Why You Should Never Take a Break as a Real Estate Investor

Why You Should Never Take a Break as a Real Estate Investor

Jonathan GreeneBusiness Member
Real Estate Consultant · Madison, NJ · Member since 2016 · 6k+ posts · 7k+ votes

Taking action isn't only investing in real estate. You should take a break from buying if the deals don't match your buy box, you are out of money, or for several other reasons (partner isn't on board, over-leveraged on different properties, acting out of FOMO, etc.). Still, you should never take a break from looking, touring, vetting, and analyzing. You can't take six months off from reviewing properties and hop back in like nothing happened. Stuff happened.

If I were to sum up the one thing that I think investors aren't doing enough, it would be getting real-life reps. Real-life reps, to me, means seeing properties in person, whatever your asset class. What you see on the spreadsheet is a small part of every story. Boots on the ground, or lack thereof, are where the mistakes are made. Of course, the smaller the property, the more necessary that you see every inch of it because there isn't a business running on top of the land like large-scale multifamily, self-storage, industrial, and more. But even if you want to do large deals, you need comparable reps.

Technology has made it easy to "analyze" deals. Still, if you aren't whittling down the number you are analyzing financially to a small subset you see before deciding what to do, you are missing an essential part of getting to the tipping point of expertise in your field. The most successful investors have looked at thousands of properties in person in their lifetimes. So, even when the market is challenging, you can still see properties and stay current.

Don't take a break when the rates are high. Don't take a break when the weather is terrible. Don't take a break when others are taking a break. Removing all skills from the equation, if you don't take a break from participating as a real estate investor in some way each day, you will stay far ahead of everyone else who keeps subbing themselves out and then asking to get back in when the game is already out of reach.

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Shawn AckermanPro Member
Real Estate Entrepreneur · Mid West, East Coast · Member since 2015 · 3k+ posts · 1k+ votes
1y

Great advice man!!!! I took a long break and I'm paying for it now LOL!! Expenses do not take a break so until you have no expenses taking breaks should be quick and infrequent.  Better yet train others to keep things going while you take your break.

Again Jonathan thanks for the reminder that the grind never stops.  Addicted to the process not the end result!

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  • Investor · Hendersonville, NC · Member since 2016 · 498 posts · 285 votes
    1y

    Hear hear @Jonathan Greene!

    And I'd like to add that if you have taken a break, now is a great time to get some reps in. 

  • Shawn AckermanPro Member
    Real Estate Entrepreneur · Mid West, East Coast · Member since 2015 · 3k+ posts · 1k+ votes
    1y

    Great advice man!!!! I took a long break and I'm paying for it now LOL!! Expenses do not take a break so until you have no expenses taking breaks should be quick and infrequent.  Better yet train others to keep things going while you take your break.

    Again Jonathan thanks for the reminder that the grind never stops.  Addicted to the process not the end result!

  • Jonathan GreeneBusiness Member
    OP
    Real Estate Consultant · Madison, NJ · Member since 2016 · 6k+ posts · 7k+ votes
    1y
    Quote from @Dominic Mazzarella:

    Hear hear @Jonathan Greene!

    And I'd like to add that if you have taken a break, now is a great time to get some reps in. 


    That's a great point. Even if you've taken a break and feel lost, the first step is to get to a meetup asap or just go to an Open House or view a property with your agent. Now, go do it. Thanks for that add.

  • Jonathan GreeneBusiness Member
    OP
    Real Estate Consultant · Madison, NJ · Member since 2016 · 6k+ posts · 7k+ votes
    1y
    Quote from @Shawn Ackerman:

    Great advice man!!!! I took a long break and I'm paying for it now LOL!! Expenses do not take a break so until you have no expenses taking breaks should be quick and infrequent.  Better yet train others to keep things going while you take your break.

    Again Jonathan thanks for the reminder that the grind never stops.  Addicted to the process not the end result!

    I love this - expenses do not take a break. Nice. I think the reason people take breaks is because they get discouraged that they can't buy or deals won't pencil in their antiquated buy boxes with 3 percent rates. Reps and going to meetups and building relationships and looking at deals in person are what help you fall into a deal. Thanks for the great response. The process!

