Chapter 1: Understanding the Challenges of Self-Employment

In recent reflections, I've come to realize the common pitfalls that many aspiring entrepreneurs face. Perhaps you can relate to this experience.

Photo by Luke Jones on Unsplash

As a tax specialist marking my 15th year in the field, I’ve decided to expand my operations this tax season. To manage the increasing workload, I sought to hire bookkeepers and assistants to streamline the administrative tasks.

I posted job openings on social media platforms like Facebook and LinkedIn, clearly stating that these were contractor roles and that applicants needed their own bookkeeping setups. However, I was surprised to find that many candidates hadn’t even bothered to read the job description or understand what my company does. How can one expect to secure a position under such circumstances?

Despite this, I chose to hire those who demonstrated relevant experience in bookkeeping for tax purposes. Within a week, three of them began working on a project I assigned. However, a week later, I reached out to inquire about their progress, as I hadn’t received any updates, and they were expected to complete the task within two weeks. This interaction revealed much about why so many individuals fail in self-employment.

One of the most promising candidates, who had previously worked as a self-employed individual, texted me expressing confusion about how to start due to a lack of accounting software. Shockingly, she was considering returning the paperwork just a week after starting the assignment! If you are self-employed, it’s essential to have the necessary tools to perform your job effectively. Imagine showing up to an employee role without the required equipment!

This candidate displayed no intention of investing in her business. She believed that her clients should cover the cost of her accounting software while she simply did the work. This attitude reflects an employee mindset rather than that of a business owner. You cannot expect the security of having tools at your disposal while simultaneously enjoying the flexibility of self-employment. She applied for the role because she needed more clients, but it became evident that her lack of investment in necessary resources was a barrier to her success.

Later that evening, I encountered an even more alarming perspective on self-employed professionals. This established bookkeeper expressed her dissatisfaction with receiving multiple follow-up texts regarding my client, arguing that it is common sense to wait for a response. She failed to grasp the urgency of the situation, as the client had a looming deadline for submitting sales tax. This mindset underscores why many businesses incur late filing fees; being self-employed does not grant you the luxury of working at your own pace. Deadlines are dictated by the nature of the work, and disregarding them can harm your clients.

The third bookkeeper I hired was someone I initially thought would struggle. She was transitioning from an employee role to self-employment and seemed eager to learn. I provided her with a manageable assignment, but when she came to collect the bookkeeping paperwork, she insisted on a formal contract. This request highlighted her employee mentality, as contracts aren’t typically necessary in self-employment; payment is contingent on the work completed.

Despite her initial hesitation, she eventually purchased the accounting software and sought my guidance on using it. Although she faced challenges with the new version of the software, she ultimately began to engage with the work. However, she soon became overwhelmed, calling me in a panic over calculations and entries. I was astonished, as the fundamental process of bookkeeping involves straightforward data entry and matching receipts to bank statements.

Her struggle illustrated a significant issue: she was confined to her previous methods and couldn’t adapt to the self-employment landscape, where flexibility and creative problem-solving are essential. When I began my tax preparation career, I had to adapt and expand my skills to accommodate clients with small businesses. This evolution was a conscious choice; failing to grow alongside your clients can quickly lead to business failure or insufficient income.

After a thorough discussion with the third bookkeeper, she realized that she had unnecessarily complicated the process. I advised her that the key to succeeding in self-employment lies in the KISS (Keep It Simple, Stupid) principle.

Establishing a routine within your workflow is crucial. The more consistent your processes, the more diverse your work can become. This structure offers a comfort zone that allows for expansion and variety, ultimately leading to the financial freedom that many new self-employed individuals strive for as they grow into small business owners.

As the adage goes: “If you do the easy things, your life will be hard. If you do the hard things, your life will be easy.”

Chapter 2: Valuable Lessons from Entrepreneurial Journeys

The first video, "Unveiling the True Story of Business Success: Tracy Jepson's Entrepreneurial Journey," provides profound insights into the realities of building a successful business. It highlights the challenges and triumphs faced by entrepreneurs.

The second video, "Unveiling My Cricut Business Secrets: $605 in Second Month In Business!" shares practical strategies for achieving success in a side hustle, offering inspiration for those embarking on their entrepreneurial journeys.