Is Fear Of Success In Real Estate Holding You Back?


I can clearly remember the first day I ever worked for someone else.  I walked through the doors to my new office, got acquainted with my surroundings, grabbed a bottle water, looked out my office and decided right then and there that I would fulfill my one year contract and then I was out of here!

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Where Our Fear of Success Hides

I had just made a life changing move halfway across the country to Denver, Colorado and left a wife and 8 month old son in Memphis, TN.  I had all the skills and knowledge to start my first business but something was holding me back.  It was my first brush with fear.  It took me years to understand what that feeling was and to admit to myself that I was actually holding back.  It took me years to realize it was not failure that I was afraid of.  I was afraid of success.  In hindsight, I can see all the decisions I was making at the time were designed to keep me comfortable and safe.  I negotiated poorly and allowed my new employer to get my services for a steal in return for a few add-ons that seemed important at the time.  I bargained away my strengths for a steady income, steady job, low expenses and low risk.  All of these necessities were never on my mind when I was considering the move but were all being looked after by my subconscious.

My own mind was holding me back from going after my dream and starting my own company.  I knew that I would not fail.  But I had yet to be “The Man”.  I had yet to hold down the spot where the buck stops!  In my subconscious I guess that was more scary than failure and my decisions put me in position to delay that day by a year.  Like I said, 15 minutes into Day 1 I knew I had made a mistake and that night I began working on my business plan.  An action I should have taken months earlier was delayed by my own fear.

Holding Back In Real Estate

Just so we are clear that a fear of success is quite common and can happen to anyone anytime they take on a new challenge, I will share one of my early endeavors into real estate.  I had been investing in real estate for over 2 years and was building a portfolio of long-term buy and hold properties in Memphis.  I was still living in Denver at the time and like many Americans, I had become addicted with the reality shows on T.V. about flipping houses.  I loved “Real Estate Pros” and “Flip That House” soon to be followed by “Flip This House” and on and on and on…

As I sat on my couch on a Saturday night watching flipping shows I decided (like a million other viewers!) that I was going to give flipping houses a shot.  I had started a sales company and built it into an $18 million yearly operation.  I was flying high with a successful company and had a great cash-flow portfolio.  I figured I had the knowledge and expertise and fear of failure was something I had never suffered from.  My next moves would prove again that it was a fear of success that would hold me back.  I picked up the phone and called a close friend of mine there in Denver and asked if he wanted to partner with me on my first house.

Related: BiggerPockets Presents: The Book on Flipping Houses

There it was.  My fear of success manifested itself in one quick emasculating phone call.  I cut my legs off before I even started.  Rather than shouldering the burden of success and taking the risks AND REWARD for myself, I invited another voice into the mix…just to make sure things went good.  I did not need a money partner.  I did not need a partner for research of MLS access or because of the extensive list of contracts he could bring to the partnership.  I needed a partner because my subconscious told me I had never done a flip before and what if I had a huge 5 figure payday?  How would I respond to that?  My subconscious told me it might be better to split that payday with someone else and then I could split the cost too!  My subconscious has a sarcastic side…

The partnership was both good and bad.  We did good deals and we did bad deals.  We made money and we lost money.  I am not sure what my partner learned during our time flipping houses, but I would bet that he learned the same thing I did.  We don’t need partners!  Both of us partnered for the exact same wrong reason – to split the risk.  Since our last flip, both of us have been successful individually because we’ve gotten rid of our fears.  No more fear of success.  Take the crutches away and get to work has pretty much been the motto since that day and I don;t think either of us has looked back…or partnered on any more deals.

What Does Fear of Success In Real Estate Look Like

Having a fear of success is very real. It can often manifests itself in ways that may make us wonder what in the world is going on.  Forgetting important facts and becoming irritated when someone else corrects you.  Stuttering in important presentations or forgetting your Bank Book when meeting with a new bank on opening an LOC.  How about entering into a partnerships instead of striking out on our own or passing on deals over minor circumstances or even choosing to stay in one area – your area of expertise – instead of growing into new opportunities. It is natural for people to be scared of the unknown and for many that is what real estate success really is.  It is an unknown.  And success brings its own set of challenges like scrutiny and criticism as well as an adjustment to growing pressure and demand to follow-up with more success.  It can be a vicious cycle that many subconsciously would rather stay away from.

Then there is the side of success that comes next.  The nagging feeling of what to do next.  The pressure to keep growing and doing bigger and better projects.  And what about the critics that almost always follow successful people?  You know the critics I am talking about.  The ones who rush to point out any mistakes you made in a project.  The critics who find it easier to point out your profit while ignoring the change you made to a neighborhood.  At some point, as you come to grips with having success, you realize that you will never make everyone happy.  Not even close.  It is much easier to deal with success by paying attention to your close circle of advisors and lean on them to find your next project, your next direction for growth and even your best critique.  They will always be more honest and open as you navigate success than someone who does not know what you have been through to get there.

