5 Pitfalls of Becoming a Service Contractor

If you’ve been thinking about leaving your day job to start contracting or even launch a side hustle, take notes—this blog is for you. Recently, I shared a podcast episode about how to successfully start a contracting business, and the feedback has been incredible. People have already begun implementing the strategies I discussed, from building websites to taking bold steps in their entrepreneurial journeys.

I didn’t initially plan to open up coaching, but after seeing the potential for growth in others, I felt compelled to guide aspiring leaders in our field. The results have been amazing, with clients making tangible progress in weeks. If you’re ready to take the leap into contracting, let’s dive into some key insights, pitfalls, and tips to help you succeed.

Redefining Success and Failure

One of the biggest roadblocks to starting something new is fear—fear of failure, fear of judgment, or even fear of success. But here’s the truth: failure doesn’t exist.

Let’s look at the dictionary definitions:

• Success: The accomplishment of an aim or purpose.
• Failure: The lack of success.

The problem often lies in having a vague aim or purpose, which makes success feel elusive. Success doesn’t have to mean hitting a specific financial target or achieving something that lasts forever. For example, if you started a business that served its purpose for a time and then closed, it wasn’t a failure—it was part of your growth journey.

The real challenge is overcoming the perception of failure, especially when it comes from within. Imposter syndrome and self-doubt are normal, but they shouldn’t drive your decisions. Remember: you don’t need anyone else’s validation to define your success.

The Pitfalls of Contracting (and How to Overcome Them)

While contracting offers freedom and flexibility, it’s not without its challenges. Here are some common pitfalls and how to navigate them:

1. Your Organization and Systems Are on You
   As a contractor, you’re responsible for everything—billing, invoicing, scheduling, and paperwork. Create efficient systems to manage these tasks. Tools like Google Forms, spreadsheets, or invoicing software can save you a lot of stress.

2. Inheriting Incomplete IEPs
   Sometimes, you’ll inherit Individualized Education Programs (IEPs) that don’t account for indirect services. These services are crucial, so be proactive about including them in your plans and calendar.

3. Tracking Invoices and Data Across Multiple Districts
   Working with multiple school districts means juggling different calendars and systems. Keep your data organized by district to avoid confusion.

4. Isolation
   Contracting can be lonely. You won’t have the camaraderie of an office or regular staff meetings. Make an effort to build relationships with admin assistants, teachers, and even janitors—they can be your lifeline in unfamiliar environments.

5. Non-Ideal School Locations
   Be prepared to work in less-than-ideal settings, from rural schools to warehouses. Plan your visits carefully to make the most of your time.

Tips for Thriving as a Contractor

Here are some survival tips to make your contracting journey smoother:

• Build Relationships
  Get to know the admin assistants—they know everything and can be invaluable allies. A small gesture like a Starbucks gift card or a handwritten note goes a long way.

• Be Professional and Approachable
  Always maintain a professional yet friendly demeanor. Share your contact details with admin staff to make it easy for them to reach you when needed.

• Leverage the Perks
  Contracting offers unparalleled flexibility and the potential to earn a higher hourly rate. Take advantage of these benefits while staying organized and ethical.

The Bigger Picture: Success in Contracting

The beauty of contracting lies in its adaptability. Whether you’re looking to increase your income, gain more control over your schedule, or pursue a passion, contracting can be a fulfilling path. The key is to embrace the challenges, redefine success on your terms, and never let fear hold you back.

If you’re ready to start your contracting journey, remember that perfection isn’t the goal—progress is. Connect with me on Instagram (@alliedindependence) or LinkedIn to share your thoughts, questions, or success stories. Let’s take this step together toward living your most balanced, impactful life.

Don’t miss out on these incredible resources!

• IOMOS Priority List
• Clarity Workshop
• TVI Symposium