Why You Should Stop Talking About Quitting Your Job Before You Have Your 1st Property

[Jonathan Greene]

This trend has been growing increasingly, but it's actually hurting most new investors. I've read so many posts from people in their early 20s talking about getting out of the rat race before they are even in it. Maybe it's social media. Sometimes, it's just not wanting to work. Or work for someone else. But it won't help you get more properties if you quit your job too early.

Please stop talking about quitting your job before you have your first property—or your second—or your third. Keep your job as long as you can. And then keep it two years longer. Here's why:

1. Having a steady job with steady and expected pay is the foundation you need to invest because you know the money will keep coming in as long as you don't get fired. You want a strong foundation that is compounding, not a house of cards with no base.

2. Having full-time employment is what makes you lendable. Traditional lenders don't care about your savings or net worth; they care about your employment and earnings.

3. Your job is your runway. You want to build the longest runway possible. You don't want one where you can barely land and take off. You want one with plenty of room to land and turn around while another plane takes off. (You're welcome to the pilots out there.)

4. If you use your job as a springboard and keep getting raises, you keep increasing your lendability and ability to get more properties. Don't just do your job, be the best at it. No matter your industry, being good at your job will help you as a real estate investor.

5. Your mindset is corrupted if you only think about leaving your job to be free. Owning rental properties is not freedom. If you self-manage, you will probably work more hours than you did before. A lot of people realize later that they traded a steady, easy job with the weekends off for an unpredictable, annoying job that is 24/7.

Remember that you aren't chasing financial freedom; you are chasing time freedom. Time freedom is different for everyone. If you make $100k working 10-5 Monday through Friday with 3 weeks of vacation and your weekends are free, that might be time freedom to you.

If you are into the FIRE movement, why do you want to retire early? Retire from what? When you love what you do, it's not something you retire from. But you have to grow into that.

Add any more to the list in your responses.

[Adam Odom]

Quote from @Alan F.:

Jobs have; PTO, medical insurance, Company matched 401k's, structure etc. Lending favors w2 employment.

Self employed have; Non of the above.

 Came here to say this exactly - insurance alone is a huge expense most don't think about until they have to pay it outright. And company match on 401k is free money. 

[James Hamling]

Thing is @Jonathan Greene, your message, as true as it may be, comes across to a whole generation like that of the person giving away apples and tooth brushes for Halloween..... 

They don't really care so much about facts, reality, what's good or bad, they just want a giant damn snickers to cram in there pie-hole, and to feel guilt free when there doing it.

Now before ya-shake your fist in the air over the collective stupidity/insanity of it all keep in mind, these are the same kids that we all decided to raise where nobody got 1st, 2nd or 3rd place anymore, no-no-no, we said that would hurt feelings so we decided regardless of actions EVERYONE got a medal, the exact same medal. 

So we raise em, train em and condition em, in a complete fantasy realm where all you have to do is want, nobody ever "fails", anything that hurts feelings is swiftly removed from existence and all of life is padded corners and warm-fuzzies..... 

Until out of school and then it's straight into the pit and good luck fighting for survival, get with reality and all that....... 

Yeah, were freaking morons for expecting anything different to have resulted from raising a generation of human cat's...... Which interestingly enough now they can actually define themselves as literal human-cat's and even demand a litter box and it will be done. And if any speak ill of it there billed a Nazi Fascist Bigot...... 

So am I every shocked by reality disconnect, no, that's the new norm. 

[Jonathan Greene]

Quote from @James Hamling:

Thing is @Jonathan Greene, your message, as true as it may be, comes across to a whole generation like that of the person giving away apples and tooth brushes for Halloween..... 

They don't really care so much about facts, reality, what's good or bad, they just want a giant damn snickers to cram in there pie-hole, and to feel guilt free when there doing it.

Now before ya-shake your fist in the air over the collective stupidity/insanity of it all keep in mind, these are the same kids that we all decided to raise where nobody got 1st, 2nd or 3rd place anymore, no-no-no, we said that would hurt feelings so we decided regardless of actions EVERYONE got a medal, the exact same medal. 

