To get something great, you must risk something good.

From 14 until 26 I had five jobs all of which I had conquered within six months of starting. By conquer I mean within six months I had mastered that job’s customer base, management, product, and the needs and wants of everyone working there.

I was always promoted, whether is was as a young teenager, to a management position at a retail store or at 20 being promoted to sales manager and responsible for over $50,000 a day in revenue while training and managing folks double my age. These were really good jobs especially for someone as young as I was, but they were not enough for me. Even with all the accolades and responsibility I always wanted more and hit my ceiling an order of magnitude faster than everyone else around me.

I wanted great and didn’t even know it.

The hard thing about wanting great is you have to walk away from a lot of good opportunities. What’s worse is how difficult it is for people around you to support you in walking away from something good. This has been a real challenge in my life: having to tune out all the people around me who just couldn’t understand why, in their eyes, I kept “throwing away” so much hard work and potential. I was continually creating good careers for myself, making more money than I ever could have imagined, so to everyone on the outside they just couldn’t help but think “why is she always walking away from something so good?” or to put it more bluntly they thought:

“She’s really going to screw herself someday”.

The hardest “good to great” chapter in my life I can remember is when I chose to leave a startup I had been an early employee at called drchrono. I gave that company my entire life. I worked for them when they were bootstrapping and had no money to pay me a salary and could only pay me on commission. Which means if I didn’t make sales, I was not going to be able to pay my NYC rent. I worked 100 hour weeks to ensure I found doctors to sell and then single handily supported those doctors once they came on board the platform to make sure they wouldn’t leave.

Hopefully, these words do not come off with a hint of regret, drchrono was one of the most important experiences of my life.

I was introduced to a world where a founder of a company actually builds, maintains and improves the product. But I was not the founder, so although this was as good as an employee position could get, it still was not great, and within 18 months I was on my way again. Everyone I knew told me that leaving something so good was the worst mistake of my life.

I left drchrono with just $5,000 in the bank (I had just gone a full year without a salary working there!). I had no idea what I was going to do, but I knew I could sell, I knew I could build a product, and most importantly I knew I had an ability to quickly identify what people want.

So as risky as it may have looked to the outside world it didn’t feel like a risk to me. In my eyes it was just the next step to something great and it was.