
I had nearly thought that every topic on personal finance had been thoroughly exhausted, until I came across the headline, “Why we’re too afraid to get rich”, by reporter Alyssa Pry.
This notion of “fear of wealth” comes from Jen Sincero, author of the book You Are a Badass and its follow-up title You Are a Badass at Making Money.
Sincero feels that many of us are afraid to get rich. My immediate reaction to this notion is “clickbait!” But I’ll reserve judgment and remain curious, as we explore the psychological hang-ups we have about being loaded.
The “Badass” author suggests that a primary fear we have is essentially the fear of being a douchebag. So how do we avoid becoming one of those, when all we want to be is a badass? We certainly have our wealthy types who are generous and down to earth… Dare I say “loveable?” Tom Hanks? Barbara Bush (Rest in Peace)? Oprah?
But when we think of wealthy people, we generally default to the bad actors. I’m guilty of this. Just yesterday while riding home through a ritzy neighborhood (NOT mine), I witnessed a drunken pro hockey player crash his big black Cadillac Escalade into a parked car.
Douchebag. He’s lucky he didn’t take out the nearby dog-walker and his sweet little Yorkie.

Is Anyone Honestly Afraid to Get Rich?
At any rate, if avoiding being a sinister rich person is a barrier, I need to learn more. Are we so judgmental of wealthy people that we subconsciously sabotage our opportunities to become rich?
Sincero claims in Pry’s report that “… in our subconscious, we think rich people suck, [and] we think that if you get rich, it means you have to compromise your morals.”
Whoa. I wonder what Dave Ramsey thinks of that? Or how about the televangelist who’s prayerfully asking for a private jet?
In Pry’s piece, Sincero comes around to my more common, pedestrian perspective. The author admits that to become rich, “…you have to be open to taking risks, and doing whatever you can to reach your goal. It’s not easy for everyone.”
Okay, I can get behind that. But fear of taking risks and breaking through comfort zones is much different than trying to avoid being a wealthy douchebag.
This leads me to this quote from Sincero. One that might have a little Walter White ring to it:
“I find that in my own life and with the people I’ve been coaching when people decide to get rich, they’re available to do things that are outside of their comfort zones and stretch themselves,” she says.
“You have to be available to do whatever it takes, and that’s where people get tripped up.”
I don’t think by a long shot that Jen Sincero is proposing we drop the legitimate work we’re doing now, to take on some nefarious meth lab operation in our basement or Winnebago. Though that would certainly qualify under “do whatever it takes.”
3 Ways to Legitimately Make Money include:
1.) Taking night classes, and accruing student loan debt, to earn a part-time degree
2.) Investing your home equity balance as a down payment on your first rental property
3.) Making your boss’s life super easy and letting him or she knows about your career aspirations
How Rich People Think
This is far from new territory. A Business Insider post from 2015 dives deeper into the topic. In the article, “How Rich People Think” author Steve Siebold shares that “The biggest thing holding back most people from striking it big are their thoughts, beliefs, and philosophies about money.”
Fear, and specifically, the fear of rejection and failure, is at the root of the problem. If we want to make it big, we have to think and act big. In my case, maybe that means I should be applying for VP jobs in my own company, or elsewhere. Maybe the VPs at my company should consider striking out to form their own small companies.
Many of us do get trapped a bit in our comfort zones. Complacency can set in quickly, especially when other obligations take priority. Raising a family, taking care of aging parents, or minding your health problems are valid barriers. But not necessarily “fear-driven” barriers.
That said, there are quite a few worker bees out there who love to play the victim card. You know the type. They’re not getting ahead because of someone else’s problems, never their own.
It’s their boss’s fault, their company’s fault, or their colleagues. Executives and entrepreneurs who navigate to success tend to focus inward and typically avoid this destructive mindset.

How to Overcome Anxiety About Money
A companion piece by Ms. Pry gives Sincero a chance to explain the flip side of the equation. If we avoid fear, there are steps we can take to shorten the path to wealth. Let’s examine these tips and see if they pass the Cubert test. I get to play the skeptic.
“It actually is a lot easier to get rich than one would think,” Sincero says. “Back in the day I was always broke and was living in a converted garage at the age of 40 and then I decided I was unavailable to live my life with that reality, so I decided to change it.”
