3 Questions to Consider Before Starting Over

Are you ready to change careers? Here are three things you should ask yourself before you make the jump.

woman working career
Woman working career
(Image credit: Getty Images)

Am I crazy? My friends sure thought I was. While they were collecting pink slips and unemployment checks, I was toying with the idea of quitting my cushy career. I had the kind of job other people envied – only in my twenties, I held a prestigious position at a Fortune 100 company. I had a handsome salary, full benefits, my own company car, and ample access to our suite at the Staples Center in Los Angeles. Only an idiot would give all of this up in the middle of a recession right?

So many thoughts raced through my mind. What would I do next? I'm certainly not going to be making the money I do now. Do I really want to start at the bottom again? What is my family going to think? Will I find work in this economy?

Ultimately, I made the leap of faith. I wasn't working in a field that I was particularly passionate about and I figured that if I didn't see myself there in ten years, why stay another ten months? Or even ten days? I eventually went back to school for my postgraduate degree in merchandise marketing (a world away from by Bachelor's in psychology) and am now in the infancy of career #2.

While never easy, here is what helped me make the tough decision to leave my job:

If I don't do it now, when will I?

I hated the idea of working my way from the bottom again, but I was in the prime position to do so. I didn't have a husband, children, a mortgage, or any other major life responsibilities. The longer I waited to change careers, the harder it would be.

"You can always make more money, but you can never make more time."

I sincerely thought my mother was going to try to talk me out of it, but this is what she said to me when I confessed my desire to leave my lucrative career. She reminded me that money is earned and spent, but once a second of time passes, you never get that second back. Life is so short, and you simply must fill your time with people, activities, and work that you love. And I firmly believe that if you do what you love, you cannot help but be successful, and the money will eventually come.

Which would I regret more?

In 20 or 30 years when I look back on my life, which would I regret more? The fact that I gave up my comfortable occupation, or that I never took a chance at trying something different? The question was almost too easy to answer.

My life is quite different now. After graduation, I moved to New York to pursue my dreams of working in fashion. Instead of driving my company car, I ride the subway. Instead of Laker games from a luxury box, I watch them on television. And while I now assist someone else instead of having my own assistant, there hasn't been a day that I've regretted my decision to start over.