Related: The [other]Four-Letter “F” Word…

The final fear that many people suffer from – especially in real estate – is the fear of becoming someone else…losing our identity.  If you don’t believe me, ask yourself what you really think of  flashy cars, fancy watches and designer shirts and walking into your local REIA like you own the place.  How many times have you watched that happen to others and then swore that you would never act that way?  The reality is that success can have that effect on you.  It can turn you into someone else…but, only if you let it.  So don’t!  Some of the wealthiest people I know have never changed their habits regardless of their success.  Have they treated themselves to a nice car or a nice vacation?  Absolutely.  Have they changed the way they dress, act or even carry themselves around town?  Mostly no.  Being successful (however you define it) does not have to change who we are so don’t be fearful.

Push Fear Aside and ‘Just Do It’

I am quickly becoming a serial entrepreneur.  I love new ideas and searching for ways to start and grow new projects.  I fail to get projects off the drawing board more than I succeed, but that is ok with me.  I need to get off start before I can know if it will work or not.  The difference between today at 40 and 10 years ago at 30 is that I no longer need the anchor of a partner or a contract or a guaranteed paycheck to get started.  Fear of success no longer follows me once I realized it was holding me back.  I urge you to get off the start box and get going with your dream.  Don’t let any fears hold you back – especially not a fear of actually growing into a successful real estate professional!

Photo: Mariano Kamp

About Author

Chris Clothier

In 2005, Chris Clothier (G+) began working with passive real estate investors and has since helped more than 1,100 investors purchase over 3,400 investment properties in Memphis, Dallas and Houston through the Memphis Invest family of companies.


  1. Awesome article! Most people are driven by fear. Almost all fear is something we make up in our own minds of what could happen. Our fears almost never come true and if they do come true try are never as bad as we think they may be.

    I am trying to be a serial entrepreneur as well. Start a business, get it running well and then let someone else take over day to day while I start something new.

    • Chris Clothier

      Mark –

      Thanks for taking the time to read the article and leave a comment!

      You are right about our fears – most are imagined and most never reach the level that we get worked up about. Especially when we fear success.

      All the best to you in each of your entrepreneurial endeavors.


  2. This is a great article and well timed for me. I think there is a difference in having a healthy dose of reality and being paralyzed by fear. I think each person needs to honestly assess their own skills and knowledge and determine what specifically they are afraid of and where they are weak.

    When I first started I made a list of the things I was afraid of. Most of those were because they were new. It ranged from calling the mortgage guy, talking to a wholesaler the first time, my first mailer, talking to my first seller, the whole closing process, using a hard money loan. I broke it down as much as I could. As those pieces of the puzzle came together I knew the next one that was coming. When it came and I got nervous about it, I recognized it and was able to move forward because I had broken a big task such as purchasing a distressed home and rehabbing it for resale into a lot of small pieces. It was still extremely terrifying but I think me recognizing up front and planning for it,helped.

    Somewhere in managing your fear you have to trust your gut as well. I haven’t figured how to filter the difference between the two. Maybe when i do, I’ll write part 2 of your blog 🙂

    • Chris Clothier

      Hey Nick –

      A lot of people are fearful of different things and we all kind of self-diagnose those fears. You may very well have a fear of failure or risk. Sometimes people think that is the case when really they are more scared of the changes that come when your risk turns into a great reward. I will tell you, that small steps lead to bigger actions. There is nothing wrong with being cautious, but never be afraid to fail. As long as your risks are not life or lifestyle threatening then stretch yourself a little at a time.

      Last piece of advice, if you don’t mind my throwing it out there, celebrate every win. I mean every win! No matter how big or how small, you have to celebrate every achievement and every win. Life is full of gut kicks and failure and we always remember those. We need to make sure we remember every win no matter how big or how small and celebrate it with a special dinner, an afternoon off or even a cold beer with a smile! All of these things are done along the way for the small victories that lead to big, big wins!

      All the best to you – Chris

      • Hey Chris,

        Thank you for the inspiration. I totally agree about celebrating wins no matter how small they are.

        As for taking risks that are not life or lifestyle threatening, I think any risk in REI is lifestyle threatening in terms of money involved. If I compare it to stocks, for example. I can by a $1000 worth of stock and 50% loss will not make a material difference for me.
        If it want to buy a rental property, I’d have to spend at least 80K and losing even 10% of that would be no fun.
        Buying it on credit is even less fun as I would be liable for the loan no matter how bad my investment performs.

