Real Estate Investing is Unlike Any Other Job: Here Are the Upsides & Downsides

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We all grew up — well, most of us — being taught that we had to get the “A” in school or we had to always do our best or we had to act a certain way to be considered “successful.” Most career paths or industries we get into have only further supported these expectations. If you don’t make the grades, you don’t get the job. If you fail at your work tasks, you get written up or lose your job. If you act inappropriately, you are likely to get fired. All of those beliefs we grew up with only get more deeply embedded within us the further we move along our paths in life.

Until now. Welcome to real estate investing, the land where most of the rules we have known and (not) loved go right out the window.

Real estate investing really does go outside the box when it comes to a lot of things we’ve been taught to believe.

If you are a real estate investor:

  • It doesn’t matter if you failed every class you ever took, or even if you have a high school diploma or not. You can still be a real estate investor (and successful one at that).
  • You are working for yourself so all of those threats of being fired or assumptions about how you have to act are gone because you can’t get fired (unless you fire yourself).
  • You can be a raging jackass and still run a profitable real estate business (not my preferred route for people to take, but it can be done).
  • Very few of the fundamentals of real estate investing were ever taught in schools, so everyone is on their own for figuring it all out (unless you have a family member or someone who is already in the industry and you’ve learned by watching them).

For you folks on the more rebellious side of life, your ears may have just perked up and you may be feeling all sorts of fired up about getting into real estate investing now! If you err on the more cautious side of life, hearing all of that may have sparked your nerves a little in thinking of getting into real estate investing.

No matter which side of the spectrum you are on, you can still get into real estate investing.

Real estate investing is a very different field than most career paths you can choose, mostly for the reasons already mentioned. It’s a different feel of an industry, and it has different expectations and “rules” than most. Now that you understand how different of an industry it really is, let’s look at the pros and cons of being in real estate investing as compared to other industries.

I’m going to start with the downsides (cons) of the industry first, so we can end on a good note with upsides (pros).

Downsides to Real Estate Investing

I’ve already briefly hit on the biggest downsides, but I’ll elaborate more here. And keep in mind too that all of these downsides, depending on your preferences and styles, don’t necessarily have to be seen only as downsides. Some people actually like these things about real estate investing!

But in staying on a more factual side, I say these as downsides mostly because they do in fact make real estate investing difficult. It’s that challenge that a lot of people see as a good thing in certain areas, but for now we’ll keep these things listed as bummers to the industry.

There’s No Specified Education

This is really the biggest issue with real estate investing in my mind. We just weren’t taught this stuff in school! I know there are real estate degrees offered in some colleges, and certainly you can always get a more generic financial background in school that can be applied to investing, but straight real estate investing principles are not taught in any school I’ve ever heard of. Why do you think the guru programs can make so much money?

If there were college degrees specific to this stuff, you could spend the same money or less than you would at a guru program just getting a college degree that teaches what you need to know. So to get into this industry, you really have to exercise serious initiative to get yourself educated. And to make that harder, there are SO many resources out there now that it can really get overwhelming and confusing trying to figure out who or what to rely on for your education. The overwhelming plethora of information out there is great for access to resources, but figuring out who to listen to is tricky sometimes.

There’s a Lack of Standardization

There are few standards that must be maintained in this industry. It really does feel like a free-for-all sometimes because everyone is just doing their own thing, it’s often very difficult to know if who you are working with is legit, and there is no set process anyone has to follow to do anything, really, so everything can become very confusing very fast.

Related: 5 Harsh Realities About Real Estate Investing Every Newbie Should Know

Risk is a Given

Guess what? Real estate can be a risky business. There are no guarantees in this industry, there are a gazillion ways to fail, and it can prove to be a painful road. One commonality amongst every successful real estate investor I’ve ever read about is that they have failed miserably and to the tunes of a LOT of money, but they did not stop once they failed. Failure in this industry is almost like a rite of passage to make it big!

Sure, you don’t necessarily have to plan to become a billionaire with real estate, and therefore you won’t be required to make that big of mistakes, but it goes to show that failure and mistakes are a big part of this industry. You have to be mentally ready for that! Nothing is guaranteed, and nothing is perfect. (Note: there are certainly ways to help mitigate risk once you dive into this industry and hopefully allow you to avoid the bigger-level mistakes, so be sure to get educated on any avenue you choose to pursue!)

