Letting Go Is Really Hard

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A few years ago I decided I wanted to get paid to wear t-shirts for a living and promote the companies on those t-shirts via social media. For the most part, that worked out pretty well for me. From January 1, 2009 to May 3, 2013 I was a “professional t-shirt wearer.” I started with myself in 2009. Hired a second shirt wearer in 2010. Then hired four more in 2011 with an additional operations person. Then again four more in 2012 with another operations person. And in 2013 I officially retired, and the company is essentially no more (more on that at the end).

The things I acquired:

Like anybody else, you tend to accumulate things over the years. During my time as a sponsored marketer for nearly 1,600 companies, I accumulated a shirtload of things. (And yes, I mean shirtload, because it was probably 3,000+ shirts during that time). But it wasn’t just shirts. Some companies made really cool branded stuff with my company’s logo on it. Some fellow creative entrepreneurs took time to create completely unique pieces of art featuring my company’s name. Heck, I turned both of the upstairs bedrooms in my average-sized three-bedroom house into an office and storage room for my business (photo below).

The transition:

As I mentioned, earlier this year I officially retired. It was a mix of being completely burnt out and understanding that my business was not in the demand it once was. I’d made changes over the years, for better or worse, that took a huge toll on me. If you could chart my blood pressure since the beginning of the business, it probably looked like a roller coaster ride at Six Flags. My overall health had deteriorated. My inspiration for my company was lacking. And all the while I was holding on to all this stuff. Lots and lots of stuff.

The light bulb moment:

Shortly after hanging up my last sponsored shirt, I attended a little conference in Fargo, ND called Misfit Conf. I was asked to speak at the event, but for the first time in my life, I felt like I’d be a fraud if I gave my normal feel-good story about my company. Instead, I decided to be completely vulnerable to a room of 50 strangers and tell them I was lost. I had built this t-shirt empire. I had poured every ounce of effort into building a business and a community. And I had simply run out of gas. I honestly can’t remember any of my talks, and I usually remember every single word, sentence, and detail. I do remember the last thing I said:

“I don’t know where I’m going to go from here, but you know what, I’m completely okay with that.”

That talk, and all the other amazing talks and people at Misfit Conf, helped me completely let go of all the mental baggage I was holding onto. I had let go of so many emotions and fears that had been bottling up, and it was incredibly freeing. A feeling I hadn’t felt… probably ever before.

Letting go of the physical things:

A few months after that conference I decided it was time to get rid of a ton of the physical reminders of my business. The majority of the things I got rid of didn’t hold much value, but I’d constantly see them in my house. I could feel my blood pressure rising each time I walked into the upstairs “storage” bedroom. Not because they didn’t bring back great memories — they did—but they also brought back the stress. The same thing happened when I sat at my desk in my “office” (the other bedroom) and was surrounded by these reminders. And then I remembered one of the profound things minimalist Joshua Fields Millburn said at that event in Fargo:

“Does this thing add value to my life?”

And as I stared at these things I realized that they didn’t bring me value anymore. Did they at one time? Absolutely. But you have to move on. And so I did. The things I could donate (t-shirts, toys, etc), were boxed up and donated. The things that were more or less branded crap, I threw away (or recycled). And a handful of stuff was sent to fans of my business who would appreciate them.

I recently cancelled the UPS box for my business, which was way harder than it probably should have been. I can’t remember the last time I received a package there, but I didn’t want to let go. There was something about the memories of having that box during the high times of my business that I didn’t want to let go of. I finally bit the bullet and while it sounds silly that canceling a UPS box can be cathartic, it absolute was. (Sorry Brett and crew, who probably won’t read this because you only have an old Dell desktop at the UPS Store and it’s very dusty. But thank you for everything!)

So what’s left to let go of?

The final piece. My office. Even typing this I can feel emotions welling up. I’ve spent well over Malcolm Gladwell’s 10,000 hours in this office. Staring at walls adorned with my company’s URL (for a live video show I spent a huge portion of those hours on), the custom art made for me, and random odds and ends. But it’s time to let go of the last piece of this journey in my life. As of this post, I’ve taken everything off the walls, I’ve put the art in a safe place, and I’m heading to Home Depot to buy a 5-gallon bucket of white paint. It’s time to start fresh and it’s time to let go.

The IWearYourShirt Office

My insanely eclectic, but memory-filled office. I’m ready to move on.

What I’ve learned:

Just because I’m letting go of all this mental and physical baggage doesn’t mean my business has to completely go away. On the contrary. Letting go of all this stuff is helping me focus on a completely new direction for this company. I’m ready for the next chapter. I’m ready to build new memories and to start fresh. Most people don’t get a chance to start fresh on their own terms, and I’m grateful that I get to do that.

Don’t hold on to things because you think you should. Hold on to things because they bring you value every day of your life. You don’t have to go completely minimalist, but it feels so good once you’ve let go of stuff.

What are you holding onto that’s weighing you down? What can you get rid of to help you move forward in life or business? It’s not easy to let go, but trust me, it feels incredible.

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Thanks for taking the time to read this little story. If it’s been helpful for you, I’d love for you to check out my book project. In 2014 I’ll be self-publishing a book called “Creativity For Sale,” with the help of businesses and entrepreneurs. The goal of the book is to give people/companies unique exposure while also helping creative entrepreneurs unleash their inner talents and make a living doing what they love.

This post was originally shared on Medium.

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