For Newbies: The Motivation You Need to Take Off the Training Wheels (& Start Down the Road to Investing Success!)


Do you remember the first time you rode a bike?

I’m not talking the fun, easy, cute bike with the training wheels and tassels. Not the one you posed on for the Christmas picture and sat on while you played make believe you were going really fast.

I mean the bike where you took the training wheels off. You know, when stuff got real. The moment when all the innocent, harmless fun you’d been having is forced out of the way for big boy/big girl type stuff. When the safe, harmless bike was about to turn into a real bike. When you had to face the reality that you could actually fall. That crossroad transitional phase where in order to take the next step in your childhood, you had to accept the fact that pain was now a very real part of this bike riding process, and there was no way you could avoid it.

If you were like me, you resisted. You tried to convince mom and dad that it was best to keep the training wheels on. Maybe you even begged, pleaded, or cried (I will not admit I resorted to this — purely hypothetical). You see, this was such an important moment because for one of the first times in your little life, fear was being forced to mix with your fun.

Before this, you got all the joys of riding a bike without any of the risk. You could pedal up and down the street, turn circles, play with your friends, all without the risk of actually falling. Unfortunately, you couldn’t go that fast. The training wheels slowed you down. You also couldn’t turn as sharply. The training wheels limited your ability to maneuver quickly and make sharp decisions. If you wanted to get the full experience of riding a bike, you needed to be unencumbered by the training wheels.

It was just so dang terrifying!

Maybe at this point, you questioned whether or not you really wanted to continue riding a bike. Maybe you looked at alternatives. Roller skates aren’t that bad; they seem kind of fun. Lots of kids are still riding tricycles these days, right? You can be the one to keep that trend going, maybe start a trike gang and roll deep with your three-wheeled friends so no one could make fun of you without paying the price. Or what about skateboards? In a few years, you could get one of those. By then you wouldn’t be scared of falling because you’d be that much bigger. Yeah, that’s a great plan. Let’s put off facing this scary reality and just wait until it’s not scary anymore, then tackle it.


Related: How to Use a Fear of Failure to Empower Action (in 4 Simple Steps!)

None of us have ever done that, right?

I know I can’t be the only one. Man, I was scared. I did not want to risk falling and getting hurt. I did not believe I was ready. My little brain was already looking for crazy alternatives to help me justify quitting. Anything to keep me from having to learn to ride a bike with no training wheels. Lucky for me, I had parents who wouldn’t let me quit. In a semi-traumatizing sequence, my dad put me out there, promised not to let go — then let go the minute two seconds after I started.

I panicked, crashed, and was pissed.

As I fought back the hot tears of betrayal, he made me get back up and do it again. And again, and again, and again. Eventually, in a few hours, I could ride a bike. Then, like every other kid with amazing short-term memory, I forgot all about how scary it was and fell in love with this new, fast, amazing bike. I wanted to ride every day, to tell everyone I knew about my new skills, to share this cool experience with everyone else. All I told my friends about was how badly they needed to ditch those training wheels and move on to big boy status. Like I, the fearless one, had already done.

Does this process sound familiar? You learn about a new thing. The thing is cool. You soak up all the info you can about said new thing. You’re not actually doing it yet, but sometimes it feels like you are as you imagine it, plan for it, pretend like you are. You pick up the lingo of the thing and soak up the culture.

If you’re reading this post, that new thing is probably real estate investing.

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For Those Newbies Who Haven’t Made it Happen — Yet

You read the articles. You work the spreadsheets. You play with the site calculators. You discuss or read discussions about strategy on the forums. You watch House Hunters International and Fixer Upper on HGTV (Chip and Joanna are just SO cute, and you feel like you practically know them). You listen to the podcasts, you’ve read Rich Dad Poor Dad, and you’ve written out all your goals on your dream sheet. You are ABOUT THIS LIFE. And it’s gonna happen — it’s just a matter of time.

The only problem is, you haven’t made it happen yet.

Now, that’s OK. If you’re not ready, you’re not ready. I’m not here to tell you to “get ready.” That’s a long process. What I want to talk about here is how right now, in your current state, you are riding this real estate bike with training wheels. You are getting to be a part of the experience by following along with others, but you don’t have any of the risk yet. This is a healthy and natural phase; this is the phase where the desire is born. You need that desire in order to push through the hard times. Keep growing it! But deep inside, you also know when you actually make that first move, you will be exposed to risk. You will face potential pain. You could be embarrassed, exposed, or financially injured. It won’t be pure fun with no fear. You could fall off that bike and get hurt.

