Quitting a job in a ‘never-give-up’ culture

“Oh hey, you’re officially jobless now, right? Congratulations!” said a friend on Saturday, two days after my last day at my first company, after four years.

I’ve been offered a lot of congratulations since I quit my job, both from those who knew I was unhappy and those oblivious. “Thanks,” I say, unsure of how else to respond. Unsure if the congrats are sincere – does the other person truly appreciate what it took to quit a well-paying job to pursue my happiness, without something firm lined up in the interim? Are they secretly envious? Or is it a reflex – person makes job change → offer congrats.

Or do they know something I don’t? From my perspective, this could be a big mistake.

Personally, I’m not so sure I deserve congratulations.

Was it gutsy? Or was it a cop-out? On one hand, quitting feels like a defeat. “I’m not a quitter,” 15-year-old me told my mom with arms over my chest and my lips trembling, biting back tears as I faced the oh-so-dramatic trials of AP Physics. “Don’t quit,” quips the Nike bro-tank that whizzes past me adorning an ultra-marathoner on the bike path. “Never give up,” chimed the women at the inspiring and empowering Women of Influence luncheon in Milwaukee last month. But in the same breath, “Follow your dreams!” they shout.

What if following one dream means giving up on another? The message of “stay the course” bombards me from every angle. But what about a strategic pivot? Is there a difference between retreating to regroup versus running away from challenges? 

Some of my friends ask a follow-up question: “Are you scared?”

YES. In fact, I’m terrified. I’m straying from the path. I’m leaving a job that grants me instant credibility with the backing of a community institution – when you say you’re a reporter with the Milwaukee Business Journal, people adjust to give your ego some elbow room with a respectful nod. Say you’re a freelancer, and that nod shifts imperceptibly to the side as the respect turns to doubt.

This is probably what it feels like to make a living as an artist. Mad props, artists, and my infinite apologies for all of the times my appreciative nod was tinged with doubt.

One major surprise is the reaction from my senior mentors. Without exception, they express support. This from the generation who valued toughing it out, staying loyal, slogging through to the end goal of a comfortable retirement. They’re the ones who criticize millennials for chasing pipe dreams of finding instant fulfillment in our first jobs. And yet, when I tell them I’m thinking about a career change, and quitting my job to freelance and devote my attention to discovering my true passion, they say, “Go for it.”

But the doubts still chant in the back of my mind:

Don’t quit. You won’t make it on your own. Make the smart move. You’re just not trying hard enough.

As a kid, I never dreamed about being a journalist. I dreamed about being a novelist. I started a half dozen novels, and spent weeks daydreaming complex relationships and plot twists. Somewhere along the line in high school, reality hit – 5-year-olds could have written these plots – and I set that dream aside. I decided to try my hand at journalism because, in the words of my 17-year-old self: “In journalism someone tells you what to write.” Little did I know. Later on I would tell people that I stuck with journalism because of the people I got to meet, and the fact that I could ask them things like “What is your deepest insecurity?” within five minutes of meeting them.

In this past year, while continuing to work as a journalist, I’ve actually begun to identify as a writer for the first time – mostly because of the success I’ve had writing on LinkedIn. And simultaneously, it’s also the first time since college that I’ve seriously considered making a living doing something other than writing, as I realized that I don’t have to make a living writing to continue to write. 

But now it’s real. Olivia Barrow, writer for hire.

It’s a big step out into the unknown, away from the security of a salary. It may be a foolish move. It’s probably foolish. I may run screaming from self-employment in a few months back into the welcoming arms of an employer.

The good news is, the only person I have to answer to now is me. The bad news is, the only person I have to answer to now is me, and I’m my toughest critic.

Here goes.


7 Comments Add yours

  1. strokewriter says:

    Like you, I’m lucky enough to be able to fall back not only on some old training in writing, but in all the learning experiences that make my writing now even better than those earlier efforts. Stay the course, and give it your all.

