Breaking Free from ‘Should’: How I Discovered Ease, Joy, and Connection

Have you ever found yourself wondering, is this all there is to life? More or less the same day on repeat, marked by small moments of joy, snippets of silence and brief respite from the constant pull to do and be more. You countdown to the weekend, look forward to a new season and wait for the phase to pass, as if one day your dreams will arrive on your doorstep. As if someone could purchase ease and grace, simplicity and joy, connection and meaning online and ship them to you as a gift. 

Like everything in life, there’s no one path, no singular route, no 'Buy Now' button that delivers the life of your dreams to your door step. The truth and I argue the beautiful reality, is that creating the life you dream of is entirely your responsibility. No one is going to do it for you. You’re not going to wake up one day thinking “you know, I have some free time today, I think today is finally the day I decide to [be the parent I want to be] [move where I’ve always wanted to live] [quit my soul-draining job]”. Nope. You have to consciously choose, among the demands, to-do lists and chaos of daily life that today is the day. 

For me that day came when I finally chose to stand up to the voice of 'should'. My voice of should had gotten so loud that I felt no joy in the things that are inherently joyful. I was seeing friends, calling family, cooking dinner, doing yard work, playing with children, walking the dog, cleaning the house, journaling – all because I felt like I should. My inner voice of should took the joy out of just about everything. 

My curiosity in letting go of that voice began as a walk around the neighborhood. I started by checking things out, making observations and enjoying the scenery, knowing that I could turn and go home at any point. But then something incredible happened. My unassuming, leisurely walk around the neighborhood led me to a sense of freedom I never knew existed. No part of me wanted to turn back; my walk turned into a trek around the world. A trek I’m still on, one I may never choose to stop because the surprises and delights, meaning and joy are just too good. 

The stops and sights, people and smells and tastes are far more grand, beautiful and joyful than I’d ever imagined. The more I trek the more I find myself aligning to the person I’ve always wanted to be. The more I feel comfortable showing up imperfectly. The more I understand the magic of faith and the power of vulnerability. The more I learn to be present and connected to the people, life and things that matter most to me. The more deeply I connect with joy.

Seeing friends, calling family, and stirring dinner are all joyful now. So are clean underwear, green lights and pennies on the sidewalk. Navigating life feels easy because I’m learning to live for myself instead of the voice in my head. I’m learning to let go of the stories and beliefs that no longer serve me.

I’m also learning to let go of stuff. 

My memory tells me that it started with my Barbie Doll collection. The one that took up three full size totes in my basement. I felt so much joy in purchasing and renovating my first home; letting my creativity run wild as I mapped out the best way to design and organize my spaces. No need to ask permission to paint, contend with poor lighting or useless closets. At 98 years old, my home was a blank canvas in my eyes and I was the artist. But as I got to work, there were some things I simply couldn’t make sense of. Like my Barbies. Obsessed with maximizing every square inch of space for function, I couldn’t figure out how on earth to make sense of three totes of Barbies. 

I couldn’t possibly get rid of them, could I? After all these years of staying disciplined, keeping them properly stored, safe in their boxes? How would my Granny feel knowing I got rid of my Barbies? The ones she so intentionally bought me every Christmas until I turned 18. What if they were worth money one day? What if I had a daughter one day? Would I let her take them out of the box? Vintage Barbies would be cool… AND, the cold hard truth was that they brought me absolutely no joy.

So not unlike my curiosity with what it would be like to let go of 'should', I decided to experiment with letting go of my Barbies. First I checked eBay to see if they had any value. Guess what, not only were they valued at a measly $40 each, but there were literally dozens available. Sure, I could in theory make $720 if I sold them all, but here’s the thing – with dozens to choose from, why would someone choose my 1993 Barbie over the next? How long would it really take me to sell them all, keeping in mind that I had to store the damn things until that day came? 

Gently reminding myself of the magic I’d found in letting go of my 'shoulds', I took the next step and posted my least favorite Barbies to my local Buy Nothing Facebook group. I felt comfort in knowing that if any part of me missed them, I could always buy a replacement for $40. But guess what, my neighbors were delighted by my offer and I was SO relieved! It didn’t take long before I posted the whole dang bunch. My Barbies were going to daughters and granddaughters, friends and cousins, even grown adults looking to continue building their own childhood collection. 

I wont lie, the part of me that was growing to understand the freedom in letting go felt kinda yucky giving people more sh*t that I knew they didn’t need either. But I also understood that we’re all on our own timelines, our own personal journey, and clearly they weren’t ready to start their trek just yet. 

18 Barbies down, I started to look at my other belongings. Did I need a blender that I used twice a year? What about two sets of measuring cups? Why did I have 13 dog towels? Could I ever use 13 dog towels at once? What if my basement flooded and I needed towels? Why was I making decisions based on 'what ifs' that may never become a reality?

Was I really honestly ever going to wear that pair of shoes from 2012? When was the last time I wore them anyway? Hmm, 2013. Even if they came back in style one day, would the joy of being able to wear them again bring me more happiness than the weight of holding onto them for decades? NOT. ONE. SINGLE. BIT. 

What about the cards from my 7th birthday? Did any part of me care who attended my 7th birthday? Would I ever one day look back and feel so emotionally moved in reading those cards that I could justify holding onto them for decades? Nuh uh. 

And that’s more or less where I’m at today. I still have to consciously choose to challenge the voices in my head. I’ve more or less let go of the voice of should, but that’s only created space for other voices to come to surface. So each day I wake up and choose to challenge those new voices.

I’ve let go of anything excess and am now more or less on a journey of maintaining what I have. I set strong and clear boundaries with myself, with my partner, with my loved ones. Bringing something new into our home almost always means letting go of something else. Occasionally I feel the urge to push myself even further into minimalism – do I really need 11 sweaters when I only wear the same 5?

But to take us back to where we first started, it’s never really been about the stuff in the first place. It’s about life and meaning, happiness and joy. Owning less means I don’t spend precious and limited time managing stuff. When something is out of place, I know exactly where it goes. I don’t have to contend with the distraction of clutter, of all the 'extra'. I don’t feel overwhelmed by laundry or dishes, decorating for the holidays or swapping out clothes for the season. I have what I need and I know exactly where everything is. Sometimes I misplace my phone, or my keys, but never for long. 

When someone comes over I don’t have to feel any certain kind of way. I clean the toilet and make sure the guest bed has clean sheets. I don’t apologize that I didn’t vacuum or have no plans to feed them a five course meal. Olivia five years ago would have fallen over unconscious reading this, so fixated on everything I should do to ensure I was a 'good hostess'. Nope. I’m done with that. The best and greatest gift I can give anyone who walks into my home is the gift of time. The gift of presence. The gift of connection. 

That’s the promise that awaits you in letting go. In letting go of everything that stands in the way of more happiness, ease and joy. In letting go of all the things, beliefs and voices holding you back from the dream life that often feel so distant. 

So the question now becomes, what are you waiting for? What dreams do you have on hold for the weekend, the next season or a new phase of life? How long are you willing to wait and at what cost? Whether you start with the Barbies, the voice in your head, the clothes in your closet or the clutter on your counter is of no importance. All that matters is that you choose a direction and start walking. See where it takes you. You can always turn around, but I’m placing bets – you’ll want to keep going. 

Ready to say yes? Hold yourself accountable by commenting where you plan to start and when. I’ll follow up with a reply! Ready to start but not sure you want to go alone? Let me know, it would be a true gift and honor to walk beside you. 

With love and light,