Should I Invest in Real Estate or the Stock Market?

(Image courtesy of Tierra Mallorca)

If you’re at the beginning stage of investing, and you clicked on this article, there’s a good chance you’re wondering, “Wait, how do I know if real estate is a better bet than the stock market?  Or is one even better than the other?”

Well, spoiler alert, I have my own bias.  I’ve built my life around real estate and it’s paid off many times over (with a bit of hard work, of course).  

That said, there are pros and cons to investing in real estate and investing in the stock market (and other assets, for that matter).  It’s definitely worth exploring the differences between them.  Much of it comes down to lifestyle and how hands-on vs. hands-off you’re willing to be.

The Stock Market: Pros and Cons


  1. Low-to-no maintenance

Any type of investing requires you do your homework, so it’s not quite accurate to say that investing in the stock market means you just “set it and forget it.”

But that said, you will most likely have far more free time on your hands if you invest in the stock market over real estate.  

For one thing, a stock portfolio doesn’t require a team of subcontractors, a real estate agent, a potential buyer/tenant or a banker.  Then there’s the consideration that a share of stock is not a physical item, and therefore you won’t have to drive anywhere, inspect anything or run errands.

Time is a precious commodity we are constantly evaluating against money.  For some people, the time (and energy) factor means that real estate is a deal-breaker, and the stock market a more realistic choice.

  1. Reasonably Secure

I’m no expert in stock investing, so take this with a grain of salt, but at long as you do your homework upfront you are most likely to get a reasonable, if not really good return over time. Mutual funds are a particularly great way to do this: you can quickly diversify by owning a share of multiple different, strongly-performing companies.

There are so many more resources and gurus available today to help you start out on the right foot.  As long as you apply common sense (don’t buy penny stocks, make sure you diversify) then you are looking forward to a nice return in the next 20 to 30 years.

  1. The Nerd Factor

There’s a certain enjoyment that comes from feeling like you’re witnessing history in the making, and the stock market is a great place for that.

Culture and technology drive the economy, and vice versa, and the results play out on Wall Street.  It’s a fun and tangible way to stay educated on current events as well as historical trends, and to even use that knowledge and “data” to make predictions about where the future is headed.

  1. Less Money Upfront (Usually)

It’s always better to invest more than less when you invest in anything, because a bigger investment means a bigger return. But the need to invest a large sum of money can be a big entry barrier for many people. The advantage of the stock market is that you can get started with as little as a few hundred bucks.

Real estate, as we have all seen in recent years, is hardly “cheap,” and will almost certainly require you to take out loans (unless you have a nice nest egg already saved up).  There is also the cost of closing on a property, of renovating and maintaining it, to name just a few.  There are certainly more moving parts in real estate, and that includes parts that will cost you.

I hesitate to put hard numbers on things, and a decent house in a good area will be a cheaper investment than one share of Berkshire Hathaway, but generally speaking, real estate will cost you more upfront.  The downside of that is offset by cash flow, which I’ll get to later in this article.


  1. No (Serious) Cash Flow

Investing in a share of stock means — for the most part — you make no money off it until you sell it.  Yes, you can earn dividends to cash out from time to time, but usually it’s a small return (unless you learn advanced techniques such as trading in options, these approaches are not for the average investor).

The only serious money you earn from stocks is the money you earn when you actually sell it.  It doesn’t matter how “high” your stock price rises — that rise in price means nothing until you sell it.  And once you do, that share of stock is now gone and you can no longer profit off it.

  1. (Very) Delayed Gratification

Because stocks don’t generate cash flow and only bring you money when you sell them, you will need to wait a while for the stock value to become high enough that you feel incentivized to sell.

What we are talking about is closer to decades than years, let alone months.  The main exception to this is if you decide to become a day trader, but that is something no one should try unless they really know what they’re doing (not to mention it will involve much more time and energy).

  1. Some Unpredictability

Even if you make the most educated choices possible with your portfolio, some of them are probably going to drop, rather than rise.  The economy (read: Planet Earth) can be an unpredictable thing and much of the stock market is based on assumptions made from what has happened in the past.  While there’s a good chance those assumptions will hold true, there will always be some surprises.

