Personal Development

3 Examples of Why Workaholic Real Estate Investors Have It All Wrong

Expertise: Personal Finance
13 Articles Written
Drowning victims, Hand of drowning man needing help. Failure and rescue concept.

There are numerous kinds of real estate investors that explore the BiggerPockets universe, but we all have one thing in common: We aim to improve our lives with passive income. We have different paths and varied goals, but I would guess that we are all striving to find more happiness through REI.

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As the new year approaches, it’s a great time to ask ourselves, “Why am I doing this?”

I have recently discovered this is something I need to ask myself more often. My wife and I have discussed our “why” over and over, but we’ve never actually written it down. (Big mistake.) In short, our “why” is to have more time and freedom to enjoy life.

As my wife and I have continued our journey of real estate investing and building our portfolio, we have struggled with staying true to our “why” more than once.

In the beginning, we each had full-time jobs. A year ago, my wife was able to go half-time at her career due to our accumulating monthly passive income. This plan included her devoting those newly freed hours to expanding our REI portfolio with more properties. The time dedicated to this endeavor quickly required more than the four hours freed from her primary job.

Frustrated student behind the desk keeping hands on face

In short, it’s been an exhausting and trying year. We’ve both been extremely busy with jobs and real estate. Our “why” has all but disappeared from our daily thoughts. We have found ourselves struggling to allocate time to enjoy life in our dedicated progression of building our portfolio.

Here are three wake-up calls that have recently shaken up my world and helped me refocus my choices to harmoniously combine our “why” with our efforts to grow our passive income streams.

Related: 4 Reasons Your New Year’s Resolutions Will Crash and Burn (& How to Change That)

3 Eye-Opening Revelations About Workaholism

#1. Sam Walton

I recently learned that the famous entrepreneur and founder of Walmart had some insightful last words:

“I blew it.”

In his lifetime, he has acquired fame, fortune, and a retail empire to pass along to his children. But in his last days, he realized it had come at an unfortunate price. He had given up time with the people he cared about the most: his wife, children, and friends.

People widely view Sam Walton as an enormous success. And most would unquestionably agree that his success came with a workaholic mentality and an undying commitment to his business.

But I feel if he could give me one piece of advice today, he would tell me that none of his work accomplishments were worth the time he lost with his family.

I hear you, Sam. Loud and clear.

#2. An Innocent Question

Last month, I had a conversation with a friend about real estate investing. He is not an investor but is curious.

He asked me, “What is your end goal?”

The motivation for this question, I assume, was his observation that my life seemed crazy-busy. I responded to his inquisition with the “why” my wife and I had discussed: “We want to build up our passive income, so we have more time to enjoy the things that make us happy.”

Then he asked me, “But what about now? It seems like you two don’t have much free time at all.”

And he was dead right. Point taken, my friend, and thanks for the observation.

#3. Setting Goals for the New Year

While setting some goals for 2020, we found ourselves writing things like this:

  1. Add 10 more units to our portfolio.
  2. Increase our passive income by 200%.
  3. Complete four more BRRRRs.

The list continued with goals around money, net worth, and accomplishments.


Then, I had a flashback to Your Money or Your Life. The central premise of that amazing book is that our time is our most valuable asset. Anything we do should be contemplated, analyzed, and chosen based on the goal of taking full advantage of our time, since we only have so much. Not to mention, we are not told how much that is.

For my wife and me, we are most happy when we are spending time with each other, spending time with our friends or family, traveling, and relaxing. But we have recently found ourselves going down the rabbit hole of real estate investing to the point that our free time has all but vanished for most of the last six months.

We thought, “If we give up our time and our happiness in pursuit of our happiness, is it really worth it?”

Time for some new goals.

Related: Why I Set Highly Ambitious Goals for My Real Estate Business (& Why You Should, Too)

New Goals for the New Year

Here they are:

  1. Spend six hours a week enjoying each other’s company.
  2. Meet with friends or family twice a week for coffee or a meal.
  3. Spend five hours a week relaxing, meditating, or having quality “alone” time.
  4. Exercise five times a week.
  5. After goals 1 through 4 are met, spend any remaining time building our REI portfolio.

I’m looking forward to more happiness, connection, and contemplation in 2020. I’m also sure we will add more properties and increase our passive income along the way, but not in a manner that forces our happiness to take a back seat.

Our “why” is now written down, and our goals are aligned to bring us more joy in the present. Our main objective is to not “blow it” in 2020. Thanks for the clarity, Sam.

What are your goals for the New Year?

Share them to hold yourself accountable below!

