11 Questions Every Twenty-something Needs to Ask



What now?” is the question that plagues us in our 20s like chickenpox. The more we scratch, the worse it itches.

The overwhelming vagueness of “what am I doing with my life?” crushing us like the bully who sat on our head in 3rd grade.

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

After years of struggle, studying, searching, and being un-glamorously squashed over and over again, here’s what I believe are THE 11 QUESTIONS every twenty-something needs to ask to be successful.

11 Questions Every Twenty-Something Needs to Ask

 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 hanging out with friends feeling anxious or alive? Are your friends anvils tied around your ankles or jet-packs 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.

The common thread that runs through my favorite movies– the underdog who perseveres through pain, thrives from their authentic self, and succeeds at something sane people would never attempt. Your core values are laying 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 it will fix all their problems, when it actually has 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 it disappear. If you don’t like living with yourself, is it fair to ask someone else to do the same?

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

What’s the difference? Loving from your insecurities demands from others. Loving from your strengths gives to them. Loving out of your insecurities does not want to see people succeed more than yourself. Loving from your strengths hears of other’ s success and is the first to celebrate with them. Loving from insecurities daily demands “what are you going to do for me?” Loving from your 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 is there something there I can leverage into a career or product?

I heard John Saddington speak, a seriel entrepenur who’s probably best known for creating Standard Theme for WordPress, and he urged us to examine our hobbies. You’ve spent more time doing something than most people have in the world, how can you leverage that experience into something that could make you money? For John Saddington, he loved online computer games, so he started a online dating service for gamers. He knew the gaming world and he knew websites, put those two together and he had an over-night success.

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

8. What’s the main thing that’s 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?

9. What are my negotiables and non-negotiables?

What are you willing to give up and what are you going to cling tight 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 accomplished just one thing, what do I want it to be?

If you only had the choice to accomplish just one thing in your 20’s, 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?

101 Questions You Need to Ask in Your Twenties---small-cover-image

Find 90 more questions in my new book 101 Questions You Need to Ask in Your Twenties (and let’s be honest, your thirties too)

After the success of my best-selling book 101 Secrets for your Twenties, this new book captures the same hilarious, freakishly-accurate assessment of life as a modern-day twentysomething (and thirtysomething), but now we’re digging even deeper.

See what readers are saying about 101 Questions You Need to Ask in Your Twenties here. 

What real.live.people are saying about 101 Questions You Need to Ask in Your Twenties



  1. Rebecca Fraser-Thill

    These are great questions. I’ll answer #3: my favorite stories. They always depict people over the course of years, even decades, and show how life tends to evolve through happenstance and unexpected detours. Stories like this helped me keep perspective as a 20something that I didn’t need to plan everything out. Life simply happens. Yes, you need to be proactive and you need to have a sense of where you want to go, but having a “foolproof” 20-year plan just creates stress!

    • admin

      Great thoughts Rebecca. Love that you can see in your favorite stories the ability to persevere though unexpected detours. Definitely a needed trait in twenty-something life!

  2. Blue

    I’ll answer number 8, fear of failing. When I was 18, I had a certain notion of how 20something would be, when I reached 22, nothing actually happened. Somehow each and every plan failed. I haven’t accomplished what I said I would do. But now, I have other dreams and desires, and it’s all planned out. But I don’t go forward with it, because i fear that this time I can’t dodge the bullet, because i’ve been strong too much before! I am afraid that this time, if nothing happens, then I have no plans left.

    • admin

      Thanks for sharing what’s holding you back Blue. Definitely have been there myself time and time and time again…

      But I have to continually keep telling myself that the biggest failure of our 20’s would be never having any failures at all.

  3. Danielle

    As always great posting, loved reading it. I’ll answer no. 8 What’s the main thing that’s holding me back? I think that it’s the fact that sometimes I feel like I am not good enough or undeserving of good things that come my way. Lately I have been working on this and on myself. Hard work brings results and I am getting closer everyday to simply being happy and thankful when good things happen to me. I am still in the early stage of my 20 somethings and I like the direction that my life is headed thus far.

