Where is “Should” Holding You Back?

Carrying on with the “shoulds” brought me misery and I mistook it for reality. I could’ve led myself to the things I love if I had just listened.

M
4 min readSep 12, 2022
Photo by Andrew Neel on Unsplash

I’ve known that I wanted to quit the corporate world since the moment I stopping partaking in work travel.

To me, this was the jackpot; I’d discovered a way to get paid to travel. I worked in New York, DC, the Florida Keys, and Sydney Australia, for goodness sake. While I reliably answered all my emails and reported back on my accomplishments, I was thriving because the weight of my responsibilities could not outweigh the thrill of these adventures.

The only problem with taking a job exclusively for the aspect of travel is that you might not actually like the job itself.

When you realize you don’t like your job

Predictably so, travel budgets were sliced and work became WORK approximately 1 year into my corporate experience. I thought “wow, I used to be so lucky but someone like me can’t actually get paid to travel”. And despite discomfort, anxiety, and repulsion to office life, I accepted my destiny to live and breathe the 9–5.

I replaced my has-been travel gig with a “real” job replete with quotas, dual monitors and unbounded busy work. I’d made it, right? I was grinding and isn’t that what you have to do? Grinding my way right through emotions, stress, the workplace toxicity, and all those little whispers of rebellion from my belly saying “this is not a fit, you need to find a different way to spend your week days”.

I was on right on track to climb the next rung of the ladder but I could not comprehend why I wasn’t fulfilled!

Do you know why you’re unhappy?

Well, I hate to break it to past-me, but I was not listening to any of the truth that was banging around inside of me, begging to be heard. I’d completely missed the memo that there was once an element of work that I loved and instead of trying to replicate that experience, I decided it was beyond my reach. I botched the opportunity to LISTEN and pursue a different narrative.

All that time, those innocent little messages bubbled up to request my return to something that felt better. Instead, I addressed them with a friendly, “shut up and stick with with script”. I was married to the story of slogging through the traditional workforce to earn a lot of money and eventually one day, you finally deserve to retire into weekday freedom.

I didn’t consider that there might be a way to listen to what I love, find work that’s intertwined with my interests and simultaneously earn a living. No, I should accept reality, put my head down, and ignore the rest.

Keep what fits and release what doesn’t

I fought this battle through the epitome of a poisonous work environment, blaming my internal dialogue on the twisted leadership and lack of morality amidst my second job. I left for a healthier setting yet, thorough reflection today in my third job is revealing a familiar pattern.

That aforementioned message I so proudly fended off for many years has not left me or changed in the slightest. Instead, it’s been patient, steady, persistent waiting for me to quit the gaslighting. It’s surfaced once again to remind me that here, now, in a healthy, lucrative, interesting environment, I’m still not where I need to be.

I dread Zoom meetings, strategic plays, conversations about customer needs and all the things I vowed to deeply care for in my role! Done is the whispering; we’ve graduated to the inside voice. It’s audible and clear. I do not fit into the corporate track.

Accepting what ‘should be’ denies you the opportunity for what ‘could be. Yes, there are unavoidable necessities and I’m not preaching recklessness; you have to have money, relationships and some plan for your life. But those are manageable details to incorporate into a more honest vision of your future as long as you can ruthlessly sacrifice anything else that does not align. I’m taking about the designer purses, the fancy house; do you really care to have them in your life? Or do you chase them because you should embody traditional molds of success.

Taking steps towards an aligned path

Ignoring my inner voice that just wanted to guide me towards something more aligned has not gotten me very far. Instead, I’m years into a career I feel no attachment to. I’ve spent so much time pushing through it anyway, assuming meaning would be made, and here I am, too far down the road in the opposite direction.

To make a change, I’ll need to start listening more intently. Even mulling over the way in which this story has evolved, it’s so obvious now that I’ve already experienced alignment to some degree, early on in my career, when I was so enamored with the adventure of work travel that I didn’t realize I had a job. Returning back to moments that clicked so nicely is a great tool and so I’m committed to be more in touch with my truth.

It won’t be an immediate transition — I’m not the type to jump without some direction but I do intend to prevent a repeat of my infamous pattern. I’ll need some time but not too much. My deadline is January 26th to make moves; enough time to really sit and contemplate but not so long that I do not take action. If I experience any contradiction of what I currently feel so acutely, I’ll proceed with caution. Otherwise, here’s a toast to my future resignation.

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M

I write about career development, personal finance, and adventure. You can find me daydreaming about what to take on next.