Of course, our hero went on to sell a bazillion books, not unlike Harry Potter author, J.K. Rowling. When people like Jen Sincero come along to share what’s worked for them, it would be wise to listen methinks…
Jen Sincero’s Tips on Sustainable Money Making:
1.) Have a clear, measurable goal. In other words, don’t just say you want to “get promoted” or “make more money.” Be specific! Is there a role above your current level that you might just qualify for? Odds are you do, but what are you doing to network and improve yourself, in anticipation of opportunities? If you want to make $100,000 or even $200,000 a year, be prepared to take incremental steps to achieve that goal.
2.) Examine and adjust your social circle. This is tricky. I’ve had my share of friends and acquaintances who’ve struggled and muddled their way through their careers. I’ve also had friends who’ve landed nicely in the six-figure territory with giant houses. Thing is, I don’t base my friendships on how successful they are at making money. That’s just plain poopy. People come first. And sometimes your friends and loved ones can’t help but feel like the victim, and it’s something they can’t control. Don’t abandon friends in need. Now, if you have a “friend” who is simply a leech and a total douchebag, abandon him at will! Job-wise, zero in on mentors who have similar strengths, but who have risen in the ranks or forged successful businesses.
3.) Act like you got the raise. Visualization is the name of the game here. Dress the part, and act the part. So often, this is how that fresh-faced youngster you thought was an intern is the VP of Sales. She played the part and got hand-picked for the opportunity that presented itself. That doesn’t mean you get to go out and buy a BMW when a simple, elegant Honda Fit will do. BMW test drives are okay I guess. Anyhow, figure out the habits and lifestyles of those whose jobs you want for yourself. Does the Sr. VP of Sales hit the treadmill at 5:30 AM in the office gym? Hop on the treadmill next to him or her, sunshine!
4.) Just do it. Nike fans – this one is for you! Sometimes you just have to take action. The act of doing is powerful, especially in a corporate environment where equivocation and analysis paralysis gums up the works so much that you wonder how anything important ever gets done. Sure, you can plan, plot, and dream. But until you execute those things, you’ll stay stuck. Sincero suggests scaring yourself into action. Not a bad idea, considering the ticking clock chasing us all. Now, go make something happen!
THIS Personal Finance Blogger’s Perspective
Making money is never a bad thing. You need to know how to protect your assets with portfolio diversification. Avoid living large, but be generous. There’s a key distinction there: It doesn’t make sense to be a lonely miser to hoard your wealth. Keep a small footprint, but don’t be opposed to buying your friend’s a cup of coffee or lunch from time to time.
Remember to give to worthy causes, not out of a sense of duty but because you recognize how uneven the distribution of wealth is in this world. Compassion should be the main driver behind anyone’s desire to get rich.
And finally, know that those with super high salaries have an innate salesperson’s ability to forge strong relationships, and back up their words with actions and results. Think of it as strong EQ powered by utmost confidence.
If you bring that A-game into an arena where large salaries and bonuses flourish, you’ll soon earn what you deserve. Leave your imposter syndrome demons at the door and go kick some butt!
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i’ve never been afraid of getting rich but have always limited what i am willing to do to get there in the workplace. it’s just an individual decision to remain a little skeptical and standoffish. if that means less dough then i just had to save and invest better.
i like the part about the company you keep. i have one good buddy who a real riot and always a good time but i swear there’s a hundred dollar cover charge to hang out with him. it’s always about doing the stuff i rarely do: a couple of hours at the horse track/golf course, drinks at a bar (i like my booze at home), eating out, concerts. sometimes i just accept it and eat the c-note but those occasions are getting more rare.
I’m a bit like that too with my day-time gig. A bit of a pot-stirrer. Not unlike the blogger side of me, actually.
Thanks for sharing about your spendthrift friend. Those are tricky ones to keep after you’ve chosen a more frugal path. But you can always meet half-way I think. Frankly, I don’t think I could stand to be around too many high powered execs in a friendship – the ego doesn’t stay back at the office.
Pretty good advice. I think the only thing I might add is I see another reason many are not rich. Frankly VP jobs and entrepreneurial opportunities are not for everyone. Long hours, difficult decisions, etc. Not everyone wants to be Bill Gates or Musk. Enough is important, rich maybe not so much.
