5 Darker Aspects of Entrepreneurship You Need to Accept Before Taking the Plunge

by | BiggerPockets.com

There is a darker side of entrepreneurship that few talk about. Failure to recognize this can cause a lot of stress and life detours. Here are some of the things I’ve learned on my journey as a business owner and entrepreneur so far.

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5 Darker Aspects of Entrepreneurship You Need to Accept Before Taking the Plunge

If you earnestly throw yourself into active real estate investment or are launching your own business, you’ll soon encounter and realize the following.

1. It’s not glamorous.

It’s not all fame and glory, especially at the beginning. You’re often doing things you don’t want to do prior to being able to get someone else in there to take on those tasks. You’ll frequently find you are doing the same small, day-to-day tasks most of the time. Patience is the magic word.

2. You have to make sacrifices.

To find the time, funds, and traction you seek, you have to make sacrifices. You may have to give up a hobby to find the extra time. You may have to humble yourself to do tasks you normally wouldn’t dream of. You may have to cut back on what you spend until you turn a profit. With one of the first businesses I started, I actually had negative funds in my bank account. The bank provided a unofficial loan, which I paid back later, once I started bringing in profit.

Related: 10 Entrepreneurs Share Their Most Memorable Mentor-Taught Lessons

3. Everything is up to you.

If you want to drive your business, no one is going to hold your hand. It is simply up to you to make it happen. You have to figure it out. You have to stay self-reliant and get yourself up and maintain productivity, even on the darkest days. No one is going to do it for you. Try reading the poem by Ralph Waldo Emerson regarding self-reliance. It was an eye opener for me. For those who have never lived the entrepreneur life, this point can be very stressful, and this is often what leads people back to the corporate world. 

4. You must constantly get better.

Even once you think you’ve made it, if you decide to settle, then your fortunes may be reversed. You must constantly innovate and grow. With the way technology is constantly changing and with A.I. coming into the picture, staying ahead of the curve is very important.

5. You’ll likely take a pay cut.

If you are starting a new business it’s likely you’re going to take a pay cut. You may break even or lose money your first year in business.


Related: 6 Powerful Benefits of Quitting Your Job and Becoming an Entrepreneur

The Flip Side

Of course, some do make it. They make it really big after enduring certain phases of entrepreneurship.

The decision to embrace and work through the above challenges really comes down to what you’re looking to achieve. If you want to build something big, then you’re going to have to put in the work. If you want to build something that is a hobby or a side gig, then that’s different. Your goals will guide you—if you remember to revisit them every day.

It’s simply a matter of whether you are cut out for the entrepreneur life or not. As a youngster on the school scene, I thrived during the periods between classes. This is when I sold anything I could get my hands on to friends and fellow students. Entrepreneurship was always in my blood, but it still took work. This isn’t for everyone, just like being a professional basketball or tennis player isn’t for everyone. Even those with talent have to make the sacrifice to get to the next level and stay there.

We’re republishing this article to help out our newer readers.

What aspects of entrepreneurship worry you the most? If you’ve already taken the plunge towards working for yourself, what has surprised you?

Let me know with a comment!

About Author

Sterling White

With just under a decade of experience in the real estate industry, Sterling currently manages over $10MM in capital, which is deployed across a $26MM real estate portfolio made up of multifamily apartments and single-family homes. Through the company he co-founded, Holdfolio, he owns just under 400 units. Sterling was featured on the BiggerPockets Podcast and has been contributing content to BiggerPockets since 2014, with over 200 posts on topics ranging from single-family investing and apartment investing to wholesaling and scaling a business.


  1. Sonia Spangenberg

    Thanks Sterling for the reminder that this is all part of the process. Gosh this is so true. There have been dozens of times when I thought this is too hard. I do stay motivated because I’ve put so much time, money and stress into this that I don’t want to walk away anymore. It keeps me motivated to push ahead. I have new things to learn. I have to keep reminding myself of what I’ve gained in the process. Assets, (and debt), knowledge and self confidence have grown a bunch. Some successful people don’t share the hardships and make it look so easy. But reality is important to acknowledge. Success isn’t just wealth, and It just doesn’t happen overnight.

      • Sonia Spangenberg

        Sterling, thanks for asking. To be really honest, it is to listen to my gut more and not assume someone else who represents themselves as an expert, knows more. I being still a bit of a newbie, and in a partnership, was deferring to those near me, even if it differed from the broader messages I was getting from my courses and what I was reading, often on BP. I have become more aware of the value of my intuition borne out of education and gut. When looking back on multiple mistakes we made, my initial gut feeling was right. However, in an attempt to maintain peace in a partnership I deferred. Not any more. Also, I will now have more inner strength to hold others accountable for their side of the responsibilities from the beginning instead of letting it drag out. Moving forward…

  2. Susan Maneck

    You left out something. Health insurance! Obamacare was perfect for entrepreneurs just starting out, but what to do if it gets repealed? Thanks to my real estate investments over the last six years I’m now in the position to retire and go into this full-time, except for one thing. I need health insurance and I have too many pre-existing conditions to qualify for affordable health care without Obamacare. So I don’t dare retire until I know for sure what is going to happen to it.

