For my 28th birthday I held a roast…of myself. 😳
I called each of my closest friends ahead of time and asked them to prepare.
I told them not to hold back, to be as brutally honest (and mean) as possible.
In fact there were certain friends I didn’t call as I knew they wouldn’t be mean enough.

Then I gathered all my friends and had each come up and roast me.
People said “are you crazy, why would you ever do that!?”
I’ve never felt more loved.
There was a recent study that showed contrary to popular belief, friends who playfully insult each other, as long as in jest and fun, are exponentially more loyal and honest.
Ultimately, when friends tease us, it’s demonstrating they know us quite well.
Would you sign up to be roasted for your birthday?
The relationships that make moments like this possible are why I created Outcove.
Table of Contents
What They Actually Said
A few things came up repeatedly. Too many hours at the office. A habit of over-explaining decisions to people who already trust me. The fact that I apparently make the same three jokes in every group setting and act like it’s the first time I’ve told them.
I’m not going to pretend none of it stung. Some of it did. But here’s the thing: none of it was a surprise. I already knew most of it. I’d just never had anyone say it out loud, to my face, in front of everyone I care about.
There’s a difference between knowing something about yourself and having it named. The naming part is what actually changes things.
What I Learned About Myself
Two things surprised me.
First: the stuff that landed hardest was also the stuff that got the biggest laughs. Meaning the people who know you best can see your blind spots clearly and still love you anyway. That’s a rare thing. Worth protecting.
Second: the exercise forced my friends to be honest in a context where honesty was expected and celebrated. Most of the time, the people closest to you are editing themselves to protect your feelings. The roast gave everyone permission to stop.
I got more useful feedback in two hours than I’d gotten in two years of casual dinners.
The bottom line? If you want to know how you’re actually showing up in the world, stop asking people how you’re doing. Give them permission to tell you the truth. Some of them have been waiting.
