How To Make People Happy All Of The Time

Bowing In Respect

Are you wondering how to make people happy all of the time? I'm not sure that's a wise endeavor, but let's see if we can try.

When I was ruminating on whether or not to go back to work after two years of absolute freedom, my friends all thought I was crazy.

“What if your boss is a micromanager who makes your life a living hell?” questioned an ex-coworker.

“What's the point of saving and sacrificing for so long if you're just going to jump right back in the fire?” wondered an online buddy.

I told them I was getting bored. As a professional writer, every experience, good or bad, has the potential to be a treasure trove of good material. Writing is so much easier when you're emotionally charged up.

I've had a compliance woman throw me under the bus during a group meeting and a guy promise me one thing and do something totally different. It's been awesome! I truly love the pain because pain makes everything else feel so much more pleasurable.

When you have a lot of freedom, you start taking your freedom for granted. Going back to work to be a “yes man” is a great way of keeping the appreciation of freedom alive. This post offers a simple way to make people happy all the time. If you're someone who fears getting laid off, this one is also for you. 

How To Make People Happy: YES SIR! YES MA'AM!

Writing is a very individualistic endeavor. Ask five writers to write about a narrow subject like “how to tie your shoes” and you're likely to get five very different results. One of the keys to being a good editor is to not inhibit the writer's creativity, while offering constructive suggestions.

After one year of creative freedom as a consultant with a certain company, the graphics department gave me a ridiculous 8-point guideline on what pictures to use with my posts. It had already been hard enough to choose pictures in a 2:1 aspect ratio (really wide and short) vs. the normal 3:2 aspect ratio format. Now they were adding additional hoops to jump through in order to pass quality control.

After the two pictures I selected for a post were rejected, I was frustrated. These were my choices that in my opinion matched with what I had written. Who knows better than the writer himself what matches and what doesn't?

It was as if the tail was wagging the dog where the picture was more important than the actual content. If I managed an art or photography blog, the images would be most important. But I was managing a site where written content is King.

Just Take Orders Well

Instead of complaining, I came up with a solution. Have the creators of the 8-page picture guideline create a repository from which any picture may be chosen. In this way, writers would no longer waste time finding the perfect picture, only to have it rejected by the picture police. Brilliant!

I could have objected to their objections about my picture selection because it suppressed my creativity and dampened my motivation. Instead, I said, “Happy to accommodate.”  What I did was a little jujitsu. To make them happy, I put the onus back on them.

But guess what happened to this amazing suggestion? They never created the picture repository. As a result, they could no longer nitpick about the pictures we selected. Months later, the creator of the picture bible quit. Classic.

Lesson #1: Always accommodate a request no matter how dumb. Even if the person has no experience with what she is asking you to do, just tell her “yes ma'am.” When it becomes apparent what she is asking is unreasonable, simply ask her to provide you examples of her work to mimic.

If she is a fraud, then she won't be able to come up with anything, and will therefore leave you alone. Your goal is to smoke out people who only tell people what to do, but don't know how to do it themselves.

How To Create More Happiness

When you are an employee, you are expendable. Always remember this. You can be thrown to the streets with the next bin of shredded documents at any time. An employee must know his or her place. The more you need the money, the more you must be respectful to everyone.

As a masochist who likes money, I find working for a company as a consultant to be extremely exhilarating. While it's great to be the boss of my online media company, there's something magical about being relieved of responsibility and just doing what you're told to do.

Some People Have No Experience

During my tenure at another company where I was in charge of managing and writing content, I was told a new full-time person was to assume the Head of Content role. As a consultant, I didn't care too much and was looking forward to working with this new hire in order to learn new writing and content marketing techniques.

It turned out the new hire had practically zero experience writing any content! I couldn't find one single publication of his on the web. He didn't even have his own website. Further, he had no idea about online content marketing because that wasn't part of his role at his previous firm.

As a creative, I tried my best to say “yes sir,” but I couldn't hide my lack of respect for someone in charge of content who had never written content. It would be one thing if he had been the editor at an online media company like Business Insider or The Wall Street Journal, but he wasn't.

Because I could no longer fake my enthusiasm by quiet quitting, I offered to resign. And that's when things got interesting. The Head of Content person started to panic.

We had emergency meetings with the CMO and CEO about how we could better work together. But I wanted none of it because I knew my value to the company as its content creator, editor, and manager of a team of writers. If management hired this person for big bucks above me, then they should try to get their money's worth from him.

