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Always Be The Underdog To Get Ahead

Updated: 05/25/2022 by Financial Samurai 61 Comments

If you want to get ahead, always be the underdog. You will be much happier if you do. If you are the underdog, nobody expects you to win. But if you do, you will gain a tremendous amount of satisfaction.

Deru kugi wa utareru is a Japanese proverb that means, “The nail that sticks out gets hammered down.” In other words, stand out too much and you become a marked person. I wholeheartedly agree with this proverb, and live by it until it’s time to make a move.

Unless you are an egomaniac who just can’t get enough attention, it’s good to be the underdog. You can walk around freely and nobody will ever notice you.  As the underdog, you always have the chance of surprising on the upside as well. 

Nobody expects you to do amazing things coming out of community college. However, if you go to Yale University you better do something great, or else! There are plenty of Ivy League graduates who end up as nobodies.

Let’s go through some common scenarios and discuss why it’s great to be the underdog.

On The Job Underdog

When you first start off at a new job, there is a tendency to show how knowledgeable and great you are. Don’t.  

It’s important to pay your dues. Keep your special opinions to yourself until you have the complete trust of your colleagues.

If you’re a low level employee driving to work in a fancy car, don’t. Why on earth would your boss ever promote and pay you if you seem to have all the money in the world? Your colleagues are going to be jealous and push you down.  Instead, drive a beater or take public transportation.

You might know more than your senior colleagues, or at least think you know, but do not try and outshine them. Instead, use your knowledge to help them shine.

Stay Stealth Wealth Underdog

If you are making a substantial amount of money, or at least more so than your friends or colleagues, don’t ever tell them how much you make.  Many a solid relationship has been lost over the knowledge of one’s income. 

It’s human nature to compare yourself to others, and if you’re making twice as much as your friend, your friend’s resentment will fester.

Instead, it’s important to give the impression that you make less than everyone you know.  You will garner sympathy and nobody will see you as a threat. 

People will root for you, and when you offer to buy lunch, they will be extremely touched.  If you’re wealthier than them and don’t offer to pay, they will resent you.

Related: Adopt Stealth Wealth To Stay Hidden From Society’s Rage

Stay The Underdog In Sports

Unless you have obvious physical attributes which can’t be hidden i.e. 7 feet tall, make your opponent feel at ease and downplay your own skills.  Talk about the injuries you’ve sustained as well as your embarrassing losses.

Do not mention that you train 5 times a week, played competitively in college, and can run a 4 minute mile. 

Instead, just mention that you’ve been playing for a long enough while to develop some seriously bad habits.  When you’re going out with clients to play golf or tennis, for example, they will truly appreciate your humility and recognize your striking skills for what they are.

See: When People Doubt You, Just Keep On Winning!

Stay Stealth In Your Relationships

When you’re going out with a girl, never speak to her about your conquests (women, work, or otherwise). Obviously stay charismatic and confident, but downplay your success. 

She will find out your fantastic attributes eventually, making you more desirable since you didn’t have to brag about them in the first place.

For women, guys don’t want to hear about your conquests either!  We don’t want to hear about how popular your are, or how many Facebook friends you have. 

We certainly don’t want to know that your ex-boyfriend was some hunky tycoon, well maybe. We just want to hear about you and your ambitions and dreams.

Related: How To Get A Rich Guy Or Husband

Stay Stealth As An Online Underdog

Let’s say you run a relatively popular blog that has over 100,000 page views a month. You will likely be inundated with e-mails and requests from people you don’t know, wanting you to pitch something on your site that you don’t care about or “guest post”. 

You’ve reserved the vast majority of your guest posts for friends in the community and you’ll get tired of politely declining random strangers.

By not revealing much about the statistics of your site, you’re able to spend time doing what you want to do and writing what you want to write. 

For people who really enjoy writing, this type of streamlining is what it’s all about.  The advertisers will have tools to figure out what your metrics are, so don’t worry about income if you have this type of traffic.

Related: Practice Stealth Action To Be Happier

Intelligence Underdog

If you are naturally witty, received straight A’s, and got a perfect SAT score, you are an anomaly. Given you are a rare breed, you will probably be more frustrated than average when people are slow to pick up things.  Your intelligence will rub the average person the wrong way if you aren’t careful, and people will start thinking you’re arrogant, where in reality, you’re just born smart and can’t help it.

The good thing about being more intelligent than average is that you can dial your intelligence down to the appropriate setting.  It’s harder to do the other way around.  Try and lower knowledge to equal the rest of your peers even though you know more. 

For example, if you are an investment professional with a CFA/MBA with 15 years experience and some young gun is preaching to you about investments, just nod and smile.  Of course if they are asking you for advice/help, feel free to help them out as much as possible.

Related: Are You Smart Enough To Act Dumb Enough To Get Ahead

Underdog Author

At the end of 2019, I decided to sign a traditional book deal with Portfolio Penguin Random House. As a first-time author, I appreciate them taking a chance on me because I was a big underdog.

More than two years later, my book, Buy This, Not That: How To Spend Your Way To Wealth And Freedom, will be published.

The chances are already slim my book will become mainstream and become a national bestseller. However, as a minority author, the odds are even more stacked against me. But I’m going to try anyway because if I succeed, it will feel like the greatest feeling ever.

Underdog author

You Are Secretly The “Overdog”

You may be stronger, smarter, faster, wealthier, better-looking than average, but your ego is kept in check and you don’t let anybody feel that you know you are in a superior position at the onset.  Eventually they will find out, as they always do.  However, in the meantime, you are busy doing your own thing and keeping humble.

