We’re excited to introduce you to the always interesting and insightful Abby Calabrese. We hope you’ll enjoy our conversation with Abby below.

Abby, looking forward to hearing all of your stories today. Risking taking is a huge part of most people’s story but too often society overlooks those risks and only focuses on where you are today. Can you talk to us about a risk you’ve taken – it could be a big risk or a small one – but walk us through the backstory.

I have a desire to constantly stretch outside of my comfort zone. I grew up in a small rural town in Western Pennsylvania. I did pretty well in high school so when it came time to think about colleges, most kids chose from the same 5-7 schools. I wanted to do something different because – why not. I was the first person from my high school to go to a small liberal arts school in Baltimore, MD. It was a Jesuit university and I had never heard the term Jesuit and I was not even a catholic. It catapulted me into a new environment of meeting kids from NY, NJ and CT who were all coming from private catholic schools and similar upper middle class backgrounds. I was a fish out of water.

Through my experience at this university, I was also exposed to even the idea of NYC for the first time. It had never crossed my mind to go to NYC let alone live there and make a life there. But that seems to be THE PLACE TO BE for all the students I had met at my time at Loyola.

After graduating, I got a job with Morgan Stanley in Baltimore. It felt safe. It felt like the logical decision. And I was jumping out of my skin to get out of there. It was 2008 and we were in one of the worst job markets in recent times. The banks were failing and people were losing their jobs all around me. They did layoffs at Morgan Stanley and I asked if I could be laid off but they declined. I ended up quitting my job and deciding to just move to NYC and knew I would figure it out once I got there.

I moved my stuff from Baltimore back to my sisters house in PA. I boarded a plane from Pittsburgh to NYC with one suitcase and started a journey that would keep me in NYC for 11 years. I slept on a friends couch who was on a touring musical production. I applied for jobs on Craiglist. I got a position in the billing department of a large, elite law firm and it was enough to pay my bills.

While there I was accepted into a new hire training program for a financial software company. I knew it was the right place for me. I started there in 2010 and would spend the next 10 years there “growing up” and laying the foundation for my career.

It was a risk that I am very happy I took.

Abby, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

My background has been in financial software, technology, sales and executive leadership. I love solving complex problems for people and delivering solutions that genuinely help them do their job. I also loved the challenge of meeting certain goals and attaining certain accomplishments and achievements throughout my career.

After spending ten years at a very stable company, I was bored. I wanted to do something more challenging. So I jumped into the world of start-ups. I loved that I could wear so many hats and have such an impact right away rather than the bureaucracy of corporations. HOWEVER – this world also will take take take whatever you are willing to provide.

This is where I realized how susceptible I was to burnout. Without the corporate mandates and well defined boundaries that come with working at a large company, I was taking on way too much and working as much as humanly possible. I wanted to prove myself and without as many clear indicators on how I was performing I was always anxious that I could/should be doing more.

I cycled through several start-ups which is the nature of the work. Companies were acquired or merged and it led to a lot of new starts.

One particular bout of burnout was so terrible that I landed myself in the hospital after falling and hitting my head. It was an ah-ha moment for me. It became crystal clear that I had to figure out why I kept letting myself fall into burnout.

I DOVE into research around burnout and the causes and more particularly what about my past would lead me to getting myself into these situations in the first place.

Through this research and drawing on psychology, I developed a proprietary method for better understanding how to take better care of yourself and prevent burnout before it gets to a point like I found myself in.

I created my business, Abby Calabrese Coaching, which helps professional women who may find themselves in a similar situation. I have an online course, I provide 1-1 coaching, I do speaking engagement and then of course, I share a lot of great tips and sometimes humorous takes on it all on my Instagram @itsabbycalabrese.

I’m passionate about helping other women that may be in a similar spot. This is something I wish I had earlier on when I was going through these tough times and I’m thrilled to be able to help others through this. It’s very rewarding to me.

This whole subject manner is also an ONGOING work in progress and I think the more we can open the dialog around taking better care of ourselves and sharing what that realistically looks like the better it will be for women after us.

Alright – let’s talk about marketing or sales – do you have any fun stories about a risk you’ve taken or something else exciting on the sales and marketing side?

I was working at a start-up in the workplace management space (picture WeWork) and we were the smallest/newest player in the market. BUT what I loved is that the established companies in the space were DINOSAURS. They were using technology that hadn’t changed in decades and they really had no innovated much at all. We were a disruptor. It truly changed the way that people would be able to do their jobs in the space management arena.

I was pitching to one of the largest and most well-known social media companies in the world.

The odds were stacked against us as we had only even been in business a few years while our competitors had decades of experience and big name clients to tout.

HOWEVER, I focused on what this company was trying to accomplish rather than what we did for other clients. I truly listened to their needs and was able to position our offering in a way that directly solved what they were looking to do. While we were a much smaller company, I used that to our advantage. It gave us the ability to be incredibly agile and flex to their needs.

It took some crazy ideas and risks when it came to deciding how much we wanted to agree to develop FOR them but in the end landed us the largest and most well known client to date.

It was terrifying to be the little fish in the race but focusing on what advantages we had in that position allowed us to win the deal. It was a game changer for the company and led to the company being acquired shortly thereafter. I learned not to shy away from challenges where it seems like the odds are stacked against you. Sometimes it provides even more advantages being the underdog.

What’s a lesson you had to unlearn and what’s the backstory?

Bringing it back to what I do now – one lesson I had to unlearn was that you had to completely lose yourself in your work to find success. I had it drilled into me that hard work and constantly being “on” was necessary for success. From my childhood and what I saw depicted around me, the concept and notion of resting was looked down upon.

One of the worst things in the world was to be “lazy” and I looped in a lot of good and beneficial recovery tools under the blanket of “lazy.” I would feel enormous guilt for taking some time to rest, nap or just turn my brain off for a bit to relax. It created a lot of anxiety within me and a feeling of never being able to calm down.

Because I was finding a lot of success in my career, I thought it was aligned with me never taking time to unplug, But then I would go through bouts of burnout where I was completely exhausted/sick/unwell.

It took a scary hospital visit to finally knock some sense into me about the importance of self-care. Not going to the gym to lose weight or eating well to look good in clothes. Truly taking CARE of yourself and being kind to yourself.

That has been a GAME CHANGER for my life and has only HELPED me find even MORE success in my career.

Contact Info:

• Website: https://www.abbycalabrese.com
• Instagram: @itsabbycalabrese
• Linkedin: https://www.linkedin.com/in/abbycalabrese/