ramblings & exploration

Why It Took Two Years To Leave My Job (How to Confront Fear To Do It Sooner)

I was afraid. It was fear, plain and simple. I couldn’t pinpoint it at the time, but the fear was like a chameleon. It took on a different appearance in order to fly under the radar and stay unconfronted, unchallenged and therefore, unchanged.

The fear is real

I think it wise to not shy away, but instead start my explanation by wrestling the very real, but often disguised concept of fear. Addressing this first is the only way I’ve found to gaining forward momentum.

Not exactly the elephant in the room

Fear stops you in your tracks and makes you hesitate. It prevents you from taking any action. Fear hides itself. It pretends to be a lack of confidence. It masks itself as inability. It gets mistaken for rationality and eventually it embeds itself in a decision that appears to be the only logical option available.

Fear is not always bad, however. In evolutionary terms, fear helps man avoid disaster. But this innate, split-second fear of dangerous situations (that brown bear clawing your face off) is a different brand of fear than what I’m going after.

Unproductive fear

The fear I’m interested in prevents you from taking any sort of risk that might involve an unknown outcome or result in failure. It’s more of a modern-day fear. It’s the type of fear that occurs after your physiological needs have been met and you have the luxury of contemplating your future.

It’s this fear that kept me from pursuing opportunities that I should’ve pursued.

Disguised in comfort

In my case it was a typical office setting that was masking my fears and keeping me comfortable. It was cozy and it was safe. It was something to hold on to because letting go would mean risking a little bit of myself and becoming uncomfortable.

This feeling multiplied because I didn’t know what I wanted to do. I certainly knew what I didn’t want to do—work in a confined space for nine hours a day, doing work I was growing less interested in by the day. But I hadn’t pinned down the ideal job, interest or cause that I wanted to pursue.

Ask questions

That’s a tricky thing to come to terms with. You desperately want to get out of your current situation, but haven’t an idea of what it is you’d like to replace it with. How will you spend your time? What if the new venture doesn’t pan out and you’re even less excited about it? This would be even worse because now you’re out of a job and in an even less than ideal situation than before.

However, this idea of guessing where you will end up, what you will do and the outcome it will have before even stepping up the the plate is step number one for inaction. It’s a snowball from hell (if there is such a thing) and it builds and collects future-failure and builds and increases fear until it’s so damn big that you’re overwhelmed and put the idea of a change completely out of mind.

A tiger cub playing in the snow with a snowball twice its size

Then do something about it

That snowball was the root of my problems. I’d build up a huge list of reasons why it wouldn’t work out and how silly I’d feel after wasting my time. It never occurred to me that this rationalization of why I shouldn’t or couldn’t make a change might not be so rational after all.

What I mean to say is I was mostly thinking of the negative aspects of a change, without giving much credit to the possibility of growth, learning, personal development and maybe even success. It was a pros and cons list that was missing the pros.

I began to confront this irrational way of considering my options. I started to make an argument against negative outcomes that could occur and took a balanced viewpoint on my ideas. It felt strange to play devil’s advocate in this way.

Irrationality in decision making

This process might seem obvious in hindsight. However, most people are risk averse. Faced with a decision between a guaranteed outcome of $50, or a coin flip with outcomes of $0 or $100, most people tend to choose the guaranteed $50, despite both scenarios having expected returns of $50. Some would be even willing to take less, let’s say a guarantee of $30, instead of the uncertain $100. 1

We have a tendency to view any new challenge as a chance for failure and don’t give success a chance. We shoot down the idea of making a change because we would rather hold on to what it is we have now, instead of taking a risk and considering how we’d pull ourselves back up from defeat.

We seek to maintain an equilibrium.

Shit happens

A new responsibility or commitment in the form of a job change (or loss) throws us off our game and we do whatever it takes to counter this and find that balance again. The loss of a loved one or a break-in during the night takes us on an emotional ride and we are trying once more to get back on level ground.

A lot of these outcomes, however, we don’t have much control over.

Unless you’re the CEO or another top executive, your company going bankrupt and thus putting you out of work has little to do with the choices you made. Losing a loved one is difficult, but it’s part a certain fact of life and (usually) can’t be prevented. Someone breaking into your house, robbing you and scaring the bajeezus out of you is likely not your fault, but shakes you up nonetheless and makes you paranoid about it happening again.