The next time you feel like bragging about your great accomplishments think twice.  Make sure you include others in your successes so as to deflect out-right self promotion.  It’s often better to let your actions speak for you, or better yet, let others speak for you.  When the time is right, make sure you do ask for what you want if you feel you are not being recognized.

Be the “over dog”, but act like the underdog.  You’ll garner more success and feel more free if you do.

Readers, do you think there is an inverse relationship with self-confidence and how well you are doing vs. how often and loud you brag?  What are the times when it’s beneficial to toot your own horn?  What are some cultures, besides the Japanese culture, which encourages humility?  Is there a solution to getting ahead, without bragging if you start from nowhere?

Check out my Top Financial Products page to help you achieve financial independence sooner.

Photo: Sleepy Dog by Sam.

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Filed Under: Motivation

Author Bio: I started Financial Samurai in 2009 to help people achieve financial freedom sooner. Financial Samurai is now one of the largest independently run personal finance sites with about one million visitors a month.

I spent 13 years working at Goldman Sachs and Credit Suisse (RIP). In 1999, I earned my BA from William & Mary and in 2006, I received my MBA from UC Berkeley.

In 2012, I left banking after negotiating a severance package worth over five years of living expenses. Today, I enjoy being a stay-at-home dad to two young children, playing tennis, and writing.

Current Recommendations:

1) Check out Fundrise, my favorite real estate investing platform. I’ve personally invested $810,000 in private real estate to take advantage of lower valuations and higher rental yields in the Sunbelt. Roughly $160,000 of my annual passive income comes from real estate. And passive income is the key to being free. With mortgage rates down dramatically post the regional bank runs, real estate is now much more attractive.

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Comments

  1. Maty says

    November 5, 2015 at 9:25 pm

    Great post

    Reply
  2. Money Infant says

    February 10, 2012 at 7:47 pm

    I’ve learned over time that often the best course of action is to “fly under the radar”. Not only do you save yourself the hassles that sometimes (usually?) come with being in the limelight, but you can also learn things that might not otherwise be shared with you. People tend to ignore those they perceive as average or non-nondescript and often speak more freely around these people.

    Reply
  3. Van Beek @ Stock Trend Investing says

    January 29, 2012 at 6:03 am

    Very little here to disagree with. In the Netherlands, we have two proverbs that reflect a similar warning as the one you started with. I’ll try to give an appropriate translation here:
    “High trees catch much wind” & “He who raises his head above the mow-line, can expect to lose it”

    Reply
  4. MIGHTY says

    January 27, 2012 at 8:09 am

    I’m not surprised at how many people agree with this post, but I definitely do not.

    That’s not true. I mostly do. But then again, I don’t. Umm …

    What you are basically saying here is that humility and knowing one’s “rank” is essential. This is brilliant and age old wisdom passed down from the cavemen. Humility recognizes a couple of key universal truths that will likely never change. Namely (1) there’s always someone better and (2) there is always a component of luck to everyone’s success story. Boasting about oneself is silly and asking for comeuppance. Just around the corner there is someone waiting to best you and take you down a notch. Additionally, though luck favors the prepared, it is still luck. You can’t take credit for everything and acknowledging the X factor that increased your success is only facing reality. Even the most arrogant person in the world has to admit the truth of these facts. Self-deluded is another story …

    Now then, beyond that, me gotz some major problems here.
    (1) Bright lights illuminate the world: There is power in allowing your success to show. This doesn’t mean being an @$$ or putting others down to build yourself up. But success begets success and people are uplifted by seeing others achieve. Any who do not are not worth worrying about. People who would resent you for not picking up the check are also not worth worrying about.
    (2) Worrying about the egos of others shows disrespect and disregard: It is not your job to “protect” the insecurities of others. To act differently because you’re worried about how others will react is disingenuous and not authentic. Again, this doesn’t mean being an @$$ or at all unkind. However, if “Friend A” is sensitive about money, you do him/her no favors by underplaying your own financial success. If “Friend B” has relationship issues, pretending your marriage isn’t as strong as it is helps not at all. You show yourself to have no respect for the abilities of others to manage their own feelings or situation. Playing yourself down to prevent someone from feeling less is not being the underdog, it’s silent arrogance.
    (3) False advertising for the win is shady: If I play down my skills in a fight, I may win, but it’s not the way I want to win. I want my opponent to know the full range and power of my skills and abilities. I want the best opponent possible who has not been deceived about what I’m bringing to the table. I don’t want a victory by way of ambush or subterfuge.
    (4) Concerning oneself with not being the “tallest blade of grass” to avoid being the “first to get cut” is cowardly: That is all.

    Being humble is essential. Downplaying one’s abilities and success is dishonest.

    Thanks for the article!

    Reply
  5. FG says

    January 23, 2012 at 7:24 pm

    Loved this post, Sam! I agree with this philosophy and I also believe in humbleness and leading through action. These are the types of leaders that can attract people to their cause. Bragging on the other hand just turns people off and makes them want to fight against you. Why cause trouble for nothing? You can have more mutually beneficial relationships if you work with people and bring them up along with yourself.

    Reply
  6. Jeff Crews says

    January 22, 2012 at 10:41 pm

    Agree with not being “That guy”. I kind of compare it to coming in as a freshmen and playing college soccer. There are some thing I regret (I was a hot head and very cocky for a freshmen). I stood out from the start, and it didn’t help me excel. I learned quickly and by my senior year I tried my best to keep the light on the other players. All I had to do was my job, and everyone recognized that with future awards, etc.

    I graduated and started my career. I was able to excel and truly learn due to 1. always trying to learn and 2. working my butt off. Luckily I learned from my college soccer career and am now truly enjoying my real not “that guy” career.

    Reply
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