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Why Millennials Struggle to Discuss Career Concerns with Boomers

Why Millennials Struggle to Discuss Career Concerns with Boomers

This story was written by Chris Castillo. It has been adapted from a former article by Empowered Achievers

In my experience as a career clarity coach who primarily works with millennials, I’ve noticed an interesting trend: a lot of my millennial clients are fearful of talking with their boomer parents regarding their career concerns.

When clients come to me, it’s typically because they’re looking for more fulfillment from their career, and they’re not quite sure how to get it. They have doubts they’ve been ignoring for a while, and they’re finally ready to address them. It’s an exciting time, and I love getting to do this work! Unfortunately, though, this excitement is sometimes minimized once the topic of family comes up.

There are a few common reasons why millennials seem scared to tell their parents they’re working with a coach, including:

There seems to be a big divide between how boomers and millennials view careers.

While it’s hard to paint with a broad brush here, my millennial clients in the last five years seem to understand that their parents think of careers in a totally different way than they do. Millennials know their parents did their job day in and out without ever really asking themselves whether they were fulfilled. This creates a gap in the conversation, because millennials are looking for something more fulfilling, and they feel funny discussing this desire with their parents because it feels a bit entitled.

“My parents slogged through their job for 40 years and never expected ‘fulfillment’...who the hell am I to be asking for such a thing?!” Ouch.

Many parents give a voice to the fears millennials hold deep down.

Parents often have a special ability to give clout to the “head trash” we all secretly believe. For example, parents might say a fulfilling career is a “pipe dream” or unrealistic to want. They might say it’s entitled to ask for career fulfillment when it’s more important to be gainfully employed. They might even say, “Work is called ‘work’ for a reason.”

These familiar concepts are likely reasons why millennials avoid letting parents in on secret career concerns. They’re fearful they’ll be told that the thing they’re secretly worried about is true.

Millennials are not used to (or comfortable with) “disappointing” their parents.

This point cannot be understated. Fear of “disappointing” others by being honest about career concerns is a huge factor. Millennials tend to be high achievers—the folks who are often perfectionists, who have always made “good choices.” These millennials tend to think in black and white terms, meaning they’re exceptionally fearful of letting their parents down. They assume admitting hesitation or concern equates to throwing in the towel on their career, and they certainly don’t want to do that.

I remind these clients of three things: 

(1) You’re allowed to want a fulfilling career, just as your parents are allowed not to want one (if that’s what they really want).

Priorities vary when it comes to careers. Depending on the stage of life you’re in, the circumstances you grew up in, and various other factors, the tenets of what you consider a “successful” career will vary.

For some people, success is about money and prestige. For others, success is about fulfillment and job satisfaction. For some, it’s about flexibility. No matter what you consider job success, you are entitled to that opinion. That said, the only way to feel fulfilled in your career is to build it around what YOUR definition of success is (because otherwise you will never feel successful).

(2) Just because something CAN be true, does not mean it is ALWAYS true. 

Just because Uncle Larry decided to start a business that didn’t work out, doesn’t mean entrepreneurship is a death wish. In general, people’s beliefs about their career and the world around them are formed based on the things that they’ve seen and experienced. Just because your parents believe a fulfilling career is a pipe dream, it does not mean this is unequivocally true. 

It’s important to remember the reason why many boomer parents think (and say) a fulfilling career is unrealistic is because it’s easier to say that something is impossible than it is to admit that it’s possible—and that you just never went for it. Read that again.

While this can feel a bit harsh, it’s important to remember where beliefs come from. If parents are expressing a hard truth about your career, this truth was likely passed down to them as a truth by their parents and experiences. No hard feelings, but you can choose to let go of these beliefs that don’t feel very true to you.

(3) You have to live your life for YOU. 

At the end of the day, you have to live a life that makes you happy. If you’re spending all of your time worrying about how your decisions will be received or how they will impact others, you’re taking on an uphill battle. Someone will always have an opinion, so typically the best thing you can do is ensure you’re leaving yourself with a good opinion on your decisions. 

Pushing through these fears and letting parents in on career concerns can have some seriously powerful results for millennials.

One of my past clients (we’ll call her D) admitted she was “pseudo-committing” to a career transition, and a big part of that was stemming from her resistance to letting family in on her secret.

Her parents were both lawyers, and she was scared to tell them she wanted to leave her successful career in recruitment to explore something more fulfilling. She was scared they would say (as they had in the past) something along the lines of, “Well we didn’t expect fulfillment from our careers, but these jobs enabled us to support you and our family. Why would you think you’re entitled to fulfillment?”

Here’s the thing. Once D finally mustered the courage to let her parents in and tell them what was really going on, she felt free. From that point on, she was able to wholeheartedly put her effort into figuring out what kind of job would be a better fit for her long term.

It was very powerful.

Whether millennials decide to let parents “in” on career concerns or not is an empowering decision, and there are all kinds of considerations to take into account when doing so. A choice to let them in, though, can often be the first step toward truly committing to career transition and finding fulfillment.

Wouldn’t that be amazing?


Chris is the founder of Empowered Achievers, where she helps millennials build professional lives and small businesses that fulfill their true calling. Having worked in advertising with clients like Google, YouTube, and Expedia, she traded in the agency life for the world of talent development and culture. She created Empowered Achievers when she realized her deepest calling was to help others find their calling as well, and transition into a life of fulfillment doing work that they love. She was voted one of the Best Millennial Career Experts by PeopleMaven. Chris has articles in Thrive Global & Kivo Daily, and features on sites like Business News Daily and HelloGiggles.

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