Are You Smart Enough To Act Dumb Enough To Get Ahead?

Are You Smart Enough To Be Dumb Enough To Get Ahead?The smartest people in the world are listeners, not speakers. If all you’re doing is speaking, how do you learn anything new?

There was once this portfolio manager I covered who had this uncanny ability to make you feel uncomfortable without saying anything at all. He had a poker face when you spoke to him, and when he felt like changing expressions, he’d go from solemn to smiles in a millisecond. We nicknamed him Crazy Eyes. It turns out that he was literally a genius with an IQ over 160. He also consistently beat his index benchmark for eight years in a row and made millions because of it.

The earliest examples of acting dumb to get ahead starts in grade school. You know what I’m talking about. Those kids who were too cool to study and too cool to sit still in class as they flicked spitballs from the back of the room. These kids weren’t just acting dumb, they really were dumb.

When you purposefully waste your opportunities growing up, you’re not only disrespecting your parents, but also the millions of other kids around the world who will never have the same opportunities.

This post will do the following:

1) Argue why acting dumb is a smart move to get ahead.

2) Provide some tips to help you look and seem a little dumber than you are.

3) Share three personal examples of how acting duhhh, has helped in work, stress management, and relationships.


There are three main reasons why acting dumb will help you succeed in life.

1) You no longer become a threat. If you have ever competed in sports, debates, game shows, or worked in super competitive industries such as finance, consulting, or law you know how cutthroat everybody is. Someone is always gunning for you if you are one of the top dogs. Online entrepreneurship is even more competitive because the barrier to entry is low, and ideas get stolen all the time.

When you are considered dumb, or at least not a threat, people stop looking to undermine your abilities. It’s natural for anybody in the work environment to feel threatened by a new hire, a lateral hire, or a superstar colleague. We all have our insecurities. The more you can pretend not to know as much as you do, and the more you can include other people in your successes, the better you will be.

2) You can more easily surprise on the upside. Getting ahead is about underpromising and overdelivering. Eager people have a tendency to overpromise and put so much stress on themselves that they underdeliver instead. The key is to contain your pride by highlighting 80% of what you can do, and deliver 81%+.

I remember improving in ranking with one client from #10 to #6 and getting praised for the move. Then with another similar client I slipped from #3 to #5 and was admonished. Because I worked for a large firm, we were always expected to be in the top 3 with clients, even though only three firms can be in the top three! But if you work at a lesser tier firm, or even a bucket shop, then just getting ranked in the top 10 was good enough.

3) You’ll have a much happier life. When you’re constantly expected to be the best, you’re setting yourself up for failure. Everybody eventually has a misstep or loses some steam at some point. The goal is to find that steady state where you can continue to progress while giving yourself room to progress a little more.

A big part about building wealth is longevity. If you burn out 20 years too early, or before your peak performing years, you’ll have a serious financial deficit to make up if you don’t have a plan. Like the Stealth Wealth concept, you don’t want to stick your head out too far out of fear of it being cut off by the government, your jealous colleagues, or nefarious characters looking to rob you blind.


Acting dumb is easy for me because I’m pretty dumb in a lot of things e.g. college level math, art, history, languages, making women stop hating me, and so forth. Just read some of the comments some lovely readers leave telling me how dumb I am for proof!

But there used to be a time when I just couldn’t help but brag about my achievements. And when you start bragging about your achievements, people start hating your guts. When people start hating your guts, you get into fights in school (check), your business model gets stolen (check) and you get passed over for a promotion or a raise (check).

The higher up you go in any work organization, the more collaborative you must be. It’s all politics up there. The “superstar syndrome” is a dangerous syndrome to exhibit because everybody higher up will act in unison to keep you down, even if you’re a pretty nice person. The one tip I can give is to NEVER use the word “I” when sending an e-mail or giving a talk about some successful business win. Always, always use the word “we” and point out individual’s names that helped make the work win a success.

If it was truly only you who made something special happen, then acknowledge the support of your boss and teammates anyway. They’ll know they had nothing to do with the win, but will appreciate your shout-outs anyway.

