Working For “The Man” Has Its Perks


This week marks my two-year anniversary from quitting my corporate job. I started reflecting on this anniversary and began to question did I make the right decision? And what have I learned in the past two years?


Photo Credit: Tim Patterson

Well, I’ve discovered life would be so much easier if I opted to go back to a 9-5 job working for “the man” and gave up life as an entrepreneur. Honestly don’t knock working for “the man” as he is very generous!

He offers health benefits at little or no costs. He will still pay you while you’re hanging on the beach during your family vacation. And if he is really generous, he will help you plan for your retirement.

I won’t lie, I miss the man some days. When I was in it, I thought he was abusive as hell. The man always wanted me to show up and work certain hours and projects, when I really wanted to hang out on the beach writing. He also came with his crew of passive aggressive co-workers who at times made me question if the Twinkie Defense would work on my behalf.  I complained often to friends about my duties, co-workers, his crazy expectations and how bad I wanted out.

So now that I’ve been out for two years, I feel slightly guilty for fondly thinking of the man, especially when I hear about friends getting bonuses from their man.

My reality check is that freedom from the man doesn’t always feel freeing. Working for yourself requires you to be free to work pretty much every day. Long gone are the weekends free to do what you want to do. And my heart still aches for those annual trips to Amsterdam and Vegas on someone else’s dime.

Yet, if I’m being completely honest, I complained about the man because we weren’t a good fit.  I’m like Baby from Dirty Dancing when it comes to this type of relationship. I am not meant to be in the corner working in a cubicle. I need to be free to create. I need to work on my life purpose and not someone else’s bottom line.


Freedom from the man is not always as glamorous as I thought it would be, but I was meant to be free to follow my own dreams and passion. This bird can’t be caged!


Are you an entrepreneur? Share your stories (good and bad) reflecting on life after the corporate job!



An eclectic, world traveling sista from San Francisco expressing 'Rogue-Thoughts' on food, travel, music, fashion and living an authentic life unapologetically.

Be first to comment