What It Really Takes To Build Your Professional Confidence

Today marks the 100th issue of the Strategic Leader's Toolbox (Subscribe Here)! 🎉
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At the same time, my daughter is preparing to celebrate the 100th day of school in her first grade classroom. We got a notice in her homework folder this week inviting each student to bring in a jar of 100 somethings—anything they choose.
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It's quite a thing to look at 100 of something and consider what it means. It reminds me of an excerpt from poet David Whyte's book, Crossing the Unknown Sea: Work as a Pilgrimage of Identity:

"Not long ago, I heard on the radio a description of a new form of propulsion for a probe that had just been launched into deep space. The spacecraft was powered by a newly developed ion motor, where sub atomic particles were propelled out the back of the probe and provided its acceleration. The scientist describing the new motor said that the amazing thing about the motor was that although the electrons were pushed out of the back of the probe at an incredible speed, the electrons were so small that the acceleration of the craft was actually only the equivalent of the weight of a piece of paper. But because that slight weight acted every moment and it occurred in a basically friction-free environment, the craft could reach speeds of hundreds of thousand of miles per hour.
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"It's a profound metaphor for a poet, of course: just the weight of a piece of paper...But it is a metaphor for any work and any person. A steadily building field of activity, laid down almost imperceptibly, layer upon layer, which creates a world and at the same time prepares us for our appearance in that world."

- David Whyte

When I started the Strategic Leader's Toolbox, it was a roundup of articles, podcasts, and other resources that I beamed out to help you develop your career and leadership.
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About a year and a half in, I realized that I while the resources I shared were valuable, they were also a sort of armor that I hid behind: curating other people's ideas spared me the vulnerability of articulating my own.
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It was then that I flipped the format—challenging myself to write original articles with my take on professional topics and produce shareable tools for you to apply those ideas to your own unique situation.
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​Through it all, my goal has been: build trust and credibility with my audience by sharing valuable content.
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What I didn't realize was: I have also been steadily building trust with myself. ​
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I remember the Bambi-legs feeling of sending out the first issue. I remember longing to feel confident and sure of myself. Like most people, I wanted to skip to the part where I felt like I was coming to my work with a strong backbone and a full, certain heart.
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I heard somewhere that there is an equation for confidence:

Confidence = Time + Experience

Like Whyte's piece of paper metaphor, there is no shortcut or blast to get there—instead, it's about steadily building the work, one piece of paper at a time, until one day you look and it's a solid stack with heft and weight.
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I can point to it now and say: I've built a track record with my audience, but I've also built a track record with myself.
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Here's what I've realized about professional confidence:
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​1) There is an element missing from the equation.
​I propose a change:

Confidence = (Time + Experience) + Permission

In order to build that track record, you first need to grant yourself the permission (sometimes over and over again) to do things differently, to put yourself out there, to step into the discomfort of building something new or showing up in a new way. ​
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I've found it handy to actually write myself a permission slip whenever I need one. ✅ I created one for you to grant yourself the permission you need here.
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​2) There are two types of confidence.
​Often, when we think about confidence, we think of certainty that things will turn out well. "I feel confident in this presentation." That type of confidence has felt elusive to me for a long time. I've been puzzled about how to access it.
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When I first started Penney Leadership, I had the opportunity to facilitate a leadership training series for 40 mid-level leaders at a community health organization. The night before the training, I was FREAKING OUT because I was not certain of the outcome. I worried that I didn't know my stuff. I worried that they would take one look at me and say, "This kid is here to tell ME how to be a leader?" I was not at all confident that it would turn out well.
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But I showed up and led the training. I pushed through the scary, vulnerable parts of being up in front of a group of people, I tried to get out of my own way and be myself, and I focused on their questions and the tools I had to share with them. On the ride home at the end of the day, I realized: it had gone okay.
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A month later, the night before the second training in the series, when I started freaking out, I was able to remind myself: last time you showed up and it turned out alright. Maybe this will be the same.
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And eight months later, when I traveled to New York City to lead a day-long leadership training for Harvard Business' Corporate Learning programs, instead of shaking in my boots I reminded myself again: you've done this before and it turned out alright.
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It's like building a muscle—each time it's a tiny bit easier to talk myself through it.
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​There is a difference between confidence in the outcome versus confidence in the process. I am never certain about the outcome when I put myself out there through my work. But I am confident in the process of showing up, talking myself through my track record, and using the tools in my toolbox in service of others' professional development.
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I can now confidently say, after 100 issues of the Strategic Leader's Toolbox, that I've amassed resources that I refer back to all the time, that give others direction and guidance for some of the key questions that challenge us along our career and leadership journeys, and that I've added my own voice to the conversation.

When I sit down to write an issue, I remind myself of my track record (time + experience) and give myself permission all over again to fill the blank page.

Your Next Steps:

➡️ Look at your track record of work. What comes up when you consider the time + experience you've amassed on your way to where you are?

➡️ Write yourself a permission slip to step out in a new way.

➡️ Notice the difference between confidence in the outcome and confidence in the process. How can you pay more attention to the latter?