As an investor, founder, CEO and business book author, I write about startups, design, how to build a good business, and I like to muse about culture in any form.

Why the most successful people are also–at times–the most uncomfortable


I interviewed an early-career person who told me a story about the experience of telling his father that he was not applying to law school. The dad had long expressed this specific ambition for his son, who had gone along with the plan. As the young man gained more and more experience in college and life, the idea of becoming a lawyer held less and less appeal–it became positively repellent. So he swallowed his fear and anxiety about the conversation with his much beloved dad, and got it over with. The dad loves his son and quickly embraced a new “plan.” Fast forward to today and the young man, Manny Henriquez, got a Masters in Management and recently joined The Grommet.

During a discussion of facing fears as a path to making hard decisions or sticking with challenges, a wise woman said to me, “It’s not enough to face fear. You also have to expect and embrace the discomfort on the other side of walking through a fear. I see too many people who can’t deal with change or challenge because they are addicted to being comfortable. They think that a good decision is always a comfortable one. Nothing could be further from the truth.”

The time to master the experience of being uncomfortable is to do it as early and often as possible.

I pushed a lot of boundaries as a kid but I really started “practicing” at age 14. How? By sending myself to boarding school.

I’ve done many, many other things that look harder than living in a dorm for attending prep school. Moving to France right after college. Childbirth without anesthesia. Leaving well-paying jobs when I had nothing lined up, and no meaningful bank account. Moving my family to Ireland with no job or safety net. Starting a company. Turning down a possible Grommet acquisition during a starvation period because it would have hurt our investors. Unwinding a marriage. Dramatic house and condo renovations. Negotiating complex international deals. Firing people I like and respect.

I am not superhuman or fearless. I have just learned the habit of facing discomfort and even embracing it. When the going gets tough or frightening, I always remember my feelings as a skinny, scared scholarship student who wanted to throw up every day. That kid was often awkward and uncomfortable, but she graduated with honors. To this day, going to prep school was the hardest thing I have ever done.

I’ve learned that when my stomach is roiling, this is my body telling me that I am doing the right thing. I am living on the edge I need to reach the next goal or level.

Being able to do this has no age limit. Middle aged people can be paralyzed by fear of discomfort just as easily as young people facing hard things for the first time. But the young person who starts developing the navigational skills and self-awareness for mastering fear and discomfort will build the life they really want, with no regrets to hold them back.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

Basic HTML is allowed. Your email address will not be published.

Subscribe to this comment feed via RSS

%d bloggers like this: