Top 25 Mindsets and Habits of Successful Entrepreneurs

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October 12, 2023

It’s that time of year when we keep our eyes glued to the Top 25 college football rankings that come out every week through January. In that spirit, I came up with a list of the top 25 mindsets and habits of successful entrepreneurs. I based this list on studying and observing some of the most successful people in the world. 

1. They take long walks

Steve Jobs was famous for taking long walks with his top people. He used these for exercise, contemplation, problem-solving, and for meetings. In his book, Jobs biographer Walter Isaacson reveals: “Taking a long walk was his (Jobs’) preferred way to have a serious conversation.” Jobs believed his most creative ideas came when he was walking. He often held meetings while walking around with staff. 

2. They are curious

Curiosity is a driving force for successful people. One of the fundamental principles of the classic book by Dale Carnegie, How to Win Friends and Influence People, highlights the importance of curiosity. Carnegie argues the best way to make someone feel important is to be curious about them. Being curious is harder than it seems. The great ones can stay curious about the other person much longer than most people.

3. They write handwritten thank-you notes

They write lots of thank you notes, not just basic ones – they write genuine notes of appreciation on nice stationery. Taking the extra time to handwrite a message provides a massive return on the time invested – enhancing your professional and personal relationships. Just the other day, I received a thoughtful note from someone, and it immediately created a connection with that person.  

4. They are freedom chasers   

Dan Sullivan from Strategic Coach discusses the four freedoms – money, relationship, purpose, and time. Entrepreneurs especially have a desire to have control over their time. Check this resource out to hear more from Dan Sullivan on the four freedoms: 

5. They are coachable

No one likes a know-it-all. The best are the opposite. They crave coaching all the time. Michael Jordan’s college coach, Dean Smith, said, “Michael’s greatest attribute was his ability to be coached—a quick story – going back to the Dream Team of 1992. Mike Krzyzewski was an assistant coach on the team. Coach K explained what it was like to coach this team with Jordan. He says, “I’m sitting there, and he says, “Coach, would you please work with me? I’d like to work on some of my offensive stuff. So we worked together, and when it was over, he said thanks, Coach, and showed me incredible respect.” There is a reason why the best get coaching – it helps them stay the best.

6. They don’t hang out with average people

They surround themselves with the best people, forcing them to be better. They seek people who bring energy and avoid those who suck it. Tony Robbins goes a step further here and says you should try to hang out with people who are out of your league. I like his article on this topic:

7. They are visionaries 

Visionaries are The most successful, and they always work on a bigger future than the past. They tend not to get hung up on where they are “now,” but where they are “going.” Arnold Schwarzenneger said he refined his vision until it was very specific – win the Mr. Universe, go to Hollywood, and act in movies. He said, “I believed 100 percent that I’d achieve my goals; if you can see it and believe it, you can achieve it.” 

8. They are obsessed with learning   

The most successful entrepreneur I know is also the most obsessed learner. This man is in his late 60s, wildly successful, and beyond financially independent. To this day, he is constantly reading books, listening to podcasts, and asking other intelligent people questions. He has the attitude of a forever apprentice. When we meet, he constantly asks me questions about my business or sees if I have read any interesting books, trying to learn something he didn’t know.    

9. They are ruthless with their time.  

Just the other day, I was speaking to a billionaire entrepreneur in my industry. I asked him what his biggest key was to success. His answer was simple – “I don’t waste time.” He said four areas in his life get 100% of his attention – his family, friends, business, and faith. If an opportunity doesn’t fit into one of these, he is ruthless with saying no.

10. They trade money for time

The best don’t spend time doing things someone else can do for them. 

For example, if you calculate your time worth $500 an hour, why would you ever work below this number? I like this article on this topic written by James Clear:

11. They don’t fear failure

They are willing to take risks that most people wouldn’t. The GOAT, Michael Jordan, didn’t think about failure or bring past failures into his confidence. He once said, “Why would I worry about missing a shot that I haven’t taken yet?” This mindset was a key component of his success. 

12. They exercise frequently

Many years ago, I attended a seminar to hear a speaker who studies the most successful people in my industry. They found only one consistency among the best – they were relentless about exercise. Regular exercise has been proven to enhance your physical and mental state, positively impacting all areas of your life. There is no perfect rule of thumb here – but getting 30 minutes of exercise five days a week is a typical routine for top performers. Check this article out for more science behind exercise impacting your performance:

13. They are more disciplined 

Discipline equals Freedom – this is the formula on which Jocko Willink wrote a book. As Jocko says, “Discipline can seem like your worst enemy. But in reality, it is your best friend…most importantly, it will take you on the path to FREEDOM.”

14. They are unrealistic

Successful entrepreneurs tend to be unrealistic. The story of Roger Bannister breaking the four-minute mile comes to mind. Perhaps no one on earth thought running a mile in under four minutes was possible except for Roger Bannister. If you know the story, he broke it on May 6th, 1954, and then two months later, it was broken by another runner. I read that as of June 2022, there have been 1,755 athletes who have broken the four-minute mile. Entrepreneurs like Steve Jobs have employed a lot of unrealistic goals to drive success to levels no one thought was possible. 

