11 Questions Every Twentysomething Should Ask

Questions to help move on from "what now?"

Your twenties can be a rough time. You graduate college. You get a job—not necessarily the one you always dreamed of. You may move to a new city and start trying to establish yourself. But a lot of the time, you're just not sure where you're headed—or even where you want to be going.

Often, the question of “what now?” plagues us in our twenties like chickenpox. The more we scratch, the worse it itches. The overwhelming vagueness of “what am I doing with my life?” can crush us like the bully who sat on our head in third grade.

Our twenties can feel like being smothered in questions, but if we don’t ask the right questions, we will forever remain stuck.

After years of struggle, studying, searching and being un-glamorously squashed over and over again, here are 11 questions I believe every twentysomething needs to ask to be successful:

Our twenties can feel like being smothered in questions, but if we don’t ask the right questions, then we’ll forever remain stuck.

1. Do the people I’m surrounded by bring me life?

Are your friends taking steps forward or are they still playing beer pong in the basement? Do you leave from hanging out with friends feeling anxious or alive? Are your friends anvils tied around your ankles or jetpacks helping you fly?

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

2. Who inspires me the most?

Think about the one person you most want to emulate. Who is it? Now what is it about their story or character that draws you to them? Write down the words that come to mind. The person you want to be like the most tells you a lot about who you hope to become.

3. What are my favorite stories?

What are your top three movies? Is there a common thread that runs through each story?

If you want to see what matters most to you, look at the stories that resonate the closest. For me, the common thread in my favorite movies is the underdog who perseveres through pain, thrives from their authentic self and succeeds at something sane people would never attempt.

Your core values are lying on the surface of your favorite stories.

4. Would I want to live with me?

Before you start thinking about living with someone else, do you even want to live with yourself? Have you opened up your closet doors and faced your monsters?

Too many people go into relationships hoping that they will fix all their problems, when relationships actually have the magical ability to show you how many problems you really have. Like a third-rate magician, marriage puts big things behind a curtain, but does nothing to make them disappear.

If you don’t like living with yourself, is it fair to ask someone else to live with you?

5. Do I love from my insecurities or do I love from my strengths?

Loving from your insecurities demands from others. Loving from your strengths gives to them. Loving out of your insecurities means you don't want to see people succeed more than yourself. Loving from your strengths means you are the first to celebrate with others when you hear of their successes. Loving from insecurities daily demands “what are you going to do for me?” Loving from strengths asks others, “what can I do for you?” Too many people love from their insecurities, and that’s not love.

6. Where am I ripe with talent and where do I quickly deflate?

We all have talent. And we all have loads of non-talent we keep trying to transform into talent. Write down a few things you’re talented at and a few things you’re not. Then focus on the things you’re good at. Stop trying to chip away at that solid cement block when you have a soft block of cheese just waiting to be devoured.

7. What are my favorite hobbies/things I do for fun, and are they something I can leverage into a career or product?

I recently heard John Saddington speak, a serial entrepreneur who’s probably best known for creating Standard Theme for WordPress, and he urged the crowd to examine our hobbies.

There is something you have spent more time doing than most people in the world. How can you leverage that experience into something that could make you money? For Saddington, he loved online computer games, so he started an online dating service for gamers. He knew the gaming world and he knew websites, so he put those two together and had an overnight success.

For me, it’s telling stories. So I started writing them down.

8. What’s the main thing holding me back?

Is it an addiction? Anxiety attacks? Depression? An obsession with pinning pictures of rock-hard abs on Pinterest while drinking? What is the main thing that is keeping you from moving forward and who can help you cut the chain?

What are you willing to give up and what are you going to cling tight to?

9. What are my negotiables and non-negotiables?

What are you willing to give up and what are you going to cling tightly to? Are you willing to move anywhere, but you’ll never take a job that expects more than 40 hours a week? Is job flexibility a non-negotiable, or is it job-stability? Write a list of non-negotiables and negotiables, and then do your best to stick to that list.

10. What breaks my heart?

What injustice makes you angrier than a parrot being poked with a stick? And what’s something you can do about it right now? Knowing what breaks your heart can clarify what makes you feel whole.

