Want More Money? Ask Yourself This One Question

Believe In Yourself, Squaw Valley
Once you believe, it'll start raining money

If you want more money, one of the most important things is believing you deserve to have more money. There are trillions of dollars out there for the taking. Why shouldn't you enjoy some of the world's prosperity as an honest, diligent, and talented individual as well?

I began developing my money mindset after reading countless stories of CEOs earning millions of dollars while driving their companies into the ground. They would get massive multi-million dollar severance packages for crap work that even a baboon could do. As soon as I started believing in my worth, my confidence shot up and the money started coming in.

For example, IBM's CEO got a $100,000 base pay raise to $1.6 million in 2015 along with a $3.6 million bonus in 2014, and a $13.3 million stock incentive reward payable in 2018. Meanwhile, IBM was down ~20% over the past two years while the S&P 500 was up 40% for 60% underperformance! 

For half the compensation, you and I could do just as good a job as the IBM CEO. I'm picking on IBM here because I bought the stock in my active portfolio. One day this dog will bark!

On a more common level, I've seen people who are utterly unqualified get hired for jobs making multiple six figures with multiple six figures in stock options. Every time I see such an event I'm thinking to myself a couple things. The first is, What the hell were they thinking?!

The second question is the subject of this post.

Want More Money? Then Go Get It

Top Female CEO Compensation
Source: USA Today, S&P Capital IQ. If they were men, would they be making 20% more?

For the longest time, I couldn't find any other industry that paid as well as the finance industry. For example, first year analysts out of college are now earning $80,000 base salaries plus $25,000 – $50,000 bonuses after their full first year. Dang, I wish I was 22 years old again in order to make that type of money!

When I left finance in 2012, Directors were making $250,000 base salaries plus bonuses that could easily equal a full year's salary or more. It was only a full year after I left the industry that I truly appreciated how good the compensation was.

All the tech jobs I was interested in after leaving finance “only” paid between $120,000 – $160,000 full-time plus stock options, which are a complete crapshoot. So I figured, might as well focus on my online media efforts instead of working for much less compensation in a new industry.

Found The Big Money-Making Job

After learning how much Chief Content Officers at large companies make, and reading about the Content Marketing Revolution in Harvard Business Review, I've come to realize I can finally replicate my finance income doing something else in an industry that I love. I just never thought I deserved it, until I saw someone less qualified than what I expected, get the job!

Chief Content Officers make $200,000 – $300,000 a year in base salary and have an equivalent amount or more worth of stock options. That type of compensation is definitely enticing enough for me to go back to work full-time if I found the right company to join. And it's not just the money either, but the ability to have a C-level leadership role and affect positive change.

What you'll notice as you get older is that your options for work become more limited because you don't want to go too far backwards in your career. But a CCO role is tantalizing, especially since the requirements I thought to land the role are so much lower than what I thought based on what I've seen.

Want more money? Ask yourself this one qustion:


When the NASDAQ bubble burst in 2000, a disproportionate amount of Managing Directors were laid off because they didn't cover any clients. All they did was manage a team of producers. As a result, Managing Directors wised up and began covering clients along with managing people. Having revenue associated with your function became imperative for long-term survival.

I've learned that a large majority of Chief Content Officers do not produce any content (equivalent to MDs not covering any clients). Instead, CCOs are in charge of a team of content producers, managing the editorial calendar, and maybe editing the content. Not a bad gig!

The people who make the most money actually are the ones who just tell other people what to do (and take credit)! It's the creators, the ones in the trenches, who sadly get paid the least.

This fact is consistent across all industries and all departments. Instead of creating the work yourself, you hire an agency. Instead of bringing in the business, you hire someone to bring in the business for you.

In retrospect, I should have tried my best to get the Chief Content Officer at Personal Capital in 2015. If I did, and worked for them for the next five years, I probably would have walked away with $1,000,000 in stock. How so? Personal Capital got bought by Empower Retirement in 2H2020 for up to $1 billion.

Related: If You Produce Nothing, How Do You Expect To Make Any Money?

What I've Learned As A Small Business Owner

For six years, I've been the CCO and CEO of my own online media company. I created the Financial Samurai brand, wrote 99% of the content, wrote a book, figured out how to rank well for important keywords, marketed the work, and generated a significant, organically-driven revenue stream that would make mom proud.

How many existing Chief Content Officers can say they've successfully built a profitable media asset from scratch? They might have helped grow their company's online traffic, but how hard is that really, when they have millions of dollars to spend every year on content and marketing?

