How to Part Ways With Past Versions of Yourself with Kindness

One of my favorite parts of being a planner person is looking back on planners from the past. I often chuckle to myself as I read reflections on challenges that, in the moment, seemed like a catastrophe and are now only a blip in the rearview mirror. Admittedly, there are also times when I experience a bit of envy for previous-me. The me at that weight. The me who got all those job interviews. The me without my present worries. Then there’s the total opposite: experiencing the intense cringe over past mistakes. (Does anyone else randomly shudder at the thought of our teenage years?)

As we near the end of the year, I think we’re all collectively shedding some skin from 2024. And some of us–I daresay probably most of us–are still shedding skin from years long before this one. In this blog, I want to explore, with as much grace and humanity as possible, the ways we can give our past selves a farewell worthy of a friend.

1. Remove the Rose Colored Glasses

If envy of your past self is slithering into your heart, consider that even at your “best,” it was likely not always “the best.” Those rose-colored memories can sometimes gloss over the struggles and insecurities we faced back then. Maybe you were thriving in certain areas but suffering silently in others. Remind yourself that every chapter has its challenges, even if, in hindsight, they feel like the happy ending of a movie.

Reflection Questions

• For what specific chapters of my life am I wearing rose-colored glasses?
• How am I putting my past self on a pedestal? 
• What challenges did I face during the “best moments of my life”? 
• How can I better humanize this version of myself?  

2. They Did The Best With What They Had

Feeling disappointment or regret towards your past self is also valid. That said, I am a big believer in this cliche saying: you did the best with what you had. Though simple, this perspective requires a ridiculous amount of compassion that challenges even the best of us. Did I really do my best? I’d also like to specify this: you can believe you did your best and understand that accountability is necessary. One of the best living examples I have of that is a man I met recently who started a nonprofit for recovering addicts. He said, “If I hadn’t had compassion for the man I was before, I would never have the compassion necessary to be here for these people today.” Be kind to past-you. Because past-you might be present-someone-else.

Reflection Questions

• Which versions of my past self need the most kindness?
• Do I believe I did my best? Why or why not?
• If I met my past self today, what would I tell them? What did they need to hear? 
• How can I use my past experiences to help or guide others?
• Who is an example of someone I admire who used their past for good?

3. It’s Only Goodbye for Now (If You Want It To Be)

The notion that we leave our past selves forever is far from the truth. If this were the case, none of us would be in therapy or having ongoing discussions about our inner child. They visit, sometimes more often or for longer than we’d like. Or we give in to nostalgia and want them to linger. I get that feeling sometimes. I drive by my childhood town to see that everything has changed: my former haunts have gone out of business, the city feels like it’s lost some of its character despite newer painted plazas, and, well, I realize I’m twice the age of my sixteen-year-old self. Perhaps our past selves are inviting us to satiate a yearning that’s gone unfilled or to relearn a lesson we once thought we had mastered. 

Reflection Questions

• What do you think about most when you give in to nostalgia? 
• Who is the past self you’ve been running into the most often? How do you engage with them?
• What values, passions, or dreams from your past do you miss most? 
• In what ways can you reintroduce those elements into your life now?
• What experiences are you ready to let go of permanently? 

4. Savor the Gift of the Present

“Yesterday is history, tomorrow is a mystery, and today is a gift. That's why they call it the present.” Master Oogway and Eleanor Roosevelt had it right. Our past selves deserve lots of love, but never at the expense of who we are today. I find it exciting to think about the fun memories I still have ahead of me, and humbling to know that there’s a whole curriculum of lessons life is waiting for me to graduate to. My hope for you is that when you feel the breath in your lungs, no matter how your day or life is going, you’ll know with all your being that life has more joy, wonder, and love in store for you. 

Reflection Questions

• What are three things in your life right now that bring you joy or peace? 
• How does being present feel in your body? What helps you tune in? 
• What memories from this chapter, big or small, will future-you savor most?
• Who are you most grateful for in this moment? Why? 
• What experiences and resources do you have today that past-you wished they had?
• What daily routines or habits help you connect with the present?  

Moving Forward Doesn’t Mean Forgetting

Moving forward doesn’t have to mean starting over and leaving your past self behind completely. Each version of you has shaped who you are today and carries valuable lessons, memories, and growth. By honoring your past with compassion, you’re free to embrace the future with clarity and intention. It’s okay to hold space for where you’ve been, while focusing on where you’re going. 

For more tips and encouragement along the way, follow Passion Planner on Instagram.

AUTHOR BIO

Paula Palomar is a Digital Marketing Copywriter who loves using words to uplift the messaging of mission-driven companies and organizations. In her spare time, you’ll find her practicing yoga or eating churros at Disneyland.