Dogs And Wolves

Dogs vs Wolves

Note: This post was first published in March 2021 and updated in October 2022

Fifteen or so years ago, I decided to burnish my educational credentials with an accounting designation.

Having survived the initial set of grueling exams, I was admitted to a year-long “professional development” program.

Sadly, that meant that once a month, I had to spend an entire weekend holed up in a conference room in a suburban hotel, together with a bunch of other accounting conscripts.

Not exactly what a 25-year-old wishes for, but such is the price of climbing the greasy pole professional advancement (or so I was told).

It was in that program that I met Kelly.

Free Soul

In her late twenties at the time, Kelly had just come back from an early career “gap year” of sorts.

Having saved enough money in her first job out of college, she packed it in just three years later – and went on a solo journey around the world.

In just over a year, Kelly did more travel than most people do in a lifetime. During our coffee breaks, she would entertain us with stories of traveling in places like Tibet, Bangladesh, and Peru.

Wistfully, the rest of us would stare in the window (facing out onto a highway), and dream of a life full of adventure.

Being holed up in an accounting session on a Saturday morning certainly wasn’t it.

However, it wasn’t all smooth sailing for Kelly.

Upon her return, she started looking for a job.  With a great college degree and solid work experience, Kelly was a shoo-in for some fantastic roles. To top it all off, the job market was absolutely buoyant at the time.

Except for that damn gap year.

Every single interview she had, the (un)spoken question loomed large:

“Are you going to do this all over again in a couple of years and leave us hanging?”

Frustrated, Kelly signed up for the accounting designation.

A little further down the road, she was finally able to use it to “reboot” her career and land a plum role in a government-owned corporation. But to say it was a rocky ride would be an understatement.

Fact Pattern

Over the next years and decades, I’ve seen a variety of recruitment “models” up close, both as an employee and a hiring manager.

The classic “let’s hire an MBA with a massive student loan” approach. Grant a signing bonus – but put a clawback clause in, guaranteeing a period of modern-day servitude.

The “PSD” filtering approach (poor, smart, with a deep desire to get rich), so beloved by Jorge Lemann during his time at Banco Garantia.

Alternatively, a “married, with kids and a big mortgage” will also do. As a very senior banker once confided, this socioeconomic type was his favorite hunting ground when looking for new employees.

I’ve even met people who specifically screened applicants to zero in on those from third-world countries and in dire need of a sponsored work visa. Positive discrimination at its best.

What gives?

Well, as it happens, coming off a work visa is a multi-year process.

While it plays out, you are essentially at a mercy of your employer.  Losing your job typically means losing your residency status.  Not going to get any pushback from this employee, lest he or she want to go back to the country they were trying so hard to leave?

And then there’s the good old “make sure to have a good explanation for all the gaps on your resume” spiel.

God forbid you happen to be the kind of person who dares to take a break between jobs. You better have an explanation for degenerative behavior of that sort!

The above are just a few “signals” you can emit, willingly (or, more often, unwittingly) in the job search process.

But what it all ultimately boils down to is that your employer will always want to have as much leverage as possible over you.

And if you want to land a job, you better signal that you are okay with that construct.

How To Own Another Person

I’ve always been cognizant of the above dynamic – which is why I rarely speak of my entrepreneurship experience in job interviews.

As with any social games, it’s something we all implicitly acknowledge, yet rarely explicitly admit.

Which is why I thought it was fascinating that Nassim Taleb took a proper run at it in his book, Skin In The Game (separate thanks to one of the readers for flagging to me – you know who you are!)

He sets the tone with the very title of the chapter (“How To Legally Own Another Person”) and goes on to say:

Someone who has been employed for a while is giving you strong evidence of submission […] displayed by the employee’s going through years depriving himself of his personal freedom for nine hours every day […]

He is an obedient, housebroken dog.

Now, Nassim isn’t as one-sided as it might appear.

He does acknowledge that for a long time, companies held up their end of the bargain, by providing lifetime employment… until they didn’t.

Which means that:

The company man has now been replaced by the company person.

For people are no longer owned by a company, but by something worse: the idea that they need to be employable.

And finally, there’s a statement that any banker (or highly paid professional) will recognize – if not necessarily admit:

The best slave is someone you overpay and who knows it, terrified of losing his status.

(Re)gaining Agency

To be fair to Nassim, he does give a couple of hints on how to even out the balance of power.

