The Life Success Skill You Probably Aren’t Developing Enough: Difficult Conversations, Saying No, and Setting Boundaries

“A person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.”

Tim Ferriss

That basically summarizes it but if you care for my half-baked attempt to unpack that quote, press on. Most of us “know” (speaking of, I hate when people say “air quotes” on a podcast) what we need to do but avoid or delay doing so. It’s never fun or easy to have an uncomfortable conversation that needs to happen. What happens when your friends want to walk aimlessly up and down a Sunday street festival reminding themselves of how fun it is every block, and all you want to do is Netflix and chill? What happens when they double-down and ask you why you’re leaving or where you going and you say: home(a seemingly lame reason to ditch your friends)?

The look on their disappointed faces is almost enough for you to crumble and submit to their wishes over yours, but instead you remain strong and chow down on Succession Season 2 and cherish every second of your solitude. This is just a silly micro-example of something you are confronted with multiple times a day, excluding the truly bigger, more difficult conversations like breaking up with someone, quitting your job, etc.

The only things that stand between you and where you want to be are a decision and the necessary conversations. If we lose that simplicity, we are wasting our years away only to look back wondering how we went astray. Take agency over your own life and direction.

“I can’t give you a sure-fire formula for success, but I can give you a formula for failure: try to please everybody all the time.”

Herbert Bayard Swope

A little trick I use is to make a game out of it. Lean into the temporary pain. Similar to how I view taking cold showers/plunges, I welcome and thank it for pulling me closer to where I want to be: a healthier, better version of myself. Each conversation that sucks (when handled appropriately, of course) is one more step toward your truer, more aligned self. Make it your sport. And if still need more motivation, always remember:

“Make your peace with the fact that saying ‘no’ often requires trading popularity for respect.”

Greg McKeown, Essentialism