5 Questions to Ask About the Five People Closest to You

by | BiggerPockets.com

“You are the average of the five people you spend the most time with.” Jim Rohn

This is probably one of the most hardcore truths about success. It’s definitely not shiny and happy; it’s definitely not an aspect that is widely discussed when it comes to the public perception of success. Warren Buffett went so far as to say:

“It’s better to hang out with people better than you. Pick out associates whose behavior is better than yours and you’ll drift in that direction.”

Consider the following questions about the five people who have made a huge impact in your life in that last six months.

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Who is Supportive About my Goals?

Real estate investing can be daunting.

Depending on which one of the hundred plus ways to win the game it can be down right mind boggling. For example, the complexities of buying and holding a single family residential property are mild in comparison to a ground up development of a 160 unit apartment building for which you raised private equity.

Whichever it is for you, I can attest my fan section has been invaluable sorting through all the resistance that comes with achievement. If it were easy, it would not be lucrative. Having that baseline to power through setbacks has served me well.

Who is the Most Negative?

It is nice to have effective criticism to use to improve. However if your “friends” makes Eeyore look like Tony Robbins then its time for a change. I can assure you from my experience you wont regret firing these people from your life.

Does My Circle of Influence Pull Me the Right Way?

Humans are the smartest of the pack animals. However, remember Enron? Did Andy Fastow’s group serve the investors and the employee’s well? Business decisions are interesting in this regard, from an ethics stand point. If you see your CEO taking a position and or actions that are clearly unethical do you call him out?

Social and economic pressure make it less certain you will.  Perhaps why a great pack to run with are crucial? The right pack will propel you to excellence – not test your ethics.

Do I Need a Mentor or Coach?

Success is certain if we model others that have our result that we want right? Is it possible to fail if we apply the minimum keys to success?

Sure, certain people appear gifted and traveling to the moon is a tad different. Real estate investment role models are abundant, and reading is a great way to start to develop the road map to what we want. In my mind – the genius of BiggerPockets also revels itself in this regard.

My debate coach in college was a tremendous mentor for my legal career…having someone you can ask all the questions about the hurdles worked for me. Regardless of source (person, biography…) it seems mentorship is key to accelerate results.

Do I Have Running Mates?

Having the Napoleon Hill-style mastermind group that was laid out so powerfully in Think and Grow Rich has been another momentous change. Imagine having a few close confidants that understand the goal, understand the resistance, and are working in league to create wins.

Overall, the answers to these five questions have impacted me at various times throughout my professional life. It’s nice to actually understand the frame-work more formally and to be able to use it intentionally.

What do you think? Have you had similar experiences?
Photo Credit: Neal.

About Author

Douglas Dowell

Douglas Dowell J.D. is a commercial and multifamily investor. His blog will focus on legally raising private money, risk mitigation with due diligence and management science. He is also an avid student of success principles with a focus on modeling success factors.


  1. Great read Douglas!! I think you follow these rules its half the battle. Two of my favorite quotes are if you are the smartest person in the room you are in the wrong room and if you hang out with four broke people your the fifth. To me your article is dead on!

  2. Priscila Argaez on

    Great article Douglas! I think it is crucial to surround yourself with the right people. It’s definitely not an easy task given that most people live an average, if not mediocre, life. I personally like to surround myself with like-minded people, and people that are more successful than I am. It provides me not only with more opportunities, but also with a different perspective on things. I remember when I moved to the U.S. a couple of years ago. I didn’t know the language and was eager to learn it right away. First thing I did was to hang out with people who spoke English (and not with my Spanish-speaking friends) so that way I would pick up the language immediately. It is so true that one becomes the product of the people one spends the most time with. I definitely try to keep a close eye on my friendships and on the people I associate with.

    Love the idea of a mastermind group for more advanced investors and a mentor for young/new investors (a true mentor, and not just a guru trying to take as much money from you by giving you little to no value.)

  3. Thanks Douglas,

    This article is a great reminder for all of us. It can feel vulnerable and risky initiating connections with people who have way more skill and experience than we do. I liked what Seth Godin says in his blog today “all that insulation from what the real world requires is getting quite expensive. It’s easy to pretend that indulging in the avoidance of the feeling of risk is free and unavoidable. It’s neither.”

    Let’s all go big this year!

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