Making a lot of money for the firm, having a crucial skillset, or having options are all part of the recipe.

And while he clearly isn’t afraid to hurt some feelings (are you an obedient dog? or a free wolf?), he also points out the explicit trade-offs.

Sure, a dog’s life might well end (and often does) when his owner passes away. But wolves face existential risks every day of their lives.

Yes, it’s uncomfortable losing that biweekly paycheck you’ve grown so accustomed to. But how about not knowing where your next dollar will come from?

That is, as Mr. Taleb eloquently puts it: freedom is never free.

There are a couple of lessons to be learned here.

Clearly, you have to be highly strategic when it comes to navigating the relationship with your employer.

Honesty is not the best policy. What your employer wants out of you, and what you want for yourself, are two wildly different things.

In other words, keep your lifestyle aspirations to yourself.

In addition, leverage is a two-way street.

You can even out the balance of power by cornering important client relationships, being the “glue” that holds a specific team together, or simply by knowing where all the bodies are buried.

Most importantly, you need to be comfortable with the risks inherent in FIRE.

As much as we want to debate decumulation strategies and safe withdrawal rates, living life on your own terms will ALWAYS be riskier than staying put in your 9-5.

Those who retired on the cusp of the current downturn are living that reality now.  Portfolios down 30%, no regular income to rely on.  I am 100% sure things will rebound (they always do), but it’s not a comfortable place to be right now.

And yet, as people at the very end of their journey keep telling us, living live on your own terms is the only life worth living.

As always, thank you for reading!

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Banker On FIRE is an M&A (mergers and acquisitions) investment banker. I am passionate about capital markets, behavioural economics, financial independence, and living the best life possible.

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37 thoughts on “Dogs And Wolves”

  1. Sad but true!
    There is less and less room for individuals these days – any wonder that true innovation comes increasingly from start-ups; which often have their own unique brand of serfdom too?

    1. Banker On FIRE

      I’ve spent the majority of my career within large corporates (think S&P 500 constituents in terms of size).

      The amount of uniformity imposed on employees is staggering. Also, a significant amount of time (c.25%+) is spent on navigating the system as opposed to working.

      That being said, the large tech companies of today are very different from what the freewheeling days of ten or fifteen years ago. The drive to exert leverage over employees never disappears.

    1. Banker On FIRE

      … especially in a tech-driven economy where you can get almost infinite leverage (in terms of scale and product)

  2. This rang true to me – I spent a long time being a wolf in (sheep) dog’s clothing!

    Though as you/Taleb say, once I had enough strings to my bow the balance defn shifts. And thus the wolf was revealed! ?

    1. I suppose they got lucky that you ran off into the wild not long after shedding your sheep’s clothing! 🙂

  3. On the flipside, it’s not all doom and gloom and I’d argue you can still extract a good life from working in a company without being a corporate drone.

    Unless you’ve already paid your dues, even going on your own means bending to clients, investors, and so on. I do subscribe to the “personal freedom” POV but I suspect that if you’re the sort of person that tolerates excessive bull***, that won’t change much when you’re theoretically running your own thing. Personally, my ego does not derive pride from simply “not having a boss” because even if you’re a freelancer or haven’t already put your business on autopilot and running smoothly without you, you’re still selling your time.

    The magic comes instead from the financial freedom to work on what you wish in any environment that you enjoy – be it your own, or someone else’s – and being able to call it quits whenever you don’t feel like it anymore. I feel that the FIRE community focuses on the RE part a bit too much!

    You can be a wolf or sheep in any environment in the end, in my experience the key is to take conscious control and agency of your career – that’s more of a mindset than a role. I’ve found that moving towards this increased my happiness and work satisfaction by a lot.

    The money – work transaction is a purely financial one, and as long as that’s clear for both me and my employer (along with the value each side provides), there can’t be any hurt feelings.

    1. As someone in a client-facing business, I fully agree. It’s challenging as heck.

      The question is who gets to capture the lion’s share of the economics? Us bankers are pretty good at looking after our interests, but at some point an extra deal or two can make our lives meaningfully worse without necessarily moving the needle on compensation.

      I do agree that having a spine (and some FU money) can go a very long way in righting the balance of power between an employee and an employer.

  4. I find all of your articles thought provoking and want to thank you again for the time and effort you put into them.

    I’m sure you’ve got a large following, but like me I’m sure the majority are ‘silent admirers’.

