Leadership Lesson: How Success Changes the Rules of the Game

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Here’s this week’s message: It’s this tricky thing. It doesn’t always look like failure; sometimes it looks like playing it safe. Self-sabotage. That sneaky little voice that shows up right when you’re about to stretch, grow, or even thinking about that first step into something new. It whispers, “You’re not ready yet.” It tells you, “This isn’t the right time.” Or it convinces you it’s endless preparation, and not seeing positive traction or action; or doubting ourselves so much that we never even try. It’s a similar topic I wrote about with the ‘cheese’ metaphor in a

. Yet for some reason(s), over the past couple of months, the subject has come up a few times in conversations within my familial village, other times while coaching/mentoring, and truthfully, with myself – through reflection, listening, observing. Those quiet moments of introspection…

Self-sabotage seems to be one of those “recurring” themes as “adults” (I’m referring to the young/wise adults, not so much the high/low functioning adolescent-type adults)- we all go through these stages of adult development. Growth happens, as we grow/heal. And we typically go through some form of kind of change/transition as events and circumstances warrant. Here’s the thing: self-sabotage isn’t always dramatic. Sometimes it’s as subtle as procrastination. Other times it’s over-preparing, second-guessing, or letting fear masquerade as “cautiousness.”

Like me, you’ve probably interacted with people who are bright, gifted, creative, and talented folks - talk themselves out of opportunities that could change their lives. And yes, I’ve done it too. The meeting I didn’t speak up in *especially early on in my career), but now I use it as a skill – those times to speak up and “pick & choose my battles”. Or the proposal I read about but delayed in writing it and the deadline passed. The leadership role I almost didn’t apply for. Each of those moments was less about lack of ability and more about me getting in my own way. Sound familiar? That’s the comfort zone calling. And if we’re not careful, we’ll answer it every time. That’s when we become like a “Gregory”, from Abbott Elementary.

During a recent chat I had about self-sabotage I shared a personal story from an encounter in my 30s. I remember this lesson vividly. Back then, I was still figuring out what kind of ‘leader’ did I want to be, and would soon be knocking at 40, (and premenopausal) what kind of woman I wanted to be. I was ambitious, yes, but I was also scared - scared of putting myself out there, of being seen, of what would happen if I actually got the thing I was chasing.

On this particular day, a wisdom nugget was dropped when they looked me straight in my eyes and said: “Some people are just afraid of success, Pat.” What? Afraid of success? Wasn’t success supposed to be the goal? But with time, I realized they were right. Success is more than a shiny prize at the finish line. Success changes the rules of the game. It stretches you, raises expectations, and makes you responsible for more than just yourself. It calls you to lead boldly—and that can feel heavy if you don’t believe you’re ready. That feeling of “heaviness” – it's like something that still keeps ‘gnawing’ at you- that is, if you stop to pay attention.

And here’s some truth: many of us are more comfortable with failure than success. Failure is predictable. Failure keeps us in familiar territory. Success? Success asks us to grow, to be visible, accountable, to hold space for others. To lift others up. That’s where the fear creeps in - and that’s when self-sabotage shows up. But let me share this: staying small doesn’t serve you, and it doesn’t serve the people watching you. Every time you talk yourself out of stepping forward, you rob the world of your gift. So how do we move past it?

• Call it what it is. Don’t dress up procrastination or perfectionism as caution. Name it: self-sabotage. Give ‘it’ a name. In my collection of works an 80’s classic book, called “Taming Your Gremlin” by Rick Carson. Your ‘gremlin’ according to Carson, represents that narrative in your head that has influenced you since you came into the world. As the author suggested, I gave my gremlin a name, my saboteur’s name: “Claudia”. Step back Claudia!

• Remember who you are, and for the believers, do not forget “whose” you are. Fear wants you to forget your power. Write down or keep a journal about your wins. You have probably made a leap or two before – remember what that win felt like? Speak your affirmations. Post them, if you need too. Borrow that kind of strength from your past successes.

• Shift the frame. Instead of “What if I fail?” try “What if I succeed? Success demands bravery. Surround yourself with brave people, not the ones that will feed or fuel your gremlin.

• Take one brave step. Even a small action is an act of defiance against fear. Courage grows in motion along with what, if any, role spirituality plays in your life. Fear creates boundaries. What brave first or next step can you take to push beyond the boundaries fear can create?

And one final truth: success isn’t a burden, it’s a calling. As servant leaders, it’s not something to shy away from - it’s something to embrace, nurture, and multiply for the sake of others. So, the next time you hear that little voice urging you to turn back, remind yourself of this life lesson: fear of success is real, but it doesn’t have to rule you. Step forward. For someone you may not even know, your representation is everything. That’s what I am doing right now. More to come on that later. Because for many of us, as we age, that ‘calling’ just doesn’t stop.

Weekly wisdom, in their own words:

“Being in process is an attitude – an appreciation of this simple truth and the reality that your life will be forever unfolding and your future always unknown.”

- Rick Carson (b. 1944)