An Open Letter to Entrepreneurs in the Messy Middle

business skills entrepreneurs influence raychel perman Aug 10, 2020

Dear Fellow Entrepreneur, 

This letter is for you. The entrepreneur who is ready to quit because it's lonely and thankless building a company alone. The small business owner who doesn't know how much longer it will take to make enough profit to bring home a paycheck. The founder who wonders why they started in the first place. And, for everyone in the "Messy Middle" of building a successful business.

The “Messy Middle” is the years between when you start your company and when you finally make a profit and bring home a paycheck. Depending on what kind of business you are building this could be a few years, or even up to a decade. You need to know this! Because if you do not you will quit on your dream too early, thinking you are a failure.

One of my favorite accounts to follow on Instagram is the Pink Papaya, founded by Sarah Landry. She has a podcast with over a million downloads and 1.6 million followers on Instagram. She is goals for most of us. Anyway, a few weeks ago she shared in her stories that it took 5 years before she was able to quit her full-time job and run her business exclusively.

Then she said… it was 5 more years before she personally made a dime.

Do not let the perfectly curated stories and posts on social media fool you. These entrepreneurs worked their asses off to get to this point and are still working full time to keep it afloat. Also, don’t assume they had to make multiple 6 figures first to make these things happen. They didn’t wait for their ship to come in loaded down with their ideal clients throwing dollar bills at them. Nor did they wait to launch podcasts until they had sponsors and people willing to advertise. And, they didn’t stop talking about their products and services just because it felt like no one was listening. No one probably was listening. They talked anyway.

Here’s some honesty for you.

In our first business we spent money to make it look like we had money.

Not spend money to make money. That’s just marketing. But that was not what we were doing. We spent money on things we thought we needed (like assistants and a downtown office space) so we could look like legit successful businesswomen.

All the while we could barely cover our expenses. And yes, we paid other people before we paid ourselves. We also spent as much money as we made. That was the dumbest of the dumb. The messy middle was taking longer than we wanted and we started throwing around money like we had a money tree in the backyard.

Thankfully, we saw the writing on the wall before it was too late and took a hard-left turn towards new money habits. We took out a line of credit to pay off our bad debts from our first company and give us some cash to launch our next venture. No one talks about that either! But business owners usually must take out capital at some point, whether it is a loan, a family gift, or even their own savings, to bolster their dreams. This is facts so don’t feel guilty.

In fact, because of our smart money choices we have turned a profit almost every single month this year. The year of the pandemic and economic downturn. The year we rebranded. This should not be happening.  We couldn’t have done that if we hadn’t learned to live on less and not spend every dime we made. And to be honest it will be a miracle if we get to 100k by the end of the year. And I don’t care! I’m proud as punch that we are profitable in a year when many have had to close.

By this time, you might be wondering what other small business owners make in annual sales on average and how much they are bringing home to their families? I was curious about this too; and, I figured this information would help me keep our sales goals in perspective. Sales goals that are too big make you discouraged and quit. So, I asked Google and found an article called, “How Much Do Small Business Owners Really Earn” from (link) and the information shocked me. has a client base and readership in the millions that consists of small business owners from all over the world. Every year they survey their people and come up with an Annual Sales Report of both full-time and part-time small business owners. Here are the statistics from their 2018 survey.

  • 61% of small business owners made $99,999 or less in sales revenue (48% of those made less than $50,000)
  • 14% of small business owners make between 100,000 and 199,999 in sales revenue
  • 15 % made between $200k and $499,999
  • 7% made over a million dollars in sales revenue.

That’s just sales revenue. That’s not profit.

These statistics should not crush your dreams but rather give you some perspective of what it really takes to reach your goals. And, what kind of work boots you need to have on because some trenches take longer than others to dig.

If you find yourself, like 61% of small business owners, making less than $100k a year in sales revenue have hope. You can do amazing things with 100k a year. You can do kick ass stuff at 50k a year.

Especially if you have learned how to turn a profit and pay yourself in the years you made less than that.

From now on, let’s celebrate the months we turn a profit. Whoop and holler when you start taking home a paycheck from your years of hard work. Celebrate when you reach 50k in revenue. Celebrations should abound when you pay off debt and become a self-sustaining business model. Why? Because the Messy Middle lasts a long time. And every milestone is worth celebrating.

This is not the time to quit. Sure, it takes a really long time to reach the high dollar sales goals. But you are not a failure because you are still in the messy middle. You are learning to make a profit, and you are working towards paying yourself plus paying the bills. And you are building something others only dream of. That my friend should make you so proud. Keep going. Don’t quit.

With grace & grit,

Raychel Perman

Hey, before you go!

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