    Could you consider putting an ok / like / love button option so that your appreciative audience can at least let you know that we’re out here and supportive?

    Great article btw neatly summarised by you in five words…’obedient dog or free wolf?’. Awesome and memorable!

    Warm wishes,


    1. Banker On FIRE

      Thanks a lot David. If google analytics serves me right, this blog gets about 10k visitors / 20k sessions a month, which firmly puts it in the “minnow” category 🙂

      I’ll have a look at the like button, but in the meantime, a brief comment or a friendly share of the posts you like are always appreciated!

  5. I second David’s suggestion for a Like button, I enjoy the blog but rarely comment as I feel I have nothing to offer beyond a “good article!” one-liner, which seems pointless

    Millennial Revolution talk about the “f#ckoverabilty score” – points off high mortgage, private school fees etc and the more the better as far as the company is concerned. Glad I am towards the end of my career, rather than starting out.

  6. And these days the new hiring methodology is to create a great work culture that you as an employee want to be part of (compared to other gigs) and ensure hard work and productivity through this vehicle. I know because I’ve tried to engineer a great work culture.

    But no matter how you slice it the dogs and wolves analogy is very true. I’ve never wanted to be a dog, so after five years of being one I’m now back to being a wolf.

    1. Banker On FIRE

      I view it as a spectrum. Some folks are dogs, some are wolves, some are in between.

      Nothing wrong with being on either end of the spectrum, as long as you can clearly see the downsides.

  7. Great article as usual. The dog and Wolf, I watched the Harry and Megan interview recently and I thought Harry has become the “wolf”. That was clear to me when escaping the Royal household as mentioned in the interview. Compared to the life his lived and the life he now lives. He is out there “hustling” but he can’t hide his hustle.

    Also reminds me of the book by George Orwell “Animal Farm”of the horse that died giving his all(Spoiler alert ;-)), the horse was called Boxer(he was the dog in this case).

    The plan for FIRE sometimes need to be kept “hush, hush” from the employer. You are right Banker on Fire. As an ex-work college told me “It’s a bit like chess, I think three moves ahead!”(the wolf).

    The other point is some people like the safety of pay-check to pay-check but what happens after retirement? Nassim Taleb often used the analogy of the Taxi driver and the Taxi driver has flexibly to work his market and adjust. If the location he works in does not bring in much money he can move to anther locations to work. He will occasionally have a high paying customer and sometimes a low paying customer at the end he has his own infrastructure(FIRE).


    1. Banker On FIRE

      I read Animal Farm last summer and really enjoyed it. It rang especially true to me given that the book was illegal in the country where I grew up 🙂

      1. Fascinating – I read AF as a set text at school!
        Eric Blair (George Orwell’s real name) was a complex character.
        IMO a good series about him (unfortunately not fully available right now) is available at:
        FWIW, I found episode four (not available just now) about his time on Jura struggling with ill health and trying to finish his final novel 1984 very interesting.

        1. Banker On FIRE

          Nice link, thanks for sharing Al.

          1984 has been on my list for a long time btw, but I haven’t gotten to it yet

  8. Great article, and that book is easily my favourite from Taleb.

    I am a big fan of the “third way”. Once you have FU money (say 5-10x times expenses), most office politics and requirements are optional if you are not a total douchebag and you deliver on the job. Being ready to jump ship or having frugality on your side also helps.

    I’d recommend reading this excellent piece from Deep Dish on the pros e cons of freelancing,
    9 to 5 employment, and the third way:

  9. Sadly for much of my career, I was that obedient dog, and not just that, I was the type that worked tirelessly to try to please my masters (and mistresses) and was happy to get crumbs or a bit of praise in return. The thing is, at the time, I felt like I was a mostly happy Dog, only because I didn’t know any better, or rather I didn’t have any other choice.

    As I became more comfortable financially, I moved away from being that dog but whilst I don’t consider myself the wolf (which is the extreme), I’m probably a coyote, though hopefully not as bumbling as the cartoon Wile. E version!

    1. Banker On FIRE

      Hah, yes – praise is the favourite tool in the arsenal. When the employer is too stingy to part with some cash… let’s give them a good old pat on the back instead!

      Same for “step-up opportunities”… basically opportunities to do more (sometimes much more) for the same amount of money.

      To be fair, there’s much less of this kind of stuff going on at investment banks (at least in the front office). They are ruthless places but that cuts both ways.

