There are certain skills in life that require us to lean into discomfort. 

Having difficult conversations is right there at the top.

It was for me, at least. 

Maybe, you too?

Some people seem to find it easy to say EXACTLY what’s on their mind.

They have no issue with “coming off like an asshole” if the recipient doesn’t like what they hear. 

“Deal with it, brah,” is the general sentiment.

We even often sort of backhand praise people like this for having “no filter.”

“Well, there’s no wondering what Dave is thinking, that’s for sure.”

We all chuckle and think, “Yeah, that must be nice.”

So, why does speaking up feel
so unnatural for the rest of us?

Have you ever had those moments where you KNEW you were being WRONGED in REAL TIME and simply could not get yourself to push the words out of your mouth to correct it?

I don’t mean like an abusive partner or something traumatic…

I mean like, the lady at Dunkin Donuts just power-pumped four shots of high fructose death syrup into your iced latte when you very clearly stated “NO sugar, please.”

But she never really stopped to listen, and was gum flapping with the other lady back there about how much the job sucks and what a moron that last customer was, and now you’re standing there numb, uncaffeinated, watching her fly through her reckless and remorseful life like the Tasmanian Devil, which is NOT your fault, but IS now your problem… 

And while any semi-secure human being would say to her, “Excuse me, miss, I asked for no sugar,” and let her deal with whatever miserable reaction she wants to have over it… (as you watch intently to make sure nothing “extra, extra” finds its way into it.)

I mean, that is just standard human function, right?

See something, say something. Speak up for yourself.

But, for some reason… in a moment like that… YOU just stand there, half frozen, pay for the poison drink, plus tip!, and think, “Well, it won’t kill me to have sugar for ONE DAY.” 


All the while dreaming you could be “No Filter Dave” in that moment and say something like: 

“WHOA, WHOA… Deloris… You gotta slow down back there. You just pumped a crack rock of sugar into my no sugar drink. Can we start that one over, please? They have you working too hard, D. I feel you. Mistakes happen. We’re gonna get it right this time!”

Ten seconds later Deloris hands him a perfect drink, with a big smile, thanks him for “getting it” and insists he take it for free. 

So, what is that about? 

Some people just get to be born
with the “speak up” gene?

No fretting over the consequences? 

Or how the world will judge them if they accidentally hurt somebody’s feelings?

And friends asking, “Is everything okay with you? You seem a little irritated lately.”

“I seem irritated? All I did was speak up for myself. Dave does that and you think it’s great!?”

“Oh, wow. Now you REALLY seem irritated. Anything you want to talk about?”


Since digging into my primary Enneagram – Type 9: “The Peacemaker” – it’s obvious why having conversations I found difficult used to feel like torture for me. 

Hey look, it’s right there in the title.

Peace Maker!

Making anything but peace with my actions was against my natural-born intention. 

Or, so was the case for more than half of my life. 

So, what changed?

Why do I actually embrace (dare I say, look forward to) having difficult conversations these days?

Well, first I just grew up. 

Business and parenting has a way of forcing that on you.

Suddenly it’s not a cup of coffee you’re sacrificing by letting life walk all over you… 

It’s your livelihood. 

Your family’s well-being. 

Your reputation. 

Also, as a coach, I’ve had to help others reset their mindsets around this stuff… show them that what “feels good” to go along with in the moment… is costing them real money the moment after. 

That the only reason it even “feels good” to acquiesce to certain requests is because we want to avoid the pain of saying “no”… but doing so then leads to more pain, and regret, and animosity towards the person you should have said “no” to in the first place. 

That sucks for you and is unfair to them. 

Because now they’re paying a silent regret tax for you having a weak spine.

Bad business, hombre. 

Once I figured out, and saw real proof, that difficult conversations are the most respectful kind you can have with someone…

I began to truly embrace opportunities to meet people at that moment. 

Because the need for uncomfortable conversations IS going to arise.

So, trusting that you will know you have GOOD INTENT behind any uncomfortable conversation you need to have with someone…

And, be willing and able to communicate your intent with confidence and clarity…

Makes how they respond to their own issue to deal with.

And I’ve found that most people get that and appreciate it. 

They don’t always LIKE it, but they respect it. 

Just like I do when I’m on the other side of it.  

As my great friend Jessica Mae Stafford likes to say, “You can honor the person without guaranteeing the outcome.”

Feel the freedom in that? 

Nice, right? 

Now, go out there and speak your mind. Respectfully. 

And get yourself some better coffee, for crying out loud. 

Dunkin Donuts doesn’t deserve you.

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