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How To Know When It's Time To Leave Your Job & Make The Switch

I am extremely lucky to have so much family support with this business from the start. My brother actively promotes our mission and services, in addition to attending every event where my parents always show up too. From the beginning, they have been my biggest champions, which is why I am also extremely grateful to have the support of my cousin, Anna, a wonderful writer who is our blog contributor for today. Her honesty about knowing when it's time to leave when you need to find your career purpose elsewhere is inspiring and I hope you feel the same when you read it.


Over the last five years, I built a career from the ground up at various cultural institutions in the Chicagoland area. I wrote communication pieces, I managed press and donor relations, I learned about philanthropy and how a nonprofit runs, and I met some incredible mentors and friends along the way. Then, in the middle of a pandemic, I left all of that behind and headed back to school.

The few weeks between my last job and the start of graduate school were full of anxiety. Why, again, did I leave my well-paying job with great co-workers and excellent benefits?

Suddenly, my personal and professional future was completely up in the air once again. I felt like the nervous 22-year-old who had just graduated from college and didn’t know what to do with my life. Except for this time, I was 27 and cynical enough to know that sometimes crazy dreams and best intentions just don’t work out and you fall flat on your face.

Soon enough, though, my graduate classes started and the fear began to dissipate. I entered the Columbia University Human Rights Studies M.A. program and instantly felt like I was in the right place for this new season of my life. Since I finished undergrad in 2015, I forgot how much I loved reading, writing, and learning on a daily basis. I embraced my newfound ability to think for myself and make my own work schedule. Plus, I learned I had no need to stress about my next career move. Every day, professors and advisors would share ideas for potential career tracks in human rights and offer the tools and networking opportunities to land rewarding jobs.

I finished up my first semester and just had to laugh at myself. Due to fear and doubt, I was almost going to stay at my old job and miss out on this incredible opportunity to better myself and my life. We are humans. We grow out of relationships, friendships, hobbies, and lifestyles. Why would we ever assume that we would follow one career track, or stay at one workplace, for our whole lives?

I think the most important notion to consider when pivoting your career is balance.

It’s rare that flipping your desk and leaving your job the day of will give you long-term career success. On the other hand, chaining yourself to that desk because you’re scared nothing better will ever come along will likely leave you feeling deeply unfulfilled. So, balance pursuing your dreams with the need to keep a roof over your head. Balance exploring the world with contributing to your 401k. Balance meeting your boss’s every demand with your own sanity.

While I worked full time, I used my PTO days to travel to Israel, Aruba, and all around the U.S. on trips with family and friends. I used up every single hour of time off, knowing that even if I worked 80 hours a week there would inevitably be that lingering project and urgent deadline. Especially if you have overachiever and people-pleaser problems like me, your boss will always find a way to fill your plate. Just remember that when you leave that job, a new person will happily fill that position. Your company will find a way to move on without you, I promise.

Some words that I return to when I’m having trouble finding balance in my life are from one of my favorite poems, “Advice to my Son” by Peter Meinke:

“The trick is, to live your days

as if each one may be your last

(for they go fast, and young men lose their lives

in strange and unimaginable ways)

but at the same time, plan long-range

(for they go slow; if you survive

the shattered windshield and the bursting shell

you will arrive

at our approximation here below

of heaven or hell).”

You have your whole entire life in front of you, and yet, only so many days left. If you are struggling to find purpose in your current career or wonder if there’s more for you out there, go fill out that job or grad school application – now!

Connect with the author here: Anna Miller

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