Learning to Embrace Mistakes Sucks
Mistakes really suck. There’s no way around it. Recently, I’ve run into my share—small tactical stumbles that sting, not because of any catastrophe, but because I know I could’ve done better. As a fractional leader juggling many priorities, I sometimes try to move too quickly, take on too much personally, or try to muscle through tasks I should delegate. And more often than I care to admit, I’m overly optimistic about what I can get done on projects I probably should have declined, re-scoped, or tackled differently.
Looking back, I know how to course-correct: slow down, delegate to the experts around me, rethink project scopes. But what lingers long after the fixes is the self-doubt. Even with two decades running big marketing teams for some great companies, I find myself wondering, “Was I ever really that good? Am I a fraud? Have I just been riding the coattails of talented teams my whole career?” Imposter syndrome has always been a part of my life, but it's often been background noise. I’m seeing now that mistakes crank it up to an uncomfortable volume when you are the only one in the room.
The hardest part isn’t the external impact. Nearly every time, my clients have been gracious and understanding when these mistakes happen. The real impact is what happens internally. Every small error becomes a mental weight, nagging me as I gear up for the next big strategic challenge. If I can trip up on the basics, how can I trust myself to nail the really critical stuff that’s supposed to be my strength?
As I navigate this new world of fractional leadership, I’m reminded of downhill skiing, another passion of mine. The older I get, the more I think about falling. I don’t bend like I used to when I was 22, but I certainly do break a lot easier. The falls I used to bounce right up from will leave me limping for weeks now. If I am flying down a mountain at 50 miles per hour and worrying about crashing, however, I’m much more likely to catch an edge and actually do it. The same cycle plays out in my work. Obsessing over potential mistakes doesn’t make me less prone to them; it can become self-fulfilling.
At the same time, being fractional means I’m my own quality control. I don’t have a big team behind me to double-check the details. I need to sharpen my diligence without becoming so self-critical that I paralyze myself or lose my joy in the work. So, it’s a conundrum. How do I balance keeping myself safe while maintaining my confidence?
I’m fortunate. I have friends, mentors, and colleagues who hear me out, offer perspective, and challenge me to keep growing. It turns out, they make mistakes too, and misery loves company. I’m learning to gather new tools, lean on my network, and, most importantly, to forgive myself when things don’t go perfectly. I’m working on accepting others’ forgiveness and on celebrating the wins, banking that positive energy so it’s there when I need it most.
The joy of fractional work, much like skiing, is the thrill of speed, the freedom to choose my path, and the new challenges it brings every day. Crashes are inevitable, but they are also how I learn and grow. My goal is not to avoid crashing at all costs, but to become more resilient, more forgiving of myself, and more grateful for the ride.
In the end, making mistakes is part of the journey and learning to love that imperfect, evolving version of myself is perhaps the most important leadership lesson of all.
