The Confidence to be Uncomfortable
What are you doing that scares you?
Always say yes to Miami. The t-shirt in the novelty shop calls out to me. If only it says Always say yes in Miami, I’d buy it without hesitation. Just a few days ago, I said yes to a career opportunity that’s pushing me out of my comfort zone. If I can get positive affirmations in the form of a t-shirt, I’ll take it.
I head another block to the Miami Beach Boardwalk, breathing in deeply the ocean air, feeling grateful that we’re escaping the rainy Bay Area for a while. Lifestyle guru Tim Ferriss and Bob Iger are chatting away in my ears as I turn to a podcast for a dose of self-confidence.
Bob is largely regarded as a titan of transformation and one of the most accomplished CEOs and leaders in the world. It would be easy to look at him and think he had a smooth ride to the top or was destined for greatness, but his book The Ride of a Lifetime: Lessons Learned from 15 Years as CEO of The Walt Disney Company debunks that myth.
Books like these are pure motivation for me. They help me see that people stumble and falter as they pursue lofty goals, so that when my own path gets rocky, I know it’s not unusual.
As Tim and Bob talk about taking risks, Tim asks, “Do you have any quotes that you often think of or try to live your life by?”
Bob shares this from Teddy Roosevelt:
It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again... who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly.
Since my transition away from clinical medicine over 20 years ago, my career has been a series of daring greatly. Taking leaps into endeavors filled with uncertainties. What I’ve learned is that the right opportunity has to be about three-quarters “I will kick ass at this” and one quarter “yikes, this scares me, but I can figure it out,” then using gut instinct to ask “does this feel right?”
Not every opportunity is a win. Some—like starting Best Friend Jack—have been more successful than I ever imagined. Others—like when I worked with someone who was a toxic gaslighter—were filled with gut-wrenching lessons learned. I always hope for the former, but know that the latter also keeps me grounded and growing.
Ginni Rometty, the former chairperson and CEO of IBM, posted earlier this week, saying, “Identifying and pursuing your own North Star is critical — be it careers, family, volunteering, health, or whatever gives you a sense of purpose…It will be uncomfortable at times, but I’ve always believed growth and comfort never coexist…I wish all of you the confidence to be uncomfortable in the year to come.”
So get out there.
Have the confidence to be uncomfortable.
Find your right mix of “I will kick ass” and “this scares me but I’ll figure it out.”
I’m rooting for you.


