How will I fill my days when I retire?

For many years before he passed, my father-in-law Tom liked to point out that he was retired and rarely had significant obligations on his calendar, unlike those of us still working for a living.

It would be a family get-together on a Sunday, and someone would say something like, "I have to work tomorrow." Someone else would chime in, "Me too."

Then Tom would flash that funny little mischievous grin of his and say, "Not me!"

I have often wondered what that life would be like.

Actually, we all get glimpses of it on our days off. Especially our weekday days off.

The stores and the roads are relatively empty. We're free to structure our time however we like.

And sometimes, after that giddy feeling of being unencumbered by job-related responsibilities passes, we're also free to be bored.

I look ahead a decade (or so) hence to my own retirement, Lord willing and the creek don't rise. The possibilities are intriguing and exciting, but I also worry I'll run out of things to do.

I imagine it takes a little while to get the hang of being retired. By the time I call it quits, I anticipate having been in the full-time workforce for 44 years or more.

That's a fur piece, as my dad used to say. Certainly long enough to develop deeply ingrained patterns of behavior necessary to survive and thrive in the world of work.

Changing those patterns can, I assume, be a bit of a challenge, especially when you reach an age when change of any sort is met with skepticism or outright annoyance.

How am I going to deal with that?

Maybe more importantly, how will Terry deal with having me around all the time?

I can't say for sure, but I can tell you something I noticed recently when talking with her.

It was a particularly stressful and busy week, and I sighed and said to her, "Am I retired yet?"

It took her less than half a second to reply with a sharp and emphatic, "No." The message I took away was, "No, you are not, and I would prefer you not be retired for as long as possible so I don't have to share this gloriously empty house seven days a week."

Maybe, if she has her way, I'll never have to worry about how I spend my retirement days because I'll never be allowed to retire in the first place.

What, me retire?

Not long ago, Terry and I had an overdue check-in with Dave, our Merrill Lynch financial guy (NOTE: That's not Dave above. That's Alfred E. Neuman. If you don't know who he is, you're probably too young to be interested in reading this post in the first place.)

Maybe the conversation wasn't "overdue," though. I'm not sure how often you're supposed to talk with your money person, but it felt like we hadn't taken a step back and discussed the big picture for quite a while.

While Dave stays in touch regularly, some time had passed since I had gathered all of our account information, sent it to him, and allowed him to run the numbers and gauge our financial health.

The results were encouraging.

Lord willing and the creek don't rise, we're right on track for me to retire in about 11 1/2 years. My goal is to work until the end of 2035 before calling it quits and enjoying whatever comes next.

I'll have just turned 66 at that point and will have been a member of the full-time workforce for two-thirds of my life (that's 44 years for those who didn't have Mrs. Schwarzenberg at Mapledale Elementary School and whose arithmetic skills may therefore be lacking).

That "feels" about right. I would rather not work full time into my 70s, if I can help it, but I also don't want to get out of the game too early, for reasons both personal and financial.

There are several factors that go into deciding how much money you need to sock away for retirement, including the lifestyle you want to lead once you get there. Terry and I want to be able to travel with some regularity, whether it's to visit kids/grandkids or just see the world.

I'm not talking about boarding a plane for some exotic location every two weeks. Maybe "several" trips a year, with most domestic and one overseas.

"Comfortable but nowhere near extravagant" is how I would describe our desired post-retirement lifestyle.

That's somewhat vague, I realize, but it was enough for Dave to decide we're ahead of the curve with our savings and investment plan, given the vagaries of the markets, my presumed ability to continue working for another decade-plus, and all of the other unpredictable realities that come with aging.

This was all somewhat of a revelation to me. I'm 54 years old. I don't think about retirement very often beyond how much I throw into my 401(k) and occasional dreams of touring World War I battlefields in France and Belgium once I have the time to do so (that's likely to be a solo trip sans Terry, if I had to guess).

For the first time, the conversation with Dave made retirement seem like a tangible thing and not just a far-off hope. I've still got a ways to go, and like I said, you never know what's going to come your way. But the fact is, it could happen, and that's fun to think about.

Again, though, as quickly as time passes these days, I still have several career-building years ahead of me, which is OK. We'll get there when we get there.

The closer it gets, the more real it will become, I'm sure.

I can't say for sure I really want to retire

Current life expectancy figures suggest that, as a 53-year-old American male, I can reasonably expect to live another 25 years. Could be more, could be less.

However you look at it, odds are I'll be around for a while longer. The hope has always been to lead a life of relative leisure for a portion of those years by eventually retiring from the full-time workforce.

Financial considerations aside, though, I sometimes wonder if I even want to retire. That may sound crazy, but you hear stories all the time of people (mostly men, it seems) who retire and decline rapidly thereafter. They lose the mental and social engagement that comes from being employed, and their mind and body go swiftly downhill thereafter.

