(I know, I know, that title reference may be a bit historical for some of you. Here’s the link. )

WordPress, this blog’s host, has been running a “PostADay2011” promotion with daily thought-provoking inspirational questions. The kickstarter for Tuesday 28 June was “What have you feared that turned out to be much easier than you expected?”

Oddly enough, the #1 answer from the WordPress bloggers seems to be “Setting up a WordPress blog.”

But in my case, the question made me think of the #3 fear of all potential early retirees: “But… but… but what will I do all day?!?”

(The #1 and #2 fears of civilian early retirees are finding affordable health insurance and coping with decades of inflation. Most military ERs have solved those issues with Tricare and a COLA pension.  If you’re a veteran without those benefits then you still have to deal with those challenges, but you have the skills & discipline to solve them.)

The short answer to the #3 fear usually materializes a couple of months after early retirement when you wake up one morning, contemplate the busy day ahead of you, and wonder what the heck you were worrying about all those months ago.

But if you’re not ER’d yet then you’re probably skeptical that it’s so easy. (I know I was.) So how do we ERs reassure you that it’s not worth the worry?  How do you educate yourself out of this anxiety?

The first approach is to think back to your carefree childhood. When school was out for the summer, did you have any trouble entertaining yourself? If you were like 99% of the world’s kids & teens then you were going from sunup (or whenever you finally got up) to well past sundown, and you still didn’t want to stop just because it was time for bed. Growing up in my household, our occasional “I’m bored!” whining was a shameless attempt to manipulate our parents into making us do yardwork taking us to the pool or on a trip. When we had our own wheels (and enough money for gas) we found even more things to do.

A second way to look at the issue is to review your “To Do” list. How many weeks would you need to knock out all of those tasks? Once you add in trips to the home-improvement store and a few do-overs, you might want to double the original estimate. Now how long would it take? What about the things you’ve wanted to try but never had the time to even contemplate, let alone plan? Now how long would you need? And would you have to repeat any of those tasks in a few months or next year?

Take the experiment one step further: imagine that you’ve crossed every task off the “To Do” list. (Yeah, I know, you married men think it’s never gonna happen, but humor me with this thought experiment.) What would you do now? Linger over an extra cup of coffee each morning with the morning news or a book? Spend more time with your kids? Exercise more often? Go surfing or play more golf or enjoy other sports? I’m not trying to suggest that you’ll spend hours on every one of these activities every day of your life, but you’ll certainly adopt a more leisurely pace.

Finally, for those of you engineers preferring a more quantitative approach to your problem-solving, start with a blank weekly schedule. (Feel free to spend some time gazing upon it and fantasizing about all the empty space on it– especially the parts that right now are filled with department meetings, mandatory training, and deployment preps.) Start filling in your daily routine– when you’d like to get up, when you’ll be ready to start the day, how much time you should spend on chores, when you’ll run errands, how often you’d like to exercise or play sports or enjoy your hobbies. If you have a family then add in their schedules too, so that you can be there for them yet still carve out plenty of your quality “alone” time. Consult your “To Do” list to break down a few of those monstrously overwhelming tasks into chunks of “20 minutes a day”. Make sure you fill in your new weekly schedule’s after-dinner time, too, even if it’s just a neighborhood walk or watching TV.

Still worried about what you’ll do all day?

Maybe some of you prefer a more experiential approach to your learning. In that case the analysis might be more difficult to set up, but it’s worth the effort. The issue is that you’re going to need a minimum of two weeks’ vacation, and six weeks would be better.

I’m not talking about the chaotic 30 days of leave you take when you’re transferring between duty stations and uprooting your whole life only to transplant it to somewhere else. (For some families that month is even more stressful than deploying to a combat zone!) I’m also not talking about the Great American Family Vacation where you burn hundreds of gallons of gas racing hither & yon across your time zone, taking in all of its sights & attractions. I’m not even talking about the staycation from hell where you paint the house, scrub & re-coat the deck, clean out the garage, and weed/fertilize the lawn.

I’m talking about weeks of unstructured laziness. I suspect that you’ll spend at least the first week catching up on your sleep and reading or watching TV. By the second week you’ll probably be back to a “normal’ sleep schedule and more interested in your surroundings. Feel free to do your normal daily/weekly chores, but don’t tackle any big projects. This might be a great time to review your early-retirement financial plans or to crunch a budget spreadsheet, but don’t turn it into a multi-hour marathon. Spend time on leisurely walks and get a little exercise. If your spouse & kids have time off, too, then spend some quiet family time together. Board games or video gaming are reliable fallbacks, but maybe you’d want to include a trip to the library or the weekly grocery shopping. You’re looking for opportunities to talk together and to enjoy each other’s company without rushing between activities.

As the end of these weeks draws near, think back on what you’ve done. Did you want to spend more weeks doing it? Did you run out of things to do? Were you bored to tears and champing at the bit to get back to the workplace?

If none of the above approaches will work for you, then don’t lose hope– go find Ernie Zelinski. He’s written two famous books on retirement: “The Joy of Not Working”  and “How to Retire Happy, Wild, and Free“.  (Check your local library.)

Each of them offers a couple of hours of light-hearted musings on what it means to be responsible for your own entertainment, along with suggestions on how to take charge. “Happy, Wild, & Free” also includes his “Get-A-Life Tree” brainstorming tool.  You start with the activities that you’re currently enjoying, add in your “To Do” list and your bucket list, and then try to decide how to fit them onto a calendar.

I’m a big fan of the “Get-A-Life Tree” technique, and I’ve recommended it to dozens of people over the years. However, I have to confess that I’ve had a blank copy of it sitting on my desk for over a decade. I meant to fill it out as I was planning my early retirement, but things were too busy. I meant to fill it out when I was on terminal leave, but I was too busy. I meant to fill it out after I retired, but I was surfing. I’ve meant to fill it out the very next time I was looking for something to do, but I’ve never made the time for it. Ironically the “Get-A-Life Tree” has ended up way at the bottom of my “To Do” list, for the extremely unlikely event that all else fails to entertain me.

Use the Tree to jumpstart your own thinking, but don’t feel obligated to complete it. It’s just a tool to help you get going, or something to put on your desk to reassure you when you wonder what you’ll do all day.

One last encouraging story: A good friend has been approaching his significant transition from active duty to early retirement, and I’ve enjoyed watching him work through the process. Several years ago his attitude was “I can’t just rust in the rocking chair. I’ll spend time in the Reserves, get a teaching job, and tackle more rental properties.” A couple years ago he mused “I don’t think I want to hang around the military, but I like the idea of teaching. Maybe a few evening classes a week, but probably not full time. Maybe just one or two more rentals.” Last year it evolved to “I’ll run an online course or two.  Maybe we just bought our last rental property.”

Now his retirement is at hand, and his plans are bubbling over with activities. He’s enjoying much more time with his family. He’s coaching his kid’s sports. They’re taking short trips during summer vacation. He’s thinking about surfing lessons (in Hawaii, of course) and Space-A trips to Southeast Asia. He’s not sure how much time he’ll have for online courses or rental properties, but he appreciates having the extra cash available if needed.

I should mention that he hasn’t even networked for a bridge career, yet he’s received several job offers with eye-popping salary numbers. Unfortunately he’s too busy at this stage of his life to accept paid employment…

Related articles:
Myths of military retirement and early retirement
The “fog of work”