How to Talk with Baby Boomer Parents About Success

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Who else to ask about the wild, wild workforce than your parents. You’re old enough to understand the value of their advice and keen enough to filter it through your own perspective. A road block will materialise at some point, however, one so immovable it must be bigger than just you and your parents. Welcome to the misaligned definitions of success between you and previous generations.

At this moment, three generations dominate the workforce: Baby Boomers, age 56-71; Generation X, age 36-55; and Millennials, age 21-35. Each grew up with distinctive political and social circumstances, technologies, degrees of globalization and learnings from previous generations. These in turn affected that generation’s motivations, views toward work-life balance, career goals and of course, definitions of success. The following analysis will be American-skewed, but can serve as an example for your own nationality.

A generational spread like the one above might mean, as in my case, that your entire family spans over all three. If my parents are reading this, they should know talking about career trajectories is easy in one regard, but difficult in another. As varying species of trees can thrive off the same nutrition and sunlight, my family members share similar beliefs, but walk divergent lanes. At first, I considered talking with my parents about my beliefs behind success, realising that without understanding theirs, it would become a teenager-like conversation.

Take a look at your family’s generational mix. In my family, for example, we have Baby Boomer parents, a pretty much Generation X brother and Millennial me. We all value each other’s perspective, but understand that attitudes on career and life success vary. This variation results in tangible lifestyle differences, which our family share and discuss. It wasn’t until recently I was able to connect these distinctions to generational gaps.

The Baby Boomers’ perspective, or my parents’, took lessons from their turbulent atmosphere. This generation grew up during the Civil Right Movement, Space Race, sexual revolution, the Beatles and rise of computing. They went through university as non-conformists to then transform into seeking-security employees in the workplace. Success is achieved, according to Baby Boomers, through a strong work ethic and competitive environment. Climbing the corporate ladder at the right company exemplifies an acceptable career path. These factors led to high divorce rates, pension insecurity and health issues that would sway the next two generations.

While Baby Boomers might read Dilbert in the newspaper for their work-related humor, Generation X watched Office Space as a Blockbuster rental. This generation saw the world formed by events such as early PC and mobile technologies, divided families, Cold War endings, Y2K and Michael Jackson. Their skepticism over the past generations’ values resulted in challenging authority and self-reliance. They are entrepreneurial, open to multi-career paths and direction-driven. Success for Generation X is gaining authority, maintaining a work-life balance and building skills.

Now comes my generation, or the Millennials. We watched news stories around 9/11, globalization, global warming, Iraq invasion and the internet. With the increased access to information and cultures, we are more diversity-focused, enthusiastic to contribute and always asking, “So, what’s next?” Moving from career to career is considered normal, a huge leap from Baby Boomers’ one path projections. Our definition of success is still taking form, but a meaningful career, global network, flexible work arrangement and visible impact are already becoming clear characteristics. Millennials share similarities with Generation X, but find Baby Boomers’ perspective ridged. So how do I talk with my Baby Boomer parents about success?

Upon researching this article, my surprised revolved around how much this model worked. I never considered myself a typical Millennial - I held contrary values to high school peers, attended an art/design college and moved countries in my early twenties. However, my impression growing up of previous generations, world-wide shifts and cultural revolutions solidified values that are now revealing themselves. It’s as if the sleeper agent of my childhood is just starting to execute their life’s mission.

At some point, your discussions around career development with either parents, or siblings, will reach an impediment. Your parents might say, “But you don’t have experience in that field” or ask “Is this a hasty decision?” It’s not fair to judge their perspective as “wrong”. Values of earlier generations were embedded decades before. Next time the subject of career or life success arises, I’ll take the discussion to a healthier place. If we acknowledge each other’s assessments, we can live in the same cultural forest. Separate species of thought can benefit from diversity, especially if that diversity results from generational gaps.