10 Questions to Ask Yourself In Your Twenties

Your twenties are a great time for personal exploration, discovery and growth. Below you will find a list of questions curated especially for twenty-somethings. These questions will challenge you to dig deep and think about who you are and where you are going. Prepare yourself for some uncomfortable moments, some “Ah-ha” moments, and some “wait, WHAT?” moments – they are all part of the process.

And as always, try to maintain a level of judgement-free awareness of yourself and your thoughts. We aren’t here to find the right answers, we are here to uncover your answers.

If you want to record your answers as you go – click here to access the 10 Questions to Ask Yourself In Your Twenties Worksheet.

Who do I want to become?

This is a big question. And one that probably left you with a long pause after reading it. Please note this question asks who not what. Don’t focus on becoming a lawyer or an entrepreneur. Focus instead on becoming someone who is brilliant at critical thinking, or exceptional at identifying a problem and creating a solution. Becoming is a hugely important topic in coaching, as we focus on where we are going, and what will be there when we arrive. Take some time to think this one though – who do you want to become? What values does that individual have? What do they do? Why do they do it?

Who am I now?

The observation-evaluation feedback loop is critical to genuine self-discovery. Take an honest snapshot of who you are as an individual right now. Note your values, strengths, assets (not just financial), and habits. Once you have a clear picture of who you are, go back to that first question, Who do you want to become? Where are the biggest gaps here? What do you need to work on most?

What is the most important thing for me to have accomplished by my 30th birthday?

Don’t let your thirties sneak up on you only to slap you in the face with an invoice for a decade wasted. Think hard about the one thing that would be most meaningful to have accomplished by the big 3-0. Try your best to drown out the chatter in your brain around the “should-do’s”. Trust your gut here – and don’t be afraid to dream big.

What are your strengths?
Owning your strengths is hugely important to personal success, and often undervalued for individuals in their twenties. If you find yourself getting stuck on this question – it might be helpful to ask those around you. Reach out to the five people that know you best and ask them what they think your top three strengths are. Then ask them which one they think you undervalue the most. Review this information and evaluate what you find. Are there any overlaps? Does each individual see a completely different side of you? Are there any surprises?

What is the biggest factor holding me back?

This one can be a bit tricky. Often if there is something big in your life that creates a barrier between you and your goals and dreams – there is a reason you haven’t already dismissed it. Is it a person? A job? A bad habit? Take a minute to imagine your life without this factor. How does your world change? What opportunities pop-up, expand or multiply? Is it worth making the move to rid yourself of this obstacle?

What is the biggest factor zapping your energy right now?

In order to get somewhere exciting, you are going to have to hustle, and hustle hard. There is just no way around it. If you want to make something of your life, you are going to need to work hard. To work hard we need both inspiration and energy. Let’s start with your current energy levels. On a regular basis, where would you rate yourself on a scale of 1 – 10 with 1 being “I’m not getting out of bed today or ever” and 10 being “Look out Energizer Bunny, I’m coming for you!” Now that you have that number, what is the one thing that kept you from saying one point higher? Often this can be something/someone you are tolerating. What are you tolerating on a daily basis? That commute? That friend? What would your life look like if this was no longer a factor?

When was the last time you failed?

Think about the last time you fell flat on your face with an epic failure. We often play it safe in life, putting ourselves in situations where we have the illusion of control around the outcomes. Your twenties are a time for taking risks, falling hard, learning and moving on.

What would you do if you couldn’t fail?

If there was one thing in your life where you really put yourself out there and risked great failure what would it be? Take a minute to eliminate the option of failure as an outcome from any given scenario. You can’t fail – so what do you do? What risk do you take? How great does that feel?! Here’s a big secret – failure can be a great thing.  If you shift your thinking away from a perfectionist mindset and focus on learning, failure opens up so many possibilities. Instead of doing something “wrong”, look at it as “Oh that didn’t work, what should I try next?”. Stay curious, stay playful. If you want it bad enough – you will get there, and hopefully learn meaningful strategies along the way.

Who’s on my team?

Your team can make you or break you in your twenties. Do you surround yourself with people who challenge you to be the best version of yourself? Do they build you up? Inspire you? Challenge you to be a better person? Is there something you can learn from them to achieve your own dreams and goals? How are you supporting those on your team? Do you give as much as you get? Make sure to set yourself up for success by maximizing the relationships that are meaningful to you. Investing in the right relationships now will pay off enormously down the road!

What do I love?

It is powerful to recognize what you love. When you love something you can do it for hours without knowing a moment has passed. Being able to experience ‘flow’ will serve you like nothing else. Discover what you love, embrace it – and make sure you do it regularly! This will keep you inspired, happy and healthy, setting a strong foundation for achieving your goals as you move  into your thirties.

Message from a coach:

I hope you found this list of questions inspiring and that you learned something about yourself in the process. If there was a particular question you were stuck on or even skipped over – be aware of that. You might not be ready to dive into certain areas just yet but awareness is the first step on that journey.

If you discovered something about yourself as a result of this list, I would love to hear about it! Let me know in the comments below, or send me an email. I would especially love to hear the one thing you want to accomplish by your 30th birthday!

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