Talking to Mike Piper, Christine Benz About the Pressure of Being Right (and Dealing with Their Own Imposter Syndrome)

I was in the middle of talking to Mike Piper, the money expert best known for knowing nearly everything about Social Security, at WCICON26 last week, when an attendee sauntered up to ask him a question about 721 exchanges, a topic she had just learned about.

“Oh, that’s the REIT one, right?” I exclaimed, exhausting my knowledge on that topic in six words (or seven, depending on how you personally count contractions). Piper, who is much more familiar with the topic than me, paused for a second. But he also didn’t feel comfortable answering the question in that moment, even though he was a speaker at a conference about money where he was more well-informed than just about anybody else in attendance.

Why don’t you email me your question, he told her, and I’ll find the answer and get back to you. She walked away satisfied.

Then, Piper and I went back to our conversation—which had started when I asked him whether, as a financial expert and a figure who is a role model for many of the nearly 1,000 people who attended WCICON in Las Vegas this year, he felt pressure to always be right when answering questions about money and finance.

“Emphatically yes,” Piper, who’s also written books on taxes and accounting, told me. “But I also can’t feel embarrassed about what just happened right here, where I say, ‘I don’t know that.’ It’s being very willing to be honest about the limitations of my knowledge. That was a particular question. I don’t know the answer, but I know where to find it.”

We all feel pressure to be correct. Every column I write, I feel that pressure. Every speaker at WCICON felt that pressure. Jim Dahle probably feels that pressure every time he steps up to the podcast mic. Even more interesting to me is somebody like Paul Merriman or Bill Bengen.

Merriman is tied to the small cap value tilt. But if you’ve followed his advice about adding equity exposure to smaller companies, you’ve left money on the table for the past 15 years (even though experts still believe that eventually that will be a winning strategy). Bengen is tied to the 4% rule, even though he actually believes you can spend more in retirement. One of the problems is that people slightly misunderstand his conclusion.

“I was always worried about making some major error,” Bengen told Jim in a recent WCI podcast episode. “ . . . [The 4% rule has] a very specific meaning for it. To me, it represents the worst-case scenario that's occurred over the last 100 years, where you find an investor who had the lowest safe withdrawal rate of all these investors. And that's the number. Obviously, everyone else is going to be able to withdraw more than them, by definition . . .”

Who will likely get the blame, though, if somebody’s retirement fails even though they followed the guideline that Bengen created? It’ll probably be Bengen.

The thought that you could feel responsibility for somebody else’s misfortune might be terrifying to somebody who speaks regularly on podcasts, gives clients financial planning and advice, and makes multiple presentations per year at financial conventions.

For SC Gutierrez, the founder and CEO of Aptus Financial who gave a well-received presentation at WCICON26, she worries that what she says on the stage might be taken out of context and misapplied.

If, for example, she was speaking about the delights of target date funds, she doesn’t want a listener to misconstrue the meaning.

“If somebody thinks, ‘Oh good, target date funds are great everywhere’ and that’s the only time they ever hear me speak and then they go buy one in a brokerage account, that would be a misapplication of the advice,” she told me. “I do try to exercise a lot of humility when I’m coming into a talk. Where could I be wrong? Where could someone misinterpret what I’m saying?”

When I covered the NFL for CBSSports.com a decade ago, I got to be very good very lucky, for a year or two, at picking the winners of NFL games straight up and against the money line. I know people used to take my picks and then make wagers on what I had predicted. Then, they’d message me about it. I tried not to think about it much, but inherently, I felt pressure when making those picks because I knew real money could be involved, based on what I was saying.

I knew my success at picking NFL games successfully was based more on luck than on skill, so I felt a sense of imposter syndrome when somebody told me they were relying on those picks. Piper, Gutierrez, and Christine Benz are familiar with that feeling.

“Oh, every single time I speak,” Gutierrez said. “I feel an immense amount of imposter syndrome for a variety of reasons for every audience that I get in front of. I’m here at [WCICON], and I’m learning from people as well. I’m in the profession, [but] every time I get up there, I think, ‘What do I have to offer?’ That’s where the imposter syndrome comes from.”

