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Teacher Transition Advice

Updated: Feb 5

Written by: Cassie Piggott

If you would have told me a year ago that I’d be where I am today, I'd have called you a liar. I LOVED teaching and it was my plan to be forced into retirement well into my 80’s because I was so mean and unpredictable that I would become a liability. But, like a lot of things, it was great until it wasn’t.

I started my journey out of the classroom at the end of 2021 - I was burnt out and looking for a new adventure. Like a lot of other teachers who have never had to truly network before, I spent several months lurking on Linkedin. I was applying for jobs but I didn’t understand why my job search wasn’t getting any real traction. I had sidelined myself but didn’t realize it.

Thankfully, a new LinkedIn friend gave me some advice. She pushed me to get out of my comfort zone and truly network with people. I was so scared! I couldn't just send random people emails asking for their time! What if they ignored me or, even worse, were rude?? Long story short, they didn’t ignore me and no one has been rude. To be honest, the exact opposite happened!

These people gave their time to me and answered my questions. They sincerely wanted to help me and I WAS FLOORED. From that point on, I was shooting my shot all day long! If I applied for a job, you better believe the job poster and the hiring manager (if I could find that information), were getting a connection request and a DM from me. I was also pushing out content and creating videos about how my teacher skills translated to Customer Success skills.

Upskilling is important as well, and there are things about working in the corporate world that teachers just don’t know. I focused on Salesforce training through their FREE Trailhead program. I’m an absolute fool for Salesforce. I advise everyone to get some type of basic CRM training because no matter what career you move into, you will probably be required to use a CRM. Hubspot also offers their free Hubspot Academy so there’s no excuse to get out there and learn a new skill to add to your resume. You don’t have to pay a ton of money either, there are a ton of free resources out there.

Let’s talk about money . . . I know, I know, you’ve always heard that it’s rude to talk about money, but it’s not. You have to know what your skills are worth and ask for it. This can get hairy if you don’t know how much others with similar roles and experience are getting paid and don’t have a community to ask those questions. That’s where your network comes in!

Ask people and check out sites like Glassdoor to get an idea of what your compensation should look like. Don’t wait until you have an offer in hand to ask about pay and benefits. Ask that in the first meeting.

You might be asking yourself, “But what if asking about money out of the gate makes the recruiter ghost me?”

If they’re not willing to at least give you a range, then you might not want to work for them in the first place. No matter what happens, you win. I’m also thankful for a networking community that I belong to called, The High Rise, for helping me through negotiating the salary for my new role.

My last piece of advice is to not give up. Remember this is a marathon, not a sprint. It’s going to take some time but oh is it worth it!


About the Author

Cassie Piggott


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