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Being Courageous

Oct 11, 2025

On July 1st, 1776, our founding fathers were struggling mightily to come to a consensus about declaring independence. It was not a foregone conclusion.

At ten o’clock, John Hancock sounded the gavel. Congress was to begin the day’s discussion on independence. John Dickinson, the prominent and once popular delegate from Pennsylvania, was not in favor of the motion. “Gaunt and deathly pale”, he stood to be heard. While there was no formal transcription of his speech, Dickinson’s notes did survive. From David McCulloch’s John Adams:

“He knew how unpopular he had become, Dickinson began. He knew that by standing firm, as a matter of principle, he was almost certainly ending his career. ‘My conduct this day, I expect, will give the finishing blow to my once great...and now too diminished popularity...But thinking as I do on the subject of debate, silence would be guilt.’”

Silence would be guilt...

Many times, we don’t say something because we don’t want to upset our client, or more importantly, we don’t want to sabotage a sale. We don’t want to lose our clients’ trust. Ironically, by not saying something we are doing both of those things.  We are guilty - guilty of not doing our duty.

In Dickinson’s case, it took incredible courage to speak up, even though he ended up being on the “losing” side of the argument, which brings us to Virtue #10 - Being Courageous.

Do we have the resolve, self-confidence, and determination to say what needs to be said? Are we willing to go beyond the surface conversation and dig into what’s not being said but must be acknowledged to create great outcomes for our clients? Even if it comes seemingly “at the expense of a sale”? Whose interests are we serving anyway?

Being courageous is speaking up when silence would be easier. Dickinson knew that speaking his mind was required - it was not an option to stay silent. However, as advisors, it is not about speaking our mind; it is about helping our clients explore the truth so that they can make the best decision possible. Back on that day in 1776, Dickinson’s main reservation about independence was the ability to succeed in secession - could they unite and defend themselves? He felt the best solution was to find a way to reconcile with Britain. In a way, he was doing his job! Of course, independence worked out...but if it didn’t, he would have looked like the wise sage.

Which is the whole point when we are talking to our clients - we are not there to tell them what they want to hear. Our job is to point out all the options, obstacles, challenges, road blocks, speed bumps - all the things that could go wrong.

In your day-to-day, you know the obstacles, the challenges, the potential pitfalls. Not telling your client about them is a breach of duty. Therefore, when one of those things happens, the client wants to blame you because...you knew about it and didn’t say anything! Put in this light, it seems obvious that we should simply tell everyone everything up front. But that’s usually not how it shows up.

There’s nothing wrong with being optimistic. When we are “selling”, we are putting things in the best-case scenarios, but life rarely happens in the best-case. It often barely makes it to mid-case. Today, as I write this post, my wife went to take her car in to be serviced. (Usually, I do it, so this is not a common experience for her.) She has an appointment at 8 am. As she pulls up, there are three people ahead of her. Shortly after she pulls up, three more people come up behind her. The loaner isn’t ready - the service advisor is cleaning and vacuuming the car so she can get in and drive off. She gets in the car and looks at the gas tank, which has 85 miles left. She has been driving an electric car for almost 5 years - putting “gas” in the car is definitely a major inconvenience. Not the experience she expected - or was promised when she purchased the car last year.

Sometimes things go off the rails. Maybe that service experience isn't that bad, but I can assure you that if I call the service manager, he/she is going to be very upset.  

Here's something a little more serious: I once had to sell a property four times.

As a listing agent, I pre-inspect every property. My thinking is, why not find out what issues there are before the buyer does? So, in this particular situation, the inspection report comes back, and there is the usual hit list of modest items on a 50-year-old house. In the summary, which is what most agents and clients focus on, there isn’t even a mention of mold. It’s way back in the report.

So we put the property on the market, get multiple offers, and go into contract with a seller well above the list price. The buyer does their inspection and says, “Hey, there’s mold. We are cancelling.”

Ooops. Big problem!

We get someone out there to investigate and get an estimate to repair. Meanwhile, we get another buyer to go under contract. We explain what is going on. The buyer says, “No problem.” We go back under contract. Buyer #2 does their inspection and says, “Hey, there’s mold! We’re cancelling.”

We go to buyer #3. I literally shout at the agent, before they present to their client, “Hey, there’s mold!” Same result - buyers go under contract and then cancel at inspection.

My clients are ready to lose their minds at this point. They live in Wisconsin, and they have this empty home in South Denver - unsold. Again.

But they were not mad at me! First off, during the pre-listing process, I said, “I recommend we do the pre-inspection. And, just so you know, inevitably, something is going to get missed. It always happens. There’s at least a 20% chance that something comes up when the buyer inspects.”

So, when something came up, they weren’t surprised.

As we went back under contract, regardless of what the agent told me, I told the sellers: “There’s a good chance that once the buyer gets in there, they are going to change their mind.”

And that happened...two more times!

On one hand, I look like a fortune teller. On the other hand, maybe they thought I was cursed? Nah, just kidding. But they had doubts! We were in a tough spot! They were getting nervous, stressed, and anxious. And...this was getting expensive. It ended up costing approximately $20,000 in repairs, plus they ended up taking a $30,000 reduction in sales price from where we first went under contract. In total, that’s $50,000. How “easy” do you think it is to have these conversations with clients who are facing these kinds of circumstances?

Except, what if I hadn’t been that upfront and straightforward? What if I had tried to sugarcoat it, or put it in a “positive and hopeful” light? Where would that have left the seller? Upset, frustrated, disappointed...and probably feeling duped.

Being courageous is about going beyond what we are feeling. It’s about what is best for serving the client’s interests. The clients need to know the range of scenarios they are facing.

Earlier in my career, I was a chicken. I was not willing - or not able - to have these kinds of conversations. It takes practice. It takes confidence. Confidence and courage come from taking and surviving a risk.

The trusted advisors who have long and successful careers are courageous. They have developed the courage to have these conversations, ultimately serving their clients at the highest level. It isn’t about the advisor's feelings and emotions - it’s always about the client.

John Dickinson wasn’t totally against independence; he simply felt the colonies were not ready to handle secession. In all fairness, despite his initial opposition to the secession, he served in the Continental Army after the Declaration of Independence was adopted.

But the fact that we have a Declaration of Independence is a direct result of John Adams’ stand and resolution for it. Said another way, his courage. It was Adams’s speech on July 1st, after Dickinson's, that moved the Congress towards secession. Thomas Jefferson said of that day that Adams spoke “with a power of thought and expression that moves us from our seats.”

“The true source of our sufferings has been our timidity.” - John Adams

 The opposite of timidity:  courage.