The Work of Knowing Yourself

My dog needed a walk, and I could not find my headphones.

I checked the counter, the charger, the couch cushions. Found them eventually and headed out. But early in that walk it occurred to me that I had been listening to podcasts for fifteen years, and at some point in the last few of those years, I was listening to podcasts more often than not. Any open moment in the day had become an opportunity to put something in my ears. A walk, a drive, doing dishes... my podcast playlist was always readily available.

I told myself it was curiosity. And it was, partly. But I had also stopped spending much time in my own thoughts, and I am not sure I fully recognized this tendency until that walk. Consuming ideas had become the default while sitting in my own thoughts had become the exception.

After reading Digital Minimalism, I knew what problem I was trying to fix. Yes, I was losing the battle for my attention (smartphone + apps + notifications) to companies that had incentives to capture it, but more importantly, I was unknowingly sacrificing the journey of becoming my own person.

Distracted from Discomfort

Developing an authentic point of view about who you are and what you believe is slow, uncomfortable work. It seems like every stage of my life has presented situations, relationships, or pathways that prompted me with questions about who I am that I didn't have answers to. And so I would find ways to fill the space out of avoidance because having an answer was uncomfortable.

I see a version of this in job searches regularly. Last week I was working with a client who logically understands why a targeted job search works better than a scattered one. But when I pushed them toward specifics (a short list of companies, a defined role type...etc), they pulled back. Narrowing meant excluding, and excluding felt like risk. Confidence and conviction weren't the problem. But they hadn't wrestled with what mattered to them enough to trust the direction they chose.

I knew how they felt because I had been there too.

I've gone through a lot of my own career without doing much of that internal work. My first real career decision was saying yes to starting a company with a friend because he was my friend. A few years later I was in a sales role, then a strategy role, then leading a product team. Looking back the dots connect. But there was very little intentionality to know them ahead of time, and the decisions that made them were rarely driven by a clear sense of who I was or what I actually wanted.

Clarity = Leverage

My friend and mentor, David, takes a different approach. He was recently promoted to CEO of a public company, and trust me when I say this isn't a surprise. I have followed his career for years, and yes he's qualified, but more importantly, he knows those uncomfortable questions. What kind of work he does best, what he needs from an environment, what he will not compromise on. Every interaction and decision he makes seems to have that foundation underneath it, and his career has progressed with a clarity and speed that I think is directly connected to that.

Let me be clear, knowing yourself does not make a job search simple, but it absolutely creates alignment. You know which roles are the right fit. You convey authentic confidence throughout each interview. And decisions are easier at every stage.

We consume an enormous amount of information about how to search, how to interview, how to position ourselves, and far less time determining what we actually want or what we actually believe about the work we do best. Ironic, right?

Start With a Few Questions

For years I've seen people like David thrive because they possess a self-awareness that is maintained with routine reflection, but is clearly built on the foundational questions that drive everything else:

• What are your professional values?
• Where do you thrive?
• What truly motivates you?

I know this type of reflection can be harder to do alone than it sounds. If you are in the middle of a job search and feeling unclear about which direction to commit to, reach out. It is one of my favorite conversations to have.