20 Questions to Ask Yourself to Make the Most of Your 20s

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Your twenties: it’s a decade of change, growth, and endless possibilities. It’s a time for mistakes, self-discovery, and the gradual transition from the carefree days of your youth to the responsibilities of adulthood. These are the years (and the choices) that will shape your future in countless ways.

Do you choose to go to college and possibly rack up student loans that you’ll pay off for 40+ years? To get married? Do you make a cross-country move for a career opportunity? Do you have children? What about exploring your sexuality? Do you get a pet?

These are only a few of the questions that might be haunting you during those challenging – yet amazing – years.

All of the choices you make in your twenties can drastically affect what the rest of your life looks like. No pressure. 😕

Don’t worry, that’s what I’m here for! Let me talk you through how to make the most of your twenties by asking yourself these 20 questions.

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Why Your 20s Are Such an Important Stage of Life

In this viral TedTalk from psychologist Meg Jay, she emphasizes the importance of our twenties, referring to it as the “defining decade.” Jay says that no one gets through adulthood without going through their twenties first. It’s a period where pivotal decisions are made – decisions that can impact our careers, relationships, where we live, whether we have children, and the lifestyle we choose to lead. 

Studies show that 80% of life’s most defining moments take place by age 35. The first ten years of your career have an exponential impact on how much money you’re going to earn in your lifetime. By age 30, more than half of adults are married, living with, or dating their future partner. The brain has its last growth spurt in your twenties as it rewires itself for adulthood. We know that personality changes more during your twenties than at any other time in life, and we know that female fertility peaks at age 28.

Let’s be honest: Your twenties are fun, but they are also a bit scary. It’s a time to educate yourself. But more than that, it’s a unique opportunity for self-discovery and personal growth. It’s during this time that you have the chance to truly get to know yourself as an individual–your strengths, weaknesses, dreams, and fears.

How can you do that? How can you best get in touch with your most authentic self? Well, it all starts with asking the right questions 😉

Your 20s — The First Decade of Adulthood

Think of your twenties as a time when you are like a seed planted in fertile soil, ready to sprout and grow into something beautiful and unique. It’s a decade marked by change, growth, and endless possibilities. 

As you navigate through this transformative period of your life, you’re faced with hard decisions that can shape your future in profound ways. These decisions aren’t just about laying the groundwork for what lies ahead; they’re about creating a life that resonates with your deepest passions, values, and aspirations.

Reflecting on my own journey through my twenties, I can’t help but marvel at how much I learned and grew during those pivotal years. Like many, I started the decade with a mix of excitement and fear, unsure of what the future held but excited to embrace the adventure of adulthood. Looking back now, I’m grateful for the lessons learned, the challenges overcome, and the experiences that have molded me into the person I am today.

One of the most important realizations I’ve had is the importance of self-discovery. Your twenties are the critical time to start peeling back the layers of societal expectations, peer pressure, and external influences to uncover our authentic selves. It’s a period of introspection and self-reflection, where you can ask yourself tough questions and confront your deepest fears and desires. What do I stand for? Who am I? What do I want out of life?

What Questions Should You Ask Yourself?

As you move through this first decade of adulthood, use this time to ask yourself the important questions. As Meg Jay says, “30 is not the new 20, so claim your adulthood, get some identity capital, use your weak ties, and pick your family. Don’t be defined by what you didn’t know or didn’t do. You’re deciding your life right now.”

Here are twenty insightful questions to help you make the most of your twenties — not only for the decade but for your entire life.

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20 Deep Questions for Your 20s

1. How would you describe yourself? And are you proud of yourself?

Take some time to reflect on your values, beliefs, and character traits. Embrace self-awareness and strive to become the person you are proud to be.

2. What is your personality type? How does that impact your interactions with others? 

Try taking a personality metric like Meyers-Briggs or the Enneagram. These valuable metrics can help you to gain insights into your behavior, communication style, and relationships with others.

3. What are your life values?

What principles guide the decisions and actions that you take in your life? If you are unsure, reflect on what principles you respect and admire in others. How can you adopt these in your own life?

4. What are your strengths? Are you using these to their full potential?

Recognize what your unique talents and abilities are— and be confident in yourself! Start to seek opportunities that will leverage your talents in both your personal and professional pursuits. 