So we raise em, train em and condition em, in a complete fantasy realm where all you have to do is want, nobody ever "fails", anything that hurts feelings is swiftly removed from existence and all of life is padded corners and warm-fuzzies..... 

Until out of school and then it's straight into the pit and good luck fighting for survival, get with reality and all that....... 

Yeah, were freaking morons for expecting anything different to have resulted from raising a generation of human cat's...... Which interestingly enough now they can actually define themselves as literal human-cat's and even demand a litter box and it will be done. And if any speak ill of it there billed a Nazi Fascist Bigot...... 

So am I every shocked by reality disconnect, no, that's the new norm. 

Participation trophy culture runs rampant next to abject fragility as a guise to avoid responsibility and ownership. So, yeah, I agree.

[James Hamling]

Quote from @Jonathan Greene:

Quote from @James Hamling:

Thing is @Jonathan Greene, your message, as true as it may be, comes across to a whole generation like that of the person giving away apples and tooth brushes for Halloween..... 

They don't really care so much about facts, reality, what's good or bad, they just want a giant damn snickers to cram in there pie-hole, and to feel guilt free when there doing it.

Now before ya-shake your fist in the air over the collective stupidity/insanity of it all keep in mind, these are the same kids that we all decided to raise where nobody got 1st, 2nd or 3rd place anymore, no-no-no, we said that would hurt feelings so we decided regardless of actions EVERYONE got a medal, the exact same medal. 

So we raise em, train em and condition em, in a complete fantasy realm where all you have to do is want, nobody ever "fails", anything that hurts feelings is swiftly removed from existence and all of life is padded corners and warm-fuzzies..... 

Until out of school and then it's straight into the pit and good luck fighting for survival, get with reality and all that....... 

Yeah, were freaking morons for expecting anything different to have resulted from raising a generation of human cat's...... Which interestingly enough now they can actually define themselves as literal human-cat's and even demand a litter box and it will be done. And if any speak ill of it there billed a Nazi Fascist Bigot...... 

So am I every shocked by reality disconnect, no, that's the new norm. 

Participation trophy culture runs rampant next to abject fragility as a guise to avoid responsibility and ownership. So, yeah, I agree.

Just sayin....... 

[Casey Clement Baxter]

Also, if you’re primarily focused on maximizing cash flow quickly so you can quit your day job as soon as possible, you’re probably not investing in properties that will enjoy the greatest appreciation over time.  

It’s a shame that real estate is often touted as a ‘get rich quick’ scheme.  In my experience RE investing is a reliable way to get rich slow, provided that you’re willing to invest steady effort and attention into the proper management of your portfolio over an extended period of time.  

[Becca F.]

Quote from @Casey Clement Baxter:

Also, if you’re primarily focused on maximizing cash flow quickly so you can quit your day job as soon as possible, you’re probably not investing in properties that will enjoy the greatest appreciation over time.  

It’s a shame that real estate is often touted as a ‘get rich quick’ scheme.  In my experience RE investing is a reliable way to get rich slow, provided that you’re willing to invest steady effort and attention into the proper management of your portfolio over an extended period of time.  

 Lots of great comments. I had 3 solid appreciating properties and was looking to grow my portfolio. I listened to some of these gurus (including a few people on BP) about acquiring doors to have "financial freedom" and bought 2 Class C properties in Indianapolis, not hating the city just my choice of property purchases - that cash flow on paper has turned out to be -$300 to -$500 a month. I decided to stop buying and re-assess. 

These gurus leave out of a lot of information and were lucky to scale that quickly from pre-2012 to 2021, which is really hard to do now in 2024. I do know 3 people who scaled quickly, 7 years, but they had a lot of capital ($400,000+ W2 income which most people in the USA don't earn) and benefitted from the huge run up in property values. Most of the California investors with substantial net worth that I know have owned properties for 15 to 30+ years. 