Maybe you’ve been in the training wheels phase for a while now and are having a great time. You keep subconsciously putting off making that first purchase because you’re “not ready.” You say you need to read more articles, follow more gurus, read more books, crunch more numbers, save more money, etc. Truth is, you are like me looking for any reason you can to keep those training wheels on. You are feeling fear threatening to take the place of what so far has been only fun. And because of this, you have a million reasons to avoid jumping in and getting on that bike.

Hey, I’m not here to judge. I know the feeling. I just admitted (hypothetically) that I was ready to start a tricycle gang, for crying out loud, all to avoid having to learn to ride a bike with no training wheels. I didn’t like that fear, either. Do you know why I didn’t stay in that phase? My dad wouldn’t let me. That’s it.

My dad wanted better for me and knew how much fun I’d have should I learn how to ride a real bike. The sterilized version of it I had experienced so far would pale in comparison to the joys of the real thing. I thought I was trying to be safe, but really I was missing out on all the perks and benefits that come from riding a real bike. By avoiding the temporary pain of a few falls while learning, I was going to miss out on the permanent benefits (as well as possibly ending up in prison, the only logical conclusion to my tricycle gang solution) of being a bike riding big boy.


Do You Have a “Dad” to Remove Your Real Estate Training Wheels?

My dad’s not around anymore, but I can still hear his voice and remember the things he taught me. Having learned what I learned, I know it didn’t make sense to keep the training wheels on, only to miss the opportunity to grow as well as all the perks that came from growth. If I didn’t have a dad back then, truth is, maybe I never would have learned to ride a bike. Sad, right? But what if that’s the same situation you find yourself in with this real estate thing?

If you want to conquer your goals, you first need to conquer own self. If you want to do that, you need to understand your enemy-Namely, what’s going on in  your own head. Most of us know what our conscious thoughts are. Very few of us are aware of what’s happening subconsciously.  Believe it or not, the subconscious is way bigger and more powerful than the conscious. If you’re not living the life you’d like or having the results you want, you need look no further than the subconscious.

Related: 6 Empowering Strategies to Conquer a Paralyzing Fear of Failure

If you find yourself surrounding yourself with real estate investing but not getting involved, you’re basically watching all the other kids ride bikes while you sit watching on the sidewalk, balanced on your training wheels. Yes, it’s fun, but c’mon. It doesn’t compare. Thirty years from now, you won’t look back and be glad all you did was read articles and talk real estate. You’ll wish you had jumped in, bought something, and had a fully paid off property by now. That’s why I’m writing this article. I want you to have that. I want you to understand the reasons you aren’t jumping in are not what you think they are.

Brandon Turner wrote a book on investing in real estate with no and low money down. TONS of blog posts are written about how to get started. In fact, I would say the majority of the content on this site is directed towards the majority of the users — NEWBIES. Why are there so many newbies and not more participants? Why with all this amazing content, are people not putting it to use? Because of the power of the subconscious.

This does not apply to everyone. Some of you are making things happen. I commend you. However, even those of us making moves are still very influenced by our subconscious. None more than me. I wrestle with mine daily. That’s why I’m so aware of this. But think, if you’re not wrestling with yours, do you think that’s because it’s not a problem? Or do you think maybe it’s because you’re avoiding dealing with it, and giving it all the power and control over the moves you make with your life? Sure, you consciously choose to log in to BiggerPockets and read articles like this — if that’s all you let yourself acknowledge, you’re fooling yourself. What are you doing with what you read? What is holding you back from putting yourself in a position to succeed? I’ll tell you, more often than not, it’s your subconscious fears. And they are powerful.

We all have them — none more than me. They guide my steps and put limits and barriers on what I can achieve. I read BiggerPockets for FIVE YEARS and never once tried to get involved in the community here. Why’s that? Because I believed I had nothing to offer. I didn’t consciously think this — I knew that I knew some stuff. Subconsciously, I just couldn’t see myself being one of the influential people. I didn’t want to take off the training wheels. So I sat on the sidelines and let my subconscious fears dictate my steps, and consequently, the direction of my entire life.


Is It Worth the Struggle?

