Updated on 03.27.11

Illusions and Reality

Trent Hamm

An old friend of mine that I’ll call David has this amazing gift for talking to people of all stripes. I’ve seen him talk comfortably with a United States congressperson, a research scientist, an orchestra director, a janitor, and an unemployed person all within a few days of each other and build a quick rapport with each of them.

He achieves that rapport by doing a few things over and over again until they’re completely natural to him. He is never shy about talking to anyone. He starts off every conversation by asking two or three questions about the other person, putting them at ease and getting them to talk about themselves. He focuses on finding something positive in their situation – and when he finds it, it brings a big smile to his face.

The amazing thing about David is that he doesn’t achieve their respect by looking like he’s well-off or well-established. In fact, you’ll often see him in a well-worn sweatshirt, worn baseball cap, and blue jeans. He drives a fifteen year old pickup with some significant rust on the bottom.

One time, David and I discussed this, and he said (I’m paraphrasing from memory here), “People dress up and drive expensive cars to impress or intimidate others or to feel better about themselves. I don’t want to impress or intimidate others and I feel best when I’m just wearing something comfortable.”

David has a bunch of money in the bank and the ability to greet congresspeople by name. Do you?

Whenever I’m out and about, taking my kids to preschool or running some errand, I’ll see a wide variety of people. I see some people driving shiny new cars and others driving rusty old cars. I see some people dressed to the nines and others wearing raggedy old clothes. I see some people smiling and friendly, while others are glaring and surly.

Guess which one of those factors has the greatest impact when I make my mind up about someone? It’s not the cars. It’s not the clothes.

It’s the person.

There was a time in my life where the circle of people I hung out with appeared to be affluent. They dressed well. They drove nice cars. They had lots of gadgets.

Yet, most of them spent an awful lot of their time trapped in negativity. They would ridicule anyone not dressed well or anyone that didn’t match some very narrow picture of what they viewed as successful.

David, quite simply, would not have fit into that group at all.

Over time, I came to realize that it was people like David that were the successful ones, not the people in that group. Many of them were in debt up to their eyeballs. Most of them were having trouble moving forward on their career track and would often completely fall apart at the slightest setback in their lives.

Simply put, they didn’t have the money in the bank to sustain them, the connections to people that they could call upon, or the personal attributes that would make it possible for them to get back up on their own two feet.

My initial perspective was dead wrong. The people who appeared affluent weren’t really affluent at all. The people who didn’t appear affluent actually were.

What I came to find is that the initial appearance of a person often has little connection to their actual success in life, when by success I mean the goals they’ve achieved, the security they’ve earned, and the relationships they have with other people.

Usually, what I’ve found is that genuinely rich people appear in whatever way they feel the most comfortable, while people who aren’t truly affluent appear in whatever way they think others expect them to appear. This covers everything from clothes and haircut and automobile to personality and attitude. Sometimes, successful people dress well, while others dress extremely casually. The same is true for people who seem to be avoiding true success.

The next time you feel intimidated by someone you’d love to know or by some other social or professional situation, ask yourself what you would change about the situation to maximize your comfort. Would you feel better if you were wearing different clothes? If you drove a different car? If you had a good night’s sleep last night? If you were freshly bathed?

For example, I usually feel best shortly after a shower in a clean pair of jeans and a t-shirt, for example, preferably after about seven hours of sleep. I’m much more likely to smile at others and strike up a conversation with them if these elements are true, not because of how it makes them feel, but because I’m in the right mindset.

Don’t worry so much about what other people think. Instead, focus on putting you in the right mindset and you’ll go a lot further.

Warren Buffett is often seen wearing cheap suits.

Bill Gates looks most comfortable in a well-worn sweater.

The appearance of affluence has little to do with true success. People do.

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  1. valleycat1 says:

    I’m all for looking beyond appearances in deciding who you want to associate with – my spouse is one of those who often looks like a homeless person because he works outside on our farm doing manual labor, machinery repair, etc. So we’ve experienced the automatic disrespect that an unkempt appearance can engender, even from family members who should know better.

    However, it cuts both ways – just because someone dresses well, lives in a big house, or drives a nice car doesn’t automatically mean they’re in debt up to their eyeballs or not a nice person. No need to be intimidated, but also no need to make a negative assumption about them either. My grandad, for example, was most comfortable in a nicely tailored well made suit, and was a very charming person living an honorable & financially sound life.

  2. Kathryn C says:

    I see Al Bundy where I get my coffee every morning. He wears sweats and drives a beater, not kidding. He sits and talks to all the locals at the coffee shop every day. And he’s worth a gazillion dollars.

