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Why it’s ok to be comfortable with the uncomfortable, according to Eddie Hinkle

Depending on where you grew up, 4H might be a familiar or foreign term. For multihyphenate creator and engineer Eddie Hinkle, the youth development program was one of the first times he realized that combining his interests with the potential for income was possible.

“(In 4H), you would choose subjects or topics that were interesting to you. They had these books and one topic was computers.I thought, ‘cool’ and started reading. It helped me put together a computer from scratch,” which promptly turned on and within a half second, immediately off, he says with a laugh.

Fortunately, that didn’t deter him from continuing down the path of combining his love of computers with building things (to the benefit of himself and so many others), extending to his day job as an engineering leader with Glassdoor and his other pursuits that include being writer and host of the WebJoy podcast.

Below, Eddie reflects on his journey, reading his way out of impostor syndrome, and sticking to his values — even if he fails to honor them every now and again.

Don’t make me think

What does the beginning of the work/life balance story look like for someone who doesn’t fit a familiar narrative? As Eddie navigated stages of his career, from freelancing to a typical “9 to 5”, he began to realize what many of us can’t put into words — he found his work to be gratifying enough, but wanted more out of life. What he could say for sure, though, is that overthinking it wouldn’t get him anywhere.

“In that first 9 to 5 I was a front-end engineer. No one was doing product design, so much was janky and I found this love for UX. So suddenly, I’m not just a front-end developer. I started getting books on how to design things well,” he said, pointing to Steve Krug’s Don’t Make Me Think as an early inspiration. “I (realized I) don’t want to just build something, but something that was engaging.”

Eddie Hinkle - Engineering Leader at the intersection of technology and people
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It also put Eddie on a trajectory to do something many of us cannot: quickly separate the things he did — and absolutely did not — want out of such a large part of his life. Fast-forward to some time later with a new opportunity, and unfortunately, unforeseen challenges.

“I eventually ended up at this job with a horrible boss,” he said, juxtaposing that experience against his previous “dream” scenario, where his only guidance was, “do what you want as long as you get things done” and instead was faced with what he defined as a series of bad cliches (e.g., constant negativity, working on weekends, urgent conversations about unimportant topics).

As luck would have it, an unexpected exit opened the window to an opportunity. That manager’s departure not only paved the way for Eddie to step into their shoes, but also change the tone for the entire team. “I told myself, ‘what happens if someone worse comes in?’ This is an opportunity. I had never thought about management or that (leadership) trajectory.”

So Eddie turned to the tactic he knew from those days of building his first computer — immersing himself in everything he could about a topic — in this case, what it takes to make a good leader.

“I decided I’m going to listen to so many audiobooks. I started listening to books about management and culture and work. (Over time) I saw this amazing team come together and realized I could do this management thing,” he says.

Tackling impostor syndrome, finding comfort in being uncomfortable

Impostor syndrome is described as a “psychological occurrence in which people doubt their skills, talents, or accomplishments and have a persistent internalized fear of being exposed as frauds.” It has cemented its place in today’s career vernacular, embedded in our work culture and talked about ad nauseam in how to better manage and grow as a person and professional.

Without the luxury of the cultural zeitgeist, it was simply a feeling that Eddie couldn’t put to words, but rather had to overcome with time.

It’s interesting because one thing I learned about myself is that I have to be ok being uncomfortable.

“It’s interesting because one thing I learned about myself is that I have to be ok being uncomfortable,” he says. “We talk a lot about impostor syndrome and I had it my whole career. I didn’t realize it was there and kept feeling uncomfortable and had to keep pushing through."

That’s one reason why I read so much. If I feel unequipped for this position I’ve landed and can ask myself, ‘How do I learn that?’ and ‘How do I become comfortable?’” I’ve found that I could do anything as long as I was setting the time to learn about it. It was always scary at first, but it’s always worked out.”

