How to Succeed When You're the Oldest Person at Work


"How long has your show been on the radio?" asked one of my much younger bosses recently. I wanted to answer: "Longer than you've been alive." The flippant reply would have allowed us to pretend for a little while longer that I'm not old enough to have given birth to her without scandal, but it would not have helped build professional rapport. Instead I told her the truth: "Twenty-nine years." Then I watched my Music Director's face while she made the mental calculation. "Wow," she said. "You look good."

If you work long enough in any industry where technological change is a factor, you will eventually end up working for a boss that is younger, sometimes much younger, than you. While cross-generational friction is bound to happen, it's part of your job, older worker, to support your boss, regardless of their youth. But how do you set aside your ego and your age and focus on the work?

Don't conflate age and experience

Just because your boss is the age of your child doesn't mean that they don't have the right skill set to manage or mentor you.

I learned how to edit film on a Moviola and manually sync footage with a block counter when I was 20 years old. The editors I assist nowadays didn't have to wait until film school to learn how to edit video. They started learning at least one professional editing program in middle school. While I have had to learn every new digital editing system on the fly, all of my younger bosses are expert digital editors because they spent four years in high school and another four years in college learning every nook and cranny of Avid and Premiere.

They may be younger, but they have years of experience on me in terms of the technology. This is humbling. That said, my child overlords are constantly teaching me new shortcuts and hacks, which help keep my skills up to date.

Do your job

As a worker, your job is to meet company goals and deadlines. Your job doesn't change based on the age of your boss. In order to be an effective worker, you have to build a solid relationship with your boss whether they are young or old.

Every boss is going to have shortcomings, blind spots, and eccentricities. Whatever the age difference, it will always be part of your job to find workarounds that will help both of you successfully drive business forward. Focus on your own productivity and build a relationship with your superiors based on your own success.

Ageism goes both ways

I am not going to pretend that ageism doesn't exist, especially for women. It's a real issue in every industry and it's sucky and wrong.

That said, don't assume that your boss is going to be a bad manager just because they are younger than you. Judging your boss by their age and not their skill set is ageism, too.

It is entirely possible that your whippersnapper manager is also uncomfortable with the age difference between you. Recognize that it might be hard for them to give orders to someone they might see as a respected elder.

Instead of focusing on generational differences, focus on your similarities. Both you and your boss chose to work at the same company. Why? Finding that common ground can be the basis of a great working relationship.

Use your experience to manage up

Although it can be disconcerting to always be the oldest person at the office, know that your continued employment actually means that your employer values things like "life experience" and "creative continuity," abilities that your younger bosses have yet to unlock. One of the best skills you can bring to the table is your experience.

However, when your young boss is floundering, it isn't helpful to point out the problem. Not only are they profoundly aware of the issue, telling them something they already know can make you sound like a nagging parent, and not like a supportive problem solver.

My work experience gives me credibility with my younger coworkers, but I know (from experience) that no one likes getting the "back in my day" lecture. When I am asked to impart wisdom, I always try to approach it from the angle of what I learned from previous experiences.

I have found that it's always better to advise rather than give advice … to anyone seeking a solution. What is the difference? Advising is giving my boss the lowdown on how I successfully managed an aggressive blowhard director in the past, and asking her how she'd like to resolve the situation. Giving advice is telling her how to manage Mr. Blowhard.

Don't let assumptions be the ruin of you

If you are horrified to find yourself reporting to a younger manager, ask yourself why you think their authority isn't legitimate. Are they actually bad at their job or are you mad because you think seniority should count for more?

Also, be honest: Would you be upset taking orders from a younger person outside of work? For example, if you were learning how to surf, would you question the ability of your 20-something surfing instructor?

I have a distant relative who is trying to get back into the workforce after a few years of leave. She is having a hard time and has been turned down from tons of jobs — everything from nursing assistant at the local hospital to the Whole Foods deli counter. She rails about the ageism she feels. She is sure all these employers are looking only to hire young people who, in her words, "Don't ask questions."

Although ageism is totally a real and disgusting thing, I am 100 percent sure that the real reason she's not getting hired is because her Facebook page is public and full of racist memes. She's clueless about privacy settings and completely unaware that companies regularly Google search potential employees and monitor their workers' Instagram feeds. It doesn't matter how polished she appears in the interview; her online identity is a wreck of bigotry and bad spelling.

If you are having problems with the kids these days, take steps to make sure the problem isn't you. If you can't play nice with an entire generation, it's probably a personal issue.

The work-life balance gets harder with age

I don't know a lot of old workaholics. When I was in my 20s, my equally young coworkers and I would extend our workdays beyond the office by going for drinks after work or even attending weekend parties together. The fact that my social life was embedded in my work life was a feature, not a bug of working in a creative, youth-driven industry. My job was a blast and my coworkers were some of my best friends.

Flash forward 20 years. While I still think my job is a blast, I don't want to spend 24/7 at the office. I am married, my former coworkers are now old married friends, and I have a fully realized adult identity that is not 95 percent based on my job description.

Still, after-work socializing is where a lot of networking is done, so I cannot forgo what I now perceive as extracurricular activity if I want to stay competitive. My friend cohort has aged, but my coworker cohort has not. If I decline too many social invitations outside of work, eventually my younger bosses will stop including me on projects at work because they don't want to have to repeat the brainstorming session they had with everyone else during happy hour.

To ensure that I have enough facetime with my officemates, I actively make time in my schedule to interface with my youthful bosses in the form of a drinks date every Monday night. In addition to catching up on all the weekend party gossip, Monday night drinks give me the chance to casually ask questions about upcoming work. Most importantly, it gives me a measure of control over my post-work, work life.

Although this is an effective scheduling workaround for me, this might not be a good time management solution for people who have to arrange for weekly child care around cocktails. Try to find a solution that works best for you and your schedule.

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