5. Are you pursuing a career that aligns with your passions?

Oftentimes, we start a career because we need to get a foot in the door or, practically, we need to make a living. But is that career actually reflecting your interests, values, and long-term goals?

6. How do you handle failure and setbacks? What about stress and pressure?

Reflect on your coping mechanisms during challenging times, and consider strategies to manage stress more effectively. 

7. Do you prioritize self-care, health, and well-being?

Start a self-care routine that prioritizes your physical, mental, and emotional health. Make time for yourself daily! 

8. What are your financial goals and habits?

Start setting clear financial goals for the short- and long-term, adjusting your spending and investing early to build healthy financial habits. Do it now and thank yourself later — a little bit saved in your twenties equals a lot in your sixties.

9. What kind of friendships do you want to cultivate?

Making friends when we’re older can be tough. Consider the qualities you value in friendships and invest in nurturing meaningful connections with others.

10. What do you value and look for in a long-term romantic partner?

Say goodbye to Tinder, and start prioritizing meeting people with the qualities you desire in a future partner. If you’re ready to settle down, start acting like it!

11. How is your relationship with your parents and family? What do you want for these connections in the future?

Think about areas you may want to grow in with your family. Do you spend enough time with them to stay connected? What bonds need mending to achieve a better relationship for the future?

12. What motivates you? What inspires you?

Figure out your motivations and inspirations, and start to channel them into meaningful pursuits and goals. Staying true to these internal drivers is key to building a happy life!

13. What are your negotiables and non-negotiables? (In relationships, at work, and with yourself)

Clarify your boundaries and values in various aspects of life, and advocate for what aligns with your priorities. If you don’t establish these for yourself, no one will.

14. What triggers you? And why?

Understanding your triggers is essential to heal old wounds and develop strategies for managing them constructively.

15. How do you feel about taking risks and stepping out of your comfort zone? Are you holding yourself back?

Evaluate your comfort level and push yourself to get a little uncomfortable sometimes. This is the only way to challenge yourself to embrace new experiences and opportunities — and, ultimately, grow as a person.

16. What skills or hobbies do you want to develop?

Identify areas that interest you, both personally and professionally, then pursue opportunities to learn new skills and explore. Don’t be afraid to start as a beginner! Your twenties are a fabulous time to invest in yourself!

17. Are you nurturing your creativity and imagination?

Everyone has a creative side, but as people get older it’s easy to lose sight of. Start exploring your creativity through artistic endeavors, hobbies, and innovative thinking.

18. How do you define success in life? What about happiness?

Define what success looks like to you — then start to align your goals and actions with these definitions.

19. How have you changed in your 20s? How do you want to grow in your 30s and beyond?

Reflect on your personal growth and development during your twenties and envision what your future holds.

20. What legacy do you want to leave behind?

Consider the impact you want to make on the world and the legacy you want to create through your actions, relationships, and contributions. How can you make this vision a reality?

RELATED: If you want to get to know yourself on a deeper level, grab here your “30 Self-Discovery Questions” freebie!

Use Your Time in Your Twenties Wisely

While my twenties were a decade of self-discovery and growth, I know that the journey of growth is far from over. If there is one thing I’ve learned in my forty years, it is to embrace the lessons life throws your way and use them to explore, learn, and evolve as a person. These experiences are the threads that will weave the unique tapestry of your life.

So, I want to leave you with one of the most important questions you could ever ask yourself in this decade: “How will you make the most of your twenties?”

I encourage you to embrace the journey of self-discovery, pursue your passions relentlessly, and not be afraid to step out of your comfort zone once in a while. Remember that the choices you make today will shape the person you become tomorrow. So seize the moment, live boldly, and embrace the endless possibilities that lie ahead. 

Just as Meg says, “Claiming your twenties is one of the simplest, yet most transformative things you can do for work, for love, for your happiness, and maybe even for the world.” Your twenties are a decade of change, growth, and transformation – it is your right and responsibility to make the most of them.

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Q: “What lessons have you learned in your twenties? What advice would you give to someone entering this pivotal decade of life?” – Share your thoughts in the comments! 🙂

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