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“Exploration” in Your Twenties doesn’t mean what you think it means

The idea of “exploring” in your twenties is a very common theme.


The idea of “exploring” in your twenties is a very common theme. Some people take it literally and explore the world, others explore things such as drugs or how much that can drink before they throw up. While these are explorations that, while not recommended, you can have in your twenties, the true meaning of this decade of exploration is to explore new paths and ideas.

But what does this mean?

This means you’re done with school (or close to it). You’re making money. You don’t have 5 hours of homework tonight. You’re free to start spending your after-hours trying things you haven’t been able to before. Instead of spending $500 on shopping spree, why not invest in that photography class you keep meaning to try? Why not start writing that book you keep talking about?

These explorations change as you move through your twenties but as a guideline, I’ve compiled a list from dozens of resources, friends, and firsthand experience of the adventures you should try throughout these ten years.

Age 20: Explore new friends.

I don’t mean you should ditch your old friends. Age 20 is the perfect time to meet new people especially if you’re a sophomore/junior in college. You have two more years of school to bond but you already have a few friends from your dorm so you don’t need to cling to anyone the way you did freshman year. Some ways to meet new people: join a new club. Study abroad. Invite someone from your classes to a coffee study date. Throw a small party and encourage friends to bring guests.

Age 21: Explore being alone.

The last 21 years of your life have been all about school with dozens of people your age whom you’re expected to interact with socially. You’ve had to make dozens of new friends and work with groups on projects for school. You lived in a dorm where you’re constantly surrounded by people. As fun as it is now, it can be hard to adjust from fulltime social interaction to much much less after college. Spend this year exploring what it’s like to be alone. Take walks in the morning by yourself without music. Sit in a coffee shop and quietly people watch for an few minutes. Plan evenings just for you with music you love, movies, and your favorite food. Take yourself out to eat. Spending time alone with your thoughts is a practice of self discovery that will become more and more important as you get older.

Age 22: Explore failure.

Yikes, right? Failure is such a misunderstood word. We’re taught to succeed and win all our lives and someone we’ve decided that failure is the opposite of these things. The opposite of success is complacency. The opposite of failure is also complacency. While they coincide, success and failure are very closely related concepts. As you prepare to graduate and find a job, explore what it’s like to fail. I don’t mean you should give up or fail a test. I mean, interview for a job you don’t think you’re qualified for. Cold email someone you admire (professionally or romantically) and ask for a coffee date. Post an Instagram you think won’t get any likes. Tim Ferriss talks about this idea in his book the 4 Hour Workweek. As I am encouraging you, he encourages his readers to try something they think is impossible. The only outcome is that you will learn something. You will learn that fear of failure should not stop you from trying. Maybe your idol never emails you back. But, maybe they do. The only way to find out is to try.

Age 23: Explore what you want.

For most of us, we’ve been spoon fed ideas about what life should look like and how we should get there. We should want a good college and we should want to find a job where we can work our way up to a position we want and make as much money as we want etc etc. At 23, it’s likely you’re becoming disillusioned and realizing how this path is corrupted and frankly boring. 23 year olds start questioning what they want versus what they should want. Do you want to become a partner at this law firm or do you want to be able to take a weekend off for once? Take this year to unashamedly explore what you want. You’re allowed to want to make a lot of money. You’re allowed to want a family and to settle down young. You’re allowed to want to be more powerful and influential. You’re allowed to want whatever you want. Take this time to figure out what that is.

Age 24: Explore new habits.

You’re a grown person now so it’s time to move past your Thursday-hangovers and Saturday night Netflix and pizza binges. These things were fun but 24 is the perfect age to start trying out some new habits and routines that will have a positive impact on the next years of your life. These new habits should be things you’ve been “meaning” to start doing but maybe haven’t committed to. If you’ve dreamt of being the type of person who does yoga and drinks tea every morning, now is the time to try out being that person. 

Age 25: Explore your relationships.

Whether you’re single or super committed or married or still “keeping it casual”, 25 is the time to focus on your adult relationships. Why? Because you probably have already realized ( and had a mental breakdown about) the fact that you’re almost 30 a.k.a. the age you may have told yourself you’d think about being married or having kids or both. Sadly, you cannot just wake up at age 30 and suddenly be in a happy and healthy relationship. 25 is the time to start assessing your romantic life and where you want it to go. Maybe you start going on blind dates or maybe you stop going on blind dates. If you’re married or already in a relationship, where do you see the two of you in a year? 5 years? Explore your relationship and it’s future through conversations with your partner.

Age 26: Explore your feelings about money.

26 starts to feel like real adulthood. You’re very much on your own, you start thinking about things like taxes and health insurance and long term career plans. With all of these come a central player of Money. Money can mean a lot of different things to different people. Do you worry about losing money? Do you feel like you don’t have enough money? Do you tie your personal success to a dollar amount? Explore some of the emotions you currently tie to money. Try something new that you haven’t done before. Maybe you start a retirement savings or even just a regular savings. Maybe you start viewing money as a means to save time (time is an arguably more valuable asset). Dig deep and solve your money mental problems now while you’re young.

Age 27: Explore new experiences.

At 27, you’re settled. You have a job, you’re crushing this whole “adulting” thing. But you’re also not. You’re starting to feel kind of boring and maybe even irrelevant and you’re not sure why. Well, when’s the last time you tried something new? Like something really new? A new restaurant, a new recipe, a new vacation spot, a new workout, anything? If you feel like you’re life is becoming a bit to habit-uous, it’s time to go back to your younger-years mindset and set out to try and learn something. This can be as simple as trying to cook a new meal or downloading DuoLingo to brush up on a new language.

Age 28: Explore your priorities.

While you should always have a clear list of life priorities, 28 is a good time to really sit down and literally write them out. Do a quick self evaluation of how the last 8 years have been. What are you satisfied with? What are your regrets? Take this list and explore some ways you can refocus your life around your top priorities.

Age 29: Explore time off.

The last 9 years have been an absolute WHIRLWIND and you probably cannot believe you’re actually 29. What’s great is if you’re like me, you probably plan to be 29 for a few years (or as long as you can pull it off) so you have some time to explore this one! Americans are notorious for being overworked and under-rested and it’s likely you’re slipping into this category. You have more responsibility at work and your life after work has more responsibility too. You want to take a day off but you’re afraid of “falling behind.” Let me tell you some hard truths: the world does not operate solely because of you. If you decide to take a mental health day tomorrow and stay home and unplug for the day, your company and your life will continue on without you. And that’s a good thing! You need to explore taking time for yourself and learning how to turn off work and slow down for a moment.

What are some explorations you are trying in your twenties?

Comment your suggestions below to be quoted in the post!

Originally published at medium.com

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