Photo courtesy of Jamie Kenney

10 Ways I Switched Careers, Despite Significant Challenges

After my second child was born, I left a job I didn't hate to become a professional writer. Considering you are reading this article — one I penned as a staff writer — you can probably guess that this story has a decent ending. How I changed careers is a story of give, take, chance, hope, and tremendous privilege.

I was a creative writing major in college, and one of the things the head of the department was crystal clear on was the fact that writing was not a particularly lucrative endeavor. "It's highly unlikely that any of you are going to write the great American novel right after you graduate," she informed us at least once a semester for four years. "Statistically it will take you a long time to get anything at all published. And even if your genius is recognized immediately and you're published in the next few years, you're still probably not going to be able to make a livable income on creative writing alone. Even the most famous writers usually have some sort of teaching job on top of their craft... and it's even worse for the poets. But," she would say just as we were all about to sink into a pit of despair (not hard for writers to manage, by the way), "Your skill isn't just in fiction or poetry: you can communicate effectively in writing, and — never forget this — that's a skill most people don't have. You can make that work for you professionally, particularly as you hone your craft."

I took this to heart, and every job I've held since college has included a significant writing component. I wasn't doing anything especially creative —lots of reports, press releases, and promotional materials — but I didn't dread going into work every day. Yet as time wore on, I began to wonder what I was trying to accomplish professionally. What was the aim? Where was this going?

This was also around the same time that I began dipping my toe in the world of writing online. A toe became a foot, a foot a leg, and before I knew it I was wading in a sea of uncompensated work... and at first I didn't even mind. But over time, I thought to myself: "Other people, people whose writing is no better or worse than mine in some cases, are paid to do this. Why not me?"

My life was changing: I'd just turned 30, I had two children, and it I realized that if I wanted my professional life to move in a different direction it was going to take sacrifice and faith. Here's how I was able to take the leap:

A Massive Safety Net & A Lot Of Privilege

It would be willfully ignorant and irresponsible to try to sell this to you as a gritty, plucky "nevertheless she persisted" sort of story. Sure, I took a risk, made a change, and it wasn't easy, but it was easier than it would have been in most other people's shoes. I am the beneficiary of gobs of privilege and support.

Around the time my son was born, my husband, baby, and I moved out of one of the most expensive cities in the world to live in the attached, two-bedroom apartment in my grandparents' house. The goal was to live there so that we could save money to buy a house of our own. Changing careers, at this point, wasn't on my mind in the slightest, but it proved to be a crucial aspect of how I made the switch.

A Supportive Partner

Very often, people view having a partner who also has a job as a given, but that's hardly accurate. Having a second income (plus the sweet living arrangements) ensured that even if my career prospects didn't turn out the way I'd hoped, we wouldn't starve or be unable to afford a doctor or necessary medical care (my husband's job offered benefits).

Taking Turns Advancing Careers

Before I decided to change careers, my husband actually did the same. I stayed at my office job while he stayed home with our son and earned various certifications to begin working in a tech field. So what he would eventually enable for me, I first made possible for him.

However, for him to drop out of the workforce to make this change was an easier choice: I was the primary breadwinner, had the better insurance, and the field he was looking to enter paid invariably more than he was making at his old job. When he started his new career, I was still making more than he was.

Deep Discussions About The Future

We did a little bit of forecasting. What could my partner reasonably expect from his career path? What could I expect from mine? What kind of work/life balance were we aiming for? What kind of savings? Would we be OK with the possibility that this move could potentially push back our goal of home ownership? For how long? If I didn't succeed as a writer, could I feasibly re-enter the workforce in a capacity more in keeping with the jobs I'd worked?

Big important discussions about the future are really scary. I'm a pretty laid-back person and proactivity at this level can stun me into a catatonic state. But, at a certain point, it becomes necessary to discuss the stuff that makes you uncomfortable so that you can realize (or even just confirm) your goals.

Sacrificing In Some Areas

Unless someone invites us to join them on vacation, we do not take vacation. "Unplanned spending" (say, if we are randomly invited to dinner) is really not a thing at this point. Savings are not what we would like them to be. We had to move our oldest from the crunchy, hippie, Montessori school we loved to a preschool with more affordable tuition. I haven't bought new shoes in a couple years because while I could certainly use them, I don't need them.

Certainly I don't think I'm unique or noble for living on a carefully calculated budget. Indeed, I live in downright luxury compared to many. That said, the fact remains that doing something I love doing came at a cost.

Utilizing Every Network

True story: I got my main writing gig through an acquaintance of an online-only friend on Facebook.

I know, right?

But a friend I met on a mom message board was in a professional group with my first editor who was looking for regular contributors.

Point is, when you're a writer, you never really know where your next job is going to come from, so keeping your eyes and ears open at all times is absolutely clutch.

Maintaining A Carefully Balanced Schedule

Part of my ability to change careers meant paying for daycare was absolutely not an option. I had to work from home... with kids. If you have ever tried to accomplish literally anything with children in the house, you can guess how monumental a task this can be.

This meant carefully planning my day to be able to fit in writing time, pitch time, and caring for two very young children. Eventually I was able to earn enough to send my youngest to daycare for a couple hours three times a day, which was a huge help, but still didn't negate the need for a strict schedule.

Having Some Background In What I Was Aiming To Do

What I was doing and what I wanted to do were not unrelated: the primary function of my former job had been writing, just not the kind I wanted to be doing. I'd also had a few unpaid writing credits to my name to be able to share in order to get my foot in the door with editors. (They like to know you can string a sentence together before they even consider you.) So it was a big transition, but it's not like I was leaving a lucrative job to pursue something I had no experience in, like circus arts or pyrotechnics.


There's usually not a great time to make such a big professional (and financially significant) decision. This held me back for a long time, and I don't blame my past self. There's a lot to be said for security, especially when you have a family. Still, my career path as it existed was hazy and unexciting. What I wanted something that would be more fulfilling and provide a better work/life balance as a parent. Then there was the practical side: the cost of childcare for two kids devoured most of either of mine or my husband's paychecks, and my commuting costs took a sizable chunk from out net gross as well (to say nothing of the mental toll of a 3-hour-a- day schlep in and out of New York from the suburbs.

I agonized over all of this with a friend, who later sent me this quote from author John :

Leap and the net will appear.

And I thought, "Yeah. That's how life works, isn't it? You have to take chances."

And Again, So Much Privilege

I cannot stress this enough: leaping and waiting for net is much, much easier when you already see a backup safety net below you, even if it's farther below than where you're looking for another to appear. I always had my tribe: supportive family and friends upon whom I knew I could rely. Even if I failed tremendously and lost everything we'd saved for a home or didn't make any money at all as a writer, I knew I would have a roof and groceries. I do not like the whole #blessed thing, but... I'm #blessed, for real, and it would be an insult to everyone who works as hard and harder than I do to pretend I'm not.

And I don't say this to downplay the things I did to forge a new path for myself and my family. I'm proud of what I've accomplished. I'm doing something I love and I'm able to do that in large part through careful planning, prioritizing, and effort. But for all I have done to make this work, there is an enormous an invisible system that held me up and carried me along at times that I wouldn't have been able to manage on my own.

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