When we are younger, we tend to always think that we know more than we really do. Humble pie takes time to eat because it tastes disgusting. Once you eat it, you’ll stop trying to look so smart to everybody. And if you haven’t eaten any humble pie yet, then hopefully you’ll take my advice to heart.


1) Dress to look younger. You’ve heard the advice to “look sharp” haven’t you? Well dressing one or two levels higher than your peers and boss is a surefire way to get your hands chopped off. Never dress more than a half-step more than your position. These steps are subjective, but if you pay careful attention to what people wear in the office, you’ll understand.

I currently go to work in jeans, a t-shirt, a baseball cap, and a long-sleeve fleece jacket most of the time. In other words, I look like a student even though I’m 37 years old. Being treated like a younger employee than reality is just fine by me because many of my colleagues are under 30 years old as well. Everybody dresses casually, so I fit right in. It’s also about aligning compensation and expectations so you aren’t miserable.

It’s hard for senior management to see me as an ex-Wall Street executive who ran a large business for 10 years when I come in dressed so casually. It’s hard to see that I’ve built an online business from the ground up with consistent margin expansion and operating profits that would make any entrepreneur proud. What they see is a friendly face who is happy to help, do his contracting job, and provide some occasional insights when asked upon. A larger role for me isn’t really in the cards largely because of the image I portray.

Looking younger doesn’t necessarily mean you will appear dumber. But there’s sometimes no amount of intelligence that can make up for a lack of experience. So if you can mold yourself as looking less experienced, then you will naturally seem less worthy of bigger roles.

2) Alter your speech. It almost doesn’t matter what you say in a British accent, you will still sound pretty sophisticated. It almost doesn’t matter what you say in a valley girl or a surfer dude accent, you will sound a little less sophisticated. The way you speak has a tremendous impact on how others perceive your intelligence.

The main ways to alter your speech to make you look dumber is by adding the words “like” and “umm” in your sentences. If you want to take it a step further, include rhetorical questions such as, “You know what I’m saying?” multiple times. The listener will start getting agitated and think to themselves, “No I don’t know what you’re saying you idiot!”

Clearly you must remove SAT type words from your vernacular as well. Unless you are Fraser Crain, nobody speaks with words like “pernicious,” “erudite,” “colloquial,” “nadir,” “vapid,” “boorish” and so forth. Practice speaking like a middle school student and you will do just fine, yo.

3) Slow down your response times. Don’t be quick witted and answer questions in lightening pace. Pretend like you are still calculating answers like a 286 computer instead of the latest microprocessor that you are. I’ve found myself very agitated when a friend of mine takes a long time to answer a question or recall a song name or whatever. He is clearly very smart, but because his response time is slower than mine, I automatically think he’s dumber than me even though I’m wrong.

The key is to not be so slow as to annoy the other person. During your time of rumination, you should utter phrases like “hmmm,” and “let me think” to keep the other side engaged. You can start answering the question in a round about way, until you finally zero in on the point. Better yet, let them answer their own questions to make them feel smart.

4) Smile a lot. You’ve heard the saying, “I’m going to wipe that dumb grin off his face!” right? People associate smiley people on the dumber end of the spectrum. Furthermore, smiling a lot will make you look less menacing. People will naturally smile back at you and wonder why the heck are you smiling all the time because work generally sucks! You never see an evil genius smile. They are either smirking or plotting with a furrowed brow.

5) Look a little frumpy and out of shape. Even if you are clearly an intelligent person, showing some physical weakness will help people think a little less of you. The worst is to be physically fit, attractive, eloquent in speech, intelligent in answer, and extremely hard working. You are going to be gunned down before you know it because you are a threatening machine. Buy some shirts and pants that are one size too big. Don’t cut your hair for a long time. Wear some mismatching outfits.

6) Just pretend you don’t know. If you know a lot of stuff then a lot of people will come to you for questions. You’ll be so inundated with questions that you won’t be able to get your own work done. People tend to take advantage of your time once you show a little bit of kindness. For example, I’m constantly answering e-mails from people who have personal finance questions. I would say 90% of the time I respond with a thoughtful answer. And when I do, they will ask for another answer and want me to get into more detail. So instead, I sometimes pretend I don’t have an opinion or I don’t know when an absolute stranger who has never commented here before asks me questions.

