top of page
  • Writer's pictureJennifer Willey

Riding the Confidence Roller Coaster

Updated: Mar 21, 2018

Welcome to Wet Cement's inaugural blog post. In the coming weeks and months, I will share stories to hopefully inspire, enlighten and empower you to “make your mark.“ I'll open up about how my confidence has ridden a perennial rollercoaster throughout my journey, and how it ignited my mission to uncover how and why many women have a harder time communicating confidently--and how we can overcome this.

What is confidence anyway? According to Psychology Today, Confidence can be described as a belief in one's ability to succeed. Striking a healthy balance can be challenging. Too much of it and you can come off as cocky and stumble into unforeseen obstacles, but having too little can prevent you from taking risks and seizing opportunities—in school, at work, in your social life, and beyond.

Dr. Jim Taylor even goes so far as to say that "Confidence is the most important psychological contributor to performance in the business world because you may have all of the ability in the world to accomplish a goal, but if you don't believe you have that ability, you won't use that ability to its fullest extent in pursuit of success."

In my career, I've had far too many ups and downs related to confidence to mention. To understand how to thrive, I had to take a look in the rear-view mirror to where my journey began. After being told I wasn't cute enough to play my own father's daughter in a TV commercial (rockbottom on the confidence charts at the age of 6!), I finally got a boost by appearing as a cast member--but really a "character"--on the TV Show 'Child's Play,' (the game show, not the movie with "Chucky!").

Another win in the confidence column came when I was certified as one of the youngest fitness professionals when I turned 16 (Back in the late 1980's, we were actually called "aerobics instructors"--ahhh, the days of shiny spandex unitards and leg warmers). But then again, being told by my student that "I would be pretty if I just wore makeup" didn't help too much.

I learned to manage multiple egos working on "Live with Regis and Kathie Lee" (the 'original Live with Kelly and Ryan') and "Good Morning America," but was told that even though I was a Teaching Assistant for Public Speaking at Cornell University, I was only qualified to answer the phone. Ouch. But by the end of the summer, the leadership team said they thought I would be better in front of the camera (than as a Producer), and I should pursue a career in TV News (blast off on the confidence scale!).

I worked my way up from anchoring local radio news to becoming a local celebrity myself, as a TV News Anchor and Reporter at the age of 21. (While you may be wondering why a bellhop is anchoring the news, that photo is in fact me in the mid-90's). I have many stories to share about those years... stay tuned for that.

Why would I ever leave TV News?

Well, after feeling:

a) Intellectually drained writing for a 4th-grade reading level

b) Tremendous anxiety after knocking on the door of a serial killer all by my lonesome (we didn't know the victims' neighbor was the killer at the time) during my time at WENY-TV in Elmira, NY (yes, it was called 'WENY'--making it a little challenging to feel like a serious journalist), and

c) Being told I wasn't attractive, blonde or diverse enough to earn a seat at the anchor desk in a major market (when I was ready to move on from WLTX-TV in Columbia, SC), I switched gears. That kicked off a career in consulting, business strategy, sales and marketing in digital media and tech.

Which brings me to today, as I turn to the 'dark side,' re-entering the world as an entrepreneur--leaving behind the corporate ladder and my "C-level title" to make the time I have here on Earth matter more by advancing women at work.

How did I get here? It all started about a decade ago, when my boss at AOL (now Oath), was helping me decide between my next role within the company. I had the good fortune of choosing between two incredible jobs:

a) joining the newly-formed Branded Entertainment division, working with two incredible Google Alums, Karen Cahn (now founder of iFundWomen, a crowd-sourcing platform for female entrepreneurs) and Erin Clift (now leading Global Marketing and Partnerships for Google's Waze), or

b) joining the inaugural Industry Practice Team, leading the Consumer Packaged Goods (CPG) and Health verticals across all of AOL‘s properties and assets, including sites like TechCrunch, HuffPost, Engadget and (now OnebyAOL), to name a few.

My boss at the time, Tim Castelli (now President of iHeartMedia), asked me which role I was going to pursue. I shared that while working in branded entertainment would be fun, challenging and I would have the opportunity to learn from two INCREDIBLE women, I believed the role as Industry Practice Head of CPG and Health would help me grow tremendously from a business strategy perspective. Only reservation? Having the phrase 'practice head' in my title--as you might imagine, it is not exactly ideal as a woman in business.

