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The Importance of Having Difficult Discussions

Updated: May 1, 2023

"I measure someone's success in life by the number of difficult discussions they have had in their life."

This is a quote from one of my favorite books, "4-Hour Work Week" by Tim Ferris.

After taking this quote to heart and realizing its truth, I would like to unpack this quote for you here.

First, let's start with some assumptions made in a statement like this.

There is a need for a difficult discussion.

Making Difficult Decisions

This means there is a problem that needs to be fixed with someone else.

Recently, I had a very deep experience with my friend Rob. We wanted a mindful day, so we walked to a park, sat on a bench, and chatted for 6 hours before walking back. We discuss life, happiness, what makes us mad or sad, and ways we can support each other.

We found one major takeaway around happiness.

It seemed that it was easy for us to remain grateful and positive within our world bubble.

But, we can only be in our bubble for so long.

When you try to communicate complex topics in a fast-moving environment, it can become a challenge to remain positive and grateful while trying to negotiate for a higher salary or explain to your loved one that you do not have time to talk because you are pursuing something at work.

If you want to do much in this world, you will need to interact with others.

Buy food? You need to attain money, which requires working, receiving the money, and then going to a place to buy food and transact with people. So whether you are talking with colleagues, working with your bank, walking through the store (non-verbal communication), or checking out at the cashier, you need to communicate with many people. In this fast-paced life, this can lead to errors in how you communicate or how this communication is received.

They are making it somewhat hard to remain exactly as peaceful while also interacting with the world.

Or imagine you want love in your life. You have to get pretty close to someone and maybe live with them, share money with them, organize plans with them, in the best interest of you both and yourself.

So I agree with Tim Ferris here that there will be times when there is a need for a difficult discussion.

David Goggins says it best… you need to prepare your mind and body for stress because no matter how good your life is or how much money you have, a curveball is coming.

Secondly, Tim Ferris is saying that you have the power to change something (and usually you do not take action, rather bask in pain) but nonetheless have the power.

For this, let's use my foot as an example. My foot feels normal most of the time, but whenever my time on my feet exceeds 2 hours (longer runs, skiing, hiking, etc.), it starts to be in agonizing pain and then goes numb.

I have put up with this for quite a while now.


Just fix it. I am already in pain. It is proven it won't go away. But our psychology keeps us lazy. It hopes it will go away.

Go get the MRI. Do physical therapy. And get over it. The emotional and physical pain is not worth stalling!

Let me be the one to break the bad news to you.

Hope is not a strategy, at least not a winning one.

This goes for emotional pain too. How often are you in a relationship with a loved one, a boss, or a friend, where you spend more time complaining about it than actually fixing it?

Just fix it!

Right Direction

Let them know how you feel, why you feel that way, what you can do to support the change, and make them aware of ways they can also support the change!

Third, the grass is greener on the other side.

Almost regardless of this situation, if you can have this discussion, your life will be better.

And there's will too.

Recently, I had a close relationship with someone with whom I was dealing with a disconnect.

There was a repeated action, and daily, it caused me mental discomfort. I got a bad feeling inside, and it sent me down rabbit holes daily.

It consumed my mind, no matter how much I meditated.

So, I was re-reading the 4-Hour Work Week and came across this quote, stopped in my tracks, and contacted the person. We had an agonizing 2-hour conversation.

Well, the first 30 minutes were agonizing…

The next 30 were emotionally heavy…

This is followed by an hour of envisioning how bright the future can be without this pain!

We got to a point where we were brainstorming ways we could work on this together.

It became a memory for us—something to bond us together and reflect on.

Not all conversations go this way, they will either end up like this, end that job, that relationship, that engagement, or whatever it may be.

But aren't those both good options?

Also, make sure to check out my latest blog post, "Illusions."

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