Grad to the Future: What We Wish We’d Known On Graduation Day

Roadtrip Nation
5 min readMay 28, 2019

Everyone wishes they could go back in time and give their past selves some advice from time to time. “Don’t send that text. Just go for it and move to New York City already! ‘Grad to the Future’ is a horrible, terrible pun and you should absolutely not make it the title of your blog post!!!”

This feeling seems to apply tenfold at the big pivot points in our lives—around this time of year, it’s probably most commonly being felt by high school and college students as they prepare for graduation.

But while we hold our collective breath waiting for someone to invent that time-traveling Delorean, there *is* a reasonable, semi-easy way for any upcoming or recent grads to proactively avoid major regrets or meltdowns…

Here at Roadtrip Nation, we operate around one principle: If you encounter something you don’t know how to navigate—be it applying to college ,writing a cover letter, or just taking your first steps after graduation—all you have to do is get out there, find someone who’s been through it, and talk to them!

Since we’ve been meaning to introduce you to some of the awesome staff working hard behind the scenes here at Roadtrip Nation HQ, and since all of us have some experience with high school and college graduation days, we decided to go meta, open up the Roadtrip Nation yearbook, and get our coworkers’ advice!

By giving you the wisdom we desperately wish we could give our past selves, we hope we can help all you grads feel confident about your futures.

Q: What do you wish you’d known on high school graduation day/ as you were heading into college?

“Say YES to every new opportunity presented to you. You will be doing yourself a disservice if you don’t at least TRY a new club, team, class, etc.

Nicole: Most Likely to Be Wearing Your New Favorite Outfit

And if you end up not enjoying it, you never have to do it again! But at least you tried, and you never know what you might end up enjoying that you didn’t expect.

And PLEASE don’t tie your identity into your academic performance. Always try your best, but if you don’t get the grade you hoped for on a paper or exam, I PROMISE that you will still have a successful and fulfilling life. Don’t be so hard on yourself!” —Nicole, partnerships program manager

Elizabeth: Most Likely to Be Twinning With Nicole

“Sauce pans in summer, crêpe pans in fall—when winter’s upon us, there’s food for us all.” —Anonymous, ???

“Sleep isn’t a nice-to-have; it’s a necessity for college survival.” — Elizabeth, visual designer

“Don’t be afraid to go for it and take risks.” —Kyle, editor

“Don’t pretend that you are small.” — Evelyn, senior software engineer

Q: What do you wish you’d known on college graduation day, as you were heading into the “real world?”

“Enjoy the summer and don’t rush to start working. (I started working a full-time job the week after I graduated college!)” —Jeanette, controller

Marissa: Most Likely to Have A Celebrity Encounter With Jeff Goldblum

“You worked hard to get here, and you’ll work hard to get other places in life. Along the way, don’t lose sight of the things that make you happy. Even if that thing is dinosaurs!” —Marissa, education programs coordinator

“You’re not doomed if your first job out of college is at a smoothie joint or in an entry-level position. Everyone has to pay the bills. Everyone has to pay their dues. Starting at the bottom doesn’t mean that you’re a failure, that you’ll never “make it,” or that you’re “wasting your degree” — it means you’re going to have to earn what you think you deserve, and there’s nothing unfair or strange about that.

Work hard no matter what, and don’t put your goals and dreams on the back-burner… make room for them on the side-burner, or else you might as well kiss them goodbye.” — Chelsea, director

“No matter how awesome you are or how hard you worked in college, the perfect job isn’t going to just magically land in your lap—you’ve got to put yourself out there! So go apply to anything and everything that interests you!” —Allyson, copywriter

Nathan: Most Likely to *Not* Take His Own Advice

“Never look back. You’re not going that way. ;)” — Nathan, senior editor

“There’s no perfect answer. You have to try something and make choices based on what you’ve learned.” — Alexis, manager, project management office

“Don’t compare your job (or lack of a job) to any of your peers’. Everyone is starting down a different path, and none of you know where you’re going to end up!” — Tim, senior director of business development

This is just a little teeny-tiny taste of the kind of advice you can easily get by reaching out to the grads around you who’ve been through it! It can get silly or it can be serious, but there’s almost always some kernel of truth that you can use moving past that graduation stage and onto your next stage of life.

For more in-depth advice to help you tackle the big stuff coming up in your life, you can also check out our New York Times bestselling book Roadmap: The Get-It-Together Guide for Figuring Out What to Do with Your Life. (A great gift for recent grads, if we do say ourselves!)

Roadtrip Nation is an organization dedicated to helping individuals find fulfillment by turning the things they like into careers they’ll love. To learn more, check us out at



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