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

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

4 min read
Dan Sheeks

Dan Sheeks is a high school Business/Marketing teacher, real estate investor, and personal finance advocate in Denver, Colo. In his 16-plus years of teaching high school, he has taught a variety of business subjects including financial literacy, entrepreneurship, and marketing.

Dan’s passions include working with teenagers, advocating for personal finance education, investing in real estate, and promoting the FIRE movement. Embedded in his classes is the co-curricular DECA club in which students travel, compete, acquire leadership skills, do community service, and have fun! His students have competed at the national level in entrepreneurship, personal finance, marketing, and hospitality services with much success over the years.

Dan volunteers in the MoneyWi$er initiative out of the Colorado Attorney General’s Office with a few other hand-picked experts from around the state. The program strives to advance financial literacy in Colorado secondary education. Dan has also taken his high school students into local middle and elementary schools, where his students have taught the importance of personal finance to younger children.

Launched in late 2019, SheeksFreaks is a blog and Instagram page that are dedicated to helping young people learn money management skills, start investing in real estate, and pursue financial independence. The SheeksFreaks blog aims to help teens use specific methods of saving, earning extra income, and investing to set them on a track to purchase real estate investment properties in their early 20s and achieve financial independence at a young age.

Dan and his wife have a variety of real estate investments including multifamily, single family, Airbnb, and out-of-state BRRRRs. They currently have 14 units in the Denver metro area, Colorado Springs, and Detroit.

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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.

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.

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What are your goals for the New Year?

Share them to hold yourself accountable below!

Real estate investing can be fun but also overwhelming. As we enter the new year, what are some things we should keep in mind while we set goals for 2020? Here are some thoughts to consider before charging full speed ahead in your real estate investing endeavors.