15. They say no to almost everything

Warren Buffett said, “Really successful people say no to almost everything.” The most successful people have a bigger yes that drives them to make “no” their default answer on 99% of things. This excellent article goes deeper on this topic:

16. They run great meetings

Most meetings could be more exciting and productive. The best in the world run great meetings. They have a clear objective for any meeting they run and ensure that the conversation centers around that and nothing else. Their meetings lead to the right actions. Pat Lencioni, author of the book Death by Meeting, says, “Improving meetings is not just an opportunity to enhance the performance of companies. It is also a way to positively impact the lives of people.”

17. They plan their weeks on Sunday

I use The Living Your Best Year system from Darren Hardy to plan my weeks. My accountability partner and great friend, Robert Hefner V, reminded me to get back to planning my week on Sunday evenings – and I have to tell you that it has dramatically impacted my focus and productivity during the week. I recently spoke to a Billionaire, and what he told me is one of the keys to his success. You probably guessed it – he plans his week out each Sunday night. If you’re looking for a journal to start, I recommend James Clear’s version:

18. They are gritty 

Successful people don’t get deterred when things get hard. Hard times are when successful people separate themselves. Angela Duckworth, author of Grit, says that although intelligence and talent are favorable assets, grit is the ultimate predictor of success. In her book, she uses West Point as an example and explains that grit was the number one determinant when they tested the cadets who graduated from the grueling demands of West Point.

19. They block large chunks of time to do meaningful work.

I find myself fighting distraction almost on a minute-by-minute basis. The best in the world rise above everything to ensure plenty of time to tackle the most important work. The best example I know of deep work was the author of Harry Potter, J.K. Rowling, moving to a hotel for six months to finish the book’s last book. She felt that the only way she could do her best work was to get away from everything until she completed her masterpiece.

20. They vacation frequently

The most successful people take vacations frequently. They know it’s an essential element for success and wellness. Great vacations are expensive, but trips to amazing places help you recharge, broaden your horizons, and come back with your best ideas. Many successful people have told me that taking about four vacations a year, or about once every three months, is perfect. One entrepreneur told me he uses his vacation time to give his staff space to operate without him. He says that he is able to see what area of his business is weakest and then focuses his energy there until his next vacation.  

21. They take plenty of time off

This one is related to number 20 – the best in the world put so much energy into their craft or business that they need much time off. It allows them to develop some of their best ideas (because your mind is loosely wandering when you’re away from work) and renew their mind before they go all in on their next project. The fastest man ever, Usain Bolt, was reported to take off for up to two months in the offseason to allow his body plenty of time to recover before he started training and running again.

22 They know how to have fun

Fun is at the core of an entrepreneur’s success. It’s so crucial that Richard Branson teaches a masterclass titled “Never Forget the Fun.” I like his quote, “If you’re not having fun, you’re doing it wrong.”  

23. They use Mastermind Groups

In the classic book Think and Grow Rich, Napoleon Hill advocates for mastermind groups to take your personal and professional life to the next level. He describes these groups as “the coordination of knowledge and effort of two or more people, who work toward a definite purpose, in the spirit of harmony. Successful entrepreneurs have used mastermind groups for years to propel themselves much higher than they would. The type of mastermind group is not as critical as having one with like-minded people.

24. They are generous 

Wharton professor Adam Grant said, “The most meaningful way to succeed is to help others succeed. I agree. I’ve observed the most successful people to be generous. For example, let me tell you about my friend, Justin. He has been successful in many areas of life – business, government, family, and much more. Justin is also one of the most generous people I know. Whether he’s giving a $20 tip to a fast food worker or dropping what he is doing to help his friend get a job – he’s there for them. His generosity is one of the keys to his success in life.

25. They think at a higher level 

Successful entrepreneurs outthink the crowd. They often do this by scheduling regular time to think about what the competition needs to be thinking about. I like the book; 10x is easier than 2x. The author, Ben Hardy, explains that to double the size of your company, you likely will have to work twice as hard. But to go 10x, you have to think much higher since it’s impossible to work ten times as hard. Kobe Bryant summarized this concept well: “These young guys are playing checkers. I’m out there playing chess.” 

The content of this article is developed from sources believed to provide accurate information. The information is not intended as tax or legal advice. Please consult legal or tax professionals for specific information regarding your individual situation. All expressions of opinion are subject to change. This content is distributed for informational purposes only, and is not to be construed as an offer, solicitation, recommendation, or endorsement of any particular security, products or services. Past performance is not a guarantee of future results. Index performance does not reflect the expenses associated with the management of an actual portfolio.

Castlepoint Wealth Advisors | Oklahoma Wealth Advisors | Kendall King - Founder & CEO

Kendall King, CFP®, AEP®

Founder & CEO of Castlepoint Wealth Advisors

Kendall is the Founder and CEO of Castlepoint Wealth Advisors, an Independent Wealth Management firm in Oklahoma City. He is responsible for the strategic direction and vision of the firm, and serves as lead advisor to a diverse group of clients, with special focus on entrepreneurs. With more than 18 years experience in advising clients on a wide range of wealth management topics, Kendall possesses extensive expertise and specialized knowledge regarding IRA and retirement planning topics.

Read more Kendall’s Counsel blog posts and articles.