Of course, the same applies to real estate to some extent, but real estate is at least tangible (like gold) and people will always need a decent place to live.

The Real Estate Market: Pros and Cons


  1. As Stable as it Comes

There’s a reason that wealth has historically been associated with land:  it’s limited and almost always in demand.  People need a space to live, whether they own it or rent it. 

Certain neighborhoods or areas do depreciate in value but overall, real estate goes up.  Look no further than the housing crash in 2008 to the housing shortage crisis nation-wide now: even when demand goes down, it comes back up again.  If you do your homework you will know which neighborhoods have the best outlook, giving you an even further advantage.

Real estate is an old game, but a solid one.

  1. Cash Flow

This, right here, is the Number One reason I love real estate.

When you buy a share of stock, the only money you can earn with it is the money you get when you sell it (including any dividends).  In other words: there is no actual money going into your pocket until you sell it.  It’s a one-time pay-off.

Compare that to real estate: You can own a house (or apartment complex), anticipate one day earning money from selling that house, and then earn money in the meantime by renting it to others.  Money that you get right now, right into your pocket.

Think of it this way:

When you own a property, it’s like owning a goose that lays eggs.  You can earn money off the eggs now, and also when you sell the goose.

When you own a share of stock, there are no eggs.  There’s only the money you earn when you sell the goose.

Of course it’s a simplistic analogy, but it gets the point across: real estate, with enough work upfront, has the potential to earn you money both now and later.  Maintaining cash flow isn’t always easy, of course, but it’s more than possible.

  1. It’s Tangible

This one is slightly more emotion-based, but I believe it’s still important.

A share of stock sits in a digital folder.  You can’t touch it, smell it, walk inside it, admire it from across the street.  There is something very satisfying, by contrast, about physically laboring and putting effort into a property, and then being able to see and enjoy the results of your labors.  

Even a new layer of paint in a kitchen, or a new fence in the backyard is a visible and pleasing sign of your progress and your investment.  What’s even better is that it can bring joy to and improve the lives of those who will reside there.


  1. It Can Get Complicated

Real estate has many moving parts.  There will be many jobs that need to be done, and multiple people needed for those jobs, from the buying process, through the renovating and maintaining process, all the way until you decide to sell the property.

You will need to be very organized if you want to stay on top of things.  Because you will depend on others (whether it’s a realtor-broker, a handyman or a home inspector) you will need to learn how to build stable working relationships with others.  You may find yourself having to confront someone on a delicate issue every now and then.  You will also find yourself in the humble position of needing to build trust and rapport with moneylenders who are also trustworthy.

  1. Relatively Big Time and Money Commitment

By now it’s probably clear that real estate is not for the half-hearted.  You will need money upfront (forget those sketchy “no money down” strategies), and for what you don’t have on hand you will need loans.  This means taking a risk and investing some of your time in order to come out ahead.

If you outsource other people to renovate or maintain your property you will accrue additional costs.  If you decide to take on some of the work yourself, you will accrue additional time.  These time and money sacrifices are temporary as your investment becomes profitable, but in the meantime it will take a definite amount of discipline and strategizing.  


I’ve done my best to be fair about the pros and cons of each of these types of investing and hopefully it’s helped you get a clearer perspective.

If you have the money and the time, it’s my personal, experience-based opinion that real estate investing is the way to go.  You may have to put in a bit more time and money upfront, but it will generally pay off faster and bigger if you keep a good head on your shoulders and know what you’re doing.

But real estate investing is a lot of work and it certainly doesn’t fit everyone’s lifestyle.  The stock market is still a great opportunity to make your money go further, and for some people, it’s the more logical choice.

The Mindset Of A Real Estate Investor

When you’re first learning about real estate investing, it’s easy to Google certain specific questions like “do I need a realtor-broker?” to get a direct answer. 

But what about the more psychological and yet (in my opinion) important question of, what kind of a person do I need to be to succeed at real estate investing?  

Can I really do it – can anyone do it?