  3. Rachel says:

    This hits home with me. I have everything I need, but still I go out and spend money because I am with my mother, who likes to shop, or trying to look and dress like the other women I see at church. You would think that at 47 years of age I would be well beyond feeling the need to fit it. And we wonder why our kids feel so much peer pressure? I am working to get to the point that I am my own person, living my life to suit me, not my peers or Madison Ave.

  4. VickiB says:

    I don’t know – I see both sides of this. I LIKE to look nice – it’s just me. When I got my first job at 16, I went to the mall and bought a gray wool pinstripe suit and wore it for years. I am nice to everyone, but I don’t consider myself a snob when it bothers me that people now go out in public to the store wearing dirty dragging pajama pants with the kind of flip flops they issue in prison? For me, it’s about SELF respect. Do I look like a refugee hoeing in my garden? – YEs and amen ! But call me superficial, I wish people could at least try to be clean and wear clothing that fits when around others. Sorry – maybe everyone else here is just more “evolved” than me !

  5. Gretchen says:

    What’s wrong with wanting to make a nice impression?

    You just judge the other way. That the BMW driver is drowning in debt- you don’t *know* that.

  6. Tracy says:

    This is absolutely one of the worst posts I’ve ever seen! It doesn’t even make *sense*.

    You start off by talking about how nice/friendly David is.

    Then you say basically, all surprised, that he just looks like a regular, non-wealthy guy

    Which, I don’t understand your reasoning here, but you seem to expect readers to be surprised/shocked by the fact somebody can be nice and friendly and not wear a fancy suit? what? “The amazing thing about David is that he doesn’t achieve their respect by looking like he’s well-off or well-established.”

    There’s absolutely NOTHING amazing about that!

    Anyway, then you present your second non-shocker…David has money! He just doesn’t look like it!

    And you then jump to the conclusions that if you have money, you don’t look like you do, and if you look like you have money, you’re probably in debt which just … so random and nontrue.

    Plus, you throw in a bonus “Whenever I’m out and about, taking my kids to preschool or running some errand, I’ll see a wide variety of people. I see some people driving shiny new cars and others driving rusty old cars. I see some people dressed to the nines and others wearing raggedy old clothes. I see some people smiling and friendly, while others are glaring and surly.
    Guess which one of those factors has the greatest impact when I make my mind up about someone? It’s not the cars. It’s not the clothes.

    It’s the person.”

    No, it’s not. It’s your own preconceived notion of the person. You don’t actually KNOW them, or their reasons. So why are you making up your mind about total strangers at all?

  7. Johanna says:

    So, based on whether a stranger is “smiling and friendly” or “glaring and surly,” you “make your mind up about” them and decide…what exactly? How much money they have? (How does that follow, and more importantly, why do you care?) Whether they’re a nice person? That makes a bit more sense, but still, there are lots of people who act “smiling and friendly” but are *not* genuinely nice people – they’re just skilled at the art of laying on the charm in order to get what they want from you. And the “glaring and surly” person might just be having a bad day. Or they might be unhappy about something in particular. Or they might be uncomfortable interacting with new people, but if you take the time to get to know them, they might be genuinely nice.

    Also, Warren Buffett and Bill Gates’s clothes are a pretty bad example. They’re both famous enough that they don’t *need* to dress a certain way to convince people that they’re rich – everyone already knows that they are. From what I understand, Bill Gates conspicuously displays his wealth in other ways – he lives in an enormous house, for example. And even Warren Buffett’s famously modest house is only modest by billionaire standards – if it were owned by anyone else, it would be considered a mansion.

  8. Matt says:

    This is the absolute last straw for me. I was turned on to this blog due mostly to its past content. Lately it seems more like a content farm with uber-specific mailbags and the same points repeated ad nauseam. Being frugal does not give you the right to be this damn self-righteous! I know you never read these Trent, but just know that you just lost a regular reader with this post.

  9. marta says:

    Here we go again with the assumptions…

  10. Adam P says:

    “He drives a fifteen year old pickup with some significant rust on the bottom.”

    Since we’re making massive assumptions, I’ll say “David” hates the environment or he’d get his dilapidated jalopy off the streets and buy something with cleaner exhaust emmissions that burns less fuel.

    @#8 Matt—come on it’s still fun to see where Trent will go next!


    A Childless Candle in the Wind with a $60 swimsuit

  11. marta says:


    A Childless Candle in the Wind with a $60 swimsuit”

    Adam, I can’t make my mind up about you based on those tidbits alone. Do tell, do your bathroom curtains match the towels?

