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21 Questions

December 29, 2017

1. What makes me feel wide awake even when I’m lacking sleep?

When someone I care about needs help. It doesn’t matter if it’s 3am, I’m instantly awake and fully present. What do they need? How can I make them feel better?

2. What makes me feel exhausted, even when I’m perfectly well rested?


3. In twenty years, how will I look back on this period in my life?

I’ll tell myself I shouldn’t have worried so much, that I shouldn’t have been so careful, that I should have taken more risks because nothing was nearly as big of a deal as I made it out to be. I’ll realize that nobody was talking about me and my choices because they were too busy worried about theirs. 

4. What is something I’ve always wanted to do, but haven’t yet?

Start a business. Sell something I made.

5. What advice would my ten-year-old self give me?

Trust your instincts. You don’t need to be scared. Go for it. 

6. If someone I look up to took over my life, what major changes would they make?

Force me to choose a path and take action. Make me fail to see it’s not so bad.

7. What have I always admired, but assumed I wasn’t naturally talented enough to try?

Public speaking. 

8. Why do I assume other people can be wildly successful, but I can’t be?

They grew up believing in themselves.

9. Which trait do all of the people I look up to have in common?

Action despite fear.

10. In which ways do I self-sabotage and why?

Look for everything that could go wrong. Believe I can’t make a wrong decision. Because failure isn’t an option.

11. If I died today, what would be my biggest regret?

That I never put any of my business plans into action.

12. When do I feel most attractive?

When I’m myself around others… goofy, sure of myself, confident, don’t care what others think.

13. When do I feel least attractive?

When I second guess everything I say and do. When I feel not good enough and small. 

14. Which feelings am I constantly running away from in life?

“They’ll think I’m stupid.”

15. What might those feelings tell me about myself if I stopped and actually listened to them?

I’m valuing others opinions over my own, even though I’m the only one that knows what’s right for me. 

16. What makes me incredibly angry, and what core fear is that anger protecting me from?

Complaining without action. Pretending you’re powerless. If you don’t like your life, change it. I’m afraid I’ll always be stuck and not good enough? I’m afraid I’ll be the person I can’t stand?

17. A year from now, what would I like my life to look like?

Free, purposeful, full, healthy. Have my own business, live downtown, pursuing creative projects, strong boundaries.

18. What is something I can start doing today that would make my life radically different in a year?

Speak up. 

19. Which major mistakes have I seen others make that I never want to make myself?

They didn’t act. They didn’t start the thing. They let fear win. 

20. What makes me feel scared?


21. What might I find on the other side of that fear?


Taken from 50 Questions That Will Help You Find Your Way in Life When You’re Lost. I know, I know. These types of posts typically make me cringe, too, but I guess given that this is the season of reflection and resolution, I found it timely.

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