AskUncleGary.com

Sign in Subscribe

Career

Work can bring purpose, independence, and satisfaction, but it can also raise difficult questions about direction, ambition, and workplace dynamics. In this section, Uncle Gary answers reader questions about careers, professional challenges, and navigating the realities of the working world.

Is it reckless to walk away?

Is it reckless to walk away?

Dear Uncle Gary, I’m stuck in a job that pays well but drains my soul. Is it reckless to walk away without a backup plan? Signed, Reckless Dear Reckless, You're absolutely right, it’s not just reckless, it’s potentially self-sabotaging. In this economy, walking away

https://www.askunclegary.com

A wig closet full of biohazards...

I’m trying to stay professional, but this feels like a sinking ship. Do I stick it out and finish the tour, or cut my losses before the wigs start crawling away?

https://www.askunclegary.com

I’m 38, single, and I’ve built a life that looks pretty good on paper...

I never really wanted the white-picket-fence life, but now I’m wondering if I skipped too many chapters.

https://www.askunclegary.com

I was a research scientist...

Dear Uncle Gary, I was a research scientist at a major pharmaceutical company until I got laid off. My wife is an attorney at a top law firm, and she’s doing very well. When the layoff happened, we talked it through and agreed I’d stay home with the

https://www.askunclegary.com

I was laid off last month...

Dear Uncle Gary, I was laid off last month from my job as a university administrator. I didn’t tell my wife right away because I truly believed I’d find something quickly and then explain it once I had good news to soften the blow. But here we are,

https://www.askunclegary.com

I just started an amazing job...

Dear Uncle Gary, I just started an amazing job as an assistant to a very successful hairstylist in Newport Beach. He’s super busy, well-known, and I was thrilled to be hired. About a month in, he asked me out. I froze. A few days earlier, he’d asked