Real Talk: The Highs and Lows of Being a Contractor in the EdTech World

I’ve been an educational contractor for over three and a half years now, and I absolutely love it! I’ve had the privilege of working as an independent educational contractor for exceptional companies, including Defined Learning, PowerSchool, and Amplify. My role as a contractor involves taking on various responsibilities: I’m a trainer, a coach, a mentor, and a curriculum writer. Whether I’m working from home or traveling to school systems across the country, this career has been quite a journey—and I feel like I’ve only just begun!

While the rewards of this path are numerous, there are also challenges. Let’s dive into the highs and lows of being an EdTech contractor.

High: The Perks of Travel

As someone who loves to travel, this job has been a dream come true. Back when I was teaching, vacations were limited to school breaks, meaning I could only squeeze in one or two trips a year. Now, I’m on the road three or four times a month! The perks that come with frequent travel are hard to beat.

1. Travel Rewards: As a Platinum SkyMiles member with Delta, I enjoy upgrades to first class, and my Southwest points often cover personal trips.
2. Hotel and Car Loyalty Programs: Thanks to loyalty programs, I enjoy free nights at Hilton and Marriott hotels and free car rentals with National. These perks are some of the biggest upsides of being on the move.

Low: Out-of-Pocket Expenses

Of course, traveling for work isn’t all glamorous. One of the biggest downsides is handling out-of-pocket expenses. While the companies I work for cover my travel costs, these aren’t always paid upfront.

1. Airfare and Travel Costs: Airfare hits my credit card weeks before I board the plane, and I often rack up significant expenses during a single trip—hotels, rental cars, gas, meals, parking, tolls, and more.
2. Reimbursement Delays: Though I’m eventually reimbursed, the timing doesn’t always match up with my credit card billing cycle. This can lead to a running balance on my business card, which feels overwhelming at times. Over time, I’ve learned to set aside money to cover these costs while waiting for reimbursements to arrive.

High: Connecting with Other Educators and Trainers

One of the most rewarding aspects of being a contractor is meeting incredible people. The connections I’ve made with other trainers and educators have been invaluable.

1. Professional Growth: Collaborating with fellow trainers has allowed me to grow personally and professionally. I’m constantly learning from others in my field, which helps me become a better educator.
2. Inspiration from Educators: I’ve had the privilege of working with passionate educators from school districts across the country. Hearing their stories and learning about their experiences has been inspiring.

Low: The Solitude of Traveling and Training Alone

As much as I love traveling, it can get lonely at times. Being the only trainer on site often means spending long periods alone.

1. Dining Solo: While I’ve learned to dine solo, it’s not always enjoyable. Exploring new cities by myself can feel isolating, especially after a long workday.
2. Lack of Companionship: There are times when I wish I had a travel companion to share these experiences with, especially during those long evenings when the workday is over.

High: Excellent Income Potential

When I retired from teaching, I was paid $26 an hour for my unused sick leave. At the time, I thought that was a decent rate. Now, as a contractor, my earnings have increased dramatically.

1. Daily Rates: Depending on the company, I make anywhere from $300 to $1,000 per day.
2. Flexibility and Earnings: The flexibility to choose when and how often I work is another huge perk. Last month, for example, I earned over $10,000 (before taxes), which is quite impressive for setting my own schedule!

Low: The Inconsistent Workload

While the pay can be great, it’s not always consistent. The workload tends to ebb and flow, depending on the time of year.

1. Busy Seasons: The busiest months are when schools are in session—typically August through November and January through March.
2. Slow Periods: During other times of the year, like when schools focus on testing and year-end activities, work can slow down considerably.
3. Financial Planning: Planning ahead is essential to ensure the income generated during the busy season can sustain me through slower periods. I also try to take on additional projects, such as curriculum writing and coaching, to maintain a steady income.

The Verdict: Highs and Lows, But Worth It

Being an independent educational contractor certainly comes with its ups and downs. The highs, like the flexibility, travel perks, and excellent income potential, make the challenges worthwhile. However, it’s important to acknowledge the less glamorous aspects—out-of-pocket expenses, inconsistent workloads, and the solitude of traveling alone.

Overall, this career has been an exciting and rewarding experience for me. If you’re curious about becoming an independent educational contractor, consider checking out Teacher Transition’s Become a Trainer program! You’ll have the chance to learn from some of the best in the field (including me!). Follow my affiliate link to find out more.