As Benz, the director of personal finance and retirement planning at Morningstar, told me after her WCICON26 keynote: “I would say my main area of imposter syndrome is in the non-financial aspects of all this, which I’m increasingly called upon to talk about in the realm of retirement planning—the psychology of it all. I’m not a psychiatrist, but the way I get around it is by talking to actual human beings. ‘How do you feel about this? What are your pain points?’ You learn a lot that way.”

Benz’s keynote was on The Numbers and Psychology of Retirement Spending, and Gutierrez and Piper spoke eloquently in their sessions (all of which you can watch in the Continuing Financial Education 2026 course that’s coming out next month). And all three dutifully and cheerfully answered attendees’ questions throughout WCICON. Here’s how they try to alleviate the pressure of always being right:

Stay humble, try not to speak in absolutes, and talk to the audience on an elementary level so they can understand 80%-90% of what you’re saying. Mostly, though, experts like Benz, Piper, and Gutierrez never stop talking to people, doing their research, and learning.

But they also know the weight of being right doesn’t go away. As Benz said during her keynote when talking about safe withdrawal rates in retirement, “We all stand on William Bengen’s shoulders.” If you’re not careful, all that weight on your body will drive you deep into the ground of despair.

WCICON26 Highlights

Although we've packed up everything from Las Vegas, we are still electrified from WCICON26, so let's reminisce about our favorite moments and highlights from this year’s conference, the seventh one The White Coat Investor has put on in person (and the eighth overall).

If you haven’t been before (or if you’ve only attended virtually), make plans to come in person to WCICON27 on February 24-27, when we return to Orlando at Rosen Shingle Creek. I made a bunch of new friends at WCICON26, rekindled a bunch of other relationships from previous conferences, gave plenty of handshakes and hugs, and had a blast overall. Like usual, just about everybody seemed really happy to be at WCICON.

Here were some of my favorite scenes from the week.

Some Reasons Why Docs Fail at Money

Dr. Jim Dahle started the conference by teaching the attendees exactly what not to do with their money. In his opening keynote, Jim listed 21 different reasons why doctors fail at money, why 25% of doctors in their 60s aren’t millionaires, and how people could avoid falling into those traps.

Here were some of the major reasons why doctors might not end up as wealthy as they should be:

Overspending: As Jim said, it’s not hard to spend $200,000-$500,000 per year if you make a good salary. “I have great faith in you,” he said to laughter. He also presented a slide from a recent survey that showed 40% of people making more than $500,000 are living paycheck to paycheck. Burnout: According to physician surveys, about 50% of doctors are currently experiencing significant burnout. Which is a major reason why we hold WCICON in the first place. “If you’re feeling a little crispy, you’re not alone,” Jim said. “You’re normal.” Divorce: Sometimes, people think they can get divorced to save money. But mostly, you lose half of your income and half of your assets if you split from your spouse. That’s why, Jim said, your most important asset protection insurance is to have date nights with your significant other. Bad investing behavior: Maybe you invest too much of your money in speculation. Maybe you gamble too much. Maybe you bought too many baseball cards. If you’re not putting your money into something reasonable, something that will make your money work as hard as you do, you could miss out on the wealth you want. You’re underpaid: You might know pediatricians who make as little as $150,000 per year or as much as seven figures a year. Half of the people in that specialty are being paid less than average. Don’t have an adequate plan for potential disability: We know that not enough doctors have disability insurance. That’s a huge risk for yourself and everybody else who relies on you to make a living.

Luckily, solutions to these potential problems exist. Here were some of Jim’s suggestions.