I'm not sure why the current trend is to hate your W2 job especially for someone in their 20s/30s and quit ASAP become a RE investor or entrepreneur. I started to change my mindset, and figure out ways to work efficiently and reduce work stress. As Thanksgiving approaches, I'm very thankful to I have a W2 job with substantial raises - it could be a lot worse. 

[Jonathan Greene]

Quote from @Becca F.:

Quote from @Casey Clement Baxter:

Also, if you’re primarily focused on maximizing cash flow quickly so you can quit your day job as soon as possible, you’re probably not investing in properties that will enjoy the greatest appreciation over time.  

It’s a shame that real estate is often touted as a ‘get rich quick’ scheme.  In my experience RE investing is a reliable way to get rich slow, provided that you’re willing to invest steady effort and attention into the proper management of your portfolio over an extended period of time.  

 Lots of great comments. I had 3 solid appreciating properties and was looking to grow my portfolio. I listened to some of these gurus (including a few people on BP) about acquiring doors to have "financial freedom" and bought 2 Class C properties in Indianapolis, not hating the city just my choice of property purchases - that cash flow on paper has turned out to be -$300 to -$500 a month. I decided to stop buying and re-assess. 

These gurus leave out of a lot of information and were lucky to scale that quickly from pre-2012 to 2021, which is really hard to do now in 2024. I do know 3 people who scaled quickly, 7 years, but they had a lot of capital ($400,000+ W2 income which most people in the USA don't earn) and benefitted from the huge run up in property values. Most of the California investors with substantial net worth that I know have owned properties for 15 to 30+ years. 

I'm not sure why the current trend is to hate your W2 job especially for someone in their 20s/30s and quit ASAP become a RE investor or entrepreneur. I started to change my mindset, and figure out ways to work efficiently and reduce work stress. As Thanksgiving approaches, I'm very thankful to I have a W2 job with substantial raises - it could be a lot worse. 

It's a weird thing to be young and anti-W2 job. Even if you don't get paid a lot, you get paid at the same time every week or month and you can count on it. You don't get a call from your W2 on Christmas Eve to come unclog the toilet (unless that's your job).

What was the reason your properties in Indy ended up negative cash flow? Did you buy from a turnkey company or just through an agent?

[Jim K.]

Well, this is a wonderful thread.

All I can really contribute with enough experience to be absolutely sure of what I say: if you live on the coasts and your spreadsheet tells you your best passive returns over the long haul are going to be in the Rust Belt in cheap rentals, then your spreadsheet needs to be looked at by someone with a lot more experience in cheap Rust Belt rentals than you have.

My own take on the musings here of why everyone wants to quit their job these day and its possible connection to young people and their participation trophies, their possible work-ethic failings, moral turpitude, contemptible world outlook, lack of grit, et hoc genus omne...yeah, I know I don't know squat about all that.

[Becca F.]

Quote from @Jonathan Greene:

Quote from @Becca F.:

Quote from @Casey Clement Baxter:

Also, if you’re primarily focused on maximizing cash flow quickly so you can quit your day job as soon as possible, you’re probably not investing in properties that will enjoy the greatest appreciation over time.  

It’s a shame that real estate is often touted as a ‘get rich quick’ scheme.  In my experience RE investing is a reliable way to get rich slow, provided that you’re willing to invest steady effort and attention into the proper management of your portfolio over an extended period of time.  

 Lots of great comments. I had 3 solid appreciating properties and was looking to grow my portfolio. I listened to some of these gurus (including a few people on BP) about acquiring doors to have "financial freedom" and bought 2 Class C properties in Indianapolis, not hating the city just my choice of property purchases - that cash flow on paper has turned out to be -$300 to -$500 a month. I decided to stop buying and re-assess. 

