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3 Questions I Asked Before I Quit My Job and Traveled the World

Almost a year and a half ago now, I trembled as I walked into my manager’s office, mouth dry and hands so, so sweaty from the terror of the two weeks’ notice I was about to submit.

Hours before, I tried my hardest to make it seem like just another day to my co-workers. For them, I think it was business as usual: we sipped coffee and made jokes about PhotoShop’ing nipples (the usual conversation fodder); and they were none the wiser. For me, I sat in quiet turmoil, playing the conversation I had planned with my manager over and over in my head, all the while fighting every fiber of my being to not chicken out. It was crazy.

I felt like such an idiot leaving a fantastic job, where I worked with an amazing team, got to work out whenever I wanted, had much freedom in what I did within the company, and generally sat really damn pretty.

To make matters worse, I never sent a warning email to my manager. I never indicated that we “needed to talk” or anything. His open-door policy sometimes worked in my favor, but that day it seemed like a test for my resolve. The conversation itself was already hard enough, but did I have the guts to peel my ass off my chair, walk 20 steps to his office, and knock?

Up until that moment, I watched whenever my manager left his office and guessed whether it was for lunch, a meeting, or just for a cup of coffee–much like a creepy stalker. I agonized over when he would be settled in his office long enough to be receptive to a drop-in meeting while also trying to anticipate if it’d be a good time to drop such a bomb. (Pro-tip: I don’t think there’s ever a good time for these things.)

And finally, without knowing it, I invoked the power of “Fuck Yes! Saturday” to tell myself that if I didn’t put on my big girl pants now and take the leap, I’d just be prolonging the time I’d feel exactly as insane as this. It’s time to buck up or shut up; do or die…and try not to puke.

I shakily closed the door to his office behind me, slumped into the chair that sat a mere two feet from him, and took a deep breath. Then as if on cue, the world flashed white…

Caught some dude paragliding down the mountain I was hiking in San Jose, CA.

Now I’d be lying if I told you I had an Office Space moment, where I didn’t give a damn and wore a triumphant I’m-too-cool-for-school smile afterward. In reality, I slinked back to my desk and simply felt worse than ever.

Quitting your job isn’t something to take lightly. It certainly wasn’t for me. For the same obvious reasons you probably think about. All those movies and shows about misfits in a corporate culture, where the protagonist indignantly quits his or her job and struts out of the office in a flippant manner, should be taken about as seriously as fairy tales. Unless you want to commit career suicide. Severing professional ties is never easy, but there is an elegant way to do it.

Giving two weeks’ (at least) is standard practice, and that’s minimum. There’s more, but I don’t want to tell you the best way to quit your job. I’m not here to say that everyone could or should do it anyway. The reality is, entrepreneurship, nomadic life, or independence in general isn’t for everyone. Rather, my goal here is to share my insight on how to ground your decision in pragmatism.

Whatever the case, it’s important to recognize the valuable skills, resources, and connections you’ve gained during your employment–whether it was being a shift manager at Starbucks or an intern at a porn studio. So many people can’t see past their misery and thoughts of “What should I dooooooooo?” to realize their time with any company was a huge personal boon. If you learned how to write an email that people actually read, for example, because you had to send out 50 emails a day and hated every one of them, that’s a valuable fucking skill, believe it or not.

I choose to look at this with gratitude. I genuinely do not regret a single minute I spent building the experiences, relationships, skills, and world-views that serve me now. I worked hard, but I won’t for a second fail to see how many opportunities and connections were afforded to me through my former employers.

When I finally put in my two weeks’ notice, the conversation with my manager went better than I’d expected. He was curious about my plans, to which I meekly responded with something about freelance work, video, and blog stuff. I tried to sound confident, but I could see in his eyes that he thought I was about to hit some hard times. I don’t blame him, but in all reality, I felt semi-prepared for the road ahead, although at the time I had little idea how exactly it would twist and turn.

Before waltzing into my manager’s office that day, I made many pragmatic calculations to make my decision to quit (with no other full-time gig) less pants-shitting. It came down to three questions:

Question 1. What Was My “Freedom Number”?

I cribbed the name of “freedom number” from my friend Jonathan Goodman. At the time, I didn’t call it that, but what I did was the same: I calculated how much money I needed every month to meet my basic needs. This included rent, bills, food, and miscellaneous.

The hamster wheel in my head squeaked ahead: I had no dependents. I had paid off my school and car debts long ago. If I moved back home, I could cut down on my rent cost, contributing half the cost of normal (I’m not a complete freeloader), but then my car insurance would increase because it’s Los Angeles and everyone is a shitty driver (yes, even you) so that evens things out. I needed a phone and internet for freelance work. Plus, there was no way I’d be a Debbie Downer and never go out, so I made sure to allocate a reasonable amount of funds to entertainment and dining.

All in all, my monthly cost came out to be about $1,300 a month for rent, food, and bills. It’s fairly low because, as I noted, I’d move back home for reduced rent and utilities, and have no one else to spend money on. There was still plenty of cushion in this amount for me to be a bit flexible. Jonathan’s was $2,600 because his rent was high and he had a girlfriend.

What this freedom number–$1,300–gave me was the opportunity to explore, test things out, and possibly even fail. I think that’s the best sort of freedom many of us can hope for. Your freedom number isn’t an exact science. Don’t spend too long on your freedom number. What’s more important is that you now have a monthly goal.

