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Finding Success in Discomfort

Finding Success in Discomfort

A person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.” – Tim Ferris

Success in business can be connected directly to the number of uncomfortable conversations you are willing to have.


It’s because people have a natural tendency to steer clear of rocking the boat. In fact, most would rather avoid the situation altogether than have to face it.

But unless you’re willing to properly express yourself in a constructive and open manner, the issue will fester and swell to an uncontrollable level.

No matter the situation, having the ability to navigate through an uncomfortable conversation effectively and constructively will bring comfort and freedom to your workplace and your life.

Here are four steps to facing your fear of an unpleasant encounter and make way for more personal, and professional growth.

Plan ahead

A difficult situation can bring about feelings of anger, fear, and worry. Don’t react quickly! To prevent a runaway train, take the time to prepare yourself and approach the person in the most efficient way possible.

Stay away from email, and have the conversation face to face, or at the very least, over the phone. Email is a delayed, one-sided conversation that cannot convey emotion or tone. Words can become misleading and can derail any progress moving forward.

Set aside the correct amount of time to discuss the issue at hand. The feeling of discomfort is brought on by an incoming e-mail. If during your response, you feel the keyboard starting to get warm it’s time to walk away and schedule a time to talk.

Set guidelines and an agenda for your meeting, and set a priority list of what you would like to accomplish. Stick to the script.

Start with empathy, then listen.

Everyone is going through everything, at any given time.


What I mean here is, it doesn’t matter who you are, your issue will seem big in your world. But make sure you appreciate where your problem ranks in the world of the other person.

Whether you know it or not, the discontent, action or pain they have could be a consequence of a larger issue in their life. Allow yourself the freedom to forgive, and focus on the issue at hand. Be efficient in your plight. Be open and be honest.

Start with a question to allow the other person to initiate the conversation, and then actively listen. Make a concerted effort to understand and acknowledge their point. Doing this will enable you to craft the response around the truth at hand, and may allow you to see the issue from a different perspective.

Remove the label, remove the weight.

Be mindful of your thoughts. Don’t create a situation that doesn’t exist and don’t predict the future. One small incident can erroneously be construed as a full-blown crisis if you don’t control the labels you place on it.

Removing the labels of a situation will highlight and magnify what is an important issue is and will direct the path of the discussion. Strip away the layers and view the issue for what it is in the present moment and stay away from attaching it to the past or the future.

This practice will provide clarity, allowing you to be more understanding, and will better enable you to be understood.

Be Proactive

Set the foundation for trust with all of the people you communicate and work with.

Be approachable. Be trustworthy.

Treating people in your life and your organization with a high level of respect and kindness will make the thought of addressing the issue less imposing. Having the openness and comfort to approach someone will streamline your interactions with people and will eliminate the future road blocks.

What about you?

Have you struggled with having uncomfortable conversations? What have you done to overcome your anxiety? Please share in the comments below!



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