Having Awkward and Uncomfortable Conversations Leads to a Better Life

Nobody wants to have them, but they are endlessly beneficial in many aspects of our lives

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We didn’t have uncomfortable conversations in my house. We didn’t have them outside of our beat up but relatively happy two-bedroom apartment my Dad and I called home though either. I was never taught how to have them. Only recently have I considered how different our entire relationship and collective pasts may have been, had we just a few more uncomfortable and awkward conversations.

So I didn’t get any practice at home, where most people learn those sorts of life skills — and it’s not like there is or was a class on how to have an awkward conversation. At first, this resulted in me either shying away from them or finding a way to make them more awkward with my social awkwardness.

There were ones my old man probably should have had with me as a teenage boy, you know, the birds and the bees or what have you — he just didn’t know how. Our collective anxiety and awkwardness stopped it from happening. Plus there was the fact I was having girls in my room from the time I was like ten on, so maybe he figured I had it figured it out for myself?

Whatever the case, all I recall being said was something along the lines of “Don’t get anyone pregnant, neither one of us can afford it”. He tried.

As far as jail and breaking the law were concerned it was “I won’t come bail you out, you’ll spend at least the night in jail so don’t bother calling if you do something dumb and get caught”. He’s a man of few words but much wisdom.

Not for nothing, as awkward as those “talks” were, they more or less were effective as I still don’t have any kids and was only locked up once in my entire life. All things considered, only once is a miracle.

Anyhow, as I got older and the art of the awkward conversation was still pretty foreign to me, rather than initiate them with people close to me — say about how something they did had bothered me, etc. — I’d either lash out or just quietly add them to a long and evergrowing list of people I resented.

I promise you, that’s no way to live. I tried for a painfully long time.

It is not just on the personal or domestic front where the awkward conversation can vastly improve things either.

Asking for a raise can be awkward. The same goes for asking someone out and being asked any of the awkward shit they ask you at corporate job interviews.

I could go on forever with examples of everyday awkward conversations that you will have to find a way to at least have if you want even a half-decent life, despite if you stumble through them or your voice shakes or cracks.

To avoid every potentially awkward conversation, exchange or moment is to hide from life. My best advice is to get comfortable with being uncomfortable, to avoid becoming wildly unhappy. Things get uncomfortable sometimes, what do you want me to tell ya?

However, if you can get good at these awkward convos, in due time you could potentially master them — which in my opinion and experience truly is the key to living as happy and healthy of a life as humanly possible.

They can help you get ahead professionally, keep things open and honest at home and with everyone in it — regardless of who it is.

Keeping friendships healthy, non-co-dependant, and non-toxic, will likely involve an awkward conversation or two. If you’re lucky, however, you’ll have friends you’re so close with, these civil discussions won’t be uncomfortable at all because they’ll understand where you’re coming from or at the very least respect it and you for speaking up.

Because the more you don’t speak up for yourself in life in general, no matter how uncomfortable it may be for a very brief moment, the more people will take advantage. It’s the old ‘Give them an inch and they take a mile philosophy’. And whether they want to admit it or not, most people don’t respect a pushover. At best, we feel sorry for them.

I don’t know about you but that’s not the life I want.

At the end of the day, all initiating so-called awkward conversations really is more often than not, is simply being honest with other people. Being truthful about what we want, expect or expected, how we felt, or how we feel — and why should that be awkward? We don’t have to feel bad for being honest.

Short of obnoxiously voicing your opinion that would insult someone else, especially when they didn’t ask, rarely do we ever have to feel bad about being honest.

So go have that awkward conversation you’ve been putting off forever, the one that’s keeping you miserable and you wish you would have just gotten out of the way months ago to save you the misery. It’s never too late, it’s not having it at all which will lead to too late.

Writing About the Human Condition, via My Thoughts, Observations, Experiences, and Opinions — Founder of Journal of Journeys and BRB INC ©

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