Why Trying to Quit My Job (Sort of) Made It Better

It’s been almost exactly 18 months since I quit my job and watched the last corporate world elevator close behind me.

Reflecting on that time, it’s clear that my best career years—those defined by rewarding assignments, autonomy, increased paid time off, and better work/life balance—all came after I knew I was going to leave. Weird, huh?

How can we explain this paradox, and do we even need the drastic measures of financial independence to improve our work life?

Things Were Looking Good Before I Quit My Job

In 2017, we were feeling good about our financial situation. With our current savings and investing projections at the time, and barring any major calamitous market event, it was clear that we would hit our financial independence target in the next three to five years. We were tracking our net worth and fitting curves in Excel. Planning and dreaming. I fully intended to quit my job.

Damn, I still remember those heady days of financial path-blazing. I’ve said before that the anticipation of the thing is greater than the thing. And in many ways, it’s true.

But in those early days of 2017, we were hitting our “financial stride.” Our hearts raced with lower spending based on the Pareto Principle. I settled into visions of grandeur. I dreamt of the day I’d walk in and tell my boss I was retiring. I’d wait for his head to cock slowly to one side like a confused, big-eared beagle. As he narrowed his eyes and he brought his hand slowly to his chin, he’d say, perplexed…

“Retiring?”

And I’d say, transitioning from whisper to proclamation with a sinister smile…

“Yeah boss, we’re RETIRING. Like, FOR-EVER.”

Pep in My Step

I’m kidding, of course.

You know how I feel about retiring early. I was actually really nervous about the “I quit” conversation I never had to have. Regardless, as I watched our net worth grow and grow like courage on a three-beer buzz, I too felt myself walk around with what can only be described as…

…dare I say it…

…not possibly…

Well, yes…swagger.

At this point I no longer needed the job. My whole life I needed the job.

Chick-fil-A in high school?

That new Toy Machine skateboard deck isn’t going to pay for itself!

The myriad other restaurant jobs before, during, and after college?

Hey man, the night is young, my man!

And then finally, at the anticlimactic end of childhood and my first corporate job in Houston—well…

We’re getting married this year and I’d like to have a nice dinner at the restaurant on Friday and hopefully travel abroad, one day.

The Dream

In a strange twist of fate, I dreamt a strange series of events the night after beginning this post.

In this dream I find myself in some sort of school/work hybrid environment. I am younger, surrounded by many other college-age folks. Leading this group is a strong-minded, middle-aged woman; the disciplinarian.

In this vivid dream, I’m attending a bizarre (well, bizarre in hindsight; it made perfect sense as I slept) gathering, where two students are explaining their upcoming vacation in PowerPoint form. The couple is presenting slides with maniacal detail for events yet to occur. Apparently, the disciplinarian has insisted that all vacations be planned and fully approved, down to specific restaurant choices and even future menu items. I don’t know what I’m having for lunch today, much less two weeks from now!

When I ask for clarification on what I’m hearing, she confirms. Turning her head toward me with utter disdain, shoulders back and her chin held high, she speaks:

“Yes, we expect all travel to be pre-planned and approved. Upon completion of your trip, we require receipts to ensure that you traveled in a pre-approved manner. You are a representative of this institution, after all…”

…she says, putting extra stank and enunciation on in-sti-TU-tion.

Instantly driven to anger and a rising heart rate, I shoot back, my face growing redder…

“Look, this sort of planning takes the spontaneity and beauty out of travel. When I travel, I want to feel inspired to randomly pop in a restaurant, coffee shop, or place of my choosing.”

Eyes in the group grow wider, and I swear a couple of heads are nodding in subtle approval. But the disciplinarian does not budge. Speaking slowly, with an eerie calm, she says…

“Mr. CC, it seems you are failing to understand the rules of this institution.”

So It Goes

And as Kurt Vonnegut would say, so it goes.

Another day in the life of being a square peg guy in a round hole world.

When I realized I was on a glidepath to financial independence, I settled into a workplace demeanor more suitable to my personality. I stopped fighting the urge to give honest feedback in meetings. In fact, meetings deemed unnecessary were declined with increasing frequency. I even, at great perceived risk, pushed back when asked to take on an assignment that sounded, frankly, terrible.

After several months of this new Office Space behavior, I was asked to schedule a performance review. Had my new “do not care” mentality shone too brightly for the corporate world?

I’ll be honest—I was nervous.

Why We All Need Pessimists

How many times have we sat in a meeting or surrounded by others, biting our tongues and nodding in agreement as someone said something disagreeable?