  12. JS says:

    I think this post is written in a rather clumsy manner, but the point is valid- when evaluating wealth, appearances are virtually useless. Thanks to all the ways you can get in debt, it’s very difficult to evaluate someone’s financial health just by looking at them. To paraphrase The Complete Tightwad Gazette, a huge diamond stands out, while a ten-year-old suit and a healthy bank balance don’t.

  13. Troy says:

    Trent. You have got to get over the judgemental attitude. It will destroy your blog. Sometimes things are just as they seem. Sometimes they are not. That is just the way it is.

    Some people that look successful are successful. And some are not. Some people that look poor are, and some are not.

    The real question is why do you care. Instead of trying to figure out and discuss your thoughts on others, why not figure out why you give a hoot in the first place. Who cares what anyone else drives or wears or says or does.

    If you want to judge someone, look in the mirror…then stop.

  14. Andrew says:

    I’m beginning to believe that Trent writes the most clumsy and wrong-headed entries to his blog as a public service–just so that he can get a string of highly entertaining reader comments going.
    I love the fact that I can completely disagree with someone here about one thing, and then turn around and read their wonderful, thoughtful opinions about something else. I also love the back-and-forth discussions (arguments?) that erupt all the time.

  15. Tracy says:


    Haha, you know, I’ve thought more than once that Trent’s unique talent is how easily convince me that he’s absolutely wrong – even when I agree with his starting premise.


    Thank you for saying what I wanted to say, far more eloquently than I ever could.

  16. Steven says:

    I think it really depends on how a person defines success and how they don’t, and how a person finds fulfillment and happiness in their life. For some, it might be expensive clothes and shiny cars. For others, it’s family and relationships. The real point, though, is to just be happy with your own life, not worry about others, and don’t judge people based on their clothes (expensive or cheap) or any other material possession. What a person buys doesn’t define them, and people who own nice/expensive things are probably not all that broke as you might think. Just because that’s the way your life worked out doesn’t mean that’s the story for everyone.

  17. jackson says:

    Insigtful post. This article reminds me of the book, “The Millionaire Next Door” by Stanley and Danko. Wealthy individuals often don’t look wealthy because they don’t spend their money on expensive cars, big houses, or fast cars. People that do buy those items are often drowning in debt.

  18. Nate says:

    I really appreciate this blog, but I often feel that Trent completely disregards people who genuinely care and get personal fulfillment out of dressing nice or driving a nice car. Hasn’t he said time and time again that we should spend money on the things we care about and be frugal in areas that we don’t? So what if some guy cares about wearing a nice suit? Maybe he lives in a small apartment with old furniture because those things aren’t important to him. While I appreciate what Trent was trying to accomplish with this post, it seems lately that he’s been very down on people who care about things he doesn’t care about and makes some broad assumptions about them.

  19. lurker carl says:

    Regardless if that person is homeless or my elected government representative, I build my first impression upon their state of mind rather than their finances: Are they are sober, drunk, stoned or crazy? I couldn’t care less about someone’s financial status whether it is based upon outward appearance or their own words. But I do care if their brain is in the same time zone with the rest of their body.

  20. Maureen says:

    I think it is equally wrong for you to decide that someone is NOT affluent because they dress well.

    I actually try to dress appropriately for the context. I would not wear the same shirt I wore to mow the lawn if I were going to a business meeting or a wedding. Casual clothes are comfortable but they are not always appropriate. Many places of employment have dress codes. Some people may just enjoy fashion. Some people are very good at investing in a good quality wardrobe of basics that can be worn for many seasons without looking dated.

    I’m sure that Bill Gates and Warren Buffet can and do dress to the nines when appropriate.

  21. jim says:

    Don’t judge a book by its cover.

    Either way, good or bad.

  22. Lex says:

    I’m just starting my career as a contractor and I must say – it gives me such a confidence boost to be wearing a nice dress and heels. My outfit isn’t the most expensive, but it wasn’t cheap either (in fact I pretty much spent my earnings of the day on my outfit but I can use it for years to come)
    I might have been more comfortable in jeans and a T-shirt but not nearly as confident AND it wouldn’t have been appropriate attire for the circumstances.

  23. Rob says:

    Not for nothing, but the richest guy I know has never worn a suit in front of me. The most formal thing I’ve ever seen him wear is a button down shirt and slacks, and that was at a holiday dinner at a nice restaurant. He also drives a 20 year old car. Sure, it’s a 20 year old Mercedes, but he could definitely buy a new one. He owns a house on the waterfront in Orange County and has spent the last ten years traveling the world with his wife. The guy is obscenely happy, easy to get along with, and one of the nicest people I’ve ever met.

