Conquering Uncertainty: An Interview with Jonathan Fields

Follow your dreams. It’s a nice sentiment in principle, but how many of us actually follow through with it? Far too often, we get tied down with a backup plan and our extravagant dream life fades away in favor of the ‘safer’ alternative. But what does it take to actually make the leap into an uncertain future?  What are the qualities a person needs to be able to approach life in that way?

To find out, I recently spoke with Jonathan Fields, whose job description may need the length of its own post. He began his career as a hedge-fund lawyer, but then left his job (and his rather sizable paycheck) to become a personal trainer. After that, he started his own fitness company and opened one of the largest Yoga studios in Manhattan. Most recently, he has become a renowned author, speaker, and marketing consultant, helping others to achieve the same kind of fulfillment that he has in his life. His new book, Uncertainty, was recently released and explores the qualities necessary for someone to stare into a dark and uncertain future and confidently walk right into it. We discussed the book, his interesting career path, and his recommendations for people who are trying to follow their dreams.

You started your career as a highly paid hedge-fund lawyer, but quit to pursue a much less certain path. What allowed you to continue onward when there must have been so much doubt?

Well, there were a few major turning points for me. The first being when I decided to stop practicing law, the second when I signed a lease for a yoga studio on September 10th, 2001. I had to decide in the wake of what had just happened whether or not I was going to continue on, with a wife and a 3 month old baby at home. It’s funny you ask that question because it’s really the genesis of the whole book. I’m someone who has leaned toward entrepreneurship for the better part of my life, but it’s always killed me to a certain extent. There are a lot of people who want to create really cool things. The challenge is taking consistent action when you don’t know what’s coming next, when you are uncertain and when you don’t have all the answers. I think what’s allowed me to be able to do it is that I’ve set up a series of different practices that allow me to reframe scenarios – so I can look at them and know that there’s a lot of risk there, but the downside of not pursuing it in my mind so far outweighs the risk of doing it and potentially succeeding or even failing and recovering. Then it becomes harder and harder to justify not doing it. So when you start to change the questions you ask and you look for different stories to tell – rather than the story of “If you fail” – it gives you the ability to reframe what you’re doing. Instead of paralyzing you and shutting you down, it opens doors for you and gives you the motivation to take action. And the more action you take, with every step forward, it either proves or disproves what you’re trying to do. But it’s those first steps that are the hardest for people to make.

That’s one big thing – the ability to reframe questions. The other is a set of personal practices – mindfulness being at the core – that allows me a baseline level of ‘calm’ and opens up the creative juices in me. So I can go to the place that a lot of people really struggle with.

It’s certainly an admirable quality; it seems that it isn’t something that most people are willing to do.

But it’s not really a quality. The big difference is that if you want to be an artist, or an accountant, or a lawyer or a doctor, you train in that field. But no one really trains in the fundamental mindset skills that allow you to be good in that field. That was the big question of my book – is it something you’re born with, or are there things you can do. One of the discoveries I’ve made is that there are things you can do to make yourself more willing to embrace uncertainty, but no one learns what they are.

With the myriad of different activities you have going on, how do you define your brand?

Well you’re hitting me at an interesting time right now. For a while, it didn’t bother me to think that I didn’t want to be boxed in and wanted to do a ton of other things. But I’m at a place now where I’m getting less and less satisfied telling people I do ‘everything,’ and not having a 5-10 word answer to the question, “What are you building?” And I think that the question, “What are you building?” is a much more interesting question. I think that it’s extraordinarily hard to be really good at something when you are dividing your time amongst five or ten different things. We’re really happy, and there is a fair amount of research supporting this, we are happiest as human beings when we are pursuing mastery in something, when we are really trying to become exceptional at a couple of things. So I’m putting a lot of effort in now to scale back and focus on the things that really interest me, and allocate my energies. Writing about things I really care about, speaking, and to a certain extent eliminating the human condition are the things I’m really trying to focus on now.

Are you finding that it’s working? Are you more satisfied now than you were before?