Money Gives You Options

When you are financially independent, you have no problem voting with your feet by leaving. At any rate, we worked something out, so I stayed on for a little bit longer. Two months after joining, the new Head of Content was fired. Finally, management saw through the smoke screen. 

Lesson #2: Know your worth and don't be afraid to move on if you feel under-appreciated. Management will realize who are the producers and who are the dead weight. You will make your bosses happy by making them realize your value.


The key to making everyone happy is to do as you're told. Whether that person has the relevant experience to tell you what to do is besides the point. This is where so many people get in trouble because they don't respect authority. Even if you are older and have more experience, suck it up if you need the money!

The goal of this post is to make other people happy, not you. After a while, always doing what you are told will probably make you pissed off and miserable. But because you make other people happy, other people will start liking you. When other people start liking you, you will get paid and promoted and eventually get to come out of your shell and play.

My biggest weakness as an ex-employee is not being able to fake my feelings well enough to create a massive support network. If I did, I would have probably made Managing Director at my old firm by age 35. If I don't believe in something, I will butt heads. This is a career limiting move.

If you just can't stand bowing to other people's demands you don't respect, then your only two choices are to negotiate a severance and find another job or be your own boss. Staying at a job with people who don't inspire you will suck your soul dry.

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Related post: Solving The Happiness Conundrum

About The Author

70 thoughts on “How To Make People Happy All Of The Time”

  1. It’s amazing to think of what people will do for the money. Idk if anyone like Triumph the Insult Dog from Conan over here but he recently did a special where he asked Democrats to say what policies were important to them. Then he offered them $50 to read a card complimenting Goldman Sachs. All of them chose the $50

  2. I can definitely relate to the idea that having to deal with crap in your full time job leads to blog material (my own blog is essentially built on that premise), but I’m not quite as masochistic as you. Once I achieve financial freedom, full time work can kiss my you-know-what.

    Making everybody happy is taxing, impossible, and all in all just not worth even attempting. In customer service, every person wants something different, and they all want something directly opposed to what your employer wants. Even businesses themselves don’t understand it, bending over backwards to avoid having a single unhappy customer rather than following the Tim Ferriss 80/20 rule. You can’t make everybody happy. Just do what you can to get ahead and move on.

    ARB–Angry Retail Banker

  3. SavvyFinancialLatina

    I just started a new job with a new company. At my previous company, I committed a couple of mistakes at the beginning, establishing myself as outspoken. It wasn’t horrible because through my tenure there I was well liked by most of my stakeholders. I was a great individual contributor and people liked my work. But I know that it was a detriment if I wanted to move up. I was lucky to have great managers who didn’t care…Too busy with fighting other battles. It was more get the work done attitude. In my new role, I’m making an effort to be more of a “yes of course you are right” person. It sucks, but you get used to it. Hopefully, it will lead to promotions. I will let you know in a couple of years if it works out. At this point, work is $, and $ is a path towards FI.

  4. CPA Housewife

    “I truly love the pain because pain makes everything else feel so much more pleasurable.”

    I’ve always believed this with regard to physical labor (which is why my kids will always be my lawn care company), but I’ve never been able to embrace it while being thrown under the bus by a coworker. That stuff lingers with me for way too long.

    I’ll try to focus on that the next time things/people run amok.

  5. God, I have to print this article and give it to every new hire at our work. I hate to sound like a cliché, but I am encountering more and more of entitled attitude amongst the new hires from younger generation. We have brought on a new guy , 25 y.o only a year out of school, as contractor on board to see if we like him for a permanent position. You would think someone in this situation will want to try to impress his employer!!
    We had to teach him to call into work and let us know if he is running late, and once when I told him what our expectations are from him on a daily basis ( basically from every employee). He just said : Well do you factor in my thoroughness? Because I have noticed most of you guys are not as thorough as I am, that’s why I take longer than you guys to perform the tasks !!
    One other thing that I am noticing is that most of these kids really didn’t have a real job growing up ( remember flipping Burgers, or working at Macy’s).
    As you said : Employees are Expandable not Special!!! I suppose some people will learn it the hard way.
    And yeah not wanting to babysit younger employees and fill the gaps left by their own parents in their upbringings is another motivation for FI and saying F-U and walking away when things get unbearable..

  6. Good stuff! I would not last long in that kind of environment. I doubt I can ever go back to work for a company now. Any BS is too much BS! Well, maybe if they pay me a serious amount of money. Even then, I don’t think I can put up with it long.