        Is there any way I can take a really small position in RE? Let’s say a big investor buys an apartment complex for 100K and I add $1000 to his pool of money and get 1% of net monthly rent?


        • Chris Clothier

          Hey Nick –

          I wish I could answer your question differently, but the straight forward reply is that I don’t know for sure. Can it be done? Yes. But it would take having the right relationship with someone who simply wanted to help you out. Most investment deals simply require larger monetary buy-ins. With that being said, I have one other saying that I love – “You get 100% of what you DO NOT ask for”. So ask for it! The only way you will know is to talk to other investors and see if they ha’ve a need for a small buy-in on your part. I dont know what they will say, but I do know that they can not say Yes unless you ask.


  3. Great Article Chris, I mentioned the fear of success in one of the last articles I wrote, without going into a lot of detail. You hit the nail on the head. I see we are about the same age, something about hitting forty that changes our perspective on a lot of things, I’m sure you’d agree. Continued success Chris. I always enjoy your articles.

  4. Fantastic article! This really hit the nail on the head for me.

    I started my rental business with my little brother and unfortunately, he was randomly murdered just as the business started to take off. A year after that I spent a year trying to groom someone to take his place without any luck. A couple months ago I was walking through a complex with a potential partner and it just didn’t feel right.

    I’ve visualized myself as successful and I remember feeling greedy that I didn’t bring someone along with me.

    I’ve realized now that I’ve spent the last three years not looking for a partner, but looking for a crutch. A crutch that I don’t even need. It’s time to give it a go on my own.

    Thanks again!

    • Chris Clothier

      Eric –

      Man, I love to read comments like that about deciding to just go for it. I hate that you had to go through pain of losing your brother, but it is great to hear that you are going to go for the dream you had with him on your own. Let me know if I can help in any way.


  5. The first million’s the hardest. 🙂

    Once you find out you can make it in one area, you realize you can make it any. (she says to the serial entrepreneur)

    The fear I hear all the time is “I’m to old to try something new.” Really, is that the lie you accept to keep yourself paralyzed? I always point out that in 10 years, they’ll be 10 years older so now is the PERFECT time to try something new!

    Thanks, Chris, for your post.

    • Chris Clothier

      Hey Karen –

      Thanks for the comment.

      I do agree with you that learning what your earning potential really is – can be a process. It takes success to learn what success looks like, feels like and the road to get there. Once you know, each repetition becomes a little easier. That adage holds true with earnings as well. Making a million seems like an impossibility to some people because they have no idea how to get there and do not believe they could get there. I do know people who are scared of making money like that because of all of the “imagined pressure” that comes with it.Sometimes it is not a roadmap that is missing but a belief that one exists.

      All the best to you –


  6. Jean Bolger on

    I definitely relate to this! Yes, I am excited and optimistic about my prospects with real estate, but my fear of success is also strong and has more to do with my personal life. I don’t have any friends or relatives who have any interest in real estate AT ALL. None of them are wealthy- I pretty much run with the “struggling artist” crowd. They get that glazed look- you know the one I mean- when I mention property investing, so the subject gets dropped real fast. I’m realizing that I am in a position right now to markedly change my financial situation with the right moves; but it means becoming wealthier and more financially free than all of my friends and family. Some people (with a more competitive upbringing or nature) might find that compelling in its own right, but for me it brings up a lot of discomfort. However, I have always been self-employed so I have learned that the process of being an entrepreneur constantly brings you into learning situations and opportunities for growth — both inward and outward. I’m using all the tricks I can find to move towards my new comfort zone…

    • @Jean

      I suspect one fear you’ll have to work thru is gaining new friends and maybe some of your current friends shunning you b/c you’ll be “different” (read: not struggling anymore once you make it). but first things first… definitely stay plugged in to BP where you’ll find friends who can’t stop enough about it! haha

      much continued luck and success to you!

    • Chris Clothier

      Hey Jean –

      Thanks so much for your response. I really keyed in on one sentence you wrote. “…I have learned that the process of being an entrepreneur constantly brings you into learning situations and opportunities for growth – both in ward and out ward”.

      It reminds me that you will become the six people you surround yourself with. So as far as financial or real estate advice goes, make sure you surround yourself for those conversations with people that are successful and full of support and energy for your endeavors. The same goes for wealth creation. It is very difficult to learn the lessons of wealth creation by being constantly surrounded with messages that are contrary to what you want to do.

      All I can tell you is that countless thousands of other people have been in the same position. Some have failed and some have succeeded. It really depends on how committed you are to YOUR success first.

      Please don’t hesitate to reach out to me if I can help – even for a talk over the phone.


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