The Meandering Career Path

Have you started listening to the Whine & Wine podcast yet?

It’s okay, if not.

You’ve only missed five episodes, all of which included live-action learning curves. I’m not sure why I thought the answer to struggling with the technology of recording an audiobook was to add in the technology of a podcast, but here we are.

Besides, sound quality? Who needs it? I mean, yes, listeners … but if you just channel your inner KYW News Radio … 1060 …, you’ll actually find a lot of nostalgia in the hiccups.

Another learning curve?

Finding a balance on those weeks that include a blog (me) and a podcast (me plus Kathy). I put a lot of pressure on myself to keep the flow of a Monday blog no matter what, but good grief when I add “edit podcast” to the mix, well, my brain can get a bit overcrowded. Sure, the root cause of the overcrowding may actually be found in a bit of procrastination, but let’s not split hairs.

This week, I am going with a piggyback-podcast-blog as we’ve gotten some great feedback on last week’s episode of Whine & Wine. It’s always exciting when you hit a topic on the head of “Yes, I needed to hear that” and The Meandering Career Path was just that. 

In my home, career paths are a hot topic at the moment. Well, not just this moment but for several moments over the last, gosh, four years now? Five? Since our children were in grade school? Oh yes, that is the most accurate timeline as it was while they were in fourth grade that each of our children were first asked about career goals. It’s not that we weren’t participants in the traditional “What do you want to be when you grow up?” conversations with our kids.

It’s that our kids’ initial career goals were all very vague and fun and included responses like “a dog dula,” or “a superhero fireman who drives an ice cream truck” or “a veternarian-nail-salon-owner.”

We weren’t that shook when that first worksheet arrived home, ready to be filled out with, like, actual career aspirations. What did shook us was the follow-up as it seemed that, even as grade-schoolers, our children were immediately being steered toward springboards that would match those career aspirations scrawled on a crinkly piece of homework paper. 

As a form of parental protest, we stopped filling out that paper properly in round two. Instead, we sent it back with a one-sentence response that read, “They are just going to keep being a kid for a little while longer.” Interesting side note: many teachers enthusiastically supported our stance.

Okay, yes, perhaps we shouldn’t have onto that stance for quite so long but, again, let’s not split hairs.

Today, we have a junior in college and a senior in high school. 

Today, we have finally reached a state of calm in our home as we approach the exit ramp from years of knee-deep panic related to those dang career aspirations. Our college junior has finally found calm as they have, in fact, figured out which direction they will point at their 2025 graduation. Our high school senior has finally found calm as he discovered a college home that actually encouraged touring students to apply very much undeclared and “find that puzzle piece later,” once snuggled into their dorms. 

We found a unified calm together because the grownups in our home both had major career shifts in the last 12 months. This turned out to be perfect, perfect, perfect timing as our kids were able to witness The Meandering Career Path from a front-row seat, popcorn in hand.

Perfect. Also stressful, but no big deal (I says months later).

It makes sense, really. I suspect most children see their parents in a single career stop. We tend to skip any major career changes once our children reach middle or high school as we know how much stability matters. There will be no career moves that require relocation as we want our children to finish school with their friends. There will be no crazy career leaps as we want to feel financial stability as we head toward the college application cycle. 

Our kids’ memories often solidify well past the days when parents are bouncing from job to job. They have no recollection of the chaos that occurred when we were clocking out of one job only to clock into another job or when we were scouring the classifieds for something just a little bit better than our current place of employment. 

In our home, as far as our children’s memories go … their parents have only ever worked for one company.  

I suppose that’s why our children approach the real world thinking that “one company” will be their destiny as well.  

No wonder the view of the launch pad comes with increasing anxiety. The idea of choosing a single career that they will marry until death do they part does sound awful. Of course, we have told our children about a bajillion times that they really only need to choose what’s next or what’s first but … well, you know how receptive teenagers are to parental advice.

Look, I have statistics! The average person has twelve jobs in their lifetime. TWELVE! You don’t have to stay where you start for the rest of eternity!

Have I mentioned how valuable teenagers find parental advice?

Career paths are a hot topic in our home at the moment because Rich and I have both jumped from our previous ships. Well, he jumped, I was pushed. Let’s not split hairs. In both cases, it was terrifying. It was also a fantastic reminder that it is our skill sets and relationships that we take from position to position – not our titles. After fifteen years as a business analyst in the tech world, my brain was very much in a robotic find-business-analyst-tech-job mode at a time when most tech companies were bundled up for hiring freezes.

Eventually, it clicked. I didn’t need to work in tech anymore. I had spent years prior to my time in tech not working in tech. I could work anywhere, really, that would benefit from the skills gained in any of the fields that I’d passed through in prior years. 

When I did sign on for a new job, when shared, I was almost guaranteed a response that went something like this: Wait, now what? But that’s nothing like you did before! And then next: That actually makes perfect sense! I have taken those skills and relationships to the travel industry and am now knee-deep in absorbing all that I can about booking cruises, piecing together land tours, selecting the perfect all-inclusive, and more. I haven’t even decided yet if this will serve as a side gig or if I’ll let it fill my whole career bucket – a feeling of flexibility that is wonderful!

Oh, and yes, with this new role at Any Adventure Vacations, I am officially above average as it is my thirteenth job (need to get that badge sewn to my sash!). 

My children? Both are witnessing firsthand and for the second time this year that it is absolutely possible to take a meandering career path and find success. They have also learned that it requires a certain level of bravery and a willingness to dig into what is essentially a reinvention.

What we hope they are discovering most, though, is that today’s decisions do not have to apply to the rest of their lives.

If you haven’t had a chance to check out Whine & Wine yet, take a listen.

And, if you really want to torture your teens, have them listen, too.

To learn more about my new adventure, head to the Bearly Home tab at

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