11. At 29 years and 364 days, if I have accomplished just one thing, what do I want it to be?

If you only had the choice to accomplish just one thing in your twenties, what would it be? How do you take one step toward that today? Our twenties can feel like trying to walk with shoes covered in fast-dry cement, so how do we keep moving forward? Is it a phone call to ask for an informational interview? Is it asking a crush out on a date? Is it making an appointment with a counselor? What’s one small thing you can do today so that you can go even further tomorrow?


Rachel Morris


Rachel Morris commented…

Great article! As someone in this age bracket there are a lot of unknowns ahead that can often make me stress a little- these questions you have highlighted make me look at what I have in my hand at this moment. What do I have to use and who do I surround myself with? Really empowering, and also a lot of wisdom behind it!!! Keep up the great work!

Paul Angone


Paul Angone replied to Rachel Morris's comment

Thanks Rachel for the kind words! Pumped these questions resonated and gave you something tangible to answer.

Steve Cornell


Steve Cornell commented…

These are helpful "life-stage" questions. It reminded me of a 10 point inventory I put together that transcends life-stage. But I always like to offer a caveat about it being for personal evaluation not for judging others. Lists and tests easily become legalistic tools that promote sinful pride.

If interested, I offer 10 tests here http://thinkpoint.wordpress.com/2012/12/28/10-point-inventory/

Henrique Neves Bez


Henrique Neves Bez commented…

I've heard this "What now?" from so many people. Great Article!

Pastor Ted


Pastor Ted commented…

this is a christian article?

1. is self-centered, with no consideration of mission.
4. accepts living together outside of marriage.
6. encourages people to not develop discipline.

no scripture. very pop and psychobabble'ish without a clear biblical worldview.

this is what happens when our pleasure/fun is most important, and we do not work with all our heart as if working for the Lord rather than for men, or in this case, for self (Colossians 3:23).

Tia Beattie


Tia Beattie replied to Pastor Ted's comment

1. We are encouraged not to walk with the ungodly. This does not mean we cannot influence their lives, live, and work with them on a daily basis showing them the nature of Christ. This point is speaking on our close friendships and the healthy boundaries we are to set in them. Are our close friends bringing us life or leading us down a path farther from God? How are we to handle that?

4. I ask myself this daily. I'm married now, of course. However, before my husband and I lived together (we didn't prior to our marriage) and even before we dated I asked myself this question. I learned to cook, clean, etc in readiness for the spouse God had for me. This question in no way implies that it's okay to live together before marriage.

6. God has given us each our specific and unique talents. We are a body made of many parts with many different roles to play. This question encourages us to discover those talents given to us and focus our energy and time (discipline) on them, rather than chasing after the wind on things we may not have been gifted in.

Not every article needs to be riddled with scripture to be supported as Biblical. I agree we should never make pleasure an idol over mission or serving our God. This article merely encourages the reader to do deeper self-assessments, to discover how God has uniquely created and gifted us, and therefore delve into a deeper relationship with Him. To understand the desires He has put in our hearts, to realize His plan for us. It's not about pleasing ourselves, but focusing on lining up our desires with His and pleasing Him, as well as finding joy in pleasing Him.

Andy Hall


Andy Hall replied to Tia Beattie's comment

@ 'Pastor' Ted.....Ur Dum.

Andy Hall


Andy Hall replied to Tia Beattie's comment

Oh yeah, and good article and stuff. Very thought provoking and life altering and all that jazz.

Paul Angone


Paul Angone replied to Andy Hall's comment

Thanks Tia for the wonderfully thought-out and fruitful comment. Much appreciated.

Tim Chan


Tim Chan commented…

The first question is a great one - I asked myself this question when I was 25, and sadly some of the people in my life were not giving me life. So I made the difficult decision to see less of certain friends, and took steps to find more mentors in my life (which I write more about there: http://timandolive.com/finding-a-mentor/)

Paul Angone


Paul Angone replied to Tim Chan's comment

Thanks Tim. I definitely agree that twentysomethings especially need some Generational Potpourri in our lives to see the Questions from different angles.

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