    I can certainly relate to what you have written – but in my own case, it wasn’t really a choice but something that was thrust upon me by circumstance. Whether choice or circumstance, remember that there are people pulling for you that you don’t even know about. Good fortune!


  2. Omar Al Tellawi says:

    Hello Olivia,

    Although I might be defying all dictionaries out there by saying this, I think the difference between Quitting and resigning can be viewed by yourself first and your colleagues, the difference is (in my opinion) is walking tall out of the building in case of a resignation or with your tail between your legs in case of quitting… I don’t think this is a case of giving up, I see it as investing in yourself more and therefor holding on to where you think yourself deserves to be. What you did takes a lot of courage and self-respect, and I have been touched by your article because I’ve known so many employees who stuck with the safe employment option and never had the courage to do what you have done. I wish you all the best and keep walking tall…

    Omar Al Tellawi


  3. Taylor Gregg says:

    As someone probably older than your ‘senior mentors’ I too applaud your gutsy move. I took the outside path, road less traveled, after a year of trying to write short stories, and ended as a National Geographic Magazine editor, and later, editor of a peer-reviewed bio science journal, and with a basket full of publishing and journalism excellence awards along the way. I was also a trouble maker determined to work for myself in meeting my personal standards when they clashed with the corporate interest, and often had to quit a good job in order to preserve my personal values. All this said, our journeys are personal, the world is different now, and it may not be easy to land on your feet. Maybe mine was a charmed life; the path is obviously convoluted. On the other hand, if you believe in your values and abilities, you will certainly live to regret the road not taken.


  4. V.L. Perillo says:

    Hi Olivia,

    I feel so identified with your story. I also quit writing when I was a teenager, thinking I wasn’t going to be able to write stories and make a living. Years later, now 29 years old, I’m working on a novel, completely determined to make it as a writer.

    I admire your courage in quitting your job to pursue a freelance career, because I still haven’t found the guts to do it. I’m too afraid I might not make it, so I keep to my studies; yet, at the same time, I find it very hard to make progress in my writing as my job keeps me exhausted most of the time. As an alternative to resigning to my path in science, I’m looking for a part time job– something that will pay me enough so I get a set amount of money each month, but leaves me with enough energies to continue writing.

    Whatever path you choose, I don’t think you are giving up. Priorities change as we grow up, and things we thought were good for us turn our not to be so. Recognizing that you need to change paths and taking the steps to do so is a strength. It isn’t quitting. It is continuing on the path you think is right for you.

    Changing paths is actually what so many people wish they could do, but are too afraid to try.

    Thank you for sharing your story and I wish you success!


  5. qnoi says:

    Hi olivia, i read this post as it appeared in my linkedin newsfeed and somehow got an instant urge to connect with you. As you’ve seen from these online comments and real ones from people you actually know, such unsettled feeling is one shared by many. I am still finding courage to make that decision and your post strengthen me a bit. Thanks for sharing and be my ‘peer support’. Stay connected!


  6. Curtis says:

    Hi Olivia

    As someone, who twice in a thirty year career, has walked away from employment doing work that I thoroughly enjoyed I understand the turmoil you are experiencing. Everyone’s reasons for doing something this bold and potentially unforgiving are unique to them, but regardless of the reason the risk is the same and consequences can be equally severe. I can say that i never regretted those moves and in both situations being bold and taking the risk of unemployment to pursue a vision of a better path paid off in explosive career growth in a much shorter amount of time than I expected.

    While I don’t recommend this approach for everyone, it can succeed if you are confident, unafraid of change and believe that there is something better and you are willing to work at to achieve it.

    Carry On.


  7. S. Ramaswami says:

    Let me share something that an older alumnus of my university said: “Find something that interests you, and become good at it. If you find several things, become good at them. Some of them will become your passions, some of them will not.” His point was that it takes time to find our passions. Good luck!


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