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The Year of Working With Extraordinary People

Every year around December, I try to summarize my year into one sentence that captures an overarching theme that has contributed to many areas of my life. The year 2015 was The Year of Working with Extraordinary People.

2014 was the year of earning my degree, refining my craft, and branching out in my freelancing work. I enjoyed all three, but at the end of 2014, there was a twist. Instead of pursuing freelancing, I realized I wanted to be part of something bigger than just myself, a place where I could contribute my skills as well as learn and grow from others. I didn’t know what working at a start-up would be like—New Jersey doesn’t have the kind of start-up culture or mentality that Boston, Singapore, or Silicon Valley do, and I only had a fraction of an idea of what a writer at a start-up would do based on the sites I read. I asked my editor, Sean, at 99u to help me untangle this messy decision, and by the end of the next day he showed me a door and I walked through it.

I joined a wonderful company called Help Scout. There, I’m part of a team, I have an excellent editor, coworkers-turned-friends who give invaluable feedback, a manager who challenges and nurtures me, and a CEO who isn’t the traditional kind of CEO but one who embodies values that make me believe great leaders exist. My craft is consistently being refined, I’m learning the various components of a company and how they work, and I truly, deeply enjoy all of it.

Mid-2015, I was asked to be an inaugural coach for Seth Godin’s altMBA online program. I was the coach for a cohort of students, responsible for providing feedback on their projects, nudging them forward, inspiring them, and helping them grow. Aside from writing, this became a new favorite kind of work—connecting with people, engaging with them vulnerably and empathetically, providing feedback on their projects, watching them fail, watching them grow, and because of this, lead more meaningful lives. Our alumni are wonderful.

I’ve just rebranded and redesigned my site, with an entirely new focus, promise, and goal. My work was on one notable site in 2014—now I have to use two hands to count.

All of this—every achievement, every opportunity, every hard lesson learned—was because of the people around me. I didn’t achieve these things out of sheer merit; rather, I had the fortune of being surrounded by incredibly talented human beings who have connections, skills, and knowledge. Aside from their talent, they embody attitudes and values that set them up for success.

For my own benefit as well as theirs, I wanted to write these out loud and clear so that from here on, I can be a joy to work with for someone else.

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Coaches training for altMBA3—a diverse group of ruckusmakers from all corners of the world coming together.

Here are five noticeable traits of these extraordinary people.


“The first step to living wisely,” admonished the Stoic philosopher Epictetus, “is to relinquish self-conceit.”

In short, don’t act like a know-it-all. This is a common trait across every person I’ve worked with. It’s actually so profound that I have to acknowledge it to myself how well these people empathize with different points of view or when someone spots a flaw in their idea. They’re true professionals.

No matter what, they are focused on doing the work better and improving the quality of the project or endeavor. There’s no ego or backlash. “Oh, you have an interesting point—okay, let’s try something else,” they might say. And we adapt quickly, make new decisions, and move on. Boom—simple.

One time it happened so quickly in front of me that I burst out a in mixture of a laugh and a cough and said, “So that’s it? The problem is fixed? We understand?”

“Yep,” they said. “Time to do the work.”


Brené Brown, in Daring Greatly, defined vulnerability as possessing uncertainty, risk, and emotional exposure. It is also the most powerful catalyst for love, connection, and belonging.

My designer interviewed me before we committed to doing work together. I was completely vulnerable because I knew it would help her understand me, my brand, and my goals. She reciprocated and a connection ensued. We didn’t delay on shipping or thrash on the project because we both had that level of understanding one another—no ego, passionate about the work, honest communication, and more. I looked forward to our meetings because they weren’t like traditional meetings—it was a place where work got done and decisions were made.

My theory is that this is why great work and great connections were created through my year: vulnerability was lifeblood. The people I enjoyed working with all expressed vulnerability—not like “here’s my darkest secret”—but showed up honestly and without judgment.

Vulnerability is some of the hardest work we do because it’s a choice we make. Do we choose to tell the truth when we look someone in the eye? Do we choose to communicate clearly and honestly? Do we choose to show up wholeheartedly?

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The marketing team at Help Scout

Imagine you had to look a student in the eye and say, “Honestly, you missed the mark on this. I think you can do better.” This happened a lot in my coaching work, and at times I would sweat because the experience was so raw, but going through that changed me; it made me more mature, empathetic, and understanding. All the right intentions for helping the student succeed were there, but it was the risk that made me sweat, physically and emotionally. I could have said a million other things, but choosing vulnerability ended up working well, no matter how much I doubted that it wouldn’t.