  7. Well! At this stage of my life, working for people, I really don’t care about making anyone happy in that organisation. And I never will. I would be more inclined to make them unhappy. I guess I’m not smart enough to play dumb to get ahead because I don’t want to. I am not interested in moving forward with the company. Playing dumb would hurt too much though.

  8. Ten Factorial Rocks

    Well written post, Sam. In the age of individual narcissism, it is good to see you say what it takes to build a successful corporate career. Of course, you may have a boss dumber than you and co-workers could be dumb, egoistic or manipulative – or worse, all of the above! None of this should alter your fundamental reason of why you are working. The hype on entrepreneurship, which I expose in my article, has unfortunately created more silent victims in its wake than what a straightforward employment career can provide. But no, the powerful but wrong narrative of ‘cubicle prison’ has corrupted the mindset of many young people and they fall into survivorship bias about FIRE which, without their realizing, actually makes their FIRE dream that much more distant!

  9. Finance Solver

    Your writing style never fails to disappoint, Sam. I’ve never heard of “voting with your feet by leaving” ever before. Great analogy.

    I can’t believe the Head of Content was hired when he didn’t produce any content before. It makes me wonder how he got the job in the first place, maybe he’s just a really great talker / interviewer but in the long run, everything becomes visible. Wonder what the company was thinking when they decided to hire him.

  10. Lenny Nurdbol

    Huh? What?
    “How To Become A Professional Ass-Kisser” ISN’T one of my dream professions!

    If you want to make people Happy there are better, more productive means…like trying to stir up some Trouble in a mind-prison company so the employees open their minds and THINK on their own…

  11. Hi Sam,

    As a boss most of the times I just want people to do as their told. Sometimes, employees will disagree with me and want to argue their point of view. What they don’t realize is yes they are right some of the times, but if I did it differently than I’m gonna hurt “Suzy’s” feelings. Suzy in turn is going complain to her boyfriend “Johnny” at the loading dock. Johnny in turn is going take a longer lunch and miss the shipment. Because we missed the shipment I’m going to spend the next few days traveling to the customers site and assuring him his shipments will be on time next time. Because I had to travel I missed my kids soccer game. In turn my wife gets mad at me and I end up sleeping on the couch.

    Please do what your told so I don’t have to sleep on the couch.

    Thanks, Bill

  12. Not being able to fake feelings long enough is an incredible career liability. I’ve found that when I “Yes ma’am, yes sir,” long enough, I can usually find value in everyone, including people that I thought were mouth breathers.

  13. Oh my gosh, this post brought back some awful memories of my last job. Everyone there was great EXCEPT for my immediate supervisor. She was irrational, and not very intelligent, and childish. I couldn’t stand working for her. But I still did the “yes ma’am” thing and then went home and screamed into a pillow. She was really, really awful.

    The good news is that she made me so angry that I decided to consider going to law school. I was really burnt out in school by then and didn’t want to go back, but she provided a new motivation. I nailed the LSAT and that was my signal that it was time to move on.

    I’m soooooo much happier now as a lawyer at my current firm.

  14. I’m in the same boat. I’ve been a Content Strategist/Writer for 15 years for Fortune 500 e-commerce companies. I’m financially independent so stopped working 2 years ago. And I’m getting bored. I tried volunteering for non-profits I feel passionate about but the work available didn’t satisfy me emotionally. For example, there’s a huge need in the charity world for phone banking, outreach, grant writing, fundraising, etc. I’ve tried all those things.

    Here’s what I miss from corporate life: the excitement of being on a team and launching a product, the camaraderie, working with super smart and talented people, and good company benefits. What’s holding me back from joining a company again? Unlike you, I don’t like to write. I just did it for 15 years because I’m good at it and it pays $$ at big Internet companies. Plus I don’t have the tech savvy that’s required these days.

    Not sure what I’m going to do to get out of this boredom funk. But a person could have worse problems, eh?

    Anyway, I’ve been reading FS for a couple of years and want to tell you that you’re my favorite blogger.

  15. Graham @ Reverse The Crush

    Really enjoyed the read!
    I feel like all the complainers out there need to hear this. It just makes me think of those people that complain that they’re not getting a promotion, or are unhappy with their job, but do nothing about it.

    To answer your questions, I think doing what you’re told is definitely a good way to get people to like you. Especially if you do it with a good attitude and don’t put up any debate about it.

