What does it actually mean to be free?

OK guys, I did it. After growing a beard and exclusively rocking Air Maxes for three straight years – I smashed the last relic of my corporate existence. The alarm clock. And by flipping that pesky Radar the bird; I’ve come one step closer to the promised land. Freedom.

The non-event

Ah, but if only it were so simple. In fact, I’m writing this post at 4:21 am on Friday morning (my sans-alarm wake up is 5:15; and for those counting, I try to go to sleep by 9:45.) Ditching the alarm clock was a total non-event. Your circadian clock waking you up earlier than your alarm clock would hardly qualify as Freedom. But the proverbial smashing of the alarm clock was enabled by two smaller changes.

Bill Gates told me to read more

Let’s investigate, starting with my former evening routine. Our last child usually falls asleep a little after 8pm. As soon she’s KO’d, I’d race to my laptop for the day’s most important task: getting to Inbox zero. Armed with my toolkit, I approached this mission as if the world’s survival depended upon it.

Once complete, I’d brush my teeth and floss (not this kind) and move to the next part of the regimen: 10 minutes of reading. (Why? Bill Gates says it’s the key to success.) Then, I’d stumble to the finish line (i.e. my bed) and set my alarm, ready to crush the cycle the next day.

Separating cause and effect

Ditching the alarm should qualify as Freedom with a capital “F.” But that actually confuses cause and effect. It was actually the consequence of scrapping my evening routine – two smaller acts of freedom (with a lowercase “f”). And in my many conversations with RadReaders, I’ve noticed a tendency to elephant hunt Freedom. Freedom can come from quitting your job, getting a big bonus, traveling the world, or buying a home. And once the trophy is secured, all of life’s challenges and anxieties will neatly fall in line. Umm, yeah ok. But what if we’re chasing the wrong thing? What if freedom is the consequence of small acts – leaving unread messages in your inbox and accepting that Bill Gates is going to read more damn books than you?

The ultimate freedom: unconstrained world travel

Let’s start with the most cliched acts of corporate rebellion. The Freedom to quit your job to travel the world. (Full disclosure: not only did I do it, I tattooed the flight numbers on my forearm.) It was fun. It wasn’t as expensive as we thought. And we came back with some incredible family memories (and dope Instagrams). But the three months of travel didn’t bring me any closer to determining what I’d do next, nor did it do much to cure the low-grade anxiety that accompanied me on this worldwide jaunt.

It turns out that this wasn’t a unique feeling. In Sean Blanda’s rad piece on sabbaticals, Elena Manho described a similar feeling:

“By month three. I thought, ‘Okay, this is empty, I need to be productive in some way. And then I was talking to a friend of mine … and she says, ‘oh no, no, four months is when you just start to awake. You’re just starting to get rid of all of the bullshit and the anxiety that’s residual from the previous thing you were doing.

Here’s Kyle Chayka on the glamorization of Digital Nomadism:

This nomadic bubble goes beyond a hotel in that it stretches around the world and is built to encompass your entire life; it promises to become your post-geographical home. Yet I found there to also be an anxiety to this hermetic placelessness, no matter how beautifully unburdened or minimalist it appears. Living anywhere is a lot like living nowhere.

It turns out that the Freedom that comes with traveling has long been considered (a suspect) escape route from the things that ail humanity. Here’s another travel-as-a-cureall-hater by the name of Seneca dating back to 4 BC:

“What good has travel of itself ever been able to do anyone? It has never acted as a check on pleasure or a restraining influence on desires; it has never controlled the temper of an angry man or quelled the reckless impulses of a lover; never in fact has it rid the personality of a fault. It has not granted us the gift of judgment, it has not put an end to mistaken attitudes. All it has ever done is distract us for a little while, through the novelty of our surroundings, like children fascinated by something they haven’t come across before. The instability, moreover, of a mind which is seriously unwell, is aggravated by it, the motion itself increasing the fitfulness and restlessness. This explains why people, after setting out for a place with the greatest of enthusiasm, are often more enthusiastic about getting away from it; like migrant birds, they fly on, away even quicker than they came.

A tale of Economy Plus

So if Freedom doesn’t live up to its billing, let’s turn to “lowercase f” freedom. Economy Plus. Say what? Yup, the $59 surcharge has been a lightening rod in our marriage. I’m #TeamMiddleSeat and Lisa’s #TeamEconomyPlus. Wrapped in that $59 fee are some of my deepest insecurities about money: You have to suffer for something to be worthwhile. That vigilance prevents lifestyle creep. And that I’ll make terrible decisions and end up broke in a ditch. Lisa, on the other hand uses hard facts (“You spend more on an iPhone case than Economy plus”) and yet we always fight about it.

Once again, I’m not alone. Bloomberg recently featured frugal retirees who could not get themselves to spend money. These retirees are “fearful of hefty medical bills (…) and don’t know how long they’ll need their savings” despite “reams of data showing that [they] have the resources to weather any realistic scenario.” Imagine that, busting your ass your entire life – then upon retirement, being incapable of enjoying the fruits of your labor. And it’s not just retirees. In my coaching practice, I’m typically encouraging fearful clients to spend more, not less.

Our marriage is now in a good place, and we go for the Economy plus. I take a few deep breaths, just to reaffirm that it won’t ruin us. Lisa’s dread of flying with the two kids gets partially relieved. And our trips no longer start from a place of double-edged resentment.  Now that’s $59 worth of freedom.

Freedom from others’ expectations

Imagine if a Chinese philosopher from 6 BC was implanted into my head and wrote a short poem about what he observed. It turns out that Lao Tzu did just that:

Fill your bowl to the brim
and it will spill.
Keep sharpening your knife
and it will blunt.
Chase after money and security
and your heart will never unclench.
Care about people’s approval
and you will be their prisoner.

Now I could write volumes about the last sentence. The freedom from other’s expectations; from “status games;” competing in “the game of life;” judgement from life choices which defy convention. I’ll save that for another post, but the freedom from others’ approval begins with the intentionality in crafting your own unique story.

Still a damn prisoner

So once you shake others’ expectations, there’s still more freedom to be had? Consider the story of two ex-prisoners of war who meet after many years:

The first one asks, “Have you forgiven your captors yet?” the second man answers, “No, never.”

“Well then,” the first man replies, “they still have you in prison.”

Now, I’m pretty sure that there aren’t any former RadReaders who were POWs, but herein lies the ultimate freedom. Freedom from your own worst thoughts. And there’s one strand of pernicious thoughts that I’m still deeply captive to.

Here’s where it gets “hairy”

I started losing my hair the summer after my junior year at Yale. You may recall that as a teenager, my biggest fear was never falling in love and dying alone. The combination of the two (when you’ve barely formed your adult identity) is pretty gnarly. And to this day, in spite of having found an amazing partner who loves me unconditionally (when we splurge on economy plus), not a day goes by during which I’m not consumed by this physical imperfection. Despite my lame workarounds (strategic positioning so that people don’t stand above my crown, wearing baseball caps often, or pretending to look when the barber spins you around in the chair to show you the back of your haircut) I’m a prisoner to these negative thoughts.

Two decades later, that freedom feels elusive. Impossible. Talking to Lisa about it last year (yes, a decade into our relationship) was nice first step. Sharing this with you, a good second one. So thank you. Anywhoooo – we started with smashing alarm clocks and ended up with male pattern baldness. WTF? Regardless, the path to Freedom (or freedom) doesn’t start with a trip around the world. It starts from within.

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