My High School Bully is Getting Married.

the milestone olympics & making yourself proud

Last weekend, my mom called me from our beach condo.

“You’ll never guess who I ran into.”

It was my high school bully’s mom.

After the obligatory, tight-lipped fake catch-up, her mom dropped the ultimate trump card of suburban success: “Both of my kids are getting married!” She proudly proclaimed.

Not to be outdone, my mom immediately fired back. She quickly let her know that I had recently graduated with an Ivy League MBA and had accepted a consulting job. Take that.

Two mothers standing on a sidewalk, trading credentials.

I laughed when she relayed the story, but the irony of the exchange hit me. It’s exhausting how constantly we try to impress people we don’t even like. We package our lives into these shiny, easily digestible milestones, like a ring, a promotion, a baby, or a degree, just to extract a fleeting moment of validation. Social media has industrialized this process, turning comparison into a spectator sport.

We are all guilty of it. We construct these perfect narratives for public consumption because it is easier to share a polished result than it is to explain the grueling process it took to get there. It feels safer to let a diploma or a job title speak for us than to admit we spent months feeling completely lost.

But whenever you find yourself spiraling into the comparison trap, looking at someone else’s highlight reel, you have to ask yourself one grounding question:

Would I actually trade my entire life for theirs?

Do I want her job? Do I want her husband? Do I want her daily routine? Do I want her anxieties, her responsibilities, and her family dynamics?

Almost always, the answer is no.

We are so quick to covet the shiny thing someone else has, completely forgetting that the shiny thing comes attached to an entire human existence we know nothing about.

Life shouldn’t be measured as a race to see who can check off the most culturally approved boxes the fastest. The problem with the “Milestone Olympics” is that it completely erases the actual reality of living. Nobody talks about the messy middle.

We announce the engagement, not the relationship that almost ended. We celebrate the promotion, not the years of rejection that came before it. We post the acceptance letter, not the applications that came back with “Unfortunately...”

My mom happily weaponized my degree and my new job, but she didn’t mention that I applied to Cornell twice before finally getting in. Or that I collected more than fifty rejection emails before anyone offered me the consulting job.

She didn’t mention the nights I spent staring at my laptop screen, refreshing my inbox just to be met with another automated message thanking me for my time. She didn’t talk about the sheer panic of feeling left behind while my peers seemed to be effortlessly leveling up.

When you are in the thick of it, trying to figure out your next move or navigating a messy career pivot, it is so easy to feel embarrassed. You feel like you are failing because your life does not look like a neat, linear progression. You feel like you’re doing something wrong because you aren’t ready to announce a massive life update on a Tuesday afternoon.

Those details never make it into the story.

We hide the rejections, the pivots, and the jobs that didn’t work out. We curate our lives so heavily that we end up isolating ourselves, convinced we are the only ones struggling behind the scenes. We treat our setbacks as shameful secrets instead of necessary stepping stones. But the truth is, those awkward, unglamorous phases are usually the experiences that shape us most. The messy middle is where you build emotional resilience. It is where you actually figure out who you are, what you value, and what you are willing to fight for.

I am incredibly proud of my achievements, but I am infinitely more proud of the grit it took to get there. I am proud of the girl who swallowed rejection, navigated failure, and survived jobs she absolutely hated until she finally built a life she loved.

I love ambition. I am not an achievement hater. But your goals have to actually belong to you. We need to stop measuring our behind-the-scenes struggles against everyone else’s PR campaigns.

Everyone is on their own timeline. Build the business, go to grad school, get the ring, or move to a new city. But do it for the five-year-old version of yourself; not for the phantom approval of a girl who was mean to you in homeroom ten years ago (thx for this substack inspo tho lol).

There is no competition. YOU ARE the competition.

What is meant for you cannot be taken away, and it certainly can’t be one-upped. Because the people keeping score are usually playing a completely different game.