“Follow your dreams,” they said. “Everything will work out as long as you believe in yourself,” they said. We are a culture obsessed with glossy success stories, but what happens when you follow your dreams and find…something else? What are the realities of a big leap? Who actually gets to take them? And when the ground beneath you is constantly shifting, how can you ever know you’ve made it? Below, three women in their own words on what really happens after the jump.
I was 27 when I decided to quit my job as a tax accountant to try to become a magazine writer. I joined a big accounting firm fresh out of university, and had been doing tax work for four years. I live in Singapore where most people lead a very structured life — graduate, work, get promoted, get married, have kids, etc. I knew that if I stayed in tax, it would be too difficult for me to leave when I was in a more senior position. So I quit.
At 27, it was humbling to be “the oldest intern ever” when my peers were 17 and 18. I was a fashion intern, which mainly involved sourcing items for shoots, carrying huge bags of clothes and accessories across town, and helping the fashion editor. Plus, like many internships, it was unpaid. It was tough — my previous work experience was completely different, I was learning everything from the bottom, and I was working for editors and writers who were the same age as me. But it was my dream to work at a magazine and write, so I told myself that it was a small price to pay. People who knew me said I was brave.
And I got lucky — I got a permanent editorial position in the magazine. It was entry-level but I was in the thick of my dream. I thought I had made it. I became a fashion writer — I had achieved my actual goal. I was earning less than half of what my pay was when I left the accounting firm and I still faced challenges. But I had the opportunity to interview fashion designers and celebrities and go on press trips, and, most importantly, women were reading my work.
But then everything came crashing down. It was a combination of factors. Work stopped being fun. I used to devour magazines, and then it became a chore. I would worry about things like whether our online stories were getting the necessary views. I began working with an editor who had a different style and suddenly, all my previous competence disappeared. I felt unsure and uncertain. I found myself going into work really early with the intention of completing work in a quiet office, only to stare blankly at my screen and start crying. The ideas I pitched were rejected and I felt sick to my stomach every day.
So I left. I was ashamed to do so because I had worked so hard for five years to chase this dream and I gave it all up. Perhaps I couldn’t take the heat when the going got tough. Still, I’m not sorry I left my first job to chase my dream. When I was young, I always wished I were brave enough to follow my heart. I’d still tell people to chase their dreams. It’s tough when you end up at the bottom of the ladder with all your friends and peers far ahead of you, but you have to try to forget this pride. Whatever stigma there is is all in your head.
Since I left the magazine, I’ve worked mainly in HR. I occasionally do the odd freelance writing job. I don’t think my career is conventional — perhaps I won’t be as successful as friends my age or as my mother would like me to be (sorry, Mama). I once told a potential employer that I am willing to do anything, as long as it’s interesting and meaningful. Although we can’t all be the lucky ones, I am happy I still managed to make my dream a reality for a moment in time.
I’d been living in New York for almost eight years when I decided to leave. I loved it, but I dreamed of being a writer, and I kept veering off course to flirt elsewhere. A good friend was in Los Angeles writing for television. So I did some networking during pilot season, and when an offer came in to be the assistant to the showrunner on a new drama, I took the demotion, the paycut, and the opportunity at the bottom of the ladder. This felt like the biggest leap I’d made yet: starting from scratch at nearly 30, leaving everything I’d built, including a strong sense of identity, behind.
TV writing was like that family friend I’d known my whole life who stumbled into new light and: BAM, it’s love. By day I was answering phones. The rest of the time, I wrote. If you build it, they will come — or, in my case, if you write samples, take initiative, give up nights and weekends when required, they might reward you with a staff writing job. It had happened for thousands who’d come before me, and I truly believed it would happen for me. My boss started telling me it would happen, too. He even laid out a rough timeline. I studied the craft, paid attention, soaked up critical intel, and perched eagerly on the edge of success.
Then, after seven years, I quit. What happened is complicated, but was punctuated by my boss skipping over me to promote my very close friend and creative partner, whom I’d describe as a white male (because he is one). I’d also describe him as behind me in line. I knew it; he knew it. My boss knew it — and acknowledged it when I called him out on the move.
I quit with no other job and what felt like no other choice. Again, this was a leap, but not the one I’d imagined. I spent an enormous amount of emotional energy on rallying. After all, I had written several pilots, co-written and co-directed a web series, amassed experience in production and development, forged solid professional relationships, and even had a one-act play produced. I had that tingle of cautious optimism: something better was out there for me.