The more other people know how much you know, the higher the expectations they have of you. And if for some reason you don’t have time, or you’re past your allotted work hours and don’t want to help, they might develop a sour opinion of you if you don’t spend your remaining free time helping them out en gratis.


* Work. As a blogger for the past five years, of course I know about SEO, social media, marketing, earning online income, and writing content. Every company’s marketing department should hire veteran bloggers because content marketing is huge in the internet world. No longer do people want to just view ads. Consumers want to digest content that provides value before signing up for anything. Strong content helps build a brand and create goodwill. Bloggers have the ability to build a community, embolden a brand, growth hack with no budget, write engaging content, and understand analytics.

For my consulting gig, I went above and beyond for my first three month contract, working 40+ hours a week instead of 25 hours a week  in my contract because I have a tendency to try and always over-deliver. But I realized after three months that the more I do, the more I’m asked to do until the work hours could easily extend to 60 hours a week. It’s really hard to stop for all parties, once we get going because there’s an endless amount of things to do in startup land. Those who’ve followed me for a while know that I have workaholic tendencies that can easily manifest itself with some prodding. Heck, this post is over 3,000 words long. Who does that, but workaholics!

My current role as a consultant is to manage a team of writers and write content. I’ll help where I can on other things of course, but I will easily blow past my contracting hours if I’m tasked to do SEO, manage the social media platform on a daily basis, and provide copy writing for advertisements and landing pages. I’ve had a lot of fun testing out paid content promotion for various things I’ve written, but doing all that is a full-time job, which I don’t have. The solution is to therefore bring down my work hours to be better aligned with our agreement, or renegotiate my next three month contract for a higher amount. That wasn’t going to happen given I just started.

I’m optimizing for a better lifestyle where I can get paid for good work performed, interact with smart and fun people, and also have a good amount of freedom. I don’t mind consistently giving 120% effort in what I do (20% more time than agreed upon). But giving much more than 120% over an extended period of time feels off since I’ve got plenty of other things I enjoy doing. I’m currently in a happier place now because things are more balanced. If I do decide I want to work full-time again, it’s easier to surprise on the upside by demonstrating my entire repertoire of knowledge and skills.

* Investing. If you want to grab someone’s attention just tell them you work or worked in finance and they will pick your brain non-stop for investment ideas. They’ll ask you about the next hot IPO or your views on the Federal Reserve’s latest interest rate policies and how it will affect cyclical stocks. They’ll ask you to analyze their current investments and see if you have recommendation for where they can rebalance. When it comes to getting advice on making more money, people can’t get enough.

Of course I’m going to do my best to help my friends and family when they’re in need, like I spent several hours helping my sister come up with a financial plan last year. But I hardly ever tell anybody that I used to work in finance. I just tell them I’m a writer instead. The benefit is I won’t get asked for investment advice and I won’t have looks of disapproval about working in finance. Money has a terrible way of getting in between relationships, and that’s the last thing I want money to do.

When folks start highlighting their great investment wins, I simply listen in, congratulate and smile. And if people find out my background and want to really get down and dirty with their finances, I’ll happily refer them to my personal finance consulting page. Some people really end up wanting to work with me after finding out that I never bothered to advertise my services in the first place. Funny how things work some times.

* Relationships. Great relationships are hard to come by. They take work and a whole lot of listening. I really enjoy making friends with people from all over. But my biggest problem is still coming across as overconfident and a know-it-all type with younger people I meet. I have this automatic desire to teach and mentor younger folks because I’ve seen their movie before and I don’t want them to fall into the same holes I fell into. I also come from a culture where respecting your elders is of great importance, so I just assume that whatever I say to a younger person will be heard. Unfortunately, my desire to help can come across as arrogant, particularly in America. Many people don’t want mentors or teachers, they just want to be equal friends. Who wants advice about things when they haven’t asked? Nobody.

