I have had the privilege to work with a lot of very successful people over the years. I have learned a lot from seeing how they work and think. Their achievements are rarely accidental.

Of course, there are exceptions.

Like the hedge fund manager whose personal accounts I handled. I was so impressed with this guy. He had two private jets and seemed like one of the most brilliant businessmen I had ever met.

He was brilliant.

At running a Ponzi scheme.

I found out by way of the cover of the Wall Street Journal on an early Monday morning upon arriving at my office. But people like him are the extreme exception.

Most successful people are incredibly diligent and of extraordinary integrity.

Medium is full ‘how-tos’ on their habits. I decided that for this story, I’d approach things from a different angle.

In my time working with high net worth people, I wouldn’t say that all are successful. People inherit money. Some people earn a lot and spend even more. Some just sabotage themselves without any apparent reason.

Somehow, it seems like it’s in the human spirit to instinctively sabotage oneself.

Successful people find a way to counteract those instincts. They act out of principle and discipline.

Self-sabotaging types also have common characteristics. Having observed them for a career, here is a list of the sure signs of unsuccessful people.

Instant Gratification

Instant gratification takes too long.Carrie Fisher

We live in an instant gratification world. I’ve noticed myself getting extremely frustrated by the slight delay between pressing my request in the ATM and the money actually coming out. Nobody likes waiting. But our culture has become downright pathological about it.

Look around. You don’t have to look real hard to see people’s frustrations boiling over in supermarket lines, on the roads, and everywhere else.

If you are in the business of serving customers, it’s good to respect this reality. Your business exists to solve people’s problems. Helping them to get want they want when they want it solves a big problem for many people.

But it is not a way to run your personal finances.

The least successful people I have worked with prioritize instant gratification over the long haul. Why wait? I want to buy it now! In the words of one client, “Brent, I try to budget but then I get depressed and go to Neiman Marcus and spend $25,000.”

Comparison With Others

“Comparison is the thief of joy.” — Theodore Roosevelt

This may be the single key to unhappiness. It is also unwise to do in your finances and leads to poor decision-making. Let’s face it, no matter how much money you make or how high you rise in your career, there is going to be somebody who outpaces you.

People who insist on constantly comparing with others cannot do well because they will always perceive that they’re not doing well. Perception is reality in our minds. The harvest of sowing constant thoughts about how you compare to others is profound discontent.

This pattern can manifest in different ways. Adult kids of highly successful people who are constantly comparing each others’ circumstances. High-income professionals who resent good things happening to their friends and colleagues. It’s insecure and a big contributor to a lack of success.


“No matter what the reason, if you start to scream and shout, you look a fool, and you feel a fool, and you earn the disrespect of everyone.”—  Michael Caine

You can learn a lot about a person by watching the way they treat people. Especially the people that they perceive to be lower down the totem pole than they are. It’s uncanny how my worst clients tend to be the ones that are miserable to the receptionist, to the servers, to anyone they feel that they can push around.

They are disrespectful in general. Often disrespectful to their families. Disrespectful to their employees. And disrespectful to the people that serve them.

I have been told by a celebrity client that these types are among the most miserable, unhappy people in the world. The worse that they treat others, the more likely it is that they are not successful. High net worth notwithstanding.


“It is much more valuable to look for the strength in others. You can gain nothing by criticizing their imperfections.” — Daisaku Ikeda

There is some overlap with disrespect here. Disrespectful people are usually critical. And critical people are often disrespectful.

Having a critical spirit can often come under the veneer of politeness though. There are certain people who, when I see their number calling me, I know are going to tell me everything wrong about their day. It’s perfectly okay to vent but for some, it becomes the only way they can communicate.

The thing is that it’s mentally lazy. The easiest thing in the world is to find the things that are wrong in any circumstance. There are people that I have watched go through what should be a joyous time of their life. Milestones that happen once in a lifetime. All the while, finding fault with the most minor details within that experience.

And they’re not just finding fault with the details of the circumstance. They ruthlessly criticize everyone along the way. Sometimes politely.

Poor Listeners

“If you make listening and observation your occupation, you will gain much more than you can by talk.” — Robert Baden-Powell

You can learn something from every person. But you have to listen.

I have noticed among the people I have worked with who are not happy is that they do not listen to other people. These are the people who can have an hour-long conversation and never actually hear anything that the other person has said. If the other person can get in any words at all.

We’ve all been around the person that drones on and on about themselves and shows no interest whatsoever about the person they are with. If you are able to share anything at all with one of these types, they will immediately one-up you.

You are excited about a business opportunity. It reminds them of the time that they had an even bigger opportunity which they proceed to tell you all about in painstaking detail.

You would think that for all the talking these types do, that they would have something of tremendous value to offer. People that don’t listen to anyone else never do though. It is a trait that is sure to hold people back from breakthrough success.

Hot Stock Tips

“The individual investor should act consistently as an investor and not as a speculator.” — Ben Graham

The other traits apply to life as well as finances but this one is specific to finances.

Over the years, I have noticed that one of the biggest self-sabotaging investment behaviors is an obsession with hot stock tips. There are certain clients I could reliably count on to call me and want to ‘get-in’ on whatever cult stock is in the news.

Worse, they are trying to time when to buy and sell the previous hot stocks that were the flavor of the day a month ago. This is not investing. As Benjamin Graham put it, this is speculation.

It’s really gambling. And you can see that what these types are looking for is the thrill of a quick rise in price which sometimes does happen. The problem is that many more times it is the opposite.

In the long run, this approach is a sure-fire way to short circuit success.

Final Thoughts

There are patterns of success and patterns of sabotage of success in business and in life. I have observed a lot of people over a long period of time and these seem to come up over and over again.

You may see successful people who do some or all of these things. That is true. But their success will not be sustainable and they are likely deeply unhappy.

It’s better to focus on what you want than what you don’t want.

But evaluating yourself is also good. Does an honest assessment reveal some of these characteristics? Turn them around.

You will increase the odds of joy and fulfillment.

Have you noticed any of these characteristics in yourself or in people you work with? I want to hear about it. Please share it below.

Brent Rupnow is a Certified Financial Planner, Certified Exit Planning Advisor, Christian, adventure lover, and aesthetic.






Image courtesy of Anna Shvets.