You Might Deal With Unsavory People

It’s just reality—there are some raging jackasses in real estate! There have also been scammers. The jackasses stem from the ability to be anyone you want in this industry with little chance of punishment (worst case is usually just some lost business). The scammers stem, I think, from the fact that everyone is on their own to get educated in this industry, and therefore that leaves a wide-open door for anyone to step in and claim they know everything, and then take you for a ton of money because you have no way of knowing otherwise. Real estate is definitely not for the faint of heart when it comes to dealing with the people, but certainly there are a lot of nice folks out there too that you can get connected with. Just be on alert for the people you likely don’t want to do business with.

Upsides to Real Estate Investing

I can hear all of you rebels getting all fired up after reading those downsides because of the inherent challenge that each of those poses to an investor! Anyone who likes problem solving, dealing with people of all types, being on their own, and taking risks will love real estate investing! All of those downsides really can be turned into good things, but they do make investing harder, regardless of how much they might excite you.

Now let’s focus on the perks to this industry that you might not find in most other career paths. And, for those of you who aren’t adventure-seeking risk hounds, hopefully these will make you feel better about real estate investing and you’ll be encouraged to get into it regardless of the downsides.

There’s a Chance of Huge Rewards

Where there is risk, there are rewards. And the rewards, mostly financial, of real estate investing can be huge. And better yet, you control how big of rewards you reap! It’s not like a salaried job where you are capped at your max salary—when you are investing you can just keep going until you hit whatever goal or level you want to! The power is in your hands and there is no cap to what you can achieve. Few other industries, in my opinion, offer that.

It Offers Flexibility

Man does this word go a long ways with real estate investing. You have flexibility in everything ranging from what kind of investing you do (tons of options), to what schedule you do it on, to where you do it, to how long you do it, to how much money you make doing it, to the people you work with doing it, and you are your own boss! This kind of flexibility, in all of these areas, is pretty hard to find in most other industries.

You Get to Be Yourself

This happens in a couple of ways. For one, you really can be you (even if you are that naturally raging jackass!) and not have to conform to anyone else’s standards. I don’t see this as a free pass for being a jerk, and being a jerk really isn’t what I’m focusing on here, but rather — if you are shy you can remain shy and quiet, if you are an aggressive person you can be aggressive, if you are hilarious you can woo people with your humor… the list is endless! You don’t have to mute anything about you like you often would have to in corporate-type jobs or wherever else you might work.

Related: Not Easy, But Worth it: The Top 7 Sacrifices Real Estate Investing Demands

The other thing about being yourself in this industry is that there are so many options for how you invest in real estate; you can really tailor what you do to be not only something you truly enjoy, but also something you are really good at. It’s kind of like rugby — whatever your strength is, there is a position on the field for you (at least if you are playing 15s!). You don’t have to be good at swinging a hammer or negotiating deals to be in real estate. There is everything from sales to marketing to online relationships to paperwork to people skills or contracts to anything! Or maybe you do like swinging hammers — then there is definitely room for that, too. No matter what your skill, there is something in real estate you can do with it.

You’ll Meet Some Pretty Great People, Too

This one deserves to be in both categories because while there are some jerks out there that you are likely to run into, I’ve also met some of the coolest people I’ve ever known through real estate investing. As soon as you have a common interest with a group of people, such as financial freedom, that puts you amongst like-minded people to a degree that you wouldn’t always meet elsewhere. There are some smart and fun folks in this industry!

It Allows You to Embrace Failure

It IS an option! And not only is it an option, it’s a sign of impending success. There is no room in this industry for expecting perfection. Maybe someone every now and then breezes through without making any big mistakes, but it’s certainly not the majority of us. When failure is an option, it takes so much pressure off!

Being able to look at any mistakes or failures as a good thing, rather than a bad or job-threatening thing, adds years to your life and is just a more enjoyable way to live. How many industries do you know allow so much freedom in the failure department?

What do you think? Is real estate investing as different from most other industries as I think it is? What are your opinions on the biggest pros and cons to real estate investing?

I want to hear your stories!

About Author

Ali Boone

Ali Boone is a lifestyle entrepreneur, business consultant, and real estate investor. Ali left her corporate job as an Aerospace Engineer to follow her passion for being her own boss and creating true lifestyle design. She did this through real estate investing, using primarily creative financing to purchase five properties in her first 18 months of investing. Ali’s real estate portfolio started with pre-construction investments in Nicaragua and then moved towards turnkey rental properties in various markets throughout the U.S. With this success, she went on to create her company Hipster Investments, which focuses on turnkey rental properties and offers hands-on support for new investors and those going through the investing process. She’s written nearly 200 articles for BiggerPockets and has been featured in Fox Business, The Motley Fool, and Personal Real Estate Investor Magazine. She still owns her first turnkey rental properties and is a co-owner and the landlord of property local to her in Venice Beach.


