inveterate planner are perhaps equally apparent. You don't always respond well when a plan (inevitably) goes awry. And you'll never be known as the most fun and spontaneous guy in the world.

There's also a tendency, at least in my case, to skip from one life plan to another in a futile attempt to discover the perfect way of living.

In my heart I know there is no such thing as "the perfect way of living," but my head insists it's out there somewhere and that, with each iteration of my life plan, I get that much closer to it.

To be clear, by "life plan" I mean a philosophy or approach to everything that consumes my time, both at home and at work. How should I do my job? How should I eat and exercise? When will I find time for spiritual nourishment? How much of my fall and winter nights should I devote to PA announcing gigs?

I try one life plan for a few months, then when I discover where it falls short, I switch to another. Sometimes these are small tweaks, while other times I make large-scale, wholesale changes.

All of which begs the question of why I can't just acknowledge that circumstances vary and I need to take things a day at a time, adapting to whatever comes my way without searching for a one-size-fits-all template.

In short, why don't I just, you know, live life?

As if often the case when I examine my own personality quirks, I don't have an answer to that question.

BUT...it's on tomorrow's to-do list to check some books out of the library that might explain why I am how I am.

At some point, often in your 40s or 50s, you have to decide how the rest of your life might look

Life expectancy for American men these days is right around 78 years. My plan is to exceed that, and exceed it by a wide margin if I can.

Assuming things work out that way (and let's face it, there's always the chance they won't), I still at best have reached the halftime of my life, or more likely am somewhere early in the third quarter of play.

When you get to this point, you stop for a second to look back at where you've been and, more importantly, try and figure out where you're going.

This is especially true in my case. Professionally, I find myself in an unplanned mid-career pause. Personally, I've now lost both of my parents and am fast approaching a life that, sometime in the next decade, will see Terry and me living on our own again, sans children for the first time since 1993.

While I am very much a planner, I'm not much of a long-range planner. I've never had a roadmap for my career, and things have been so chaotic around our house for so long that I don't even think much about next week, let alone next year.

Retirement? At some point our financial guy asked me when I wanted to stop working full-time. I told him 67, which was honestly about as arbitrary an age as I could possibly have come up with. Yet our entire portfolio is now structured to get me out of the full-time workforce when I reach that age in 16 years.

Where will we live? Will we stay in Wickliffe? Will we even stay in Ohio? We've had conversations in both directions. I don't yet know the answer.

What do the last 16 years of my career look like? Will I stay in corporate communications? I assume so, but I'll admit I don't know. Life is funny that way...the whole "man plans, God laughs" thing. If nothing else, I've learned that things change in the most unexpected ways, and the best you can do is chuckle with the universe and roll with it.

What about my health? I don't like where I am physically right now. I was in great shape five years ago, but I've lapsed back into old habits that aren't conducive to beating that life expectancy target. That all needs to change immediately.

So many things to consider, so many variables, so many possibilities. One way or another, we all wrestle with these questions on our journey. And to be sure, I have more questions than answers right now.

Including whether the Browns will win a Super Bowl in my lifetime. That one is killing me.