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

If my meal in a restaurant isn’t good, I’ll send it back.

If I am not happy with a service I receive, I’ll make the company aware.

If I’m unhappy about anything really I’ll voice my concern.

I actually enjoy awkward conversations but my wife hates it when any of these situations arise. She is embarrassed and wants a massive dark hole to appear that she can crawl into.

To me though, these types of conversations help everyone. I get what I pay for and the business gets some valuable, constructive feedback.

I used to have a boss who was terrible in restaurants; a meal could be good and he’d still be pissed…

He would ridicule the waitress and be quite pompous about the whole thing. It was excessive, unnecessary and often rude. There is a right way and a wrong way to go about it.

That’s the difference between getting a great meal at the second attempt or something that came out of the chef.

Dealing with people is a skill, a critical skill that you need if you want to make a success of your life. This is something that is never taught in schools, yet it must be mastered.

The good news is, no one is born good at this — it is a learned behaviour.

Related — How to be the Luckiest Person Alive!

Here are some other examples of potentially awkward situations that you can take away great things from; if you play the game the right way…

Asking Someone Out on a Date

Life is too short to give a shit about this being awkward. As I wrote in ‘If You Want Something You Have to do the ASK’ if you ask 100 people to have sex with you on the street and one says yes, then you’ve won. You’ll never see the other 99 again anyway!

It’s the same with most things in life. You only need a small percentage of conversions to have incredible success.

And who knows… today could be the last day you ever ask someone out on a date. Your future husband or wife is out there waiting for you. Be bold true warrior!

Dealing With a Complaint

Shoe on the other foot, maybe someone is complaining about your business or service…

Remember they are not the enemy. They are now your most valuable source of information. Probe them, what could you do better?

No matter how much of a problem they are, treat them the same as your favourite customer. A trick I love using in this situation is – pretend they are going to die tomorrow.

Would you be mad at someone on their last day on this Earth or would you give them a great last day? If they don’t die they will more than likely be back to buy from you again.

Maybe today is the day you make your ‘worst customer’ your best. Empathy always wins.

Dealing With Random Douche Bags

Again, they are going to die tomorrow, pity them. Don’t be mad at them.

Maybe they are like that because they’ve had a tough life. Maybe your attitude towards them today will help give them a renewed sense of hope. Maybe you’ll save their life. That would be a good day.

Related — 9 Ways to Make Today a Great Day

Dealing With Someone Who Hates You

I really believe that it’s a lot easier to love someone you once hated than to love someone new. There’s already emotion there…

Like when the bad guy in the movies suddenly treats his girl well and he’s a ‘changed man’ he’s a hero! No one gives a shit about the guy who’s been nice the whole time. That’s boring.

It’s weird but it’s true…

The naughty kid who becomes a good kid gets more credit than the kid who always behaved.

A drug addict who changes his life gets the plaudits over the guy with the steady job for 40 years. People care more about those who’ve overcome adversity.

So, no matter who you are or what you did in the past – it could just be your secret weapon to building relationships in the future. Be honest, show your wounds and tell your story.

Be real and relatable. Maybe today the person who has always given you a hard time will get the privilege of understanding you for the first time.

Related — How to Turn Haters Into Your Biggest Fans

Asking for a Pay Rise

People are scared of this. I never have been, I’ve enjoyed every negotiation I’ve had. If you know your value and the value you are adding to your employer, this is a good conversation. If you give me X, I’ll give you Y is the simple way to look at this.

They should leave happy to have met your request because you are giving them more value back. You are offering them a good deal, so just go do it.

More money in your pocket, and a happy boss.

Related — How to Get a Pay Rise in 6 Easy Steps

Asking for a Sale

Again, you are proposing to give your customer more value than they are paying for. Why be afraid of closing? If you believe in your product this should never feel awkward.

Confidence comes from doing something successfully again and again, so who knows… that sale you ask for today could propel your whole career forward.


When dealing with perceived uncomfortable situations, think of the value you are adding to the other person or business. Understand your worth; you are helping them too.

If you come across a difficult person in life, be empathetic to them. Think about why they are doing what they are doing. Treat them like they are going to die tomorrow. But don’t waste time on those who aren’t worthy of your attention.

And most importantly of all…

Why think of anything in life as uncomfortable…?

There is a 400 trillion to one chance of you ever being born. Or something like that.

No one knows why we are here, or what happens when we die.

We all have our own individual worries, dreams and beliefs. We have all been through hardship and we’ve all had different life experiences to this point. There’s a lot of reasons why each person is the way they are that nobody else understands…

Why outsource your self-esteem to other humans who are just as scared as you?

Related — How to Never Worry About Anything Ever Again

Life is short and as far as any of us mere mortals know, we only get one. So dive in; live, love and ask for anything you want from life. Enjoy every potentially awkward, uncomfortable moment you have in the future…

Because nothing should be uncomfortable to you. You are uniquely valuable to everyone you meet and they are lucky to engage with you in any aspect of life, because there is only one of you.

Remember that.

-Matthew Brown

What would you add to this list? Let me know in the comments. If you want a follow up article on any of the topics discussed here just ask me — I’d love your feedback.

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Thank you for some of your attention.