The (necessary) Luxury of Honesty and Vulnerability

Professionally, my goal was “work hard until something good happens” for many years. I had the luxury of the world’s best string of bosses. I had no idea how lucky I was to be learning from giants who poured wisdom into me, protected me and told me hard truths that shaped my character.

At DARPA I found a new luxury: intense, intentional and open honesty. I learned that as a PM, I could say “I don’t understand” 10x and not be seen as stupid. I could walk into any room as an open book and dig in to my questions. It was glorious and it actually made me smart on several topics. Honesty became my learning superpower.

This was such a contrast to my early years at MIT. I didn’t feel like I belonged in the world of the world’s smartest people. I seemed to struggle in ways that others didn’t. Classes were too hard. In every conversation or class, when you stop understanding, it just gets harder and harder to interject and reveal where your misunderstanding started.

I needed offset strategy to succeed. I took notes in class without understanding things and found ways to learn outside of class. This took the form of finding friends, online explanations, good books and working extra problems. However, I had to act like a spy in 80s Berlin: developing sources to whom I could be truly honest and reveal the depth of my misunderstanding. I found those folks and they made all the difference. It worked, but it was really inefficient.

Real Conversation (AI generated art)

If only I had the ability to said “I don’t understand” in every context; to speak with one voice in all contexts. I would have learned, and contributed, so much more.

All this made me think about the bigger picture to all this: honesty and vulnerability are not just professional luxuries, they are important moral and ethical values. They are essential traits that can help us to build meaningful relationships, grow as individuals, and ultimately live a good life.

Honesty is a powerful tool that helps us to build trust, not just in the workplace, but also in our personal lives. When we are honest with ourselves and others, we are able to form stronger bonds and build deeper connections. This, in turn, allows us to better understand the perspectives and motivations of those around us. This, in turn, leads to more productive and meaningful interactions, whether in the workplace or in our personal relationships.

Vulnerability, on the other hand, allows us to be open and authentic. It’s the only way to build trust. It helps us to be more approachable and genuine, and it creates an environment of trust. When we are vulnerable, we are able to admit our weaknesses and share our struggles, which in turn helps us to connect with others and gain support. This, in turn, helps us to grow as individuals and lead more fulfilling lives.

Furthermore, honesty and vulnerability also help us to build resilience. When we are honest with ourselves and others, we are able to confront difficult situations head-on and find solutions. This, in turn, helps us to become more resilient and better equipped to handle challenges and setbacks.

I’m writing this post because I had the chance to regress recently after I left an aerospace engineering conference for a group of cyber researchers. I felt a little out of my element as I switched contexts. One expert in particular, wanted to make a strong impression as we started talking. The bar was loud. We had a mediocre conversation where I didn’t follow half of what they were saying. They used the opportunity to just throw lots of words at me. We both started looking for exit strategies.

We did talk about some really technical stuff (the limits of TEEs, quantum computing and cyber security, what an efficient market for exploits would look like, etc) but I really didn’t learn or contribute much because I didn’t stop the conversation when I didn’t understand. I wasn’t vulnerable and I didn’t push back in a way that would generate a conversation to remember. That would be a conversation that changed us, not just the opportunity to participate in a professional dance.

However, as I dove back into the AIAA conference, I used this disappointment to dive back into discussions. I was intentional to dive into the discomfort of “I don’t get that, Can you say that again?”, and “I’m sorry, let’s get to somewhere more quiet, what you are saying is important”. The back side of these conversations led to incredible fun, relationship building and some real learning.

If you find yourself confused. Say it and say it early. If you forget someone’s name. Say that too. It’s always better to chose honesty and vulnerability over putting on a front that both you and your counterparty will see through. It makes both of you smarter, and opens the door to real relationships, ultimately paving the way to get big things done.





2 responses to “The (necessary) Luxury of Honesty and Vulnerability”

  1. Chris Avatar

    I appreciate this column Tim. My experience has been that vulnerability and honesty provided the shortest path to build trust and learning, as you said, paves the way to get big things done!

  2. Jim Martin Avatar
    Jim Martin

    What an outstanding perspective. There are so many things for me to take from this, some of which sound so simple, but are so hard to practice.

    I will revisit this, and and your piece on integrity, often.

    Thank you.

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