A Love Letter To My Past Self

An exercise in reflection and gratitude for creative entrepreneurs

When was the last time you paused to reflect on how far you’ve come in your creative business? 

If you’re anything like me, it’s probably been a while. 

It’s natural to get swept up in the flurry of daily activity that comes with the territory of running your own business. You likely take for granted: 

  • The complex work you do because at this point it’s second nature! 
  • Or the detailed,  industry-specific information you know like the back of your hand.

But chances are that didn’t happen overnight. 

You probably poured tons of time, energy, sweat, and maybe even a few tears into building your business from the ground up. All while continuing to refine your creative skills, connect with your audience, and develop your offers.

So, don’t you think that warrants some celebration?

I’m taking time this week to reflect on my own journey, and I invite you to do the same. As an avid, lifelong journaler, reflection through writing has always been a helpful way for me to process things in both my personal and professional life. However, this journaling prompt stands out to me because it’s a little bit different. 

It’s a love letter from me to my past self. 

I’m sharing my love letter with you in hopes that it inspires you to pause, reflect, and thank yourself for everything you’re endured, created, and experienced leading up to this very moment.

Without further adieu….

Let’s jump in!

A Letter From Me to My Past Self

Dear Erin,

I can still picture you, clear as day, in my mind’s eye:

A bright-eyed, 20-something version of myself, early in your career.

You were fresh out of art school at RISD and ready to take on The Big Apple! When I reflect back, I see you, seated across from an important-looking man at a conference table that felt legions long. With vast windows behind him revealing the sprawling NYC skyline, he told you what a huge opportunity you had stepped into.

You didn’t know if he was right or wrong, but the possibilities were equally as exciting and nerve-wracking!

He encouraged you saying, 

“This is where they tell you to fake it ‘til you make it” 

But instead of feeling more confident, his well-meaning advice left you with a big lump of imposter syndrome sitting in your throat…

((and truth be told present-day-Erin doesn’t quite subscribe to that advice, BUT it did push you to show up and speak up long before you felt ready or qualified enough))

…so the entire walk out of that meeting and back to the subway you hummed that old Frank Sinatra song to yourself like a soothing lullaby,

“If I can make it there, I’ll make it anywhere. It’s up to you, New York….”

To this day, that song instantly takes me back to the NYC design office and that pivotal moment in time.

A time when you accomplished so much, but often at a cost. 

Your anxiety was at an all-time high, pushing you to deliver above and beyond, keeping you up at night while you double, triple-checked that every box was ticked and every “i” was dotted.

You did SO good.


If I could go back in time I’d tell you….

  • Breathe. As Marie Forleo says, all things are figureoutable and nothing is as serious as it may seem in the heat of the moment.

  • Seek out a therapist to help you realize it wasn’t NORMAL or NECESSARY to always feel wound so tight.

  • Remember: “Done is better than perfect.”

  • I’m so PROUD of you for seeking out the resources you did: trying pilates, taking daily walks, and confiding in trusted friends as you slowly but surely figured out this whole “work/life balance” thing. 

Thank you for…

I see you working hard and want to say thanks for…

  • Putting in the long hours, and doing it scared.

  • Persevering and pushing up against your perfectionist tendencies while embracing the fact that not everything can or will be perfect (no matter how hard you try)

  • Developing the skills that allow me to thrive today.

  • Being brave, trying new things, and never playing small.

  • The non-work stuff too! Like…showing up on that blind date (because who the heck lets their aunt set them up with her co-worker from Philly and actually thinks it’ll work out?!) Spoiler alert: It does!!! And it leads you to the love of your life and two beautiful, amazing, feisty kids!

  • Showing up for and betting on yourself every single time. Because you are worth it and I’m reaping the rewards of it to this day!

My promise to YOU…

I promise to…

Keep showing up for myself so the future me can write present me a love letter just like this someday from an even better perspective and vantage point. 

A place where I’ve accomplished some of those goals I’m working towards today. 

A place where I find myself closer to the lofty goals I’ve set (and that you’ve taught me to believe in). 

A place where I’m striving for even bigger goals than I ever thought possible!

So, cheers to us. Past, present, and future.

Your Love Letter

Gentle Reader,

::Yes, alllll the Bridgerton Vibes::

I hope you’ll take some time to reflect back and write your own love letter to your past self (this is a great use for that CEO time you’ve been meaning to carve out)

Feel free to use my structure as a guide or let inspiration lead the way. I found this to be a wonderful exercise in gratitude, but it also helped me clarify my goals, my why, and my mission in both my personal and professional life. 

Looking for more journaling prompts and inspiration for your creative business? 

Check out these past blog posts:

  1. YEAR-END CELEBRATION (because really, you can, and IMO should celebrate any time, not just at the end of the year)
  2. SCARY GOOD TIPS FOR BATTLING BURNOUT (Scroll down to check out Alex Banya’s 30-Day Challenge)
  3. HOW TO MAKE A VISION BOARD TO BUILD YOUR DREAM BUSINESS IN 5 EASY STEPS (This blog is jam-packed with journaling prompts as you set your vision)

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