20 Tough Questions Every 20-Something Should Tackle Today


I’ve always been an advocate of therapy. I’ve never seen a therapist myself, but I’ve witnessed friends in totally stable states of psychological health achieve dramatic mental rejuvenation with 2 hours a week on the good ol’ sofa tucked under the window in the gleaning cherry-wood offices of their lovable shrinks.

I think it’s a great idea. To have someone to sit and listen, to help you reflect on your values, goals, frustrations, fears, and dreams. Someone to ask hard questions about the real stuff. Someone to help you find direction amid a state of otherwise breakneck panic caused by simply existing as a modern-day twenty-something.

Prevention therapy.

Like slipping on a helmet, goggles, and kneepads before skateboarding down this nauseatingly steep hill called the rest of your twenties.

Boozy brunches with your best friend on Sunday afternoons may suffice to some extent, but, come on, are you talking about the real stuff? Or are you non-productively venting about your spirit-breaking day jobs and swapping pictures of your latest Tinder matches? Thought so.

My friendly suggestion? Go turn off your phone, rip out your wifi router, curl up on your own makeshift “shrink sofa” with a laptop or a Moleskin in your lap, and spend the next hour becoming your own therapist.

Mull over the following big ideas, savor each one at a time, take notes, sip your coffee (or red wine), stare out the window, and be alone with your soul.

It’s the least you can do to tune-up and self-service your mental and spiritual health.

1. When do I feel most motivated, inspired, and excited? Why?

2. When do I feel most drained, disillusioned, and frustrated? Why?

3. Do I invest my time and energy in the places, people, and work I actually deem to be my top priorities? If not, how I can reorient myself?

4. Am I able to CHOOSE how I feel? Do I recognize self-defeating behavior and emotions and how can I control them?

5. What are 3 things I can do to live a less self-centered life?

6. What scares me the most? Who intimidates me most? Why?

7. Have I identified my core values? Do I live them out?

8. Am I proud of who I am when no one is watching? Even when I am anonymous, do I embody my character?

9. Who makes me a better person? Why?

10. What would I do with my time and energy if money were no option?

11. What do I take for granted in my life? How can I be more deeply appreciative?

12. What keeps me awake at night?

13. What’s missing from my life right now? How can I get my arms around those things and pull them in tight?

14. What would I like to be recognized for accomplishing in my life so far?

15. Who am I trying to please?

16. Are the things that cause me stress self-imposed? How can I simplify my life to maximize happiness and minimize the stress?

17. What would I do differently if I knew success was the only possible outcome?

18. How does my immediate environment impact me? Can I change or improve the people and places that surround – and shape – me?

19. What is one change I can make that would open the flood gates of my personal happiness and success?

And when you’re done mining yourself for the answers to the above questions, pull out the real bulldozer, take a long sip of that Merlot, and ask yourself:

20. WHY do I do what I do every day, all day long? Do I strive for money, recognition, security, fame, or power?

This last answer might not be pretty, but it’s KEY to understanding your core motivations and steering the ship in another direction if necessary.

Actually, many of these questions are not up for resolution in one afternoon therapy session. They are lifelong musings that center around identifying HOW you want to live, not WHAT you want to do; asking yourself WHO you want to be, not WHAT you want to be. They are heavy weights indeed, and thinking this way requires regular trips to the gym.

Or should we say, regular visits to your new makeshift, self-assessment shrink sofa?