Your balance is thrown off after experiences like these.

You file for unemployment and straighten up your resume. You mourn death and evaluate your own life. You triple check the locks and leave on every light each night.

Resiliency is a product of adversity

But the beauty of our nature is that we eventually correct course and improve our resiliency along the way. We didn’t ask for these things to happen. They just did. And then we found a way to manage. We likely came out stronger than before.

These events are important to consider. Knowing that they’re out of your control allows you a certain freedom to go about your life without constantly worrying about every terrible situation you could face. Possibly more important to consider, however, is that you’re likely doing everything within your power to avoid obstacles and uncertain situations that you can control.

Change is a long-term strategy

This is what makes change so difficult. There’s a real threat to ourselves when we set out to “self-inflict” a type of change. Ending a long relationship is a choice made more difficult because the world doesn’t do it for you. You have to take that risk. You’re leaving something you’ve come to know very well and become comfortable with. You feel an uncertainty that you’re making the right choice and that you won’t find anyone else. That’s why breakups are difficult. You want to avoid the emotion and the heartache of moving on and facing uncertainty once again.

Therefore, the most important thing I began considering was the growth potential that any new challenge would present. I began to look at my past challenges, both with successful and unsuccessful outcomes. But, I started to focus less on the outcome and more on the experience and learnings along the way.

This was more than a subtle change. It required practice to override my instinct to focus on the outcome. Instead I looked to direct my attention to the process which would produce the outcome.

Stones wind their way through a creek. Looking at A and Z without seeing the steps in between is one aspect of fear.

Missing the forest for the trees

It’s overwhelming to solely look at steps A and Z and ignore the stages in between. That’s why training for a marathon seems daunting. You can run a mile, sure. But how about 26? No one goes from one to 26 overnight. There’s mileage along the way that often gets forgotten when you focus only on the seemingly impossible end.

This change in thinking helped me stop that snowball from hell, the one that kept growing with negativity, self-doubt and failure. Fear was now a tool that I had which allowed me to initiate growth. It was an instrument I could use for self-development. And fear was also something I could point to and associate with my hesitation to leave. Fear became an almost tangible thing that could be confronted, challenged and eventually used to my advantage.

Follow the money

This post would be insincere and untruthful though if I only discussed the idea of fear as the source of my reservations to quit. Luckily, the next part was super easy to identify and then quantify.

The logics is as follows: No job equals no money.

Nothing earth-shattering here. But from a practical standpoint, this was something entirely different than confronting fear and has its own implications. No landlord was going to let me live for free because I had confronted my fears and had decided to act. The grocery store didn’t care about this either. I couldn’t buy food with a realization and change of attitude.

Two options

One way to go was to make more money. I already had a full-time job. Taking on a small side business was an idea, but nothing of substance ever came from my tinkering.

The route I chose was saving. Not a novel concept by any stretch of the imagination, but it is something that a lot of people can’t, or don’t care to figure out. Indications of this are easily found in the U.S. consumer debt.

Broke is no joke

Collective American debt is currently at over $12 trillion, with over $1 trillion stemming from “revolving” credit card debt. We really do a good job of going above and beyond spending what we’re capable of affording. This problem is further reflected in amount of savings the average American has—the median savings of all working-age families in 2013 was only $5,000 ($60,000 for families with a savings account). 2

An entire post could be spent on the frivolous things we buy, how the need-it-now culture is insane and how we are generally not saving enough for the future. But I’d rather save my time and later direct you to useful links already written on such issues.

Calculating your comfort zone

It didn’t take me two years to calculate the finances. This I tackled early. I came up with a number that I was comfortable with. My comfort level was somewhere close to a year of living expenses. I figured that this amount of time would be sufficient to find something more interesting or go broke. 3 I looked at where I might be able to cut corners on spending without becoming obsessive. I started using spreadsheets to track expenses and better manage my money.

There was a caveat with this savings figure, however. It represented the cost of living in a medium-sized metro area in the United States. I had bound myself to my home boarders and hadn’t considered looking overseas for opportunity. The whole world was open and I was only playing in Uncle Sam’s sandbox.

