The “F*ck it” Moment: An Essential Piece to Making Big Decisions

The “F*ck it” Moment: An Essential Piece to Making Big Decisions

Warning: This post says “Fuck” 26 times. Hide ya kids.

People dream up life-changing plans every day.
“I’m going to start my business!”
“I’m going to quit my job and travel the world!”
“I’m breaking up with my boyfriend and moving to San Diego!”
Adrenaline is pumping, images of glory dance through your head; this is really it isn’t it? It’s really going to happen!!
Except it’s probably not.
Ouch. Why?
Because while every day those plans are created, most of them will eventually fade into obscurity while the associated dreamer continues down the same path they swore to leave. The same paths that made them unhappy enough to want a life-changing plan in the first place.
Why does this happen so frequently? Why can’t people, who have the self-awareness to identify that they’re not happy, do anything about it?
I suppose there could be quite a few reasons. 
Maybe you got intimidated by the cost of starting your own business.
Maybe a more enticing job offer came up so you didn’t quit.
Maybe finding an apartment in San Diego turned out to be harder than expected so you decided to stay with your boyfriend. (You laugh, but this is a real one)
There could be a million reasons why anyone doesn’t do anything, even if it’s something they claim would be life-changing.
And when you think about it, it’s really hard to blame anyone for this type of decision. After all, there are a ton of good reasons for not moving forward with a risky decision.
So, with this in mind, how does anyone take the leap into the unknown? How does anyone turn these supposedly life-changing plans into reality?
Easy. They say, “Fuck it”.
They say, “Fuck it”, I’m starting my business.
They say, “Fuck it”, I’m quitting my job and traveling.
They say, “Fuck it”, I’m leaving you.
If plans are ever to become reality, this is among the most vital pieces of the process.
It’s the “Fuck it” Moment.
When you say “Fuck it” in the face of all the good reasons not to. 
“Fuck it” to the comfort. To the guarantees. To the known.
It’s the first step you take into a foreign land – the moment when you decide that no matter what, this is happening.


The Journey to My First “Fuck it” Moment

At the age of 22, I was living in a place called Shirlington. It’s a cozy little corner of Arlington, Virginia – just outside Washington DC (if you’re not familiar, I’d recommend renting a copy of the movie Pleasantville to get an idea).
Fresh out of college, I was working my first salaried job in DC and lived with two great guys in a comfortable, upscale apartment complex. We were within easy walking distance of a Harris Teeter, a movie theater and an entire boulevard of trendy bars, breweries, and restaurants.
I was also in a relationship with a really great girl I had met in college. She lived in Chicago, so we were doing the ‘long-distance thing’ but still saw each other about every month.
Outside of work, my days were filled with happy hours, concerts, intramural sports, tours of DC and more late nights in the Adams Morgan and U Street areas than I can recall (not in small part to my beverage of choice in these areas).
By standard societal metrics, I was doing great. I had a good job, was saving a little money, had a girlfriend, lived in the big city. 
I was on my way to making a good American life.
But you know what? 
I was miserable.
Absolutely. Fucking. Miserable.
I hated my company and being confined to an office all day. I hated drinking as much as I did. I hated the sterile environment of Northern Virginia. I hated the type of relationship being long-distance had created with my girlfriend.
And, not knowing how to handle these strong emotions, it absolutely ate me up inside. 
I had trouble sleeping. Drinking became more of a relief valve than an enjoyable activity. The quality of my work began to fall off.
Why, having put myself into a such a textbook ‘great’ situation, was I so miserable? Was there something wrong with me? Maybe I should just suck it up and maybe these feelings will eventually pass an immature phase of ungratefulness?
I have very little doubt this is the route I would have taken if not for a book called the Four Hour Work Week by Tim Ferriss coming into my life (the full impact of which is best saved for another time). 
Above everything else, what this book provided me was the realization that I didn’t have to live the life I was living. I could choose another life if I wanted to. All I had to do was take action.
But that action was intimidating.
What about everything I’d been taught my entire life? I thought successful people went to school, got a good job, made lots of money, got married, bought a house, watched football on Sundays, etc, etc.
Wouldn’t I be throwing this all away? My career? My relationship? My friends? My home? Everything I’d worked for? 
And it was at this point that it happened; my moment of clarity. I realized that these were all truly legitimate concerns.
I would be, in fact, sacrificing the career path I was on. I would have limited money. I would be moving away from my friends and family. My relationship with my girlfriend would be over. My future would be put in the balance.
But none of that mattered. I was leaving.
In the face of all these good reasons, I was going. And there was nothing anyone could do about it.
This was my “Fuck it” moment.
I quit my job. I subleased my apartment. I broke up with my girlfriend. I bought a one-way ticket to Europe. And I left.
Were there minor panic attacks along the way? Absolutely. Including one on the drive to the airport when I started crying uncontrollably, convinced I was throwing my life away.
But you know what? It was the best decision I’ve ever made.
In part because I had an amazing four-month jaunt around Europe where I had experiences and met people that changed my life forever.
But mostly because it made saying “Fuck it” a part of my life.

