05/12/22 | Career

Failure and Fear, Self-Assurance and the Confidence Gap

Fran Hauser’s new book – Embrace the Work, Love Your Career – is an essential career companion, no matter where you are in your journey. Equal parts reflection, exploration and action plan, this guided workbook will help you become unstuck so that you can thrive in your career and ultimately live the life you want and deserve. We’ve included an excerpt below.

Redefine Failure and Fear

When I was at AOL (back in the dot-com days!), I was asked to pull together a strategy presentation for a few of our brands. I was given one month to do it. I had recently started working for a new manager, and I was eager to impress. I worked really hard on it. When the time came to make the presentation, I presented it not only to my manager but also to a group of colleagues. Let’s just say that the presentation didn’t go anywhere near as well as I had hoped. My manager used words like “You missed the boat on what I was looking for.” Yikes.

In this situation, what didn’t go well is pretty obvious: I under-delivered on the strategy presentation. My learning takeaway was that given that I had an entire month to complete the project (with very little direction), it would have been helpful to have checked in with my manager to make sure I was on the right track and meeting her expectations. The bigger takeaway for me was the realization that my approach to any responsibility included the idea that I never wanted to be a burden; I wanted to show that I was able to figure it out all on my own. It took this experience for me to realize how flawed this thinking is, and I used this learning moment to inform the way that I worked going forward. Self-assurance is cumulative; it’s based on both positive and negative situations. I like to think of failure as success-in-training. A setback can become a launchpad when you look at it as an opportunity for growth and development. In the end, what we show and tell ourselves is the most powerful tool we have to finding true self-assurance.

Self-Assurance: Facts Versus Fiction

If you struggle with feeling self-assured, you’re not alone. We all feel like that sometimes.

To this day, when I’m struggling with a decision or feeling insecure, I go back to the evidence. It’s really hard to argue with facts. I think about what I have done that’s worked, how I did it, and what the outcome was. When I was at Time Inc., I was asked to give a speech to three hundred managers, and I was nervous. A close friend told me, “Think back and remember a time when you gave a good speech.” It was simple but solid advice. Before delivering that big presentation, I thought back to a speech I’d given a few years before that my team said really resonated with them. I visualized that speech in as much detail as I could possibly remember: what I’d said, how I’d said it, and how it had felt to succeed. This made me feel far more confident.

This purposeful self-reflection will result in what I call evidence-based confidence. To develop your own, start keeping a list of your successes to look back on whenever those feelings of self-doubt creep up. Also include any insights you gained around the process to achieve that successful outcome. Self-assurance builds not just from wins but also from the confidence that comes with repeatable actions. For me, when I figured out the best way to prepare for a speech, I felt more in control before the next one because I could rely on a process that worked for me in the past.


Your Smile File is a powerful asset against self-doubt. Sadly, I’ve seen that many of the women I’ve worked with and mentored over the years are less likely to truly believe in their capabilities than their male peers. When Hewlett-Packard was looking to place more women in top leadership positions, they found that women were likely to apply for a job only when they believed they met a full 100 percent of the qualifications listed for the job. In other words, they applied only if they were a perfect match for the role. Men, on the other hand, applied if they met only 60 percent of the qualifications. That’s the confidence gap.

I admit I’ve been guilty of this at times in my own career. I was working at AOL when I heard that senior leadership was putting together a team to bridge the gap between AOL and Time, Inc. (both divisions of Time Warner). This opportunity sounded like a great fit for me, and I loved the idea of working on the Time, Inc. brands like Fortune, PEOPLE, and InStyle. I wanted to step up, but I was intimidated. I had never worked in magazine publishing, and I found myself second-guessing my own qualifications.

I had a male colleague at AOL who had the same level of experience as me, but unlike me, he jumped to make this move right away. Knowing that I had strong interpersonal skills, he encouraged me to join him. As it turned out, taking that opportunity led me to a whole new career at Time, Inc.

I now know that my colleague and I unwittingly exemplified the most common behaviors of our genders; it’s typical for men to step up right away, while equally qualified women tend to hang back and wait to be pulled in. So, if women are losing ground because we undervalue ourselves, what can we do about it? The first step, as simple as it may sound, is to be aware. If an opportunity comes your way that intrigues you but you think you may not be qualified for it, remind yourself that you probably are a better fit than you realize.

Then adjust your self-assessment. Remember the study showing that men often apply for jobs when they meet only 60 percent of the qualifications. So ask yourself, “Am I 60 percent qualified for this opportunity?” If the answer is “Yes,” go for it. A man with the exact same qualifications as you probably would.

Fran Hauser

Fran Hauser

Fran Hauser is passionate about leveling the playing field for women. She does this through her investing, writing, and speaking. Fran has invested in over 30 female-founded companies across consumer tech, CPG, media & publishing, and wellness. She is the best-selling author of The Myth of the Nice Girl: Achieving a Career You Love Without Becoming a Person You Hate which has been translated into six languages and was named “Best Business Book of the Year, 2018” by Audible. Fran’s new book, Embrace the Work, Love Your Career is quickly becoming the go-to for women seeking more joy and fulfillment in their career. Fran regularly speaks at conferences and organizations to help women build careers they love while staying true to themselves. Much of her current work is informed by 15 years spent in media, where she rose through the ranks at Time Inc. to President of Digital. She lives outside of NYC with her husband and two sons.

Straight to your inbox.

The best content on the future faces of tech and startups.

"*" indicates required fields

This field is for validation purposes and should be left unchanged.



Join the Angel Sessions

Develop strategic relationships, build skills, and increase your deal flow through our global angel group and investing course.