The way Audrey Hepburn adored Tiffany’s in Breakfast at Tiffany’s, I adore people who love their craft.

People who genuinely love what they do throw their self into their craft. They desire not so much perfection, but rather a quality of excellence that elicits awe and makes them proud of the outcome and honored by being able to live the process. It is a source of deep meaning and fulfillment because they provide value that enriches the lives of others. It shows in their work, their thinking, and the language they use.

These are the best people to work with and be around. There’s no questioning the small things like, “Will they get it done well and on time?” These are pros. They never get comfortable with their level of expertise; in fact, they constantly learn new things, refine, and remove the excess. They’re hard on themselves, too, because they care about quality. They’re meticulous, often ruthless with attention to detail, and they double and sometimes triple-check even the smallest things. They’re inspiring creatures, and I often wish I could borrow their talents and their ways of seeing, communicating, and deciding. I am starry-eyed when I am around them.


The extraordinary people I’ve worked with exude empathy. Maybe it starts with their eyes, or their body language, or the way they listen. They really step outside of themselves, enter into another perspective, and live there for a moment. Whether I saw empathy in action with a customer, a student, or a peer, it made me appreciate its power of connecting people, resolving differences, and fostering a deeper understanding of human nature. I almost wanted to call this year the year of empathy, but to me that felt self-serving—empathetic people are extraordinary.

And the great thing is, empathy, while some of us are more sensitive to it than others, is ultimately a decision—a decision to engage another point of view and acknowledge the power of one’s own hidden biases. It’s a conscious decision that understanding, rather than being right, is a far more rewarding endeavor.

“If only they knew what I knew,” we say to ourselves. Can you write an essay on agreeing with your opponent’s point of view? Can you agree to the worldview of why your customer would go to your competitor? Can you write an essay agreeing with the reader who thought your essay was awful and that no one should ever subscribe to your blog?  If you think writing is hard work, trying writing that.


As Sam Harris said in Lying,

Honesty is a gift we give to others. It is also a source of power and an engine of simplicity. Knowing that we will attempt to tell the truth, whatever the circumstances, leaves us with little to prepare for. We can simply be ourselves. In committing to be honest with everyone, we commit to avoiding a wide range of long-term problems, but at the cost of occasional, short-term discomfort. However, the discomfort should not be exaggerated: You can be honest and kind, because your purpose in telling the truth is not to offend people: You simply want them to have the information you have, and would want to have if you were in their position.

It sounds so simple, but like vulnerability, it’s hard work. Honesty is live art.

Perhaps the prerequisites of vulnerability and empathy are powerful enough to enforce honesty, to make it natural or effortless. The extraordinary people I work with are bloody honest. They want me to have the information that they would want if they were in my position. They overcome short-term discomfort by focusing on the long-term pleasure. They’ve given me a gift, and I hope to reciprocate that at every available opportunity.


The saying goes that you are the five people you surround yourself with. I always rolled my eyes at that maxim, not because it’s untrue, but because that’s what we do with wisdom. We roll our eyes like a teenager and then experience life. Sometimes we’ll muster the humility to admit that it was true all along, and that we should have made wiser decisions with who we hung out with on weekends when we were younger. But it’s not in our control to determine when or how we experience certain things in life that teach us the lessons we need. Sometimes they come to us, sometimes we run into them, and sometimes we have to chase after them.

I don’t know what luck came my way that I should be so fortunate to work with great people, but my goodness, I ain’t complaining. What an opportunity to learn from it, to take everything I can to enrich my creative soul and stretch my mind. I look at their successes and paths and say, No wonder, look at who you are as a human being. It’s great to reaffirm that they weren’t born that way but became that way.

When I was writing this, a dot appeared in my mind, and I had to dig into my commonplace book to find its connection. I did find it: the Roman emperor Marcus Aurelius said the following:

“When you need encouragement, think of the qualities the people around you have: this one’s energy, that one’s modesty, another’s generosity, and so on. Nothing is as encouraging as when virtues are visibly embodied in the people around us, when we’re practically showered with them. It’s good to keep this in mind.”

Thank you to my extraordinary people—Sean, Ashley, Kristina, Winnie, Seth, Kelli, Help Scout, and everyone at the altMBA.