    I like to think I’m more of a non-conformist and usually do the opposite of others. And I definitely am willing to sacrifice ego because I’m focussed on doing whatever it takes to reach the long term goals.

    As for that situation with a boss, I generally try to avoid any confrontation to make the managers role easier, but there are ways to respectfully suggest something. If it was an important enough matter, I would attempt to provide my opinion in as delicate a way as possible.

  16. I really do enjoy being employed as a doctor. I’m just told where to be and at what times, and I take care of the rest. Unless I do something ethically wrong or clearly against the companies best interest, I will be left alone. This keeps my work challenging and relatively low stress at the same time.

    But I also have a couple of side hustles which give me full autonomy over what I do. It’s the quality and quantity of my work that will determine how much I make. This also has its advantages. I love being able to find ways to scale up my side income by working more or more efficiently.

    1. Doctor plus side hustler? Great combo! I agree. It’s nice to be told what to do + have full autonomy over your own creative activities.

      For example, wouldn’t it be fun to get managed by a 25 yo who has little experience, lots of debt, and a small salary? We’ve all been there before, and it’s fun to relieve those years through someone else. Get a beer at his place where he’s renting a room and then hitting a local dive bar after. So fun!

  17. I’ve gone through both sides of – taking it and liking it, and putting up a fight when I disagreed. As more time went on, I stopped putting up a fight because it tended to just make things worse for me and I’d get too stressed out. Even if my boss couldn’t understand that his way was inefficient and suboptimal at times, arguing became too frustrating and took too much energy.

    I was probably one of the most vocal in voicing my opinion amongst my colleagues when our boss seemed out of it, and I think that was largely because I used to care SO much about my job. I wanted to us to do things the BEST way all the time. Towards the end of my time there, I cared less and less about my job and just went with the flow. It sure made things easier.

    If things were going to go down the drain, it didn’t matter to me anymore because I planned to leave. I also began to realize that a lot of the times my boss was stuck between a rock and a hard place in his suggestions because his hands were tied from above. So, trying to argue against him was also trying to argue against the clueless “gods” above who ruled everything – total waste of time and energy.

    1. I am going through this myself currently as you describe it. Interestingly enough with some cases (micromanaging) it almost doesn’t get easier for us when we give in, because they just micromanage more! How painful.

      I totally agree with not worrying about the place or product going “down the drain.” Once you have made your suggestions and they are ignored, a clear indicator is being given to you on how to handle the situation.

    2. +10 comment!

      It is ironic that the more you care, the more you want to speak out to do the best thing. But the unfortunate reality is that the more you care, the more you should let your bosses and the “Gods above” make all the decisions and stay agreeable, even if you think they are making the wrong decisions.

      Jujitsu requires you to support your bosses in victory and in failure, b/c they are human too. When you are seen as a loyal soldier, you will more easily ascend. Bosses want to see their employees as extensions of themselves and as advocates.

  18. Fiscally Free

    This post hits home for me. When I started a new job a year and a half ago, I told myself I wouldn’t make waves, so I have happily agreed to do whatever I’ve been asked, no matter how ridiculous it is. It does seem to make people happy, but just like Sam said, it is making me “pissed off and miserable.”

    I would be willing to put up with this if it looked like there was some big upside potential, but I work for an Asian company, where the only thing that really matters is seniority, so if I want to advance in the company, it will be a long slog.
    That’s not going to work for me, so I’m planning my early retirement and can’t wait until I can waltz out the door.

    1. If it’s any consolation. I’ve worked for Japanese, German, and American companies in SF area. The office politics and bureaucracy is same everywhere. If you want to have a shot at moving up, you need to learn to please the game and praise the senior people unfortunately. Even then, the upside potential of windfall is fairly low with mid to large companies.

      The only companies with a realistic huge upside potential are smaller rocket ship companies at its early growth stages ala Facebook, Google, Amazon, Microsoft during their earlier days.

    2. Sounds painful. But seniority based off age and time at a firm really is commonplace, regardless of ability. And the older you get, the more you will expect the same type of respect, regardless of ability.

      Work on that side hustle on the DL!

