Entrepreneurship Isn’t Always Pretty

When Lori Cheek needed money to keep her business afloat, she looked around her sleek New York apartment to see if there was anything she could sell. Her eyes landed first on her $40,000 wardrobe and she immediately knew what she had to do.

Six years ago, Lori founded the online dating company, Cheek’d. Four years ago, she quit her high-paying architectural job to fully dive into her entrepreneurial venture. And luckily she did.

Her idea on how to revolutionize the dating industry took off after the New York Times wrote, “Move over Match.com. This is the next generation of online dating.”

After that, newspapers across the country were featuring her business and the international market was demanding to know when Cheek’d would be available for the rest of the world. Thousands of people were signing up for her online dating service—so many that her website would crash for days at a time (until she was able to hire a good web developer). There was no way this could be a part-time gig if she wanted it to succeed, so she ditched her day job and jumped into the trenches.

graphic_not-prettyBut despite her business’s new-found international popularity, she still needed more money than she had to grow it. At some point down the line, she had to make a tough decision to let go of a few things in order to pay the bills.

First, she decided her wardrobe had to go. In her last day job, she had been assigned to work with Christian Dior in Paris and had the expensive clothes to prove it. Now it was time to wish them farewell as she sold them on Ebay and in consignment stores.

That wasn’t enough to keep her business going, though.

She looked around at her beautiful New York apartment and saw another opportunity to make money. Then she shoved her ego down, packed up a suitcase, and headed for her friends’ couches while she rented her apartment on Airbnb.com.

After working a glamorous day job for over seven years and living in gorgeous apartment, she instantly became a broke, homeless business owner.

Let’s face it, entrepreneurship isn’t always pretty.

Owning a business isn’t always a charming Mother Goose fairytale ending with, “And they all lived happily ever after.” Nor are there fairy godmothers, genies in a bottle, or knights in shining armor to get you out of a jam when the going gets tough.

I’m not going to lie to you…the chances of you coming up with a spectacular business idea, launching it, and instantly making tons of money is slim, at best. Nine times out of ten, that’s just not how small business works in the real world.

Instead, entrepreneurship has its major ups and downs. It’s not a straight and narrow path. And if you’re on the path, this is what your non-fairytale entrepreneur life might actually look like:

  • Crashing at your parent’s house for an extended period of time
  • Living on your friend’s couches
  • Pawning your home
  • Getting into 5-figure credit card debt
  • Downsizing your home, car or wardrobe (in Lori’s case)
  • Working 10-12 hours a day, seven days a week
  • Applying for a part-time job to pay the bills
  • Asking your family for money
  • Having your first few businesses fail miserably
  • Not being able to go out with friends very often
  • Vacation…what’s that??
  • Getting sued by disgruntled clients you were trying to help
  • Wasting a ton of money on people, plans and ideas that never pan out
  • Being stuck in a day job you hate will your business gets ramped up


Now we’re painting a more accurate picture of entrepreneurial life!

This is what it’s really like to be in the small business trenches. And I didn’t make any of this up—each of these circumstances has either happened to me, a small business owner I know, or an entrepreneur I interviewed in the past.

Not so pretty, right?

But am I telling you all this to scare you or deter you from becoming an entrepreneur? Not quite. I just want you to understand is that it’s completely normal to go through tough times as a business owner, just like Lori did.

Yet, when you’re smack dab in the middle of a “tough time”, it’s easy to feel like your business is a massive failure. You look around and see all the thriving business owners and wonder why you’re not among them. You wonder…

What’s wrong with me? Why am I struggling? Why are other businesses taking off while mine seems stagnant? What am I doing wrong???

What you may not realize is that every entrepreneur on the planet is dealing with similar struggles as you (or has gone through them in the past). You are not alone.

But how do you get through these hard times without wallowing in misery or completely giving up? Here are a few useful tips to help you get through the inevitable struggles of business ownership…

#1: Stop comparing your inner business world to other business owners’ outer worlds

If you only read the NYT article on Lori’s company Cheek’d and watch her pitch her idea to the Sharks on Shark Tank you might think her path to success has been smooth sailing. You wouldn’t know she was couch surfing and strapped for cash during her entrepreneurial career. All you’d see is her business from an outside perspective—the chic architect-turned-entrepreneur fairytale.

Success in business only looks like success from the outside. “Successful” business owners are dealing with the exact same struggles, challenges and fears that you are. It just doesn’t look like that from the outside.

Make a commitment to yourself to stop comparing your inner business world to other business owners’ outer worlds. That’s like comparing apples to orangutans—there’s no way to make a logical comparison. You’ll just end up feeling bad about your progress, second-guessing yourself, and wondering why other people have it so easy when you don’t. (Check out my article 5 Ways to Stop Worrying About the Competition & Start Building Your Business.)

#2: Redefine your definition of success

If Lori’s definition of success was making 6-figures a year and hiring other people to run the daily ins and outs of her company while she sat under an umbrella in the Bahamas, she’d be falling painfully short of her goal during her couch-surfing days. No doubt she’d feel like her business was a big fat failure.

Instead, imagine if her definition of success was, “I get to wake up every day and work on something I love.” Then she would feel successful every day—homeless or not—because she was a full-time business owner pursuing her dream.

What is your definition of success? Is it time to redefine it?

Don’t set your vision for success so far off in the future that you can’t see the light at the end of the tunnel. Instead, create a definition of success that you can measure against your life in a positive way every day. This will make the tough times of being a business owner not seem so tough because it feels like you’re constantly succeeding.

Here are some ideas:

I am successful when I get to wake up every day and work on something I love.

I am successful when I spend time each week working towards my long-term business goals.

I am successful when I get one new customer.

I am successful when my passive income exceeds my monthly bills.

I am successful when I have the freedom to set my own schedule.

You don’t have to be a millionaire to be successful OR feel successful. Redefining your idea of success allows you to feel more positive and motivated in the short-term as you work towards your long-term goals.

#3: Know your “why”

Lori bootstrapped her business from Day 1. And she’s so committed to her business and her vision that she wasn’t going to let a lack of funds get her down. So she did what was necessary to keep her business afloat, pay all her bills, and keep pushing forward.

Was it fun to sell off half her belongings? Probably not. Was it a blast living on her friend’s couches for a few months? I’m guessing “no”. Yet, even though Lori went through some tough times, she knew she was making sacrifices for a reason—she wanted to see her idea turn into a thriving business.

If you’re going through tough times with your business right now, make peace with your current situation by knowing your “why”. Why are you running your business? Why do you want to succeed? Why are you making sacrifices?

Basically, you’re running your business for a reason—what is that reason?

Focusing all your attention on your “why” will allow you to go the distance when the going gets tough. Bumps in the road are just a part of the entrepreneurial journey, but by keeping your eye on the horizon of your ultimate goal will allow you to arrive at your destination unscathed.

Sharing makes you awesome!
Lori Cheek Took Cheek'd from an Idea to the Shark Tank - 5 years ago

[…] Entrepreneurship Isn’t Always Pretty (latest article on GFY about Lori) […]

» 7 Ways In The First 90 Days To Sabotage Your Online Business - 4 years ago

[…] Laurel Staples captures the idea of expectations for entrepreneurs perfectly in her post, Entrepreneurship Isn’t Always Pretty… […]

Comments are closed

Malcare WordPress Security