7 Mantras to Repeat When Doubting Yourself as an Entrepreneur


Mindset is a crucial part of being a successful real estate entrepreneur. I don’t care if you only buy one house or buy tens of millions of dollars of commercial buildings — you are going to be faced with doubt at some point or another.

I doubt myself most often when I compare myself to other people. Many of my friends work the “nine to five gig” and make well over one hundred thousand dollars per year, which is obviously a ton of money. My friends work for Google, are lawyers, or work for successful tech start-ups. Can you tell that I live in the San Francisco Bay area? Their lives are very safe, and they will all likely be financially stable for the rest of their lives.

And there is absolutely nothing wrong with the way they live — but it’s just not for me.

Related: The 10 Stages of the Successful Real Estate Entrepreneur

My life is seemingly much riskier. I rely on income from tenants paying their rents on properties I own that are in different states, and I have to worry constantly about the conditions of the markets where I do flips. Sometimes I wake up at noon and go on a walk until four in the afternoon before I sit down and actually do any “work.” I love my lifestyle, but sometimes I’m riddled with a feeling of doubt about whether or not I’m actually going to make this whole thing work out long-term.

I have to tell myself that the real risk in life is not taking one. I have to tell myself that I don’t want to wake up and be sixty years old having never taken my shot at being a successful entrepreneur. Lastly, I have to tell myself the following seven things to make sure I squash my doubt and stay confident that I will make it work someway, and somehow:

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 The Top 7 Mantras to Repeat When Doubting Yourself as an Entrepreneur

7. Most of the Richest People in the World Are Entrepreneurs

My goal isn’t necessarily to be the richest person in the world, but I do want to be rich. My definition of rich is similar to the one from Rich Dad Poor Dad — you are rich if you have enough residual income to cover your expenses. You could be making $200,000 per year and not be rich by my definition if you couldn’t cover your expenses with residual income.

I don’t want to be beholden to a job where I trade hours for dollars because my hours are simply too important. I want to build up long-term investments that give me monthly income, which will free me up to do other things I’m passionate about.

6. I Don’t Want to Be Like Everyone Else

I’m a contrarian by nature; I like things other people don’t, simply because I want to be different. I have nothing against people who work day jobs, but I simply can’t be one of them. It’s hard sometimes when none of my friends want to grab a beer and watch the game on a Wednesday because they’re “tired from work.”

They tell me they wish they could live my lifestyle. It causes me to doubt whether or not I am actually being productive with my life. Then I think back to all the times I would sit at work on my computer and refresh Facebook to see the newest pictures that my friends posted. I think back to sitting at my desk doing nothing except watching the clock until it was “time to go.” What a waste of my precious time! Some might argue that a four hour walk in the middle of the day is a “waste of time,” but I couldn’t disagree more — it’s often the most productive part of my day.

5. Being an Entrepreneur Gets Harder as You Get Older

As I get older, I will undoubtedly be saddled with more responsibility — and also more to lose. The risk if I fail right now is nominal. I don’t have any kids to feed or clothe, and I have lots of good friends who would be kind enough to let me sleep on their couch! I might as well take my shot while I can afford to faces the consequences of failure.

The other thing is that I can afford to invest in projects that don’t give me a huge return right away because my expenses are low. I have done a couple of deals where I have put in a lot of time and effort, but haven’t seen a dollar for over a year. I opted for the back end potential on both deals, and it ended up working out well. For one of the deals, I had to move back into my mom’s house just so I could pay my bills. I doubt my future wife would be excited about the prospect of that scenario ten years down the line… 

4. I Can Always Get a Job if I Totally Fail

I’m a fan of asking, “What is the worst that can happen?”

As long as I don’t personally guarantee a ridiculous loan with any of my projects, then the biggest risk is that I fail and have to get a normal job. It wouldn’t be how I want to spend my life, but at least I will have taken my shot. The other option is that I could start to work part time to help pay for expenses. I know that as an entrepreneur, I have to be flexible, as well as willing to make sacrifices in order to achieve my dreams. One of the sacrifices I’m willing to make is to get a job if my investments don’t work out. 

3. You Regret the Things You Don’t Do More Than the Things You Shouldn’t Have Done

I can’t remember exactly where I read this, but I think it was from a study that surveyed a bunch of elderly people before they died and asked them what they regretted most. (It seems like a bit of a messed up thing to do, but that’s beside the point.)

