Here’s What it’s Really Like to Make a Late-in-Life Career Change

7 years ago, I had what I now refer to as a complete breakdown. 

I had just received the fifth email of the day from my then Superintendent, and it wasn’t even 5 am. Her last message was asking me to head up yet another committee (in addition to the three I was already chairing), outside of my contracted hours and my regular classroom duties.

To say that I was burned out as a classroom teacher was an understatement. The burnout was so real it left me physically shaking and crying on the bed next to my husband, who could only look on, horrified, as I informed him, after months of threatening it, that it would be my last day of teaching. Forever.

With that, I left my stable career and stepped into the unknown. I’d like to say that I was terrified to leave the vocation I had been in since college graduation, one that I’d excelled at and invested enough to earn a master’s degree plus 30 hours beyond that, but the truth is, my ignorance about what was to come spared me the appropriate level of fear. 

I had no idea how humbling life was about to get, and how truly difficult it was going to be taken seriously. I wrongly assumed that everyone would share my excitement and enthusiasm for my soul’s rebirth. 

I write this not to scare you from doing what I did. As hard as it’s been to course-correct, I still view it as one of the best decisions I’ve ever made, and I don’t regret quitting and rebooting. 

Perhaps I read too many inspirational Pinterest posts about starting over though because I never recall anyone telling it like it is. The Second Life Podcast never seemed to focus on anything negative that came in between the first and second life. Or if it did, I chose not to hear it.

If you’re considering a similar move, I feel I should prepare you, so here’s the good, the bad, and the ugly about making a midlife career change.

1. You might take more than one step back to take two steps forward.
   • Seriously, whoever came up with that expression was not a 45-year-old woman trying to discover her true passion in life. I went from earning a six-figure salary with benefits to earning much, much less than that.
2. You know you’re capable of doing a lot, but it won’t always be easy to convince hiring managers of that, which means starting from the bottom. You’ll question your life choices when you find yourself working the cash wrap on Christmas Eve while your whole family waits for you to get home and open presents. Remember when Chandler from Friends had to work as an unpaid intern at the ad agency? You are now Chandler.
3. You’ll have to learn all new acronyms (among other things).
   • Just when I had mastered the endless unnecessary jargon foisted on me by the public education system in America, I now had a whole new set of ‘isms”.  The best part was that everyone just assumed I knew what they were talking about, which made me feel even dumber when I had to ask what a DSA was or what DTC’s were (Nordstrom has to win the award for the most acronyms in a single corporation). The good news is that when you do finally master this new language, you’ll feel like you earned a Ph.D.
4. People will think you’re flaky, especially your friends and family.
   • If you’re anything like me, and you spent your formative years in a career you didn’t love, you probably missed out on the opportunity to be a little flaky. When I was in my 20’s, there was no opportunity or encouragement to “find myself.” The message was, “Get a job.”  Like, yesterday.  So I did. And then I wondered why I wasn’t fulfilled by this magical job that everyone said was the key to happiness. I had a steady paycheck. That’s happiness, right? Wrong.
   • So at 45, when I finally decided I had enough of an airbag to step away from the career I  spent 20 years building, it came as a surprise to be thought of as a flake.
   • True, I now had to make up for lost time and find out what I was good at, what I liked to do, and what truly made me happy. These are all things that are expected of you in your 20’s. But in your mid-40’s? These are the things that will make you the topic of gossip and finger-pointing.
   • I found out I was thought of as a flake by my then hairstylist, who stated it as a matter of fact- “You know how everyone thinks you’re a flake?” I did not.
5. You might have to kiss a lot of frogs.
   • Unless you left your steady job for an already successful side-hustle, you may find you need to try on lots of different roles before you drill down to what you enjoy doing and can see yourself working for the foreseeable future.
   • I tried a few things, all within the subset of sales and marketing, before I found my true passion. You should expect to constantly evaluate and reflect on how things are going. I continually asked myself, “What do I like about this? What do I hate about this? and “What do I feel I can contribute to this?”, which led to where I am now.
6. You’ll be in awe of your bravery.
   • When all is said and done, and you look back on what went down, you will be astounded that you had the balls to do what you did. You’ll proudly tell the tale of leaving your former occupation, why you chose to exit, and how happy you are now that you’re doing what you truly love.

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