  • Member since 2024 · 14 posts · 4 votes
    1y

    Great point, Jonathan!

    Confirms my thought process as a Renovation Project Manager- turning Investor. I am trying to brainstorm ways to partner locally with someone in or around Indianapolis, to offer "boots on the ground" as this is what I do and where my passion is already. So, How does one leverage this very important area of an investors responsibility and (for lack of better way to present it), market or signal to other investors who may be looking to partner?  

  • Jonathan GreeneBusiness Member
    OP
    Real Estate Consultant · Madison, NJ · Member since 2016 · 6k+ posts · 7k+ votes
    1y
    Quote from @Chad Swartz:

    Great point, Jonathan!

    Confirms my thought process as a Renovation Project Manager- turning Investor. I am trying to brainstorm ways to partner locally with someone in or around Indianapolis, to offer "boots on the ground" as this is what I do and where my passion is already. So, How does one leverage this very important area of an investors responsibility and (for lack of better way to present it), market or signal to other investors who may be looking to partner?  


    There are a lot of people looking in Indy on here, but there is a tightrope you have to walk so you don't solicit. If Indy is your bag and you can help people, I would make sure you have a keyword alert on for Indy or Indianapolis and always answer those questions without asking for anything. If you prove you have the knowledge to help there, people will DM you without you having to ask. I re-read what you wrote and am not sure if you are the boots in Indy or you want them.

  • Member since 2024 · 14 posts · 4 votes
    1y

    Jonathan,

    Again, very good pointers. Thank you for that. I certainly do not want to come across as soliciting. I need to work on my introduction just to produce a back story to help others understand where I am. 

  • Ryan IrwinPro Member
    Investor · Ankeny, IA · Member since 2022 · 158 posts · 129 votes
    1y
    Quote from @Jonathan Greene:

     x1000%!  Little steps everyday moves the needle in a big way.  I think this applies in all aspects (fitness, relationships, career, etc.).  I'm a huge fan of habit tracking and I have found it's those boring, repetitive tasks done consistently is what are the game changers.  These build the momentum which then opens to opportunities.  Great post! 

  • Kerry Noble JrPro Member
    Investor · Indianapolis, IN · Member since 2018 · 2k+ posts · 1k+ votes
    1y
    Quote from @Jonathan Greene:
    Quote from @Chad Swartz:

    Great point, Jonathan!

    Confirms my thought process as a Renovation Project Manager- turning Investor. I am trying to brainstorm ways to partner locally with someone in or around Indianapolis, to offer "boots on the ground" as this is what I do and where my passion is already. So, How does one leverage this very important area of an investors responsibility and (for lack of better way to present it), market or signal to other investors who may be looking to partner?  


    There are a lot of people looking in Indy on here, but there is a tightrope you have to walk so you don't solicit. If Indy is your bag and you can help people, I would make sure you have a keyword alert on for Indy or Indianapolis and always answer those questions without asking for anything. If you prove you have the knowledge to help there, people will DM you without you having to ask. I re-read what you wrote and am not sure if you are the boots in Indy or you want them.

    Ive done that for the last 7 years.......since I joined in 2018.......You gave away my secret weapon lol
  • Jay HinrichsBusiness Member
    Real Estate Consultant · Summerlin, NV · Member since 2014 · 45k+ posts · 66k+ votes
    1y
    Quote from @Shawn Ackerman:

    Great advice man!!!! I took a long break and I'm paying for it now LOL!! Expenses do not take a break so until you have no expenses taking breaks should be quick and infrequent.  Better yet train others to keep things going while you take your break.

    Again Jonathan thanks for the reminder that the grind never stops.  Addicted to the process not the end result!


    shawn you still working Milwaukee ?
  • Jay HinrichsBusiness Member
    Real Estate Consultant · Summerlin, NV · Member since 2014 · 45k+ posts · 66k+ votes
    1y

    in my mind if your just talking 1 to 4 units  those should be able to be vetted in your head or on the back of a napkin in about 30 seconds.. Know your product. 

  • Shawn AckermanPro Member
    Real Estate Entrepreneur · Mid West, East Coast · Member since 2015 · 3k+ posts · 1k+ votes
    1y

    @Jay Hinrichs Long time man! Yesir still operating in the MKE market. 

