Navigating Difficult Conversations

Vanessa Bennett
6 min readMar 7, 2018

You would think, as a therapist and someone who has been actively doing self work for about 10 years, difficult conversations would be easy for me. Surprise! They’re not. I would venture to say they aren’t for most people, hence being called “difficult,” in the first place.

When working with clients, I have many communication tips I share with them as they struggle with and prepare themselves for difficult conversations they need to have with friends, family, partners, coworkers etc., (I’ll give a few below). Every person is so unique with different triggers and sensitivities, different past experiences, communication skill, technique and approach. Plus, we’re all human, so of course we accidentally hurt people’s feelings (and maybe even sometimes on purpose), so wouldn’t it make sense that many intimate or serious conversations are difficult to navigate?

Photographer:Ana Paula Lima

The funny thing is, in my experience, and what I see in working with others, the build up to the conversation is usually far worse than the talk itself. The agonizing over the details, when to approach them, how they may react, what you might have to counter with. All imaginary scenarios obviously, since we are not able to predict how another person is going to act or react. The anxiety we cause ourselves reminds me of the slow peeling off of a Band-Aid. Pulling out tiny hairs one at a time.

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Vanessa Bennett

Psychotherapist, Mindfulness + Codependency Coach. Cohost of the Cheaper Than Therapy Podcast. IG:vanessasbennett