The Road Less Stupid Summary

Business Mindset

Brief Summary

The author of this book is an entrepreneur and speaker. In this book, he discusses how most financial blunders can be avoided by avoiding stupid mistakes instead of trying to become more smart.

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The Road Less Stupid
  • Hardcover Book
  • Keith J. Cunningham (Author)
  • English (Publication Language)
  • 320 Pages – 12/15/2017 (Publication Date) – Keys to the Vault (Publisher)

Last update on 2023-12-30 / Affiliate links / Images from Amazon

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The Road Less Stupid Summary (Detailed)

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Usually, we think that some people are stupid and some are not.

But the truth is that we all have the tendency to act stupid in our own ways.

The problem is that every time we act foolishly, we pay for it in indirect ways.

And if you are running a business, it will cost you money eventually.

In this article, we’ll learn how to be less stupid and act smartly.

Alrighty, so without further ado, let’s dive right in.

Lesson #1: Don’t try to be too smart. Just be less dumb.

Nobody decides to be dumb. It often comes naturally.

Even smart people make dumb mistakes. So we should never assume that we will make wise decisions in our business.

And no matter how hard we try, we can always make dumber decisions.

So we must ask, “How to be less dumb and more thoughtful?”

Emotions make us irrational.

Emotions going up means rationality going down.

Most people just give in to their impulses.

They invest out of greed.

They make quick decisions instead of waiting a bit and giving some thought before making crucial decisions.

Ask any dumb person, and they will sound very confident.

Confidence isn’t the problem.

The problem is that their confidence is guided by their ignorance.

They think that what they believe is true.

Every bad business or financial decision ever made happened because the person who made it thought they were making the right decision.

They all made wrong assumptions about reality.

People think that many things in life are obvious, but most of the time they are not. They just think of them as obvious.

For instance, many people believe that it’s necessary to start a business based on trends. This is not true. There are so many other factors beyond trends that you should consider before investing in any business idea.

Always beware of information that seems too obvious at first glance.

No matter how thoughtful you become, you can never be too smart to not make a dumb mistake.

The point is: Our focus should not be to chase perfection while making decisions. We should try to be more thoughtful than we are in the present state, know our tendency to be dumb, and thus try to minimize the number of mistakes.

Lesson #2: When you don’t find the right answers, try to find the right questions.

Often, we get stuck while solving problems.

And wonder what we might be doing wrong.

We keep thinking about the solution, hoping that solution will magically pop into our minds. But in reality, we fail to consider the quality of our questions.

Asking the wrong questions gives us the wrong solutions that don’t solve the real problem.

In simple words, it’s not always the problems that are hard to solve. Sometimes, the problem is the way we frame our problems.

In case you don’t know about “framing.”

Frame simply means how you look at your problems.

When we frame our problems incorrectly, it leads us to the wrong solutions, and we start getting disappointed, which further lowers our self-esteem.

Let’s understand this with an example:

Let’s say you have a business, and you are struggling to run it profitably.

What most business owners do is that they say, “My business is not making profit.” and ask, “Why is my business not running?”

This type of questions may be a nice starting point.

But if you pay attention, you will find that this type of questions show complaining behavior.

Instead of asking such types of questions, you can frame your questions and ask, “What can I do to run my business profitably?” or “How might I solve this problem in my problem to make it run profitably?”

These questions might sound similar to the previous ones, but notice how the frame has changed here.

Now, instead of complaining about why your business is not making profits, you are thinking about what you can do to make it run profitably.

You have opened up the door to possibilities now.

It’s important to realize how you are looking at problems while problem-solving.

If you don’t check your frame from time to time, you might end up confused and without any satisfying solution.

Another thing to note here is that simply changing your frame won’t do the magic.

You have to believe strongly that all problems are solvable. Or, in other words, you have to believe that there is no problem that you can’t solve.

When you approach with this mindset, there is a high probability of you solving the problems.

And also remember: So many people can give so many answers, but truly genius people know how to ask the right questions first before they give any answers. This is what separates a genius from the ordinary.

Lesson #3: If you can live with the worst consequences, you can take the risk.

If you ever reach a point in business or life when you have to make a crucial decision and you are thinking, “Should I take the action or not?” then here is what you can do:

First, think about the upsides of your decision. Think about what you will gain if everything happens according to your expectations.

Obviously, this is the easiest part of the process. If you are not gaining anything by making that decision, it’s probably not that crucial at that moment. Think about something else.

Second, think about the downsides. Think about what will happen if you end up making the wrong decision.

What will you lose?

This is hard. Because it’s difficult to analyze a negative scenario, as negative emotions are very powerful. But this is important to do. If you don’t realize what is at stake, you might end up making careless choices.

When you have figured out both upsides and downsides, you might want to do a final check.

Just ask yourself: if, even after carefully considering all scenarios, you fail, will you be able to live with the consequences?

If you can live with the worst consequences, you can take the risk with less discomfort. This takes away a great deal of fear while moving ahead with your decision.

Lesson #4: Having a passion and using that passion to create a business are two different set of skills.

One can be a great artist and still be unrewarded if they don’t know how to turn their talent or art into business.

Both business owners and artists make this mistake.

Most artists believe that if they become highly skilled or creative, then they will also become successful. They think that success in one part of the game of business will transfer to the other part of the game.

Artists create content with creativity and bring ideas into reality.

On the flip side, business owners own a business and work on things like marketing, sales, taxes, etc.

When you are running a business, you have to wear different hats all the time.

You need a great product, and you must know how to market it, sell it, and ultimately make profits.

Most people don’t understand the difference between being an artist and running a business.

This is why many deserving artists remain unrewarded.

You can be very passionate about your art, but if you don’t know how to do business, you will not be rewarded.

