Surrounded by boxes of pizza and eager interns, I felt a shock of recognition listening the communications manager who had agreed to speak to my charges. She said that finding and forging her career path was “simple.”

“I knew exactly what I wanted to do when I was in high school and editor of the school paper. I studied journalism in college and got a job.” She had worked in corporate communications for an international travel outfit, a well-known natural beauty brand and a global coffee company, which is where we met. She added that she’d always been focused on writing and editing, even in high school.

I was, too, in high school. Like my guest speaker, I’d written for the school paper, plus I’d edited the yearbook and competed in journalism contests. So, why was she the head of a communications division and I was wrangling interns?

We made different decisions. I chose a school that didn’t offer a journalism degree, but did provide an independent, unique approach to learning. However, I lost focus and tried a variety of subjects and post-grad jobs, including managing a small business and recruiting. Employers would rave about my writing and find ways to use it, but I didn’t (and they didn’t) see me as a writer.

Inspired by my guest speaker, I started thinking about what I wanted to do with my writing as well as my goals. Several weeks later, approached her to be my mentor—and less than a year later, she hired me as a writer and editor for her team. Now she’s claimed the title of my “biggest fan.”

Between being the high school journalist, the corporate newsletter editor and the freelance writer I am today, these are the lessons I had to learn twice.

• Dream big. In the late 1980s, I wanted to be the editor-in-chief of Sassy magazine. When I was the fiction editor of my college’s literary magazine, I wanted to be a playwright. And, when I hit the real world, I wanted to pay my rent, so I took temp jobs and lost sight of the big dreams. Once I started focusing on my goals again, I refueled my writing dreams—and started pursuing them.

• Believe in yourself. I was so nervous the first time I turned in a writing assignment to my mentor—and I failed! She told me the style was unnatural, stiff and not at all what she expected from me. I’d used formal business language that I thought I should use. When I revised the assignment, using my gut instincts, my mentor loved it.Much later, when I was applying for my first writing job, my current manager said, “But you can’t write!” It shocked me to hear those words, but I was determined and still applied. When I got the job, I learned from someone else in my former department that my manager just didn’t want to lose me. Good thing I believed in myself and didn’t let her stop me.If you want to freelance, you have to believe in yourself. Your clients and prospective clients aren’t going to give you business if they suspect you’re unsure and timid.

• Fight limitations. Growing up in a small Texas town, the writing-related career options presented to me were newspaper editor and journalism teacher. The local newspaper editor even told us to find a better-paying occupation. I was determined to find more options for myself.Once I worked in corporate communications, the prevailing mentality was that if you wrote for an internal audience, you couldn’t write for an external audience. Are you kidding me? I fought hard to earn assignments that included press releases and other marketing materials.

• Invest in your word skills. My high school journalism teacher enrolled me in contests my very first year—and I continued those contests until I graduated. I didn’t take many writing classes in college, but I certainly relied on those skills to get me good grades. But I took them for granted. It wasn’t until about six years ago that I realized I should keep pushing myself, not just relying on mentors or talent. I took creative writing classes as well as copywriting-related courses and was amazed at the leap my writing took. My clients noticed, too.

Sometimes I wonder how my life would be different if I’d followed a journalism or writing path from high school. Most likely, I’d be where I am today. But I’m glad I veered of course, picking up business skills, new subject matter expertise and a diversity of experience. It’s made me a better freelancer, a more well-rounded writer—and it’s definitely provided me with plenty of juicy tales to tell.

What about you? Are there “lessons” you wish you’d learned the first time? Did you have to go through the same experience or situation more than once to figure out how to achieve a different outcome? Share your experiences in the comments.