13 Ways You Can Stop Overthinking Real Estate Investing

So, you're considering investing in real estate. It's normal to be a bit nervous about this type of investment, but you know that it is probably worth the risk because you've seen others do very well with this idea. The problem is that many real estate investors "overthink" the transaction, frequently losing the deal altogether.

  • Monday, February 3, 2020

  Matt Angerer

  Real Estate   Tips   

So, you're considering investing in real estate. It's normal to be a bit nervous about this type of investment, but you know that it is probably worth the risk because you've seen others do very well with this idea. The problem is that many real estate investors "overthink" the transaction, frequently losing the deal altogether. But we are going to share with you:

  • What "overthinking" is
  • How to become an "agent of action."
  • Sound steps to take before getting into the real estate investing arena

What Does "Overthinking" Mean?

Overthinking, also known as "analysis paralysis," can cloud your judgment and keep you from taking affirmative action. As Jocko Willink, a retired officer of the US Navy who served in the Navy SEAL teams, says on his podcast, there are individuals who instead of picking up a pencil on their desk will first ask:

  • Should I pick up this pencil?
  • Could this pencil belong to someone else?
  • If I pick it up and then drop it, will it disturb someone else?
  • Is that a #1 or a #2 lead pencil?
  • Could that pencil be a booby trap?
  • Am I supposed to be taking notes with that pencil?
  • What if someone needs this pencil, and I do not know about it?

All of this, even though the action was to pick up the pencil. Willink says that when you come across an overthinker, it is sometimes necessary to ask the person some pointed questions to keep him or her on track, such as:

  • What do you mean by that?
  • Can you explain that in a more straightforward way?
  • What's the actual goal that we are trying to accomplish?

In essence, the listener is "playing dumb" to a certain extent, and asking questions in an attempt to simplify the idea. It is almost as if the listener is beginning to become subconsciously coached into clarity. Willink says:

A lot of time when people get super-detailed is because they think what they want to do is too complicated for other people to understand. He says to make your plan adaptable. If something changes or something unexpected occurs, you can rearrange the direction, keep going and hit your target.

Why Do People Overthink?

Human beings like to have control. Humans also like certainty. Sadly, control and assurance cannot always be available to us. There is a positive side to overthinking, however. The Probability Theory requires exploration of all possible outcomes of an event to determine what might happen in any given situation. In some ways, overthinking is a form of preparation that might allow us to avoid or at least deal with whatever outcome occurs.

According to Psychological Science, intuition is more than a feeling. Many of the world's most influential people have said that they ascribe their success to having followed their intuition. A team of researchers from the University of South Wales came up with a demonstration of how much conscious intuition can inform our decisions. Joel Pearson was one of the scientists involved in the study, and he had this to say:

"These data suggest that we can use unconscious information in our body or brain to help guide us through life, to enable better decisions, faster decisions, and be more confident in the decisions we make."

How to Know if You are Overthinking

  1. You re-conjure embarrassing moments in your head, over and over again.
  2. You cannot stop worrying.
  3. You worry about things over which you have no control.
  4. You have trouble falling asleep because your mind "will not shut down."
  5. You worry about things in the past.
  6. You worry about things that could happen in the future.
  7. You often ask yourself "what if" questions.
  8. You spend time thinking about the hidden meaning of things people say or events that occur.
  9. You often replay in your mind the way someone acted or spoke.
  10. You rehash conversations in your mind that you've had with individuals and think about the things you should have said or what you wish you hadn't said.
  11. You constantly relive your mistakes.

Are There Ways to Eliminate Overthinking?

Many psychologists, writers, and businessmen and women have tossed their ideas into the ring in an attempt to come up with concrete steps that lessen the probability of overthinking. Here are a few of their thoughts:

1. Schedule Your Worry Time

Worry, anxiety, and fear can be significant problems, especially for those interested in real estate investing. Ruminating, holding back, and conjuring up the worst result can make for devastating losses in the real estate industry. Amy Morin, writing for Inc., suggests making an appointment with your fears. She says that research has found that setting aside 30 minutes each day to "worry" works. There are no instant solutions, but making a precalculated time for your worrying time has been helpful to many of her clients. Consider marking it onto your calendar or your planner. When you complete the 30 minutes, get back to work or play, and relax your mind.

2. Mental Strength Exercises

Gaining physical health and strength is something most people understand. But spiritual strengthening may be a little less familiar. There are plenty of exercises you can do to improve mental fortitude. Here are a few examples:

3. Control Your Thoughts

No, we're not talking about mind-control, we are speaking of is the practice of replacing negative thoughts with realistic thoughts. One way to do this is to encourage yourself. Think about how you talk to a good friend. Try to use kind and gentle words when you are thinking about yourself and your work. You can control your response to good and bad things and control your attitude while you're at it.

4. Get Rid of Self-Destructive Behaviors

If you are complaining, feeling sorry for yourself, being a people-pleaser, or criticizing your boss, stop that. Devote as much time possible to doing the same things mentally healthy people do.

5. Affirm Yourself

Make a habit of telling yourself you're doing a fantastic job. Remind yourself that you make excellent business choices. Give yourself a break.

6. Step Out of Your Comfort Zone

Embrace change and welcome challenges. Flexibility and courage energize a mentally healthy person and brings out the best in him or her.

7. Remember that Calculated Risks Can be Positive

With mental strength, you can weigh the risks and the benefits and assess the potential problems, or even the worst-case scenarios.

8. Never Dwell on the Past

Yes, your past experiences have an impact on the way you think. That is inevitable. But, becoming stuck in the disappointments and losses that occurred in your past is not helpful for today. Instead, invest your energy into your best present and your exciting future.

9. Try not to Make the Same Mistakes Over and Over

Some say the definition of insanity is when a person pursues the same action again, and again, and again. Take responsibility for your mistakes in the past, learn from the mistakes you made, learn how to self-reflect productively and beneficially.

10. Keep Your Power

Give no one the power of being able to take your control or making you feel inferior. Know that strength comes from your ability to manage the way you respond.

11. Support Other Individuals' Success

Even if doing so turns into one of those times that you have to "fake it 'til you make it," do not resent other peoples' success. Jealousy, resentment, and greed will bring you down. Be the person who works steadily and capably to reach your success.

12. Never Give Up

When you fail, and everyone does at one time or another, look at the failure as a chance to improve. What you learn from failure is what will bring you closer to your goals.

13. Stop Expecting Immediate Results

Mentally healthy individuals are "in it for the long haul." They do not expect immediate gratification. You need to know how to celebrate every dose of success on the way to the ultimate goal. Cultivate "staying power," because the greatest achievements most often take time to flower.


Our company provides landlords the advanced tools they need to screen renters' credit reports, criminal records, and eviction reports. Since 2011, we have been in the business of assisting real estate owners by offering landlords educational guides, and an accessible and informative blog. Contact us at Vertical Rent for information that can settle down your overthinking, help you access property management assistance, and use the wealth of knowledge we have accrued by way of 50, 000 landlords and renters we have assisted in all 50 states.

We can also help you with state-specific lease agreements, rent collection online, landlord forms, and an expansive renters' network. We are not overthinking anything. We feel secure that we can make your investment work for you. And, we know we can make your role as a landlord easier, more dependable, and rewarding. We'll be waiting to hear from you.

About the author

Matt Angerer is the Founder and President of VerticalRent. He enjoys writing on a variety of topics that help Landlords, Property Managers, and Renters across America. He is particularly interested in helping renters understand their local marketplace, pick the best places to live, and find an awesome roommate. Since 2011, VerticalRent has grown to service over 100,000 landlords and renters across America. 

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