Farewell 20s, Hello 30s

3 Reflection Exercises for entering a new season of life

Christine Chapman
5 min readAug 22, 2022

This week I turned 30! 🥳 It’s not the most important moment of my life, but it has felt like a huge milestone. In the lead up to this week, I spent a lot of time reflecting.

  • What would I miss about my twenties?
  • How would my life be different in my thirties?
  • What milestones for my career and personal life have I already achieved
  • What did I expect to have achieved by this point?

There are many things I’ve achieved that I am tremendously proud of (surviving college, becoming a manager, staying in tech for 8 years and counting, buying a home), but there are many things I have not. Many of my friends are married with children by now and it can feel like I’m falling behind.

As I reflected, I found myself focusing on three exercises that helped me look backwards and forwards and arrive at a place of peace and even excitement about this new decade. I am on my own timeline and so are my friends. I realized how much I had grown and changed in my twenties and I expect by thirties will bring similar growth.

Whether you are turning 30 this year or entering a new era of your career or personal life, here are three exercises to prepare for the next stage.

Looking Ahead: Current Me vs. Future Me

In 2019, I started using the Artist of Life planning method created by Lavendaire.

One of my favorite exercises from the book is called Current Me/Future Me. On one side of a piece of paper you write traits of your current self and on the other side you write traits you aspire to have. There’s no set timeline, each current trait doesn’t need to have a better version you aspire to. It’s merely stating how you perceive yourself now and who you want to become.

I recently reread my Current Me/ Future Me entry from 2019 and reflected on Future Me from 2019 vs. Current me in 2022.

Hopes from 2019 that I achieved:

  • Still focused on improvement → Always.
  • Great manager, inspiring, confident, supportive — I’ve now been a manager for 3.5 years and even started managing 2 teams at my new company.
  • Say no to 3 trips this year. More time at home → Bestie, I hate to tell you this…

Goals I didn’t achieve:

  • Run 3 miles a week, run a 5K race → I have no interest in doing this anymore. Plans change. :)
  • Completed draft of a novel and shared with friends → Wrote 3 more drafts and I regularly post on my blog and newsletter. So even though I haven’t yet shared the drafts, I think I’ve achieved the spirit of it.
  • Be in control of the time spent on my phone → Work in Progress, but I am more aware now.
  • Optimistic in many things → I’ll give myself a pass on this one. Maybe in 2025. :)
  • Closer to family and friends → Despite the pandemic affecting physical proximity to my friends, I am more in touch with my long-distance friends and my family than I was back then.
  • Moved out of my apartment → Last year I moved into my own place!

Try it: Take out a piece of paper, draw a line vertically down the middle. On one side write “Current Me” and on the other side write “Future Me”. Add at least 20 bullet points.

Then store it in a safe place and return to it in a few years. You’ll be surprised how you’ve grown and changed. You can even use a site like futureme.org to automatically email you this list at a specified date in the futuere.

Looking Back: Write Younger You A Letter

As you’re entering a new era, it can be helpful to reflect on the beginning of this era, whether that is a decade ago, the start of college, the start of your career, etc.

Write a letter to the younger you at the beginning of the era you are now ending. Here’s one I wrote.

Dear 20 year old Christine,

In the next decade, you will graduate, move to Boston, battle mental health issues, and identity issues. You will mature, grow, and change. You will come out on the other side a leader, a confident professional, and a compassionate manager. But while your methods, approaches, and passions will shift, your ideas and values are just as good right now as they will be then. Don’t doubt yourself and certainly don’t let others doubt you. You are a force and I admire that. There are many days when I wish I was you, but I had to give up some of what made us great to persist. But just because I did give it up, doesn’t mean we were wrong to have cared about it from the start. Keep on being you. You are amazing.

Love, 29 year old Christine

Reflecting on the now: Journaling Prompts

Commit to 1 journaling prompt a day for 7 days or a whole month. In the lead up to my birthday, I did 30 days to 30.

Example prompts:

  • What is something I find myself learning over and over?
  • What is something that I do regularly that younger me would be proud of?
  • When I was [age] what did I imagine my life would look like by now?
  • What aspects of my dream life are within reach today?
  • How can I celebrate everything I have done so far?
  • How have my beliefs and values shifted in the last few years?
  • What changes do I want to invite into my life?
  • What do I want to let go of?
  • What quotes or lyrics or mantras have been resonating with me lately?
  • What fears do I have about entering this new era of my life?
  • What are my top priorities in life right now? How have these shifted the last few years?

There is something so powerful about giving yourself the space to journal out your thoughts without judgement. It’s great to look back at old journal entries, but even in the present it can bring healing, spark creativity, and renew your focus. Even if you have never taken up journaling, try out this exercise for seven days. Pick a time at the beginning or end of your day where you’ll have the time. You might be surprised what you learn about yourself.

Beginnings and ends inspire reflection and we should honor that. But remember, you are capable of changing at any point in your life. Not just in these big moments. As always, you have the power to change your story. Happy reflecting!

If you liked this resource check out Changing the Story for more resources about tech.

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