Now, this article isn’t about me. I’m saying this so you can believe I understand the struggle. I also know you probably don’t have someone forcing you to take the training wheels off, so maybe you never will. That bothers me. I don’t want to see that. One of you might bring me my next deal. It never would have happened if you wouldn’t have woke up that champion inside. Why should the hedge funds get all the best stuff? We need more troops on the ground out there working their spheres of influence and finding opportunities.

If you are having a hard time making your first purchase, or second, or getting that license, or learning a new asset class, or whatever, it is more than likely because you are afraid the fear will begin to mix with what has been safe fun. The thing is, just like learning to ride a bike, you won’t keep crashing forever. In fact, we say “it’s like learning to ride a bike” when describing something that you’ll never forget. Real estate investing, like everything else, has its growing pains, but take it from me — it doesn’t stay so scary forever.

Sometimes I make deals without thinking about them for much after I hang up the phone with the agent. I buy houses I’ve never even seen and keep them for years. I do some scary stuff. I put a lot of effort into developing a system, then I let that system carry me with minimal effort. At this point, what once was very scary is not scary at all. I took some falls, learned to ride, and now I’m pushing myself to race. I want to see how fast I can get this bike to go. To see how quickly I can change directions and move to new markets, to see how fast I can pedal and buy more properties. Get them rent ready faster. Refinance them more quickly.

Why should it be only me? Probably because no one is pushing  you. No one is making you take off those training wheels and get out there and learn. You want someone to hold your hand the whole way through. I get that. I did too. Guess what? My dad didn’t. He couldn’t run alongside me the entire time. Had to let go and let me figure it out. That’s OK. You don’t need someone there the entire time, it’s not rocket science and you’ve got Bigger Pockets! Bigger Pockets won’t let go after two seconds and send you to your doom after promising not to! You can totally make this happen.

The truth is, your fears about what could go wrong are rarely emotionally in line with the realities of your situation. Nearly every situation you could encounter someone has already encountered and has the answer for. You can learn from them. Your fear is not worth keeping. It’s not worth the fun and benefits you’re missing out on by not taking off the training wheels and jumping in. Trust me, making six figure on a deal is fun. It’s worth taking a few scrapes and bruises for. Those will heal. You can make those six figures last forever. Grow to seven figures. Change your life.


That Scary “Dragon” Might Just Be a Lizard

If you’re reading this, please understand there is a reason for everything that happens. There is a reason you feel the way you do, and there is a reason taking that first step is just so dang scary. It doesn’t mean the reason is worthy of the power you give it. It doesn’t mean it’s a good reason. Deep in your subconscious, a lot is going on. It’s not always positive, especially if you’re not aware of it. Don’t let that dragon you’ve allowed to grow in your subconscious stay there. In reality, it’s more like the Geico lizard. You just need to shine light on it and realize how it became so powerful. There is no reason to allow it to be so. That’s not your dragon’s space. That’s your dream’s space.

Related: How Top Entrepreneurs Overcome the Dreaded Fear of Failure

I’m taking this journey myself. Testing the things I believe about myself and wondering how accurate it all is. I know I can’t be the only one. If you are faithfully researching BiggerPockets, c’mon, let’s be honest here — you love real estate and you want to succeed in it. If your conscious mind is working this hard to fill your head with knowledge, don’t let your sub-conscious mind have the final say on which direction your life goes. Take ownership of that beast, wrestle it until it’s under your feet, and let your true desires, talents, and abilities come to the surface and serve your life the way you want them to.

Remember, if you’re feeling anxiety, worry, a lack of confidence, etc. and you are doing everything in your power to be prepared, it might be that the fun you’ve been experiencing is being threatened by the fear of what could go wrong. Don’t let that happen. Don’t let fear win. Too much is talked about knowledge regarding real estate investing. Knowledge is great; this site has so much knowledge. Knowledge is not what is holding most people back. Subconscious fear is. And there is no reason for that. It’s your life. Take control of it. Make your subconscious serve you, not the other way around.

We all have that big, scary Wizard of Oz lurking in the recesses of our mind giving us all the reasons we shouldn’t move forward. Sometimes taking a peek behind the curtain to see what’s actually there can reveal a perspective you really need.

Subconscious fear holds people back. Cut the ties and watch yourself soar.

If you’ve overcome a fear of action, how did you learn to jump into investing? If you’re a newbie yet to land that first deal, how are you tackling your anxieties?