    • admin

      The old “I’m not good enough” is definitely a lie I believed for far too long. Awesome Danielle that you’re tackling this now.

  4. Cortney

    I’ll answer #8 too like the rest of everyone. I believe that the things holding me back are two fold. I have a fear of failing and a fear of being alone. I had this “plan” of how my life would look right now and I’m not anywhere close. I have a good job but not one I love, and I’m about as alone as you can get. The past year I’ve realized that this isn’t about my “plan” but God’s and am working really hard on praying through the feelings of failure and being alone. These concepts still regularly plague me, but at least I have some ammo against them!

    • admin

      Thanks Cortney. Fear is a scary thing, isn’t it! But a huge step is naming what you’re afraid of, so that you know how to counter-act. Sounds like you’ve done that and that you’re seeing the value of this season. That’s awesome

  5. Jess

    Okay, I’ll jump in on #8 as well. Sort of ties into #1 too. Have been wanting to say this out loud to someone, but I feel as though the relationship I am in is what holds me back. There. I said it. Getting out is tougher than I thought it would be though. I feel as though it drains me to be around this person. I could go into details, but I’d rather not. Just want to start moving forward with my life soon to see what is on the other side of this mess, hopefully a rainbow and a pot of golden opportunities. Your writing encourages me and gives me hope that I can do/be more than I thought. These questions are a great place to start. Thank you.

  6. Chris

    #7 I have a nonstop imagination and wish I could put pen to paper for at least half of the stories that I’ve come up with.

  7. admin

    Thanks Jess for the kind words.

    Yes, relationships can sneak up on you can’t they? The thing that once was so perfect now riddled with glaring imperfections.

  8. Heather Dawn

    I have never thought about #3 before but it’s really true!

    I guess the common thread between my favourite movies is “exuberant girl who sometimes feels misunderstood by those around her because of her desire for adventure, her wild imagination and her inability to keep her mouth shut finds security and a happy ending…” so basically watching them over and over helps me to convince myself that if these characters (who closely resemble myself in different ways) can find that ending, so can I.

    Thank you for that moment of self-discovery!

    These are all great!!

    • admin

      Awesome Heather. Great insight!

  9. Erika Simone

    #3 – My favourite stories are all ones about a small group of people supremely interested in each other, all the little things they do together and the lessons they learn along the way. ie. The Pickwick Papers, Anne of Green Gables, Eight Cousins, Tom Sawyer. I wonder what that says about me?

    By the way, Paul. This website has saved me many a headache and feeling alone and ridiculous at 22. Thank you.

    • admin

      Awesome Erika! Thank you.

  10. Amanda

    First off, I really appreciate this list and will share it with some of my friends who are struggling right now with being in their 20s and having no idea where to go next.

    The question I struggled most with was #2, which really hit home that I don’t know many inspiring people. I want to be an inspiring person to others so now I have to realize how to do that on my own.

    Recently, I discovered Sarah Kay on TEDx. She is an amazing spoken word poet, writer, and founder of Project V.O.I.C.E. This discovery also led to my first interaction with spoke word and my first open mic night where I actually got to hear Sarah talk on my college campus. If I could be anyone, I would want to be like her–full of life, aware of the world, creative, adventurous, and most of all, outspoken.

    • admin

      Awesome. Thanks Amanda. Yeah I think many of us get inspired by authors, historical figures, and Ted Talkers 🙂 so definitely run with that! Sounds like watching her gave you some great insight on what makes you feel alive!

  11. Beth M

    Great Questions Paul, I’m spending a night reflecting on them – Thank you – it’s good for me to see that (at 28) things are going well in my life.

    As for which question #9 – My non-negotiable is free time with my family, friends, and just self-learning. I learned this pretty early in my twenties, but you can always make more money (or get by with less – and oh man, sometimes I’ve gotten by on less) – but you never get more time.

    Be very very wary before adding new projects, and taking on demanding roles and jobs.

    • admin

      Thanks Beth! Great points

  12. Leighann

    Number 11 got to me the most, and I had an answer right away! I want to write a fiction novel for teens! I have always loved to write and being in school has made me busy, but I plan on finishing my book in the next 3 years!

