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Let’s be honest, many of us are bad at having uncomfortable conversations. Yet having them is essential for growth in life. Your ability to get through them can determine not just your rate of personal growth, but even your chances of success in life.

If you’ve been into personal development for a while now, it is a good test of maturity to be able to go through uncomfortable conversations. This includes experiences like surviving a tough interview, resolving a conflict, easing tensions, settling differences, breaking up with someone, facing a confrontation, and so on.

But uncomfortable conversations are not just about what many would like to refer to as “drama”. They can involve something positively terrifying as well, such as asking out your crush who you’ve been stalking on Facebook. Or approaching a hottie who looks like Marissa Miller. Or making an important call to set up an appointment with an influential yet scary person, who could help you get a raise or promotion.

“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, The 4 Hour Workweek

At times it can be about a serious issue that must be addressed, like a son finally telling his parents his feelings of resentment towards them, or a woman confronting her boyfriend about the subtle condescension he subtly throws at her every day. Being able to express honestly among friends or family that there’s a serious issue, is crucial for the sake of your sanity and well-being, instead of acting fake just to keep the peace.

They’re all an important part of personal growth and development. Like pain, they’re just a part of life. We have to learn to embrace them, and trust that we will be able to handle what comes next. Embrace the silence, the awkwardness, and the uncertainty of it.

Because it’s through them we give ourselves the chance to be unstuck, to grow, to be able to accept bigger truths, and to see a much clearer picture. It’s through embracing the challenge of uncomfortable conversations that we give ourselves the chance to be truly free. Learning from them will push us further in the right direction.

Otherwise, we won’t ever learn, discover or develop anything new. Nothing will change. If you always avoid them, you’ll simply learn to run away each time there’s a problem, and end up living in denial, drawing mischaracterizations, and assumptions about everyone and everything. And by not having them you somehow betray yourself.

Avoiding uncomfortable conversations is a reflection of fragility, of being unable to see and work with the world for what it really is. That is why liars can’t stand truth-tellers, confrontations, or even just a little difficulty in life—they can’t find an honest connection with others and end up highly disconnected from reality. They run at a low level of emotional resiliency—or with none at all.

I’m not calling for you to start being argumentative every single time, to be Mr. Self-Righteous or Mr. Anti-Social Douche. What I’m saying is you have to be able to communicate honestly when it matters. Even if it’s painful to one or both parties concerned. The more you withhold from that much-needed uncomfortable conversation, the more you are prolonging the inevitable. It will be more painful in the long run, either to yourself or to others.

Perhaps it’s scary for many of us to go through uncomfortable conversations because it implies that we’re still somehow not at peace with many parts of ourselves and that we’re afraid of the consequences. What makes it complicated too is when there’s deception involved from someone who doesn’t even deserve to be involved in any conversation at all. Someone who’s just focused on passing the blame, afraid to face the facts and not taking any responsibility. Well, have that uncomfortable conversation with them anyway, if you must. Just cut the conversation short if it’s not going anywhere at all, especially when you’re dealing with a liar. At times you won’t even have to—that is the part where you tell them that there is nothing to talk about.


When your date shows up late and seems uninterested you can say you’d rather hear the truth and save both of you the time. You can even add that if she’s the type who can’t make a decision then the date may as well be over. The bus station is right on the corner.

When you have a friend who’s clearly enabling toxic behavior and is not acting honestly, say it straight that he or she can’t have it both ways and you don’t want any part of it.

When you have to clarify something to a friend so as to make him or her be more comfortable about the situation, go speak your mind. He or she will appreciate it.

Say your piece. Calling out b.s. is necessary. Clarifying your intentions, especially when they’re good, is necessary. Your honesty is needed. If you can’t do it who else will? But be careful as not to use this as an excuse to be a douche yourself.

Handling uncomfortable conversations is an essential life skill in which you develop your own style which gets the point across, but at the same time, it doesn’t push people away (unless you really want to push someone away). You’ll have to find the balance somewhere. A balance where even your harshest critics and enemies can respect you.

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Writer and researcher on advanced self-development, currently exploring many fields of human knowledge. On this site, you will find his writings and perspectives about our society & culture, many of which are counter-intuitive, but backed by experience, common sense, and science.

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