I Regret Not Working in Corporate During My 20s

It‘s hell to so many, but I would have thrived in it

Water cooler gossip. Small talk at the coffee machine. Meetings about meetings. The office hierarchy. The one obnoxiously loud co-worker. The separate cubicles. The pressure to arrive at the office earlier than you should because everyone else does. The offensively smelly lunches eaten at desks near you. The constant jostling for visibility. Workplace jargon like “drill down.” Work “socials” with workplace-proximity associates.

Those words may be describing your idea of literal hell on earth — the office workplace. It certainly gets a bad reputation, and off the back of the pandemic, many hope never to return again. It has always been divisive. For some, it’s a necessary evil that must be endured in return for a stable paycheck and some benefits. For others, it’s the only way to work and the ticket to the top, where you’ll be presented with your very own mahogany desk in a fancy corner office overlooking the city and those you crushed along the way.

My work life has been the opposite of the nine-to-five corporate career. I actively avoided it, aside from a couple job applications in moments of desperation. I ran my own business with one other person for four years before transitioning into writing and editorial roles. I’ve never had a “boss” — not by the textbook definition, anyway — and I’ve never worked in an office environment. The closest I’ve come is my new remote-working setup, where I share a workspace with my fiancé, effectively making us co-workers in our home “office.” My current “boss” is a fellow writer who gives me creative free rein and control of my schedule.

The freedom I have to work as and when I please is not one I take lightly. I’m aware that I enjoy what many view as the dream lifestyle. But the more I reflect on my working years so far, the more I feel this nagging sense that I missed out on something. I can’t help but wonder what I would have gained from a stint in the corporate environment, both personally and professionally.

More so, I think I would have thrived in it.

And I regret not giving it a shot.

It would have expanded my cultural awareness

In most of the part-time jobs I worked during my early twenties, my eyes were constantly opened to different cultures and values. When you work alongside people of different ages, genders, races, beliefs, and principles, you learn to be more open and aware. It forces you to expand your horizons and drop any misconceived stereotypes you may hold.

I worry that after many years of essentially working within a small bubble, I’ve left myself lacking in the cultural sense. I find that I’m often disconnected from the important issues of today. Some may think that’s a good thing; the mantra “keep your head down and do you” comes to mind, but I’m at an age where I want to be involved in these issues. I’m thinking less about myself and more about how to make a difference. The corporate environment would have accelerated the development of skills to do this—namely communication and empathy toward others.

Working for yourself means you can also chose your workmates, clients, and network. While it’s a nice luxury, I would love to be thrown into a cultural melting pot again to better understand the world I live in.

It would have provided me with a road map

I’ve spent the past 10 years constantly trying to “figure it out” with very little guidance. While I have connected with others in similar roles and picked up a mentor or two for good measure, it’s been a relatively unstructured journey, resulting in a lot of floundering and many missteps along the way. In summary, I’ve wasted a lot of time going round in circles.

The corporate world could have provided me with much-needed structure, in terms of not only work hours but also a future-mapped path ahead. In my earlier years, when I lacked confidence and clarity, this would have been a life-saver. No self-doubting or constant second-guessing about whether I’m walking down a dead-end; instead, very clear goals and objectives, with stages and steps marked out ahead.

Many herald the freedoms that come with working for yourself, but it can often lead to aimlessness. And in your early work-development years, that can be dangerous.

It would have taught me so much about so much

To borrow from my friend Michael Thompson, it’s important to “expose yourself to what both good and bad leadership looks like.”

Both are found in abundance in the corporate world.

Got a toxic boss? Sure, you can run, but learn from them first. Take note of what they do and how they act, and make sure to do the opposite.

Work under a brilliant boss? Take note of what they do and how they act, and make sure to incorporate their behaviors.

The same applies to your colleagues, your clients, and everyone else who surrounds you. You can learn something from everyone, and throwing yourself into an environment full of smart (and not so smart) people is a melting pot of knowledge, insight, and lessons that I wish I had dipped my hand into.

Most of my learning comes from personal experiences, both good and bad. While learning by doing is an effective way to learn, I lack external sources of insight and other people to contextualize what I’ve been doing. It also would have been nice to learn from someone else’s mistakes every once in a while.

Editor-in-Chief of Post-Grad Survival Guide • Columnist in Marker https://bit.ly/3hOsHzu • Thoughts on business, ideas, writing & more

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