Finding The Courage To Become Self-Employed

Guest Post by Nicole Catenazzi

Photo by  Katie Benfey

Photo by Katie Benfey


I’ve never described myself as a risk taker. Adventurous, maybe. Independent, definitely. But, risk-taking never felt like part of my genetic makeup, especially when it came to my career. Maybe it was because I landed my first job at the tender young age of 14. Or, maybe it was because I had only ever worked for someone else. Whatever the reason, at the end of last year, when I quit my full-time to become self-employed, it felt like I was taking the biggest risk of my life.

The road most travelled

Making the leap to entrepreneurship felt particularly tricky to me. I was a self-described post-secondary success story. I loved my university experience, excelled in my studies and was on a reasonable career track in line with what I expected to get out of my degree. While I was checking off all the expected boxes, I also found myself exploring newfound passions in my free time through yoga and creative writing.

A few years in, and several rungs up the corporate ladder later, I couldn’t shake the feeling that, even though I was a good employee, I didn’t love my job. The more time I spent thinking about it, the more I realized that actually, I wasn’t going to feel fulfilled working for anyone. Especially if it meant taking time and energy away from doing what I loved.

Photo by  Katie Benfey

Photo by Katie Benfey

Overcoming self-doubt

However, I leaned on the steady income, the regular pay cheques for stability. I couldn’t imagine how becoming an entrepreneur was even possible, let alone sustainable.

I felt a lot of fear around the idea of working for myself. My longing to leave the office world led to more doubt-riddled questions than encouraging answers.


I knew that self-employment would feed my soul, but would I still be able to put food on the table? What would people think? What if I ended up broke and in debt?


Silencing the critics

After months of irrational debate with my inner critic, I was no further along in doing what I felt like I needed to do. All the questions I was asking myself were focused solely on the extrinsic value of my career, and what was at stake if I failed. Yet the reasons for wanting to leave in the first place felt more like an intuitive calling.

That realization helped shift my perspective. I began to focus on what I could gain if I succeeded. Becoming self-employed would give me the ability to say yes to opportunities that excited me (and say no to those that didn’t). It would grant me the freedom and flexibility to work wherever, whenever I wanted. Most importantly, it provided an opportunity  to build a meaningful life aligned with my personal values.

Photo by  Katie Benfey

Photo by Katie Benfey

Becoming self-employed

With those intrinsic goal posts in mind, suddenly, I couldn’t risk not taking the leap to become self-employed. Working for myself became a non-negotiable imperative. So I spent the next six months doing everything I could to feel prepared. From dissecting budgets, getting creative with income opportunities, building my writing portfolio, planning my dream retreats and workshops—and coming up with a few hypothetical back-up plans.

Even with all that planning, I never felt fully ready to leave my job and become self-employed. But with some supportive counsel from friends and family, I knew I just had to go for it. To be fair, it still took me the first half of 2018 to get enough courage to give notice. Even then, I gave two months instead of two weeks, so that I could beg for my job back in case I changed my mind.

Defining success

There were many reasons why I felt like self-employment was risky. All of them linked to my desire for financial stability. To be honest, I never worried if I was making the right decision from a values-based perspective. I had no doubt in my mind that at this point in my life, I was ready to turn my passions into my career, even if I wasn’t exactly sure how. As long as my needs for freedom, flexibility and fulfillment were met, and I enjoyed my work, I knew I’d feel like I had succeeded.

Within my first year of business, I led two immersive yoga retreats in the south of France, and nearly a dozen workshops. I also wrote tens of thousands of words for companies that I respect and admire. Am I earning what I did while working for someone else? Not even close. But when I measure my success based on how closely what I do aligns with my values, I have abundance in spades.


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