All My Bosses Are Broke

Well, not exactly, but yours might just be


It’s good to be the boss, right?  At least that is what we are taught.  Work hard, get promoted, and become the boss.  With being the boss comes power and increased responsibility.  And of course, there are the rewards of some fancy title, maybe even a parking spot, and financial compensation – the slightly larger bonuses and an increased salary.  In some industries, that increased salary is only slightly higher but still remains a perception that ‘the boss’ is well off.

Is your boss in an overall better financial position than you? Higher net worth? Less debt?

I have been in my career field for almost 16 years.  And there has always been a strong emphasis on personal development and the need to continue to move up the ladder.  And I have done that.  I have many professional certifications, degree, overseas experience, and have led others on projects, large and small.  It is a good thing to work in a career field where personal growth is not just encouraged, but required.

However, as I fill out my annual ‘Individual Development Plan’ for which I am required to lay out my plan to achieve the next level of responsibilities, I find myself asking, “why?”  What is so wrong with staying at my current level of responsibility?  It’s not about the money.  I already make good money.  And honestly, the person at the next level up doesn’t really make all that much more than I do. There are some cases where they may even make less.

I’ve also noticed a trend in the office-place over the past 16 years.

It seems to me, when I look back at my career, many of my bosses have been broke. It’s almost as if the drive it took to reach the top has been at the cost of achieving a certain level of success financially.  These have all been people with a high level of intelligence, experience, and a solid income.

It also occurs to me that many of my relationships with bosses have been such that they have opened up to me about their financial position.  What can I say?  I must just have that certain look so that people want to tell me about their piles of credit card debt, being upside down on their house, that huge mortgage, and of course, car payments.  I even had one boss who told me he thought it was okay to have one years’ worth of salary in credit card debt!  He actually said those words out loud to me.

Now I must admit that my current (new) boss has not revealed to me his financial position.  He may be a tough nut to crack as he seems to be even more of an introvert than myself.  So we mostly stay to ourselves and email each other as needed.  Happy little introverts!

Not All Bosses Are Broke

There have been some exceptions to this phenomenon of course.  But it is fair to say that the majority of my bosses who were all earning six-figure incomes and sometimes also collecting a pension from former careers (military) were financially strapped.  All seemed to be operating in a self-imposed financial pressure cooker.

One of the funny exceptions was a boss, who I now view more as a friend more than anything, who had come to me a few times for some financial advice.  Through a few conversations we established a few things for him: 1) a college savings strategy for his kid, which I will address in a future post, and 2) as I so nicely pointed out to him, that he was very close to crossing the 7-digit figure net worth milestone. He seemed almost disinterested.

But This Was The Exception.

Question: Do you aspire to be the boss one day so that you can make more money, which will allow you to be in a better financial situation?

I think most people will admit that part of wanting to get promoted at work has to do with earning more money. Granted there are often lots of other good reasons – the desire to grow professionally, wanting to be in charge, opportunities to work on new types of projects, etc. But a lot of times it just comes down to wanting more money.

What’s the Biggest Difference Between You and Your Boss?

In my career, the biggest difference between me and my boss is not financial compensation.  It’s responsibility.  So for now, I am choosing to stay happily at my current level of responsibility and enjoy a balance in life that oftentimes the boss does not get.

What I know is that the path to financial stability and growth is not always tied to how much money you make – especially once you reach a certain point.  There are countless examples of net worth millionaires who don’t make an impressive amount of money. They do control their budget, establish short- and long-term financial goals, and save consistently.  This will almost always win over the person who may make more money but has no control over their budget, has no goals, and doesn’t save.

Navigating Your Career

When navigating your career, be cautious in seeking that promotion solely for financial reasons.  Consider making the most of what you have without running the risk of throwing your work/life balance into turbulence.  Is that extra money really going to be worth it to you?  Are the extra responsibility, additional hours at work, and/or more travel obligations worth the extra money?

Here are some things to ponder when considering whether you want that promotion:

  1. Can you instead give yourself a raise?  Focus on eliminating debt in order to free up cash flow.  Oftentimes even a significant raise at work will only give you a net increase in take home pay of a few hundred dollars every month.  Can you find that raise by eliminating a payment?
  2. Work a side hustle in an area you are passionate about. Without maxing out your time with your professional life, you may actually have some time to do this one.  Besides, wouldn’t making some extra money on the side from something you really enjoy be more rewarding and overall beneficial to you?
  3. Really ask yourself why you are seeking more at work. Is it because that’s what everyone has always told you to do?
  4. Instead of seeking more from just one area of your life, consider adding more to another. It can do wonders for your sense of self and overall feeling of fulfillment.  Striving for a more well rounded life should be an equal goal to go along with your professional aspirations.

Being the boss has its rewards.  Just be careful what you assume about yours and why you are striving to move up the ladder.

Please note: I reserve the right to delete comments that are offensive or off-topic.

10 thoughts on “All My Bosses Are Broke

  1. First time reader here. Nice post! I think having work/life balance should come before making more money. Working in Corporate America, it seems like people are scared to be content with where they are at. I personally love my job, I think I am paid a good salary for what I do and I’m not really in a rush to get a promotion. Sure more money would be nice, but it wouldn’t change my lifestyle in any way. It would just be thrown in to my Vanguard account. As far as my boss goes, I work for a very frugal person (much like myself). I have seen her go from my manager to my director in which she is now given a monthly car allowance of $1,400 and she still drives her car from the early 90’s. Awesome.

    • Thanks for checking me out. I suspect your boss is a good saver. I”m the same way with any pay increase. It doesn’t increase my lifestyle but just my automatic transfers into savings.

  2. I’ve never really desired to be the boss before. I’ve always tried to take interesting jobs and then see where it leads me. But power is not something that I really desire in life. I would much rather have my stealth wealth and doing what I love rather than wearing a power suit and telling people what to do 🙂

    • agree. I personally enjoy being part of an effective team. everyone working together. I see right through the power hungry type. power suits are expensive too. no thank you. thanks for stopping by.

  3. I’ll let you in on a bit of a secret. In some cases your direct boss makes less then you do. I’ve been in that situation as a manager personally. It’s possible and in some cases even likely to pickup a job with way more responsibility and less or equal pay. In my case my employees were on the same pay scale, but due to seniority higher on that scale then I was as the mgr. Be sure you know what your getting.

    • Agree, i’m in such a situation, where the next level up may not be making as much as a more senior mid level manager. I’ve also seen where the manager makes significantly less than the person with the technical skills i.e. computer programmer.

  4. This is a really great reminder for everyone. Thanks for writing this.

    This past year I was offered double my current salary to take a different job. The extra money comes with a giant extra time expectation, though. It was really difficult to walk away from, but I decided that ultimately my time was more important than blindly climbing the ladder and trying to ramp up my salary as much as possible.

  5. I like what M J Demarco said. Even millionaires go broke if they spend more than what they make. It’s just simple math. Wealth is independent of income. You cannot spend $6 million a year if you’re only making $5 million.

    • “wealth is independent of income,” YES! amazing how many folks don’t get that. I see a lot of people in my industry of Defense, that confuse income for wealth. Big house, big car and totally broke.

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