Always Be The Underdog To Get Ahead

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. With their fancy degrees, they are saddled with debt and end up doing what everybody else does who didn't go to a fancy college.

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. At the end of the day, 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?

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Photo: Sleepy Dog by Sam.

61 thoughts on “Always Be The Underdog To Get Ahead”

  1. Money Infant

    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.

  2. 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”

  3. 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!

  4. 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.

  5. 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.

  6. Good rules to live by, Sam. I have a high position in the company in terms of controlling spend. But I prefer the Japanese style of staying behind my team members. Let them seem to make the decisions, and underplay my own hand. I’ve frequently helped with their work, and let them take credit for it. Increasing their skills, status and reputation indirectly builds my own as leader of a good team.

  7. What if you actually are the underdog, and you know it. I find it humorous to brag about that in my case, or when somebody else brags about theirs. It’s kind of like reverse humility. Respect can be gained if you find and show humor in your imperfection, weakness, misfortune or plain stupidity.

  8. Marissa @ Thirty Six Months

    The one thing I have learned over the last 8 years is that even when I think I know everything, I don’t. That old proverb “Its better to look like stupid, then to open your mouth and prove everyone right” is my motto in new positions. I like to get the lay of the land and earn my strips before I start anyone how to do their job, even if I am their boss.

  9. Great post, Sam. It makes you think about how important it is to fly under the radar and focus on the important things rather than skin deep appearances such as wealth and flashy consumer purchases.

    1. Thanks. It really is a similar concept to consumerism and the millionaire next door. They aren’t by a long shot the flashy benzo driving folks who are the real wealthy.

  10. After College Money

    I really like this info, it seems like a covert strategy to success. I was never one to brag in my life so I can relate to this advice.

    However, I do feel that you need to flaunt your strengths in certain situations, such as when someone is challenging or qualifying you. If someone doubts your skill, you should prove them wrong if the situation is valuable to you. If you never WOW anyone, they could write you off as a nobody and may take advantage of you.

  11. This actually makes a lot of sense. I’ve seen so many people acting like they are (whether or not they actually are) better, smarter, wealthier etc. than everybody else, and nobody seems to like them very much. Thankfully, I have really crappy self-esteem so I’ll always be the underdog, I never toot my own horn. Well, unless I’m having a fabulous hair day, but that’s it. :-)

  12. I think that you’ve got some pretty good ideas in here sam, to a point. Of course, it’s always better to downplay your skills and abilities in sports and things of that nature – or “under promise and over deliver” so that you can look like you went above and beyond (or in the sports case, snicker to yourself about whomping on someone unsuspecting who had been bragging all day/week/month about how awesome they are and then fall to someone who doesnt even play up their own talents in the least.
    I think that keeping it low key can eventually become slightly damaging though – if you keep it too low key, people will think that you’re not friendly and dont want to work with them and possibly dont do much while you’re at work. You always want to make sure that you’re approachable and will at least vouch for your accomplishments when necessary. Your boss may not remember, and it could cost you a promotion or raise.

    Also, this could get this comment flagged as spam, but I figure you’d like this essay: – it relates to this topic

    1. The post is not about race, but there is cultural aspects of keeping humble and low key at work.

      There’s a reason why Americans have a stereotype of being loud, big, and obnoxious. It’s probably because we are!

      Perhaps one needs to skillfully toot without anybody knowing. Like wearing make up that people can’t tell for women.

  13. I usually don’t brag. It is just not me. But if something extraodinary happens and I am excited as hell, yes, I would want to share my news with others. But since extraodinary things happen very seldomly, so most of the time I am an underdog.
    I like underdogs in life and in sports. I am always cheering for them. Hits close to home, I guess.

  14. People who show-off online annoy me the most. Look at me, look at how much I make, look at my great life. Give me a break.

  15. I also agree with keeping it low key. To be honest, for me it is not even a fake either. Yes I know I am good at some things and have things to offer, but I still have a lot to learn and I need other people sometimes. I am not successful as one but as a whole with others in my life. To me this is what it is all about. Finding your success while working with others on theirs too. No man is an island.

