Some Days, I Take a Leap

If you looked at my life as a whole, you would have to conclude I am pretty risk-averse. I mean, I’m a lawyer, after all. For the better part of two decades, I’ve literally been in charge of mitigating risk. All sorts of risk. Head mistress of risk, if you will.

However, you would also see a solid streak of daring. Rebellion. Bold moves that would test the mettle of even the wildest of sorts.

I guess I’ve always been a bit of both.  Wild-hearted and responsible.  Logical and luminous.  A pragmatic, unrealistic dreamer. There’s a method to my madness. But, that madness makes me, well, me.

What I’ve learned in all my contradiction is there’s such a thing as risk-mitigated risk-taking and it’s the practice that has allowed me to thrive in the tension and take leaps.

In almost every circumstance the urge to leap arose, the stakes were high. And they kept on rising as the years passed. As the stakes got higher, I grew more cautious. High school was one thing. But, then, college. College was another thing. But, then, law school. And so it went. The decisions and choices of my life grew more fraught as I increasingly had more to lose and, paradoxically, questioned myself more and more. The daring part of me never went away, though. It just got harder and harder for her to win out. Yet, I knew deep down how important it was to honor her. So, I went from taking running, flying leaps to walking myself reluctantly all the way out to the edge and giving myself a push. In each case, I went through three critical steps.

Defining the Dream.  At the outset, it is important to get really clear about what it is that you want to do.  Define it in detail.  Equally important and in equally as much detail, why do you want it?  Why is it important to you?  What does it mean to you?  What does you look like and feel in that future state?  Why does that feel right to you?

Defining the Risk.  Then, dig into the risk in the context of the dream, the broader landscape and the other risks and alternatives. In analyzing risk, it is important to ground yourself in the magnitude and the probability of the risk. What is the worst thing that could happen if you go for it? Don’t hold back or be afraid to go deep here. Think through the entire parade of horribles and take each to their most anxiety-provoking conclusions. In doing this, be sure not to omit the risks of not going for it or the risks of the possible alternatives. They’re often overlooked, yet imperative to consider. Then, ask yourself, what is the likelihood of each of the various scenarios? And, critically, are there factors that make those scenarios more or less likely? 

Taking the Edge Off.  Once you have fully absorbed what the leap could mean for you and the associated risk landscape, then ask yourself what you could change around the edges. There’s almost always going to be a tweak you can make that would mitigate some of the risk or empower you to think about it a different way. The thing to keep in mind is, despite the importance of clearly defining your vision, it is equally important to maintain flexibility. Dig beneath the detail and consider where there might be room for critical movement or refinement. Stay true to the purpose and what you’ve learned about your why, though not necessarily to each tangible detail of that first sketch of the vision.

I have been through this cycle many times and these frames have helped me have the courage and conviction for my journey.

I fell in love with New York when interviewing for my first job after law school, despite knowing no one in the city, never having spent meaningful time there and having already set in motion plans to live in LA near my family. In an impulsive moment fueled by curiosity and possibility, I’d accepted a callback in New York over the firm’s other more logical choices of offices. And I indulgently let myself swoon as I sat in the yellow cab and watched the mythical skyline come into view. The energy was palpable even then, and only continued to surge as I walked through the city streets and into the offices that would someday be mine. When I ultimately made the move to New York, having no real reason to be there outside of work, I opted to work with a firm that had offices in LA as well as in my hometown (and many other places around the world). A transfer wasn’t a given (heck, I didn’t even know if I’d ever want one), but it felt like just enough of a safety net to make that leap less risky and easier to talk myself into.

I met my partner in London while studying abroad. We dated briefly, broke up so I could focus on studying, dated again, decided not to try dating long-distance when I moved home and stayed friends. After several years with romance simmering beneath the surface of friendship, we decided to give long-distance a try after all. Very soon after that, he moved internationally to be with me and live together. Given the limited time we’d actually spent together over the prior four years of knowing each other and the atypical nature of our courtship, the odds would say there was a very good chance of it not working out. But, both of us felt strongly it was worth taking a chance to see if there was really something there. It all felt very romantic and also very impractical. And, perhaps it was, in ideation. But, ultimately, he was able to find a compelling reason to come to New York for work and, rather than finding a larger apartment and uprooting my life as I knew it right away, we decided to have him move in to my status quo. Worst case, he would have a valuable professional experience and we would know we had given it a try.

The magical thing about approaching things this way is that, sometimes, the dreams come into being all on their own (or seemingly so). It’s like you put that energy into the universe by exploring the vision and the universe presents you with an option you hadn’t considered. Maybe an option you never would have believed existed. But, that alone won’t get you there. You also have to have the tools to make the attendant risks manageable and get yourself comfortable taking leaps.

I grew up drawing dresses, writing poems, and crafting stories in my head. I was told that a career dedicated to any one of those dreams was extremely risky and pretty much certain to fail. Sure, some people made it but it was rare. One in a million. A needle in a haystack. (I know now that this is not entirely accurate, but that was the water I was swimming in…) So, I ultimately went a completely different direction:  Law. However, I was always me and my passions came through, drawing me to clients in the consumer brand space and in fashion, arts and entertainment. Once I quieted the lingering narrative and the doubt and fear it had fostered, I was able to allow space for my vision to take shape and, from there, much was simply doing the next right thing.

Each step in the direction of my passions somehow led me to where I am today:  Law, in-house, in fashion, where storytelling is paramount and creativity is existential. So much so, that I have found writing again. While it sometimes feels like everything just worked out the way it was supposed to, it is also true that the opportunities that presented themselves required considerable leaps and much intentionality. I walked away from the possibility of partnership, despite giving my all to my law firm for over eight years. I made the change at a time when retail was inherently uncertain (at best), my company even more so. I was clear enough in my passion, though, that I knew I would regret not pursuing the rare opportunity before me. And, even in these seemingly fixed circumstances with so many variables out of my hands, I found ways to take the edge off – employment agreement, timing of giving notice, clarity on the ROI even in a worst-case scenario – and leap.

Ironically, building this muscle in risk-mitigated risk-taking in my personal life has helped me hone it in my professional life. I often tell my business partners that my job is not to eliminate risk – that’s impossible. Everything comes with risk and the risk of doing nothing is sometimes far greater than doing the thing I’m being asked to evaluate. I explain that my job is really to help them evaluate risk in context and come up with creative solutions to manage it in a way that is appropriate for the situation. The frames above are the same ones I use in business and they are the foundation of how I’ve been able to help my partners find creative solutions to their most challenging problems and scenarios. Coaching them to take the leap all the while mitigating risk in a way that’s appropriate for the situation. And, in a virtuous cycle, each time I flex this muscle professionally, it fuels my strength to leap personally.

Recently, I heard Ed Catmull, co-founder of Pixar, speak on risk and risk tolerance, noting “Ratatouille” and “Up” don’t seem at first glance like clear runaway successes based on their atypical storylines. He noted that considering something that’s risky at the outset is different than that risky idea being the thing that’s at the end state. Risk isn’t a permanent thing, it’s something you’re going to work on. There may be problems but the creativity is in solving the problems. This captures the idea well and speaks to its broad applicability.

Ultimately, I believe there’s always a way to pursue your dreams, big and small, no matter how bold and risky they might seem at first. In my own life, in each case, these tools have enabled me to narrow the risk to a reasonable level I was comfortable assuming and then take the leap.

I haven’t looked back.

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