These gurus leave out of a lot of information and were lucky to scale that quickly from pre-2012 to 2021, which is really hard to do now in 2024. I do know 3 people who scaled quickly, 7 years, but they had a lot of capital ($400,000+ W2 income which most people in the USA don't earn) and benefitted from the huge run up in property values. Most of the California investors with substantial net worth that I know have owned properties for 15 to 30+ years. 

I'm not sure why the current trend is to hate your W2 job especially for someone in their 20s/30s and quit ASAP become a RE investor or entrepreneur. I started to change my mindset, and figure out ways to work efficiently and reduce work stress. As Thanksgiving approaches, I'm very thankful to I have a W2 job with substantial raises - it could be a lot worse. 

It's a weird thing to be young and anti-W2 job. Even if you don't get paid a lot, you get paid at the same time every week or month and you can count on it. You don't get a call from your W2 on Christmas Eve to come unclog the toilet (unless that's your job).

What was the reason your properties in Indy ended up negative cash flow? Did you buy from a turnkey company or just through an agent?

 Bought with an agent. Home was built in 1920, renovated by a flipper and on the market for 80 days. I think I got a good deal as far as purchase price. The house went through a full inspection with some minor repairs costing $1500. The HVAC and water heater estimated to be 6 to 8 years old by the inspector. AC unit is brand new. After the tenant moved in the repair calls starting coming in 9 times in 12 months - backdoor was stuck again (that was part of minor repairs), heat went out, AC not cooling, kitchen sink leaking,  etc. And the new AC unit (seller put in) was stolen right before move in - thieves climbed a 7 foot fence. No one told me to get a cage around it until I started asking questions after the fact. 

I was on the phone with the Maintenance Coordinator multiple times asking what was going on and if the tenant was breaking things or was it my fault as the owner. My net income is $71 a month now (if no repairs) after the recent property tax increase. For all the talk about cash flow, I'm cash flowing way more from my high yield savings account. 

I was told by contractors that a home may pass an inspection but once someone is living in it and putting daily stress on the house, things will start to malfunction. And that it takes 12 to 18 months for a house stabilize (no repair calls for 4 months so far). I didn't walk the house prior to making an offer and prior to closing. iI won't ever close on another OOS property without walking it first. 

Another investor said I shouldn't buy properties from flippers since you don't know how good the renovation was - is this an accurate assessment? This is going off the original topic - I could post as a separate topic.

[Jonathan Greene]

Quote from @Becca F.:

Quote from @Jonathan Greene:

Quote from @Becca F.:

Quote from @Casey Clement Baxter:

Also, if you’re primarily focused on maximizing cash flow quickly so you can quit your day job as soon as possible, you’re probably not investing in properties that will enjoy the greatest appreciation over time.  

It’s a shame that real estate is often touted as a ‘get rich quick’ scheme.  In my experience RE investing is a reliable way to get rich slow, provided that you’re willing to invest steady effort and attention into the proper management of your portfolio over an extended period of time.  

 Lots of great comments. I had 3 solid appreciating properties and was looking to grow my portfolio. I listened to some of these gurus (including a few people on BP) about acquiring doors to have "financial freedom" and bought 2 Class C properties in Indianapolis, not hating the city just my choice of property purchases - that cash flow on paper has turned out to be -$300 to -$500 a month. I decided to stop buying and re-assess. 

These gurus leave out of a lot of information and were lucky to scale that quickly from pre-2012 to 2021, which is really hard to do now in 2024. I do know 3 people who scaled quickly, 7 years, but they had a lot of capital ($400,000+ W2 income which most people in the USA don't earn) and benefitted from the huge run up in property values. Most of the California investors with substantial net worth that I know have owned properties for 15 to 30+ years. 

I'm not sure why the current trend is to hate your W2 job especially for someone in their 20s/30s and quit ASAP become a RE investor or entrepreneur. I started to change my mindset, and figure out ways to work efficiently and reduce work stress. As Thanksgiving approaches, I'm very thankful to I have a W2 job with substantial raises - it could be a lot worse. 