  1. Hi Ali,
    I am using this space to answer a question a question you asked me on your insurance article.
    A lot of times insurance is, if not required, smart to have in your whatever can go wrong will go wrong and whatever can’t possibly happen just might kit for animals.
    People generally don’t use common sense around simple minded animals. Only one example, I promise, an animal can’t remember tomorrow why you were mad at it yesterday. They just don’t have that lobe of their brain so they probably will view you as unstable if you do hold a grudge. They are however crafty enough to be trained that if things repeatedly turn out the same and it isn’t what they want they will change what they are doing in hopes of a more favorable result. It all depends on who is running point for them how these changes will be viewed.
    I for whatever reason kept getting the problem kids of the animal world. Everyone has heard the term ALPHA by now. So here’s the thing, people usually try to solve problems with an alpha animal by over powering the animal, might be alright with a puppy if you don’t want a good dog. Few people who think they do really have an alpha, who would answer aggression with aggression. To wrap this up, that is one reason to have insurance on an animal/ to PROTECT it from people.
    The other much simpler, it is either genetically superior or has skills of some kind that set it apart from all the others. It is however hard to place value on an animal without past performances or cash winnings to draw an estimated potential value from. To wrap this up but support your today article a little/ A perfect performer or perfectly engineered animal is called a freak by those who truly love it and not to be expected very often.
    On that note, remember, you asked, and don’t worry I make tons of mistakes, MAYBE I’LL LEARN !?!?

  2. True, RE Investing is unlike any other job one works..That’s because said jobs are, depending on what you do, actually FUN…lol If flipping and/or rehabbing was as much fun as playing music, I’d be all over it…My hats off to the people who can do it though….I’m just not a masochist

    • Ali Boone

      I’m not either, Jorge. That’s why I buy properties that need no work whatsoever, a manager manages, and all I need to do is approve or deny a maintenance fix (verbal only, the fix happens by someone else). I have ZERO desire to do any of the rest of it, or flip, or rehab, or anything that requires my time or effort. 🙂

  3. David Semer

    This is great article. I really liked the way you broke it out with all the different people and backgrounds you never know who will help you or even educate and mentor you from time to time. One of the things I enjoyed the most about meeting local investors is everybody business model is different.(some flipper/ buy and hold/ commercial space/ note buyers/wholesalers…) Each have different goals they are trying to accomplish. Even though some part of the business may compete with each other in the end you probably will make more money knowing how to help each other out. Sometime a deal that does not make sense to you will fit for them and vice verse. Keep sharing outside the box thoughts.

  4. Rick Hamrick

    Love your posts, Ali. You have an amazing way of presenting topics in creative and thought-provoking ways.

    As a retired 9-5’er now using designated retirement funds for passive and casual real estate investing, I must admit yours, and the many other well-written posts on BP would have inspired me to take a more active investing role 20-25 years ago. Who wooda known?

    Now, I get deferred and vicarious gratification – along with excellent ROI – from watching our son build the family real estate empire.

    Keep the posts coming, young lady.

  5. Sharon Vornholt

    Hey Ali –

    Another great post. This really speaks to both the pros and cons of this business we love so much. I really believe that if folks go into this business with a clear understanding of the risks and rewards they stand a much better chance of being successful.

    I love the flexibility of this business. Now if I could just find balance like you have. 🙂


    • Ali Boone

      Haha…then we could be travel buddies Sharon! Make sure your biz is 100% online and then you can be like me and just carry your laptop to wherever you want to go!

      And yes, I totally agree about being educated going into it and that increasing the chances of success, for sure. Add a little drive to that (to get past the headaches) and you’re a shoe-in!

  6. Great post i could not have said it better myself. After many years in this industry I can say i have achieved financial freedom. The best point of this post is the fact that success in Real Estate Investing does not depend on any particular skill set, besides the willingness to take on risk and work hard. There are so many areas to this industry that a hard working risk orientated person can succeed in. One more characteristic is a willingness and ability to learn, this industry changes and there is lots of new information.

  7. Great points Ali!

    I definitely agree with you, real estate is unlike any other field!

    Looking back, it’s been a roller coaster — never a dull moment. Though I do have my good days and bad days, what I enjoy about real estate are the stories. With so many different experiences, the stories are what makes me stay in the game.

    At the end of the day, I can honestly say I definitely enjoy what I do!

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