Dan is a high school Business/Marketing teacher, real estate investor, and personal finance advocate in Denver, Colorado. He and his wife have a variety of real estate investments including multifa...
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    Dave Foster Qualified Intermediary for 1031 Exchanges from St. Petersburg, FL
    Replied 3 months ago
    Well Said Dan!!!
    Norwin Lanot
    Replied 3 months ago
    Dan, great insight!
    Rob Cook Real Estate Entrepreneur & Coach from Powell, Wyoming
    Replied 3 months ago
    Dan, outstanding reminder. I am going thru this type transformation now, and have been for a year or two. I am turning 61, so it is even more relevant and pressing in my case (how much good time do I have left?). I had the opportunity to "retire" at age 39 due to owning a successful construction business and accomplishing handing it off completely to a trusted employee/partner. But that was the BEGINNING of my learning what retirement and freedom is all about. 20 years later I am still learning! But making progress now thanks to reminders like your piece here, and many books like 4 Hour Work Week, and I just obtained Your Money or Your Life due to your mention here! What has complicated my story and life path/journey, is that I LOVE working! And particularly doing realty deals for myself and physically performing all the maintenance and renovation on my own properties. So I am caught in a vicious cycle(s) of "trying" to slow down and play more, but constantly getting sucked back into work by irresistible deals that come my way! I have almost 60 cash-flowing rental units, and half are owned free and clear, and have nearly $1 Mil cash in the bank - so I do not need more money or income. BUT, when a deal comes to me, which it does about twice a year minimum, that I can make $100K to $300K on instantly, I am not strong enough or arrogant enough or rich enough to say NO. But, this is being reactionary, which of course, will never end if I do not make significant changes in my mindset and my actions. I am healthy, happily married for 39 years, my kids are all successful and married and have grandchildren for us and we all are very close. I have a lot of time on my hands now. SO, I have no excuse other than 1) inertia and 2) greed. My challenge is to actively STOP doing what comes easily to me - more real estate deals. I am structurally changing my life to create space (time slots) and a routine(s) to schedule in all the non-money making things like play, exercise, quiet time, social and such activities. As you mentioned, if you do not schedule in the "soft" tasks and activities, they will continually get squeezed out. This apparently will never end for me, organically. So I have to forcefully force the change. It is working. Yesterday, I was bored. This is relatively new to me, having always quickly filled any such voids with ever more business activities in the past. I never had a chance to smell the roses and allocate my time to the less demanding tasks - what you identified correctly as the MOST important ones - family, social, play etc. To summarize, for those who are lazy or do not enjoy work, it is easier to get the mindset part right to allow time and space for the important non-financial things in life. It is much harder for a lifetime hard charging, money-motivated entrepreneur like me. BUT, that does not relieve me of the responsibility to do so, if I want to have a more fulfilling life. Of course, it is also easier to accomplish a slow down when you are already financially independent! So there is that conflict for younger people to actually accomplish what you are referring to, without suffering financially (being a "bum" instead of earning money and wealth, etc.). That said, there is a new awareness of the importance, potential and value of creating a Financial Independence (FI) lifestyle early on, by design. I am intrigued, impressed and even envious of this FI movement, and understand that many accomplish this before 30. We will see how that plays out over time, but it all makes sense, IF they can pull it off. This boils down to defining how much money/income one needs, and then working towards that as the goal, instead of just the "More, More, More" Wall Street mentality which never ends or concludes - there is no destination called "More." Time Wealth is the new paradigm which was not really emphasized in my formative years. I always learned to measure my financial success by the Net Worth scoreboard. Money at any cost/price, is stupid and carried to the extreme results in unhappiness if not prison sentences. Thanks for the reminder!
    Dan Sheeks Rental Property Investor from Denver, CO
    Replied 3 months ago
    Hi Rob. Thanks for your reply! I agree with a lot of what you said. Best of luck to you in the new year.
    Adrian Ayub
    Replied 3 months ago
    Hey, Dan, I'm so happy that you were able to time block for friends and family. I really don't ever see my parents or former friends and I just justify it with the hopes that things will turn out right in the end. I think making time for other things will be my main resolution this year. Thanks.
    Dan Sheeks Rental Property Investor from Denver, CO
    Replied 3 months ago
    Hey Adrian. Thanks for your comment and best of luck in 2020!
    Nathan G. Real Estate Broker from Cody, WY
    Replied 3 months ago
