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Uploaded:2022-05-19
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In this video, one woman shares her experience working for a baby boomer boss, and the observations she's made when it comes to generational workplace values.

Through weekly video essays, "Making It Work" showcases how *real* people have upgraded their personal or financial lives in some meaningful way. Making your life work for you doesn't mean getting rich just for the sake of it. It means making the most of what you have to build a life you love, both in your present and in your future. And while managing money is a crucial life skill for everyone, there's no one "right way" to go about it — you have to figure out what works best for *you,* full stop.

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Written by Elizabeth Jacobs

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With 1.8 billion of us worldwide in 2021, millennials officially became the largest living adult generation.

There's only one generation that has seen such large numbers before this a cohort of people all born in the aftermath of World War II, otherwise, known as The Baby Boomers. I am a millennial.

And chances are if you're watching this video, you are too. And although I believed I was acutely aware of the many ways in which millennials differ from their Boomer counterparts from thoughts on marriage, to housing, and even climate change, I wasn't so consciously aware of the Boomer attitude towards careers and employment. That is until I found myself working for one.

While boomers are typically near retirement age, they're working longer than previous generations. With some adopting new ways to stay relevant in an ever changing workplace. My dad is a Boomer.

And one thing he's always taught me is that experience doesn't always come with age. He regularly works with younger people in his field. Combining his learned skills with their fresh takes on tired strategies, often reaping the rewards together as a team.

But while some boomers are open to learning from younger generations seeing their employment as opportunities to help their businesses adapt and grow in exchange for their guidance and mentorship. Others are under the impression that simply hiring younger people to work for them will have the same end result as nurturing mentor or mentee relationships. I interviewed for a job that admittedly sounded a little weird and out of the ordinary.

But it proposed a lot of personal growth among responsibility and decision making. So I chose to see the opportunity when the offer came in. When I told my father of the working situation with a Boomer CEO as the only other employee, he earnestly advised me to stay true to myself and not be intimidated by what could be an old way of working.

I observed many things from my stint working for someone fitting the OK, Boomer stereotype. Here are just a few. Number one, boomers value confidence and work off intuition and charm.

When I had been working for my boss for less than a week, they revealed to me that although they'd received 200 resumes for the role, I was the only person interviewed before being offered the job due to my confidence when answering their tricky and often personal questions. Whilst flattering to an extent, it did start to make me question other scenarios where my boss's intuition was guided more by the charm, grand gestures, and sometimes utter flamboyance of our pitches, rather than the actual quality, although I feel we shared this instinct of intuition and gut feeling, I feel more likely to see through sales tactics as a millennial. We've been constantly bombarded by them through most of our lives, particularly on social media.

And so take more time to assess from all angles before committing to the shiniest proposal. Number two, boomers believe age plus authority equals experience. Working for my Boomer boss was often like the scene from Matilda, where Mr Wormwood says to his daughter, ''I',m smart, you're dumb; I'm big, your little; I'm right, you're wrong, and there's nothing you can do about it.

Though I'm not implying I was intellectually superior to my boss in the way Matilda clearly was to her father. It was still very frustrating to work with someone who had less direct experience with the projects we were working on, but would insist that being 30 years my senior was reason enough to routinely cut me off mid-conversation. This happened embarrassingly on more than one occasion in front of clients making me feel dumb little and wrong.

Number three, boomers believe you should just be grateful for a paycheck. When I first started working with my boss, I had to regularly clarify what my role was. Generating ideas, meeting with clients, helping build a company from the ground company was what I was hired for.

Booking taxis, organizing their home office, pandering to their children, I was not. When I had a frank chat with my boss, although they took these points on board and my role started to form into what I had originally applied for, my boss also reiterated the belief that it didn't matter what I did, I still got paid at the end of the month. One time, when we were having yet another uncomfortable conversation in a SoHo bar about a lack of pay increase, despite previous promises.

I saw one of the servers slyly point to our table and mouth to his colleague sugar daddy, which came just after my boss made the comment I pay for your life, so you should be grateful. Which among many toxic comments leads me to my final learning. Number four, boomers don't care what people think about them way past the age of midlife crisis, my boss had reached a milestone that I think we all hope to reach one day.

But is particularly synonymous with the Boomer generation. They do not care what anyone thinks of them, ranging from poorly themed jokes, outrageous fashion choices, one day they sauntered in wearing a full kimono, a hairstyle that should have been left in the 1980s, and sending food back despite knowing it was likely to be spat in. My boss did not give a damn.

What this no forks given attitude did teach me is that there are some situations in which I perhaps need to lighten up and not take life so seriously. But more importantly, it taught me to follow that millennial intuition of mine and speak up when I think something is wrong. Despite what people think of me regardless.

Working for a baby Boomer was not a wholly negative experience. At times, it was odd when they'd remark how alike they thought we were, because in my mind they were wrong. But I learned more about myself by being around someone who was both generations apart from me in age and attitude on life.