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Personal Growth

3 Steps For Bridging “The Confidence Gap”

To combat your fear of risk taking, you’re going to need a plan.


In their groundbreaking 2014 article and book “The Confidence Gap” Katty Kay and Claire Shipman outlined the genetic predispositions and environmental factors that contribute to confidence. And, as part of their research, Kay and Shipman found that women take much fewer risks than men, leading to lower confidence levels, which can stifle career growth. 

Building this confidence from scratch (for both men and women) is a difficult endeavor. After all, it is risk-taking behavior, a “try and fail, and try again” mentality, that has been shown to build confidence—which can lead to a frustrating “chicken and egg” problem.

The primary obstacles to risk-taking are the existing patterns that shape our work lives. Tracy Candido, the entrepreneur behind Lady Boss, an NYC-based networking and mentoring organization, admits, “I had reached a wall—I felt tired of going through the cycle of being bold and assertive at work, getting negative feedback, changing my behavior to be more quiet and go-with-the-flow, and then getting negative feedback again.”

The only obstacles to risk-taking are the existing patterns that shape our work lives. 

“I felt stuck in this loop of low self-esteem in my professional relationships,” Candido continued. “Even though I consider myself to be a high-functioning hire, really ambitious, very creative, and also equally rational and logical, friendly and a decent communicator and listener. I started to think, well, maybe it’s not just me?” Candido reached out to other women and found that, in fact, she was not alone.

Below, we’ll explore the steps needed to best overcome your fear of taking the risks needed to advance your career.

1. Clearly Define Your Values & Goals

A crucial first step in the confidence building process is to make a personal road map. This process typically begins with a great deal of introspection. The age-old exercise of asking “Where do you see yourself in five years?” may sound trite, but it’s a good starting point for assessing where you are and where you want to be. What do you want to accomplish this year? This month? By breaking overarching dreams into manageable, actionable tasks, you create a tangible road map.

By breaking overarching dreams into manageable, actionable tasks, you create a tangible road map.

Perhaps you need to further develop your skill set, or maybe you have outgrown your current position. These factors lay the foundation for your daily goals. Resolving to email a new connection, complete an online class module, or research companies that share your values may only take minutes a day, but these actions shake up your existing patterns and their impact compounds over time.

2. Discover Your Risk-Taking Muscles 

Once you have your road map, it’s time to push forward one step at a time. And yes, that means taking risks. Much like a consistent exercise regime, risk-taking is rooted in consistent practice and reduction of the potential obstacles that arise when motivation wanes. Candido believes in the power of incremental and intentional risks. “Personally, as an ambitious woman, I constantly fight the perfectionist in me,” she explains. “I resolve that OCD voice with a principle I’ve learned to live by: create small experiments with radical intent. These are risks and experiments where I’m the one creating the boundaries for success and taking one step at a time to change something on a bigger scale.”

Sometimes, these small experiments appear before you; when that happens, it’s important to reframe these situations as chances to succeed rather than recipes for failure. Jacqueline Twillie, an author and federal contractor from Atlanta, notes, “I’ve started to consider each risk or opportunity as a way for me to expand my skill set and consider how the risk will allow me to reach my long-term goals.”

What is the worst possible outcome of taking the chance: temporary rejection? Mild embarrassment? A chunk of time wasted? If the opportunity intrigues you, don’t count yourself out of the game before you get involved.

It’s important to reframe opportunities as chances to succeed rather than recipes for failure.

On other occasions, you must create these opportunities. Maybe it’s a shot in the dark, like an email to a woman that inspires you, or sending an application to a dream job for which you feel under qualified. The experimentation process is meant to be uncomfortable, because it forces you to acknowledge your fears and push ahead anyway. If you analyze an opportunity and your hang-ups include “I’m afraid,” or “I don’t know,” that’s okay. It means it’s a great time to do it and find out. Because a risk can be as small as an email, you can chip away at your goals and make progress every day. If you’re a fan of data, track this progress. Maybe your tool of choice is an app, like Wonderful Day or Commit. Or perhaps you prefer an analog Don’t Break the Chain calendar. Whatever your tracking mechanism of choice, create a clear visual of the work you put in over time. When motivation flags or something disrupts your momentum, a quick look at all your efforts can help get you back on track.

3. Get Support Through Mentorship

As Harvard’s Kennedy School and Women in Public Policy Program illustrates, connecting with other women can dismantle unproductive patterns. On a broader scale, a greater presence of women, particularly in traditionally male-dominated roles, can also lead to greater acceptance and improved perceptions of women in the field.

Finding a female mentor carves out a safe space to ask questions, explore new ideas, and receive encouragement to step outside of comfort zones. The very presence of women in positions of power can serve as a subconscious confidence boost for their female colleagues, and result in more risky goal-setting. Witnessing other female leaders can help women break down their own stereotypes in regards to their own gender.

Navigating the experimentation process can be lonely, but you don’t have to do it alone.

Jacqueline Twillie asserts, “Levo League is a great place to read articles and watch videos that can help jumpstart your goals. Additionally, its site allows you to ask a mentor a question. If you don’t know what questions to ask yet, read through some of the Q & A from other members and gain inspiration from that.” Mentoring Women Network and Million Women Mentors also provide excellent resource guides. If you’d rather connect in person, websites like Meetup or Eventbrite aggregate local events to fill your calendar.

Professional workshops or conferences can also serve as places to network and connect with other women in your field. Not in a major urban hub but still want to connect face-to-face? Talk to women you admire in your community, regardless of whether or not you’re in the same field. Using the resources available from Lean In Circles, you may decide to gather these women together and start your own group. Picking their brains about their own career paths may spark ideas as to how you can advance in yours.

***

The Roman Stoic philosopher Seneca once said “Luck is what happens when preparation meets opportunity.” Taking risks isn’t about blindly throwing yourself into anything; it’s about doing the leg work beforehand to know what you want, and what you need to do to get it, in order to fully embrace the opportunity when it comes your way.

Meg Duffy

Meg Duffy is a content creator and manager. She has worked as a camp counselor in Turkey, a track coach, an ESL tutor, and a production archivist for the Metropolitan Opera. Meg founded Lady Collective, a project designed to spark conversation with women across the globe, and currently works as Chief of Staff at Hopscotch Technologies

Comments (3)
  • Kelly Magowan

    A fantastic book The Confidence Gap and a terrific article to compliment it and to hopefully inspire more women to to take risks in their careers. Thank you Meg.

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  • Mo

    I am a man and I found this article answers some of my own fears to taking risks, everything starts with yourself. Thanks for a good read 🙂

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  • Catherine Mowbray-Lorenz

    Very well said! I enjoyed this great article and it definitely piqued my interest in the book. One hint I have shared with groups I have trained is to use fear, which is just energy needing to be managed, to propel you forward, rather than root you in place. Use that fear as the energy that it is, to move you forward, conquer that pinnacle, move through that obstacle. You will come out the other side as feeling so much more powerful and confident.

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