Mid-Life Career Changes

Jonathan Webb
2 min readOct 5, 2021

I’ve jumped around in my professional life since graduating from college. I taught school and coached baseball, worked for several non-profits, and even helped my wife run an at-home business. As I was helping my wife I started to feel like I was missing something, like my life was moving at a speed that I just couldn’t slow down. I felt like I wanted to do something at this stage in my life but couldn’t quite figure out what that would be. As someone in my mid-40s (is 44 mid 40s or still early 40s?…someone help me out with that because I’m starting to feel old), I feel like I should already be there. I’m not even sure where ‘there’ is but I know I am not there. Or am I?

As I looked at careers in my 40s, I thought it needed to be perfect before I could move forward. I have been searching for the perfect career, the perfect opportunity, the perfect paycheck. I have applied for jobs that didn’t work out. I have reached out to friends and asked for connections. I have started and stopped blogs, websites, and other things that I didn’t think would work out. All of those things left me with the same feeling…that I just couldn’t start something new at this stage of my life.

We’re all different people (stay tuned for more ground-breaking thoughts from me!) and have different goals, dreams, passions, etc. I was not being honest with myself about what those were for me. Instead, I was believing a lot of lies and believing that it was too late for me to start something new.

It is never too late! I’m going to be writing about this a lot in the coming days but wanted to get in right now and say that it is not true that its too late. It is not true that a mid-life career change is impossible. It is not true that you’ve missed your opportunity. Finding that opportunity and finding that next thing will be challenging for sure but it is not impossible.

As I move forward with this discussion I want to say that I’m on this journey too. I am currently in the middle of trying to figure this mid-life thing out and what my next steps will be. So, you’re not reading someone who is on a stage with all the answers, I’m walking with you. I recently applied for a job in my hometown and made it all the way to the final interview stage but was not selected to move forward.

I’m going to be honest with you about my struggles and hopefully provide some great content for you as well. Stay tuned for more!

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