5 Major Business Regrets Too Many CEOs Have

8 min read
Aug 7, 2022

Live life with no regrets?

It sounds nice on a surface level, but it is not reality for most people, including business owners.

In reality, most CEOs look back on their journey and wish they would have done some things differently.

Some beat themselves up for it, while others accept it as is.  Either way, you do not want that to be you one day.

To help you achieve greater business and life success, I am sharing five significant regrets most business owners carry with them.

More importantly, I am sharing how you can avoid making particular mistakes to prevent feeling the same regrets.

Not every mistake is a regret. But every regret comes from a mistake.

Here are five regrets to avoid if you have high hopes of business and life success.


1. Taking Their Time


Time is money.

I am not a fan of most cliché one-liners.

However, this could not be more true.

Time really is money!

While you can make more friends and money, you can never replace lost time.

Unfortunately, most people do not embrace this reality until it is too late.

Most people have a take-your-time mindset.

They wait for the supposedly right circumstances or time to come before getting started on a new business project or setting a new set of goals.

Instead of taking immediate action on what they know they need to do, they take their jolly old time.

Eventually, they realize that taking their time morphed into taking forever.  AKA, they never take action at all and regret it forever.

That said, you will never regret taking action today.

The best day to start was yesterday, the second best is today!


You Do Not Have All the Time in the World

I do not know who needs to hear this, but you DO NOT have all the time in the world.

A hard truth about life that most of us do not like to face is that we do not know how much time we have left.

It could be a little or a lot, but you never want to take chances and automatically assume a lot.

About twenty years ago, my dad died on the eve of his retirement.

Nobody could have predicted it would happen, but it did.

I say this not to scare you but to increase your sense of urgency.

Whatever you want to do must be done today!

Every day (and even every hour) is a day you will not get back.

Therefore, start immediately!


You Can Run Without Rushing

But Brian, I do not want to rush things before I am ready!

Here is the thing: You must take action immediately, but that does not mean you need to rush.

Running a business is a marathon, not a sprint.

Sure, there will be times you need to pick up the pace, but that does not mean you need to rush.

Also, you will never be 100% ready to take action.

You can always do something else to try and improve your circumstances before starting.

Therefore, you have to take action before you think you are ready.

So what if you do not feel 100% prepared?

You will never feel totally ready, so you might as well start today.


2. Not Maxing Out Their Effort


Regular gym-goers and weightlifters are familiar with the idea of maxing themselves out: Maxing out is about pushing yourself to the absolute limit.

It is about pushing yourself to the peak of your abilities until you almost feel you are going to crack.

For example, weightlifters will add their maximum weight load to a barbell to perform five reps of an exercise; during those five reps, their muscles quiver but they still get it done.

That said, you need to max out the effort you put into business goals!

No business owner looks back on life and says, ‘I wish I would have pushed myself less’.

Instead, they reflect on life and say, ‘I wish I would have pushed myself more!’.

You will never reach the highest levels of success without maxing out.


If You Are Not Sore, Then You Are Not Trying Hard Enough

The purpose of having business goals is to push yourself to your limits.

The goals are not challenging enough if they do not force you out of your comfort zone (and maybe even make you sweat a little).

That said, ask yourself if your current business goals are making you sore and sweaty.

If not, the goals are totally worthless.

Each new set of coals you create should help you reach a higher level of success.  

However, you cannot reach a higher level without pushing yourself to the limit.

A weightlifter does not increase their max load by continuously decreasing the difficulty of their weight load.

Instead, they increase their max load capacity by slowly adding additional weight every day.

Furthermore, your goals will never make you a better business owner unless they make you sore.


You Can Almost Always Go One Level Higher

Here is the thing: You can almost always push yourself more than you already are.

You can almost always make one additional cold call or run one more mile.

That said, stop telling yourself that you have reached your limit when you know darn well you can do more!

Only stop when you can honestly say to yourself, ‘I have done everything I can to have a successful day/win this client/etc’.

You can either make excuses or improve- there is no in-between.

The next time you feel you are hitting maximum effort, ask yourself if you can push a tad bit more!

Over time, the little extra pushes will accumulate to make the grandest difference.


3. Letting Other People Control Them


Most CEOs start a business to, at least in part, control their time, energy, and money.

Ironically, many business owners start their business only to let other people control them!

It is as if they completely forgot why they are doing this in the first place.

For example, business owners let their friends, family, team members, and even customers' opinions determine the actions they take.

Consider this: You do not have all the answers and never will.  

However, neither do other people.

It is one thing to humble yourself and learn from others, but to let somebody else control you because you depend on their opinions is nonsense.

Nobody looks back on life thinking, ‘I wish I would have let so-and-so take control of my business for me’.

Instead, they think, ‘I wish I would have taken ownership of my life and business according to my terms.


You Will Make Mistakes, But They Are Your Mistakes

You will make mistakes during your business journey, and there is nothing wrong with that.