  19. On reading this, I am reminded of the “Parable of the Ups and Downs” by Bob Terry. Enjoy!

    “What makes an Up an Up and a Down a Down is that an Up can do more to a Down than a Down can do to an Up. That’s what keeps an Up up and a Down down. The Ups tend to talk to each other and study the Downs, asking the Downs about what’s up—or what’s coming down, for that matter. The Downs spend a lot of time taking the Ups out to lunch or to dinner to explain their Downness. The Ups listen attentively, often in amazement, about the experiences of being down. They contrast one Down’s experience with another Down’s experience and don’t worry too much about what the Downs are up to because the Downs never get together. If they did, the Ups would have to shape up. After a while, the Downs weary of talking to the Ups. They tire of explaining and justifying their Downness. They think, “If I have to explain my Downness one more time, I’ll throw up.” And so they form a process which they call “networking and support groups.” This act makes the Ups nervous. Three Ups together is a board meeting; three Downs, pre-revolutionary activity. Some Ups hire Downs, dress them up, and send them down to see what the Downs are up to. We sometimes call this “personnel and affirmative action.” This creates a serious problem for the Down who is dressed up with no sure place to go. That Down doesn’t know whether he or she is up or down. That’s why Downs in the middle often burn out. Sometimes what the Ups do to smarten up is to ask the Downs to come in to a program one at a time to explain their Downness. The Ups call this “human relations training.” Of course, the Ups never have to explain their Upness; that’s why they’re Ups rather than Downs. There’s good news and bad news in this parable. The good news is, we’re all both Ups and Downs. There’s no such thing as a perfect Up or a perfect Down. The bad news is that when we’re up it often makes us stupid. We call that “dumb-upness.” It’s not because Ups are not smart. It’s that Ups don’t have to pay attention to Downs the way Downs have to pay attention to Ups. Downs always have to figure out what Ups are up to. The only time Ups worry about Downs is when Downs get uppity, at which time they’re put down by the Ups. The Ups’ perception is that Downs are overly sensitive; they have an attitude problem. It is never understood that Ups are overly sensitive and have an attitude problem. I used to think that when Downs became Ups they would carry over their insight from their Downess to their Upness. Not so: smart down—dumb up.”

    His take on it all is nicely summarized as follows and speaks to leadership, togetherness and being careful about boundaries, in the workplace or otherwise:

    “Are we grasped by the injustice of the issues that need to be addressed? Are we in dialogue in up-down relationships so that we do not have blind spots? Are we in motion to address issues in collaboration with others? Our goal is to get rid of arbitrary up-down power relationships. We should not have up-down relationships based on color, gender or anything else that is arbitrary and capricious or has to do with how we’re born. Rather, we need to find ways to stand side-by-side, so that as we look out at the world together, we can eliminate any of the barriers that keep us from building an authentic, vibrant, human community.”

  20. Jack Catchem

    “When you are an employee, you are expendable.” Oh so true. As a cop and Marine, so many of my peers get an inflated ego and forget this. One wrong move and you can be gone.

    Always doing what you are told is a great way to go (especially if you have plans on heading to the top)! The only downside is when you run into situations where “what you are told” is illegal or unsafe. A perfect example: being ordered to take flash photography of a weapons cache you are recovering in the middle of the night a few meters from where the bad guys are sleeping.

    Outside of those two caveats, I’m a pretty big sell out. Rule #1: Do as Daddy Does. Rule #2: Always know who Daddy is. Between these rules my employment has always been pretty simple. Without financial independence (yet) I know exactly who signs my paycheck.

    I already surrendered my ego two years ago. I left behind my seniority in a larger organization to be the new guy at a much smaller operation in exchange for a better paycheck and lifestyle.

    And in answer to your question, if the boss won’t be swayed by any other means, you are left with judo and Jedi mind tricks to gently persuade. Otherwise sometimes you have to take the loss. You don’t play chess without losing some pieces. The goal is to lose strategically.

    1. “Rule #1: Do as Daddy Does. Rule #2: Always know who Daddy is”

      WONDERFUL! So smart. You should write a post about this.

      I love the judo moves.. you can do that on friends and significant others as well :) Make them believe it’s what they want, and make them takes steps for you to help them help you help them. YES!

      1. Jack Catchem

        Thanks for the inspiration, Sam! I crafted a post for my audience based on this and it was very well received!

  21. Simple Money Man (SMM)

    Hi Sam,

    I agree it can be an internal struggle to agree with someone whom you know doesn’t have the same level of experience you do…and oh yeah is wrong :-).

    I’ve found in my work experience so far that it’s good to talk less and listen more to bosses. Sometimes when they do solicit your feedback, I’ve found that it comes off a little bit more gentle when it is in the form of a question (e.g. – how about if we first check with our current supplier to see what they think may be the reason for late deliveries recently rather than researching new ones?) This way, you can get your bosses approval too and ask instead of just state your opinion.

