Back in 2014, I took a risk and launched my own handbag company. Sure, it was scary but it was also exciting to dive into something new and see what I could build. I worked non-stop and got the handbags into cool retailers, press, and into the hands of customers all over the country. Despite these successes, there were a range of reasons that eventually led me to close the business. Was it sad? For sure. Do I regret starting the company? Absolutely not. Taking that risk was one of the best decisions I’ve ever made. I learned valuable lessons from both my wins and my mistakes, all of which were critical to my future successes. If you’re in the midst of debating whether or not you should take a risk, I’ve got 3 questions that could help you decide:

Question 1: If taking the risk doesn’t work out, will you end up in the same spot you’re at now? What do I mean by this? I’ll give you a real life example: when I finished graduate school, I had the opportunity to either take a job in New York or move to Buenos Aires to take on a consulting opportunity with the city. I also happened to start dating a very lovely man who lived in Buenos Aires. We barely knew each other but between the consulting opportunity, adventure of living in a new country, and exploring where things could go with the guy, it seemed like a risk worth taking. Sure, it was scary to say no to a great job offer to go live in a foreign country where I barely spoke the language, but I did it anyway. I had enough in savings that could sustain me there for a few months (let’s just say the salary with the city wasn’t going to cut it) and I assessed the risk: if things went awry with the job in a few months, I could go back to New York, crash with a friend, and get a job there. So, I went to Argentina. And, I’m so glad I did. Living in a new country taught me so much about myself, another work culture, enhanced my Spanish skills, and guess what!? That very lovely man from Buenos Aires is now my husband of many years!

Question 2: Will the risk negatively impact your financial situation? This is a big one. It’s really fun to think about moving to another city or traveling the world but let’s be real. Money matters. And, it’s definitely something to consider when assessing whether or not you should take a risk. Since I love real life examples, I’ll give you another one: I was once in a job where I was hardcore le miz. The company culture wasn’t my style and the role turned out to be completely different from what I thought I’d be doing . It was painful. All I wanted to do was quit, take some time off, and find the right next thing. But, when I assessed making that move financially, there was no way I could swing it. There were student loans to pay, a lease agreement I couldn’t break, and savings that needed to be saved. So, I had to suck it up and stay until I found the right next thing. It wasn’t fun but taking the risk of quitting that job without another one wouldn’t have been the right move for me at the time.

Question 3: If you don’t take the risk now, will you regret it later? I’m going to keep this short and sweet. If your answer is yes to this & #1 and no for #2, then seriously, just go for it!

*Disclaimer: these are my opinions and you should assess what makes the most sense for you!