Passion is useful while creating value. But that value must be marketed well so that the right customers buy it.

Or you can be a great businessman, but if you aren’t creating products with passion, you are likely to struggle with retaining customers.

Nobody wants bad-quality products. You must have enough passion to create quality products before you sell them.

In simple words: Don’t confuse “art” with “business.”

You must have both the skills: “How to create?” and “How to sell?.”

Just because you are good at one skill doesn’t mean that you will get good results with the other one.

Unless you see them differently, you will be confused because it is hard to identify problems when you are not clearly defining roles.

This is not such a big problem for small businesses, though.

Small businesses are run by fewer people, and not much work is to be done.

But as the business grows, you must know who is the creator, who is the operator, who is the owner, etc.

Lesson #5: Culture is the king in any organization, and it is defined by what you can and can’t tolerate.

You can hire the most talented staff, but if you don’t have a consistent culture within your organization, your strategies will fall apart eventually.

Culture is the heart of the organization.

If you are a manager or boss and you regularly find less motivated employees, then maybe your organization’s culture is lousy.

Most companies just define a culture and expect their employees to behave a certain way.

So on paper, they think they have a culture, but in reality, most employees don’t care about the company’s culture at all.

It all boils down to what and how much the manager can tolerate. For example, things like “what kind of behaviors are allowed within the company,” “how the employees will treat each other,” etc.

Simply creating a culture within the company isn’t enough.

A manager or boss must have a strategy to sustain the culture.

For instance, if there is a person with good performance and talent, but his personality isn’t a good fit for the culture, then it’s not a good idea to hire that person.

Remember, one dirty fish can spoil the whole pond.

You must protect the company’s culture and values at any cost.

The author talks about how there is always one stud professional in the office who thinks that they are immune to the company’s culture and believe that they can do anything they want because of their unique skill or great performance.

This is where most leaders fail. They decide to keep such a person, hoping it will improve their overall performance.

To sustain a culture, you must be willing to enforce hard rules.

You can’t always operate on your feelings while making business decisions.

However, there is always a limit to how much you can push your employees.

All employees have their own expectations too.

And the company leaders also have certain goals to hit.

The culture has to be healthy for both.

If employees don’t feel valued and supported, they will hop on to another company that does.

So unless the leaders sit down and think about what kind of culture they want to build within the company and create proper rules accordingly, it’ll be hard to create a healthy culture within the company.

Most companies take the culture very lightly and leave it as an afterthought.

But it’s a vital driver for any company’s growth and has a great effect on the employees and overall business.

Lesson #6: The popular advice “Do what you love” might cost you money in your business.

We have all heard this phrase: “Just do what you love, and then one day you will become successful.”

This might make sense at first because our efforts are rewarded most of the time.

But still, we can’t ignore the fact that just because you are passionate about something, it doesn’t mean that it can make good money as well.

Especially in the business world, the market doesn’t care about what the business owners are passionate about.

If your product is not useful to your customers, they will not buy it, and you will eventually go bankrupt.

In simple words, if you want to run a profitable business, focus more on building ‘what your customers want’ than ‘what you want.’

And if you are hellbound to build what you want, keep your expectations low.

The market doesn’t owe you anything. It won’t reciprocate if you aren’t offering any kind of value.

People who jump into action immediately after hearing an idea are more likely to fail in business.

That’s because they haven’t done the market research properly yet.

They are also very likely to commit another mistake, i.e., they will try to appeal to everyone instead of focusing on their target audience.

When you try to appeal to everybody, you don’t appeal to anybody properly.

When your product is catering to everyone, you won’t satisfy your customer today.

Your product will fail to position itself and differentiate itself from other products that are trying to target that same market.

To survive in business, your product or company must have a competitive advantage.

When you don’t have a clearly defined market, you fail to identify your competitors, and thus you also fail to identify your competitive advantages.

A general product always holds less value compared to a specialized product.

Customers are also more likely to remember a specialized product compared to a general one.

Understanding your market and customer needs gives you a clear advantage.

So don’t blindly follow advice like “do what you love” while building a business.

Otherwise, you will have to pay the “dumb tax,” if we speak in the author’s style.

Lesson #7: The only constant in business is Change.If you love safety and stability, maybe business is not for you.

If you love safety and stability, maybe business is not for you.

Business landscapes are always changing.

Most companies or business owners get complacent when they achieve a certain level of success.

They keep repeating the same strategies that worked for them in the past.

The catch is that you can’t solve new problems with old answers.

You can never stop evolving as a business owner, or your business will fade sooner or later.

The author discusses how 435 of the Fortune 500 (87%) businesses from 1955 have now disappeared as they didn’t change with the changing business environment.

Everything today is changing rapidly.

From technology to cultures, everything is changing.

It’s stupid to not change with the changing environment.

Today, customers are far smarter than they were a few years ago.

They have hundreds of options today and far less patience.

Don’t think that you are different.

Not even big companies can relax today.

If Myspace and Kodak evolved with time, they would not have experienced such big falls.

Just because one of your big ideas is working today, don’t assume that it will work after 10 years.

Set aside some time to simply think about how the business environment is changing. Think about the skills you will need to learn to keep up.

Think about how your competition is changing.

Think about what new technologies are coming to the market. These days, new technologies are rapidly changing the business environment.

Think about how your customers’ expectations and behaviors are changing with the changing environment.

Not thinking about these things will only lead you to failure.

So don’t be lazy about this.

Remember, no business on earth is bulletproof. Time is all powerful.

Shami Manohar


The Brain Behind Wizbuskout.com

I am Shami Manohar, the founder of WizBuskOut. My obsession with non-fiction books has fueled me with the energy to create this website. I read at least one book every week on topics such as business, critical thinking, mindset, psychology, and more.

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