  16. Totally agree. Especially where I live there is a high percentage of wealthy people. The ones who are the wealthiest are those that wear torn shorts and old t-shirts that were free after they volunteered or ran a race. The ones that don’t have a ton of money carry Louis Vuitton handbags.


    “…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.”

    I certainly can get on board with this post. The only one I can’t fully agree on is wealth. I don’t disagree – don’t flaunt it. The idea of never, ever talking about it to me is fairly old school. I’ve had many great conversations regarding wealth with some of my closest friends. And I certainly wouldn’t be having lunch with people that resent the idea of earnings.

    As always, a joy to read.

  18. I like it. I feel like I’ve been talking about my blog a lot with my real life friends. It’s just exciting and totally but I do think I need to stop talking about it. No one cares what my Alexa ranking is (except for me)!!

  19. I certainly wouldn’t resent my friends if they didn’t treat me out or pay for my dinner and they made much more than me.

    That wouldn’t be a good friend :) Though this does add to the stigma of not talking about money, now doesn’t it?

    1. I think you would after you discover they make 5x more than you, and you always have to pick up the tab when you go out!

      But if not, then you are Zen, and should no longer be mad at your boyfriend for you being the sugar mama in your old article!

      1. Oh lol you mean my ex boyfriend? Well that’s true.. but I felt he was using me (he had the audacity to ask me to buy him things).

        Besides, friends and boyfriends/girlfriends/husbands/wives are different, IMO.

  20. That’s a really cool proverb you opened with and I like your quote “Be the ‘overdog’, but act like the underdog.” I don’t consider myself to have a big ego, it’s just not my style to brag. I make sure my manager knows how much I’m contributing but I like to stay below the radar. I agree with your point on not sharing how much money you have with friends. People can get really awkward with money and that’s not something I want to worry about with my friends.

    1. Yeah, I guess I’m old school that way. Since I believe friends should always be trying to take care of the other anyway, what does one’s income matter? It’s an honor to treat a friend.

  21. Darwin's Money

    Great topic. I tend to agree on most fronts. One spot where fairness and ethics doesn’t necessarily win out though is the workplace. I’ve seen some GREAT, great hard workers that just get overlooked and ignored because they don’t get enough “visibility”. They don’t toot their own horn enough, rub elbows with the top brass, get in on those special projects where they get to present to the execs. I know, it makes you want to vomit in your mouth when you see weasels sucking up just to get ahead, but that’s often how they get ahead. Stinks, but sometimes by overselling themselves, they are doing themselves a favor while the humble doer gets overlooked.

    … and in my experience, every person who has ever gone to MIT lets you know it. They try to “sprinkle” it into a conversation here and there and I’ll here them do it like 5 times after I meet them in other meetings, over lunch, with clients or whatever. It’s like they can’t say it enough, “know me! I’m soooo smart! I went to MIT!” (meanwhile I’m the same level or higher at your age, make the same or more money and I went to a measly state school for 1/4 the price LOL).

    1. It is funny that you mention the insecure MIT grad.

      They are more a dime a dozen here in Silicon Valley, but they will still certainly remind you. When they do, you just have to put them back in their place!

      Yes, speak up when you’ve done something great at work and don’t feel anybody notices for sure!

  22. Squirrelers

    Smart thinking to steer that presentation into a conversation rather than a critical directive. That’s a tough position you were being put in! Good example of why it’s important to think strategically, recognize that perceptions matter, and keep your head in the game at all times.

  23. You have some excellent tips in this. I have always had an aversion for people who “toot their own” horn. But sometimes I think I go to the other extreme, not seeking credit and then seeing others “own” ideas I first put forward. There is a fine line to walk between humility and pride. I don’t always walk it well.

  24. I think the word “humble” you mentioned at the end is what intelligent people should strive for because, you’re right, eventually people will realize you are smarter or more helpful or more witty than you let on. No one likes a braggart.