    Many of us suffer from this. I'm better than I was 10 years ago and I'm striving to get better. One of my favorite stories: An American investment banker was at the pier of a small coastal Mexican village when a small boat with just one fisherman docked. Inside the small boat were several large yellowfin tuna. The American complimented the Mexican on the quality of his fish and asked how long it took to catch them. The Mexican replied, “only a little while. The American then asked why didn’t he stay out longer and catch more fish? The Mexican said he had enough to support his family’s immediate needs. The American then asked, “but what do you do with the rest of your time?” The Mexican fisherman said, “I sleep late, fish a little, play with my children, take siestas with my wife, Maria, stroll into the village each evening where I sip wine, and play guitar with my amigos. I have a full and busy life.” The American scoffed, “I am a Harvard MBA and could help you. You should spend more time fishing and with the proceeds, buy a bigger boat. With the proceeds from the bigger boat, you could buy several boats, eventually you would have a fleet of fishing boats. Instead of selling your catch to a middleman you would sell directly to the processor, eventually opening your own cannery. You would control the product, processing, and distribution. You would need to leave this small coastal fishing village and move to Mexico City, then LA and eventually New York City, where you will run your expanding enterprise.” The Mexican fisherman asked, “But, how long will this all take?” To which the American replied, “15 – 20 years.” “But what then?” Asked the Mexican. The American laughed and said, “That’s the best part. When the time is right you would announce an IPO and sell your company stock to the public and become very rich, you would make millions!” “Millions – then what?” The American said, “Then you would retire. Move to a small coastal fishing village where you would sleep late, fish a little, play with your kids, take siestas with your wife, stroll to the village in the evenings where you could sip wine and play your guitar with your amigos
    Dan Sheeks Rental Property Investor from Denver, CO
    Replied 3 months ago
    I love this story, Nathan! Thanks for posting it.
    Nicole Flakes Investor from Houston, Texas
    Replied 3 months ago
    Love this! Thanks for sharing.
    Cynthia Gillespie Investor from Seabrook, Texas
    Replied 3 months ago
    I totally agreed with your overall position of spending time"now" with the people you love and doing things you enjoy, but 6 hours a week didn't sound like nearly enough quality time to spend with your partner. That's less than an hour a day!! Sounds to me you will still be a workaholic in 2020. But if that's what works for you and your spouse, so be it. 👍
    Dan Sheeks Rental Property Investor from Denver, CO
    Replied 3 months ago
    Hi, Cynthia. Thanks for your comment. Just to clarify, the goals I have are minimums. As you know, some weeks are busier than others. But even during the busiest weeks, I hope to meet my goals. Other weeks I will surpass those minimums with ease. Best of luck to you in 2020!
    Joe Homs Flipper from Mission Viejo, CA
    Replied 3 months ago
    Dan, Looks like you are very young from your picture, but at 65 I look at things differently. However, I do like where your going and what you said. Here are my new years resolutions: New Goals for the New Year Here they are: 1. Spend six hours a week enjoying each other’s company. (I like going to the Movies three times a week. That's at least 6 hours, plus dining out everyday as well.) 2. Meet with friends or family twice a week for coffee or a meal. (I meet with biggerpockets members in my area one to one having coffee and lunch. We discuss how they can get started in investing.) 3. Spend five hours a week relaxing, meditating, or having quality “alone” time. (Sorry to me this is like a retirement commercial for a financial company that has me lying on the beach with my wife. I find myself bored and wanting to do something useful with my time. We have so little of it.) 4. Exercise five times a week. (I actually try to exercise 7 days a week if I can.) 5. After goals 1 through 4 are met, spend any remaining time building our REI portfolio. (I do this everyday of my life. My focus now is more on educating and mentoring young people and planning for my grandchildren. Also what you left out "For Me" is that I am a workaholic, but its really not work for me. I feel like it's a vacation day for me everyday. Who do I invite to spend my vacation day with me today. Great article and great points. Thanks for sharing. Good Investing...
    Dan Sheeks Rental Property Investor from Denver, CO
    Replied 3 months ago
    Hi, Joe. Thanks for your comment. I like your goals! Best of luck in 2020!
    Marcus Roberson Rental Property Investor from Denver CO
    Replied 3 months ago
    Absolutely love this! Really drives home what's most important!
    Yulaw Jackson
    Replied 3 months ago
    The hours that you carve out for quality time, how are you tracking those? It's spread across a few days where some days you might not get any in.
    Dan Sheeks Rental Property Investor from Denver, CO
    Replied 3 months ago
    Thanks for your question, Yulaw. I'll be tracking the hours spent on each activity daily. But I will not be obsessive about it. For instance, I will not be counting each and every minute, but rounding to the nearest half hour. I don't want to waste quality time tracking every minute of my day as that would be counter-productive to my goals of enjoying life more. :-)
    LaTisha Frazier
    Replied 3 months ago
    I enjoyed this post. I see family members that are just as busy as you and your wife. I often think that I don’t want this business to consume my life , but I also want to excel in it. Finding balance is the key. Thanks for reminding me to stay focused on my WHY.