Tuesday Email: The Courage to Be Unpopular

Happy Tuesday!

Every Tuesday, I share one idea worth sitting with before the week gets away from you. Not a checklist. Not a framework. A perspective on what it really takes to build something that lasts — and a challenge to the way you're thinking about what comes next.

I didn't want to start this newsletter this way, but I think it's the only way.

We are all going to disappoint people.

Not some people.

People who matter.

If we want to lead a firm and make a real impact on families, that's not a bug. It's a requirement.

It actually makes me cringe to think it's true.

But it is.

As humans we rationalize that we can get to success and impact without disappointing anyone. Maybe you could do it without disappointing your family. But along the journey, there are going to be people who mean a lot to you, who are ultimately going to be disappointed in you.

The courage to be unpopular is not a personality trait. It's the capacity to prioritize the integrity of your mission over the comfort of the interaction.

The ability to commit to the future, independent of the discomfort created in the present.

As I wrote this newsletter, I sat in the office my dad used to sit in, looking at pictures he'd kept since I was a little kid.

Thinking about the concept of being unpopular brought me back to how he managed client relationships. He was so convinced of his view on investing and financial decisions that he never let others get in the way.

Even if that meant telling clients a reality that hurt them, or made them cry. He was so convinced of what was right that he only wanted people who understood that path, even when that path was painful.

We all fear those conversations.

We soften the disappointment because we're worried about losing the relationship and what that could mean financially.

The reality is, that fear lives entirely in our heads.

The people my dad had those conversations with were upset, yes. Some left. But the majority respected him more because of it.

That's counterintuitive. And it's the truth.

There was a time I lost everybody's money. Some people were understanding. Some were not.

Those who weren't were people I deeply admired, people I wanted to be accepted by.

I had let them down.

But it was the right decision. It allowed me to grow, evolve, and lead better.

That doesn't make it easy. It was the hardest thing I've ever done professionally, and it continues to sit with me.

So, why is this so hard? Why does it sit with us for so long? Why do we rationalize to avoid it?

It's our biology.

Social exclusion activates the same brain regions as physical pain. When we say no to something, no to a meeting, no to a group, no to a referral, we're raising our hand to being excluded. And that exclusion triggers the same neurological response as getting hurt.

Early humans evolved in settings where social exclusion was often a death sentence. Our brains are still wired the same way they were thousands of years ago. The environment changed. The neurology didn't.

What we do is disguise that need for acceptance (and the fear of exclusion).

Our drive for external validation masks itself as collaboration, as team harmony, as consensus. The underlying cost is a systematic failure to address the conflicts that actually need addressing.

Think about Instagram. You look at someone's life and it looks perfect: loving with their kids, laughing with their spouse. What you don't see is that the video was two minutes before they went back to their phone and avoided their family and spouse.

What's under the surface isn't visible. We look at organizations the same way. We see a collaborative, harmonious culture and think it's strong.

But if it's never been tested by friction, it's brittle. When disruption hits, and it always does, it breaks.

Friction creates energy. It's like diamonds. Friction creates magnificent-looking gems.

So what is this costing us?

Every advisor knows this calculation. The relational calculus. We've probably run it this week. A client says something you disagree with and you run the math: do I push back, or do I protect the relationship?

What we're protecting isn't just AUM. It's our reputation for being helpful, available, accommodating. So when a COI sends a referral that doesn't fit, we say yes. When a client asks us to talk to their friend who definitely doesn't fit our ideal client, we say yes. We tell ourselves we're helping out, being a good partner. But what we're really doing is managing fear. Fear that if we say no, we get rejected. Fear that the relationship changes. Fear that they think less of us.

And here's the thing about advisors specifically. We never know if growth will continue.

Growth is hard. We fear that our most recent client might be our last. So when we get the opportunity, we take it. Just like our ancestors who ate whatever was available because they didn't know when food was coming again. Our brains haven't caught up.

We talk about the 80/20 rule all the time. Here's what's actually happening underneath it. Some clients have what's called rejection sensitivity. They interpret every delayed email, every unreturned call, as a sign that you're pulling away. For the approval-seeking advisor, those clients create a constant state of relational threat.

We over-service them.

We deplete our time, our energy, our cognitive load.

And if we audited our client bases honestly, we'd probably find we're spending 80% of our time on the clients generating 20% of the revenue, because their fear is triggering ours.

I've struggled with everything I'm describing here.

I used to think I argued in meetings because I was trying to prove myself. The younger version of me was searching for my value, not adding it.

As I got more confident, I started misreading my own dissent as immaturity. I always felt like I was on an island. The pendulum in my head would swing: I'd share my views, feel like I was creating more angst than value, then go quiet. Back and forth.

It wasn't until a three-day leadership retreat that something shifted. I started talking to my leadership team about exactly this. About feeling accepted only when I kept my different views to myself. About wading back because I thought my dissent was pushing people away.

Something incredible happened.

Everybody leaned in.

They said my views mattered. That they appreciated them. That they wanted them.

What I realized in that moment was that the fear of rejection was built entirely in my head. The troublemaker wasn't a threat. It was protection. All those years I spent on the pendulum, I was fighting a battle nobody else was fighting.

Here's what I'd suggest. And I'm going to do this myself.

Audit your book of business.

Find the clients where you're paying the approval tax. The ones whose rejection sensitivity is pulling you into over-servicing them. Name the worst-case scenario if you stopped. Say it out loud. Then ask: am I okay with this?

The goal is essentialism. The discipline of pursuing less.

It means shifting from reactive to focused. It means narrowing your ideal client profile. It means doing the hardest thing there is to do: saying no.

It's easy for me to write. It is hard for me to do.

There's a woman named Maya Lin who designed the Vietnam Veterans Memorial at 21 years old. Her proposal was selected from over 1,400 submissions. Her design was a simple, polished black granite wall inscribed with the names of the dead, descending into the earth.

The backlash was immediate. Critics called it "a black scar of shame." As an Asian American, she faced racial slurs and attacks on her heritage.

She stood her ground. She argued that to heal from the pain of war, a nation must first accept that the pain occurred.

At the dedication ceremony in 1982, her name was not mentioned once.

A compromise statue was added near the entrance without her input. The sculptor of the compromise statue was paid more than fifteen times her prize money.

Maya Lin didn’t budge.

Today the memorial is recognized as one of the most profound public works in American history. That result would have been impossible if she had bowed to the pressure for something safer and more traditional.

The courage to be unpopular is not a personality trait.

It's a practice.

In an industry built on long-term impact, we have to maintain the long-term view.

Short-term difficulties are going to arise. They always do.

But with a clear vision of your mission and your why, you can build a firm that's actually Futureproof. Not just one that looks like it is.

The best is ahead!

-Matt