10 Women Share The Biggest Career Risks They Ever Took (And Why They Paid Off)

Taking risks is always intimidating. It can be scary to leave comfort and safety behind and leap toward a potentially difficult and life-altering decision. But anything worth having rarely comes from taking the easy path.

To inspire you to take that “big chance” you’ve been dreaming about, we asked 10 members of Young Entrepreneur Council about the biggest career risks they’ve ever taken. Below they shared their stories about what happened and what they learned from following their instincts.

1. Jumping Into My Business With Both Feet

I left the comfort, safety and security of a full-time legal job to continue building my companies. I had a mortgage and monetary commitments, but luckily all the risk was on me. I had not started a family at that point, so I felt confident that, even if things didn’t work out, I could still dig down and rebuild. There is never a perfect time, so you just have to jump in with both feet and do it. – Lisa Song Sutton, Sin City Cupcakes

2. Betting On Myself

The biggest risk I’ve taken was starting Lunya. It was a huge bet on myself and, in hindsight, I think the mountain that decision set me off on was far bigger than I could have imagined. Looking back, the journey has taught me to value myself, time and the human connection more than I could have guessed. – Ashley Merrill, Lunya

3. Giving Myself Six Months To Achieve Startup Success

The biggest risk I took was quitting my job to start my own business. I gave myself six months, knowing it doesn’t work out 99% of the time. Six years later, Fattmerchant’s success has been crazy. When taking big risks, be confident in your ability to make the sacrifice. Nothing is guaranteed. In the end, you have to bet on yourself, always with the mindset that you’re OK walking away with a loss. – Suneera Madhani, Fattmerchant

4. Making A Quick Career Change

My biggest career risk was switching from nursing to web development rather quickly. I didn’t expect to enjoy web development as much as I did, but I also knew that staying where I was wasn’t an option either. I haven’t had a single regret about my decision, and if I could, I would do it all over again.  – Stephanie Wells, Formidable Forms

5. Buying Out My Business Partners

In 2018, I took on a loan through the SBA to buy out the two partners in the business I had co-founded. It was a risk because we had to take a loan and put our house up as collateral, and I needed to restructure our leadership team. I could not be happier that I made this decision, and I know that it’s been key to our team getting through this Covid crisis as well as we have. – Kelsey Raymond,