The article got me thinking back to my biggest regrets. Not asking out the pretty girl who smiled at me, not taking the last shot because I was scared to miss — and not starting my own business sooner. I’m not advocating that you just go out there and do ridiculously stupid things “because you will regret it more if you don’t,” but I think it is important to have a mindset where you realize that what seems risky now really isn’t.

Related: 5 Books That Keep Me Focused As A Real Estate Entrepreneur

Ten years later, I don’t care about the girls who have rejected me; I think about the one I never asked out. I don’t remember the missed shots even close to as much as the one I didn’t take. I’m not kicking myself for the twenty stupid business ideas that I tried — I’m upset that I didn’t try them sooner! The main point here is that if you have done your homework and you believe in the idea, then you owe it to your future self to give it a shot!

2. You Only Fail When You Stop Trying

This is another quote that I read in an article. There are countless quotes to the same effect from famous inventors and athletes. It is very easily applied to real estate. I spoke with dozens of people about investing in my deals before I found someone who was willing to part with some dough. Each time, I was devastated when I got the “not for me” or simply a “no.” I had to brush it off despite the doubt that lingered in my mind.

What am I doing? Do I look stupid? Am I ever going to succeed?” All of these questions — and more — would run through my mind, but I kept coming back to the fact that I have only failed when I stop trying. I also started to realize that each pitch I gave to an investor got better and better — all of my rejections were just practice for my ultimate success. 

1. I Love Being a Real Estate Entrepreneur

Do what you love because if you love something and give it your best effort, then you are going to be great at it.

Have you ever faced doubt about your investments? What strategies do you use to cope? Am I alone in my self-doubt?

Please — share your low moments (and how you’ve conquered them) below!

About Author

Conor Flaherty

Conor has experienced every aspect of the foreclosure and rental business for single-family homes. He was VP of Acquisitions at Silver Bay Realty Trust, and has flipped over 100 homes. Conor started a blog called Wall Street Slum Lord and is working on publishing his first novel.


  1. Carlton Kohler

    Great article Conor, It’s refreshing to read a blog post like this one, especially when I need some motivation! A lot of people who watch sports get caught up in the battle between the two teams and never really appreciate the inner battles that the individual athletes have been fighting their entire lives to get them to where they are. I constantly re-read a book I bought of motivational quotes and speeches from famous football coaches and other sports figures. The real battle isn’t getting that deal or that yes from someone, it’s about finding that inner perseverance to keep on going despite your pitfalls.

  2. Great article Conor. I have been struggling with this lately. I am like you when it comes to being an employee, not for me. There are times though when those little doubts start to creep in and paralyze forward movement. At these times it is reassure to know that this is something every entrepreneur goes through. These 7 mantras are going on my “WHY” board. Thank you for the motivation and clarity.

  3. Very motivational article. I had the same questions and doubts about 2 years ago when i decided to give real estate my all, leaving nursing. It was the best decision I made.

    thank you for great article.

  4. Albert Arguelles

    Amazing article Conor!! Thank you so much for posting this! Of course we all have gone through these fears and doubts. It’s incredible how mean and insidious our own mind can be! Probably one of the hardest lessons to practice is to control our thoughts and emotions when it comes to thinking if we are doing the right thing. I definitely can relate to all the items on the list. You really hit it on the head when you say things like “comparing myself to others”. It’s always easy to think someone else looks more successful or happy or richer, etc. See?! How our minds create our reality, literally!

    But alas, we end up being the ‘heroes’ of the others who wait for the clock to hit the mark so they can go home or happy hour just to regret having to come back the next day. It’s easy to see why they would want to live this lifestyle. Yes, it’s risky and scary at times, especially in the long run and thinking of the impact we’re having in this world. But we do it because we love our freedom and because we know and want to create our own lives and for that I’m plenty proud of all of us for going after our dreams!

  5. Sandeep S.

    What a beautifully written article, Conor! I just stumbled upon it today. And being in the silicon valley, high tech world myself – I can relate to pretty much all of the points.

    I myself am a great example of proving #5 as I have been doing the 9-5 gig for 15-20 years before becoming a Real Estate entrepreneur. And given my circumstances – the bar to become successful is very high and possibility to take risks is relatively low. However it is fun being entrepreneur at any age or stage of life – I must say!

    We should catch up someday given that we are in the same area…

    And keep writing..

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