Retiring TO, Not FROM

Fill in the blank: “Once I have ______, I’ll be happy.”

So many people on the road to Financial Independence successfully hoodwink themselves into thinking that once they have 25x their annual expenses (or 33x, or whatever floats your boat), they can flip the bird to their boss and head out to their glorious alarm-clock-free happily ever after.

What will they do with all that time? “WHO CARES? Whatever I want!”

Sounds pretty great for a couple weeks, or maybe even a couple months. Particularly for those who need some time to detox from noxious work or unpleasant coworkers.

When It Gets Stale

However, this freedom can sour quickly if you don’t make good use of it. After kicking it on the beach for a while, most of us are ready to do something productive. Once the shine comes off this dash of independence, we tend to find drama to fill in for the drama we didn’t know we missed at work. The initial stages of retirement can be tough on self-image, mental health, and even your marriage.

We might not know it, but we rely on some form of productive labor to keep us sharp, engaged, and connected to the world around us. We need a place to be and to belong. Whether this is a feature or a bug of our human nature is unimportant. It just is.

Too Much Freedom

When I was still at my 7-to-5 job, so many decisions were made for me. If I wanted to both exercise and see my family, I had to work out before work. The structure of a standard workday benefited me by making my decisions for me.

Being an entrepreneur is a different story. Regardless of whether working out first thing in the morning is the best solution for me, it is much harder to self-motivate and get that done, as there is always some exigency to suggest that it “just doesn’t make sense today”. For me, the reduction in structure resulting from my transition took a while to get used to. And I’m working hard at my own initiative. Without that remaining structure, I might well be adrift.

Imagine waking up to a day in which there is no project for you to accomplish. At first, it sounds delicious, but after 50 days just like that, there’s a good chance you’d just get used to it. And once you’ve fished out the bottom of the barrel on Netflix, you’re just plain bored. Not only that, but you lose your edge, and your productivity is sapped by a lack of urgency. There’s a reason why it’s common knowledge that if you want something done you should give it to a busy person.

Running Away

If your job is abhorrent, it’s understandable that you may feel that in order to figure out what you want to do next, you need to take some time off and clear your head. But gritting your teeth and sprinting as fast as you can to that head-clearing opportunity is just accepting unhappiness in the interim. When your heart is set on retiring from, your reserves of energy are quickly depleted and you’re at serious risk of burning out.

Running Toward

On the other hand, if you’ve figured out your why, what you’re retiring to, then even the distasteful work in which you’re presently engaged assumes new meaning.

Like the boy in the crystal shop in Paulo Coelho’s “The Alchemist,” you’re not just polishing crystal, you’re working toward finding your treasure.

Like the fabled NASA janitor being questioned by JFK, you’re not mopping floors, you’re helping to put a man on the moon.

Engagement

When you’re firing on all cylinders, the impact is great within the rest of your life. As Emerson put it, “When the mind is braced by labor and invention, the page of whatever book we read becomes manifold with allusion.” Work is healthy, and engagement with work enlivens our ability to learn from other experiences outside of work.

Ambition is a bit of a dirty word in some circles, but there is an inherently appealing essence within it. The conviction of knowing what you want shines through in your resoluteness, and people around you take notice.

It’s not about achieving gain, fame, or praise, but about being a truer version of yourself, adhering to the optimal version of you, who is waiting to be revealed.

Self-Possession

When you know what you’re striving toward, you assume the character of one who is sure of what he wants. Rumi describes this state aptly,

“Beyond opinion and judgment, undistracted by guilt,

I am walking strong and steadily home,

Not timid or uncertain,

with my eyes splendidly clear,

all one pearl of gratefulness, no fear.”

But How?

That sounds like a delicious state, but you’d be forgiven for thinking, “Okay Ben, so your solution to not knowing what to do next is what, just figure out what you want to do next, and then you’re all set?”

Not quite. Acknowledging the problem (you don’t know what to do next) is half the battle. Then you must set out to find something worth retiring to. How? By searching diligently. When a problem is hard, do we throw up our hands and give up? Or do we roll up our sleeves and try harder?

Start Here

Learn a new skill. Play an instrument, learn a language, create art, write code, get in shape. Do something you’ve never done before. Experience and document the transformation from being someone who “doesn’t know anything about this” to someone who is making progress at upending that self-assessment. There is something breathtaking about waking up as someone who “can’t do this” and going to bed as someone who just did.

For me it was learning to code. For you it might be something totally different. Pursue the sweet spot in life on the frontier of your capabilities, one foot firmly planted in your zone of competence and the other boldly pressing forward into the unknown.

When you begin to see yourself as someone capable of learning new skills, the tunnel vision you apply to life is relaxed, and the world becomes a bigger place brimming with opportunities for those willing to take them in hand.

And hey, even if it takes a while to figure out what sets you ablaze and is worth running toward, it beats the heck out of unhappily waiting for a day when you’re older and more tired to embark on the exact same quest. See you on the frontier.

Ben Miller

Founder of ChroniFI

December 2021

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The foregoing are the opinions of the author and are for educational purposes only. They do not represent professional financial or investment advice. For financial advice, please consult a licensed financial professional.