Thanks, FTF! Those jobs are for the birds if you ask me. The only reason to pursue them, is to challenge yourself and position yourself for early retirement. I think it’s a win-win for the company, as new (younger / cheaper) talent emerges in the ranks.
I’d argue that “enough” is the best place to wind up. But I couldn’t resist exploring this idea of “fear of being rich”
I definitely think fear is a huge factor which limits many people. Nobody wants to fail, and it’s a lot easier to just not do something instead of try it and fail. I think it’s the ones who do try and fail, and then learn from those failures that really can make it to that next level.
Agree, good sir! Even those who take those first steps can get stuck later on, when they think they’ve reached their “sweet spot.” Then there are those who simply can’t stop. I’m more the former, but if I see a rental house I like…
I grew up in a pretty well off family, in an area where friends drove to high school in fancy cars, so I’ve known since an early age from personal experience that rich people can totally suck, or they can be totally awesome. Though it was always a point of pride that my friends never knew how well off my family was until they came over to my house for the first time, because I figured then I didn’t exude the “rich b**ch” mentality. And now as an adult, my husband and I make far from a “rich” salary 😉
That’s interesting to know, Angela. I wasn’t aware of that from your origin story. I came from a middle-middle class household, and I think now we would qualify for upper-middle. Ironically, we live in a smaller house, with smaller cars, and no boats. But we do enjoy fancy vacations some times.
I will tell you that once I started getting a higher and higher net worth it did come with some increased fears. As the balances in my retirement accounts and taxable brokerage accounts grew, a mistake that didn’t mean much in the past could now mean a swing of 5 figures. And obviously being wealthy does have it’s own challenges beyond that (higher target on back, especially in my profession as a physician). But yeah despite the increasing risks as you get higher up in wealth it is still worth it as becoming financially independent carries with it so many beneficial rewards.
That’s an interesting perspective, X-Ray. The bigger target on your back is no fun at all, but there’s liability and umbrella insurance for that!
Maybe we need to push ourselves hard to maximize money now, in order to shrink our timeline to FI later. A cause and effect dynamic that Mr. Money Mustache would acknowledge.
I agree with Young Fire Knight and Fulltime Finance. I have never been afraid of becoming rich because it would make me an a**hole. I have been afraid of wealth for the same reason I’ve been afraid of success… the fear of failure. The smarter, wealthier, healthier, etc you are, the more scrutinized you become. Plus, the fall from the top is a much longer way down than hanging out in the middle of the ladder.
I think we do self-sabotage at times, rather than taking the more difficult road. And it’s true that some people don’t want to put in the long hours and hard work required to become wealthy. They are happy staying stagnant and living with less. I ride the line between those two thoughts. I want to be well-off, but I don’t always want to put in the work. I want vacation time and great healthcare. I grew up in what many would consider an impoverished family, so $50k a year is rich to me.
I found the perfect life balance/income/success when I joined the Air Force. haha! Of course, that route is not for everyone, but it works for me and many others in America. I love that you tackled this issue!
Good on you, Liz! Fear of failure is familiar to me too. There is that “imposter” phenomenon that tends to happen as well, when you reach a new height you don’t feel you necessarily deserve.
Self-sabotage is a great way to put it. I tend to think of the frog sitting in a pot of water on its way to boiling. We get comfortable and avoid struggle and challenge. “Stagnant” is a good word to describe it.
Thank you by the way for your service! (And thanks for stopping by – long time no see!)
This is such a nice well-detailed post about the mindset which can hold us back from getting rich.
I read Steve Siebold’s book – How Rich People Think – some time back and it was an eye opener. It’s only some time back that I have consciously tried checking on my internal chatter of rich = bad/mean.
Also, the bit about being specific and actually doing things is so important. I am a marketing professional interested in Personal Finance. I attended a Carl Richards talk and later asked him if he thought I could make the switch. He told me one thing which has stuck with me – there is one difference between winners and losers, losers talk while winners go and do it. We’ll, I am now a CFP and figuring out my next steps.
This post sort of put into context the learning I have had over the last few months!
Thank you, Aparna! I may have to give that Siebold book a look-see. It is a common perception many of us non-rich types have of rich types!
Congrats on your CFP. You know, that’s how I tend to roll these days myself. Rental properties? Never know til you jump in. Airbnb? Same thing. There are doers, and there are dreamers. When the two meet, watch out.