How I’m Getting Comfortable with Uncomfortable Conversations

In recent years, I noticed that I was hesitant to talk about personal or charged topics until I felt “comfortable.” Don’t get this confused with feeling safe. What I wanted was control of the outcome and ensured success.

Well, that’s not how it works.

This pattern existed in my personal life and at work. If misunderstanding, hard words, or (what felt like) failure seemed likely, I was quick to shift conversations — even those with close friends or family. Similarly, if the tone or topic of a meeting at work was not comfortable, I hesitated to say much. Furthermore, conversations at work that centered around large technical decisions felt inaccessible; I preferred to not get too involved.

It was getting me nowhere.

That’s when I decided to practice releasing any need for the perfect setting, tone, or shared beliefs in order to remain engaged. Fair warning, this is exhausting work, and it doesn’t get easy overnight.

(I had the idea to write about discomfort at the beginning of 2020, back when things were comfortable. It was about then that I decided to practice letting go of my need to feel comfortable in order to say hard things or engage in difficult conversations. With the dramatic increase in levels of ambient discomfort over the past months, there has been no shortage of practice.)


Listen Up

Discomfort is often a signal saying, “Hey, listen up. Something is happening here.” It’s an invitation to stretch and expand and to remain authentic in the face of adversity or disagreement. In between comfort and stress is a place of growth and learning.

Shifting my perspective from, “This is uncomfortable, make it stop” to, “This is uncomfortable, what is the invitation here?” has dramatically changed the outcome of tough conversations.

Ask Yourself a Question

When I start to feel off balance in a conversation or meeting, I try to pause and ask,“What is making me uncomfortable?” It’s been things like:

  • I don’t know enough. I feel ignorant. I don’t know this tech stack like others do.
  • This is getting personal.
  • I might lose respect or acceptance if I share my perspective.
  • This is not how I see the world. I feel disoriented.

The answer to this question is telling and can inform how I choose to engage. For example, if the answer is that I do not know enough, this is a chance to be curious, ask questions, empathize, and learn. Or if the answer is that this is personal, it might be an opportunity to practice authenticity and vulnerability.

The Reality

After practicing for a while, I found that most of the fears that quieted me before were unfounded. More often than not, I was grateful to have remained engaged and curious. And I’m happy to report that the instinct to distance myself from discomfort is slowly wearing off.

With all the changes and events of this year, we have a collective and individual opportunity to lean into the uncomfortable and learn something from it. Embrace it!