Yes, but I’m early into that. There are windows in my past where I’ve devoted myself 100% – like when I owned the Yoga Center, that’s all I did – and you become really good at it and it feels amazing. That can be eternally satisfying. For me as a writer, I write not just because I have a message I want to convey, but because I’m really closely tied to a particular topic. I’m really interested in the craft of writing, in the process of writing, to massage language, and have a real meaning behind it. That is an exploration that will take me my whole lifetime to get half decent at. Along the way I get to touch down in a series of different topic areas that really fascinate me and use them as leverage points to make me a better writer, and that’s a cool challenge for me.

When you were first starting out, what were the key elements that helped you to build your brand from scratch?

I hesitate to say there are any universal things, but here is what has worked for me. One is not to listen to people who tell you what is or isn’t right for you, or especially who say you can’t do something. People project their limitations on you. Just because they can’t figure out how to do it, they say you can’t. So kick the tires, figure it out for yourself. That’s the first part. The next part is to spend a lot of time really trying to explore what makes you come alive as an individual. Think about the people, cultures, and settings that you love to be around. Think about the missions that really light you up. And think about the core tasks and processes that when you immerse yourself in them you just feel alive. Make a list with all of those categories. Eventually you will start to come up with qualities that need to be present in any professional endeavor that will make you feel alive. And then don’t look for a particular job or industry, just look for the type of opportunity that will feature those qualities, or as many as you can get.

There’s a question I ask whenever an opportunity comes around and that is: “Will this opportunity allow me the greatest amount of time absorbed in activities and relationships that fill me up while surrounding myself with people who I can’t get enough of and earning enough to live comfortably in the world?” When I apply that standard to the opportunities I take on I’m pretty much always on target, when I do things that fall out of it, I find myself unhappy. People look at my career path and say, “He went from being an entrepreneur to a lawyer to a fitness industry entrepreneur to a yoga industry entrepreneur to a blogger to an author, a speaker, and a marketing consultant,” and they say “Dude you’re all over the place.” But when I look at all of the qualities I lay out for myself, they’re all there. So I’m not limited by an industry or a job, and that opens up a ton of opportunity for me.

Tell me more about the book. What should we expect from it?

The driving force behind writing Uncertainty was that I want to find out what allows certain people to take consistent action in the face of great uncertainty and create great art, great business, and great lives, while so many others seem to become paralyzed or shut down in the face of similar uncertainties. I want to know is this ability genetic or is it something that can be trained. Are there things we can do to be able to mimic or to be able to accomplish on the same level as some of the greatest creators out there? And what I found through a ton of research and interviews was that in fact there are changes you can make. I divide it into three categories. There are things you can do in terms of environmental changes, workflow adaptations, and personal practices that can make a pretty profound difference in your ability to continuously go to that place, and to take action, and bring just amazing creations to life. Not only that, but these three categories are the same things that will allow you to live much more comfortably in a world where there is so much uncertainty every time you wake up in the morning. That’s really what the book is about. I went into the book with a question; I just wanted to know what the answers to all these things were. But by being given access to just some incredibly amazing people, I was able to learn so much. What’s so fun for me is that now I can turn around and digest it and share it.

Many thanks to Jonathan Fields for this interview. His way of looking at the world around him is inspiring, and it demonstrates that the ability to leap into an uncertain future to pursue our dreams is possible for anyone. He also emphasized the importance of exercising and utilizing a strong mindset in order to achieve success in whatever endeavor you are pursuing. We spend far too little time talking about our mind, when in fact it is the single largest contributing factor to either success or a lack of it.

Picture of Bill Connolly

Bill Connolly

Bill Connolly is a marketing/branding expert, career adviser, and professional improv comedian. Bill is also the author of the book, “Funny Business: Build Your Soft Skills Through Comedy” (July 2013), and host of a radio show by the same name on the UR Business Network. He is an actor at Boston's Improv Asylum, and performs regularly with the group What Up D'oh. Bill resides in New York City.

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