Are You at the Hardest Age?

by Allen Gil April 14, 2015

Are You at the Hardest Age?

My favorite teacher, Mrs. Metzger, warned us during senior year of high school that 23 is the scariest age to be. “Trust me,” she warned, “18 might seem like the hardest now, but it pales in comparison to 23.” I doubted her. Eighteen was the SAT, college rejection letters, and the looming conversation with the boyfriend about what form “us” would take when we moved to different states for school – all of which felt monumentally important at the time.

Middle School

And what about 14? As if hormonally-induced insanity wasn’t cruel enough punishment, there’s being dumped into that dog-eat-dog world of adolescents known as middle school. My memory flashed back to having my pants pulled down in front of an entire basketball-court full of teenagers – a ritual that had taken hold at my school.

(As a sidenote, I’m always amazed that Middle School is a thing people actually defend as a good idea….something about how enduring years of verbal abuse and humiliation will eventually result in a stronger, more resilient adult. Who on earth came up with the concept? Like, “Check it out, I have this great idea, bro. Let’s take human beings who are completely insufferable on their own, and – wait for it – group 500 of them together for 8 hours a day with little to no influence from actual adults. I can’t see anything wrong with this plan.”)


Now I’m 10 years past 23. My beloved teacher died last year after losing her battle with ovarian cancer. In a way this feels symbolic of the form “hard” takes once the status of adulthood becomes well entrenched. While a few of us are forced to face the weighty challenges of life during our formative years, my 30’s became the decade of really internalizing the sometimes sobering nature of adult life – lost jobs, children needing surgeries, and the reality that nothing is forever.

But I also see now why Mrs. Metzger was right.

Why 23 is the hardest age

Twenty-three is the age where decision-making starts, where for the first time one’s path isn’t set by someone else. Twenty-three is being pulled from the womb. It’s Purgatory. It’s adolescence all over again, with a little less acne and a little more insecurity.

In past eras, 23 might have looked like a bona fide adult with a job, a purpose, and perhaps a family. Now it’s different. Many young people discover upon graduation that they have no work experience, no marketable skills, and no idea what to do with their lives. College may well have been framed to us not as a place to initiate a career path, but as a place to find one’s self. More journey than destination.

Since I couldn’t decide whether I wanted to be a New York Times columnist, a CEO, or a famous political pundit when I graduated, I decided to settle for deciding what to do next year, and lined up an internship at a large Marketing firm.


The adjustment felt like what I imagine Basic Training for the Marines feels like. After lying on the couch for six months. Suddenly 5 months of annual vacation were replaced with two weeks, and my days felt practically over after being in an office from 8:30 to 5. The corporate world seemed to require learning an entirely new language. Suddenly, I found myself thrust into a world of managing expectations, being strategic and not tactical, delivering value, being proactive and not reactive, and not throwing someone under the bus for something I screwed up.

And then there was the social aspect. I’d never had any trouble making friends, but found it awkward to socialize with people old enough to be my parents. I remember struggling to find common ground when we had the inevitable “How was your weekend” conversation each Monday:

Them: “On Saturday we had Jimmy’s soccer game and then looked at counter-tops at Home Depot. Today I have to leave early for Emma’s orthodontist.”

Me: “Saturday night my boyfriend and his roomates had a kegger. We were there til around 2 a.m. and then just crushed at his apartment. I was hung over Sunday but we worked it off with the IHOP all-you-can-eat pancake special and watched some Friends re-runs.” (Usually this monologue got censored to “Just a relaxing weekend visiting some friends.”)

So 10 years later, what advice would I offer to my former self and others in this life stage of trying to find their way and get established?

Don’t ruminate – start doing. Don’t fall into the trap of spending hours trying to perfect your course of action in support of some grand long-term plan. If you’re not sure what to do, just start doing, and inspiration will find you. Try some different lives on for size – different jobs, different cities, different relationships – until you see what fits. One of my favorite writers, Michael Masterson, calls this the “Ready, Fire, Aim” approach. Don’t think (too much). Do. Then continue or course-correct as needed. Talk to lots of people. Ask lots of questions. Don’t turn down a lunch invitation.

Be humble. I was smart but inexperienced, which is a dangerous combination. I thought my intelligence was a substitute for life experience and wisdom. It wasn’t. Learning takes time and hard work.

Learn to speak Grownup

Move out as soon as you can (and even if you kind of can’t). I know, I know. Financially, it makes no sense to move out of your parents’ house and pay hundreds of dollars in rent when you could live for free under their roof. But it will transform you – and your relationship with them. You’ll feel pride of ownership over your belongings and income and become smarter about them. You’ll appreciate your folks more and fight with them less. You won’t have to answer for where you’ve been and who you’re bringing home – which oddly will result in better decisions, not worse ones.

It gets easier. It really does. You’ll hit your stride. You’ll gain swagger as you start learning and realizing you know a thing or two.

Be patient with yourself, grasshopper.

Allen Gil
Allen Gil


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