It's a weird thing to be young and anti-W2 job. Even if you don't get paid a lot, you get paid at the same time every week or month and you can count on it. You don't get a call from your W2 on Christmas Eve to come unclog the toilet (unless that's your job).

What was the reason your properties in Indy ended up negative cash flow? Did you buy from a turnkey company or just through an agent?

 Bought with an agent. Home was built in 1920, renovated by a flipper and on the market for 80 days. I think I got a good deal as far as purchase price. The house went through a full inspection with some minor repairs costing $1500. The HVAC and water heater estimated to be 6 to 8 years old by the inspector. AC unit is brand new. After the tenant moved in the repair calls starting coming in 9 times in 12 months - backdoor was stuck again (that was part of minor repairs), heat went out, AC not cooling, kitchen sink leaking,  etc. And the new AC unit (seller put in) was stolen right before move in - thieves climbed a 7 foot fence. No one told me to get a cage around it until I started asking questions after the fact. 

I was on the phone with the Maintenance Coordinator multiple times asking what was going on and if the tenant was breaking things or was it my fault as the owner. My net income is $71 a month now (if no repairs) after the recent property tax increase. For all the talk about cash flow, I'm cash flowing way more from my high yield savings account. 

I was told by contractors that a home may pass an inspection but once someone is living in it and putting daily stress on the house, things will start to malfunction. And that it takes 12 to 18 months for a house stabilize (no repair calls for 4 months so far). I didn't walk the house prior to making an offer and prior to closing. iI won't ever close on another OOS property without walking it first. 

Another investor said I shouldn't buy properties from flippers since you don't know how good the renovation was - is this an accurate assessment? This is going off the original topic - I could post as a separate topic.

That is super helpful for those looking out of state. This is why I prefer vetted and vertically integrated turnkey, which is what I am looking into now. Thanks for posting all of that, I think someone can get saved from just reading it. At least it's positive now, but it's almost like you have to keep it now to recoup in appreciation if possible. Also sounds like the inspector underwhelmed.

[Henry Clark]

Having been thru the corporate world, I came to understand wanting to be financially free, in charge, reaping benefits beyond salary which was good. 

To get into REI we didn't use BP or other forums. But BP is built on churn. All of us responding support churn for different reasons. Mine is boredom between Self Storage and Country subdivisions. Also responding has sharpened my deal analysis.

If I was to talk with all of these potential investors.  I would tell them what I wished I had known. 

1.  Join the military.  My entire extended family is military.  Would do it just out of pride.  But with BAH base allowance housing. $15,000 to $50,000 tax free annually.  You’re guaranteed to be a millionaire after 20 years plus have training, retirement, benefits.  Plus you got to see the world.  

2.  Texas property tax sales.  Just land.  Don’t go to the auctions.  Make offers on off sale properties. 

3. Primary residence capital gain $250,000 exclusion. Buy the worst house in a great neighborhood, do rehab, ADU, lot split.

4.  Nasty.  Invest in properties others don’t have the vision.  Not necessarily dirty.  

None of these are $200 per door in a C neighborhood.  

So understand the desire for financial freedom.  They just need to run the numbers.  Also to risk adjust the returns.  Build a Scale model and see what it takes to get to your number.  

Start small and Make Your Big Mistakes Early.  

[Joe S.]

Quote from @Henry Clark:

Having been thru the corporate world, I came to understand wanting to be financially free, in charge, reaping benefits beyond salary which was good. 

To get into REI we didn't use BP or other forums. But BP is built on churn. All of us responding support churn for different reasons. Mine is boredom between Self Storage and Country subdivisions. Also responding has sharpened my deal analysis.

If I was to talk with all of these potential investors.  I would tell them what I wished I had known. 

1.  Join the military.  My entire extended family is military.  Would do it just out of pride.  But with BAH base allowance housing. $15,000 to $50,000 tax free annually.  You’re guaranteed to be a millionaire after 20 years plus have training, retirement, benefits.  Plus you got to see the world.  