Leave your comments below!

About Author

David Greene

David is a real estate investor/agent/author/entrepreneur/police officer in the CA SF Bay Area. David's goal is to achieve total financial independence through real estate and to help as many others do so as possible. When not hunting bad guys, he hunts deals and loves talking real estate. To learn more about David, visit his website where you can also sign into his free investor's newsletter and follow along as he walks you through his deals and shares his latest projects.


  1. Jerry W.

    Nice article. I also like your day job. I am a prosecutor. I do real estate and hope to change to full time real estate some day, but for now it is my weekend and evening job. Thanks for taking the time to share your thoughts.

  2. mary hasnon

    It’s been 3 months since I started my education, and I have been petrified! I attended my first network meeting on Tuesday. It rejuvenated me. I still have some fear, but in order to move forward, I MUST take the leap! Thanks for the encouragement!

  3. Michael Parsons

    Great observations, David!
    I was the kid that, sans Dad, asked Grandpa for the wrench so I could take the training wheels off, all by myself, right NOW! Been making Mom worry for 40+ years since then 🙂
    Later, when my own kids asked where I went every morning, I told them I was “going to slay dragons”.
    It’s time to slay new dragons in this strange, new wold called ‘Real Estate’. And yes, I’ll share the journey there, and back again, in my own ‘Black Book of Southmarch’.

  4. Great Article! I thoroughly enjoyed it!

    As a new investor that is looking for my first deal I can totally relate to the overall sentiment of this post.

    Coming from an entrepreneurial background and then transitioning into real estate, the very first thing that I came to realize was that I needed to get my first deal out of the way, be it a success or failure, I just have to gain that experience of actually doing a deal, and that will be the platform, the foundation, to build the rest of my real estate career off of.

    If you never take the leap, then you can’t get to the other side.

    So fail quick. Fail hard. And Fail Forward.

    Learn, adjust your course, and modify your action steps, slay the subconscious devil, and you will meet success!

  5. Thank you for the encouraging yet funny article. I used to just read, now I’m actually commenting. Hopefully, next time I will be writing about my REI experience… (crossing my fingers).

  6. Keith Marcion on

    Great post David. I think not only fear but procrastination is another powerful factor and I think I fall into this category. Many of us, like you said have the basic knowledge from reading RE topics and having many books on RE. There is a more concerted effort placed on buying RE books and going to seminars than pulling the trigger.

    After reading this article my next step is to date when I can get financing in order and I will post when this done.

    Thanks again David

  7. Liana Alexander

    One of the biggest roadblocks my clients have discussed is having the funds to jump in with both feet. It’s scary without having a nest-egg or safety net. Thankfully having an extra $50k-$250k (and at 0$ interest) gives most people the motivation and means to start a new business venture or take their existing business to the next level.

  8. Tapanga Matthews

    This was such a great post. My dad did help me learn to ride a little. but the biggest cheering team I had was the kids on my block who all held on to the back of my bicycle and ran down the block with me until they saw fit to let go. I ABSOLUTELY fell and still have the scar 25 years later. But it didn’t hurt as much because the kids on the block helped me up and showed me how to do it again until I figured it out (that was a great summer). Just like the investors and other newbies on BP that answer questions, post on forums and are an active part of this community. Persistence and the right support system are necessary for any newbie to feel confident.
    My wheels will be off soon.

    thank you BP

    Best regards

    T. Matthews

  9. Lisa Bryant

    David, David! What a great article and insight to be a newbie. That, I am! Now, I am going through the stage of- the I am ready to make some MONEY! My process is productive. Sending out direct mailers, research on properties, making connections to cash buyers, and working on building a team for the business. However, there seems to be something else…to my next step. Searching. Thank you, for your (raw) article and caring for others in the business. Can I inbox you?

    Learn, Apply, Produce!


  10. Julie Zaytsev

    David, I bought a condo in my twenties and suffered a large loss. For a number of years, that loss paralyzed me and (I’m not proud to say) that I used it as an excuse to remain stagnant in my business aspirations. I am currently working on a plan to get back into investing and really appreciated your analogies! Thanks!

  11. Darnell Griggs

    Great article, Can relate to the article with ease. Was never afraid to take off the training wheels. The first ride had some success. Had to fun til I hit a parked car. Hurt for a little bit but got back on and continued. Going to take that experience and use it towards real estate investing.

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