The illusion of job security

Embracing uncertainty outside of the corporate world

Yellowstone National Park, Wyoming

My father, Joseph, immigrated to Los Angeles from El Salvador in 1949, when he was four. When he was seven, he was placed in a home for boys in San Dimas, California—my hometown. At 18, he joined the Navy during the Vietnam War and spent time with the doctor onboard his ship, who turned him on to medicine. With the help of the GI bill (plus many years of working multiple jobs while taking a full course load), he attended Cal Poly Pomona, then dental school at UCLA, then oral surgery residency at Georgetown.

He lived the American dream. Then he made sure life was infinitely easier for his three children than it had been for him. He gave us financial stability in abundance, and his financial support of my college education meant I had an immense, debt-free advantage when I entered the workforce that most people do not. I owe so much to my dad.

However, my dad also instilled in me a specific worldview of work and money that is directly tied to his experience as an immigrant who struggled to come up in the world. Work was always at the top of his priority list, meaning he often missed my softball games and swim meets. (But he did make the ones he could; on one Saturday my dad accompanied me to a high school club volleyball tournament where I never made it off the bench—at the end of the day, he was so upset for me that he cried.) For him, the direct route to security and prosperity was a safe, lucrative career path, and he gave us kids three options: doctor, dentist, or lawyer.

My older brother did go on to be a lawyer! My dad is so pleased. But my sister and I were never destined for all that. I was reading and writing with abandon from a very young age, and my sister, who is an incredible makeup artist, always struggled in school. My dad was far from a tiger dad: we were given cart blanche to dive into all the theater, dance, sports, etc. that we wished. But he never saw much value in the arts, and I knew it. And I wanted nothing more than to make my dad proud.

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I started unloading my dad’s belief system and building my own throughout high school, where I went full theater kid, and college, where I joined the school paper and claimed a communication studies major. Grad school was a compromise between our two worlds: I knew I wanted to be a journalist and I loved school, so J-School at Syracuse was an easy choice for me, and my dad wanted me to get all the education I possibly could, so he urged me to go. (He still badgers me to admit that grad school was key to my success as a journalist; I still tell him that a college education isn’t necessary to be in the industry.)

When I moved to New York City and began working in media, I stayed firmly on the track my dad said would keep me safe. I was a magazine writer! But I was also in corporate, full-time jobs where I was underpaid, and miserable rounds of layoffs were all too common. I didn’t work grueling hours, for the most part, but I was ambitious and focused on climbing the corporate ladder and getting all of the traditional kudos of the professional world. At 28, I was promoted to lead Editor of Time Out New York, and then a couple of years later I took a role as Deputy Editorial Director at Culture Trip. I was finally making enough to pad my savings, and I had a leadership role that took me to London four times a year. My dad was thrilled.

But as I took on more management responsibilities, the time I put toward artistic work faded into the background. By 2020 I felt creatively dead. I was barely writing, either at work or outside of it. Instead, my days were filled with meetings, strategizing, managing, and editing. The artist inside of me shriveled—a small but persistent voice kept saying, “Create or die.” Yet I continued to stuff it down in exchange for the “safety,” respect, and glitter attached to my senior role.

I had made it. This was what I wanted, right? As far as my parents and the American value system were concerned, I was successful. But I wasn’t fulfilled. My inner child sat curled in a ball, head down, filled with anxiety and dread. I could see myself five years in the future, with a higher salary and an even better position, filled with regrets.

When had I stopped being a writer? I looked at my professional life so far and wondered: Is this it?

Soon, the universe stepped in to do its thing. Two weeks into the pandemic, I got laid off. In a flash, 150 editorial team members in multiple countries were severed from their livelihood and health insurance, just moments into a terrifying global health crisis. My job didn’t keep me safe.

I didn’t know it then, but that was day one of a long journey to unlearn all that I thought I knew about work, job security, financial safety, and success.

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Three years later, I was on a video call with my financial coach Stella Gold. I had recently learned that I didn’t get a full-time job that would have been a huge step up financially and a major reentry into the corporate media world.

I shared with Stella my disappointment: While building my career as a freelancer I’ve continued to apply to full-time jobs that felt right for me. I’ve had a couple dozen interviews and made it to the final round a few times, but I never landed the job. I was worried I’d lost my competitive edge; that if I stayed out of media too long I would never be able to go back; that I was losing relevance; that I was never going to make as much money as I wanted to as a freelancer.

