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1099 Tales: True Stories of Entrepreneurship, Part 1

Reality: Every entrepreneur has a "Why?"


Fiction: Every entrepreneur has a strategy.


When you ask the typical small-business owner why they launched their company, you will get a narrative that sounds something like this: "I began XYZ, LLC because I noticed a need for [insert absolutely fantastic product or service]. I did my research so you don’t have to! I carefully studied the market! I wrote an amazing business plan, and BOOM, I raised a gazillion dollars."


I know, because that's exactly what I say (minus the part about making a gazillion dollars). This is not a bad thing, but it's interesting how we often focus on showcasing our successes and highlighting our picture-perfect moments, rather than the reality of what truly happens behind the camera.


entrepreneurs having fun

We normally don't discuss the shut doors, the disappointments, and the losses. Why would we? The beginning of our business journey was not all signed contracts while leisurely walking at the park. Often, it was disheartening with long winding roads. We do not want to bore you with the details of our past financial deadlocks or worse, depress you to the point of discouraging you from buying from us.


But dig deeper. Ask any accomplished small business owner for their story and why, and they will wow you. Whether it was for their family or a passion project, I believe that every small business owner has a story worth telling.


entrepreneurial board meeting

Hence, 1099 Tales. Welcome! And, if you're a former client and you think your story is here, don't fret! I've changed your name and honestly, there are no hard feelings, even if you were not at your best.


Points to Ponder


  • Have you ever dreamt of being your own boss? The freedom, the flexibility, the chance to build something amazing from the ground up... It's a powerful allure. But what they don't tell you in the motivational quotes is the rollercoaster ride that comes with it.

  • This is 1099 Tales, a series where we peel back the curtain and get real about the messy, hilarious, and sometimes heartbreaking journey of entrepreneurship. We'll hear stories from freelancers, solopreneurs, and small business owners – the unsung heroes who take a leap of faith and chase their dreams.

  • In today's part, we dived into the myth of the perfect business plan. We all know the story: a brilliant idea, a flawless strategy, and instant success. But guess what? That's the highlight reel. Most entrepreneurs will tell you a different story, so we are here to share with you those filled with grit, determination, and maybe a few late-night tears. Stay tuned for Part 2.

summer vibe board meeting

Take Action Now


  • Who can relate to this blog series? Hit that like button and share this with anyone who's ever dreamt of chasing their money-making path!


  • Write your own entrepreneurial story in the comments below! We want to hear all about it. What are some of the biggest challenges you've faced?


  • Your feedback is a gift! Are you one of our current or previous clients? Your feedback helps us make things even better.


  • Join our community! Sign up for our newsletter for exclusive content and resources to help you navigate the freelance world!



  • Ready to take your business to the next level? We offer coaching and consulting services for freelancers and small business owners.



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