Know your worth: Many doctors work for less, simply because they didn’t ask for more money. As Jim said, you are not a better doc because you leave money on the table. Instead, keep up to date on the value of your skills and knowledge. Learn how to negotiate with your employers or potential employers. If you need help with that, WCI has got you covered. Plan your cash flow: This is one of the most important parts of financial planning. Tyler Scott and the team at White Coat Planning had a whole workshop about it (you can see it on demand in the WCI Events app, or you can watch it on CFE26). Said Jim: “If you’re not wealthy and you’re not doing cash flow planning yet at least once a month or once a quarter, that’s probably a big reason you’re not wealthy.” Your money needs to work as hard as you do: Remember, as Charlie Munger said, compound interest is your friend; don’t interrupt it. Don’t be afraid to own your business: We’ve written plenty about this topic, whether you’re a doctor or a dentist. Get a side gig: You can moonlight, you can be an expert witness, or you can start a short-term rental empire.

After the presentation, I asked Jim how it went and if people seemed receptive to his ideas. “Well,” he said, “they didn’t throw tomatoes at me.”

Going Mental

Paul Draper used to be a professor of anthropology, teaching college students about the world of human beings and how they behave. He only dabbled in magic. Until, that is, he got an offer from a client where he could earn more money in a month than he would make in an entire year as a teacher. Now, he’s a full-time mentalist, and he only dabbles in teaching anthropology.

On Friday, the second day of the conference, Draper was the headline performer, teaching us lessons about life while reading people’s minds. The ballroom was packed, and some attendees brought their spouses and kids to the show. He made me laugh so hard I started to tear up, he sang happy birthday to an attendee in Italian, and he did a magic ring trick while crooning Pure Imagination from Willy Wonka and the Chocolate Factory (meaning I had that song stuck in my head for the next few hours).

My favorite moment from Draper’s show came near the end when he taped coins to his eyes using gaffer’s tape and put a blindfold on his face to make sure he was completely in the dark. Then, he had two attendees, Dulce and Kelly, draw a picture. Just by listening to the way they used their magic markers, Draper successfully relayed what they had drawn. That was an alien in a spaceship from Dulce and a rainbow between two clouds from Kelly. It was probably the most impressive trick he performed.

Here’s another example from another time and place to see just how cool that performance was for those of us in Las Vegas.

Here’s hoping that next year, WCI can get Penn and Teller to headline a show.

Totally Tubular

At WCICON25 in San Antonio, the opening reception was a Texas theme, complete with belt buckles and cowboy hats. In Las Vegas, the opening reception was all about the 1980s, and WCICON attendees made us proud.

People showed up in their neon and side ponytails. I tight-rolled my jeans and put a red bandanna around my knee. My wife passed out T-shirt clips, jelly bracelets, and big lightning bolt earrings. And it was awesome.

One of my favorites was Justin Letkiewicz, the director of growth at Black Swan Real Estate, who looked like the lead singer of an ‘80s glam metal band. He had the blonde long-haired wig. He had the bandana across his forehead like Bret Michaels. He had the swagger. He said his favorite hair metal band is Whitesnake, and yeah, he looked like he could have been David Coverdell’s replacement.

But he wasn’t the only one who looked totally radical.

I saw plenty of MTV T-shirts and a few ladies sporting legwarmers. Somebody wore Lisa Frank-inspired pants. Another dude wore an 867-5309 T-shirt. Somebody else had a Save Ferris T-shirt (he clarified it was the movie, not the band). All of it left me wondering: When will Zubaz pants and big, crunchy hair finally come back into fashion?

Hello, Goodbye

One of my favorite interactions during the conference check-in process was with Peggy Kwun, a psychiatrist. I noticed that she was wearing a first-time attendee flag on her badge, so I asked if she was excited to make her WCICON debut.

“It’s my first WCICON,” she said, “and my last.”

“Your last?” I said. “How come?”

“Because I’m retiring in six weeks.”

So, raise a glass to Peggy, who seemed very, very excited that she’s almost finished working.

What were your favorite moments from WCICON26? Are you considering attending WCICON27 in Orlando?

The post Talking to Mike Piper, Christine Benz About the Pressure of Being Right (and Dealing with Their Own Imposter Syndrome) appeared first on The White Coat Investor - Investing & Personal Finance for Doctors.