Should I change my career at 40? I need a do over.

If you’ve been following this blog for the last — nearly 20 — years, you know I never exactly loved my career. While I struggle with depression and ADHD, I’ve managed to continue getting jobs after being let go over and over again… but the jobs I was able to get were the ONLY jobs I was offered at the time and I took what I could get. Am I lucky I got anything? Yes. Am I lucky those jobs sometimes paid a lot especially with a few solid years of stock being worth more than I ever imagined? 100% yes. But…

But.

I’m 40 and I have no employable skills. I’ve gotten by with a mix of getting lucky and having hiring mangers who had strong ideas of what they wanted and couldn’t find anyone else willing to execute on them. I have been a “yes” woman but never have built my own value in knowledge and abilities I can take from one organization to the next.

As I joined a “obviously going to be fired” zoom call last February, I no longer deluded myself into thinking the early morning meeting with my boss was going to be something else. I had flights booked for a series of conferences I was managing and my boss, over the weekend, told me to cancel my trip and meet him first thing Monday morning. I knew I deserved what was coming. I was lost, yet again, in a job that I couldn’t do. I didn’t know what to do. There were a bunch of things he wanted me to do but nothing came naturally to me and I spent too many hours spiraling over how I couldn’t do a good job. His constant berating me for the work I did do didn’t help.

If it was just that one job I’d say it’s a fluke — a bad boss — a bad environment — bad luck. But this is the story from day one of my career. And at 40 it’s no longer a little bit of imposter syndrome mixed with something I can learn. It’s obvious to me this isn’t going to improve in this field. I can maybe find the right combo of meds to help minimize my anxiety and help me focus — but even then — I’m not able to do this job at any company. Reading and applying to job postings just makes me sick to my stomach.

I’m hopeful I can find a career where I don’t feel that way about work. Maybe I’ll never LOVE working, but I want a career that doesn’t make me borderline suicidal.

Part of me is excited about starting over. Going into this with a big enough cushion that I can give myself two years to redirect and will probably be ok. It’s scary to drain my savings down, but scarier to think about 25 more years living like this (if I can even manage to find another job in my field, which is looking less and less like by the day.)

I do carry shame that I’ve failed to get where I should be at this age. If I had only focused and built my career in my field I could daily b making $250k+ a year. I could be providing for my family consistently. I could be good at my job. I’m sure shit would happen sometimes and there’d be new things to learn, but I’d be one of those people who just knew what they’re doing and acted like it. I could/should be a VP at my age. Instead, I’m applying to junior level job and not even getting calls for interviews because my experience makes no sense.

It really, really sucks.

And it’s an opportunity. To start over. Clean slate. Is that possible at 40? How am I 40? 40 with a newborn and two other kids under 5. I’m tired. And want to be a good mom too. Struggling to do a little work and also the mom thing. So how could I go back to school? I feel pretty lost right now. There are options — so many options — but which path to take? I’m scared to invest in myself. Scared to throw money at a problem when that problem is me.

I don’t know what choice I have, though. At some point the money will run out. My husband refuses to get a full time job until the kids are all in school full time, and even his full time income would not cover our expenses. I need to get it together. I have health insurance covered through the end of August and then need to either pay for COBRA or get insurance on the marketplace. It’s so expensive. Life is crazy expensive. I refuse to lose everything I’ve built over the last 20 years. The only question is — how?

(Visited 74 times, 1 visits today)

Related Posts:

4 thoughts on “Should I change my career at 40? I need a do over.”

  1. You should go for it. Although you have been very successful financially, the stress and depression that your career has brought you is palpable. You have more than enough money at this point to retire, move somewhere else in the country, and relax the rest of your life away. I know that isn’t really an option with your husband’s family right now, so I would just focus on finding something you love to do, and bringing enough money in between the two of you that you are only drawing down $50k per year or less. If you can manage that, you will be able to retire in 15 years in the Bay Area, and enjoy those 15 years in a lower stress/more enjoyable job while your kids grow up. Either that, or move this year. But trying to find another job in your current career and continuing this downward spiral is probably dangerous.

    1. Thanks. I’m still not sure what “it” is. I wish I knew what I’d be happy doing. I’ll write another post on the financial situation with budgeting and such. It’s pretty easy to burn through our savings if we aren’t careful.

    1. Yes — I think I need to make $150k or at least find a path where I could drop to $60k but be up to $150k in a few years. So there aren’t a ton of options.

Leave a Reply

Your email address will not be published. Required fields are marked *

CommentLuv badge