    • admin

      Yes Leighann to an awesome dream!

  13. Jess

    This list is excellent, and right on par! Numbers 4 and 5 intrigue me the most right now. I sort of thought I was loving from my insecurities, but I couldn’t quite think of the correct term/I didn’t realize that’s what I was ACTUALLY doing until I read this article. Thank you for including it, otherwise I might not have given it a second thought so soon. It’s such a poisonous feeling and I feel selfish just admitting that I have this problem. How does one begin to get over it? Is it just a matter of forcing yourself to stop in the moment? Or do I move MYSELF forward so that I don’t feel so inferior when good things happen to those I love?

    Number 3 is also great. The main characters of my favorite stories live inquisitively with a passion for philanthropy and a touch of whimsy. These are attributes I admire.

    • admin

      Thanks Jess! Yes loving from our insecurities is a tricky one because we call it “love”, yet it’s mainly wrapped in our own selfishness. It’s definitely a tough one to stop, and we will probably never fully do so. But the more we become whole ourselves, the more we can love from that place of security.

  14. Kyla

    Number 11: I would want to run a full marathon, it’s a goal I’ve had for a while but university has always been my excuse when I get stuck in a training rut. I’ve only ever done a 10k so far.

    • admin

      Awesome Kyla! A 10K is 10 more K than I’ve ever run. Sounds like you’re on your way!

  15. Miriam

    hey! 🙂 thanks for the helpful questions! in answer to #8 i’d say I think my constant battle is with my desire to be popular and liked by people. I know I can never please everyone, and sometimes some people just don’t click, but my fear of people NOT liking me pervades absolutely every other area of my life and constantly holds me back from really being the person I want to be.

    • admin

      Miriam! Wow, I can so relate. Needing to be liked is definitely something I struggle with as well.

  16. Lydia

    I’ll answer #11. I am almost 21 and moved out of my parents’s place but am living with my sister and Brother-in-law. By 29, I would like to be out on my own, doing something with horses, and preferably on a farm. I am taking the first step this summer by going for an internship working with horses. I’ll be the farthest away from all my family I have ever been and staying with people that I have never met. I’m freaked out excited and scared to death!

    • admin

      Lydia! Music to my ears. I worked on a ranch for a few summers. Some of the best experiences of my life. Keep taking those steps towards the vision of your future.

  17. Morringhan

    I answered these in my blog, and it was really a great exercise on getting past the “what now” and onto the things I really needed to be focusing on.


    • admin

      Awesome Morringhan! Pumped you took the time to answer them. Hopefully it helped.

  18. Akeets

    I’ll answer number 8, as I think it is the one with most weight.

    Fear of failure and going too hard on myself has got to be the one thing that holds me back.

    Its easy to mix this up with challenging yourself. Just because we put ourselves outside of our comfort zones, or push ourselves, doesn’t necessarily mean we have to berate ourselves.

    • admin

      Great insight Akeets! “going too hard on myself” Yes, we think we’re doing ourselves right, by treating ourselves so wrong!

  19. Ryan

    Insightful post- it doesnt come a moment too soon for me- I think I really want to finish one of my stories and publish it- just to say I could and I did it- forget the money or the fame- those are probably just silly. I want, for once- to point at the fences and deliver for myself.
    -Thanks again

    • admin

      Awesome Ryan. I know that same feeling very well.

  20. Sarah

    This is an amazing list! I’m excited to spend some time journaling about this on vacation. I especially like #3. My favorite stories are Pride and Prejudice, Jane Eyre, Little Women. I love characters who are independent, level-headed women with strong faith. They are willing to make the sacrifices necessary to build a healthy, fulfilling life for themselves and they find inner strength and moral courage in the process. I always find that very inspiring.

    • admin

      Great analysis Sarah. Sounds like you’re finding some key values that are driving forces for you.

  21. Jessica

    Oh boy these are terrifying questions. Thank you for your last sentence because i genuinely would have left this post in the back of my head if it wasn’t there.

