Should I Stay or Should I Go Now? What to Do When Your Job Clashes with Your Mental Health

Kyla Duffy
5 min readJun 25, 2023

A towel in my mom’s kitchen says, “Bloom where you’re planted.”

This mantra got me thinking about a close relative’s career dilemma.

She was a server for the majority of her career. In her 50s, she got a shot at SaaS sales and lept on it.

At first, the learning curve was rocky. While she had strong selling skills, the technology was new to her.

For a while, things looked grim. She was constantly teetering on the edge of a PIP (performance improvement plan — the precursor to a severance package, if you know what I mean).

Nearly a year in, she rallied. Something just clicked, and she catapulted to top salesperson out of about 40.

Since then, she’s been a sales leader month over month.

Sounds rosy, right?

Not really. It’s come back down to a struggle recently, and she’s barely keeping her head above water.

Why? Even though the company’s been around for a while, it seems to be in perpetual start-up mode, forever trapped in growing pains and not quite getting it together.

Consultants come and go. Methodologies, CRM technologies, and expectations constantly change.

Communication is less than transparent. In fact, it seems like sales results are deliberately hidden so the house can skim their salespeople.

How crappy is that?

But, it’s base + salary, meaning there’s steady income, and hey, it could always be worse, right?

Is there a way for her to find some kind of water and sunshine to “bloom where she is planted”?


I have seen clients go from bad to worse.

But I have also seen people move from bad to better.

So what should my relative be thinking about when considering, in the eternal words of The Clash, “Should I stay or should I go now?”

1: How bad is it?

· Do you feel energized or drained when thinking about going to work tomorrow?



Kyla Duffy

Energized by “A-ha!” moments, I’m a career coach and resume writer who helps people move toward happiness & fulfillment. Get help at