But to this day, I’m either still falling from that leap or I’ve hit rock bottom, depending on how you look at it. No amount of writing or hustling as gotten me the gig. I have had little wins here and there, but they’re like sips of Gatorade on the way to the finish line. One of the hardest-earned lessons is that no one is entitled to success, and many people who find it don’t deserve it. I wonder if I disguised entitlement as ambition, even to myself. That exploration feels like further punishment (such a female thing to do!). Is it easier to blame myself for something rather than accept I simply tried and failed? At the same time, I regret not looking out for myself more carefully. I helped other people, including my white male friend, get closer to their own goals. I was taught to be generous with my time and support, and I followed that impulse, perhaps to my own detriment.
The positive side of pouring a decade’s worth of hard work into an unrealized goal is that you learn to live without external validation. I attached all of my self-worth to achieving this one goal. Somewhere along the way, I stopped looking for validation of my work and purely craved the work. Now, being excluded from the work doesn’t feel as much like pointed disapproval as it is personally disappointing. I want to work! It’s as simple as that.
Honestly, I curse the permission given to my generation to follow our dreams. I wish instead I’d been encouraged to make a good living, pick up a handy skill, or get fairly good at something no one else wants to do. I wish there hadn’t been such emphasis placed on the relationship between love and fulfillment. Much of my time now is spent processing and re-calibrating, as opposed to staying laser-focused on one goal. In doing that, I’ve realized that my career failure has been the great heartbreak of my life. I never dreamed of things like getting married or having kids–all I ever wanted was to be a working writer.
I don’t know what “success” looks like now because the dream is, for better or worse, dead. That’s not to say I don’t still want to be a writer. But, the fantasy of getting the job, what that looks like, feels like, has dissipated. If I were to get a job offer tomorrow, I’d be happy–but it would just feel like getting a job, not a dream coming true. Perhaps that’s a facet of getting older. Either way, it is sad to shed the romance from the gig. But I’m happy to have divorced my self-worth from it.
Just under a year ago, I quit my “dream job” as the director of a nonprofit center that functioned as an events venue, resource hub, and free public workplace. I had worked my ass off climbing the rungs of the nonprofit ladder to get there and a large part of me couldn’t believe I was “giving up” on something I had worked so hard to get. But I assumed the next rung of success was just waiting for me, and I was advised that I’d move up more quickly if I left my current organization. When I quit, I told all of my professional contacts and colleagues what I was doing. Some were supportive and some clearly thought I was making a huge mistake.
But as I started to look for similar nonprofit roles, I realized that nothing I was looking at excited me. As I tried to unpack this, I realized that even though I’d been telling myself that my physical health, mental health, relationships, etc. were my highest priorities, I had been neglecting them. I remember feeling like I wanted to do a “hard reset” — to reboot myself and give myself a chance to figure out what I really wanted. To restructure my life so it reflected my values and how I wanted to spend my time. I decided to give myself permission to explore and to say yes to more things that scared me. I was fortunate to have savings to support myself for at least six months to do this.
The year since I left my full-time job to freelance and explore has been wild — one of the hardest and best of my life. I’ve grown in directions I never could have predicted. There are some days I’m on top of the world and am 100% sure I made the right decision. I feel powerful and sure of myself and proud of myself for making this move. But there are also the days when I spiral, wondering if I made the right choice, if it was stupid to leave that job, whether people judge me, whether I’ll ever be that financially secure again, why I left the relative safety of a clearer path — an unlimited number of questions and doubts that feed off my insecurities and fears.
Before, “making it” was climbing up to the next rung and being rewarded with a more serious title, a raise, a nicer apartment, media coverage, etc. In this new path I’ve crafted, that’s less clear. It’s hard to file my taxes and realize that last year I made less than half of what I made the year before, when I’ve used income for so long as a metric for success. It’s hard to introduce myself and not have a clear title or organization to give myself what feels like legitimacy. It’s hard to not know how to clearly define my value to society. It’s hard to realize that I have an ego, and that’s part of what made leaving my “successful job” so hard. It’s hard to not feel like a failure some days.
But on the flip side, I trust myself more. I’ve grown stronger, more adventurous. I’ve met people who have shifted my worldview. I’ve consulted on projects that make me so excited they keep me up at night. I’ve spent more quality time with family and friends in the last year than I think I did in the previous three combined. I’ve reorganized my home to make a studio, I’ve gotten back in touch with my creative side and have even sold some of my art. Before, I felt like I was a jug of liquid pouring myself out into the world but never getting refilled, and I wasn’t sure when I would run out or hit my breaking point.
I still struggle with how to define “success.” It’s hard to untangle being productive with being valuable, and I think life is too complex to put into binaries. Some days I feel successful, some days I don’t, and most days I’m in-between. On the days I do feel good, I try to savor it and memorize that feeling for the days I don’t. I try to remember that even on those low days, my baseline for my life now is so much higher now than it was a year ago.
*Interviews have been edited and condensed for clarity.
Illustrations by Rebecca Clarke.