When Job-Hopping Leads To The Wrong Kind Of Connection

I’ve changed jobs so many times that if I tried counting them on my fingers, I’d run out pretty fast. Some people stay with one or two companies their entire lives, building a neat little ladder of promotions and responsibilities. Me? I’ve hopped around so much that my résumé looks like a travel map. But there’s something interesting about changing jobs so frequently: you get to meet all kinds of people along the way. Some are genuinely nice, some are cool and fun to be around, some are horrible to work with, and some are just downright creepy. And every once in a while, you encounter someone who sticks with you long after you’ve moved on — not because they made a positive impact, but because the encounter left a lingering discomfort you can’t quite shake off.

One of those people for me was a former manager. And the weird part is, I didn’t even work with him for long. In fact, he submitted his resignation the very day I started the job. So technically, he wasn’t even my manager for more than a few hours. But somehow, for reasons I can’t fully explain even now, our paths ended up staying connected for months after he left the company. At first, it seemed harmless — maybe even helpful — but eventually, the whole situation spiraled into something that still gives me the creeps when I think about it.

How It Started

When I first joined the company, he was the kind of person everyone seemed to respect. He had years of experience, knew every nook and cranny of the industry, and had that confident, polished way of talking that people tend to interpret as leadership. Even though he had already resigned, he made an effort to introduce himself to me before heading out for good. We exchanged a few words, and later on, we connected through email. Nothing unusual — just friendly exchanges, occasional updates, or small pieces of advice about navigating the new job.

Since he carried so much industry knowledge, I naturally gravitated toward him as someone I could ask for guidance. When you’re new to a company and new to a particular role, you cling to whatever sources of insight you can find. And here was someone who didn’t just know the job, but also had no stake in the internal politics anymore. That made it feel safe — like he could give unbiased advice without worrying about stepping on any toes.

We started meeting up occasionally after work. A quick drink here, a short conversation there. We usually talked about whatever issues I was dealing with at the company. He’d listen, offer feedback, and sometimes laugh at the ridiculousness of things he once dealt with himself. In the beginning, it was genuinely helpful. It felt like mentorship, like someone was taking the time to help me steer my career in the right direction.

When he moved on to a new company, our conversations shifted from my problems at the old job to broader career topics. We’d meet for lunch or dinner, and he’d give me advice about job openings, possible opportunities, or skills he thought I should develop. Once again, nothing felt off. Just two working professionals discussing careers, goals, and industry trends.

But looking back now, I realize I missed some red flags.

When Things Started Turning

At first the meetings were occasional. Then they became more frequent. And soon, he always wanted to meet one-on-one — no casual group meetups, no grabbing a drink with other colleagues, no inviting mutual acquaintances. He always insisted on it being the two of us.

Even then, I brushed it off. Maybe he preferred focused conversations. Maybe he was just introverted. Maybe he just liked keeping things private. I didn’t think too deeply about it.

But then came the dinner that changed everything.

We were talking about my job — the usual venting about frustrations, pressure, new responsibilities, and confusion about what direction I wanted my career to go in. He was no longer with the company, but he still seemed unusually invested in everything that was happening with me. He’d offer comfort, reassurance, and sometimes a bit too much sympathy. But again, I ignored it. I was looking for guidance, and he seemed willing to provide it.

But when dinner ended and we got up to leave, things took a turn.

As we walked outside, he reached over and started rubbing his hand across my back — slowly, deliberately — and then along the back of my neck. Not a friendly pat. Not a casual gesture. Something else. Something that instantly triggered that internal alarm we all have but sometimes try to mute.

It was the kind of touch that makes your whole body stiffen. You don’t want to react too strongly because you’re trying to make sense of what’s happening, but every part of your instincts is screaming that something’s wrong.

I remember stepping away slightly, pretending I needed to adjust something or grab my phone. He didn’t say anything, and I didn’t confront him. I wish I had. But in the moment, I just felt uncomfortable, confused, and frankly, stunned. This was someone I thought I could trust — someone I viewed as a mentor. And suddenly, it felt like all those months of “guidance” were something else entirely.

When It Crossed The Line

After that evening, things didn’t go back to normal. In fact, they got worse.

He wanted to meet again — right away. Then he insisted on picking me up himself to make things “easier.” He didn’t ask if I needed a ride; he pushed for it. That’s when my discomfort shifted into something heavier: unease, suspicion, even fear. Why was he so intent on seeing me alone? Why was he trying to control the logistics of the meetup?

I kept thinking back to all the times he insisted we meet one-on-one. All the sympathetic conversations. All the overly personal questions disguised as career advice. Suddenly, the pattern made sense — and not in a good way.

I realized then that the mentorship I thought I was receiving was something else entirely in his mind. Or maybe he blurred the lines without saying it. Either way, I didn’t like where it was heading, and I definitely didn’t feel safe anymore.

So I did the only thing that felt right: I stopped responding. No explanations. No long messages. I just cut the connection.

Maybe it seemed abrupt from his perspective, but for me, it was self-protection. And honestly, I don’t regret a single bit of it.

Lessons I Learned — The Hard Way

That encounter taught me a lot about boundaries, especially in professional relationships. It made me realize that mentorship should never feel uncomfortable. You should never feel obligated to meet someone alone if you don’t want to. And most importantly, someone who is truly committed to helping your career doesn’t need private dinners, secret outings, or physical closeness to do it.

Some people take advantage of vulnerability — especially when they sense you’re going through stress, job uncertainty, or emotional ups and downs. And it doesn’t matter if the person is a manager, former manager, coworker, friend, or mentor. The moment you feel unsafe or uneasy, that’s all the reason you need to take a step back.

No job connection is worth your safety or peace of mind.

Looking back, I don’t blame myself for missing the signs. When you’re early in your career — or even years into it — you want guidance. You want someone to show you the path ahead. And sometimes you give people the benefit of the doubt because you think they’re genuinely trying to help.

But real guidance never comes with hidden intentions. A manager’s role — past or present — isn’t to build personal connections that cross boundaries. Their job is to provide advice, support your professional growth, and help steer the next generation in the right direction. Anything beyond that is unnecessary, and in some cases, inappropriate.

If you ever find yourself in a situation where someone who was supposed to help you starts making you feel uneasy, trust your instincts. They’re there for a reason.

And if you ever feel unsafe?

Walk away.

Cut contact.

Don’t look back.

You don’t owe anyone access to your time, comfort, or personal space — no matter what title they hold.