By pretending to be in the dark about many things a new or younger person discusses with me that I know about, I’m able to reduce my arrogance and create a more equal relationship. As the relationship progresses, I can adjust accordingly. And if there’s a massive trap a friend is about to walk into, I’ll definitely step up and provide some guidance. I don’t have this arrogance problem at all when I’m hanging out with older people due to my customs. I think I’ve been able to develop healthier relationships with more people over the past five years.

I’m really trying to work on better self-awareness. Developing better relationships is so important that I have a dedicated Relationships category. Lots of personal stories here, so be forewarned.


Instead of pretending to be unknowledgeable or a little dumb, demonstrate that you have so much vigor in your craft that people are intimidated by your presence. Because you are a rockstar who is clearly crushing it, other people don’t want to waste your time with dumb questions they can look up online, so they never ask. Because you are vital to your organization, management knows they can’t screw you.

You want to be a nice and collaborative person no matter your real intelligence. But if you’ve found a happy balance in your life and have a reasonable amount of intelligence, then acting dumb might very well be a great way to keep your happiness going for an extended period of time.

Related Posts:

How To Get Haters To Stop Hating You

The Stealth Wealth Movement

Things To Do Before Quitting Your Job High Roller

Readers, have you ever acted dumb to try and get ahead? What do you think about the concept of acting dumb to get ahead? Do you think those who try to act smart aren’t really that smart? 

Looking to make extra money? I’ve recently tried out driving for Uber because they were giving away a free $50 gas card and are currently giving up to a $300 bonus after you make your 20th ride. After 25 hours, my gross pay is $32/hour, which is not too bad! I can see how people can easily make an extra $2,000 a month after commission and expenses with Uber or any ridesourcing company. I’d definitely sign up and drive until at least the bonus . Every time I plan to drive somewhere, like my main contracting gig down in San Mateo, I’ll just turn on the Uber app to try and catch a fare towards the direction I’m going. Why not make extra money?

$32/hour is a huge pay cut for me and it’s a humbling experience as well. But discovering the whole ridesourcing experience first hand is fascinating! I’ve got so many stories to share in the future about my experiences picking up random people. You can make $40,000 a year easily if you work a normal 40 hour a week shift based off my experience. Nowadays, if I’m going to some low key party and don’t want to stand out, I’ll just say I’m an Uber driver if someone asks what I do!


Sam started Financial Samurai in 2009 during the depths of the financial crisis as a way to make sense of chaos. After 13 years working on Wall Street, Sam decided to retire in 2012 to utilize everything he learned in business school to focus on online entrepreneurship. Sam focuses on helping readers build more income in real estate, investing, entrepreneurship, and alternative investments in order to achieve financial independence sooner, rather than later.

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  1. bex says

    I used this trick in High School. The people at the top of my class were extremely competitive with rank and such. If they knew you were smart they would do everything possible to ruin you. So I did things to make myself seem stupid. I kept this up all four years. It was funny to see the people who thought they were so smart actually fall for my dumb act. It worked, no one considered me a threat and I graduated 9/280 and had the highest SAT score in my grade. It all worked till the end of my senior year when the school started announcing this stuff. My cover was blown when they announced who was in the top 15 of my class. Let me tell you those kid’s faces were hilarious. Watching them realize I was smart all along was so funny. Some people still didn’t get I played dumb and that just shows how stupid they were. As much as I hated dumbing myself down it was funny and honestly saved my academic life.


  1. […] 8) Pretend you do not understand. You might be a brilliant person, but brilliant people are intimidating. Instead, pretend you don’t fully understand what another is saying by asking questions. Don’t think you’re better than others just because you see solutions easily. Guard your intelligence like you guard your full income and wealth. It’s better to start your intelligence at a base level and dial it up if the occasion requires. Some of the smartest people I know have this eery look about them that screams stone cold aloofness. You know they are already thinking multi-variably, but from the outside it seems like they are a dull brick wall. Read: Are You Smart Enough To Act Dumb Enough To Get Ahead? […]

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