Hi, I'm Jon.

I'm a digital nomad, traveling around the world while working full-time as a founder, engineer, and activist. I document my work, thoughts, and discoveries here.

Being Brave

Being Brave

Every year, for a few years now, my friends and I have practiced this exercise in lieu of resolutions: we come up with three words that serve as themes we set out for the rest of the year. Goal-based resolutions like losing ten pounds or to get a promotion have always felt flat and one-dimensional to me. Instead, by having these three words, you can use them as signposts to help you make decisions with more intention throughout the year or even the rest of your life. This past January, the person who’d introduced me to this exercise Alexa and I were going through our words for 2018 over dinner. These were mine:

“Steadfast” I had said. I want to be more persistent and work on building habits that would be resilient to the natural change of my life. I want to build stamina. Between traveling, my career, and my social life, trying to find some constants to anchor my life has historically been a challenge. Taking care of my body, staying creative every day, tending to my relationships…these are all things I want to be more regular about. I want some things in my life to become as inevitable as the sun rising and setting each day.

“Expression” was another word. I feel like I have work — thoughts, ideas, feelings — hiding inside of me that isn’t visible to the world. I keep things in more than I’d like. In other words, I feel like I haven’t been authentic to myself: who I am on the outside doesn’t fully feel like who I am on the inside. How do I be the person I want to be in a way that others can see? Do I dress the way I want others to see me? Do I make my thoughts known to others, in my writing and in what I say? This is less about making sure other people know what I feel, think, and believe and more about being less shy to express myself, for me. How do I present myself to the world in a way that is true to myself, regardless of who will see me?

But there’s one word that was on my mind leading up to this dinner and the word I’ve been thinking the most about this year: bravery. Now halfway through the year, it’s what I want to write about today: what it means to be brave.

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I think from the outside looking in, a lot of people don’t think I have trouble doing what seems outlandish, intense, or scary. I came out as gay when I was 14. I’ve picked up and traveled the world while working full time as a nomad for several years. In the past, I’ve committed myself fully to a hard, improbable romance for a long period of time. I’ve started plenty of ambitious, tricky projects professionally and in my volunteer work that can go sideways at any time. Risk is something baked into everyone’s lives, but I’ve managed to sprinkle my life with a pinch or two more of danger. To understand why, there are three things to know about how I make decisions.

First, when I’m confronted with weighing an opportunity, I default to doing the exciting, vital thing. Sure, I’ll go on that weekend trip with you. Yes, I’ll buy tickets for that festival. Why not help you start this pet venture of yours? There are a few justifications at arm’s reach for this default. There’s the clichéd carpe diem response “You only live once.” Something else I remember pretty vividly is the advice “You miss all the shots you don’t take.” There’s a sea of platitudes I could draw from, but in the end, I think I’m just built this way. Unless I find a good reason not to do something, I’ll tend to just go for it. For me, taking action pulls me in like gravity: it takes a lot of effort to escape it.

Second, even though I’m working with a default that spurs me to action, I’m always thinking about how to minimize risk. If something requires some consideration, I’ll do everything I can to minimize what seems dangerous: lowering the stakes mentally, preparing for things ahead of time, building an encyclopedic knowledge about what I’m about to attempt. A big part of this process is breaking these problems down, and it’s a skill I think can be taught. Take traveling the world for three months while working full time, something I first considered years ago. Becoming a nomad was a daunting possibility. After several months of mulling on the idea, I was able to turn that possibility into just a few essential questions:

  1. What do I do about my apartment? Can I rent it out to pay for my travel?
  2. Where do I want to go? How do I go to and stay in each place?
  3. How do I work with my team remotely? What do I need to broadcast about my working habits? What about Internet?
  4. What do I need to pack? What can I buy along the way?

Each of those questions were sizable in their own right, but I could figure each out with some work. Suddenly, the big question “should I travel the world for three months while I work” became much less frightening. After some meticulous planning, going nomadic became an exciting adventure, one that I relished as I went through it. The same thing goes for starting a new creative project, tackling a complicated recipe for a dinner party, or even going onstage to give a talk. Those things seem like exciting opportunities with some mitigation. “Think of the realistic worst possible scenario,” a mentor had once told me. “If you think about it carefully and believe you can recover from it, go for it. You have nothing to lose.”

