The Art of Getting Unstuck: But how did I get here? (origin story)

Spring, 2016. Hong Kong harborfront, walk with Anisa.

Spring 2016. I’m on a business trip to Hong Kong. Before I left my home in Singapore, a friend offered to introduce me to someone who could change my life. Um, yes, please!

When I met Anisa on the harborfront, her first question was “why do you think your friend sent you to me?” From the little I knew about her, I guessed I wasn’t there for cultural tips or to do an ice plunge. Instead, she could offer what I’d probably call, now that I know her, modern spiritual guidance.

“Well, I am about to leave Singapore, and I’m trying to decide where to live, and I have all these options…” She let me go on and on about my choices, how overwhelmed I was, and my weighting system (I still have the spreadsheet if you want to see it… but trust me, you don’t).

When I paused for breath, she gently interrupted my meanderings. “It seems like you are creating complexity for yourself. Tell me how you want to FEEL in your new city.”

As I tried to answer, I realized I didn’t have the words to articulate how I wanted to feel… or even more fundamentally, to pinpoint how I wanted to feel. She realized that too and asked me instead about a place I felt amazing in. When I described the mix of contentment and inspiration I felt sitting by the lake at my parents’ summer house, she instructed me to remember that sensation. “When you visit these cities you’re talking about, see if you can match that feeling. Let me know how it goes.”

Reader, it did not go well. To give myself credit, I did actually feel the feeling, but then I let my brain override it and pick another city. A city that served up a sinking feeling as I drove in. “This isn’t your place,” I remember my body so clearly telling me (and my mind echoed the sentiment: sure, NOW it was on board). But I was committed. I had a new job and a new apartment. All my stuff was on a ship from Singapore, bound for this city.

I stayed for four years in that wrong city before I got up the gumption to move again.

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I’ve been addicted to a TED talk by philosopher Ruth Chang for years. In it, she defines a hard decision in a way that blows my mind: a hard decision is one in which more than one choice can be right, but for very different reasons. That’s why they’re hard.

Of the 9.6m views of her video, I’m probably responsible for 712 of them.

And yet, with hard decision after hard decision (what city to move to, what job to take, etc.), even though I knew thanks to Ruth what I was experiencing, I still didn’t know how to make these turning points any less angsty and awful.

Winter, 2022. Turning the design process on myself.

Winter 2022. I was looking to move again and determined to have a different experience. I had time on my side, but also very few constraints, thanks to the pandemic putting all my work online. While that may sound freeing, constraints are actually a good thing, helping us hone in on relevant options more easily.

I knew that because I’d spent more than a decade as a design leader, helping corporation after corporation to reinvent their products, their services, even themselves. The lack of constraints was a clue: this hard decision was a design opportunity. I decided to turn my design skills inwards and use them to reinvent the experience of choosing.

In one of those ahh “this is where it’s all been leading” moments in life, I drew on everything I’d learned over my life and my career: how to design delightful experiences, the science of behavior change, what mindfulness practice teaches us about navigating liminality, how somatics (the practice of listening to the body) can ground us, how to date well (yes, I promise it fits!), and what it feels like to make big moves (of all kinds, geographical, career, and relationship).

And reader, it worked! I type this from my new home, feeling very much content with my choice. But also, I really enjoyed the whole process of getting from there to here. The process I created, with all the seemingly disconnected wisdom I had gained over the years, took something painful and made it fun!

What did I choose and how exactly did I get here? If you’ve been following my instagram stories, you know the answer to the first one: I’ve chosen to have a dual-town life, spending about seven or eight months a year in Florida, and four to five months a year in Maine. And how did I get here? Well, you’ll have to follow along for that. I’ll keep sharing more of my story as I continue this series of blog posts.

After I reinvented this decision-making experience, I giddily told my friends how different I felt this time versus all the other times. As it turned out, several of them were asking similar questions, and they prodded me to offer a workshop. A workshop turned into private coaching and friends turned into friends of friends… now I coach all kinds of people (couples, individuals, people who have all their stuff in storage waiting for what’s next, people who have already moved and are second-guessing, etc.) through the same process I took myself through. (Well, actually a better process, as I keep refining it!).

But beyond that, as you know if you have attended any of my offsites or read my post The Art of Getting Unstuck, I realized that hard decisions like Where is Home? when you can live anywhere are simply us getting stuck… and there are other ways we get stuck, too (decisions, desires, and derivations are the top three… more on that soon). So, now I use design to help people get unstuck on what matters most to them.

Someday, maybe I’ll share all this in a TED talk of my own. Until then, how can I help you?

The original workshop that evolved into The Art of Getting Unstuck.