There’s More Than One Way To Be Successful In Your Twenties

My Listless Birthday

Last week was my birthday. I turned 29 — devoid of crisis, catharsis, and crippling anxiety. I did not plan for weeks what I would do or not do. A couple days prior, I decided to that I wanted my husband to make fish and turnips and pick up a Willamette Valley pinot noir. We ate the leftover cake from birthday party the prior Saturday. I then treated myself to American Horror Story on FX.

That was it. Same Caroline Gould time, same Caroline Gould place.

I wrote my college essay on Holden Caulfield. My intent was to contrast myself to The Catcher in the Rye’s static protagonist and show myself, though I loved the novel, as his opposite (a dynamic, evolving character) and imply that that was to be celebrated — and thus rewarded — with admission to all fourteen colleges to which I applied.

Eleven bit and three told me to pound sand. (who needs you anyway Harvard, University of Virginia, and Air Force Academy?) At 29, I look back on the essay a little differently than when I wrote it at 16. Today, thanks to the internet, we are bombarded more than ever with “shoulds.” There is literally an unfortunately viral list for every year of one’s life covering what one “should” have accomplished and what one “should” be doing and not doing for every area of life from romance, to career, to family, to investing, to hobbies, to ordering at a bar.

Well, fuck that. “Shoulding” is shaming.

At 16, I thought Holden was a grump. My brother, after I first read the book in middle school and explained to him what it was about, opened the back cover and drew an unhappy face, under which he wrote in his third-grade hand, “Holden.” Holden was exactly where he needed to be, unhappy face and all. He was simultaneously grieving a devastating and untimely familial death and shoved into forced isolated coping after being molested.

No kidding he was an unhappy face. Years later, I am sure these problems would continue to haunt Holden, but if he were a millennial, he’d be taunted with list-ical reminders about “Why Nothing Will Ever Top His Early Twenties” or “What He NEEDS to do Know about Personal Finance NOW.”

He kind of had some other stuff going on.

As much as the internet brings new outlooks into our world, I think it has also sought to homogenize the millennial experience. We are continually shown here is what it should look like and if it doesn’t you are wrong or bad. Or, better yet, here is our eBook on how to fix it—just join our mailing list to get yours INSTANTLY!

I look at my own disjointed, nonlinear experience of adulthood. At 26, I was a Director at a internationally-renown architecture and interior design firm earning in the top 1% of people in my age group, check one for adulting well… on the surface.

I had a master’s degree… check again.

I had an ample 401k, check again.

I was saddled with credit card debt and spend my first months in Philadelphia at my fancy new job renting a tiny room in a bad neighborhood, consigning a lot of my clothes, taking online surveys for extra cash, eating ramen a lot of nights, and selling my car to pay bills in order to catch up. Record scratch… what?

Why? Uh-oh these behaviors were definitely not on the latest “15 Things Every Successful Women in Her Mid-Twenties Should Be Doing.” Yeah…and I felt like shit for it. There I was supposed to be owning the perfect black blazer and “statement bag” when I just sold mine and living in my first “adult apartment” when I was in the most cramped quarters I’d ever rented.

Prior to heading to Philadelphia, I was living in Washington, D.C. in a gorgeous townhouse (check adult win again!), I had rented the beautiful space because my then boyfriend and I were on the verge of engagement (check adult win again!), but then we broke up (wait, maybe that was naivety, not adulting? Let me refer to the latest list…). This left me with the lease I couldn’t get out of for another year and a major drain on my liquidity as I shouldered the rent myself. Yet, I was determined to make it work to prove I was “an adult.”

To who, though?

My husband is thirty and does not have a college degree. Sixteen-year-old me writing my Holden Caulfield essay in my Abercrombie mini skirt and Ugg boots (*shudder*, virtual cone of shame applied) would have certainly agreed with any internet list that a lack of a bachelor’s degree made someone less of an adult and less worthy.

After escaping Hurricane Katrina, my husband dropped out of Penn to tour with his band and was supporting himself fully for years, traveling to various cities while I was flitting around my college campus in coordinated pink Burberry rain boots, pashmina, earmuffs, and umbrella (*harder shudder*). Show me the internet list of “shoulds” that honors a truly formative, mature adult experience like his. I don’t think you’ll find one.

We let our “shoulds” and these lists written from one person’s perspective hijack our self-worth and confidence and if not that far, at least make us second guess for a moment. Why do we celebrate this narrow-mindedness with likes and shares? I am saying the genre wouldn’t be so popular if it didn’t have a (deluded) following.

At 29, I see why Harvard, the University of Virginia, and Air Force Academy called B.S. on my college essay (and quite possibly my score on the math portion of the SAT too). It is not up to one person and one voice to preside over where we should be in life at a given juncture or what we should be feeling or thinking. You never know someone’s complete story, circumstances, plan, past wounds, and aspirations. And my GOD, no one should be telling you what to order at a bar or have in your fridge. Those are personal, intimate choices.

The only way in which we “should” be living by is the way that is in alignment with our passions (what we like to do), our talents (what we’re good at) and our values (what is important to us)…or at least doing the best we can to do so.

Now, put this song on and give yourself a hug. You are doing the best you can. Happy Birthday, Happy Today, Happy Every Day.

Email this to a friend


Caroline Gould is a personal branding expert and career consultant based in Washington, D.C. Her signature program is called Self Discovery School. She also writes a weekly advice column on Post Grad Problems. Submit your question or find out more on

20 Comments You must log in to comment, or create an account

Show Comments

For More Photos and Content

Latest podcasts

Download Our App

Take PGP with you. Get

New Stories

Load More