Of course, this question could easily spawn a whole book.  But I don’t believe that aspiring real estate investors need to sweat this too much, nor should they have to wade through a ton of complicated philosophizing.

Based on my own personal experience and observations, I’ve distilled the answer to this question down into 6 basic points that I’ll cover in this blog post.  Here’s the shortlist upfront (note it’s nothing too surprising or controversial):

1. Patience

2. A Sense of Humor

3. Social skills

4. Self-Discipline

5. Introspection

6. An interest in lifelong learning 

1. Patience

“I thought I was a patient person until…”  is a phrase you’ve probably heard from one friend or another over the years.  “I thought I was a patient person until I got married.”  “I thought I was a patient person until I had kids.”

Well, let me add to those sentiments:  I thought I was a patient person until I started investing in real estate.

Now, nobody has perfect patience, including you and me, and that’s 100% okay.  We all improve over time since experience is the best teacher.  

Here’s what I mean by “patience” when it comes to real estate investing:

Things don’t happen quickly in the real estate world.  Properties take time to finance and purchase, they take time to renovate and maintain, and they take time to sell.  Many people and factors are involved; not everything is under your control.   You can’t predict what the home inspector or the plumber, or the new tenant, or the real estate agent are going to tell you or how they’re going to behave.  More often than not, an unexpected mystery leak or other issue will rear its head, throwing your perfect plans off course.

So the real question is: can you take all of this in stride and have realistic expectations?

In fact, I would add to the virtue of patience the virtue of resilience.  Are you good with handling multiple variables, uncertain time frames and people who are sometimes not dependable?  Can you take things in stride?  If so, you’re well on your way to being cut out for real estate investing.

2. A Sense of Humor

A sense of humor goes along with patience and resilience – I see it as another aspect of a broader mentality.

It’s so much easier to get through life – and real estate investing – when you’re able to look back and laugh at the dumb mistakes you’ve made.  It’s an even bigger bonus when you’re able to laugh, or at least have a lighthearted perspective, in the moment that the difficulty is occurring.

Having a sense of humor doesn’t mean being flippant.  You can be serious and responsible about your investment while at the same time not wasting your emotions on things that don’t matter (like the fact that the tenant you’re about to evict hates your guts, even though you gave her a second chance and she blew it).  

A sense of humor helps you detach and at the same time, see people from a kinder perspective.  “Maybe she was just having a bad day, and I had comically bad timing when I came to talk to her” – it’s this kind of perspective that can turn a bad day into an opportunity to reflect and deflect.

3. Social Skills

“But I’m not a people person!”

I’m not saying you have to love everyone you meet on this crazy planet we call Earth, but it sure helps when you are open to meeting and interacting with people on a regular basis, and have the basic skills to understand and communicate with those people effectively.

When I was sixteen years old I worked in an ice cream parlor.  As anyone who’s ever worked in customer service knows, there are all kinds of people who come through that door and some of them aren’t easy to deal with.  

For me, it was a priceless learning experience.  I soon understood that there were all types of people out there, some very pleasant while others were grumpy no matter how perfectly I scooped their ice cream for them.  I learned to observe and understand human nature and take things in stride, and I was able to apply that knowledge later on in real estate.

Think of all the people who are involved in the transaction of a property: the buyer, the seller, the real estate agents, the home inspector, bankers…

And that’s nothing compared to how many people you’ll meet when you are a full-fledged rental business: tenants obviously have a higher turnover rate than owners, so you’ll be meeting all kinds of new and interesting folks.  And don’t forget you’ll need to establish relationships with subcontractors, accountants and attorneys as well.

Your goal is not to be best friends with everyone you meet, nor to be the most charming person imaginable.  What you need are basic active listening skills, the ability to understand where the other person is coming from, and the ability to be pleasant and in control of your attitude.

Would you want to do business with a grump, or someone who is socially awkward?  Now is the time to reevaluate your own persona and make sure you are someone who is approachable and generally nice to be around.  It will take you far.

4. Self-Discipline

At first, this one might seem obvious: “of course real estate takes time and sacrifice, why would I get into it if I didn’t know that!”

