I am so happy about every bold, courageous leap I’ve taken in my career. The only regret? I often wished I leaped sooner. Here are a few leaps I’ve taken and why I’m so grateful I did.

Leap #1

After college I was living the life I dreamed of. I had a great job in TV journalism at ABCNews. I had my very own apartment in Manhattan. I had friends, dates, money, free time, and was learning & growing at a rapid pace. But something was off. When ABC announced massive downsizing and offered a cushy buy-out, I took it. I had nothing more than the desire to try something else. The leap took me back to Boston, a long-term relationship that I value to this day, and a new career in independent filmmaking.

Leap #2

In my late-20’s I was a fully-booked freelance video editor/director. I had a few bread-and-butter clients serving the ed-tech market, and plenty of freedom. But, I was doing 95% of the work and my clients were essentially just cashing checks (good for them!) I wanted to be my own boss. When I took the leap, I had a brilliant partner (shout out to Andres Ramirez!) but nothing else – no clients, no business plan, no sales or marketing experience. Well, the clients came quickly (everyone we’d worked with as freelancers), and we went on to run a multi-million dollar content agency for over a decade.

Leap #3

Fast-forward to my late 40’s: I was hitting the 10-year mark as a c-suite exec at a tech company. I’d learned a ton, accomplished a ton, and was tackling new challenges all the time. I loved my colleagues, and enjoyed the work. But I was burned out, like black-toast burnt. Once I left, I thought I’d get another job – I could command a high salary and offer lots of value. After a handful of interviews, and a few great job offers, I couldn’t get myself to ‘Yes’. Well, I had run my own business, and worked as a consultant between gigs before. But, the stakes were much higher as a single mom with a full plate of mid-life sized expenses. I took the leap. Now as a consultant/coach, I’ve helped dozens of clients improve their lives and their businesses and I’m living my life, my way.

Takeaways

Of course in these 3 decades I’ve made lots of life-changing choices but these are examples of leaps where the outcomes were far, far from certain. I don’t want to pretend they were easy or had immediate payoffs, neither is exactly true. But damn, I’m so happy I took them. So how’d I do it? I think it comes down to 3 things:

1. I have always believed that I could ‘figure it out.’ I started working when I was 14. I had so many different jobs where I proved to myself that I could learn, screw up, recover, and succeed. This has been an amazing foundation. (I’m talking waitressing, babysitting, and grocery store cashiering!)
2. I wasn’t afraid to fail. If something didn’t work, I could try something else. I’ve never been invested in one way of doing things or one kind of career.
3. I tapped into courage. People often compliment my confidence. But it’s really about mustering up the courage to do things that are scary and believe you’ll find your footing, one way or another.