  • Jonathan GreeneBusiness Member
    OP
    Real Estate Consultant · Madison, NJ · Member since 2016 · 6k+ posts · 7k+ votes
    1y
    Quote from @Ryan Irwin:
    Quote from @Jonathan Greene:

     x1000%!  Little steps everyday moves the needle in a big way.  I think this applies in all aspects (fitness, relationships, career, etc.).  I'm a huge fan of habit tracking and I have found it's those boring, repetitive tasks done consistently is what are the game changers.  These build the momentum which then opens to opportunities.  Great post! 

    You nailed it. Boring and consistent = wealth in life and business.
  • Michael K GallagherBusiness Member
    Real Estate Agent · Columbus OH · Member since 2018 · 1k+ posts · 1k+ votes
    1y

    great sentiment, especially now, after the hype train of the covid, its interesting to see who is sticking around, keeping their heads down and putting in the work.

  • Member since 2024 · 222 posts · 161 votes
    1y

    Absolutely agree.  I'm taking a break now only because I'm retiring.  Over the 30+ years my wife and I have walked and pencilled well over a thousand possible deals.  That was after vetting many properties eliminating them before starting out.

    The more you do.  The more experience earned, you gain insight into comparables, learn neighborhoods, get better and better in determining a real deal from a stinker.

  • Jonathan GreeneBusiness Member
    OP
    Real Estate Consultant · Madison, NJ · Member since 2016 · 6k+ posts · 7k+ votes
    1y
    Quote from @Charles Perkins:

    Absolutely agree.  I'm taking a break now only because I'm retiring.  Over the 30+ years my wife and I have walked and pencilled well over a thousand possible deals.  That was after vetting many properties eliminating them before starting out.

    The more you do.  The more experience earned, you gain insight into comparables, learn neighborhoods, get better and better in determining a real deal from a stinker.


    Sounds like you earned a little break now!

  • Rental Property Investor · Perry Hall, MD · Member since 2016 · 587 posts · 599 votes
    1y
    Quote from @Jonathan Greene:

    Taking action isn't only investing in real estate. You should take a break from buying if the deals don't match your buy box, you are out of money, or for several other reasons (partner isn't on board, over-leveraged on different properties, acting out of FOMO, etc.). Still, you should never take a break from looking, touring, vetting, and analyzing. You can't take six months off from reviewing properties and hop back in like nothing happened. Stuff happened.

    If I were to sum up the one thing that I think investors aren't doing enough, it would be getting real-life reps. Real-life reps, to me, means seeing properties in person, whatever your asset class. What you see on the spreadsheet is a small part of every story. Boots on the ground, or lack thereof, are where the mistakes are made. Of course, the smaller the property, the more necessary that you see every inch of it because there isn't a business running on top of the land like large-scale multifamily, self-storage, industrial, and more. But even if you want to do large deals, you need comparable reps.

    Technology has made it easy to "analyze" deals. Still, if you aren't whittling down the number you are analyzing financially to a small subset you see before deciding what to do, you are missing an essential part of getting to the tipping point of expertise in your field. The most successful investors have looked at thousands of properties in person in their lifetimes. So, even when the market is challenging, you can still see properties and stay current.

    Don't take a break when the rates are high. Don't take a break when the weather is terrible. Don't take a break when others are taking a break. Removing all skills from the equation, if you don't take a break from participating as a real estate investor in some way each day, you will stay far ahead of everyone else who keeps subbing themselves out and then asking to get back in when the game is already out of reach.


    I respectfully and emphatically disagree. Take a break when you need to take a break. Whether it's for a month, or 6, or a year. Burnout is a real thing and there are more important things than real estate investing. I don't care if I'm ahead or behind of anyone else because my goals are not relative to anyone else's progress.

    I get your point that staying active keeps your skills sharp and that if you're active when others aren't you will have access to opportunities that they do not. You'll also continue to be building your brand, your network, your experience, etc. But if it's coming at the cost of your health or something else important than time with your family then it's perfectly fine to step back when you need to.

