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Posted inDear Gabby

Which is better, a good therapist or a good hairstylist?

by Dear Gabby March 6th, 2022March 7th, 2022

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Dear Gabby,

My best friend is really unhappy in her job (and has been for years) and won’t stop complaining about it. I’m all for a good rant session, but she’s fixated on the idea that she’s already chosen her career and it’s too late to switch. She’s 28!!! I keep telling her that now’s the time to switch (not that you can’t in middle age), especially because she is thinking of getting pregnant in the next couple of years. Is there a way I can continue to support her while also helping her see the light?

A Tad Tired of Listening

Dear Tired,

Here’s the thing about advice: people only listen to it when they are ready to hear it. So if your friend is caught in some psychological cycling between hating her job and feeling unable to leave it, that is where she will likely stay until something causes her to see things differently. Perhaps an event, a therapist, a self-realization or even your supportive honesty coming at just the right time.

Trying to bolster her self-confidence can’t hurt, but statistics show that people change careers more often than they change their sheets, so it sounds like anxiety may have squeezed rationality out of her thought process.

Maybe you can get her to think about why she feels so stuck. Is it rational? A good therapist may help to get her unstuck. Like I always say, a great therapist is better than a good hairstylist (actually, they’re both pretty great), a worn pair of old jeans (maybe a toss-up) and generally worth their weight in high-quality, 72% cocoa, handcrafted, bean-to-bar dark chocolate (mos def!). And that’s saying something!


Dear Gabby,

My boss is exhibiting very strange, erratic behavior that many of us feel is indicative that he is not well. We have all worked together quite a while and we know each other quite well. 

We are so concerned and feel that he should not be able to use his password to get into the company’s system since he seems so unstable. We could go to the board, but that feels a little punitive or too too. We could go to HR, but that also feels sort of tattletale-ish. Alternatively, we could lock him out of his computer but that feels even worse. We’re at a loss – but open to suggestions.

Feeling Stuck

Dear Stuck,

It sounds like you and your colleagues have good reason to be very concerned about your boss. However, it is not up to you to solve the problem. It is up to you to alert someone who can be of aid. 

Depending on the structure and culture of your workplace, that could be someone on the board or it could be someone in HR or it might be both. If there is someone on the board who is compassionate and close to your boss, I might alert that person confidentially so that they can take it from there. 

If, however, the board is not close to your boss, I would go to HR. I was in the same boat once with a coworker. Since his behavior was so obviously unusual, the higher-ups came in right away and helped him out, fortunately with compassion. I hope yours will do the same.


Dear Gabby,

We own a rental, and our tenants want to paint a few rooms. We don’t love the colors they chose, but we want to keep them happy. Someday, though, they’ll move out and we’ll be stuck with colors that’ll be hard (and costly) to paint over. Any suggestions?

Even the Impressionists Had Their Critics

Dear Impressionist,

You are the owner and you could certainly restrict your tenant’s paint color choices, but honestly, why? You don’t know when they will move out and you could be worrying about something that won’t happen for 10 or 15 years. That seems like unnecessary anxiety. 

The fact is that by the time they move out, you will probably have to paint the place anyway, just to keep it fresh for the next tenants. Paint is expensive but it’s not that hard to paint an empty house. This is what bored college kids, home for the summer, are good for (and possibly not much else – other than sleeping too late, spending too much and reverting back to their 14-year-old selves).

Dear Gabby appears in the RoundTable every Monday. Yes, Gabby is an advice columnist – but not just any advice columnist. Because that would be boring! Gabby combines wisdom with wit. And a pinch of snark. She is not a trained therapist by any means, but has seen and loved many in her day. Her aim is to make you think while she makes you laugh. Gabby welcomes all questions and queries and is only too happy to hear your opinion, no matter how much it may diverge from hers. Write to Gabby at news@evanstonroundtable.com.

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Dear Gabby

Dear Gabby appears in the RoundTable every Monday. No question is too serious, too silly or too snarly for Gabby, who combines wisdom with wit and a pinch of snark. Her aim is to make you think while she... More by Dear Gabby

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