    # 8 – What’s the main thing holding me back?

    Motivation and hopelessness. Unburdened by the deadlines of college I find myself marathoning TV shows on Netflix and reading lots of dystopian novels.Every time I open up the interwebs with a purpose of searching for jobs to apply to I find myself finding very little that I feel I could do and that I feel even remotely interested in doing. And it takes days for me to write a cover letter without pressure from anyone.

  22. S. Taylor

    I’ll answer question 5. I love from my insecurities and I’m working to love from my strengths. When I love from my insecurities, I can’t share in the awesomeness that others are experiencing and I can’t be completely happy with their success. While they are telling me about an amazing addition to their lives all I can think about are the things I lack in mine. Loving from my strengths reverses this because I view myself as someone already fulfilled.

  23. Austin

    Excellent questions, but #8 got me good. Social anxiety/fear of rejection. I hold it all in because I’m afraid people won’t like the real me. I need to stop trying to be someone I’m not. I need to stop being so hard on myself for not being perfect. Jesus loves me. I love me. Why am I using my time and energy trying to impress people who wouldn’t like the real me anyway? That’s gonna stop. The thing I care about most is loving people, but I have to start with me.

    • admin

      Awesome Austin. Great thoughts!

  24. Julianne

    Hey Paul, Thanks for sharing this article I found it really helpful as someone who is in their early twenties! I would like to know if you know of any extra resources on loving out of insecurity vs. strengths? I think I really struggle with that and I would like to understand it more. Thanks!

  25. Jeremy

    1.) The people I am surrounded by are definitely jet packs. I’m surrounded by an incredible group of people and I couldn’t be more thankful. They challenge me and push me and it makes a world of difference in my life.

    5.) I definitely struggle with insecurities and unfortunately tend to love from those insecurities at times. I’m definitely working to move past those in order that I can be a friend that is the first to celebrate in their success.

    6.) I believe I am ripe with talent in the area of words (more so with talking and meeting new people, but I love writing and am trying to get better). I’m a student of life and love to learn, and then share what I’ve learned with those around me.

    I’m not so ripe with talent when it comes to sports. I enjoy getting outside with friends and playing pick up but I think it would be wise to embrace this gift of words that I feel has been given to me.

    7.) I love photography and writing and would love to find an avenue to get paid doing it. Due to my lack of experience and revenue…I’m at somewhat of a stand still in that process. (But I see this period of my life as a chance to get more experience!)

    8.) The main thing holding me back is fear. Fear of failing, fear of the unknown…I’m hungry and eager to be an entrepreneur and help others, but I don’t know how to talk the first step in that direction.

    10.) What breaks my heart is the existence of human slavery in this generation. Whether it’s the sex slave trade or forced labor, I hate the fact that their are people that have their rights stripped from them, against their will. I will do anything to play even a small part in joining the fight against this evil.

    11.) On the last day of my 20’s, I want to look back and see a business that affects the lives of several people directly for a good cause. I have no idea what that could look like but I want to create something that blesses other people on a daily basis.

    • admin

      Amazing insight Jeremy. Way to take time answering these!

  26. grace

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

    I would like to be able to publish my own book with my own illustrations in it. Or even just a coloring book for kids. I’d be happy with that… I think.

    • admin

      Thanks MJ!

  27. Paige

    Hey, i’m currently answering all of these questions as blog entries on my site.
    However… i’m on number two and i guess this is a topic i’m struggling with. I wondered if anyone has answered this question yet as it seems to be the one which is avoided most?

    • admin

      Thanks Paige. Any luck with that question? It can be someone who inspires you from history, from your own life, or even a fictional character from a story that inspires you. Awesome that you’re working through these on your site. Way to go.

  28. Karabo Grace Tledima

    I think my biggest lesson is being discontented as well as grateful all at the same time. I hate my cubicle job, but I am grateful I have a job. Sometimes I forget that dreams are made of the actions that lead towards them. I guess we have been inundated with “exceptions to the rules” that have made us feel like we have to BE “exceptions to the rules”…I have been so frustrated at not yet driving, at not having my own space…but I am realising that being my 20’s are a period of digging and levelling, and laying a foundation…and in any architectural process, that always takes longer. Building walls is an easy process when they have something unshakeable to stand on. You are refreshing, and I am grateful you wrote your book. Much love, Karabo

    • admin

      Thanks Karabo for these great, insightful thoughts! Love this line — “Building walls is an easy process when they have something unshakeable to stand on.” Well said!

