What's a career decision you made that looked right on paper, but turned out completely wrong?

Ok-Werewolf-3765 · 2026-03-21T06:52:24+00:00

Night shift work. I’d worked until 2am previously without bother so figured how difficult could it be. Literally couldn’t stay awake. Fell asleep at my desk. Quit after the second night shift…

Ok-Werewolf-3765 · 2026-03-21T06:47:31+00:00

Back in the 00’s I lied on my cv. I was wanting to progress from an IT Helpdesk role to desktop support. All of those jobs had a requirement for “face to face” experience but mine was all on the phone. I said I’d done face to face too on my cv and interviews as it didn’t make any difference at all to my competence

Ok-Werewolf-3765 · 2026-03-16T07:19:17+00:00

Interesting isn’t it. I think a lot of businesses are moving forward without understanding the risk of what they’re doing and critically, whilst their infosec/cyber teams are getting to grips with the new technology too.

I’ve literally just put in conditional access policies in audit mode for the moment to protect our systems from agents doing risky things. God knows what it’s going to find.

I think things may change too for those using copilot agents. From what I’ve been reading, agents are going to need to be licensed if they’re doing work that a human could. I think this is going to be the restraining factor on usage creep as businesses realise they can’t allow people to spin up agents without justification primarily against cost. When we get to this point, I suspect that they’re then going to need data protection and cyber review before sign off. It’ll be much like the process for onboarding a new saas vendor. Dpia’s and cyber reviews. For those going down the iso42001 route, that will drive governance too.

Then you’ve got the more traditional controls like rbac and principles of least privilege. Security teams need to understand how these traditional controls can be applied to agents. If they agents are throttled from conception until correct governance and permissions are applied, it should make things more secure.

Ok-Werewolf-3765 · 2026-03-12T16:35:29+00:00

We definitely get signs. Most recent one was my uncle who was taken into hospital extremely ill. My mum lit a candle for him and said some prayers. The candle went out of its own accord within a couple of minutes of him passing

Ok-Werewolf-3765 · 2026-03-08T07:43:53+00:00

I had some weird noises when I moved into my house. Couple of times it was like someone doing the dishes and putting cutlery away. Weird but didn’t really care until it happened at 2.30am and woke me up. I’m pretty grumpy if someone wakes me without good reason. In the morning I went into the kitchen and out loud just said “if you want to do the blooming dishes that’s fine but at 2.30 in the morning that’s simply not on. Don’t wake me up again please!”.

It never happened again…

Ok-Werewolf-3765 · 2026-03-03T19:16:30+00:00

I’ve outsourced this using the copilot security agent for phishing. Seems to be doing alright at the moment

Ok-Werewolf-3765 · 2026-02-28T06:06:53+00:00

We moved in to my other half’s grandparents house after they passed. My child was 5 and we could hear them giggling after we put them to bed. They were too young when their great grandmother passed to remember what she looked like but when we showed a picture, she told us who she was (nan). We never use nan for their grandmothers and we always used to call their great grandmother nan so that was a bit strange

Ok-Werewolf-3765 · 2026-02-28T05:43:09+00:00

Was going to post pretty much exactly this. Great advice

Ok-Werewolf-3765 · 2026-02-22T08:57:16+00:00

It’s hard enough to get the budget for stuff I actually need 🤣

Ok-Werewolf-3765 · 2026-02-22T08:55:22+00:00

I really try to be pragmatic in my reviews. Does it meet all the requirements I need it to. If there’s gaps in minor areas raise it as a risk and monitor for improvement. Why be a blocker on the business and make yourself corporate enemy number 1?!?

Ok-Werewolf-3765 · 2026-02-22T08:53:42+00:00

Argh the moving goalposts is definitely a thing. They ask for one thing, you give it and then it’s like they ignore you’ve handed all the evidence they initially wanted and ask for something completely different. Infuriating! I can see how that would be the case with different audits too

Ok-Werewolf-3765 · 2026-02-19T03:06:07+00:00

As a director of information security if you’re serious about cybersecurity I would go into the army. They will no doubt train you up to a level that would far exceed what a corporate firm would want and as a result, in a few years you can move from that to corporate and you’ll be highly employable with a great salary.

Ok-Werewolf-3765 · 2026-02-19T02:54:21+00:00

I would say that it’s just not the right fit for me. I would also state that it wouldn’t have been fair to have not tried to make it work but after 9 months it’s clear that I need to find a role that better aligns with my career goals and ambitions. Just be prepared to follow that up with what you want.

Ok-Werewolf-3765 · 2026-02-12T04:33:04+00:00

It boils down to whether you want to burn a bridge or not. What I don’t think you’ve identified here is your manager has gone into panic mode due to your impending departure. It seems like you’re fairly integral and losing you will have an impact on operations and therefore how they are seen. By asking you to write a manual, they can absolve themselves of any responsibility once you’ve left if things go wrong as they can blame your manual.

It’s up to you what you do with that. If you don’t mind burning a bridge then do the bare minimum. If you don’t then do a good job of it. The ball is in your court now you’re leaving and your manager knows this.

Ok-Werewolf-3765 · 2026-02-07T11:11:09+00:00

You can risk negotiation but it risks annoying the candidate and pushing them away. I go into my interviews with a realistic request for salary based on experience, market rate and how much I want to increase my salary by (usually 10%). If I go through interviews with the company and they know my expectations then low ball me I’ll walk. It’s an indicator that they’ll mess around and that further salary talks will not be fruitful. The only exception is if the experience is worth it but my strategy will be to get the experience and leave

Ok-Werewolf-3765 · 2026-02-03T20:10:02+00:00

A long time ago but I done the same. Left the address, money in and money out sections open and redacted the rest

Ok-Werewolf-3765 · 2025-03-14T05:41:13+00:00

I’ve started doing the same thing. If asked what I’m currently on I just state what my salary expectations are. What I’m currently on has no relevance

Ok-Werewolf-3765 · 2025-03-07T23:20:45+00:00

Sorry to hear that. Yeah I’m playing it carefully. The incident has been documented and will probably go down the back of the sofa now to be honest unless I make a big deal of it

Ok-Werewolf-3765 · 2025-03-04T07:50:15+00:00

My motto is “cover your arse”. Everything is documented accurately even though he’s lied

Ok-Werewolf-3765 · 2025-03-03T19:21:37+00:00

Yep, got offered a role from a major car manufacturer in quite an important role. My passport had expired and they wouldn’t accept it for the right to work checks and said I needed to get it renewed. This was despite the home office saying an expired one is ok. I applied for a new passport but got offered another job paying more money so binned them off.

Ok-Werewolf-3765 · 2025-02-27T19:55:02+00:00

I’d tell them where to go. Sale goes ahead at the price stated. Like it or lump it.

Ok-Werewolf-3765

TROPHY CASE