Even though the benefits of my freelance life were obvious—I was writing and creating much more than I used to, traveling more, touching more grass, working less hours—I still felt unsafe.

In freelance life, your monthly income goes up and down. You’re paid 30-60 days after you invoice for your work, which can be 30-60 more days after you begin the work—paychecks can feel like a mirage on the horizon you just keep chasing. Your most lucrative, stable clients can be ripped out from under you with little warning, leaving you to scramble for more work. It’s been a brutal year for the economy, and all of those layoffs in tech and media companies trickle right down to freelancers, who rely on their corporate connections with corporate budgets to make a living. The media landscape is as bleak as it’s ever been. And many of us are tangibly feeling the squeeze of inflation.

So it’s true that making your living as a freelancer can feel scary and unpredictable. But Stella made me realize that safety in corporate, full-time jobs is also an illusion.

Work is not your family, and it will never love you back.

In my decade in the corporate world, how many friends and coworkers did I see laid off with no warning (not to mention the thousands of media workers I don’t personally know)? A coworker whose wife had terminal cancer got laid off after decades of devotion to the company. I witnessed managerial cruelty, a room full of employees told, “If you don’t like it here, work somewhere else.” I worked with people just trying to meet their KPIs, all the while filled with anxiety that they were next.

Your full-time role that comes with health insurance does not guarantee your safety. It doesn’t matter how glowing your last review was, how long you’ve toiled for a company, how dutiful you’ve been, or if you or someone you love is ill. Work is not your family, and work will never love you back. They will spend $15K to hire someone new rather than grant you the raise you ask for. They’ll outsource your job to a contractor whose zero benefits cost them zero dollars, and whose services they get to write off come tax season. If you die today, your company will post your open role online in two weeks.

We’ve all seen these examples play out over and over again. It’s delusional to keep believing that full-time jobs create personal safety, yet I did so for most of my life. And, of course, that’s what corporations want us to believe: It’s beneficial for them to lure you into feelings of safety and even gratitude so that you feel loyal to them, so you’ll dedicate a huge portion of your one wild and precious life to helping them meet their monetary goals. Meanwhile, their loyalty belongs to one thing only: the bottom line.

Stella gently pushed me: Work will always contain an element of uncertainty, just as every aspect of life does. Why not bet on yourself? Why not be your own boss? Why not keep trying to build the professional and creative life you long for on your own terms? Why not fold what you love into how you financially support the life of your dreams?

And if you fail, guess what? Corporate life will always be ready to welcome you back with open arms if and when you need it.

If I embrace uncertainty and push past fear, what could I achieve? I want to find out. I’m doubling down on investing in me. That means actively pushing back on a limiting scarcity mindset. It means intentionally investing in financial coaches and website designers and whoever else will work their magic to help me push my business forward. It means honoring schedules that help me guard my writing time closely. It means dreaming bigger, seeing a vision that pushes past my home office window.

After my conversation with Stella (and another one with my therapist who affirmed the same sentiment), I decided to stop applying to full-time jobs until at least 2024. Here I was building a life as a business owner and doing it pretty damn well, yet I kept distracting myself by applying to 5-10 jobs every month, which takes a lot of valuable time and energy away from the creative endeavors I actually want to be pursuing. (The hours spent crafting cover letters, tweaking resumes, and filling out applications compound quickly.)

I finally saw my tendency to fling out applications to full-time roles for what it was: an act of desperation. Despite the years of freelance work that I now have under my belt and the financial success I’ve had so far, I was afraid to fail. I was still looking at work and safety through my father’s eyes.

I’ll be honest with you: I haven’t stopped applying to jobs completely. You can’t unlearn decades of capitalistic values and self-preservation instincts overnight, okay! Plus, I get a lot of job FOMO; I don’t want to miss out on a big opportunity, or my next steady client, or a quick cash grab that could pay my rent next month. But I have stopped spending so much time scouring the media jobs newsletters, and I am much more conscious of my instinct to drop everything to apply to an alluring gig. And I’m making a conscious effort to focus on the one thing I know I want to do more: pitch my own ideas.

Most importantly, I’m now aware of some of the foundational emotions and experiences that continue to subconsciously drive how I make choices about work and money today. For most of his life, my dad didn’t have the privilege of pursuing joy—he was busy surviving. Despite many challenges, he achieved what success meant to him, and passed those benefits on to his children.

The greatest gift my father gave me was the safety, freedom, and encouragement to thrive. There is no better way to repay him than to do so.