Red Flags I Missed in My Old Jobs—And What I Look for Now

For a long time, I thought high stress just came with the territory. If the hours were long, the pressure was relentless, and my boss was always one email away from a meltdown, I told myself that meant the job was important. That I was important. But eventually, that story stopped working.

Looking back now, I see so many red flags waving in the wind—some of them practically smacking me in the face. I didn’t recognize them at the time because they were so common in the environments I worked in. I thought it was normal. But normal doesn’t always mean healthy. It took leaving that world—and burning out more than once—to start noticing patterns.

Here are three big red flags I missed, and how I approach things differently now.

🚩 Red Flag #1: “Work-life balance” was just something we said out loud.

In more than one job, I was told that balance was a priority. But in practice? Everyone worked around the clock. Nights. Weekends. On vacations. Being reachable at all times was an unspoken rule. And if you tried to protect your time, even politely, it was seen as a lack of commitment.

What I look for now:I pay attention to how people actually live, not just what they say. Do people leave the office on time? Do they talk openly about time off—and are they encouraged to take it? Are deadlines realistic, or is “urgent” the default setting? I ask these questions in interviews. I listen to how the team describes their own pace. Culture shows up in the margins.

🚩 Red Flag #2: My boss was always in panic mode—and we all paid the price.

One of my former bosses was a brilliant operator—but he was also a human pressure cooker. Every minor setback triggered full-on stress spirals. It was like walking through a field of emotional landmines. You never knew when it would go off, or how badly you'd be hit. And we all absorbed it, because we didn’t have a choice.

What I look for now:Emotional regulation is a skill, not a luxury. I now value leaders who stay calm under pressure and model steady, grounded behavior. If a manager can’t self-regulate, it creates a culture of fear and unpredictability. I try to get a sense of emotional tone in interviews. How do people describe their leadership team? If I hear “intense,” “driven,” or “perfectionist” too many times, I read between the lines.

🚩 Red Flag #3: No win was ever good enough.

This one was the hardest to see while I was in it. I worked in a culture where client satisfaction (in my case, club members) was the ultimate metric—and the bar moved constantly. We could throw incredible events, hit every target, get glowing reviews… and the focus would still be on the one negative comment. There was no finish line, no moment to breathe. It was always, what’s next?

What I look for now:Healthy recognition. I want to work in places where people celebrate wins, not just survive them. Where appreciation is part of the culture—not a quarterly email. I look for environments that have perspective. Where a bad day doesn’t erase a good week. Where excellence is encouraged, but perfectionism isn’t worshipped.

What I’ve Learned

The biggest red flag, in hindsight, was how often I ignored my gut. When something felt off, I explained it away. I wanted to be loyal. I didn’t want to seem ungrateful. And if I’m being honest, I was scared of what it would mean to walk away.

But the truth is, we don’t get gold stars for staying in places that hurt us. We grow when we learn to see things clearly—and choose differently next time.

Now, I ask better questions. I take note of what people do, not just what they say. And I trust my gut when it says, this isn’t it.

Because no job is worth losing yourself for.