  22. Even getting myself on my journey to financial freedom has changed my relationship to my job. in my full-time work, I am a temporary employee hired to do one task. There is absolutely no chance for promotion. Knowing this, I do precisely what I am paid for and nothing more. When they try to add new tasks, I ask for more pay. When they add new constraints, I say no thank you. I am okay with knowing I’m replaceable, especially because I know that they are far easier for me to replace than I am for them to replace. I have institutional knowledge and they would need to train up any replacement. Knowing this, I am far less subservient than the other temps who haven’t made a switch in their mind. They feel reliant on this job.

    1. It’s great that you are pushing back to ask for more compensation if they ask you to do more work. Totally logical, especially if you are a temp employee.

      If you really love the job and want to move up though, subservience is a requirement.

  23. This seems like a pretty straightforward way to make your superior happy. IMO, each person has to draw a line in the sand and choose a limit to this kind of “yes sir” behavior.

    For example, I once had a boss who loved to butt heads with me; everyone told me that they felt he was threatened by me and was trying to intimidate me as a result. As part of his intimidation tactics, I was asked to take action in a few unethical ways. I wasn’t left with much recourse, unfortunately, and to be honest, I didn’t really care much about making the guy happy – I just had to get out as fast possible. Maybe if I had gone along with his puzzling demands I would still be in this role. But I would also be miserable myself.

    1. True. It’s up to you on how much lip-biting you must endure to get to what you want. The higher you go, the more political it gets. I have a real problem w/ conformity when I don’t respect someone. At the same time, I’m supportive and loyal to death to people I truly admire.

  24. The Green Swan

    Doing what your told at work is usually a good thing… but there are certainly times when leaders want others to think for themselves and make decisions (within reason). At the same time you’re most likely not going to have people telling you what to do constantly. You need to take initiative and come up with new ideas, new projects, etc. It’s hard to say a blanket statement that “always doing what you’re told” is going to keep people happy at all times.

  25. I too just agree most times, work on things I know will break and then show to management alternate solutions. They somehow appreciate this and not push back so much when they learn to understand that I am motivated by getting the job done right versus avoiding it. They need to see you are a team player first before liking you as a person. Of course having to be financial free would definitely get me more vocal. I am almost there – just another 3 years and I think I am good.

    1. Correct. One must be LIKED first. And people they like are generally very agreeable and supportive. The higher you go up the corporate ladder, the more POLITICAL it gets. A massive support network must be created.

      I was shooting cannons LEFT and RIGHT the last two years. I didn’t care. I was sick of the BS, the non correlation with performance and pay, and freely spoke my mind. Of course, I wanted what’s best for the company and organization, but I would regularly call out absurd things.

  26. Financial Canadian

    Sam, you mentioned that you were limited in your career by your tendency to butt heads with people you disagree with. I’m the same way, but I view it as a positive trait – if we are all too shy (or too afraid of offending people) to voice our opinions, than our businesses are much more apt to make mistakes IMO. The trick is doing it politely (something I definitely struggle with).

    Great post!

    1. It’s only a positive trait if your boss doesn’t think you are hard to manage and disagreeable. It’s actually an annoying trait from a manager’s POV.

      Everybody will reach a limit to how much stupidity, politics, and BS they could take. My limit was at age 34, but I had a back up plan.

  27. Great post Sam. I’m looking forward to achieving FI one day so I can come out of my shell too!

  28. Designing A Frugal Life

    Being agreeable generally makes people like you, so I strive to be agreeable. Just saying “yes” isn’t always the only way to be nice and agreeable though. The team I’m on is product driven and we have to have collaborative conversations in which we accept, question, and reject a wide variety of solutions proposed. Being respectful of everyone’s ideas and suggestions though, builds a very nice work environment in which we can ask for solutions to things without prescribing said solution. It’s sort of like the improve rule of “yes and”. Don’t just say “yes” and stop, say “yes and add something to propel the conversation/project forward.

    Of course there have been other times on other projects where it’s just easier and more beneficial in the long run to say “yes” and go with the pictures the lead stakeholder wants and in those situations, I definitely say “yes”.

    Being able to “vote with my feet” is something I’d love to be able to do, but I would have to feel very strongly about something before I stop saying “yes” and walk out the door.

    1. What happens once financial independence is reached is your tolerance for BS goes WAY down. If you notice carefully, there is a lot of people who are faking it in their role because they don’t have a proper grasp of the strategy, creation, and execution part of their duties.