That's obviously not the case for everyone, or even for most retirees. But it happens often enough that it makes me wonder whether they'll need to pull me kicking and screaming from full-time work sometime well into my 80s.

The best approach, they say, is to plan a retirement in which you direct your time and energy toward more fulfilling pursuits. The idea is to keep using your brain every day, but to use it for something perhaps even more enjoyable and more personally satisfying than whatever you did to earn a living for 40+ years.

In theory it sounds good, but for the life of me I cannot picture what that might look like. What would I do every day? Even now I'll occasionally take week-long staycations by the end of which, my wife will tell you, I'm scrambling for something to do.

And I say that as someone who dabbles in lots of different things. I have plenty of interests, but you know what they say about the days being long and the years being short? It's difficult to envision how I would fill those long days in retirement.

Maybe I'll think differently about all of this when I get into my late 60s and our retirement accounts are at a point where I can seriously consider moving into the next phase of life.

In the meantime, for as much as I might complain about it, I'm OK continuing to work a full-time job. I can only read so many books and practice my saxophone for so long every day anyway.

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.

Here's what I learn about retirement every year during my two-week holiday break

I'm writing this post about two weeks in advance of when it will actually publish, so I'm still in the middle of a 16-day holiday vacation from work.

I used to take these two weeks off mainly to spend more time with the kids, put their Christmas toys together (and play with them), and generally just rest and recharge.

I still use the break to rest and recharge, but every year I also see it as a small dress rehearsal for the part of my life when I will no longer work full-time.

The way things are shaping up, retirement is likely a good decade-and-a-half away for me. Our financial advisor asked me when I wanted to retire, so I randomly picked age 67. And that's very much a possibility.

Many of the people I know around my age are closer to walking away from the 40+ hours a week routine than I am, particularly those who work in government jobs and teaching, and/or those who have spent most of their careers with very generous companies that have padded their 401(k)s.

For me, though, retirement is still pretty far out on the horizon. In preparation for it, these two-week vacations have taught me a few things I'll need to know when it finally gets here:

(1) I'm going to need a part-time job. I can't just stop working. I will get too bored too fast. My dad drove a delivery truck and worked as a school janitor in his retirement. I don't know what I'll do, but I'll have to do something. If nothing else, it will keep Terry from killing me as I wander around the house wondering what I should do.

(2) I'll need to have defined hobbies. I wrote about my leisure-time activities recently. They will be especially important in retirement when it comes to providing fulfillment and some sort of purpose in life beyond career advancement.

(3) I would rather not cut grass or shovel snow in retirement, if I can help it. Terry and I have talked about being snowbirds in our golden years, and that may happen. But if we're spending any part of the year in Northeast Ohio, we're either going to have to live in a condo or hire a landscaping/snow plowing service to fulfill this desire of mine. I'm down for anything, just as a long as I don't have to push a lawn mower or wield a snow shovel anymore.

I probably need a plan of some sort...

I have one daughter in college and another who will be starting in less than six months, and I feel like I should be providing them more in the way of career advice and guidance.

The problem is that I have no idea what to tell them. I never received much advice myself, so I've always just kind of winged it when it has come to the world of work.

Job interviewers will occasionally ask you, "So where do you see yourself in five years?" And I don't know what to say, because I honestly don't know where I see myself in five minutes.

Which in some sense is OK, right? You always hear how you should live in the moment and not worry about anything but today. And I'm really good at that.

But I think looking ahead to the future is also a pretty good idea, and I rarely do it. I am so absolutely caught up in getting through the here and now that I lack the time, energy and focus to plan for anything beyond that.

This is somewhat reflected at work, where as a director-level employee I'm expected to be forward-thinking and strategic. Yet what I'm really good at is getting things done. Checking boxes on the to-do list. Making it to the end of the day with as many things in the "finished" pile as possible.

Co-workers will ask me, "What's your plan for that?" My answer is usually, "Um, let me get back to you." And I do eventually get back to them with plans that are (surprisingly to me, anyway) pretty good. Which shows that I have the ability, just not the inclination.

Anyway, when it comes time for me to offer fatherly career advice to the kids, I'm kind of at a loss. If I don't chart out my own path, I'm certainly not the guy who should be mapping out someone else's.

I mean, I have some idea of where I'm going with my career: retirement. At what age, and whether that will even be possible, are both unknown to me. As are the details of just how I'm going to get there. My general intention is to keep working, saving money when I can, and finding some as-yet murky way to stop working so I can retire and do...something else I'm not sure about.

You see what I mean? I'm kind of directionless. Just get the kids raised and safely into their own lives, that's pretty much the extent of my "plan." Beyond that, I think my life will eventually also involve going to more hockey games and orchestral concerts.

And...that's about all I have.

If someone would like to offer life guidance and career planning services to my kids, I would be ever so grateful.