  29. Kaileannah

    Love this! Great inspirational read

  30. Giverny

    Your posts are incredible! So helpful – thanks.

    • Paul Angone - All Groan Up

      Thanks Giverny! There’s lots to explore here at All Groan Up that’s for sure. Excited to connect more.

  31. Chelsea

    This is great. I love #4, #5 and #10. This is a great list.

  32. Carly

    I really need this right now. Thank you.

  33. April

    My Answers

    # 1: it excites me

    # 2: Bo Sanchez, he’s a Catholic Preacher. He’s preaching with humor, a very good writer too, God-fearing person, Loves his wife and his children and he makes time for them no matter how busy his schedules and most of all he’s full of wisdom and passion. I want to be that passionate like him.

    # 3: Top Three Fave Movies:
    1. God’s Not Dead
    2. The Bible
    3. Fireproof
    Their Common Thread? Faith. Faithfulness

    # 4: Yes

    # 5: I’m genuinely happy seeing other people succeed but sometimes I wish I had their perseverance.

    # 6: Talent:
    I can sing, draw, write, fix the Rubik’s cube

    Things I’m not:
    I can’t dance and act. I tried to learned the guitar coz I really wanted to learn but it
    bores me sometimes so I just learned the basics and some strumming patterns.
    (WTH happening to me??!)

    # 7: I love reading books and my question is: How can I make money with that?

    # 8: Fear of the unknown, fear that I might fail again and again and again. Anxiety and

    # 9: Negotiable and Non-negotiable? Well as long as I’m enjoying what I’m doing, I’m good
    with it. It doesn’t matter If pay check. (Maybe that’s why I’m always resigning from my
    work, I can’t find what I really want! God, I actually experiencing Quarter life Crisis since
    I was 17 when I started to work.

    # 10: What breaks my heart? Arrgh! This is a hard question than I thought. Well, seeing my
    Parents and families suffering really breaks my heart in two. (Is this counted?)

    # 11: If I accomplished just one thing? The first thing that come to my mind is to actually
    ‘make up my mind’ without having second thoughts. This is hard really, I don’t know if
    I’ll do this or that and in the end, I do nothing! Tsk. Tsk.


    And I also want to take my Masteral Degree.


    Find a JOB!!! That freaking JOB that I’ll love and bring out my passion!!!!

    See that? I can’t even make up my mind in question # 11.. 🙁

    • Paul Angone - All Groan Up

      Way to go April for taking time to go through these. Well done! Looks like you had lots of valuable insight. Awesome

  34. Nisha Varghese

    Love this!!!

  35. Asutay Meriç

    Hey, I really like the article. Mostly, I found that topic, what should we do about life, in general. However, this one is quite inspiring. Thanks!

  36. Sara

    Hey, Paul. Here’s the thing with me. I love my close friends dearly, but none of them are in good places either. We all feel anxious and depressed. Nothing post-college is as we were led to believe, and the college won’t really help us. Are we good company for each other right now, should we be alone instead, or what?

  37. cjmacc

    I feel right when I read this, for being just a portion of your book. Thank you for sharing your life. I’m 21 I don’t drink I have a addiction.


Submit a Comment

Your email address will not be published. Required fields are marked *

You’ve got questions.

We’ve got your-


SurVival PAckAge

A free, super-stuffed care package of resources to help you get through your twenties (and thirties too).

Order my new book "25 Lies Twentysomethings Need to Stop Believing"!

25 signs its a quarter life crisis

Instantly access: 

- "3 Ways to Pay Better Attention to the Answers Right in Front of You" - a quick, three step action guide to paying better attention that you can implement today.

- The first two chapters from best-selling author Paul Angone's new book Listen to Your Day: The Life-Changing Practice of Paying Attention.