I’ve got thirty days left in my twenties. That means I probably am not going to ever make it onto a 30 under 30 list, or publish a book before thirty, or get married and have *at least* two kids before thirty (lol childhood goals). And I know I’m being facetious. Like those things are definitely not going to happen.
But … I like myself so much more than I did ten years ago – or even one year ago. I’ve learned so much more about how to take care of myself and the people I love. I learned that doing things I love and leaning into my interests would give me more professional success than making “safe” and “smart” choices. I have survived through some really hard times, personally and in my family. And for the first time in a long time, I am actually excited for a birthday. I’m really not thinking about what I didn’t accomplish in this year or this decade, I’m thinking about how many good things are ahead of me.
When my friend Helen was going to turn twenty in college, she made a bucket list for things she wanted to do her last week as a teenager. We did shots of sour apple liquor, climbed a tree, put on crazy make up at Boots (British Drug Store), sang karaoke, went to a toga party, and did at home face masks. I’ve been thinking for a bit if I could come up with my own bucket list for my twenties, but instead I came up with a different bucket list: Thirty Questions I want to really ask myself and journal about this month. Here’s what I came up with:
- What is my definition of unconditional love?
- What are some things I wish everyone knew about me?
- What ten words would I use to describe myself?
- Who are the people I admire most? What do I admire about them?
- What ten things have happened in my twenties that I hope I never forget?
- What ten things have happened in my twenties that I hope I never repeat?
- What do I know I want to say no to?
- What do I know I want to say yes to?
- What do I feel guilty about? What do I feel shame about?
- What books have meant the most to me?
- What has surprised me most about my life?
- What do I know for sure? (The Oprah Winfrey Question)
- What are my biggest fears?
- What places have I visited that mean the most to me?
- What do I wish I could tell my mom and dad?
- What am I most proud of?
- What things do I want to stop worrying about?
- What are my favorite words?
- What are the best pieces of advice I’ve ever received?
- How have I changed most in the last five years?
- What am I unkind to myself about?
- Who have been my biggest teachers?
- If I spent a day just trying to make myself happy, how would I spend the day?
- Who do I love the most and how do I show them love?
- What do I want to learn more about?
- What one habit do I want to cultivate most?
- What feelings do I avoid feeling?
- What do I wish I could make peace with?
- What goals are most important to me?
- What am I grateful for?
Alison Doherty 
I’m watching 13 going on 30 as I read this, appropriately enough. I always ask what my younger self would think of where I am now, and I bet your younger self would be really proud of you.
Aww Betsy, thank you so much. I don’t think my younger self could even imagine being this okay with myself. Like it would have completely blown my mind that I didn’t have to be anxious all the time. But I’m proud of my younger self, so I like the idea that she would be proud of me now.
Also very solid movie choice. Thirty and flirty and THRIVING!
Alison, you’ve done in your twenties what so much of us had hoped to do: grow into yourself beautifully! Your 30 questions are superb for every decade, I think, and far more insightful than most at your age. The excellent news is that you’ve learned so much and you have so much more time being young to really enjoy yourself. Congratulations and happy early birthday!! xoxo
Thank you Patrice. That is so kind!
I love this idea! What a great way to spark some interesting inner noodling. I hit 35 in November, and I’m thinking I should do something similar. Happy early birthday!