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Fail Forward

Fail Forward Smauel Beckett

Before I continue on to my list of things I needed to do to liquidate my life, I need to have an aside…maybe more of a soliloquy…the part of the story where the narrator gives you some insight into what a character is thinking.

A few years ago with a group of friends, I took a strengths finder test that clearly revealed my number one strength. All of my friends got responsible strengths like


I got


“What the heck?” I wondered as I read that people with this strength are usually perceived to have their head in the clouds.

Turns out, I am fascinated by making plans for the future. I anticipate what could be in the future. I need opportunities to talk about every option for the future. I love the inspiration that comes from dreaming out loud about the future. I’m excellent at asking the question, “What if?”

“What if I started an ice cream business?”

“What if I opened a flower shop?”

“What if I bought that old movie theater?”

“What if I took my kids to all fifty states?”

“What if I didn’t make dinner and we just had cereal?”

I’ve been asking the “What if?’ question about a hundred times a day for as long as I can remember. This has served me well, and that question has fueled a lot of memorable adventures in my life.

But something changed in me this past year. After my whole belief system came crashing down, I found myself unable to regain my mental footing. The foundational core beliefs that had held me up and given me such confidence to take the ‘road less traveled by’ throughout my entire life now felt unreliable.

I started to question everything. In an unproductive way.

After a lifetime of stories that started with “What if?”, I found that the content of my questions was different.

Experience had now taught me that I wasn’t as invincible as I had imagined. Depression wasn’t just something other people dealt with in their lives. It wrapped its suffocating tentacles around me, too.

Financial ruin wasn’t something that just happened to irresponsible people. It came for me, too.

Apathy wasn’t just something for people who hadn’t discovered their passion. It crippled me.

The unwavering confidence that had guided my entire life was gone. I felt incapable and found myself riddled with mental chatter that sounded like this:

“What if I’m not smart enough?”

“What if I start one more thing and don’t know how to market it?”

“What if I fail?”

“What if everyone watches me fail?”

“What if I really am just a failure?”

So, in an effort to rekindle the wide-eyed faith and optimism in life that I so fully enjoyed my first 40 years, I’ve needed to tweak my “What if?” question again.

Asking “What if I just try this idea?” turns life into a great big experiment and takes the fear out of failing. After all, I’m just trying it.

“What if I just try finding beautiful fall scenery everyday this month?”

“What if I just try selling my house and traveling the world?”

“What if I try to finish the details of my house on a shoestring budget?”

With that in mind, I will continue the story of this summer.

I do my best thinking with a pen and paper. I have notebooks filled with thoughts, lists, ideas, stuff. I write stuff down. Constantly.

So, after deciding that all of my problems would be solved if I sold my house and had a fresh start, I got my notebook and pen and went to the far end of the house.

I started in my master bedroom and made a detailed list of everything that needed to be done room by room in order to list the house for sale.

The list was long. There were bigger jobs like patching the holes in the walls where I had removed the swanky eighties intercoms and didn’t know how to fix it back then, so I just hung art over them. And little details like touching up paint.

Half an hour later, I had an accurate list of everything I would need to do. I stopped in at the realtor that afternoon and asked for them to give me a market analysis of my house.

I’d be on my way to Portugal in no time.

I wrote out my plans that night and went to sleep with visions of passing the afternoon on a horse ranch in Australia or laughing with my long lost friend from junior high as we reconnected in the rolling hills of North Carolina.

It felt exciting to imagine a future that was wildly different than the last couple of years.

Well, hmmm…you know that story of Jonah and the whale?

It occurred to me about 48 hours into my plan to liquidate my life and travel the world to find myself that I may want to consider the idea that I tend to be a runner. Not literally, of course. I admire those people.

But, it seems that moving every few years as a child has made it very difficult as an adult to just stay where I am. About four years into a place, I get the itchy desire to move and leave whatever monotony may be there and find a new and exciting chapter. On to the next place, the next hobby, the next project.

Except, here’s the thing.

I REALLY love this town. I don’t want to leave this town. Yes, I want to travel and see friends and couch surf for a while, but one of my favorite parts of travel is being able to come home again. Home to the town I love where I drive through the vineyards of Bell Rd to get to the tree-lined street of Zimri just to go to the grocery store.

I love it in the spring. I love it in the summer. I love it in the fall. And I love that the winter is short. This is the place I want to call home until the last curtain falls, and I graciously step into life’s mysterious epilogue.

So, 48 hours after deciding to leave my problems in Newberg, I climbed up on top of my roof to watch the sunset through the trees. I reminded myself how much I love those trees and found myself wondering just for a moment, “What if, now that I’m feeling better, I try to really throw myself into action and dig myself out of this mess I’ve created?”

Meh. That didn’t sound nearly as fun as driving a convertible through the French countryside.

But in asking the question, my newly energized mind turned my focus to figuring out HOW to keep my house, HOW to pay my bills, HOW to start a new chapter that adds people and connection and the fun I’ve been missing.

So, instead of liquidating my life and running away from the total discomfort of having some ominous mountains to conquer, I stood on top of the roof as my colorful backyard slipped into darkness and loudly proclaimed to no one in particular and the whole world in general,

”I’m baaaack, and I can do this thing!”

And that’s when the magic of the last 5 weeks started to unfold.

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