Nothing ventured, nothing gained
Few emails from your boss that begin with the subject line “Confidential” are harbingers of good news. After all, good news is meant to be shared. Celebrated widely. And everyone knows you praise in public—and punish in private. Sitting in the driver’s seat of my car on a gray Monday morning, I knew this email would be the latter.
The words from my boss formed a pattern I had come to know all too well, praising my work as “excellent” only to segue into a list of my perceived failings. Didn’t I realize how poorly it reflected on her when I worked from home?! The CEO would notice! She questioned the balance of my projects. My PTO schedule. My level of engagement with the role.
Exiting the car and heading to the coffee shop, I wondered how my work could be so “excellent” (her words!), yet my failures so numerous. Of course, I could meet with her to litigate the email, tackling the comments point by point, but where would that get me?
Because it’s true; I did feel disengaged—I had told her so only the week before, hoping for some guidance. None of the projects promised to me in the interview process a year earlier had materialized. I wasn’t growing or stretching my skills. The business itself wasn’t stable, and when I joined the company after five years at one of the world’s largest management consulting firms, all I wanted was a little peace and kindness.
I felt despondent as I grabbed my drink and took a seat opposite Kevin, my longtime mentor and trusted former boss from my formative years at the consulting firm. We were meeting that day, quite fortuitously, for one of our bimonthly catch-ups. After working for the firm, Kevin had struck out on his own and found success as a freelance communications consultant. As I filled him in on my job and the foreboding email, his advice was clear.
“Yeah, you gotta get out of there,” he said with finality.
“Several years of therapy to treat my PTSD had reshaped my tolerance for dysfunction.”
I clutched my iced oat milk latte like a lifebuoy. I knew he was right—something had to change, and soon. I’d known for a while that this company wouldn’t be my long-term home. Several years of therapy to treat my PTSD had reshaped my tolerance for dysfunction. The younger me would have stayed, agonized, and suffered in silence for the consistency of a regular paycheck and health benefits. But now? What did I really want?
Of course, I knew what I really wanted: to be a travel writer. The dream I had shelved since college was now front and center, demanding my attention. Daring me to pursue it.
Kevin told me I lit up as I talked about my new travel blog and upcoming trips. My energy noticeably shifted. We discussed how I could balance opportunities for freelance communications work, while leaning on my savings, to make ends meet as I pursued my real passion.
As we talked and problem-solved, the contrast between his supportive, caring mentorship and my boss’s cold critique couldn't have been starker. Clarity cut through the doubt: I couldn't waste another moment in a place that saw me as a problem rather than a person.
My decision that day was swift. After finishing my coffee and saying goodbye to Kevin, I drove home, prepared a transition document, had a final conversation with HR, and formally resigned my position via a short, polite email. No conventional two-week notice. No waffling. No turning back. Door closed!
Those first few days after quitting, I was hit by an intoxicating adrenaline wave of freedom and relief. The high of making a bold move was real… and so was the crash. Now, I face the daily realities of freelance life. Every day, I confront choices about how much work to take on, how to manage my finances, which sacrifices I’m willing to make, and how to stay true to my new path—a dream I’d kept on the back burner for 10 years.
These aren’t easy decisions, but they’re mine to make. It's a precarious dance of passion and pragmatism. I’m finally shaping my days into a vision that feels right for me. I’m opening myself up to learn and grow and stretch in new ways.
It’s only been a few weeks, but here’s what I’ve realized:
Waiting for certainty is often the riskiest move. People languish in jobs they don’t like for too long, which serves no one, especially not the person feeling stuck. The greater risk— to your well-being, your confidence, your self-worth—often lies in inaction. The power to change course really does lie within! It may not be easy, the path may not be clear, and it may take some time, but the first step is ours to take.
You can change your mind. I recently listened to a podcast where Nell McShane Wulfhart, a professional decision-making coach, said that almost every decision is reversible. And it’s true! Even if it might not feel that way at first blush. If I decide freelancing isn’t right for me, I will pivot again. I have to trust that I know what’s best for me. And, importantly, I have to believe that I can make cool shit happen!
It’s ok to fail. It’s important to say, this story isn’t about quitting your job the moment it feels hard. It’s more about recognizing when it’s time to move on and being okay with making that choice. Life’s little failures don’t define us, and we waste too much time and energy worrying over choosing the right path. We live in stagnation, in hesitation, which is the most stressful place to be! Tennyson had it right when he said, “It's better to have tried and failed than to live life wondering what would've happened if I had tried.”
As for what comes next, I honestly don't know. Reading that “Confidential” email marked the end of one chapter, and with my resignation only a few weeks behind me, I’m just starting on the first page of another. This whole adventure could still go south! But if it does, that’s okay. I’ll face it, learn from it, and then make the next move. That's the real thrill of this journey—not knowing for sure where it's heading but trusting that I'll figure it out.
Amanda Sims is a freelancer and travel writer sharing her adventures on her blog Amanda on Arrival.