      I am constantly surprised by how some people get THROUGH the interview door and land their jobs. Truly, I am amazed. Now I am a total proponent of going through 20-30+ interviews as they do in banking, strategy consulting etc. Once a virus is let in, it will ruin a company.

      See these two posts:

  29. Happiness in the workplace is an interesting challenge. Everyone wants to make themselves happy, but if you’re working as an employee, you don’t always get to call the shots.

    I do believe that if you’re working for someone else, you do what is asked of you (as long as it’s legal and moral). If you don’t like it, get another job. If you don’t like someone else telling you what you need to do, then you aren’t employee material and should chase after something entrepreneurial that makes you happy.

    As a side note, I do agree that you can get some good content if you go back to work. Toying with Uber definitely gave you a couple great posts!

    — Jim

    1. Yes! Uber driving gave a lot of great insights into people of various socioeconomic backgrounds. I’m always seeking an interesting story to tell. And talking to 3-6 random people an hour about what they do, what their thoughts are on the property market, tech scene, economy, etc is like the perfect way to interview people for stories.

      There’s something very liberating to be able to serve someone. Maybe it’s b/c that’s was part of my job for 13 years. We miss what we are used to. I enjoyed serving people most of the time. There’s a nice sense of reward.

  30. Apathy Ends

    A lot of times I start with a yes ma’am/sir and then give feedback after trying it their way on how I want to do it or what should change.

    No one likes hearing their idea/technique sucks, twisting it to fit is better received. I do work at a place with a lot of freedom though – as long as we deliver consistently we are good.

    Finding a way to be honest without stomping on your boss is a great skill

  31. There are many points that you’ve made in this post that show how advantageous being financially independent can be in your position. You don’t have to rely on the people making bad calls, nor are you bound to them seen as you’re independent.

    I am kind of in the position you describe where my boss isn’t very inspiring. I don’t see my long term future there, just long enough to perhaps see through my further education whilst we also build up our (tiny) blog.


    1. KP at PassiveFinance

      +1 for having an uninspiring boss…4th one in a row. I’m starting to think thats one of the requirements for becoming one. I’m so not made for corporate life! It’s a good thing I had the discipline and put in the effort to growing my passive income when I started out a few years ago, otherwise I’d be totally lost.

  32. With your financial background and the writing skills, have you ever considered creating a startup. I.e. FinTech one?

    I see perfect match of your skillset and the needs of a startup.

    Though enough challenge to chase away boredom.

      1. Whoah, that’s one massive quality-loaded post on startups. Haven’t read that one on FS before. Thank you!

  33. I’m FI and recently went back to work a temporary assignment at the school where I was a total conformist for more than 20 years. I rose the ranks of teacher, lead teacher and then administrator and when things got rough with the leader of the district, a bunch of us left. There was no inspiration and our souls were being “sucked dry”. But I didn’t butt heads when I left, so I’ve been welcomed back with a nice per diem rate for this assignment – and people feel I am “rescuing” a sinking ship. I’m loving the freedom I have now to speak my mind! But I also speak my mind with experience and examples, not just opinions – people listen now and ask me questions, rather than complain. I’m glad its temporary though – because both you and Warren Buffett have it figured out – “I did decide early in life that my favorite employer was myself”!

    1. That is a great thing about being very agreeable w/ your old employer to invite you back! One of my consulting clients who I helped engineer her layoff did the same thing. 35% higher rates, total flex time, ZERO stress anymore. She is so thankful.

      I might be able to go back to my old employer as the SF manager left and there’s been plenty of turnover at the top. But I think there’s a lot of other exciting things to do. Got my share of finance right here :)

  34. KP at PassiveFinance

    Great post, Sam and I couldn’t agree more. I share some of the same traits as you, I find it hard to fake my feelings (and it has proven to hurt my ability to move up in an org where I dont respect the abilities of the people above me). Been a long time reader, maybe it’s the right time to buy your eBook.

  35. At this point in my life, unfortunately, I am obligated to either make the leadership at the office very happy or to be very agreeable when I disagree. I’m being paid a lot of money to “play nice,” so I don’t mind and can swallow my pride when need be.

    That’s the life of a corporate manager when you’re bringing home 95% of the household income. I don’t mind too much as I’ve done the math and know that I am working my way out. I know that I’m in the top 2% of household income which helps as well and seeing the light at the end of the tunnel gives me peace of mind.

