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Bridget Fonda recently made the headlines of some sleazier rags when she was “spotted” out and about living her life. I don’t know if this will shock anybody but she is now actually older than she was when she starred in films like It Could Happen to You (1992) and Jackie Brown (1997). But tabloids love to make the everyday seem salacious, and poor Bridget Fonda was raked over the coals for no longer being as slim and blonde as she was in her twenties and thirties.
Oh, Hollywood – the land of eternal high-school-level torment and absurdity.
Although I’m sorry poor Bridget’s privacy was invaded and she had to face the imbecility of the tabloids, I am always happy to be reminded of her movies, particularly It Could Happen To You, which I think is a cute little film. It’s the story of a cop who, after going into a diner for a quick bite, realizes he doesn’t have enough money to tip his waitress. He does have a lottery ticket, though, and he tells her he’ll be back tomorrow to split any winnings. Of course, he wins. Of course, he splits it with her. And of course, they fall in love. Is it corny? Yep. Is it serious cinema? Nope. But I’d say it’s a light and harmless way to pass part of an evening. It’s the marshmallow fluff of movies. Not filling. Not nutritious. But it’ll make you a little nostalgic and give you something to smile about while you enjoy a spoonful.
In our podcast, we covered the relationship dynamics between the two love interests (Fonda and Cage) and the partners they had before they met each other. But for this post, I’d like to talk about an interesting dilemma that faces a small and very lucky portion of the population (including the FI community): if I have enough money to never work again, should I quit?
My advice to lottery winners (or anyone else with a big, sudden windfall) would unequivocally be to not quit right away. A huge and unexpected influx of cash is amazing. (I don’t agree with the idea that lottery winners are doomed to be cursed and struggle with their wealth forever after.) And not working also can be amazing. But give yourself a chance to take a breath. Because directionless leisure can actually be a dangerous thing.
The internet is full of warnings about retiring early. The Social Security Administration even put out an article about it. The world will tell you it leads to depression, feeling useless, and even early death! Simply put, people need a reason to live. They need a reason to peel themselves out of their soft, cozy beds in the morning. They need to feel needed, important, and helpful. And a lot of people get those things from their job.
In the Financial Independence community, this early-retirement-early-death connection is often sneered at because we feel like we’re just better than that. A lot of people in the FI community are brimming with ideas of how to use their free time, and they don’t want their pesky jobs standing in the way of those dreams. And, of course, they’re typically retiring a lot younger, which means they’re less like Brooks in The Shawshank Redemption – institutionalized and incapable of readjusting to a life full of freedom.
But it’s pure hubris to think that anyone is immune to the danger of feeling depressed and plain-old left out without a mandated thing to do each day and mandatory interactions with other humans. It takes real initiative to build a fulfilled and happy life when you have no one looking over your shoulder and you have nothing to do. And guess what you might be lacking if you are feeling adrift and ill at ease with nothing to do? Yep – initiative.
Sure, everyone can agree that it feels fantastic to have nothing to do for a short while as a respite from a typical busy life. But it can feel empty and dull and lonely if your calendar is empty for as far as the eye can see.
Some people love it and revel in this open-endedness Others fill their calendar with challenges and activities that bring them far more joy and meaning than any job ever did. But others are restless, depressed, and deeply unhappy without a clear purpose each day.
Before you quit a job, it’s wise to take steps designed to help you figure out which one of those people you’ll be. Because, according to the Social Security statistics, a large percentage of people fall into the last category and feel no purpose or joy in life without their job.
So how do you figure out which one is you? The first thing you can do is look at how you’ve historically handled your time off. Your vacations, your weekends, your summers as a kid. Everyone feels great on a Friday evening, when the weekend is full of promise. But by Saturday afternoon, how are you actually using your time? Are you working on exciting projects that you wish with all your heart you had more time to work on? Are you spending lots of time with family and friends, soaking up the sunshine and feeling gloriously free? Or are you on the couch thinking: I know I had things I wanted to do but … those can wait. In your summer vacations as a youngster, were you enjoying your days with reckless abandon, swimming, playing with your friends, reading, biking around the neighborhood and getting into delightful mischief? Or were you lying around sighing about being bored?
I think a lot of us have a bias that we have to be the person who’s making the most of every second of free time. We want to be the kid whooping in the summer sunshine and climbing mountains, not the kid who’s bored. Only boring people are bored … right? I don’t think so – no. Those second types of kids are often the same kids who love school. They’re bored in the summer because they miss it. They love structure. They love constantly being challenged. They love quizzes and tests because it gives them a chance to showcase what they can do. And they have the same drive in the working world as adults. Sure, they could figure out something to do with their time if they really had to, but they’re not motivated to because they love the structure that already exists around them, and they thrive in it. Without it, a bleary-eyed malaise kicks in. And for the adults those kids grow into, the same is true for work.
This is kind of blasphemous in the FI community, but I think these people are not just A-ok, but awesome. Those kinds of people are indispensable to the world! They love learning and striving and achieving. No one should ever feel embarrassed to be one of these incredible types of people.
It’s very important to know if that’s you, though. Because if it is, early retirement may not be the best choice for you – whether you’ve achieved FI by working for years or it’s fallen into your lap by luck very suddenly.
Besides looking at your past use of free time, the absolute best way to figure out if you’re someone who will thrive with in a structureless environment is a sabbatical. And I think that’s what anyone with the option for freedom from work should do. (Not right away if you had a sudden windfall. Take a few weeks or even months to keep living your normal life. Let the euphoria of the winnings fade. Let your common sense kick back in.) Carefully plan your sabbatical and have it mimic what you expect early retirement to look like as closely as possible. Don’t go skydiving, tour Europe in the finest fashion, and take a luxury cruise if that’s not what your actual retirement will look like. In other words, don’t test drive the Ferraris of early retirements if your actual early retirement will be a used Honda. Then pull the trigger and see how you like it in the real world. Is it the most glorious few months of your life? Or after just a few weeks, are you itching for something else. Something more … productive. More tangible progress in life.
Then you’ll know for sure, and you can make a careful, informed decision about whether to leave your work behind in a more permanent way.
And hey, remember that if any of this advice about how to handle endless free time applies to you – whether you won the lottery, inherited your wealth, or toiled away for years to achieve FI – you are beyond lucky, my friend. Don’t forget to sit back and be grateful each and every day for that.