Leaving Teaching: 3 Questions You Need to Ask Yourself Before You Begin Your Research

Are you thinking of leaving the classroom?

Before you begin your research into what role might be the best fit for you, you need to do a deep dive into your financial situation.

Here are three questions I often ask members of Classroom to Boardroom:

  1. Do you need to carry your insurance or can your spouse/life partner/parents carry you on their insurance plan.

  2. Do you have a savings account that can carry you for up to 6 months without a paycheck?

  3. Could you afford to work part-time or as a contract employee while you get established and build your skill set?

The answers to these three questions are going to help you decide the path to take to landing your next role.

Figuring out your financials while leaving teaching

  1. Considering Insurance

    If you need to carry your insurance, you need to look for full-time roles that offer health and benefits or research the cost of getting insurance coverage outside your workplace.

    If you don’t need to carry your own insurance, you may be able to look for contract work, work part-time, become a virtual assistant, or build your own business. For instance, one of my Classroom to Boardroom students, Marjorie Stahl, completed two contract positions that led to her ultimate hiring as a Customer Success Manager at Skillstruck.

  2. Looking at your savings

    The time between leaving your teaching position and landing a new role can last from a few weeks to a year. In the ideal scenario, you’d land a new role at the end of the school year or during the summer, but that doesn’t always work out for transitioning teachers.

    A situation that I see on LinkedIn is teachers who are so burnt out that they quit their job without a new job lined up, and then they find themselves so desperate for income that they take any job they can find. Often, this lands them in a situation where they are more uncomfortable than they were in the classroom.

  3. Trying Part-time and contract work

    If you have savings that can float you a few months to a year, you can leave your position and find part-time income while you job hunt. I know teachers don’t make a ton of money (remember, I taught in Chicago Public Schools for ten years) but if you find yourself in a situation where you have a little financial freedom, you will have more options in making the transition work year-round instead of just late spring/summer.

    Options for contract or part-time income could include creating an account on Upwork, building a course or membership site on a site like Kajabi, being hired for a contract position, or selling products on Teachers Pay Teachers.

Before researching roles you can take as a former educator, you must be honest about your finances. Also, taking a course such as Classroom to Boardroom will educate you and help you think about the various career paths. Learn more about my course.


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