The Overthinker’s Guide to Pivoting

When I left the financial industry to work in partnerships at Mindvalley, it was done on a complete whim. My reasoning, however, was clear: I loved personal development and wanted to be surrounded by people who also loved personal development.

When I left Mindvalley to run an online business for a year, it was also done a whim. I was curious to learn more about this new type of business that could exist simply based off of your personal brand.

When I joined Shopify, it was the whimiest of whims. I had just moved back to Ottawa and although I didn’t really know what the company did, I knew there were about 800 people in Ottawa who were really passionate about entrepreneurship.

They felt like whims at the time, but looking back on all three career pivots, there was something similar about all of them. It was like time slowed down, the colours around me became brighter, and I had this eery feeling that future-me would look back and kick herself for having let the opportunity pass by.

I call it following my curiosities, but we can just as easily label it intuition.

In our early 20’s, we don’t have much external pressure yet and our intuition is able to guide us easier. As we get older and as fake timelines start bubbling up, so does our overthinking. There’s a moment in all of our lives where we start to feel like we need to have life figured out, and pursuing a pivot in our life or career feels like a sign to the world that we don’t know what we’re doing.

For those of us who are multi-passionates? Pivots will always be a part of our life. There will be no “arriving”, only continuous experimentation and growth.

Our intuition, like our metabolism, seems to go down the drain as we get older. Instead of trusting it, we start second guessing every impulse and overthinking the smallest decisions. What will people think? How will I pay my bills? What if I want to buy a house?

What helps me is getting very well acquainted with how my intuition speaks to me. That feeling I described earlier of time freezing and my senses becoming more aware. And then to actually take steps towards it? I remind myself there’s always going to be an awkward transition phase during a pivot. It won’t feel good or clear. The discomfort we feel isn’t a reflection of our capabilities, but a necessary step in the process. (I’ve written about The Awkward Transition Phase before — it’s a quick read and might be helpful if you’re currently in this phase. I know I am!)

Back in March, when the pandemic first started, Shopify went into full blown “save the entrepreneurs” mode. I’ll be honest, I felt pretty useless compared to the developers who were writing code and stretching Shopify into an even more powerful beast. So when the Shopify Compass team asked if I wanted to host one webinar to help them out during their quick and scrappy launch in March, I was eager to help. Being “out of my job scope” didn’t matter to me, and while it was a little extra work, it was also… fun! 

And then? I was offered the opportunity to become a regular weekly host. I still remember that moment: time slowed down, the colours became brighter, and I had this eery feeling that future-me would look back and kick herself for having let the opportunity pass by.

This was going to be extra work and I didn’t know how it fit in to my career, but it felt good and I said yes. Six months in, I can feel something brewing… a pre-pivot energy bubbling inside me. It feels like a coil getting tighter and tighter and then, eventually, it will shoot out into a new direction. I don’t know what that pivot will be, but I have a feeling that the skills I’ve been learning with the webinars have been a prerequisite for it.

It’s exciting, but it’s also one of the hardest phases to be in. I want to get to the other side, but I also can’t rush it. Every day, my logical brain is trying to control it by coming up with a new grand idea, a new project, a new pursuit, a new anything to get rid of this in-between feeling. And every day, I am telling my brain to chill out and stop overthinking — that my next step is currently being built and I simply need to show up and make the most of each day.

So this week, I’ve been soaking up the experience of hosting Eva Chen, the VP of Fashion Partnerships at Instagram, on Shopify Compass. Diving deep into her story, I’ve discovered that she is truly the definition of a multi-hyphenate career woman. (If you want to be inspired, search her on iTunes and binge-listen to her podcast interviews!)

Something that stuck out for me was when she described modern careers as the moving staircases from Harry Potter. I love this comparison. It’s such a great visual to juxtapose the traditional career ladder: one is stable with a clear path carved out for you, and the other one is non-replicable. You might be mid-climb on a staircase and it moves to a new landing.

It reminded me that no one else has my career background. And I’m guessing, no one else has your career background, either. We are never starting over, we are simply building on what’s already in our backpack. And your backpack with all its prized possessions is what makes you irreplaceable. We need to embrace that more.

‘Do Things On a Whim” might feel like the advice I’m giving today, and it partially is, but I also want to share two practical skills that create a support net for when you’re in a transition phase (ie. when your crazy overthinking brain comes out).

First, remember that your next step is being built and trust that the universe will do a better job than you on this.

Second, remember that opportunities flow through people. It’s why making the most of your current situation is so important. Someone in your life currently or someone new who may enter it, is holding an important clue for you. It might be a comment they make, an experience they share, or if you’ve been ignoring these clues for a while it might be a full on opportunity handed to you on a silver platter. We need to be curious with the world and get out of our own heads.

When we get a new idea, it’s like we immediately want to burn our current life to the ground and start over. Trust me, I’ve felt this. But allowing space for many parts of ourselves to co-exist is where the magic happens.

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