So instead of looking at the Chief Content Officer as an unobtainable position because I'm too young, too inexperienced, or don't fit the mold, I'm now asking myself, why not me too? The next step is overcoming the hurdle of going back to work full-time.

Don't Sell Youself Short

Confidence is sexy. Just don't be delusional. You could probably do a better job than many people out there who make more or who are more senior in title. But guess what? They are likely older, and have paid their dues. If you really believe in yourself, then you might as well try your hand at entrepreneurship.

There are a lot of innate biases in the workplace that we must try and fight through. Old leaders often have a picture in their mind of what a person should look like (age, gender, race, background) when filling a role. This is why everybody tends to look the same in leadership roles across companies. It's up to us to fight the power and prove them wrong!

I hope many of you get motivated in making the money and landing the role you deserve. It's fun to push ourselves to see how far we can go. The next time you have doubt on whether you deserve a particular role or pay amount, write out a list of your qualifications. I'm sure you deserve more than you think!

Related: The Secret To Your Success: 10 Years Of Unwavering Commitment

Start Your Own Business

Take matters into your own hand and start your own business online! It used to cost a fortune and a lot of employees to start your business. Now you can start it for next to nothing with Bluehost.

Brand yourself online, connect with like-minded people, find new consulting gigs, and potentially make a good amount of income online one day by selling your product or recommending other great products.

Not a day goes by where I'm not thankful for starting Financial Samurai in 2009. I have maximum freedom now thanks to working on my side-hustle while working for 2.5 years. You never know where your journey will take you!

Wealth Building Recommendation

Manage Your Finances In One Place: One of the best way to become financially independent and protect yourself is to get a handle on your finances by signing up with Personal Capital. They are a free online platform which aggregates all your financial accounts in one place so you can see where you can optimize your money.

Before Personal Capital, I had to log into eight different systems to track 25+ difference accounts (brokerage, multiple banks, 401K, etc) to manage my finances on an Excel spreadsheet. Now, I can just log into Personal Capital to see how all my accounts are doing, including my net worth. I can also see how much I’m spending and saving every month through their cash flow tool.

A great feature is their Portfolio Fee Analyzer, which runs your investment portfolio(s) through its software in a click of a button to see what you are paying. I found out I was paying $1,700 a year in portfolio fees I had no idea I was hemorrhaging! There is no better financial tool online that has helped me more to achieve financial freedom. It only takes a minute to sign up.

Finally, they recently launched their amazing Retirement Planning Calculator that pulls in your real data and runs a Monte Carlo simulation to give you deep insights into your financial future. Personal Capital is free, and less than one minute to sign up. It's one of the most valuable tools I've found to help achieve financial freedom.

Retirement Planner Personal Capital
Is your retirement on track? Check with PC's Retirement Planner

Updated for the new decade

26 thoughts on “Want More Money? Ask Yourself This One Question”

  1. Pingback: Can Financial Samurai Be The Next Billion Dollar Financial Technology Company? | Financial Samurai

  2. Pingback: Candid Advice For Those Joining The Startup World: Sleep With One Eye Open | Financial Samurai

  3. The Alchemist

    Ah, self confidence! The Holy Grail. It’s a trait I definitely envy in others, and you’re right, Sam— without it, you can’t truly realize success. It’s truly the key to making real $$$. Some day I hope to figure out how to get it myself! But in the meantime, it’s instructive to watch you go, Sam! Keep it up.

    1. Holy grail for not just business and finances, but perhaps everything?

      It’s fun to observe all the funny things hat happen around me and share them with the community.

      Endless amount of things to write about!

  4. Adam @ AdamChudy.com

    Everybody started somewhere. Might as well be you. I try to always think the same.

  5. Gen Y Finance Guy

    I ask myself that question any time I come across someone both online and offline. It is a very empowering question to ponder. We tend to put success on a pedestal, when in reality it is just a result of consistent hard work, combined with the right mindset.

    Henry Ford hit the nail on the head when he said “Whether you think you can, or you think you can’t–you’re right”.

  6. Interesting take on the subject of content writing being an exploding new industry… I remember graduating university in the early 2000’s and lamenting the fact that the traditional journalism industry was falling apart. This might be a good segue back into the field, as I’ve been freelancing on top of my 9-5’s for the past decade. Appreciate the heads-up, Sam.

    Perhaps it’s my group of friends, but if anything I’ve seen the opposite problem of “why not me”… as in folks who think much more highly of themselves than they should.

    1. It’s coming back BIG TIME. With Verizon buying AOL on 5/12/2015 for $4.4B, it’s all about acquiring content at any price!