    If I had enough F-You money in the bank, I would have a different attitude!

    I think you have a great setup right now. You are your own boss and can enjoy the freedom and still consult when you’d like which gives you a taste of what you left without any commitment. Hopefully, I will be in a similar situation in a few years time.

    Good food for thought!

    1. Ah, but once you have F-You Money it’s actually hard to tell people to F-Off! It’s nice in theory though.

      What happens is this: a part of you likes to get told what to do by people who are not financially independent and don’t have the experience you do. You enjoy entertaining their ideas and their requests partly b/c you are curious, and partly b/c you begin to enjoy being told what to do b/c nobody ever does anymore. It is the most peculiar thing!

      The startup industry is very “fake it until you make it,” which is quite exciting as a writer. The human dynamics are wonderful.

      1. +1 to this comment.

        That was me exactly — nice, high-paying job with enough money to retire but I just couldn’t push the button.

        Then I did and life’s been GREAT!!!!!

        I know, Sam, you told me so…

        1. Haha, glad you are enjoying that great life! Don’t get too bored now OK? Well, you’ve got a blog or two you’re running and your family. So I don’t think boredom should be a problem! Looking forward to that guest post!

      2. KP at PassiveFinance

        I haven’t experienced this yet (because I haven’t had the gonads to quit my job yet), but sounds like a quality problem I would love to have :) But it makes intuitive sense, and I can see why you feel like that.

        One of the reasons I haven’t quit, is fear of getting “bored” and a fear of being able to get back into the job market, should I need to. I know, they’re excuses, but I want to make sure I land on my feet before I call it quits. As I get older, the more risk-averse I get.

        1. One of the BIGGEST surprises I found was how EASY it is to get back into the job market actually, especially if you are in tune with the industry you care about and run a blog, like you do.

          Employers want self-starting people who are entrepreneurial. If you can build a brand, grow an audience, and survive in the woods by yourself for years, they’d love to have you as a team. The opportunities are ENDLESS.

          The caveat is this: if you survive for so long and get too big, they won’t want to hire you out of fear of you getting bored too soon. Hence, one of the benefits of Stealth Wealth.


          1. It always baffled me that employers would want someone who is “entrepreneurial”. I mean, I see the qualities behind the label, but think about it. If a candidate was truly “entrepreneurial”, wouldn’t they start their OWN business? Like an entrepreneur? They’d certainly be less likely to stay for the long haul. An entrepreneur-at-heart is really gonna stay with one company for the long haul? That’s not an entrepreneur; that’s an employee.

            ARB–Angry Retail Banker

            1. LOL, you are right. An employer wants an employee to be A LITTLE BIT entrepreneurial and to be proactively thinking ahead like an owner. BUT, if your employee gets no equity, then your employer is pulling a fast one over the employee!

    2. I’m in a very similar position and I do have F-you money. I go to work every day and have to put up with stupid decisions and pretend to support them. But I haven’t pulled the trigger because of three things:

      1) I get paid a ridiculous salary and benefits for very easy work and somewhat flexible hours.
      2) I’m in tech and in my mid 40’s. I’m feel like I’m riding a wave and jumping off before it crashes doesn’t seem smart at all. In the meanwhile I continue to collect more F-you money. I highly doubt I could get back in if I leave and decide I want to come back after a few years. I’m “over-the-hill” in the industry and me leaving would lead to my position being filled by a younger person. I’m not at the VP level that would help the prospects some.
      3) I know better than quit when I can get laid-off instead. I know it will happen– its just a matter of time.

      The nice thing about F-you money does for me is to give me some psychological separation from the stupidity and frustration. When I know I could leave and survive very nicely if it came down to it, magically the issues just go away in my mind. Lots of people ask me how I can remain so calm in seemingly stressful situations. That’s how.

      1. May I ask what the F-money amount is? Just a ball park figure is fine. I’m in tech also in my late 30s and everyone seems to have different number. My personal amount would be around $4mil liquid cash or stock. I don’t have F-money, but have enough to walk away for decades, but similar to you, know that my position will be replaced by a younger person, so I’ll wait til they get rid of me with pay.

        1. My number is $3M liquid but part of my plan is relocating to a lower cost area. Yep, I’m not walking away without getting paid to do it either.

        1. Its more like jumping off with a nice expensive parachute as the wave starts crashing. I work for a big company so they pay pretty well to leave.

          I just took the FU money survey. I didn’t see it before. That’s a great post too!

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