5 Questions To Ask Yourself In Your 20s

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As I was sitting on the subway after work, a song started playing through my headphones that reminded me of my 24-year-old self, fresh in NYC just five years ago.

Everybody here wanted something more, searching for a sound they never heard before. I said Welcome to New York -  it’s been waiting for you. Taylor Swift’s pop magic flowed through my earbuds. I was instantly brought back to walking down Broadway, looking up at the Freedom Tower, trying not to look like a tourist, full of excitement and hope at all the glory that my 20s could be.

Flash forward 5 years. 

I’m teetering on 30-years old and wondering: where did all the time go? Am I any different than I was five years ago? Your 20s can feel like a bright flash and unending death at the same time. Sure, your teen and youth years are when you physically become an adult, but your 20s are when you mentally grow into an adult. Your frontal lobe, the part of your brain where decisions are made and rational thinking occurs, is not even fully developed until you’re 25. Your 20s are the decade when you grow up.

So, as I was sitting on the train listening to TSwift, I was caught in a wave of reflection. On the surface, 29 means I am a wiser, surer, thicker, more jaded, tired and tattooed version of myself. I’ve traveled the world. I’ve been on hundreds (literally) of dates in the Big City. I’ve been through two earth-shattering breakups. I’ve changed jobs. I’ve made many new friends, mentors, and acquaintances, and lost a few too. But what does all this growth measure up to? What does the journey of becoming look like? How did I get here?

Through all this living, I’ve learned a lot of harsh, beautiful, and surprising things about myself. With the living comes the learning -- and the way to learning is through reflection. In your 20s, life can feel like a skydive: terrifying, fast, and pee-your-pants exiting. But as one of the most life-altering decades of our lives, it’s important to reflect on a regular basis. 

Here are some questions I ask myself to reflect on growth, choices, and who I ultimately want to become:  

  1. What are my values? This is something you should ask yourself at least once a year. Your values could be anything from Community to Fun to Honesty. How do your values play out in real life? If you value Community, you may intentionally build relationships and associate yourself with groups to connect and belong. If you value Fun then maybe you spend a few extra bucks each month on going out because that’s something that’s important to you. Check in with yourself and be brutally honest; you may think something is going to be fun or enjoyable in theory, but in reality, if the action is not in alignment with the value, then it could be time to change up your routine. What was fun in college may be kinda lame to you now. Take a few minutes and write down the guiding values of your life. Throughout your 20s these will probably change a lot -- and it’s an interesting exercise to map your growth through your values. 

  2. What do I need to “undo”? It’s important in your 20s to identify the things in your childhood or what you were taught as a young person (by the world, your parents, friends, school, media, etc) that may be negatively coloring the way you are in the world. Even if you had an amazing, cookie-baking, sunshine-filled childhood, there are always things you need to rethink based on who you want to become. For me, approaching 30 and being single has meant questioning everything that was ingrained in me as a kid, especially around partnership. I was taught explicitly and implicitly that being married was when your life began, rather than your life belonging to you in the first place. This is something that I work at every day -- to not hold my breath waiting for a dude to come in and change my life for the better. My life is good, with or without Prince Charming. 

  3. What can I do now to make my life better in 5 years? This question can be interpreted in many ways. It can be interpreted quite literally -- that saving more money and paying off your student loans can put you in a better place in 5 years. It can also be interpreted in more abstract ways. For example, in your 20s you might consider straying away from people who are dishonest or make you feel bad about yourself. That is something that will make your life happier and fuller in the next five years. Consider the ripple effects of your life today on your future self. 

  4. Would I take anything back? If the answer to this question is yes you have regrets, then reflect on those decisions. Make choices moving forward to avoid a problem before you make the same mistake twice. As the cliche goes, we can’t redo the past, but we can sure as hell make the future better. Whether your regrets include something as simple as texting your ex or as drastic as taking a job you hate, use these lessons and learn from them. That is power.

  5. Would my 15-year old self like my adult self? I think about this all the time, and it's a hard question to answer. Think about yourself at 15. What did you imagine your “adult” life to be? I envisioned leading the glamorous life of Carrie Bradshaw, filled with shopping, writing, dating, and NYC. Although THAT is not anyone’s reality, even my own, I still feel like I embody the spirit of confidence and adventure that Carrie represented. The older I get, the more I need to keep reminding myself of a mantra I had in my teenage years based on Glennon Doyle’s first book. Be kind, be brave, be grateful. Every day is a battle to be my best self. And, every day is a chance to prove to myself that I should be proud of the woman I’ve grown into in my 20s. 

I challenge you to integrate reflection into your life, especially in your 20s as this is the decade when growth is boundless. Use these questions to center yourself and push yourself towards the person you’re destined to become.

Emalee Rodriguez

Emalee has always been a writer at heart, even winning the extremely important "Best Writer Award" of her 3rd grade class. In her real life, Emalee works in New York City with nonprofit organizations to create positive organizational culture, build HR infrastructure, and strengthen internal communications. For fun, she enjoys eating food and socializing with friends, exploring new places, petting random dogs, and being a New Yorker.

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