Real Estate Investing Outside Your Comfort Zone

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We all know what that “comfort zone” thing is… right?

Every one of us has spent tremendous amounts of time and energy, clawing, scratching and almost begging to stay within our comfort zones.  And to what result?  To ensure that we never get too uncomfortable or have to challenge ourselves to grow and learn and advance our real estate investing business. 

I don’t want to sound like some new age self-help guru, but staying in our “comfort zones” is not helping our business.  Got it?

I would like to share a recent discussion I had with one of my clients which got me to thinking about our “comfort” zones and how it sabotages our real estate business (mostly without our even being aware of what is happening). 

My client and I were discussing a situation where a contractor had performed shoddy work (who hasn’t dealt with this issue?) and that they needed to return to fix the issues.  When my client approached the contractor about the issue, the contractor indicated it would cost more for them to fix their poor work.  Something that this client seemed “comfortable” paying for!

Did you notice that “comfort” thing present itself?

As we discussed the situation, I recommended that my client needed to demand more from this contractor and require them to correct their poor workmanship with no addition expense to my client.  I could tell from his complete silence that my suggestion was taking him outside of his comfort zone — as he would have preferred to just pay the contractor, get the job done and move on. 

It was clear that pushing on this contractor was not something that would be easy for this client to do!

What a great learning opportunity for this client knowing that he would have to push back on this contractor, demand that they perform their work with quality and most importantly gain the confidence, by getting outside his “comfort” zone, to better and more effectively negotiate with other contractors.

Well, that is what this client did. He got outside of his comfort zone, pushed back, found that life did not end has he had known it, and is now better prepared to stretch his comfort zone yet again.

The question for each of you is this…

Do you find yourself stuck, afraid to make a decision, to stand up for your business, to take a managed risk?   In short, is your business being sabotaged by your “comfort zone”?

In preparing for this article I came up with a handful of items that may prove you are stuck in your “comfort zone”.  

Here they are…

  1. You may be stuck in your “comfort zone” if you are “uncomfortable” making low-ball offers because you don’t want to insult the seller.
  2. You may be stuck in your “comfort zone” if you are “uncomfortable” seeking out private lenders because you were never taught to ASK for money.
  3. You may be stuck in your “comfort zone” if you are “uncomfortable” negotiating directly with sellers and sabotage the negotiations by not bringing a purchase contract to the meeting.
  4. You may be stuck in your “comfort zone” if you are “uncomfortable” demanding that your contractors do their job correctly within budget and on time.
  5. You may be stuck in your “comfort zone” if you are “uncomfortable” evicting a tenant.  
  6. You may be stuck in your “comfort zone” if you are “uncomfortable” talking to banks about loans for your projects.
  7. You may be stuck in your “comfort zone” if you are “uncomfortable” saying NO to prospective tenants because they don’t qualify.
  8. You  may be stuck in your “comfort zone” if you are “uncomfortable”… YOU FILL IN THE BLANK!

I think you get the concept I am conveying in this article.  It is very simple…

The more you are willing to get outside of your “comfort zone” the sooner your business and success will accelerate.

Best of luck!


Photo: Mitch Bennett

About Author

Peter is an active and successful real estate investor in the Baltimore Maryland region for the past 8 years and is one of the founders of The Club Mastermind a real estate investing coaching program focused on local coaches helping investors to perfect their game.


  1. Peter, great advice to your client. I always put a clause in my contract with the contractor that states They incur any cost associated with correcting any work they didn’t do properly.

    I love the list you have and you hit the nail dead on. I’m very fond of point 1 and 2. If my first offer doesn’t offend then I’m too high. The private lender, that was me for a time but knowing I wanted to be successful made me start asking and I of course got out of that comfort zone.

  2. Pete,

    I’m glad you knocked some sense into that knucklehead client of yours. I think one huge tell sign of getting out of the comfort zone is procrastination. Its amazing all the little comfort tasks that get completed while putting off that important task that is clearly pushing folks outside their limits. Good topic.


    • Jason,

      I laughed hard regarding your “knucklehead’ comment.

      Your point regarding procrastination offers great insight. A great way for investors to know when they are up against the bounds of their comfort zone by delaying actions they know they need to be taking.


    • Jeff,

      Thanx for the feedback…

      I hope this article, your articles and those many great articles here on BP benefit and help everyone… but then… you can lead a horse to water (soi to speak) but you can’t make them drink!


      • Pete,
        It is true you can lead a horse to water and he may not drink. In the case of articles like this one, your leading hundreds of horses to water. A few of them are bound to lap up the advice. As always, its a numbers game. Examples also make for a good salt lick to further encourage them horses, no matter how stubborn they are sometimes.

    • Peter Giardini on

      MH… thanx for the feedback.

      The great part is that this client is now more keenly aware of when they are too comfortable and knows when they are too comfortable it is time for them to get moving.


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