Everyone in the office younger than you? How not to become Mr. Wilson


“Dennis the Menace” 1959

If you’re over forty and working with startups or cutting edge technology, sooner or later you’re going to find yourself being the oldest person in the room.  Don’t be the curmudgeonly Mr. or Mrs. Wilson of the office!

Being the most “mature” person may be inevitable but it doesn’t have to be a bad thing.  American culture is generally youth obsessed, but there’s a lot to be said for experience.  Your knowledge and history mean that you can help new businesses avoid pitfalls that companies have made before them. Startups need your expertise.  Just check out SweatEquitE.com to see how much.

So while you’re guiding your associates to greatness, how do you avoid relationship faux pas with the “young whippersnappers”?

Rule 1:  Show some respect! First, maybe don’t call them whippersnappers or millennials or kids.  These are your colleagues, not your children (or your grandchildren). Don’t refer to them by labels.  Colleagues are colleagues and should be respected as such. Just because they are younger doesn’t mean you have to act as their parent. Don’t patronize or condescend, and be open minded to doing things differently. A little diplomacy can go a long way and despite your experience, it’s quite possible that you may actually learn something new.

Rule 2:  Watch your language!  Don’t try to be cool, oMature rapper holding a ghetto blaster and looking at the camera isolated on white backgroundr hip or rad or whatever.  Every generation has its own set of slang and to those outside, it feels like a new language.  It’s a good idea to understand it, but probably not a good idea to try and speak it.   Know what being on fleek means? Still saying jiggy? Even if you get the context right, it sounds like you’re trying too hard and terms change faster than Taylor Swift boyfriends.  (See!  Trying too hard.)

Unfortunately, this works another way, too.  Or actually, doesn’t work.  Be careful not to pepper your speech with your generational slang.  What sounds normal to you will sound weird to them also.  Got it?  Out of sight, dynamite!

Rule 3:  Stay off my lawn!  It can be hard when your boss is younger than you, but stay off his or her lawn.  Don’t try to usurp authority.  Yes, you know a lot but no one likes the office know-it-all.  Pick and choose when and how to add your knowledge. Coaching and counseling are better received than lecturing, especially to your boss.  Your experience is an asset, but you still have to follow office rules and protocol.

Rule 5:  Are you wearing that?  It can be tempting to assimilate to office culture by wearing exactly what the younger set is wearing.  It can also be tempting to wear what you wore to work twenty years ago. Don’t do either!  You certainly want to fit in, but styles meant for 20-something tastes usually don’t translate well to bodies twice or thrice that age.  Modernize your wardrobe, but you should be comfortable in your own skin.  Add flair without becoming a parody.

For example, if everyone is wearing shorts and flip flops, maybe a cute pair of sandals instead.  Just don’t wear socks…


black socks with sandals








unless they’re really cool socks.

Legs of woman with high heels dressed green dress vintage style outdoor






Not sure if you’re doing it right?  Ask a trusted confidante or try out a department store that provides free personal shoppers.  Another way to keep current is to watch a popular TV show and see how the characters dress.  It’s worth the time (even if you have to mute the dialogue!).

However you decide to move to a new experience, make it fun!  You’re only as old as you feel.

Comments (8)

  • Steve Wolfe

    September 21, 2016 at 9:29 am

    Great read! It’s important NOT to be the Old Fart in the office – even if you actually are!

  • Paul Adams

    September 21, 2016 at 9:31 am

    It’s often tough for an old….errrr…. experienced person to realize that younger colleagues are not your children and that they’ve got talent too! Thanks for the reminder!

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