The Shriver Report – How I Discovered My Passion & Started My Own Business

Special Edition

How I Discovered My Passion & Started My Own Business

By Ashley Feinstein


My Dad calls me Mrs. Magoo.

I think it is because it may seem that I haphazardly plow through life full speed ahead and great things just happen to me.

This may be the case and I know I’m very lucky but there is something to be said for following your passion and doing what you love. Good things can’t help but be attracted to you.

I love this quote from Steve Jobs:

You can’t connect the dots looking forward you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something: your gut, destiny, life, karma, whatever. Because believing that the dots will connect down the road will give you the confidence to follow your heart, even when it leads you off the well worn path.

This certainly has been the case for me.

Surviving the Quarter-Life Crisis

When I started blogging about personal finance about three years ago while working in corporate finance, I had no idea it would be the start of my company, Knowing Your Worth.

I didn’t know anything about personal finance and thought that if I didn’t, other women probably didn’t either. I blogged about my journey because I wanted to share what I was learning in a fun and accessible way.

I had worked in finance since graduating college and while I was challenged, had ample opportunity and loved the people, at the ripe age of twenty five I had my quarter life crisis.

“Is this it?” I thought.

I had worked really hard to get the “right” jobs, proved I could hack it and continued to excel in the financial services industry.

I am a generally an upbeat person and worked at a great company so I was pretty happy.

I just wasn’t passionate.

Finding Your Passion

My “aha” moment hit me in spin class. I had been writing my blog for about a year, I was involved with some non-profit organizations with the mission of empowering women and I had accumulated many mentees who I coached on a regular basis.

It all started to make sense. I couldn’t see the five year plan but I could see steps ahead toward living a life that was more meaningful and fulfilling to me. My career started to have purpose.

Fast forward a year and a half while I was still working to build my business on the side. I wasn’t planning on making the jump quite so soon but when I received a promotion at work with much additional responsibility that required more time and training, I knew that it was time to leave. I feared I wouldn’t have the extra hours needed to build Knowing Your Worth on the side and I had this inkling that my business could grow so much faster if I dedicated myself to it full time. I was also pretty exhausted from working two jobs for the past year.  I had built enough of a cushion to really make it work without my additional job. It was time to make a change.

Making the Jump

I started with my direct supervisors and worked my way around the company, telling coworkers I was leaving to start my own business. One of them teased me because my whole body was shaking as I shared the news, but they all seemed genuinely happy for me and wished me the best. I offered to stay as long as they needed in order to transition the work and that turned out to be about four months.

This was a great time for Knowing Your Worth because I was able to ramp up my focus as I transitioned work to those replacing me. I’m still not sure if there is ever a perfect time to leave to start your business. I don’t think I could ever have had enough savings, revenue or future opportunities to make me feel 100% confident in taking the leap.

I do know that when you have an idea and framework for a business and some proof it can work, and you put yourself out there with your neck on the line to make it succeed, it will be the most exhilarating, fulfilling and sometimes terrifying time of your life. I no longer have to wonder “what if.”

In restrospect, I still didn’t know exactly what Knowing Your Worth would look like. I’m not sure I even know the full of extent of what it will become today now that I’m working on it full time. But I believe it will be big.

I also know that I wake up passionate about what I do each day and continue to plow full speed ahead on projects and ideas that are meaningful to me and the good luck keeps rolling in.

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user-avatar-picAshley Feinstein is a certified finance coach based in New York City and works with her clients on Knowing Their Worth, whether they are creating a financial plan, negotiating compensation, maintaining work-life balance or setting expectations in a relationship. She provides one-on-one coaching as well as workshops, lunch and learns and group coaching. Ashley started her blog, The Fiscal Femme, to share her passion for personal finance education in a fun and accessible way. She has worked in the financial services industry for more than five years: first as an investment banker and more recently in corporate finance. She graduated with a bachelor’s in finance from the Wharton School at the University of Pennsylvania. You can learn more at Ashley’s website,