  • Member since 2024 · 14 posts · 4 votes
    1y

    As @JonathanGreene said, tech has created an environment that allows folks like you Jon, to enjoy investing on your terms so that you do not put all of your eggs into one basket (so-to-speak). Some absolutely put all eggs on deck, investing is all that they do. I think this site may be geared a bit more toward the avid investor, rather that the weekend warrior type of investors with regular, RE carriers

    On the other hand, for myself, watching the RE market is enjoyable for me.I have always attended open houses just to be nosey or nerdy, whichever you prefer. It's like playing the couponing game and a store gives you money at the check out. I have had it happen!

  • Jonathan GreeneBusiness Member
    OP
    Real Estate Consultant · Madison, NJ · Member since 2016 · 6k+ posts · 7k+ votes
    1y
    Quote from @Jon K.:
    Quote from @Jonathan Greene:

    Taking action isn't only investing in real estate. You should take a break from buying if the deals don't match your buy box, you are out of money, or for several other reasons (partner isn't on board, over-leveraged on different properties, acting out of FOMO, etc.). Still, you should never take a break from looking, touring, vetting, and analyzing. You can't take six months off from reviewing properties and hop back in like nothing happened. Stuff happened.

    If I were to sum up the one thing that I think investors aren't doing enough, it would be getting real-life reps. Real-life reps, to me, means seeing properties in person, whatever your asset class. What you see on the spreadsheet is a small part of every story. Boots on the ground, or lack thereof, are where the mistakes are made. Of course, the smaller the property, the more necessary that you see every inch of it because there isn't a business running on top of the land like large-scale multifamily, self-storage, industrial, and more. But even if you want to do large deals, you need comparable reps.

    Technology has made it easy to "analyze" deals. Still, if you aren't whittling down the number you are analyzing financially to a small subset you see before deciding what to do, you are missing an essential part of getting to the tipping point of expertise in your field. The most successful investors have looked at thousands of properties in person in their lifetimes. So, even when the market is challenging, you can still see properties and stay current.

    Don't take a break when the rates are high. Don't take a break when the weather is terrible. Don't take a break when others are taking a break. Removing all skills from the equation, if you don't take a break from participating as a real estate investor in some way each day, you will stay far ahead of everyone else who keeps subbing themselves out and then asking to get back in when the game is already out of reach.


    I respectfully and emphatically disagree. Take a break when you need to take a break. Whether it's for a month, or 6, or a year. Burnout is a real thing and there are more important things than real estate investing. I don't care if I'm ahead or behind of anyone else because my goals are not relative to anyone else's progress.

    I get your point that staying active keeps your skills sharp and that if you're active when others aren't you will have access to opportunities that they do not. You'll also continue to be building your brand, your network, your experience, etc. But if it's coming at the cost of your health or something else important than time with your family then it's perfectly fine to step back when you need to.


    I think this goes without saying. If your mental health is compromised by looking at deals, you should stop. But that's not in any way what the post was saying. There was no pressure to stay in; it was about getting reps and not opting out. If your mental health is so fractured that you can't go to an Open House on a four-family down the block from you, that is something to focus on first. It's a commentary on those who take breaks because of market dynamics or because their buy box is too tight for the current market.

  • Rental Property Investor · Perry Hall, MD · Member since 2016 · 587 posts · 599 votes
    1y
    Quote from @Jonathan Greene:
    Quote from @Jon K.:
    Quote from @Jonathan Greene:

    Taking action isn't only investing in real estate. You should take a break from buying if the deals don't match your buy box, you are out of money, or for several other reasons (partner isn't on board, over-leveraged on different properties, acting out of FOMO, etc.). Still, you should never take a break from looking, touring, vetting, and analyzing. You can't take six months off from reviewing properties and hop back in like nothing happened. Stuff happened.

    If I were to sum up the one thing that I think investors aren't doing enough, it would be getting real-life reps. Real-life reps, to me, means seeing properties in person, whatever your asset class. What you see on the spreadsheet is a small part of every story. Boots on the ground, or lack thereof, are where the mistakes are made. Of course, the smaller the property, the more necessary that you see every inch of it because there isn't a business running on top of the land like large-scale multifamily, self-storage, industrial, and more. But even if you want to do large deals, you need comparable reps.