Exercising the Muscle

Like most other habits that make your life better, saying “Fuck it” is not something that comes naturally.
For the past 200,000 years, humans who behaved conservatively were typically the ones who stayed alive. The ones who said “Fuck it” and took their chances in a sabertooth tiger den typically did not.
The very thing that has kept us alive over the past two hundred millennia is the very thing that’s preventing us from acting on our dreams. Not only are we battling societal pressure to act a certain way, we’re also battling our own DNA.
So how are we supposed to overcome this?
The same way you get to Carnegie Hall…practice!
The only way to get comfortable taking the leap on big decisions is to practice with smaller ones. Not every one of these moments has to be life-changing. You can (and should) practice this nifty little tool in less impactful situations.
For some people, this could be simply starting a conversation with a stranger despite your inner introvert screaming in protest.
For others, it could be driving to a part of your city you’ve never visited and searching out a good restaurant.
Perhaps broaching a topic with your significant other that you were previously too nervous to bring up.
Or maybe there’s a blog post you decide to finally publish after you’ve been putting off for months out of fear that people will think it’s stupid (ahem).
Indian philosopher Jiddu Krishnamurti once said, “One is never afraid of the unknown; one is afraid of the known coming to an end”.
It’s about becoming more comfortable with the known coming to an end; that’s what saying “Fuck it” is really all about. And the more you continue to exercise that muscle, the easier the big decisions will feel.


