What a Year of Being Fearless Taught Me

by Andy Caron

posted on 06-27-2019

This past year as a member of the Fearless 50 has been a time of transition and change, sometimes aggressively so, and so it has seemed a fitting theme for my year: fearlessness.

I took over co-leadership of the Chicago Marketo Users Group (ChiMUG) in 2017, and I was nominated to the Fearless 50 a year later for my efforts building Marketo’s presence in Chicago and promoting excellence in my local market. The inaugural class of Fearless 50 was based on nominations, and while you could name yourself as a candidate, it frankly never occurred to me. I thought the Fearless 50 program was for proven leaders, but after being named I started to understand that the program was really targeted at growing leadership. The chance to be coached by someone like Sarah Kennedy and the potential to expand and deepen my connections with future leaders were exciting prospects. I took the opportunity to challenge myself with the prospect of fearlessness, to go all in. Little did I know that becoming a member of the Fearless 50 would coincide with some of the greatest tests of fearlessness I had yet to experience both personally and professionally.

Road to fearless

My journey in marketing began in 2010 when I joined my first startup. Still reeling from the 2008 crash, I was the twelfth hire in an extremely bootstrapped company. No one really identified what I was doing as marketing until a year after I was hired. When we upgraded to Marketo Engage in 2012, I took on the tool not knowing what it would mean for my career.

Six years later, when I was nominated to the Fearless 50, I had progressed to Director of Inbound & Automation at a different startup. I had a five-year plan focused on getting me to the title of Chief MarTech Officer or CRO. Shortly after joining the inaugural class, I was offered a VP level role with a new organization. It seemed almost too good to be true, I discussed it with my Fearless 50 coach, and I agonized over whether or not I was ready. Ultimately I accepted the challenge and rolled up my sleeves. At the same time, we made the decision for my husband to go back to school. Not long after joining my new team, I discovered, VERY unexpectedly, that we were expecting our first child.

It was a lot to take on all at once, and staring into the face of all of these gifts and challenges seemed so closely aligned with the theme of fearlessness, it appeared almost preternatural in its cosmic alignment. My days were spent shifting between settling cross-departmental strife, client calls, and gutting our old Marketo instance; nights were spent digging through our attribution data. I was deep in the thick of building out a department, preparing to be a mom and holding it down for the family. And then it happened… the week before Thanksgiving, I was laid off, along with 20% of my company.


The layoff was a sad reality for my company and my team. The entire marketing department was liquidated. The day it happened, I came home focused on fearlessness and buoyed by the fact that I had accomplished something for my team that day that made me feel like I finally understood true leadership. My response to the news was to insist on being the one to tell my team despite the HR protocol and to negotiate better severance packages for them.

A week later I had booked consulting work, and before I delivered our son, I had a contract signed with a top Marketo consultancy, Revenue Pulse. I faced the situation with a rational mind and the strong backing of years of Marketo Engage experience and certifications. Fearlessness in marketing, as in life, is not a lack of fear as they say. It is having confidence in your skills and value. Your intrinsic value and accumulated knowledge are your greatest assets. Knowing what those are and how to leverage them is the first step toward, if not fearlessness, then certainly less fear.

Lessons in fearlessness

So what did I learn from all this? Several things:

If you’re lucky enough to find something you love (or even like) don’t be afraid to go all in on it

I’m a firm believer that the nonsense about not putting all your eggs in one basket is just that, nonsense. Pick your basket wisely but invest fully. Having that first investment in a solid place (Marketo Engage for me) allows you to take risks with other baskets (VP at a startup).

Follow the ‘Say YES’ and ‘Don’t Ask, Don’t Get’ principles

The answer is always ‘no’ if you don’t ask. When people ask you to do things, and you say no, they stop asking. I’ve applied to speak at Marketing Nation Summit every year since 2015. This year one of my proposals was finally accepted, and what once seemed like an impossible pipe dream, speaking at Adobe Summit, became a reality.

You can only be a good or a great leader with amazing support

Whether that is the support of your mentors, your colleagues, your team, or the support you receive from your friends and family. There were times when I wasn’t sure I would have made it through the last year without sounding boards and cheerleaders. I was blessed to have a number of my Fearless 50 classmates become those people for me.

Work/life balance is absolutely the most important thing

But balance sometimes only looks balanced when you take a few steps back from it. It’s never going to be even. Sometimes you invest more in life and other times you have to double down on work. Returning to work at four weeks postpartum and then traveling for work at six weeks was insanity to most (even though no one would have batted an eyelash at a new dad doing the same) but while it looked like work, it was all for my family, and my family is my life.

This year has proven to me that experimenting, pushing yourself, asking why? and why not?, taking on challenges and asking for more responsibility, more ownership never hurt you. It’s proven that you’re never as prepared for change as you think you are, and that having support in your family and your work community is what helps you to be stronger, and more fearless. And it’s cemented the fact that we only discover our potential for fearlessness when we find, or put ourselves in positions of risk, and places where we can be scared.

The leading edge

Leadership hasn’t looked like what I thought it would look like. Leadership didn’t look like encouraging local Marketo Engage users to come to happy hours and kvetch about their woes to a group who actually understood what they were talking about. Leadership didn’t look like sitting my team down and telling them that all our grand plans were at an end and that they were no longer my team.

I’ve discovered that leadership is simply strength that empowers yourself and others to do and be better. My year in the Fearless 50, among leaders facing challenges equal to my own, taught me that. I’ve transitioned to a phase of coaching others and focusing more on their development than my own. I think this is part of the natural flow of leadership as well, moving from being in the spotlight to supporting from the wings, knowing that you will be cast in a leading role again in the future. Being willing to be what you need to be for others, regardless of what that might mean for you, that is what it truly means to be fearless.

To start your own journey as part of the next Fearless 50 class, apply here.

Topics: Future of Work, Career Advice

Products: Marketo Engage