Should You be Starting a New Career over 40?

Starting a new career over 40

Just when you thought you had things under control… how do you know when you need a new job?

I’m in the process of being rather unceremoniously pushed out of my current job for many years. I have NOT been fired. There has been NO layoff. Starting a new career in finance over 40 is of no interest to me and I am not ready for retirement. I’ve just been instructed along with a few others to find a new position because our project is ending. I’m viewing this as an opportunity to finally make the transition I’ve been wanting to make for a long time. In doing so, I’ve been warned repeatedly that I’m up against a seemingly hopeless cultural phenomenon known as “age discrimination,” and I’m coming to terms with the best way to deal with it.

Becoming a “Senior Citizen”

Some of my earliest memories involve hearing my grandmother angrily telling someone at the utility company customer service department, or the fast-food drive-thru, or the social security administration, “I’m a SENIOR CITIZEN!” and then she would proceed to tell them why they should fix whatever was broken. In Grandma’s defense, she had a lot of responsibility, and a lot of problems to deal with, and sometimes that “senior citizen” card was the only one she had left to play. That was the 1970s, and she had grown up in a rural area, and in an era where her options for career choices were limited. She was spunky, smart, and always ready to learn new things. I’ve often wondered how her life would have been different if she’d lived in a more metropolitan area, or if she had lived long enough to experience the Internet.

But that was then, and this is now. The world has changed, but people have not. The “young people” of Grandma’s day – the ones she needed a little respect from – were the “baby boomers.” Nearly 50 years later, that generation is now crying “Age discrimination!” the same way Grandma used to cry “I’m a senior citizen!” It’s the same game, but the players have changed. Now, the “millennials” are the ones who don’t respect their elders.

Fortunately, the world really has changed, and a lot of this conflict is now completely unnecessary and irrelevant. Thanks to technology and advancements in civilization, people have many more options for living healthy, independent, fulfilled lives for much longer than has ever been possible.

Start a New Career over 40 by Continuing to Grow

Maybe when you were a small child, you had fun with a fantasy character like Santa Claus, or the Easter Bunny, or the Tooth Fairy. There was a point when you realized these were just that – fantasies. Did you stomp your feet, and scream about people not letting you be a baby anymore? Or did you put on your big kid pants and move on to the next stage of your life?

The same happens with school. Or at least it’s supposed to. As someone who stayed in school entirely too long (and has the student loan to prove it), I can tell you, it’s not “cool,” and after a while, it’s time to graduate, and move on with the next stage.

For many of us, the corporate world becomes a way to stay in that sophomoric, comfort zone. But even there, a time comes when the dream either becomes the Hotel California (i.e. It’s a trap!) or we begin to realize that we’re like that creepy 20-year-old that was always hanging around the high school parking lot, trying to salvage his glory days.

There are entire (very expensive) “master classes” available right now targeting people who are in their 50s and 60s who are trying desperately to get back into a job that no longer exists. These programs teach attendees how to speak, act, and dress like they’re 29, and format their resume’s to “trick” the recruiters into thinking they are younger.

For what? Do you really want to be 20 years old again?! Why are we trying so hard to be accepted where we aren’t wanted?  The battle to get in the door is usually easy compared to the one you’ll be fighting every day after you get in.

Starting a new career over 40

When is enough enough?

As we mature, we change – mentally, physically, and emotionally. The things we want and need out of life develop. It’s great to stay healthy and vibrant and active for as long as possible, but it’s not particularly healthy to refuse to grow up. If we stay “stuck” at age 39, we’ll never experience the joy of being a “senior citizen.”  Yes, we may still have bills to pay, but maybe there’s a way to do that without trying to turn back the clock.

I turned 50 a while back, and I know I have a lot to learn (my Mother will be happy to confirm this). My goal for this next stage of my life is to move into a more fulfilling role, apropos of MY experience and MY life – not a fantasy one that no longer exists if it ever did. I’ve been fortunate to have a lot of good mentors over the years, and I want to step into that mentorship role. When dealing with young people, I want to be helping them, not trying to be one of them, or awkwardly trying to win their approval and acceptance. Like it or not, I am the adultier adult.


Jenn Pointer made her career in the financial world. In midlife, she left that world to become a talented digital artist and writer. You can find her on Instagram at JennsPoint.