A passport truly opens doors

I started researching the cost of living throughout other parts of the globe. If I stayed away from Western and Northern Europe, Australia, Japan, Canada and a few others, I could live comfortably for up to twice as long in other parts of the world.

And just like that my time horizon had expanded in terms of how long I could “survive” without proper work. It also served to scratch another itch I had—living in a foreign country and learning a new language.

It turned out that a combination of aggressive savings and good old-fashioned arbitrage was the ultimate hack to leaving my desk job and having more confidence in doing it.

I thought that my anxiety about leaving would somewhat subside after hitting a home-run with my arbitrage revelation. But instead it proved to increase this feeling.

A sailboat crosses through a channel with a steep rock face sloping on one side. The vast amount of places you can go can often cause fear from choosing the wrong destination.

Book it and go

The fact that I could set sail and go almost anywhere in the world began to get to me. It was like being in the grocery store and walking down the cereal aisle. There’s 47 choices which only serves to leave you feeling overwhelmed and less satisfied when you eventually do make a choice. I was having buyer’s remorse, but with something a little more serious than cereal.

This specific dilemma was a bit irrational, though. With the proper savings, even so much as an entire country change wouldn’t set me back too far. Sure, it wasn’t as easy as finishing the Fruit Loops and then buying Cocoa Puffs the next time, but buying another plane (or bus) ticket and possibly leaving a prearranged apartment early could be managed without much trouble.

Life doesn’t care about your plans

Since I had the time, I didn’t want there to be any flaws and tried to plan meticulously. I was wrapped up in planning the perfect escape. At the time, all the plans I was making seemed permanent. This obviously was not the reality. The only certainty to these plans was leaving my job. Any hiccups could be cured without much headache and might be considered only a small setback, if they even occurred at all.

If I stress one point in this post it is that most of the outcomes from decisions you make are not permanent (even that ugly tattoo on your arm). The best thing you can do is acknowledge and then ignore the what if’s. They will turn your brain against itself in a relentless game of ping-pong and drive you insane. With a bit of basic planning, you can set yourself up to have the ability to handle these unforeseen challenges.

Probably better off asking the magic 8-ball

Again, this ties back into the problem I was having before of focusing too much on the outcome. I was trying to predict the success or failure of myself in a new country. Would I do better in a small, beachside town, or a large, urban setting? The reality, however, is that whether good or bad, I had relatively little idea what would happen after the plane touched down.

The reason is straightforward. There are millions of decisions that would occur between my arrival and some distant outcome that I was trying to predict. The residence I chose. The people I associated with. The work or projects I took up. These all make up the process. But they are independent actions. No single decision was going to make or break the experience. The sooner I figured this out, the easier it was to regain my focus at work and begin to shed the anxiety of leaving.

Almost there

Up to this point I had slowly started the process of identifying and dealing with my fear. The fear of the unknown. The fear of leaving my comfortable work arrangement. I also developed a plan to get my finances in check so that I could weather the unemployment storm I was about to face.

Listen to others, but trust yourself

But apprehension was still kicking me around. It turns out that there was one last hurdle I needed to get over. This issue tends to surface more strongly in some than others. It’s the internal battle of facing your critics and finding a way to answer only to yourself and to no one else’s expectations of you.

I was still struggling with what others—family, peers, co-workers—would think. Some would assess my situation and tell me I was crazy or making a mistake. They didn’t understand the reason behind leaving something certain to pursue something unknown.

Some did understand my frustration with the typical work culture in the United States, but few were able to offer suggestions, short of finding a different job in the same type of environment.

I began second guessing my decisions. How could most of the people in my life be wrong? Was I right to ignore their warnings? I heard, “Oh you should stick with what you have because what if you can’t find another job?”. Or “That unemployment gap is going to look bad on your resume; what will you say to employers?”.

The problem with most people’s logic

The problem with this line of thinking was that all their rationale was focused on what-if’s and unknown outcomes. They were only seeing what I was giving up by leaving. Nobody seemed to consider what I was giving up by staying in my current role and foregoing other opportunities.

What if I can’t find another job? Trying to predict the labor market in X years and guessing my ability to get another job seemed a bit outside of their capacity.

The obvious question and its related assumption

What would I say to employers? Any employer who is shortsighted enough to look at a gap and not consider what occurred during that gap is not someone I’d like to work for.

