Making the decision to leave a corporate job isn’t just about logistics—it’s about overcoming fear. Fear of financial instability, fear of judgment, fear of failure. These worries are natural, but they also have a way of keeping us stuck.
When I first considered leaving my job, I had a million doubts running through my head. What if I couldn’t make enough money? What would people think? Would I regret giving up stability? Looking back, I realize that most of those fears weren’t based on reality—they were just assumptions I had never questioned.
The truth is, leaving a corporate job doesn’t mean throwing your life into chaos. With the right mindset and preparation, it can be the best decision you ever make. Below, I break down the most common fears and misconceptions that hold people back—and why they’re not as scary as they seem.
Fears
1. “I Will Not Have Financial Security”
One of the biggest lessons I’ve learned is that making more money doesn’t necessarily solve your problems or bring lasting happiness. In my corporate job, I was always chasing the next salary increase, thinking that once I hit a certain number, I’d finally feel secure. But the reality was that no matter how much I earned, financial stress was always present.
When I broke free from the cycle of yearly raises and salary benchmarks, I started looking at my life based on what I actually needed—not what I thought I was owed or what I could buy. Ironically, the more I removed material things from my life, the happier I became. I still love my bike and surfboards, but the endless cycle of needing more clothes, new shoes, matching towel sets, or perfect wall art—it’s all overrated.
My income has dropped by 50%, yet I’m saving more now than I ever did in my corporate life. How is that possible? Because the more you make, the more you spend, and the less you track. When you work hard for every dollar, you think twice about your spending. You develop a passion for what truly matters, and you become more intentional with your purchases. Being financially secure isn’t just about your salary—it’s about being financially smart, and you can absolutely achieve that while making less money and living a better life.
At the same time, quitting my corporate job didn’t mean settling for less forever—it also opened the door to new opportunities. While I currently work seasonally to support myself, I’m also building projects and business ideas that could one day surpass what I was making in my corporate role. A steady paycheck provides security, but it can also keep you from taking the risks that lead to greater personal and financial growth. Sometimes, stepping away from stability is the only way to see your full potential—both in life and in what you’re truly capable of earning
2. “People Will Think Less of Me”
Actually, it’s quite the opposite. The most common response I get when I share my story is, “You’re living the dream.”
Sure, I have to remind people that my lifestyle comes with its own set of struggles, but at the end of the day, I wouldn’t trade my current challenges for my old corporate life. People admire the freedom and courage it takes to step away from the traditional path and follow your own. Many people live with regrets, yet continue choosing complacency over chasing their dreams.
3. “What If I Fail?”
Then you try again.
No success story comes without failures. We learn from failure, we are humbled by it, and we grow because of it. When you take a risk and start something new, you have to be prepared for ups and downs. Challenges will come, but the rewards are worth it.
4. “Starting a Business or a New Job Later in Life Is Risky”
Staying at the same job is risky. Why not try something new?
Every choice comes with risk. The way I see it, I’d rather take the risk, try, and fail than always wonder, “What if?”
And maybe you don’t know exactly what you want to do with your life. That’s okay. Exploring different jobs and lifestyles is exciting and gives you perspective. I spent ten years in finance doing similar tasks. In the five years since quitting, I’ve worked in multiple industries—being a horse tour guide, a bartender, a contract worker, and an entrepreneur. Each job humbled me, taught me new skills, and introduced me to different walks of life. I grew more as a person in those experiences than I ever did sitting at a desk.
Misconceptions
1. “I Can Never Go Back to Corporate”
This depends on how you leave your job. My biggest piece of advice: Always leave on good terms. Better yet, leave on great terms.
Quitting for a new job in the same industry can be tricky, but when I left, I was honest with my bosses. I told them I wanted a change in lifestyle. Were they happy? No. But I gave a long notice, expressed my appreciation, and left on a positive note. Keeping doors open is always a smart move.
Also, depending on your experience, there are always jobs out there. Sure, you might have to work your way back up, but leaving might also give you clarity on what role you truly want.
2. “My Resume Will Be Judged If I Quit”
Yes, some employers may question a gap in your resume. But many hiring managers are becoming more progressive and understand that taking time off to realign yourself is not uncommon.
If a company judges you solely for a career gap, consider whether their values align with yours. Most interviews will give you a chance to tell your story. Plus, career changes showcase adaptability, and the variety of jobs I’ve worked has only enhanced my skillset.
3. “I Have to Build a Career Based on My College Degree”
I chose my career at 19 because my dad gave me great advice: “Get a degree with a hard skill like accounting.” But did I think deeply about what I was passionate about? No—I just wanted to pass my classes and get a job.
Following the traditional path led to a successful career, and I don’t regret that. But now, I can barely survive the three hours it takes me to do my taxes and wonder how I spent 10 years in spreadsheets! Now, I ask myself: What excites me? What tasks do I actually enjoy doing? That’s how I’m shaping my new career. It’s not always easy, and I’ve had to work odd jobs along the way, but I’m excited about the process.
Your college degree is valuable, but the career you choose at 18-21 doesn’t have to be your forever path. The years I spent in finance taught me the work ethic I now apply to my entrepreneurial journey.
4. “I Won’t Be as Successful as My Friends”
How do you define success?
In my early 20s, my friends and I were all making money, living in the city, and thriving in our careers. But as time passed, people settled down, got married, moved away, and redefined success in different ways.
For me, success is about living freely and happily. For others, it’s their salary, job title, or business achievements. The truth is, we are our harshest critics. True friends will be happy to see you thriving, no matter what that looks like for you.
Even my wealthiest friends aren’t worried about me because we have different wants in life. And at the end of the day, the things that originally brought us together—our values, experiences, and mindset—still remain.
Final Thoughts
Leaving a corporate job is a leap of faith, and it’s natural to have fears and misconceptions. But if you’re feeling the pull toward something different, trust that the unknown is not as scary as it seems. Life outside the corporate world isn’t always easy, but it is rewarding. And the best part? You get to define success on your own terms.