Intent has also played a massive role in becoming the leader he always wanted for himself, and in turn, wanted to be for others. “Each move was centered on a passion of my own. I really wanted a team that didn’t feel what I felt in the past. I was doing something that gave me life and passion,” he says.

I think a big factor is doubling down on what you’re passionate about. It was one of the things that was so important to me when I became a manager.

His current challenge: making sure work is a product of passion at a much larger scale through his work leading teams at Glassdoor.

“I think a big factor is doubling down on what you’re passionate about. It was one of the things that was so important to me when I became a manager. With direct reports, I have three meetings when I became their manager where I ask them, “Tell me about your past. What do you want to do years in the future? What are you headed towards and what are you interested in? And now let’s talk about the short term, how do you get there? If you just chase a ladder for the money, you’re not heading towards your passions and a big thing.”

Staying true to your values, even if it means failing every now and then

In talking with Eddie, you can’t help but see the positivity and joy emanating from his being, (even if in our case, we’re separated by thousands of miles and a computer screen). Much of that is also evident in his side projects, which includes hosting (the aptly named) WebJoy podcast or writing about topics ranging from product development to unpacking the concept of continuous learning.

“I’ve just always dived into things I’m interested in,” he explains. “I’m into writing fictional stories. When I was younger my brother was a DJ and we would make fake radio shows. It was all of that different stuff that really came together to give me a lot of different experiences.”

What may also be unique (and arguably vulnerable) about Eddie is one part of his website that may not necessarily get top billing, but is critically important to him.

I recognize that a lot of people might not want to focus on their core values because they might fail, but you’ve got to understand these are guiding principles. I’m not going to hit on all of them every day.

“On my website I’ve defined a group of core values for myself and I feel like that helps me reset. I don’t honor these all of the time and I fail every day,” he says with a laugh. “But it reminds me what I want to do and the tough decisions that lead me in one direction or another.”

Putting your core values front and center may sound like playing with fire, Eddie admits, but highly recommends the challenge. “I recognize that a lot of people might not want to focus on their core values because they might fail, but you’ve got to understand these are guiding principles. I’m not going to hit on all of them every day.”

That positive mindset, combined with the vulnerability that accompanies an innate ability to find comfort in the uncomfortable, is what led him down the path to creating WebJoy. It’s not by accident.

“I was on Twitter and saw all this negativity. I would talk about things I love or tools and then the haters would come out,” he says. “I thought, ‘no one gets to enjoy what they love’ and I leaned into those values.”

What if people could talk about things they love? For Eddie, in a sea of negativity, he honestly wasn’t sure if people would be interested in listening to that. “It was one of those things, being comfortable with being uncomfortable. So I started DM-ing all these people. Maybe a fourth of them responded, but almost none of them said ‘no’ outright. It was a lot less scary than I thought, and so many said yes,” he says.

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Approaching his side projects with intent (and joy)

Many of us believe (or at least hold out hope) that the outcomes of our journeys will justify the means. For Eddie, he jokes that he only wishes he could have gotten to that end without so many twists and turns.

“Luck, happenstance, all of our lives involve some of that. But I feel like I've experienced a lot of that in my favor,” he says. “I didn’t have a clear idea of where I wanted to go. Always looked at the next step and never had a map. I wish I would have had an idea of where I wanted to go, not because it would be different, it does not work that way for anyone…but it helps those decisions be more strategic."

Today, you can see much of that intention in WebJoy’s content. As he embarks on the podcast’s second season, he is thinking deeply about the guy who was DM-ing people hoping for a response. He realizes how important it is to bridge the gap between the guests and the community of listeners.

“One of my core values is valuing every person. I didn’t want this (podcast) to be a tour of well known people. I use Notion to track the guests, and one thing I put next to each is the size of their audience” to make sure it’s representative of a wider group, he says. “A season is not just representing influencers.”


See more from Eddie on his website and social media on Twitter (@EddieHinkle) and LinkedIn.