In my experience, this behavior is widespread in Corporate America. And I was one among many. Those who continually spin all bad news and polish any performance blemishes are often those that rise swiftly through the ranks of management. At least that’s the stereotype, right?

But there are real manifestations to agreeableness in the workplace.

For a decade I witnessed overpromising on performance, underestimates on costs, and a failure to systematically analyze why so many projects turned up either uneconomic or with undesired consequences. This trend of overpromising and under-delivering spread like cancer through the industry. Investors began to flee to other industries, fed up with pumping money into the industry without the promised returns.

Yet, the water cooler conversations were often the same:

“Did you hear that crap we are telling management? These wells are going to be turds!”

“Can you believe that quarterly presentation?! WOW!”

“Who made THAT slide?”

The oil and gas industry, like many fields, is filled with very smart people. Once armed with a clean and scrubbed database, most scientists and engineers will make similar maps, graphs, or tables. In many cases, the conclusions reached from a common dataset aren’t vastly different from person to person, or company to company.

Are we unconsciously biased towards delivering results in a positive light?

Healthy Pessimism Before I Quit My Job

The problem, I’ll offer, is that there isn’t enough healthy pessimism promoted in the workplace. And I’ll admit, I’m a bit of sceptic and pessimist at heart, so I’m biased to believe that this character trait has merit. And hey, research alert, there are surprising benefits of being a pessimist, so long as we harness pessimism and avoid simply blaming.

I’ve often viewed situations or events with a cautionary sense of “how bad can this be?” When I moved to Houston, the pessimist in me expected the worst of places – heat, humidity, strip malls, flat lands, and Texans (kidding Texans, we love you!).

And I was right!

However, because I had set a ridiculously low mental bar, I was pleasantly surprised when I found elements of the city that did not indeed suck. For instance, the food was amazing, the people were a diverse and multicultural bunch, I connected with extended family, and I discovered—against all odds—rock climbing, my passion of the last decade.

My natural tendency is to bring a reasonable level of skepticism and pessimism to all that I do. When sitting in a crowded corporate meeting room, the incandescent lights dimmed and eyes glinting under the glare of a PowerPoint presentation, my jowls sink and my eyes narrow. I was once told by a professor that, when listening intently, I have a look that can melt granite.

I mean, come on! Melt granite?

Leaning In

Once the value of each paycheck started meaning less, I slowly and unintentionally started leaning in on my inherent, but not-that-bad, pessimism. I want to tell you that I shot to my feet in made-for-TV style at the mention of anything disagreeable, but that would be a lie.

We as humans want to feel part of the herd. The guy who disagrees with everyone will soon find himself without a herd. Or, at the very least, without a job. And I certainly don’t disagree with everyone or everything, anyway.

In fact, I was usually too busy daydreaming about my next vacation or visualizing the movement on my latest climbing project to care that much anyway. The real, less sexy truth is that I simply inserted a bit more input than I had in the past. Some of this input went against the grain of the company talking points at the time. And it felt risky.

The Feedback

The feedback I started to receive was unexpectedly encouraging. I was told, much to my surprise, that I was a leader in the group. I really didn’t know what to think of this. My brain, sluggish with the weight of workplace senioritis as my “I quit” day lurked on the horizon, couldn’t comprehend what I was hearing.

Here I was, essentially sitting in front of “the Bobs,” being told that my workplace pessimism was a sign of leadership. WTF, I thought.

The team and company wanted brutally honest interpretations of the data. Management needed to hear if we were going to spend millions of dollars on a turd.

And that’s why, good folks, the world works in mysterious ways.

So Why Did I Quit My Job?

If I was being called a leader and provided rewarding assignments, why didn’t I just stay in this wonderful new world? Why didn’t I keep my name on the payroll, continuing to work on building career capital and all the benefits it provides?

Well, soon after all these developments, my company was unexpectedly acquired by a competitor, a colorful story described here: I (Sort of) Quit My Job.

I was offered a chance to put my name in the hat for a position with the new Big Fish (my current company being the Small Fish), and move back to Texas. After considering this option for about a fraction of a nanosecond, I politely signed the forms and accepted my severance terms.

That was, to this point, the end of my corporate career.

So, What’s the Lesson Here?

Is there a lesson?

The “blogger-approved” lesson is that if you get yourself in a strong financial position, you can more comfortably be you. And perhaps you being you is exactly what employers want…unless you are kind of mean or generally unpleasant. That sounds like a nice bloggy way to end things.

In the end, I quit my job. But was this drastic move even necessary?

But maybe that’s just my personal weakness. Perhaps many of you find no problem being you at work, even if you need the job.

Do you need financial independence to impress the Bob’s, or do you already have all the power you need?

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