“So you are going for the industry practice role, huh?“ Tim asked. When I replied that no, I wasn't going to, Tim was dumbfounded. "I'm confused. Why not?" My response: "I don’t think I am really qualified for that. I feel like I only have 70% of the qualifications for that role... so I’m not going to throw my hat in the ring." I wish I had taken a picture of Tim’s face--a mashup of disbelief and anger.

“Are you telling me that you are actually going to pass up this opportunity because you think you aren't qualified enough? That is the difference between a man and a woman. A man would do just the opposite. If he felt he had 30% of the qualifications, he would go for it and find a way to make up the other 70% once he was in the role. And here you sit across from me telling me you have 70% of the qualifications and you aren’t even going to pursue it."

I had no words. You see, this was the first time I ever realized how differently men and women approach work. “If the industry practice role is what you want, you need to go for it,“ Tim pushed. I nodded my head and agreed. Before I officially pursued it, I asked a few of my closest male friends and mentors at work, who I knew would give it to me straight--and all of them agreed with Tim's perspective.

So I did it. I threw my hat in the ring for the role, and got it. I learned a tremendous amount about business planning and strategy from John Burke, who founded the industry practice for Google a decade earlier.

This moment stands out for a few reasons:

1. It kick-started my journey to understand how and why women approach work very differently. That day, I committed myself to the advancement of women in business.

2. It underscored for me how important men are in the advancement of women. We can't go it alone. I'm thrilled #mentorher is an effort the fabulous Sheryl Sandberg is highlighting. In this post #metoo world, we need to collaborate more closely, not create a chasm between men and women in the workplace.

Since this conversation with Tim a decade ago, others with the same mission have been trying to get to the bottom of why women and men behave differently. You may have even heard about the "Hewlett Packard Internal Study" where supposedly men were confident enough to apply once they met 60% of a job's qualifications, but women would apply once they met ALL of the criteria. I say supposedly, because while it's been cited in The Confidence Code by Katty Kay and Claire Shipman, Sheryl Sandberg's Lean In, and the Harvard Business Review, the actual study results are somewhat elusive, according to Gender Equality Expert Curt Rice.

But what matters is that there IS a difference. Throw back a few glasses of vino with the women in your life and I bet you will see a lot of heads shaking in agreement. Which is why I'm now devoting my life to helping women overcome behaviors just like this--so we can confidently pursue the roles we deserve.

What do you think? Have you seen the confidence divide in action with your colleagues, your friends or yourself? If you have a similar story to share, please do so here in the comments section below. It may serve as a confession of sorts, and help relieve your conscience to get it off your chest.

Alternatively, if you had a "Tim" in your life who pushed you out of the nest, give him or her the credit they deserve.

Either way, your story may help other women --and men-- to know they are not alone.

I promise to share stories of my ongoing rise and fall of confidence throughout my career, and the lessons I've learned along the way--not to mention the many embarrassing photos, videos and stories. I hope you come along for the ride. Follow me on Facebook, LinkedIn and Twitter so you don't miss it--and thanks for reading!

(Photo courtesy of Your Story Photography)


3 comentários

Allison Braham
Allison Braham
12 de mar. de 2018

LOVE this! So many truths for so many of us to relate to. As someone who has know and benefited from your mentorship for so many years on the business side of things, I'm disappointed to say I missed the childhood star phase, but I always knew you were a star Jen and I'm glad this new venture will allow you to share your light with so many more women xx


molly elmore
molly elmore
12 de mar. de 2018

Wow - this post brought up quite a few memories from the past. In my experience, there is absolutely a difference between men and women in their careers. I think many women, myself included, really believe in a meritocracy and wait until they have earned something for it to be awarded. This is in line with your perception of needing to be qualified. In my case, it was with promotions. I always waited until I was awarded a promotion, which fortunately happened many times. Except this one instance where I really wanted a promotion, primarily so the slot would not be filled yet again with someone who had the same experience level as myself. So I wrote a l…


andrew kingery
andrew kingery
12 de mar. de 2018

Love it! Thanks for sharing your story. I see the confidence divide often. In part it seems the brain likes to compare the current state with the end state without regard to the journey. If you can take the first step, you can likely climb the mountain. But the brain wants you to be able to climb it today for the journey to be possible. Changing how we talk to ourself is one of the most important things we can do.

bottom of page