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


Women are often taught to “play it safe” and avoid making waves if they want to get ahead. In the modern world, that approach has gone out the window, as women have realized that the best way to advance their careers is to advocate for themselves, even if that means taking a big risk.

Although it can be scary to take a leap of faith into the unknown — especially without a backup plan or safety net — most people don’t regret doing what they believe is right for themselves. Below, nine successful female entrepreneurs from YEC share the biggest career risks they’ve ever taken and why it paid off for them in the long run. Here’s what other women can learn from their journeys.

These entrepreneurs share the career risks that paid off for them.All photos courtesy of YEC members.

1. Founding My Own Startup

The biggest risk I’ve ever taken was to found my own startup, GiftStarter. I put in my own money, took out a second mortgage and took seed funding from investors. I ultimately decided to close the business, a platform to buy group gifts, last May. It was my biggest risk by far because it required so much. I have many battle scars from the endeavor that showcase all of the hard-learned lessons that I now implement daily in my current role as president and COO of Storm. – Arry YuTenta Browser

2. Starting A Business During The Great Recession

The biggest career risk that I have taken is starting a service-based business (without any IP to differentiate myself) during the Great Recession. I had lost my cushy corporate consulting position and was left without any safety net. After losing my job, I decided to start a low-cost business without much financial risk. Although it seemed crazy to my friends and family at the time, I was able to build a solid pipeline of loyal clients. – Kristin Kimberly MarquetCreative Development Agency, LLC

3. Dropping Everything To Take A Sabbatical

I started my first startup my freshman year. I loved it so much that it took over my life. I always told myself that I’d start traveling and working remotely when I graduated but my senior year I jumped straight into a new business idea. After a year and a half, I was feeling a little burned out. It seemed like I was just doing things that fit society’s definition of success. That’s when I knew something was wrong. I left it all behind to start traveling and get to know myself better. Sometimes we get so caught up chasing after things that we forget to take a break and reanalyze things. While I had no idea what would come from leaving, it turned out to be the best decision. I started a travel app and learned a lot about myself. – Adelaida Sofia Diaz-RoaNomo FOMO

4. Taking Maternity Leave From My Startup

I had twins after hiring our fourth person and while we were launching websites and big SEO projects. My business partner and I were in the thick of the day to day. Neither of us had taken paternity or maternity leave and did not know what to expect. I came back after two months. I used the first four weeks to get up to speed, then went full-time. I have zero regrets for having children or taking maternity leave. We should have done better in setting my business partner up for success with an operations manager or account director. I should have taken the full three months instead of trying to come back a few weeks early. My business partner is male and I felt like I had to prove I could do it all, when, in reality, I had to set new boundaries both at home and at work. – Kerry GuardMKG Marketing

5. Moving Out Of The Country For A Contract

I left the country and moved to Paris for a year to take an opportunity to work with startups in the Series A phase. This was a huge risk — there were no guarantees behind their success. There was no telling if they would succeed and I could be out of a contract within three months. My job was to help them scale within two months and raise investor money to grow even further. The early stages were bootstrapped completely — but I received the reward of helping one of the startups in the healthcare space scale to $1 billion in revenue in a year and a half. This experience was rewarding in itself and if I could go back and repeat it, I would do so in a heartbeat. Make moves, do things alone and reap rewards. – Sweta PatelSilicon Valley Startup Marketing

6. Opening Business Number Two

This past spring, a company purchased some of my curriculum. I had two options — work on the business that was tried and true or take a leap and start the brick and mortar I had been dreaming about. On a whim, I saw a rental property — it was gorgeous with absolutely stunning light. A lot of work needed to be done, but the price was right. So instead of experimenting with the business I knew so well, I decided to take the leap and open a collaborative collective and social space for and by women. The name? Fearless. While this might look like a huge risk, it was calculated for me. I had failed, a lot and often, with my other business and I felt I was ready for the next level. And this was it. Take calculated risks, whatever that means for you, and make it happen. Be fearless. – Jen BrownThe Engaging Educator

7. Expanding To Other Locations

The biggest risk I’ve taken in my career was expanding from one location of my small business to three locations. It required a lot of financial risks, learning new skills, delegation, hiring for key roles and a lot of work and planning. There were financial challenges and it was really scary at times. A few years ago, another entrepreneur told me that the success of my first location was “luck” and not to count on it. I loved proving him wrong! – Rachel BeiderMassage Outpost

8. Having Children As A Solo Business Owner

It was terrifying being in the early stages of running my own business with a baby on the way. I knew I wouldn’t get a proper maternity leave, but I also understood that it would be challenging to run things as smoothly as I was able to pre-kids. When my son came into the world, I had serious complications at his birth and nearly died. I spent the next year recovering and running the company remotely from home. I had to shift my expectations for that year. I did not focus on growth but instead focused on stabilizing and streamlining processes in preparation for future growth. The business thrived! We grew a bit that year and nearly tripled our revenue the following year. – Rachel LipsonBlue Balloon Songwriting for Small People

9. Publicly Sharing My Failures

A year ago, I shared a post on LinkedIn about a failure of mine and it accumulated over 20 million views in less than three weeks. It was a story about having to fund my team’s salary on my personal credit card. But I was ashamed to tell it because I felt like I was setting myself up for public humiliation. To me, it was a big risk putting myself in such a vulnerable position, especially since my team didn’t know about the situation, but the responses were absolutely incredible. People related to the fact that entrepreneurship is not glamorous, but rather a long tough journey with few ups and many rock bottoms. I received support that I would’ve never imagined. It was life-changing. I began bringing in more business and soon got asked to be a public speaker and special guest on podcasts. – Jinny Hyojin OhWANDR

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