“Won’t You Be Bored?” and Other Questions You Hear on the Road to Early Retirement

We’re lucky to have the full support of both of our families in our early retirement planning. We’ve heard other bloggers say that their loved ones aren’t fully on board, or they intuit that they won’t be and so don’t even tell them. For those of you in that position, we hope you won’t give up on people coming around, because we’ve found there’s tremendous joy in being “out” about our plans, at least with our families and a select group of friends, and with just random people we meet on planes, at the dentist, you name it.

One of the funny things that happens, though, when you’re open about this stuff, is you get some questions that might seem ridiculous on their face, especially from people who haven’t yet had their minds blown by how achievable some form of early retirement is for plenty of folks, or who have never allowed themselves to dream about a life without the necessity of work. Or maybe they truly love working. Either way, the questions can feel like they come from left field, because they come from such a drastically different perspective than ours.

The question that I’m sure plenty of you have also gotten is, “But won’t you be bored?” which seems to come most from people who don’t know us directly, like if our parents tell someone they meet about our plans. Sure, we could dismiss that question out of hand, or even counter with my favorite retort to bored campers when I was a camp counselor back in the day: “Only the boring are bored!” But in our classic overthinking style, we believe it’s worth digging into these questions, and asking ourselves if there might be some legitimate caution worth considering and planning around, instead of just rolling our eyes and telling ourselves, “Clearly they don’t get it.” Maybe they don’t, but that doesn’t mean they don’t have a point — these things don’t have to be mutually exclusive.

So let’s do it. Let’s dig in.

Won’t You Be Bored?

Let’s take the biggest one head on. Boredom. It is irrefutably true that plenty of people, especially those who retire at a more traditional age, have trouble filling their time once work is out of the picture, and they end up spending their days in front of the TV or, worse, parked in front of a slot machine. Could we end up this way?

We certainly don’t think so, because we’ve always had more interests than time (probably why people who know us never ask us this question), and because we have a strong sense of purpose for our lives. We’ve also heard from other early retirees that they still feel super busy now, even without work eating up a big chunk of their time.

But, even if we’re not technically bored, could we still end up spending too much time on the couch? Absolutely. We’re anticipating needing to catch up on sleep for quite some time after we retire, and it’s easy to see how that could be a slippery slope to couchdom if we’re not careful.

So in our case we’re worried less about a traditional definition of boredom, which we feel relatively immune to, just because we are rarely bored in life. But we are a smidge more worried about frittering away our time without doing anything productive, active or meaningful. How we’re planning to counter that: scheduling things that drive motivation. We have to get out and hike if we have a big mountain climb scheduled, and we have to brush up on our Spanish if we have a flight to South America booked (or maybe we’re climbing a big mountain in South America – then we have to do both!).

We’ll also keep using the power of streaks to keep this blog going, and to get other good habits in place. And we’ll stay aware. Maybe our approach will have to evolve, and we’ll end up doing something like making a plan to do one productive thing each day, or create timelines for ourselves to finish creative projects. This is something we know we need to keep an eye on.

Won’t You Miss Working?

This question is the easiest to dismiss, because we definitely won’t miss all the meetings, the office politics, the wacky client demands, the 5 a.m. flights, the limited vacation time. But there’s a nugget behind this question that’s worth thinking about: Won’t we miss feeling productive? And if our plan was to sit in a La-Z-Boy and become connoisseurs of the Price is Right (is that still on?), then YES, we would miss feeling productive.

But our definition of early retirement doesn’t include never being productive again. The definition of work will just change dramatically. “Work” will become writing for pleasure, volunteering on boards and coaching nonprofits to improve their effectiveness, helping out our friends with their small businesses, maybe taking a job with ski patrol in exchange for free skiing. And all of the non-work productive stuff: making all of our food from scratch, doing all of our home and car maintenance ourselves, gardening as much as our high altitude climate will allow.

Early retirement doesn’t mean never contributing anything to society ever again, and for that we’re glad. We plan to get more useful to society in retirement, and have a hard time imagining that we’ll miss “work” in a traditional sense.

What About Social Interactions?

This is a biggie, and one we’re thinking a lot about for a future post. While it’s definitely a blessing that we’ve both been able to stay with our companies for more than a decade, that could make it a bigger shock when we leave our jobs, since we’ve become friends with a huge number of our coworkers over the years. We definitely think about how much tougher it will be to maintain those relationships once we’re not naturally talking all the time, like we do now at work.

And outside of work, we’re not sure that we’ll see our friends all that much more. Sure, we’ll stop traveling for work, which should make it easier to get together during the week, but our friends will still be working. They won’t magically have time to hang out with us during the day, or for those who live far away, they won’t all of a sudden be able to come visit us more, just because we have more free time.

Making new friends with free time that matches ours is something high on our to do list in retirement, and we’re definitely realistic that that could mean befriending a lot more people who are of traditional retirement age. Where we live, people stay super active until their extremely advanced years, so chances are the “old fogies” we befriend will still beat our slow butts up the mountain!

Won’t You Miss Feeling Important?

We’d be lying if we pretended that we don’t have egos. We do. Like most normal people, we like having them stroked. And for the past 15+ years, most of that stroking has come at work. (Hey, Personal Economist — that’s now stokin‘, streakin‘ and strokin’!)

We’re less worried about our titles, because we can sort of take those with us. If we feel the need we can always say, “I’m a former fancy pants title at such-and-such impressive employer, but I’m retired now.” Not that we’re guessing we’ll drop that info too often. It’s more the day-to-day stuff — no more gold stars or public recognition for good work, no more feeling like the go-to people on certain issues, not getting to ride in the front of the plane anymore. It’s definitely going to be an adjustment, and we’d be fools to pretend otherwise.

But we’re hopeful that this is something we can counter by not defining ourselves solely by our work. We consider it a massive blessing that our local friends don’t even really know what we do for work — it’s just not what mountain town friends care about. We all know that we moved here to be in a beautiful place and spend our time outdoors, not because we’re trying to advance our careers. (More likely, we’ve all committed some level of career suicide in moving here.)

Instead our friends know that I prefer my road bike and Mr. ONL prefers his mountain bike. That he’s the guy you call when you want to do a quick early morning backcountry ski lap. That I’m who you call when you want to take the dogs on a long hike. That we love every kind of trivia game and torture ourselves with hard puzzles. That we’ll happily go along to see just about any kind of live music (just no death metal, please). That we’re good listeners and loyal friends. And those are all identities that we’re happy to be defined by, even if they don’t come with gold stars or fancy airline status.

What If You Run Out of Money?

Answering “We won’t” isn’t good enough for this question. Not one of us, not Warren Buffett himself, can see the future and guarantee that our best-laid plans and oodles of contingencies will guarantee that we’ll never run out of money. We still might. Of course we’ll all try mighty hard not to run out, but we’re lying to ourselves if we pretend we can control every eventuality.

Instead of debating that question, we think about the other side of the coin: Is it better to keep working forever because you’re afraid your savings might not last you long enough? Either way, you’re taking a risk: either you risk running out of money, or you risk spending all of your good years working. We’ve done our due diligence in building a financial plan that we think has a very good chance of withstanding the long haul, but beyond that, we’d rather take the risk that we run out of money but at least maximized our enjoyment in life. We’re comfortable with the poison we’ve picked, but others might reasonably choose a different path.

What Other Questions Have You Heard?

What questions do you hear when you tell people you’re following a nontraditional financial path? How do you answer any of the questions we’ve heard a lot? Lay it on us in the comments!