In many cases, mistakes lead to massive business breakthroughs.

That is, as long as the mistake was YOUR mistake!

I mean, as long as the mistake came as a consequence of your decision instead of a decision that you let somebody else make for you.

It is one thing to mess up on your own terms and another thing to mess up on somebody else’s terms.

Stop letting other people make decisions for you; it will make you bitter and unlikely to make anything positive of mistakes.


Nobody Will Ever Understand the Depth of Your Vision

Every business owner is on a mission to manifest a vision.

Also known as the ultimate destination or desired outcome, the vision is the end result you are trying to create through your business.

For example, your vision might be creating the next major SAAS company or solving the dilemma of world hunger.

That destination or vision is deeply personal to business owners; nobody understands it as they do.

Therefore, letting somebody else control you is a recipe for disaster.

They might understand your surface-level goals, however, they will never completely grasp the ultimate destination you are trying to reach.

The last thing you want to do in life is look back and realize you sacrificed your vision to please other people!


4. Never Stopping to Smell the Roses


Grinding is a concept invented by social media business gurus; it is the idea of putting your head down and working like a mad person while ignoring everything around you.

Hard work while pushing through challenging circumstances?  

Yes, please!

Hard work while ignoring your challenging circumstances?  

Please no!

Business owners grind to ignore encroaching problems.

They use grinding as an method to not face the music.

If working hard requires you to put your head down and ignore the problems of your life, then you have an even bigger problem. 

Nobody says, ‘I am glad I ignored my problems forever!’.

Instead, business owners say, ‘I wish I would have faced the music sooner’.

From now on, work hard without grinding.


You Cannot Outrun Your Problems.

The more you ignore your problems, the worse they get.

Think of it like this: Confronting credit card debt is challenging, but throwing statements in the trash will not help you.  Even if you work hard putting together monthly budgets, the budgets will not solve the encroaching problem.

Similarly, confronting business problems is challenging.

However, ignoring them for the sake of grinding does not help in the least bit!

Over time, those problems will get worse and worse.

Suddenly, you are dealing with a serious problem instead of a manageable one.

That said, you cannot outrun your problems!

Be strong, face them, and work through them, but DO NOT ignore them.


What Is the Point if You Do not Stop & Smell the Roses?

Not only is grinding a method people use to avoid facing problems, but it also cuts them off from the joys of running a business.

Think of it like this: How can you stop and appreciate what you have accomplished if you grind 24/7?

It is impossible to appreciate the view if you never stop climbing the mountain for even one second.

Successful business owners learn to stop every once in a while, look back on their journey, and appreciate the challenges they have experienced.  

Instead of being bitter about the roadblocks, they look back on them and smile.

Not only that, but looking back at how far they have come gives them even more fuel to push forward.

That said, you will regret not soaking up the experience of climbing the mountain.

Even more, you will reflect on the experience and be thankful for everything that got you to that point.

How will you have joy in the journey if you never stop to smell the roses?


5. Not Being More Assertive for What They Want


To put it simply- nobody looks back on life and says, ‘I wish I was not so assertive for what I wanted!

Instead, they say, ‘I wish I stood up and advocated more for what I wanted’.

Moreover, most CEOs regret not asserting themselves to get what they want.

CEOs most commonly regret not being assertive when it comes to business growth.

They wish they would have been more assertive with potential customers to increase sales and grow their business.

Sound familiar?

Not being assertive or fighting hard enough is most CEO’s biggest regret because it has the broadest implications.

Without assertiveness, you cannot grow your business, manage a team, or even speak to a potential customer without being run over.

You can have all your ducks in a row and still fail if you are not assertive.


Nobody Will Save You

Nobody is going to advocate for you.

If you want something, you must be willing to fight for it.

Most CEOs who are not assertive are not because they do not want people to think they are overbearing or desperate.

Moreover, most CEOs who are not assertive are that way because they care about what other people think of them.

Is there any time in life in which basing decisions on what other people may or may not think is beneficial?

Probably not.

That said, why is it okay in this situation?


News Flash: Nobody Is Even Thinking About You

The bad news for CEOs who care about what other people think is that nobody thinks about them in the first place.

If you are a business owner who holds back because of what other people might think, remind yourself that nobody is even thinking about you!

Do you really think your customers, team members, and friends lay their heads on the pillow at night and think about how you act?


Instead, they lay their head down and think about their own problems.

Therefore, there is no point in not being assertive because of what other people think.

Constantly remind yourself that nobody is thinking about you, so you might as well do what you want to do.


Final Thoughts on the Biggest Regrets Too Many Business Owners Have


Again, it is one thing to look back and see mistakes and another to look back and feel regretful.

Learn from other CEO’s regrets before they become your regrets, too.

Not only will you live a life with fewer ‘I wish I would haves’ and ‘I wish I wouldn’t haves’, but you will also be more successful in business and life than ever.

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