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1099 Tales of Entrepreneurship, Part 2

My Beginnings

The entrepreneurial journey is rarely a straight line. Paved with good decisions, bad recommendations, and everything in between, it is filled with lessons learned the hard way—but with a healthy dose of freedom and flexibility mixed in. Today, I'm reminiscing about my own 1099 adventure, sharing a cautionary tale about boundaries and the importance of choosing the right clients.

Rule #1 of Starting a Business: Have clear boundaries.

Teaching was my first professional love affair. It ignited a passion for knowledge sharing and helping young minds grow. 

I taught middle and high school, but after a few years, the burnout hit hard. My dedication to the field was unwavering, but I had to ensure the system was a good match. I craved a career that offered more control and a chance to leverage my skills differently. I realized it wasn't my calling, even though I adored working with students and my field of study. Absolutely not. In retrospect, I don't think I had the life experience or the support needed to make it work. 

Over the course of one summer, I made the final decision to leave the classroom. I might revisit education in the future, however for now, please understand that during that chapter in my life, I needed closure, and came to terms that teaching wouldn't be a lifelong relationship.

Thereafter, I had a great deal of uncommitted time, as one might expect. In 2012, I embarked on a freelance career and it was not just some sort of flirtation. It was a new sense of passion. 

business owner training her employee

So how did my freelance career begin?

Enter 60 Minutes, the weekly show that highlights news and feel-good stories about the world at large. There was a story about the book, The World is Flat, and the convergence of improved internet technologies. WiFi was relatively new, and the piece on 60 Minutes was about how work, as we knew it, would fundamentally change. People would now be able to work anywhere. Because of that, the people that you are competing with are less tied to a physical location and can therefore be anyone.

They discussed a website called Elance, where freelancers (a term I was unfamiliar with back then) could pick up projects and assignments ranging from entry-level to experienced professionals. 

To say that I was inspired is an understatement. I jumped online, set up a profile, and thought, "How hard can this be, really?" I had a lot of education, and a lot of tech-ish skills that I felt would be of value to someone, right?

Very quickly, I was picking up small projects from entrepreneurs, startups, and entertainers. Everything from creating expense reports to editing resumes - I quickly fell in love with the random, chaotic nature of it all. Every day was different and I loved it.

This doesn't mean that I didn't meet a few terrors.

manager teaching an employee

Let's call this one Greg.

Greg needed help managing his calendar, as he traveled extensively. Remember, this was before there was an app for everything. Based in Berlin, we worked over a 5-6 hour time difference.  When interviewing, Greg indicated that he could do a call at 9 am Berlin time. In an effort to demonstrate my ability to manage this project, I naively agreed to meet with Greg every day. At 3 am my time.

Was this challenging? Of course. Should I have agreed to this? Not in the faintest sense. 

I quickly realized that Greg created a completely unwinnable situation, and I had happily jumped into his claws. Not only were we meeting at this ridiculous time, but it was very difficult to track projects. He would change his mind often, seemingly mid-thought, and it was hard to call any project complete.

In short, it was chaos.

There were numerous lessons learned here, but more than anything, it was this. Be careful what you agree to. I have discovered that clients who make the most outrageous demands tend to be less collaborative when it comes to work and are less likely to pay on time.

After one month of spinning around like a Tasmanian devil, Greg called it quits, and I was glad to see him go. Oh and to make matters worse, he didn't want to pay his final invoice! More on that soon. 



Points to Ponder

  • Setting clear boundaries is crucial for success. Don't be afraid to say no to clients who make unreasonable demands.

  • First impressions aren't everything. Just because a client seems easygoing in the interview doesn't mean they will be a good fit.

  • Learn from your mistakes! Even bad experiences can teach you valuable lessons about managing clients and protecting yourself.

Take Action Now

  • Have you ever felt you were working for a client who was constantly changing their mind? You're not alone! Hit that like button and share this post with anyone who's ever tried freelancing or plans to enter the freelancing world. We can build a community of remote entrepreneurs and maybe chuckle at each other’s “horror” stories.

  • Do you have your own “Greg” saga? Have you ever set a bad boundary with a client? Write your unforgettable thriller-filled moments in the comments below! Let's commiserate and learn from each other's experiences. 

  • Want to learn the secrets to a thriving freelance career? Stay tuned for Part 3 of 1099 Tales of Enterpreneurship, where we delve into our love of serving our (amazing and sometimes difficult) clients and (hopefully) getting paid what we're worth in the process!

  • Feeling lost in the freelance world? It is normal to feel that way. Many freelancers struggle with setting boundaries, finding clients who are a joy to work with, and getting financially rewarded for a job well done. That's where we can help. Schedule a FREE Exploration Call with us today and let's chat about your freelance journey. We can help you create a strategy for success, avoid client nightmares, and take your business to the next level.

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