101 Questions You Need to Ask in Your Twenties

1. Ask Good Questions to Find Better Answers

To find good answers, we must first ask good questions.

Power of Inquiry. The quality of your life is often determined by the quality of the questions you ask. Good questions are the starting point for solving problems, making decisions, and understanding yourself. They provide a strategic framework for navigating life's complexities and uncertainties, especially during the defining decade of your twenties.

Strategic Framework. Asking the right questions helps you adapt, change, and grow when life doesn't go as planned. It's about being purposeful in the process, constantly tacking, pivoting, and reconfiguring your journey. Without good questions, you risk traveling off course and becoming stranded.

Lifelong Process. This isn't a one-time test but a lifelong journey of self-discovery. Use questions as a reference guide, tweaking, changing, and adding to them as you evolve. Community stokes clarity, so grab a few friends and work through these questions together.

2. Transitions are Tough, But Incredibly Important

Transitions are not simply a bridge to the next important season of your life. Transitions are the most important seasons of your life.

Navigating Change. Life transitions, especially in your twenties, can feel like a punch in the gut. They're not light and breezy but significant and often the toughest seasons to navigate. These transitions involve breaking up with a season of your life and the version of yourself you were during that time.

Embrace the Process. The biggest mistake is trying to rush through transitions to find a new normal. Instead, marinate in them, allowing them to carry you to your intended destination. Transitions are not just a bridge but the most important seasons of your life.

Faith Over Fear. As you walk through transition, let faith guide your way, believing it's taking you to a better place. Fear will tempt you to return to what was, even if it was terrible, because at least it was familiar. Let your transition lead you to the future you desire.

3. Authenticity Connects Us; Pretend Perfection Isolates

We don’t connect with each other through our pretend perfection. We connect over our shared struggle.

Shared Struggles. We often hide our struggles, trying to project an image of perfection. However, it's through our shared vulnerabilities that we truly connect with others. Authenticity starts with you; be brave enough to go first.

Building Walls. The walls we build to protect our image only keep people away. We try to keep our wounded pride intact while it lies lifeless on the floor. It's important to remember that we don't connect with each other through pretend perfection but over our shared struggles.

Be Brave. Authenticity starts with you. Be brave enough to go first. Share your struggles, your imperfections, and your fears. It's through this vulnerability that you'll create meaningful connections and build genuine relationships.

4. Your Friends Shape Your Life; Choose Wisely

Your life will resemble the lives of your closest friends. Does that fact excite you or freak you out?

Influence of Association. The people you surround yourself with significantly impact your life. Your friends can either be anvils tied around your ankles or jetpacks helping you fly. It's crucial to assess whether your friends are taking purposeful steps forward or still playing beer pong in the basement.

Friendship Scorecard. Evaluate your friendships by listing the five people you spend the most time with and rating them on a scale of 1 to 10, with 1 being an "Anvil Friend" and 10 being a "Jetpack Friend." Add up the scores to determine your "Friending Category."

Quality Over Quantity. Making and keeping friendships in your twenties is challenging. Be willing to take risks in your relationships, pursue friendships through awkward phases, and let go of those that continually bring you down. A bad friend is worse than a good enemy.

5. Sacrifice Strategically to Pursue Your Purpose

Pursuing something bigger than yourself will cost you something. So if you’re going to pursue your purpose, what are you willing to sacrifice?

Cost of Purpose. Pursuing something bigger than yourself requires sacrifice. Determine what you're willing to give up to achieve your goals. This could be anything from material possessions to time or comfort.

Honda Civic Hatchback. What's going to be your "Honda Civic Hatchback"—functional but not exactly something you're pulling up to valet parking? What are you willing to give up, and what are you going to cling tight to?

Non-Negotiables. Figuring out what you won't give up and what you will sacrifice will tell you a lot about what you should pursue. Are you willing to move anywhere, but you don't want a job that expects more than 40 hours a week? Is job flexibility a nonnegotiable, or is it job stability?

6. Embrace the Power of "Not Knowing"

Your twenties aren’t about them going as you planned. But how you adapt, change, and grow when they don’t.

Redefining Success. Success in your twenties isn't about things going according to plan but about how you adapt, change, and grow when they don't. It's about being purposeful in the process, covered in eraser marks and revisions. Failure only happens if you stop writing.

