Q. I work for a marketing company, and a long-time client has asked me whether I'd be interested in doing some freelance work on the side.
I am tempted because they will pay me well (I could really do with the money), and it could be an interesting project. But if I take it, I'm worried that my manager will find out. Strictly speaking, I'm not meant to do any work like this and I'm afraid that I could be sacked for it. Should I take it?
A It's interesting the way we use the phrase 'strictly speaking'. 'Strictly speaking, I've given up desserts.' 'Strictly speaking, it's my turn to do the school run.' And what we actually mean is, just this once, we'll cry off the school run and have a bit of Black Forest gateau.
Strictly speaking, you're not meant to do any freelance work - but, just this once, you're thinking about it. And the only thing that's making you hesitate is the thought of being found out.
You need to think this through from the beginning. What this long-term client is hoping to do is bypass your company and get a chunk of your valued time on the cheap. However generously he pays you, it will cost him less than your company's charge-out rate. He's perfectly entitled to try this on, of course, but it seems a bit shifty and it certainly puts you in a difficult position.
Tell your client that you greatly appreciate the suggestion and that you'd love to do it, but your contract forbids it. However, it's possible that your boss would agree to make an exception, so is it OK if you put it to him?
If your client insists on keeping the deal a secret, your decision makes itself. It's a pity about the money, but the alternative is a nightmare future of guilt, furtiveness and fear.
If he gives you the thumbs-up, however, you can put the proposition openly to your boss.
My guess is he won't take kindly to the thought; to him, it will look as if you're doing him out of a bit of legitimate business. He will also suspect that you would do the client's freelance work during normal office hours, but he'd probably have enough sense to refrain from saying so.
Should he say no, take his decision with good grace. At the very least, you'll have registered the fact that the client rates you highly and that you could do with more money.
Q. The HR administration where I work is really lax. No-one keeps track of how much holiday we've taken. I strongly suspect that one of my colleagues is playing the system and taking more holiday than he is allowed. I'm ashamed to say that I don't want to grass him up. In fact, I'm very tempted to take more days off myself. We don't get paid very much and I think of it as fair compensation. If they're getting away with it, why can't I?
A. Forgive me if I move into schoolmasterly mode. A set of rules that are clearly understood and consistently maintained may feel restrictive at times, but in any organisation, their absence is infinitely worse.
Follow your present instinct and you will soon start wallowing in uncertainty, guilt and self-justification. If your low pay justifies you in stealing time from your company (and please don't reach for the euphemisms) how many days are you justified in stealing? It shouldn't be left to you to decide. Next, you'll be calling up your cousin in New Zealand on the office phone and taking home a handful of teabags.
You don't have to grass on anyone. You should double-check your holiday entitlement with your HR director and then suggest that he or she posts a holiday roster on the notice board so that everyone can plan their work more easily.
When standards of office behaviour start to get all loose and flaky, it doesn't spell freedom; it breeds envy, suspicion, rumour and a surprising amount of real unhappiness.
Q. I've been invited to an industry conference that includes a gala dinner in the evening at the Savoy hotel in London. The invitation says we can bring a guest. I'm single at the moment and want to take my father.
Since my mother died, he doesn't really get out much and I'm sure he'd like going up to the city for a swish dinner. Do you think it would be OK if I brought him, or is that a bit sad? I'm worried people will think I'm a bit of a teenager. I'm 34.
A. I think it's a wonderful idea - and once you've run through a brief mental checklist, I'd urge you to go for it.
First thing: don't give more than a moment's thought to what other people may think of you. Maybe they'll think: 'Poor old Sonia, hasn't got a man of her own so had to bring her Dad', or 'Poor little Sonia, still needs her Daddy to hold her hand'. But the chances are, they'll think none of those things.
The person that you've got to consider more carefully is your father.
To him, the prospect of going to a swish dinner might seem wonderfully exciting, but the reality could be a bit of a nightmare - particularly if he's surrounded by a bunch of well-oiled bond salesmen, all of them about 40 years younger than him, and indulging in the completely incomprehensible banter of bond salesmen.
So the obvious point - which I'm sure you've thought through - is this.
Just be sure in your own mind that there'll be a few compatible companions nearby, and that your father will be able, naturally and comfortably, to join in the conversation and not just sit there in mute and miserable isolation.
Jeremy Bullmore has been creative director and chairman of J Walter Thompson London and a non-executive director of both the Guardian Media Group and WPP. Address your problems to Jeremy Bullmore at: email@example.com. Regrettably, no correspondence can be entered into.