    Technology has made it easy to "analyze" deals. Still, if you aren't whittling down the number you are analyzing financially to a small subset you see before deciding what to do, you are missing an essential part of getting to the tipping point of expertise in your field. The most successful investors have looked at thousands of properties in person in their lifetimes. So, even when the market is challenging, you can still see properties and stay current.

    Don't take a break when the rates are high. Don't take a break when the weather is terrible. Don't take a break when others are taking a break. Removing all skills from the equation, if you don't take a break from participating as a real estate investor in some way each day, you will stay far ahead of everyone else who keeps subbing themselves out and then asking to get back in when the game is already out of reach.


    I respectfully and emphatically disagree. Take a break when you need to take a break. Whether it's for a month, or 6, or a year. Burnout is a real thing and there are more important things than real estate investing. I don't care if I'm ahead or behind of anyone else because my goals are not relative to anyone else's progress.

    I get your point that staying active keeps your skills sharp and that if you're active when others aren't you will have access to opportunities that they do not. You'll also continue to be building your brand, your network, your experience, etc. But if it's coming at the cost of your health or something else important than time with your family then it's perfectly fine to step back when you need to.


    I think this goes without saying. If your mental health is compromised by looking at deals, you should stop. But that's not in any way what the post was saying. There was no pressure to stay in; it was about getting reps and not opting out. If your mental health is so fractured that you can't go to an Open House on a four-family down the block from you, that is something to focus on first. It's a commentary on those who take breaks because of market dynamics or because their buy box is too tight for the current market.


     It only goes without saying if you’re dealing with a smarter person than myself. In that case I respectfully and emphatically agree.

  • Valhalla, NY · Member since 2013 · 132 posts · 84 votes
    1y

    Great post!! One small step forward each day! Love it! 

  • Lender · Tyler, TX · Member since 2016 · 49 posts · 23 votes
    1y

    Great advice! 

  • Rental Property Investor · San Francisco Bay Area · Member since 2022 · 1k+ posts · 1k+ votes
    1y

    I'm taking a break from buying and my previous approach of analyzing deals in inexpensive markets, looking at hundreds of properties on Zillow and running the numbers, which I spent hours each on each day and became really burned out. Buying RE is nothing like buying index funds or stocks - Google it for 15 minutes, click on buy shares. And the exit strategy with RE is much more difficult if you buy a property doesn't align with your goals.

    I completely agree with getting reps in real life, walking properties, talking to contractors and investors. This is what I recommend to new investors who contact me asking if these numbers look good. I'm now figuring out how to maximize the return on current properties and add value, efficient ways to self manage, etc. I still attend local meet ups and talk to dozens of investors and am considering other strategies like Mid-Term Rentals or rent by the room. Taking a break from buying but not from learning and networking. 

  • Jonathan GreeneBusiness Member
    OP
    Real Estate Consultant · Madison, NJ · Member since 2016 · 6k+ posts · 7k+ votes
    1y
    Quote from @Becca F.:

    I'm taking a break from buying and my previous approach of analyzing deals in inexpensive markets, looking at hundreds of properties on Zillow and running the numbers, which I spent hours each on each day and became really burned out. Buying RE is nothing like buying index funds or stocks - Google it for 15 minutes, click on buy shares. And the exit strategy with RE is much more difficult if you buy a property doesn't align with your goals.

    I completely agree with getting reps in real life, walking properties, talking to contractors and investors. This is what I recommend to new investors who contact me asking if these numbers look good. I'm now figuring out how to maximize the return on current properties and add value, efficient ways to self manage, etc. I still attend local meet ups and talk to dozens of investors and am considering other strategies like Mid-Term Rentals or rent by the room. Taking a break from buying but not from learning and networking. 


    Yeah, that's it exactly. It's just not opting out of being a real estate investor. Sometimes there's nothing to buy. Sometimes analyzing is too time-consuming. So, we network and build, and then learn, based on our past experience, how to analyze more efficiently or how to shrink our buy box.

  • Member since 2024 · 14 posts · 4 votes
    1y

    Jonathan, 

    It stinks when there are obvious great deals that go by, not being quite able to jump on- board. I need to focus on helping others shrink "busy boxes". 

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