Your Success in Life Depends on How Many Uncomfortable Conversations You’re Willing To Have

Anthony Moore
Oct 22 · 6 min read

Yesterday, my wife and I were in the yard playing with our dog, Penny.

We both heard a big slam, like something falling over. I looked towards our front gate, and saw a box from Target lying unceremoniously on the floor. We put two and two together: the delivery person just threw our box over the gate.

I was angry. My wife assured me the box was full of towels, but what if we had ordered something fragile? I decided to go out and see if I could catch the delivery person.

I walked out the gate, and saw a mailman, busily shoving envelopes into our mailbox. And at that moment, I stopped. Froze, is more like it. I wanted to stand up for myself. Don’t throw our packages across the yard! I wanted to scream. But I was scared. I even turned back towards the house.

Then, I stopped again. Decided to be brave. “Hey!” I called. The mailman looked up. “Um, did you just throw our package onto our yard?

No, I just dropped it over the gate,” he answered defensively. (As if that’s better?)

Well…thanks for delivering it, but I’d appreciate it if next time, you just set it in the floor,” I responded. I hoped my nervousness wasn’t too obvious.

I was ready for some awkward fight with the mailman about not telling him how to do his job or something. But to my surprise, he actually apologized and said he wouldn’t do it again.

#1 New York Times best-selling author Tim Ferriss said one of the most-highlighted sections on the kindle-version of his book The 4-Hour Workweek was this passage:

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

When’s the last time you had a chance to have an uncomfortable conversation — and totally ran away?

It’s more costly than you think.

You Must Step Forward Into Growth or Backwards Into Security

“Every next level of your life will demand a different you.” -Leonardo DiCaprio

C.S. Lewis once described humans this way: “We are like eggs at present. And you cannot go on indefinitely being just an ordinary, decent egg. We must be hatched or go bad.

You do not have the luxury to “wait” to improve. Like an egg, you’ll either progress into a new version of yourself, or go rotten. There is no other way.

Most people continue choosing security and safety over the choice to become the fullest version of themselves.

Wrote Louis Sachar, author of Holes:

So, what’s it going to be — safety, or freedom? You can’t have both.

Right now, you have the choice — step forward into growth and development, or step backwards into safety and security.

I’m not expert at this. I still shy away from many uncomfortable conversations. My wife is always surprised at me when she learns my fast food order was messed up, yet I say nothing. Frankly, I usually just don’t want the hassle. Telling a cashier at McDonald’s that my order was wrong is…uncomfortable for me.

But I try to step up when they’re important conversations. Most people step backward, slowly killing their chances to become extraordinary. They shy away from difficult conversations, not stepping up when they need to.

Seth Godin once said, “The problem is that our culture has engaged in a Faustian bargain, in which we trade our genius and artistry for apparent stability.

The sad truth is: there’s no such thing as security. Money can be taken away (how many times have you heard of a multi-millionaire going bankrupt?). Our health could fail at any time. Millions of people are abruptly fired or laid off every year.

Security isn’t real.

We must choose to design our own life, and let go of our addiction to “apparent stability.” If you’ve traded your genius and creativity for “stability,” it’s time to get those back. Start having conversations that make you feel insecure or uncomfortable, because they have an enormous impact on your future.

A Trick That Works For Me

A few weeks ago, I was on a walk around my block. I saw a homeless man, and a thought popped into my head: go talk to him.

I’ve had thoughts like these before — go talk to, and maybe help, a stranger. I can tell you the one thing that will always stop me:

Thinking about it too much.

If I allow myself to stew and analyze the facts, There’s a 99% chance I’ll chicken out and avoid the conversation. This has happened to me many times.

But over time, I’ve found a trick that works for me — don’t think about it. Just do it.

So that’s what I did. I started to rationalize and analyze — maybe the man didn’t need help, maybe I should go talk to someone else, the nature of homelessness, etc. — but I stopped myself. I walked right up to him and asked how his day was going.

We ended up talking a bit. He wasn’t in a great state of mind, but I offered to buy him some food and we chatted for a little. I told him maybe we could talk again sometime.

A trick that works for me — I don’t allow myself to think about it. Because once I do, I almost always talk myself out of it.

When it comes time to have an uncomfortable conversation, don’t think about it. Just do it.

The Enormous Power of Just Saying It

When my wife and I were in premarital counseling, our counselor gave us a piece of advice that would end up changing our lives:

Always make the first move.

The meaning is simple: if you can help the relationship, then do it. Don’t wait for the other person to act (even if you don’t want to).

Most people have strained and superficial relationships with family and even with friends. This is because most people always wait for the other person to “make the first move;” say hello, organize a hangout, or apologize.

This is a pride thing. It’s one of the main killers of marriages, friendships, and even families.

If you want to have deep, meaningful relationships with your friends, family, and even just the people in your day-to-day life, make the first move — even if it should be them. Even if it makes you uncomfortable. Be the first to:

For a long time, I felt awkward and uncomfortable telling my brothers and sister “I love you.” Three of the people whom I loved most in the entire world, and I couldn’t say it!

Now, I tell them I love them all the time. I say it over text, over casual phone calls, at crises, celebrations, and over the holidays. I tell my friends, too. Every single important person in my life — mentors, family, friends, even coworkers, know how special they are to me.

It feels silly to be afraid to say this to a loved one. Yet, so many people can’t say a few simple words that would galvanize the entire relationship and deeply touch their soul.

Once you can do this, you can begin enjoying a gem most people never will: close, loving, life-giving relationships with many people.

In Conclusion

Cold showers have become a fad, and there are lots of fun reasons why — it’s healthy, it improves mental performance, it wakes you up, etc.

But the best reason I’ve ever heard for taking cold showers is this:

If you can’t handle something as low-stakes as stepping into a cold shower, what makes you think you can handle high-stakes problems, like asking for a raise or making a huge sale?

Having uncomfortable conversations determines some of the most important parts of your life — your income, the quality of your relationships, your health, your emotional well-being.

Ready to Level-Up?

If you want to become extraordinary and become 10x more effective than you were before, check out my checklist.

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The Post-Grad Survival Guide

We're confused twenty-somethings. We dish on our post-grad blues, successes, failures, and everyday life right here. Featuring topics related to work, relationships, travel, finances, and so much more.

Anthony Moore

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My new book just came out! What Extraordinary People Know:

The Post-Grad Survival Guide

We're confused twenty-somethings. We dish on our post-grad blues, successes, failures, and everyday life right here. Featuring topics related to work, relationships, travel, finances, and so much more.

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