Question 2. How Could I Make That Money?

Once you know how much you need, your brain energy can be devoted to coming up with the money to reach that freedom number. Maybe you dig into your old resources and contacts to see what opportunities are available. Maybe you start shedding some things you don’t need anyway and sell those. Maybe you play online poker or baccarat (I have friends who make a ton of money in these games). Maybe you end up getting really creative doing–oh, I don’t know I can’t give all the ideas here. There are seriously a ton of options; just watch Gary Vaynerchuk for a kick in the ass and some ideas.

Some people choose to lean on their savings at this point. I’d say that’s not the brightest idea. If you simply relied on your savings as a safety net with the thought of “How long can my savings float me?” you’re immediately handicapped and putting a really stressful time limit on yourself. Sure, that’s what “rainy day” savings are for, but there are a few reasons I don’t think savings here help you.

The first reason is obvious: you’d deplete your hard-earned savings. The second is, you set yourself up to dick around because you don’t use your noodle to think about how to leverage your existing talents, resources, tools (online and offline), and the people in your life. Worse, you dare not to try the very things that scared you while you still had a cushy job, so what’s the point of quitting then?

I will forever remember reading this advice from Rich Dad, Poor Dad, where the author shared his dismay over his “poor dad’s” saying he couldn’t afford something. Want to buy a new toy? Car? Air conditioner? “We can’t afford it.” By saying he “can’t” afford something, according to the author, he resigns himself to a mindset in which he has no control over his money. But if we flip that and ask, “How can we afford it?” instead we spark a whole new line of thought–one that leads us to charge toward the opportunities and creative possibilities to make it happen.

When faced with my freedom number, I knew that I had my weekly articles with Lifehacker.com, though at the time I was only doing two or three articles a week. I calculated how much that netted me a month, weighed the potential of how much more work I could get and what else I could do, and came up with a surprising number of avenues. Additionally, I was fortunate that upon departing my manager had guaranteed me a certain amount of work every month. Luckily for me, I was going to be more than okay.

Maybe you don’t have freelance gigs lined up. There’s no shame in taking up part-time jobs if you need to. The point is, be pragmatic. Be especially realistic about how long you can sustain a certain cashflow.

Question 3. If I Didn’t Make This Decision, What Could Change to Make Me Happier?

It’s easy and cathartic to talk about how much you want to be doing something else. Fantasizing is nice. Dreams feel like being wrapped in a warm burrito. It’s an illusory feeling of progress, or a form of escapism. Whatever it is, it’s a waste of time.

The longer you wait, the less things change and the more you agonize. At least, that was how I felt. At first, I was okay because I felt like I still had much runway for learning and growing (and I did!). Eventually, I had to weigh the benefits of my professional growth against the mental anguish from my developing depression. You have to understand that I moved from California, where I lived all my life, to be by myself in Boise, Idaho–among the wilderness, the gun lovers, and potato jokes–for nearly two years.

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Granted, I had chosen to move there and I could’ve controlled how many times I flew back to see friends and family; but eventually, there came a point when enough “self-imposed isolation” was enough.

There were definitely many times when I’d assess my situation, realize the fortunate position I was in (Boise was, in fact, a great place to live), get cold feet, and think, “Maybe things will get better if I just wait it out.” But that was a big, fat lie to put off the inevitable. When I honestly looked at myself and asked, “What could I change here to make myself happier?”, the answer was: family.

But I was alone and had been held back by my mindset that Boise would be a temporary home. Unless I hooked up with someone and made babies immediately (not in my current plans, if we’re being honest here) and flew my parents to Idaho, the answer was stark clear.

There was also a little nudge from the pending winter season. I knew that if I didn’t pull the trigger within a small window of time, I’d run into a lot of trouble moving my stuff back to California when winter finally arrived. So I was left with the choice of braving the winter roads with all of my possessions; or holding out for another five months or so. And to really seal the deal, I had bought a one-way ticket to Tokyo.

Of course, quitting and moving (again) terrified me. It was a big, wide open road. Literally and metaphorically. In the beginning, being a nomad wasn’t in the cards, or something I had really thought of as an option–simply because I didn’t know how. I just knew that my freedom was possible. It wasn’t until I’d arrived in Tokyo that I realized how cheap it was to travel around Asia. There were so many parts of Asia I had never visited before but always wanted to, so I kept extending my stay and I guess that’s when the nomad thing stuck.

The rest is history, folks.

This is just my story, and by no means should it be a roadmap for you. I will say one thing, however. If you’re still wondering whether you should quit or not, the most important thing is to not have an ego about it. Unless you have a thriving online business or are flushed with cash, do what the fuck you gotta do. Self-esteem is a double-edged sword. A friend–I can’t remember who now–once told me that if you’re scared to do something because that might be the wrong decision, then just maybe…that’s the right thing to do.

Take that as you will.

Freedom is a pretty elusive concept. I think people fall in love with the idea of a highly romanticized version of freedom–they picture someone waving their country’s flag, a person sitting on a beach sipping pina coladas, or maybe a picture of someone laughing gleefully at their salad. In reality, it means different things to different people in different parts of the world, but freedom is for all intents and purposes universally understood as being unbound. Unbound by grey, sterile cubicle farms and fears–of any kind.

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