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The Downside of Entrepreneurship

Updated: Mar 5, 2021

This blog is written by Jen Josey, Real Estate Investor, and REIGN Coach. She is not a professional writer and writes like she talks so put your red pen away.  Jen is extremely opinionated but reserves the right to change her opinion at any time because, well, that's the way she rolls.  She may also use colorful language so don't be offended.  Jen does not claim to be an expert, she is just sharing her personal thoughts and adding a perspective on investor topics that may benefit her readers.  Jen also finds it strange to write in the third person.  Enjoy!

"Entrepreneurship is living a few years of your life like most people won't, so you can live the rest of your life like most people can't." -Anonymous

That is an anonymous quote I printed on card stock almost three years ago when my husband and I started our business. I made several copies and displayed them in a few different rooms in our house including opposite the toilet for maximum mental absorption. The one in the cover photo is at our kitchen sink and is the only one left, the others disappeared behind shelves, tossed accidentally into the garbage, or fell into drawers. As I washed my hands this morning looking at the water stains on the card stock, I re-read the statement and really took the time to reflect over its words.


I start with that first word, "entrepreneurship." I have a hard time spelling it (thank you autocorrect) much less calling myself one. I recently started seeing a new chiropractor and was stumped at the question, "What is your profession?" In my past life, it was a simple answer, "teacher" or "account manager." What was I supposed to put? I was wearing my workout clothes with last night's makeup and certainly didn't feel or look like an "entrepruh..." "entrepreh..." " owner." I wimped out and wrote, "house flipper." Heck, I thought it might make me sound tougher and that maybe he assumed I hurt my back by lifting a bathtub instead of simply twisting wrong while stepping into my underwear. Sigh.

That leads me to the " living a few years of your life like most people won't."

I guess I have a hard time calling myself an entrepreneur because these first couple of years have been challenging with family and friends. Change is tough for others to accept, especially when they can't visualize the future as you see it. I was determined to make my business succeed. My life became consumed with my entrepreneurial passion and time with old friends became fewer and far between. New relationships were developed with fellow entrepreneurs which also was a thorn in the side to my old friends. The girls' weekend away was replaced with a business conference with my new friends in Vegas.

Family is even tougher to convince of your business goals when you were raised to work hard and save your money. Taking risks is just foolish. You go to college and pay a ton of money for a degree that you may or may not use. Then you find a job where you spend endless hours making your superiors rich while the money you earn goes to pay down your college debt. What sounds foolish to me is working at a job for decades and then being let go simply because they can replace you with a younger, cheaper version of you. If you do make it to retirement, here's a watch and a celebratory lunch but don't take too long because the rest of us have to get back to work. Why do people settle for this lifestyle?

Starting a business was not a decision Vance and I took lightly. We paid tens of thousands of dollars for an educational program that provided tools when backed with action and implementation, cleared a path towards success. We took advantage of coaching opportunities any chance we got. We attended meetups in our area to network with other real estate investors. We would travel to three-day events all over the country for focused education in specific real estate niches. We. Were. All. In.

My drive to succeed was fueled by the overwhelming unhappiness in my current job in the health insurance industry. I had no passion for it anymore and did not feel valued by my superiors. The first few months, I would go to "the job" early so I could leave by 3 pm. Then I would come home and dig deep into my training modules, read books on real estate investing, study the market, evaluate property after property, and more. This never felt like work but it consumed me. This new obsession also didn't make sense to my loved ones for they saw less and less of me. As our business grew, huge milestones would be achieved with just a muted golf clap from the home team fans. Becoming an entrepreneur felt very lonely at times.

After seven exhausting months of juggling real estate and my corporate America job, it was time to submit my resignation so I could focus on our business full time. Our hard work was starting to generate some income and even though I was scared out of my mind, I needed to take that giant leap of faith. A wise coach once told us to never have a Plan B. For those people that have a Plan B, almost all of them will be sure to find themselves falling into that safety net. Our only option was to prosper and grow our business towards greatness.

When I printed off this quote years ago and posted it throughout the house, I did it to give myself a daily reminder that I needed to work hard. How ironic that the toughest part of "living a few years like most people won't" had nothing to do with me busting my ass but everything to do with dealing with most people in my life.

It meant that most people I know won't ever support my decision to better my life.

Most people won't take risks because they are too afraid of what lies on the other side of fear.

Most people would rather judge me for accomplishing something they never had the courage to do.

Most people are waiting for me to fail so they can say, "I told you so" from the comfort of their office cubicle while waiting for Rhonda to finish with the one working printer on that floor.

Tragically, most people do what they were taught and never take the initiative to follow their dreams.

So, why is it so hard to call me an entrepreneur? I wasted so much energy trying to prove to others that I AM a successful entrepreneur when what I really need to do is look in the mirror and convince myself. The answer lies in accepting the second half of that statement.

" you can live the rest of your life like most people can't."

Whoa! That's me...I'm there! Right now...this very minute...I am living the rest of my life like most people can't!

I own four different companies at this point, I AM an entrepreneur! We are getting ready to open The Acorn Agency, a brokerage for real estate investors to hang their real estate license. This will be my fifth company. We started with Jolific Homes, our house flipping business, or active income. We then created Jolific Properties which covers all our rental properties, or passive income. In the middle of 2019, I created the Real Estate Investor Growth Network (REIGN) which is a virtual mastermind and network for investors across the country. REIGN allows me to dust off my teacher hat and coach others, which fuels my soul. My fourth company is my super-fun side hustle, Color Street. Color Street is a direct sales company that sells one simple product, nail polish. Yep, that's right. I sell nail polish and love it. Besides being an amazing product, it provides much-needed girly-girl time after hanging out with contractors all day.

Warren Buffett says the average millionaire has seven streams of income. If you include the interest we earn from being private money lenders thru our self-directed IRA, I'm one stream of income away from hanging with Oprah. Am I a millionaire yet? Not even close. Do I have a better chance than those collecting paychecks? Absolutely. I have responsibilities that when completed, increase MY success, not the success of a company that can replace me at any time. I am doing EXACTLY what I have set out to do.

As an entrepreneur, I decide how to spend my day. I get to choose to surround myself with people willing to lift me up instead of pulling me back down to their comfort level. I thrive in educational settings for I find limitless gratification in learning new strategies and tools to grow our business. I have the opportunity to make decisions that will help our clients and community. I have found a passion that I love so nothing in my business feels like work. I get to wear jeans and sneakers every day. I change lives by providing employment and establishing partnerships with other small business owners. I have the privilege of being a role model to those just starting out. My success is based on my actions which allow for unlimited abundance along with the security of controlling my destination. I can even take a nap after lunch if I want to.

I am an entrepreneur and I am living the rest of my life like most people can't.

I can also now spell entrepreneur...

Make it a great day! Whoop whoop! *Read more blogs by Jen Josey at

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Oct 04, 2021

Helllo mate nice blog

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