5 Questions Every 20-Something Asks Themselves

5 Questions Every 20-Something Asks Themselves
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Rachel Tavel

Spring has arrived, and with spring comes another fresh batch of 20-somethings about to enter “the real world” and take their first shaky and awkward steps into adulthood. For some, life appears to follow an effortless and predictable course. But that’s usually not the whole story.

For many new grads, things are about to get weird.

I remember feeling like I had it all when I graduated: the amazing college experience, the best friends, the hunky boyfriend (if you’re out there reading this, you’re welcome) and even the dream job working at Food & Wine and Travel + Leisure magazines in Midtown Manhattan. It was safe, predictable, and maybe even exactly what I expected. But within months of feeling like I had a plan, things began to fall apart and a lot of questions arose. The “dream job” never felt quite right, my best friends were suddenly far away, and then on one particularly heavy summer Sunday, my first love broke my heart just as our train pulled into Grand Central Station.

It was on that July evening, as I sobbed into my pillow heartbroken for the first time that I realized the truth: this was what being 20-something was really going to be like. I recently reflected upon this decade with some friends:

Missy spoke about the anxiety surrounding the “shoulds” of being 20-something: should you stay at your job? Should you follow the path that logically makes sense? Should you do what people assume you’re going to do or should you break away from all expectations and do what feels right in your gut?

Many of us connected over financial concerns in our 20s. Willa, a 20-something currently studying abroad in Amsterdam, asked herself if she is doing enough to support herself in the long-run while acknowledging the difficulty of “letting go” and spending money on adventures without knowing what resources she may need five years from now. Raechel remembered feeling the need to get a job that offered health care and a retirement plan, acknowledging that her parents couldn’t afford to support her. Some, like Mara, stated that she sought independence at any cost. Ben expressed distrust in the economy and the job market leading him to seek stability. Caroline, like many others, remembered a need for external validation during a time when she was just finding herself.

Being 20-something can be a very exciting time. If you’re lucky, it is a decade of great opportunities, unpredictable adventures, and gritty self-discovery. But it can also be a decade of asking some really tough questions and, if you’re brave, doing whatever it takes to find the answers.

Here are 5 questions that (almost) every 20-something asks themselves at some point:

1. What makes me happy?

This is the golden question. It can be exciting, consuming, and totally overwhelming. Ultimately, happiness is what most of us seek. While all decades of life can be a time to pursue happiness, one’s 20s are when we tend to be most selfish, and anything feels possible.

When I took my first job after college working in the magazine industry, I quickly realized that it wasn’t for me. I remember asking myself what made me happy. Every second I sat in my grey cubicle answering phone calls and checking emails, my eyes (and soul) drifted to the glossy photos of exotic beaches and ancient ruins that were expertly captured in the stack of magazines in front of me. I knew I wasn’t supposed to be in an office in Times Square thinking about travel; I was supposed to be out there experiencing the world for myself. I felt like I was faking my life.

So, what exactly did I want? I wasn’t sure. To figure it out, I kept a list. Every day, I wrote down three things that made me happy and three things that didn’t. They could be as simple as “having to rush through Times Square” (blech!) or “the feeling I get the moment my plane lands in a new country” (swoon). I kept track of the topics I enjoyed reading about the most and the parts of my work day that felt the most rewarding. Little by little, my list grew and eventually one thing became clear: I needed to get out of that office, travel and write. So that’s what I did for the next 7 years. Just know that the list changes.

2. Am I falling behind?

As each person finds their way, it slowly becomes apparent that we are all on different tracks. Many of us grew up sticking to the same general path as our friends. Then suddenly everyone’s course changes. Whether you’re concerned with your finances, your love life or your bucket list, it’s easy to question whether or not you are falling behind. But there are a million ways to be 20-something, and the order in which things happen isn’t always what you expect. We don’t all end up in the same place at the same time. Life is unpredictable. Ride yours like a wild bull, not a Segway.

3. Is it too late?


Many 20-somethings feel there is a certain sequence to how life after college is supposed to unfold. But there is no preset order of events we must follow. Remember: you make your own life happen one decision at a time. Love comes and goes (and comes again, I promise). That’s the completely terrifying and exciting part of being 20-something. Whether you’re career-changing or considering leaving a long-term relationship, it’s never too late to go after what (or who) you want. It may be more complicated at times, but it’s your deck of cards to re-shuffle.

I spent 7 years thinking about a career change. Ultimately, I couldn’t deny what was in my gut. My career change from travel writer to doctor of physical therapy was complicated, time consuming, and both financially and emotionally draining, but I’ve always believed it’s better to work hard towards something than just work hard. If something you want takes time you’re not sure you have, remember that time is all you have; invest in it wisely.

4. Will I regret this?

You might, but regret is like a storm cloud: it passes. Whether you’re considering giving up a stable job to work at a start-up across the country or taking out student loans to pursue a less lucrative degree in something your passionate about, there is no way to predict what you will or will not regret. You’ve got to take some risks. And what better decade to do that in than in your 20s? We all want financial security. None of us want to make mistakes. But we all do. Making decisions is part of life, and trust me — those “mistakes” tend to be the best stories. Learn from them, and keep moving forward.

5. Will I regret it if I don’t do this?

Ah, this is the real question. There is a good chance that you will regret what you don’t do more than what you do do. For what it’s worth, I regret nothing — and that comes from a girl who took a lot of risks. So I say go. Say yes. Do it. Try. Ask yourself the tough questions but don’t get too caught up in the answers. Like you, they’re bound to change.

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