2.  Texas property tax sales.  Just land.  Don’t go to the auctions.  Make offers on off sale properties. 

3. Primary residence capital gain $250,000 exclusion. Buy the worst house in a great neighborhood, do rehab, ADU, lot split.

4.  Nasty.  Invest in properties others don’t have the vision.  Not necessarily dirty.  

None of these are $200 per door in a C neighborhood.  

So understand the desire for financial freedom.  They just need to run the numbers.  Also to risk adjust the returns.  Build a Scale model and see what it takes to get to your number.  

Start small and Make Your Big Mistakes Early.  

I have never bought anything from the taxes sale in Texas. Any more pointers on this? :-) 

[Henry Clark]

Quote from @Joe S.:

Quote from @Henry Clark:

Having been thru the corporate world, I came to understand wanting to be financially free, in charge, reaping benefits beyond salary which was good. 

To get into REI we didn't use BP or other forums. But BP is built on churn. All of us responding support churn for different reasons. Mine is boredom between Self Storage and Country subdivisions. Also responding has sharpened my deal analysis.

If I was to talk with all of these potential investors.  I would tell them what I wished I had known. 

1.  Join the military.  My entire extended family is military.  Would do it just out of pride.  But with BAH base allowance housing. $15,000 to $50,000 tax free annually.  You’re guaranteed to be a millionaire after 20 years plus have training, retirement, benefits.  Plus you got to see the world.  

2.  Texas property tax sales.  Just land.  Don’t go to the auctions.  Make offers on off sale properties. 

3. Primary residence capital gain $250,000 exclusion. Buy the worst house in a great neighborhood, do rehab, ADU, lot split.

4.  Nasty.  Invest in properties others don’t have the vision.  Not necessarily dirty.  

None of these are $200 per door in a C neighborhood.  

So understand the desire for financial freedom.  They just need to run the numbers.  Also to risk adjust the returns.  Build a Scale model and see what it takes to get to your number.  

Start small and Make Your Big Mistakes Early.  

I have never bought anything from the taxes sale in Texas. Any more pointers on this? :-) 

Google to get specifics.

1.  Only do land.  You take possession in 6 months.  Houses take 2 or 3 years, can’t remember specifics.

2.  Only do off auction properties. Actually a lot of properties the taxing authorities don’t put up for auction.  If $25,000 back taxes offer $4,000.  Gets it back in the tax rolls.

3.   Check the following.   Are there other taxes past due.  Drainage districts, certain school taxes.   Are the taxes being auctioned to the current date. 2024 versus 2022 and more taxes are due.

4.  What happens if they pay the taxes?  You get your money back plus varying amounts 25% for year one, 50% year two etc.  Check this.  

5.  So which properties do you want to make offers on.  My brother and nieces did or looked at these.  
10 acre subdivision lot two houses down.  Paid $10,000 sold for $50,000 two years later. Mowed the grass.  

6 acres in the highway in the middle of town for $8,000 sold 1 year later for $200,000.  

One lot looked at.  Had high lines above and with setbacks you can’t build. Could do parking and cargo container storage.

 4 acre lot needed 200 yards of rock in dirt road.  Drainage went through the property. I see a small pond with the land split into 2 lots. 25 miles away from Dallas.  

There is no zoning in Texas counties.  Get the land and find a purpose.  

[Kay S.]

All this. As someone who made a very healthy 6 figure W2 income for years, I only really appreciated the leverage power it held when I lost it due to a company reorg. I didn’t realize it then but thanks to this community ( and more than a year of unemployment ) I have learned I should have taken advantage of the W2 lending benefits when I had the chance. Part of the “dream” of financial independence doesn’t have to be quitting your W2.it can just be the knowledge that you CAN quit should you decide to. I have a former colleague who always said if she won the lottery, she wouldn’t quit right away. She would stay around and tell people the truth about the work they were doing. Real estate gives you the same “N f-s to give “ attitude.which, weirdly might actually make you a more impactful employee … leading to more $$$ which you can leverage for more real estate 💕