It would be completely different, however, if I was probed for an explanation and all I could muster was that I visited a few countries and tried loads of new food. As long as I was developing myself, learning a new set of skills and actually contributing to something I found meaningful, then I wouldn’t have a problem discussing that gap.

Discussing the gap on your resume

What’s more is that these questions assumed that I’d actually like another job with the same structure. It neglected the fact the self-employment was a possibility. To me these points seemed shortsighted and reflected only personal desires regarding employment.

Are you even qualified?

Still, people’s opinions matter to us. We seek other’s approval and look for acceptance of our ideas from them. This is what made it so difficult. I was seeking advice from people who had never done what I was interested in doing. HINT: seek out others who are doing what you want to do. I think a lot of people questioned my decisions because they in fact couldn’t see themselves doing it.

This of course is only natural. You are the baseline for comparison to your peers. Any time someone proposes something you’re unfamiliar or uncomfortable with, you imagine yourself in that situation and some of your insecurities and vulnerabilities begin to emerge.

It’s not to say that these people didn’t have good intentions. I don’t believe that anyone went out of their way to offer poor advice, or tried to persuade me to abandon my decision. Most were just uncertain of what to say, so they repeated what others in the past had said. They were repeating advice that seemed the most logical and available.

If you’re not helping, you’re in the way

Discussing my plans seemed a bit dangerous now. The available information to most people was reflected in the average of their experiences. Anything outside this average or this norm proved difficult grounds on which to offer guidance or understanding.

So I stopped asking. I stopped discussing. I stopped caring what others would think. This proved to be another important habit I tried to develop and it helped me tremendously as my exit date approached. I ignored anyone who couldn’t get behind me. It took this sort of blind confidence to shake the final bit of anxiety I was having about leaving.

Let fear motivate you

There isn’t a roadmap or a 10-step guide to leaving a job. It’s uncertain what will happen when you leave and what awaits you when you do.

I can only offer advice on what I did. How I acknowledged my fear of uncertainty and tried to combat it. How I began to focus less on the outcome and more on the process and development potential along the way. The safety net of sorts I set up to assure myself that I wouldn’t be on the streets in a month. And the tunnel vision that I adopted in order to avoid other’s insecurities and prevent them from manifesting inside myself.

The last bit

My final advice would be to make a decision when you have a clear head—first thing when you wake up, perhaps. You don’t want to be persuaded by anything you’ve seen or heard that day. Just your own thoughts.

Manjushri in Buddhism is cast as a silhouette.

Ask yourself what you really want. If it isn’t what you currently have, then make a plan to change. Set a date, first. Then shorten that date. Trust me. You don’t want to give yourself time to dwell on what-if’s. That time spent in “limbo” after making the decision and setting that date will weigh on you, so aim for as short of a window as possible.



  1. Wikipedia does a wonderful job of breaking down risk aversion and links to three sources detailing the portion above that I attempted to summarize. You can find more info. in the studies from Mr Lev Virine; Mr Michael Trumper (28 October 2013). ProjectThink: Why Good Managers Make Poor Project Choices. Gower Publishing, Ltd. ISBN 978-1-4724-0403-9; from David Hillson; Ruth Murray-Webster (2007). Understanding and Managing Risk Attitude. Gower Publishing, Ltd. ISBN 978-0-566-08798-1; and by Adhikari, Binay K; Agrawal, Anup (2016). “Does local religiosity matter for bank risk-taking?”. Journal of Corporate Finance38: 272–293. doi:10.1016/j.jcorpfin.2016.01.009. Wiki link is here.
  2. Credit card debt seems to show no signs of growing the United States. The charts from the Federal Reserve and The Center for Microeconomic Data make it easy to visualize.
  3. To clarify my definition of broke in this context, broke refers to my bank account hitting zero. Broke does not account for any investments I have. If you’re both fortunate enough and wise enough to put money in the market, you’re likely smart enough to know that drawing on it is usually a bad idea and should be a last resort. I am not your financial adviser, so be sure to do your research.

Bonus reading!
Wise man explaining how to supercharge your savings: Mr. Money Mustache



Well written, inspiring and relative. Thanks for sharing my friend, I commend your risk taking. Way to address your fear as well. I wish you the well in your travels. Much Love

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