      The key is to not just be a journalist, but be the journalist AND own your vertical ie the site. Then you are the creator and the business person.

  7. Believing in yourself, especially the fact that you deserve it, is a key component of success. However, you do need the ability to do what you’re expecting. Often the higher you go up the management chain it’s less about knowing what to do than it is knowing what not to do – the ability to cut to the core of the problem and ignore the noise. And that only comes with experience.

    Depending on your upbringing, often your generation, you may think you deserve more than you do, or less. But digging deep to find your limiting beliefs and eliminating them will make you more successful, whatever they may be.

    1. The higher you go, the more POLITICAL it gets, which is why developing a massive support net work is crucial.

      I like power, but I don’t like power enough to be an amazing politician in the work place. Towards the end of my career, I spoke my mind, and that was the start of the end.

      1. Joe Sixpack

        Sam, can you make a post on this topic. I am pretty early in my career and only have ever been low on the corporate totem pole, but I’ve always had a feeling things get more political the higher you go. What were your experiences with this?

  8. Sam, for what it is worth, I spend very little time with 95 percent of the sites that I used to visit, but I still come here almost daily. From my foxhole, you’re doing something right with content!

      1. Mostly, they don’t produce good and consistent content or content that I find interesting. There is this rampant hucksterism in much of the blogging community that I’ve always found distasteful or inauthentic.

        The only way I’ll pivot and go back to writing online is if I can convince myself that I can provide something of real and lasting value. I think you do that routinely.

  9. I think believing in yourself is a massive part of the equation, but a little bit of luck is always a pretty important ingredient too. It’s so easy to come up with hundreds of reasons why you can’t do a certain role, or why you might not be good enough, so learning to not take those voices too seriously is important – and I’ve had those thoughts many many times in my career! But I just finished my first day of work yesterday in a new firm, at a more senior level, and even though it’s right in my sweet spot of skills, holding on to that belief that I can do the job and am worthy is an absolute priority. I definitely wouldn’t have had the opportunity without that mindset (and the requisite luck)!

    1. Ah yes, luck is crucial. Let us never feel entitled or forget the important component of luck. Congrats on joining your new firm. Have you now eradicated the idea of early retirement with your new role?

      1. Quite the opposite – I’m nowhere near early retirement potential yet, but the pay rise that this job provides will make it a little more possible – but it’s still 11 or 12 years away with a best case scenario! A big mortgage on a new family home has a lot to do with this, but wouldn’t change it as couldn’t be happier with where we live and our current lifestyle.

  10. I’ve thought of that question numerous times. I used to work at the Paula Deen Store a few years ago. I saw that she was making a lot of money off cook books, recipes and t-shirts. I thought to myself if she could do it so can I. I sold tripled my investment with my 1st t-shirt design. My sites are now on to bigger and better opportunities. I know that I will get to six figures sooner than later.

  11. Why not me too is a GREAT question. I certainly didn’t ask myself that question early enough in my career. But better late than never! Believing is really important, which hasn’t been my a big strength of mine, but I’m getting better at it. The fact that I was able to negotiate a severance to leave my job after reading your book is my best example of “why not me too?” I had a lot of doubts for the longest time, but once I started believing and asking myself why not me too, good things started to happen!

  12. Kristin @ Brokepedia

    I think this advice applies on a smaller scale outside of entrepreneurship, too. At one of my first jobs, I put in notice when I got an offer somewhere else that doubled my salary. I didn’t even think to ask the higher ups to match, because it was more than my boss earned. I figured if he’s not “worth” that amount, I can’t be. But then they did make me an offer. Maybe that’s not surprising, considering they had another company to contend with. But I found it interesting that I never asked for a raise and limited myself to thinking I didn’t deserve to earn more, when the whole time, they were willing to pay me more than my boss. “Why not me?” is a great way to put it, and I think it can apply in a lot of other income scenarios, but entrepreneurship seems like the ultimate way to put it to use.

    1. I think people would be surprised how many owners of smaller private companies pay themselves next to nothing. If they have to get scrappy they will take it on the chin to keep their team around and keep their baby alive. I also know executives at medium sized companies that will not take a bonus during the hard times but still try to do what they can for their employees.

    2. Indeed. If you don’t believe, you don’t ask. If you don’t ask, it’s rare someone will voluntarily just pay you that much more. A little bit, yes. But not something significant.

      In order to keep my old bosses not too far away from market compensation, I had a serious heart to hear conversation every 1.5-2 years.

      Now that it’s back to bull markets, now is the time to really ask. Amazingly curious people are making big bucks. Why shouldn’t we all?

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