Third and lastly, I’ll bail when it’s sensible. With everything I’ve explained before, you might be tempted to jump to the conclusion that I believe you can do anything. I’m not saying that all risky things aren’t really risky, just that there’s a way to make really exciting opportunities more approachable. There are some stupid things you just shouldn’t do, and some failures you really can’t recover from. After breaking the problems down, seriously considering them, and weighing the cost and benefits, some crazy things really are just crazy—so don’t do them. The method here just makes the field of possibility a little wider in life.

So why is one of my words for 2018 “bravery”?

With these three things put together — a mental default to action, knowing how to break big decisions down, and having some perspective about when to quit — I feel like I’ve managed to open up a lot of opportunity in my life that I wouldn’t have had otherwise. This philosophy has helped me in my career, my social life, and my personal growth. But there is one problem. No matter how much planning, rationalizing, and considering I do, there is still one thing that I can’t control for, something that I think has limited me for most of my life:



I don’t think I do very well with fear. There are a handful of horror movies I’ve actually watched beginning-to-end. I never learned to ride a bike as a kid because I was nervous of falling and embarrassing myself. I ended up wearing glasses most of my teenage years because the idea of putting lenses in my eyes scared me senseless. To this day, I get squeamish being around little children with balloon animals because I’m terrified their squeaky toy will pop right next to me. You get the idea.

You see, my entire philosophy around decision making and taking on risk is about minimizing fear, and that’s because I’m terrible at getting through fear. Did coming out at such a young age scare me? Yes, of course it did. So I made every preparation, considered every scenario, and set everything up just the way I wanted it so that when I was ready to come out, it didn’t feel like such a heavy lift. Did the possibility of packing my life into a backpack to explore an unfamiliar world shake my bones? Yes, it absolutely did. So I studied and planned and worked to make sure everything was in order so the excitement of traveling to new places would overcome my anxiety of the unknown. So much of my energy and my time goes into thinking about how to minimize risk and fear in my life because making big leaps of faith is not something I am very comfortable doing...at all. My inability to engage with fear directly has motivated me to minimize it and ultimately avoid it at almost any expense.

For the most part, this approach has been fruitful. It’s taught me really valuable skills and opened up a lot of doors along the way. But the other edge of the sword cuts in such a way that there are some opportunities — no matter how much planning, studying, or calculating I do — that I choose to pass on. Why? It’s not because I don’t want to take the opportunity. It’s not because I haven’t been able to break something down. It’s not even a bad idea to take the leap after all that consideration. It’s because I simply can’t get through the fear that remains after all that work.

These decisions and opportunities are big and small and range from the life-changing to the ordinary. I can’t tell you how many crushes I’ve let go of simply because I was too afraid to admit my feelings — they’re opportunities that might have turned into really meaningful relationships. Starting my own company in earnest, with funding and people I’m responsible for and real customers I serve, has never really happened because I am afraid I will fail, even if I might have a better chance than most at succeeding. What I’m describing is the kind of fear that holds me back from opportunities, many times big opportunities, that I have every reason to take. It’s the kind of fear that you can’t minimize, that is big-by-design, and that you have to get through instead of around.

I’m tired of letting those opportunities pass me by.


For me, being brave isn’t about dispelling or minimizing fear like I have been — it’s about being terrified and doing what I set out to do anyways. I think that starts with understanding what I’m scared of. I’m learning that my fear is just a way for my body to tell me something: that I am afraid of losing something that matters to me in a way that I can’t control. I’m learning that once I understand what it is that I stand to lose and once I can let go of the control I feel like I need to have, I can move past my doubt. If I treat my fear as a tool and not as my enemy, perhaps I can do the things that have always made me quake.

Now halfway through the year, I find myself drawn to the things that have terrified me and doing what I want to do in spite of the dread that stills my heart. I look at my fear like a challenge now. Being brave is about having courage, and the thing about courage is that it’s like a muscle. It only gets stronger with use, with failure, and with recovery. I’m taking on the things that are risky and calculated and still failing, so that I am less afraid of failing the next time. I’m speaking up more for what I believe in when I am afraid of what people will think of me. I’m getting better at apologizing, when I’ve been hesitant to take responsibility before. I want to tell my would-be crushes that I want to go on that first date. I want to make new friends in unfamiliar places. I finally want to learn how to ride a bike.

I’ve been putting off exercising my courage my whole my life. In fact, I’ve done everything in my power to avoid being brave, without even knowing that’s what I’ve been doing. Now that I do, it’s finally time to flex.

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