  3. Deanna Opgenort

    If you are in CA look into Kaiser or other non-profit large HMOs — they have a more “member for life” philosophy. Once you are a member your fees are the same as everyone else in your age group, not based on what you personally have going on. I don’t know how their Obamacare-specific plans work, but it’s worth looking into.

  4. Erik Whiting

    Interesting piece, thanks for taking the time to write it.

    “Negative funds….unofficial loan” Is that a creative way of saying you bounced checks and ended up with an overdraft loan? Not criticizing, just never heard those terms used before and they sound like euphemisms. In an article designed to help folks understand the risks of entrepreneurship, I think we do them a better service to speak plainly rather than using ambiguous or “flowery” language. Just tell it like it is. Now if you situation was something else entirely, I’d be interested to know what you meant specifically.

    I’d say the last major dark aspect (and there are tons of minor ones!) is the failure rate. True businesses have a high fall out rate, and I imagine that for every millionaire cable TV real estate guru there are at least a thousand who tried it and burned out after 1-2 with little to show for it, and possibly piles of debt. I’m highly adverse of debt, but especially for folks who have never “been there, done that.” Too easy to make mistakes that are compounded by debt. Otherwise known as the dark side of leverage. It magnifies losses as well as profits. conventional guru wisdom is buy tons of property with no money down….then what happens when your tenant trashes the place and/or your 5-level deep wholesale /tenant/buyer lease option deal falls apart?

    It aint all beer and skittles, that’s for sure. Thank you for pointed that out. This is a good read for anyone thinking about getting into real estate. My encouragement would be to do it as a side gig for 1-2 years before jumping in whole hog and see if you’ve got the aptitude and the attitude. Maybe work nights and weekends helping out a property management agency or a local wholesaler for cash to save up and prepare to do your first deal.

    • It is good to know what is needed as I have had a few Businesses in the past it does take motivation
      and persistence on your part. I have found that in real estate it is a totally different beast you need to
      know a lot of things to start out but many people will not help you or give any real advise to beginners. I would like to start in real estate bit find it very hard to get any real world advise from people who are in this work it’s like their afraid you will take money from them very frustrating to
      find real advise that will help you get started. I;E All those fake seminars that cost thousands of dollars. If there is anyone on here who can give real world advise that work’s please let me know

  5. Karl B.

    The beautiful thing about real estate is that (unlike a lot of other ventures), when you get educated and follow the plan correctly you will likely experience success and your hard work with be tangible.

  6. Dmitriy Fomichenko

    Great post, Sterling!
    I agree with all of these points. There are a lot of things to be surprised at but the one that actually stood out for me was the amount of learning I have had. It could be something as simple attending customer calls every day, but every single call adds a new experience. You get to optimize the process and continue doing so.

    Your words on working continuously on repetitive things actually define what entrepreneurship is all about: Long consistent hours of hard work.

    Thanks for sharing!

  7. On my second week of full-time self-employment and it’s been amazing. The freedom involved in entrepreneurship is a great feeling. It’s been tough not to get overwhelmed with so much to do.

    Making a list the night before of 3 must do things the next day helps a ton.

    Great article and I read it at a perfect time. Now it’s time to keep grinding until we make it BIG.

  8. John Murray

    I’m a successful entrepreneur, from an early age I valued my independence. Freedom was my driver and never even considered failure as an option. Money was never an issue, I could always make money because I work hard at all endeavors. If money is your prime driver being an entrepreneur is not for you. You have to have passion, an independent spirit and fun loving freedom seeker. Multimillions will flow because it’s not work, it’s my passion and enjoyment. Employees have a difficult time with this concept, their paradigm is exchanging work for money. My paradigm is my work for my freedom, money is the windfall.

  9. Paul Moore

    Thanks for writing this, Sterling. Great read.

    I have been a serial entrepreneur for 24 years and I agree with John. I used to joke that “It’s great to be an entrepreneur… you have the freedom to work any 80 hours per week you choose!” But in my mid-50s, that is no longer fun. I am looking for freedom. An an opportunity to make an impact and give back.

  10. Bob Langworthy

    This is truth. I started an accounting practice 9 years ago with zero clients and having never prepared a single tax return. 9 years later I have two team members and we’ll serve close to 500 clients this year. In addition, I bought an office building to move my practice into. I have three tenants and am able to lease out some of the 20 parking spots.

    But my story starts in the depths of this article and a little deeper. Depression, discouragement, and self-doubt are a part of many entrepreneur’s journey.

    Blessings to you, Sterling, for another great post.

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