The Power of Questions. To find good answers, you must first ask good questions. There's nothing more powerful and important in your twenties than the questions you bring to it. A good question is a problem half-solved.

Curing Comparison. As you go through these questions and struggle to find the best answers, you'll stop worrying so much about what other people are doing because you'll be focused on what you need to be doing. This helps cure Obsessive Comparison Disorder.

7. Vulnerability Fosters Connection and Support

We all need people in our lives to tell where we are going.

The Danger of Isolation. There is a danger in going at anything completely alone. We need to tell people where we are going and where we have been. The remedy is something simple, yet extremely difficult: vulnerability.

Authenticity Matters. If you sing about the need for all of us to be authentic and vulnerable while you inauthentically hide behind each piece of advice and the exciting parts of your journey, then you're just another clanging symbol amidst a cacophony of unnecessary noise.

Courage to Open Up. It takes a lot of courage to talk about where you lack the most courage. We have to be courageous enough to open the doors and let others really see inside. We all need to be brave enough to be vulnerable.

8. Take Action Amidst Overwhelming Choices

When you don’t know what to choose, make a choice that you’re going to choose something.

Paralysis by Analysis. Today more than ever, we are suffocating in choices, options, and possibilities. Every choice you make means you're not choosing a million other options. This can lead to paralysis and anxiety.

Choose Something. When you don't know what to choose, make a choice that you're going to choose something. Not making a choice is a choice, and probably the least constructive one you can make. You don't learn anything staying in the same place.

Get Action. Make a choice that you're going to make a choice. Find your "I'm 77% sure" and give it a try. You won't know how it's all going to work out until you start doing the work. Drowning in options is a terrible way to die.

9. Fear is a Compass; Let it Guide, Not Stop You

What is fear keeping you from doing? Is it worth it?

Fear as a Barrier. Fear can stop you many times. It can hold you back from pursuing your dreams and living a fulfilling life. It's important to recognize what fear is holding you back from and ask yourself if it's worth it.

Stop Stopping Yourself. Fear had stopped me many times. Yet, Seth was right, of course. It wasn’t worth it. What is fear holding you back from? Is it worth the anxiety that comes from letting fear get the best of you?

Trying is Better. Never taking needed risks because of fear is not worth it. It typically never is. Trying and knowing is better than wondering what if. Stop stopping yourself.

10. Find Purpose in Your Pain

Oftentimes our purpose and passion is found in our greatest pain.

Redemption Business. God's in the redemption business—taking those broken pieces of our story and creating something breathtaking out of them. In every great story, the hero always experiences an "all is lost" moment before the dramatic rise.

World Changers. World changers typically have their greatest impact where they have experienced the most personal pain. Your passion and purpose might be embedded in the tragedies you listed above.

Problems as Purpose. If you're struggling to find your purpose and passion, look to your problems. Look at those tragedies you've experienced and see what is waiting there to be redeemed. Your passion is driven by the deep desire to solve a deep need.

11. Forgiveness Frees You, Not the Offender

Not forgiving is like drinking rat poison and then waiting for the rat to die.

Release the Bitterness. Man, being bitter just feels so right sometimes, doesn't it? You have every right not to forgive, yet holding tight to that anger is like letting that person repeat the offense over and over—completely tearing you apart while doing nothing to affect them.

Forgiveness is for You. Forgiveness is more for you than it is for the person you're forgiving. It allows you to be free and move forward. Unforgiveness is like hitching a big box TV to your ankle and then trying to run uphill.

Stop the Reenactment. Forgiveness means stopping the bitterness and resentment from continually seeping into your heart like a gas leak. Forgiveness means when your mind starts replaying the offenses in your head, and you dream about all the things you wish you would have said or done to them in return, you stop the reenactment.

12. You Are Enough; Chase Dreams, Don't Let Them Chase You

Sometimes the most inspired thing you can do is to keep showing up when you feel completely uninspired.

Identity Beyond Accomplishments. So much of your value was coming from the ebb and flow of success, so you kept getting tossed around by each new wave. Accomplishing less or more will never be able to sustain you.

You Are More. Your identity is not just one thing. You are not just one outcome. There’s not one noun that describes you. You’re not one job title. You are not defined by one relationship.

Chase Your Dreams. Do good work. Put your dream out there. Do your best to help others. Then, let it go. Your dream can’t fly if your identity and self-worth are clinging on to the back of it.

Last updated: March 3, 2025