  10. As someone soon entering the entrepreneurship life and leaving W2 work, I like this perspective. I’m resonating with the dog vs. wolf analogy… that’s puts some good context behind what I think I’ve begun feeling. Well said!

  11. Thanks for this article, it really resonated with me.

    I did share my FIRE aspirations with colleagues at a previous employer and didn’t feel that it hurt me in any way, but when I mentioned to my bank advisor that I was hoping to stop working at age 40, she told me I should not repeat that to other people at the bank :D. That was the first time I realized that my ambition could potentially hurt me.

    Regarding the dog vs wolf situation, I think even if you depend on *a* job as an employee, that is very different from depending on *the particular job* that you currently hold. I’ve found it very helpful to frequently be in talks with other companies to know my market value and to have options. I’ve also on occasion generated and used leverage that way, to get more from my current employer. So I think it goes both ways. I’d recommend every employee to not be afraid to let e little bit of wolf come out every once in a while 😉

    1. Banker On FIRE

      Thanks LadyFIRE.

      Agree and I have done both in order to make sure I’m getting a fair shake from my employer.

      With my people manager hat on, it’s true that the “squeaky wheel” always gets the oil!

  12. Keep your aspirations to yourself is so true. I remember I read a budgets are sexy article that said richard branson botched himself out of a deal by oversharing his aspirations of creating an airline company and exploring space in the future.

    Honesty is NOT the best policy. The only ones who say honesty is the best policy are parents, policemen, and more who are trying to get a confession out of you. Honesty is the worst policy ever.

    1. Banker On FIRE

      Imagine walking into a real estate deal and telling the seller you will bring rents up to market levels, evict the non-paying tenants, renovate the place etc.

      Agree that transparency is NOT how you carve out a good deal for yourself.

      1. “The best slave is someone you overpay and who knows it, terrified of losing his status”

        THIS! a thousand times this. This rang so true its basically my situation. Paid very well for my level for mostly past glories though I still perform at a very good level the effort and engagement isn’t there. Vaguely Terrified I’ll be found out as any move would involve pay cuts or high stress of huge targets, but also with multiple years financial cushion I can’t muster the energy even though I’m probably still 5 years at least away from full fi.

        A downside of Fi that people don’t talk about? That not having that desperate need to earn due to high mortgage/ living costs decreases the motivation to perform? Or maybe it’s just me.

        Equally agree with Lukes assertion that alot of corporate bollocks is optional if you do your job well anyway.

        The irony is not lost on me that I’m now coaching and managing a team of sales people including sending them multiple pipeline sheets spreadsheets etc etc that my boss freely acknowledges I rarely if ever fill in myself (the important ones I get the occasional weary reminder and do immediately so I’m not a pain in his backside). In his words ‘you do enough and I know you’ll meet your targets without them so you get a pass’.

        For now lol. Problem is I’m mostly worried that a bad year will bring this down on me and the moment I’m forced to spend my time filling in sheets to justify my bosses existence I will probably resign. I’ll have to take a pay cut but 5 to 10 years f u money banked in Isas will soften the blow. Might just be the push I need to go the entrepreneur route

  13. I’m also open at work that I want to ‘retire’ by 50. I’ve not currently found it an issue. Most people I think don’t believe me. My boss does but his view was at least I know when to start succession planning lol
    A few have shown interest and asked me about investments. I direct them to monevator and the early retirement Mr money mustache article and invite them to ask me more if interested. 1 or 2 do I think it will always be a niche thing
    I think the pull of the hedonic treadmill is too strong for most

    1. Banker On FIRE

      Re: your first comment – I see this in banking a LOT. Overpaid mid- to senior-level bankers who know they wouldn’t make nearly as much money elsewhere. Terrified of leaving, yet unhappy with the current setup.

      Interesting your employer pretty open-minded about retiring by 50. In banking, giving off a whiff of being financially stable is usually not a good idea, not least because it will imply you won’t be as upset if your bonus comes in below market…

  14. Very true and it will only get worse. Even now companies are using analytics to help determine this and further once they hire you it doesn’t stop. As the question becomes what is the minimum raise we can give that person. Oh new mortgage or new car, they aren’t going anywhere give them less.

    1. Banker On FIRE

      That’s right.

      And then there’s the scary post-covid reality. “If you can do your job anywhere, someone anywhere can do your job…”

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