An Australian Love Story…Sort Of

After my first “Fuck it” landed me on an unforgettable European adventure, I’ve tried my best to make it a regular practice. 
These leaps have led to some of the most cherished experiences in my life including a year-long trip around the world, a wonderfully fun job and a new life in Denver. 
But it’s not these situations that I want to examine.
There’s one with a different ending which makes an essential point, and it involves a love story (sort of) with an Australian girl I met in Spain. Let’s call her Maggie.
Our story began in San Sebastian; a gorgeous beach town on the country’s northern coast, just a short train ride from the French border.
Having my sights set on Madrid to the south, I planned to spend two days but ended up staying seven. The distinctly Spanish blend of delicious food, great music, beautiful beaches and amazing people was more than I could resist; I couldn’t get enough.
My encounter with Maggie began with a glance as we passed on the cobblestones streets of the old city. It continued into a sangria-fueled romantic tryst lasting until the early hours of the morning. 
Maybe it was the sangria or maybe it was her accent or maybe a little bit of both, but it felt like we had a real connection.
We decided to retire to her hotel where I was devastatingly denied entrance by the proprietor (whom I attempted to bribe with 50E, despite being on a budget of approximately 15E per day). I stumbled back to my hostel for a couple hours of sleep, dejected but excited to meet again in the morning.
Having my rise the next morning delayed by the large amount of sangria still pulsing through my system, Maggie left the city before I could run back over to her hotel. 
The front desk attendant of the hotel said I missed her by a mere 5 minutes. I sprinted out into the streets in search of her, but to no avail.
I didn’t have her number. I wasn’t quite sure I knew her last name. I was quite sure I’d never see her again.
I thought there was a pretty good chance I had just lost the love of my life. I was devastated.
But through the miracle of technology, I found her on Facebook and sent a series of cheesy messages telling her how I felt which, despite breaking the golden rule of not expressing emotion over a digital medium, somehow elicited a positive response from her.
We kept in touch over the next few months until, brazen with my newfound “Fuck it” bravado, I decided to book a flight to Australia to visit her. 
And, because my e-commerce company was still in it’s early stages, I would be going without a paycheck for that period.
But “Fuck it” right??
To cut a long story short, the trip to Australia was an absolute disaster. 
After the first 24-hours it was painfully clear to both of us that in no way did we enjoy each other’s company. Things got really awkward really fast.
Try to remember the most awkward date you’ve ever been on. 
And then try to imagine that date being 14 days long in a country 10,000 miles away.
And then try to imagine that date taking place at her mom’s house (who also doesn’t like you).
Horrible may be too fluffy of a term.
Every day, I just started throwing myself out into the scorching Australian summer heat for hours of running/walking/wandering/being-anywhere-else-but-there.
I’m actually chuckling about it to myself now – but at the time, it was terrible. Really, truly fucking terrible.
Now, why did I bring this up? And why did I drone on about this disaster instead of the successful ones?
Because something very rare happened in this situation; the worst case scenario came true. And it’s absolutely vital to highlight that saying “Fuck it” will not always have a happy ending…
…but that should never be a reason to shy away.
Despite this particular situation turning out horrendously (Maggie and I have not spoken since), I made it through and am better for it.
How could I possibly have become better from such a dumpster fire?
Well, before this experience, my confidence was pretty low – particularly with women. I often had trouble mustering the courage to speak with them at bars or pursue them in any context (My introduction to Maggie was actually made by my outgoing travel companion, not by me).
But for some reason, after this trip, all that changed.
All of a sudden, after putting it all on the line to pursue someone on the other side of the world, approaching a woman at home didn’t seem like such a big deal.
I became a much more confident version of myself and embarked on the path that led me to the real love of my life just a couple years later. And while this adventure turned out just about as far from what I expected as possible, I shudder to think what my life would be like without it. 
Plus it’s not a bad story to tell.


What’s the worst that could happen?

So now that I’ve spent the past two thousand words arguing why you should say “Fuck it”, here’s a couple thoughts on why you shouldn’t.
While this tool is meant to develop confidence in the face of daunting choices, it’s not meant to be used without consideration. 
Decisions have real consequences and they don’t always just impact you.
One wonderful example of when not to say “Fuck it” would be a man with a wife and three young children who wants to leave and travel the world alone. While it may be a dream of his, this decision will inflict serious harm on others in his life.
So let’s make that criteria A for saying “Fuck it” – No harm will be inflicted on others by your decision.
Now that we’ve taken care of the bystanders, what about you? Aren’t you the one most likely to face harm by your decision?
The answer could absolutely be yes. Jumping, untethered from a tall building would be an example of a bad result of saying “Fuck it”. So how can you tease out the few truly damaging ideas from the vast pool of those that are only surface-level scary?
Fortunately, there’s a simple litmus test and it comes Tim Ferriss.
When facing a big decision, Tim asks himself a simple question: “What’s the worst that could happen?”
This powerful question does one of two things. 
It either emasculates surface-level fears and empowers a person to move forward OR it knocks some sense into a situation where you were considering something that had the potential to be truly damaging (i.e. jumping untethered from a building).
If you’re unsure, write Tim’s question at the top of a journal page and go crazy with your worst case. It’s usually not that bad but is certainly worth catching when it is.


The Journey Begins

Whether it’s quitting a job or leaving a partner or embarking on a journey – you will be departing from the known into the (sometimes really fucking scary) realm of the unknown. 
But while your endeavor may be intimidating with no clear end in sight, the only way to ensure you fail is to never start.
So “Fuck it”, get out there and enjoy the journey.
Posted by on February 4, 2018


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