Do you ever find yourself avoiding conversation with a certain someone—a friend, family member, fellow employee, acquaintance, etc.—because of how he or she may reply, because the outcome may challenge your point of view?
A person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have. — Timothy Ferriss
Just a few days ago, I picked up the phone, took a deep breath, dialed 7 digits, and waited for a likely uncomfortable conversation to begin. A voicemail is all I was able to leave, but I apologized for my untimely failure to communicate effectively, to be transparent a few weeks back, which I perceive to have caused a riff in our friendship. Calling and leaving a message in this case was something I needed to do—regardless of the outcome—to move forward, to let it go.
Uncomfortable conversations can be uncomfortable for many reasons, but they become more so as time passes, as anticipation builds, and the mind begins to imagine and create possible outcomes, many of which are over the top. More often than not, the time spent pondering how a conversation will go is more uncomfortable than the conversation itself.
Is there something you’ve been meaning to tell your parents? Have you avoided talking with your employer about working on that project? No matter the subject of conversation or the person you’ll be having it with, uncomfortable conversations are so because deep down you know that you’ll be better off having them regardless of the implications.
Rather than postpone and push them back days, weeks, or even months, pursue them. The more often you initiate potentially uncomfortable conversations, the less uncomfortable they become, and the more opportunities for success you’ll create.






2 Comments
So true, I also have a hard time initiating hard conversations but feel so much better once they are behind me. It only gets worse with time so just say what you need to say! Great post.
It certainly can be difficult to initiate. I’ve made a list of people I’d like to talk with—potentially uncomfortable conversations—but mostly because they’re old friends whom I haven’t connected with in months / years. One a week is my goal.