I wrote a letter to my younger self. It was during an exercise that I use to help women over 50+ (including me!) see how far they have come, how much they have learned, and to help clarify where they want to go from here. But it was powerful. It was eye-opening. And it helped me to see just a little more clearly that putting in the work is worth it. That making a conscious effort to choose more in your second act is worth it. So, what can you learn by writing a letter to your younger self? I’m so glad you asked…
How to Write a Letter to Your Younger Self
Write a letter to the younger version of you. If you need ideas on what I mean, you can read mine farther down in this post. What would you reassure “younger you” about, with the knowledge you have now? What do you see clearly now that she could not?
Write down 3 times in your life you stayed quiet or small. How would you handle that situation now? What do you still want to change about that answer?

Learning to Say No
Here’s the thing, oftentimes we think we are saying yes out of love. And sometimes, that is true. But can you look back and see times in your life when you said yes, even though it wasn’t best for you, just because you were afraid of the other person’s reaction? I know I have, more times than I can count. Writing a letter to my younger self really helped shine a light on that. 🤔
Practice saying no with kindness. You don’t have to turn into a heartless troll in order to say no. For instance, if someone asks you to head a committee that you don’t have time for, try “I so appreciate you asking, but that would just be spreading myself too thin, and I am trying to take better care of myself. I’m sure you understand.” Simple, to the point, and accurate, without any bad feelings. But it takes practice. Have a couple of scripts like this memorized so you are ready when you need them. Try it for one small thing this week.
Remember, it isn’t selfish to take care of yourself. And if that voice in your head tells you to keep giving when you have nothing left to give, talk back and tell it that the very least you deserve is to have your needs count as equal to anyone else’s.

Learn to Forgive Yourself
I live (and will probably die) by a quote from Maya Angelo… Paraphrasing, “We do the best we can until we know better. And when we know better, we do better.”
There are so many times in my life I made decisions I wish I could take back now, but that is not the way this ride works, ladies. I did the best I could at the time. Now I forgive myself, knowing that we all carry these mistakes, because it’s human. Learn from it, then let it go. Check out my post How to Forgive Yourself for Past Mistakes for more ideas. When you learn how to write a letter to your younger self, this topic will likely poke its ugly nose out. It’s ok. We all have regrets. It’s time to deal with them and move on.
Baby Steps in Reinvention
Crazy we’re in midlife+ and talking about baby steps, yes? But that’s what offering yourself grace is all about. You don’t have to have all the answers. Just make it a habit to make small, brave steps towards who you want to be moving forward.
- Wear the outfit you love, even if it gets the attention of everyone in the room. (With your chin up!)
- Try something outside your comfort zone. I was the wallflower at school dances. I’m taking dance lessons. In my living room. Online. But I’m doing it!
- Speak up for yourself for one thing that you want. Do you always just go along with the restaurant pick? Does “I don’t care, any place you want to go…” sound familiar? (My hand is up!) This time, choose a new place you’ve been wanting to try, even if your partner isn’t as keen. Don’t worry, you aren’t going to suddenly be this demanding monster. Just try it, every once in a while. And see how it feels.
Start an Everyday Bucket List
I’m not talking about planning a trip to Europe, or climbing a mountain. (Though those are great too!) I’m talking about making a list of new experiences that you can try in your everyday life to help you move forward. Maybe things you were afraid to try in your past? Try to commit to trying one new thing each month. Ideas?
- Go to a restaurant alone and enjoy the view. (Throw in a glass of wine and slice of cheesecake for me!)
- Ask a friend out to lunch.
- Volunteer one day a week.
- Learn to play piano.
- Make it a habit to complement other women.
- Join a gym, book club, or hobby group.
- Start a business.
- Go back to school.
Getting it? Every experience moving forward builds your self-esteem and your self-confidence. And every experience from your past helps you to identify who you want to be. Remember girls, like I always say…
We. Are. Not. Done.
-Kathy
Keep scrolling to read my letter to my younger self!

My Letter to My Younger Self
Dear Younger Me,
I see you, sweet Kate. I see you as a young woman, making decisions based on who you believe you are supposed to be. On what society tells you that you are supposed to be. Allowing other people’s needs to come before your own. Being afraid to admit to mistakes because you might disappoint the people you love. Being so loving and loyal, but then making yourself small to keep the peace. Making yourself the responsible one in relationships to protect those who don’t deserve protection. Career decisions based on all the wrong things. Accepting unacceptable behavior from others because “that’s just the way it is.” You are sidestepping your own dreams, walking on eggshells in relationships, making yourself less, to make others more. You are a people pleaser, always seeking validation from those around you. Afraid to speak up, to stand up, to do what you need to do.
In some ways, I think you don’t even know how amazing you are. How much you are capable of. I think you are so tied to the opinions of others that you are afraid to step away. To fly. The world clipped your wings, and you are going right along with it. You don’t make waves.
But Kate, I want you to know it won’t stay like this. It will take time, and it will take making so many mistakes, but you will find your way. Not overnight. Not all at once. It will come slowly. But it will come.
Every experience you have will impart just a little more wisdom. A little more confidence. And then one day, you will stand up for something big. Something that matters to you. And then you will stand for another. And another. You will be inspired by other women who will give you just enough courage to finally say no to something that is hurting you. You will find strength inside yourself that you didn’t know you had.
You will start over, more than once. You will learn that relationships aren’t obligations, that real love is a two-way street, and that dreams never die if you don’t let them. You will learn that bravery is something you can choose, not something you are necessarily born with. And you will learn that you matter. That it isn’t selfish to put yourself first for a change. To be true to yourself and who you want to be.
And Kate, you will find the real you. The one who has always been there, but was too afraid to take that risk, end that relationship, start that business, reach those goals, start over… She is there. And every day you move forward, you are looking for her. You are following her quietly, waiting for the day when you will meet. And when you start to get to know her, you will learn to recognize that every choice, every mistake, is a part of who you are. That your scars make you stronger. That forgiving her is a process, but offering her grace and love is the only way through it. You will learn that all of it was part of your journey, and that guilt has no place in your life. She will help you move forward, a little more every day.
You will start your second act with so many insecurities, but you will find it is actually this part of your life that offers you the most growth. Where you start to realize that the only person you need to impress is yourself. That you finally feel that it’s your time. And as you move into this part of your life, you will find people who you connect with based on your values. You will have the wisdom to seek help when you need it, and to stand tall when you don’t. You will realize that getting a do-over isn’t a one-time thing; you can have as many as you need. And you will learn to be as gentle with yourself as you would be with your granddaughters.
I am so glad we are meeting in the middle, Kate. We have so much to talk about.
With Much Love,
Older and Wiser Me
PS: Keep standing up for what you believe in. Make decisions based on what’s right for you. Keep saying yes to joy. The best parts of life are still ahead.
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You might want to check out my posts,
Journal Ideas for Women Over 50+
Fun Midlife Confidence Vibe Quiz!
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