  25. I’m definitely an underdog by nature. I keep a low profile and feel uncomfortable bragging about anything. This works well for me in general, but I can’t transition to ‘overdog’ at all. I don’t have the A type personality and I think corporations reward that behavior. That’s why I think I should be working for myself. :)

    1. It’s about being the SECRET overdog! You know you’re in a better position, but you don’t let it on to be that way.

      I think you’d be great working for yourself Joe.

  26. Wow, that is a lot to think about! I am naturally understated and never brag about myself. There are times, I think a little too much so. In my former role (CFO), no one liked the message even when it was good news. The reason was everyone took credit for it. You know, we made the numbers because of sales or marketing vs. the juggling act the financial people had to do to make it happen. Learning how to work with other people is a huge trick. I remember hearing that more people are fired for their soft skills or lack of versus competency.

    1. Yep, team work is massive….. it’s what grad school emphasizes ad naseum. So true though, b/c if you can’t stand working with someone else, things blow up and you get screwed.

  27. Excellent post! I am reminded of “it’s the empty can that rattles the most”- If what you do or have to say is truly that good, others will notice. If you have to shout about yourself, you probably aren’t so good and/or you have inferiority issues of some kind.

    I strive for personal improvement in what I do; in all aspects of my life. Whethe it is personal or professional. I set my sites on the ideal. I realize the ideal is not attainable, but it prevents slacking.

    I figure acknowledge my wrongs and my rights, but there is no reason to shout about them. Allow the river to keep moving.

    1. Great quote! I’ll have to use that at some point as well. Perhaps the empty can that has the tab in it, and that’s it. It does rattle the most since a full can doesn’t have space to do so.

  28. Eric J. Nisall - DollarVersity

    I kind of go by those principals, especially when it comes to my online presence. I don’t announce to the world each time I reach a personal milestone, or when I get a mention here or there, or when I get paid. I just go about what I do in a manner I am comfortable with.

    I think the ones who talk the loudest are the ones who actually have the most to prove. If you really have to scream above the crowd to be heard, are your words really that important?

    And, if you are always trying to show off, you really won’t accomplish much besides turning people off anyway.

  29. Not necessarily on the PF blog. There are plenty of PF blogs out there who are not cashed up, and discuss eradicating debt and so forth.

    Showing vs. telling is a great tip for writers too. Better imagery and more impactful.

  30. I’m really onboard with your “keep a low profile” perspective. It’s better to let others toot your horn than you doing it yourself.

    However, now that I have two teenage boys, I always try to make positive comments about their accomplishments, so that they realize that they really have accomplished some remarkable things, thus far, in their short lives. I think that they sometimes tend to keep too low a profile.

  31. I absolutely agree – if you reveal too much of your success, then everyone starts asking for favors. Yet, online it seems that revealing your success makes more people come to you and in the end, your site continues to grow. It seems to be a difficult balance because your name (or fame) can help your online business grow just as fast. Yet, too much public knowledge can lead to serious competition.

    1. It is a balance indeed. One definitely has to do a minimum amount of self-promotion online to get noticed.

      It’s when it starts getting louder and overly repetitive where I switch off, and things backfire imo.

  32. I agree with lots of this. I think especially with a new job, you ARE the underdog. Your colleagues know so much more than you, because you are new. People in different companies do things differently, and by trying to prove yourself too early out of the gate, you could damage yourself instead.

  33. I rarely, if ever, “toot my own horn”. I’m generally pretty laid back and relatively quiet at work. However, I work my tail off and get things accomplished. I do speak up on occassion and when I do it is with pretty strong opinions sometimes. It is amazing how much more well received your input and opinions are when you do this. I don’t speak up for “effect”, I do it because I have something important to share.

    I’ve done pretty well for myself at this company, and I haven’t had to have flair or be bombastic to do it. I’ve earned a strong level of trust with senior management with my approach. To the point, where I am sometimes invited to offer input at senior level meetings.

    There’s alot to laying low. Great post.

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