#SMALLBIZCEO WEEKLY UPDATE #4: “Do It Afraid” (10/27/23)

Co-Founder of Mindset To Money, Thomas K.R. Stovall here. On my mind for this week’s behind the red curtain update for Mindset To Money is “Do It Afraid.”

If you’ve got it all figured out, you’re not afraid of anything, everything is smooth sailing in every area of your life, you can skip this email.

But if sometimes you’re scared, sometimes you wonder if you’re going about things the “right” way, or if you feel called to do big things but scared out of your mind as you walk forward on that path, you might find value in this one.

Lesson 1: I don’t try to avoid “failure,” I lean into it and run towards it…

  • Leaders are willing to stand on the skinny branches, and sometimes they break…
  • I’m always willing to press beyond my boundaries into spaces unknown, because that’s where the biggest growth in life happens
  • When we’re unsure, when we don’t know what to expect, when we can’t predict the outcome, this is when we LEARN, and when our spidey senses come alive and we soak up new information and correlate it to what we know and have experienced from the past
  • What I’ve learned is that failure as a general state doesn’t exist. It’s not real. There is only “failure to meet a goal you set.” Inside of that frame of reference, we simply have a performance context, where I can say “what was missing this time that if I add that to the mix, I can close that gap between the outcome I produced, and the outcome I intended to produce?
  • Because I have that context, I don’t relate to myself as a “failure” when I “fail to meet a goal” that I set. I can simply focus on testing, and testing, and testing, and iterating, and iterating, and iterating based on what I learn from those tests
  • Business, relationships, investing, it’s all just one big test environment. Some tests will work, others won’t. The real end game is WHAT DID I HAVE THE OPPORTUNITY TO LEARN?
  • The biggest and fastest new learnings for me happen when I am pressing myself into environments unknown, that absolutely could result in me missing my mark, so I do it again, and again, and again, no matter how scared I am

Lesson 2: Imposter Syndrome hasn’t gone away for me…

  • And I realize now more than ever that it probably never will
  • There will always be rooms that I’m in, where I feel like the least qualified person present
  • This feeling is amplified when I’m the one who’s on the stage, and all eyes are on me to deliver value
  • All I can do is be authentic to me, and know that I’ve been invited into that room because of who I am, how I am, and what I do, and I can either own that, or argue with myself to believe in my limitations
  • Yesterday, I stood in front of 30 senior executives from companies all around the globe, who flew into Chicago for 2 full weeks to participate in Northwestern Kellogg’s flagship Executive Development Program for senior executives
  • Representing the Philippines, Macedonia, the UK, Asia, Italy, of course the United States and many more countries, these executives each run large organizations with anywhere from hundreds to thousands of people who they are directly responsible for leading
  • My job as the facilitator in that room? To deliver one of my proprietary 90-minute think tanks of my own design, on how to create a culture of “Leaders Creating Leaders” inside their organizations
  • If there was ever a room of brilliant senior leaders, who could easily take a glance at me and wonder “What does this guy have to teach ME about how to leading and creating other leaders in my 9-figure organization?” this was that room
  • So I felt the fear, thanked it for sharing, and then handled my business

Lesson 3: No one remembers the most average burger they’ve ever had…

  • The more accomplished and higher level the person is who you are talking to, the more autonomy they have, and the more sensitive they generally are to their time, as it’s their most important asset
  • They’ve also seen and heard A LOT, so many of them “listen fast,” and look to quickly identify what they think are correlations to other things they’ve heard or seen, so they can decide whether or not to prioritize or deprioritize the information coming at them in any moment
  • I could have given a “safe” presentation that everyone in the room agreed with and felt good about, and that would have been fine
  • But I don’t live in the world of doing things that are “fine.” My foundational frame for how I approach my life is “Live Are on The Line.” Every conversation, every moment, is meaningful
  • If you give me 90-minutes of your time, I intend for you to get a foundational TRANSFORMATION of some sort, if I have anything to do with it
  • But doing that requires not just skill, but a willingness to embrace the risk that this thing might not work, and people might not like it, because transformation is uncomfortable, and it can certainly be messy
  • So with my think tank, knowing what I’d be up against, I chose to give those executives one of the most visceral experiences they’ve ever had, transforming our 90-minutes in that room into an interactive environment with time-constraints, changes to their teams and disorder that mirrored the workplace
  • I embedded unconscious triggers throughout the think tank that created a visceral experience for the room, with the intention that they revert to their base human nature, pulling out their apathy, their indifference, their willingness to take their ball and go home when they don’t get their way…I even had one team get so mad that they got up and left the room!

Then I pulled the rug out from under them, and let them know that they’d been played…

  • I broke the news to them that every single thing they’d experienced over the course of the think tank was to pull out their base human nature, their wiring that activates when they’re triggered
  • It didn’t matter what their title was, how much money they made, how big their organizations were, or how much they already “knew” all the leadership principles that we started off the day discussing…
  • When they got triggered, when they weren’t listened to, when it was made clear that their thoughts and input weren’t being listened to or heard, it took no time for some of them to become apathetic, indifferent, withdrawn, and in some cases, to quite literally QUIT the exercise
  • At that point, I let them in on the secret…
  • This is exactly how some of your employees feel…disregarded, unimportant, incensed that they have to show up day after day and not have a space to feel safe, where they are seen and heard and acknowledged, and FEEL like they are part of something…
  • And even more, this is how your leadership shows up. When you’re pressed, when there are deadlines, budget cuts, constraints…when you’re PRESSED and your baseline human wiring gets triggered, go ahead and take out the mirror and look at how you responded today….this is you
  • No judgment – but this is you. Take it in. Don’t believe for a second that you only acted like this because it was an exercise in this room. If you’ll do it here, chances are you’re ALREADY doing it in the high stakes environments that present themselves in your organizations…
  • The question then became does how you’re showing up as a leader ALIGN with your goals of having leaders who create leaders showing up in your organization?
  • Are YOU the inspiring example of a leader who you want to see emerging in your organization
  • For the next 15 minutes, those senior leaders came to the microphone, and shared the deep dive insights they got experientially, from the exercise, and how they planned to take what they learned to create safe space for their teams to be listened to, and seen, because they could FEEL the consequence of not doing so
  • They shared how this session was unlike anything they’d ever experienced, and that they would never forget it
  • The folks from Northwestern Kellogg who invited me to lead the session had never sat through one of my think tanks, and they were at the back of the room, VISIBLY nervous
  • What I delivered is not what is done in the world of academia, for a group of global executives, who have paid tens of thousands of dollars and uprooted their lives to spend 2-weeks in Chicago for a professional development program
  • This is not what any of them expected, but it’s what I was committed to giving. Not a “good” presentation, a TRANSFORMATION
  • I got amazing feedback in the room from participants, ESPECIALLY those who initially had walked out on the exercise before they realized that they’d played right into what the exercise was designed to illicit from them
  • Maybe those rave reviews show up in my formal written feedback reviews Kellogg, or maybe I find out that the written feedback from participants doesn’t match the wonderful verbal feedback I got from them in the room
  • None of that is in my control. What I do know is I delivered an exercise that for a number of people in that room, was transformative in how they view their organizations, and what actions they’ll take to support their people from this point forward
  • Whether or not I ever get invited to speak in another Kellogg room, my focal point in choosing my thoughts, words and actions will always be focused on staying true to my northstar, and not rooted in the fear of judgment or “losing an opportunity” that is also a natural way to feel
  • Why? Because LIVES ARE ON THE LINE, and that matters more to me than my fear of failing (to meet a goal I set)

At Your Service,


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