  24. deRuiter says:

    Read “The Millionaire Next Door” which covers this idea wonderfully. A rich person can dress poor or he can dress modest, or rich. Lots of people who look rich are struggling with debt. Many American millionaires are rich because they and their spouses were /are thrifty. You don’t have to dress like a homeless person to be thrifty, use elegant clothing from yard and estate sales, and have it tailored. if you’re mucking out the horse stalls, you wear rubber boots and old jeans.

  25. Annie says:

    I have mixed feelings about this. I love to see people dressed up and look clean and neat. I think they work hard to accompolish the look and they deserve to be respected. What i don’t like is the assumption that everyone that has nice cars or dresses nice is in debt. That is a true misconception. There is nothing wrong with wanting to look nice or wear a nice suit to work. I think it shows that you care about the way you look and you carry money nicely. I see a lot of posts not just from your website that makes it look like everyone that has nice things and drives a nice car is in debt and i think that is a disgrace. My dad told me before when you start working if you make good choices in your life, you can have the nice car, the nice clothes and the savings you desire it’s all about being responsible and keeping a job where you give a 100% so you can grow. I actually am turned off to someone that is not dressed well, it makes me wonder why they don’t care about themselvles to look good. What is the beauty in a worn sweater over a J.Crew sweater that is new and never been worn. I try to be aware of my spending, i save a lump sum every paycheck and leave a balance for me to spend, the balance i spend is whatever i want, coffee at starbucks, a new shirt, toy for my dog, plan for my trip overseas,etc… You have to live life to the fullest!

  26. Annie says:

    I forgot to add this but Warren Buffet also has a mansion in laguna hills that is not advertised as much. There is no way Warren Buffet and Bill Gates don’t have an armani suit in their closet. It’s just unreal and i don’t believe it. I agree with the person that said they dont’ have to dress well to impress becasue they are already successful.

  27. getagrip says:

    When people talk about the people who look rich but aren’t, they often forget about the fact that there are many people who look rich and are, i.e. if one out of three homes in a particular neighborhood is inhabited by folks who are struggling to keep up with the Jones’, then two out the three homes in that neighborhood *are* the Jones’ and are doing just fine.

    I’ve found that you need to dress for the occasion and depending on how well known you are to the folks you’re talking to. If “Dave” came into a venture capital meeting at a corporate office looking for ten million to invest in his business wearing a baseball cap, old sweatshirt, and jeans, chances are he would have a tougher sell than if he put on a decent suit and tie. If he was talking one on one with the owner of a marina up for sale out on the dock he could probably swing a deal easier dressed more casually than wearing a suit.

  28. Jules says:

    Gotta agree with people who say that assuming that someone with a nice car is in debt is equally as shallow as assuming that someone dressed in sweats and blue jeans is poor. I mean, for Chrissakes, I write about eating €200+ dinners–doesn’t mean that we pay for it with a credit card.

  29. Danna says:

    I totally agree that Trent is off the mark here. I hate how casual our society has become. I hate flip flops! I have a co-worker that dresses horrible, no make-up, hair in pony tail and she wonders why she hasn’t been promoted.

  30. Marie says:

    When friends and family complain about not having any money because they are making $600 per month car payments on a $40,000 gas guzzler SUV with all the bells and whistles, I just can’t feel sorry for them. Personally I’d rather have my money in the bank than in the garage…

  31. jessie says:

    I don’t see why it matters whether people should or should not judge you based on your clothes or car. They do. And @Johanna, you’re bang on about Buffet and Gates – those guys can wear and drive anything and it wouldn’t matter because they’re already rich and powerful. If I show up to work in ratty jeans and a sweatshirt I DEFINITELY don’t get promoted, because it’s a statement that I don’t care (especially because I am young and early on in my career). I think this is totally a ‘new American’ trend towards wearing the worst you can get away with, whereas historically in many cultures, people WANT to wear their best, look their best, and in so doing show respect for themeselves and others. Does this mean dropping millions in clothing every year? No. This post reads like your only options are fancy suits and cars or jeans and worn sweatshirts though, which obviously is not true.

  32. Kathryn says:

    “Don’t worry so much about what other people think. Instead, focus on putting you in the right mindset and you’ll go a lot further.”

    Best line in the post.

  33. Nikki says:

    I have to remember to not bother reading the comments on Trent’s blogposts, and I can completely understand why he’s (for the most part) stopped reading them (or at least stopped responding to them)

    The main point of Trent’s post is, it doesn’t matter how you dress. It’s how you treat people. If you dress in clothing from Saville Row because you love dressing that way, and can afford it, great. If you dress in clothes from Kmart and enjoy it, fantastic.