I’ll tell you why: because people tend not to think in concrete terms about just what they will need to sacrifice to be successful, especially in the long run; and real estate is a long game.

Time is a precious commodity and each minute that passes is gone for good.  Think for a moment about what the minutes in your day add up to: do they add up to you honing and improving a skill, or do they add up to your Netflix “watched” list expanding?

Investing in real estate requires a lot, especially up front.  You will need to go the extra mile with doing your research and gaining vital skills to pave a solid foundation for years to come.

In my early investing years, I watched very little TV and spent most of my “free time” doing maintenance on my properties.  It wasn’t a cycle I or anyone could sustain forever.  But I eventually reached the point where my business became profitable and today I have both time and money to do whatever I want, within reason.

In other words: those few years of hard work and no TV allowed me to be in the position I am today.

So think about that the next time you find yourself unwinding with your phone or favorite show: is this something you’re willing to give up or cut back on for a few years of hard work? Would you rather have more free time and less money now, or work like heck so you can have more money and free time later? It’s a choice you need to consciously think about.

You definitely can and should still have some downtime for yourself.  But the important question is, are you ready to give up certain comforts in your lifestyle now to be successful at the long game of real estate investing?

There is always going to be a sacrifice involved.  You can sacrifice time and energy now for money and more free time later, or sacrifice future benefits by being more comfortable now.

There’s nothing wrong with the latter approach.  Some people prefer to have an easier lifestyle now, even if it means less flexibility and success in the future.  The real question is, which type of person are you?  You can’t choose whether you will sacrifice something, but you can choose what it is that you will sacrifice.

5. Intentional Living

Do you feel comfortable taking a moment alone with yourself to reflect on how you did this week, last week, or this past year?  

Intentional living means you are comfortable reflecting and reevaluating your choices on a weekly basis.  It also means you have goals for the future and are actively working towards those goals, and are flexible enough to change what you are doing in order to get there.

Some people keep their days so busy and full that they have almost no time to reflect or plan long-term.  Some people definitely aren’t as comfortable thinking about their choices, successes and failures; they prefer to live “in the moment” all the time.

It’s great to stay grounded in the present.  But if you aren’t comfortable reevaluating your choices and your priorities and taking responsibility for them, then real estate investing may not be the best route for you.  

Real estate is not for the faint of heart; you are bound to make mistakes and have setbacks.  A sense of humility and a willingness to learn about what you did — and about yourself — is crucial to finding success in the long term.  Being successful at real estate also means thinking in terms of years or even decades, not weeks or months.

Time goes by whether you like it or not.  But one thing you are able to control is making sure you plan and schedule your time now so that you will end up where you want to be.  It’s not a “set it and forget it” process either; you are constantly learning, adapting and growing.  

6. An Interest in Lifelong Learning

The best in any field enjoy what they do.  This drives them to learn more and become even better.  It’s a positive cycle.

The great news is that there are more amazing, high-quality resources available now than ever before, and many of them are free.  The Internet is full of blogs, courses, webinars and other content pulled from the rich experience of people who have gone before you.  A simple Google search will yield more information than you could ever hope to get through.

There are also excellent books written by established experts you can buy or download or borrow.  If you don’t have time to read a few minutes before bed every night, you can listen to an audiobook while driving in the car.  

Finally, perhaps the best and most meaningful way to learn and progress in the real estate world is to find a trusted mentor.  This may be a friend you know who’s been doing real estate for a while, a speaker at a real estate seminar, someone you discover word-of-mouth or even someone you meet online.  Whatever the case, look for someone who has proven experience but also wisdom and a sense of humility (and ideally, a sense of humor).  It will truly enrich your real estate journey.


These six qualities are not the only things that count when it comes to finding success in the world of real estate investing. But they are an important start to knowing if real estate is the right path for you to begin with.  

You don’t need to be perfect or even great at all of these qualities (I wasn’t in the beginning and I’m still learning now).  What matters is that you see the value in these mindsets and take the initiative in implementing them in your own life.  If you do, I can tell you from personal experience that it will benefit you not only in your real estate career but in every aspect of your life.