“If I were to realize that door A, B, or C all lead to a lot of heartache and pain, but you know, A was what I really want, well, why not just choose A?” –Mike Herrera, founder of MxPx (via Ryan Holiday)

Last week we wrapped up another intake of the Career Change Accelerator at Escape The City. I rewarded myself the next morning in the simple way I often do: walk to a local cafe with a good book, my trusty notebook, and order a big tasty omelette with a strong cup of coffee.

As I sipped the coffee, I carefully teared open and read the thank you note from the latest cohort and paged through the notebook they gifted me. Then had a teary moment to myself as I reflected on how wildly my life has changed in the last 6 years.

If you’d told me 6 years ago I’d be making a living doing work that’s both purposeful and enjoyable; that I’d be working with interesting people I both like and respect; that I’d be paid well while living the life of flexibility and adventure I desired; that I’d see firsthand how my work is impacting people through their tears and laughter – I’d have smacked you silly.

Yet that’s exactly what I hoped for myself 6 years ago. The problem was I didn’t know the details — i.e. it would involve facilitating, teaching, writing, speaking, presenting, acting (?!) and helping people pursue more meaningful work — nor did I know where to start figuring out the details.

So I began the only way I knew how, using one of the basic tools I had access to: my imagination.

In particular, I put my imagination to work with one exercise in particular; one that kickstarted my whole current trajectory:

Writing (freehand) my “Ideal Day.”

What Does Your Ideal Day Look Like?

I asked myself: From the moment I wake up until the moment I go to sleep — what does my ideal day in the future look like?

I took a blank page from my work notebook and started writing.

I didn’t know many of the details, so I just made something up, based on what sounded amazing and exciting:

“I wake up feeling well rested and invigorated. I make a strong cup of coffee and walk outside to stand in the sun and admire the natural world outside my window and porch. I’m in a foreign, beautiful place. The temperature is perfect. The sun warms my face. I page through a global newspaper like Wall Street Journal and a local newspaper in a local language to get a feel for the headlines and news of the day. Then I cook myself a hearty, healthy and colorful breakfast, usually consisting of eggs…”

My natural tendency is to try and think of the best answers first before starting to write. But as I discovered with my Morning Pages journaling and writing in general – that NEVER works. Instead I’ve learned to treat my mind like a blocked gutter. Writing – not thinking – gets the gunk out. My truest answers flow and deepest dreams become known only after I begin the writing of them.

When it came time to write about my work day and career…I drew a blank. So instead of details, I wrote the flavors – the types of activities and the kind of places and people I’d like to be around.

“I have a full day of exciting projects lined up, and I’m eager to get started. I’m working beside kind, smart people I both admire and respect, doing work that has deep personal meaning to me and has a positive impact on the people it touches.”

Was it perfect? No. It was a shitty first draft. So I continued to revise it over the next several months and years. For one version, I even recorded myself reading it into my phone and would listen to myself while making breakfast or taking a walk.

6 Years Later

Here I am, 6 years later. And guess what? Much of what I wrote has come true. Not all of it. And much of my life looks different than I could have imagined. I also still have tons of room to grow as I continue to double down on what I’ve discovered about myself and my work.

But especially now, this week, as some exciting opportunities are finally coalescing, here are two reflections.

Me. 6 Years ago. Reykjavik, Iceland.

Reflection #1:  SIX YEARS.

Do you know how long 6 years is? Part of me is embarrassed it’s taken me so long. But also – this is how long this shit takes. Always longer than you want it to.

Reflection #2: Every Year Has Felt Like The Best Year

It hasn’t been all bad between year 0–6. In fact, every year between then and now has felt like the best year of my life. Even though I was not quite where I wanted to be, I had begun to craft a life deliberately vs drifting regretfully. I was on a fucking adventure. I WAS ALIVE! Which included highs as well as lows. That was rewarding enough.

Through it all, I’ve tried to embrace my ambitions, whilst not hanging my future happiness on the success of those ambitions. Like the wisdom found in Zorba The Greek:

“This is true happiness: to have no ambition and to work like a horse as if you had every ambition. To live far from men, not to need them and yet to love them. To have the stars above, the land to your left and the sea to your right and to realize of a sudden that in your heart, life has accomplished its final miracle: it has become a fairy tale.”

Hugh Macleod, Gaping Void

Your Turn.

If you’re not happy in your work or life, and feel you have more to give to the world and discover about yourself — you can make a change. And you can begin it simply: start today and write your tomorrow.

Write your future story. Write the wildest and most remarkable life you can imagine. Write something your future self will thank you for.

Everything is waiting for you. It might take 6 years. But if you put it out there and begin it, it might just come true.


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