    If you are dressing to impress OTHERS, you won’t impress anyone (or you’ll impress them for the wrong reasons). If you are dressing to INTIMIDATE others, you really need to take a better look at yourself and figure out why you feel the need to intimidate.

    If you love the way you dress, that’s the best way to be. Now, go out and treat others well, no matter HOW they are dressed.

  34. Interested Reader says:

    Nikki the problem is *Trent* judges people by how they dress and what kind of car they drive.

    At least he has consistently in the past said that people who have nice cars, nice houses, and wear nice clothes are probably in debt and over their heads.

  35. AniVee says:

    This post started off about the Mythical Friend “Dave” achieving a rapport with people of all economic classes- and then veered off into Snap-Judgment-Land on dress, vehicles, financial solvency, character and putting yourself in the right mindset.

    I have read and re-read The Millionaire Next Door and I also believe there is little correlation between appearances and net wealth, a subject that has certainly be beaten to death lately.

    For me, the most interesting part of the blog is how the “rapport” is established by “Dave” – and here Trent jumps to the precarious conclusion that Dave “achieves the respect” of the people he successfully converses with, and goes on to say that Dave is successful and “has a bunch of money in the bank.”

    Rapport may not always equal Respect, but it would seem that for Mythical Dave, Rapport may well equal Success/Money/”the ability to greet congresspeople by name”.

    This reminds me that back in the Woodward/Bernstein/Watergate Era I read that successful investigative reporters and detectives who go out to interview people and investigate a hidden subject found that they NEVER were very successful if they came on to the interview subjects or neighbors as too “polished, well-dressed or (emphasis mine) educated…” –
    their grammar couldn’t be too perfect, either…
    One is instantly reminded (and here I am REALLY revealing my age…) of Peter Falk as “Columbo” with the rumpled trench coat. The investigators and reporters were, of course, manipulating the subjects into giving up needed information and were often “successful” at it.

  36. Interested Reader says:

    @Danna, what’s wrong with wearing no make up? I can understand if your co worker is not dressing professionally but why should make up be a requirement?

  37. Sheila says:

    When I first started to read the article, I thought it was going to be an article about how to talk to other people.

    The advice about asking the other person two or three questions about themselves to put him/her at ease and to focus on finding something positive to say about the other person’s situation are wonderful ideas. I guess that another tip is to be comfortable with who you are and not be insecure about yourself — it’s okay to talk to a senator even if you’re wearing comfy jeans and a sweatshirt. I will certainly keep those tips in mind when I am out and about.

    I wonder if Trent would write a longer article with tips like this, perhaps giving examples to illustrate the point. I would certainly enjoy reading that and trying out the tips to see how good I can become at communicating with other people.

  38. Julie says:


    I am with you. I think that some people are incredibly over sensitive to virtually any comment that Trent makes. His comments are generalizations and best selling books, such as “The Millionaire Next Door” have been written on this exact same subject. That doesn’t mean Trent is judging anyone. He is merely stating that not everything is as it appears to be.

    When you live in the heart of Orange County California you would have to be an idiot to not realize that very little is what it appears to be. This doesn’t mean that you are judging people. You are just making observations. Making observations and coming to conclusions is a daily part of life, and I am coming to the conclusion that many readers of this post just don’t share the same opinions on frugality as Trent…and it is time that they move on to a post that is better suited to whatever it is they want to hear and won’t leave them feeling so terribly offended.

  39. Julie says:

    I drive a $50,000+ car because it is provided by my company. Nobody has ever asked me what my car cost, but many have asked me what my monthly payment was.

    Also, an interesting statistic was printed in the Orange County Register just prior to the start of the recession. One of the largest Mercedes Dealers in the country, which is located in Newport Beach California, disclosed that about 70% of their business came from leases. The reason the dealer stated as most common for a lease was that a customer could not afford to purchase the car. Leasing was their only option. This would seem to support the theory that most (most equals more than 50%) people who are driving expensive cars really can’t afford them… I wonder if the dealer was “judging” their customers???

  40. Nicole says:

    It’s funny, I just had a feeling people would come down hard on this post. It’s rather predictable. I re-read it trying to find the place where Trent was being overly judgmental, and couldn’t find it. He draws on personal experience and makes it clear (or so I thought) that it’s difficult to generalize.

    About surliness and “bad days” — well, I’m sorry but I think the stat is that first impressions are made in about 15 seconds or something like that. I may be able to remind myself to look beyond appearance, but if you’re going to take your issues out on other people you’ve barely met, that’s a whole other story. How exactly are you going to make that up to them? Most of the time you only get one shot.

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