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I’ve just paid my tax bill and the coffers look distinctly bare. It’s so depressing. I have come to a stark conclusion: I don’t have enough money.

Enough money for what exactly? Do I need more money or do I want more money? And who can I speak to about my dilemma? You cannot possibly air these thoughts in public (unless you have no filter or a regular column in which to vent in the personal finance pages).

No one else needs to know how much you’re paid. Or what your pension is worth, or how much your tax bill is. Or anything on your personal shopping list. And, more importantly, nor do they care. Either they have more money than you so will be embarrassed by your predicament or have less and wonder what you are worried about.

For one section of society, though, public discussion is unavoidable. Those at the top end of public life have all of these facts revealed in company reports or tabloid newspapers. Harry, for instance, had a face-off with his granny over not wishing to join the family business. Now he’s got to pay the £2.4m back that he’d spent doing up the house he never really moved into. Meanwhile, he’s got to find a new place to live. But cash doesn’t, as yet, seem to be the chief problem in that particular saga.

The more I think about my own financial situation, the more I am reminded just how much money I don’t have. It’s not as if I don’t have a roof over my head. But it’s not totally waterproof at the moment — that’s because of the hole left by Storm Brendan. Thanks for nothing, Brendan!

The insurance company has been very responsive and says it’ll cover whatever needs repainting, redecorating, fixing or sorting. It is a bit of a bother that I have to spend time that should be devoted to other projects on organising this. However, the insurance premium was definitely a worthwhile investment.

Although the house is a lovely place to live, should I be concerned that I can’t afford something a little more lavish? And those projects to kit out the downstairs loo with Bert & May tiles and the walk-in dressing room will just have to wait. But they aren’t exactly urgent.

There’s always room in the garage for another car, isn’t there? Maybe, but the lack of available funds means it isn’t an immediate possibility. I currently have my eyes on a late 1980s Mercedes R107. Although other cars have come and gone over the years this is one modern classic I’d like to add to the stable. For whatever reason I’ve never done it. And now, even if the right one did come along, the money isn’t in the bank account to do it.

At breakfast the other day, I experienced the full service experience at the Chiltern Firehouse in Marylebone. I was meeting a friend. He’s the chief executive of a company, with more money than God. What he earns and the life he leads means every spare penny is accounted for.

Initially I didn’t realise that the reason I’d been asked to breakfast was that he wants to buy a new car and he thinks he wants an Aston Martin. He, like you, knows that I have been an Aston driver for 20 years. He’s unsure as to whether he can afford it and wants a second opinion.

Yes, if I had the money, I’d buy a new one. Or even better a very old one. Or both. But would I feel happy driving something around that’s as valuable as a small flat in the Alps or a mews house? After all, the one I have is in wonderful condition, has just had its seats restored and is one of the nicest cars I have ever driven. Should I be concerned that I cannot buy every car I set my eyes on? The avocado on brown toast with poached eggs and a little smoked salmon on the side is delicious, by the way.

At this time of year, when everything is utterly grim, it’s time to plan your holidays. That’s why Blue Monday, the most miserable day of the year, was invented by some PR guru to encourage us to make those plans. The thing is, you have to pay for everything up front and I am concerned by the lack of available funds — even though there are some really good sale prices on at the moment.

I was slightly taken aback by the six grand it appears to cost to go upper or first class on a flight to New York. The £700 or so premium economy that I scouted seems like good value. After all, if you’re just popping over for the weekend, do you really need to turn left?

If you are my friend who had to go to a wedding for the weekend, the answer would appear to be yes. The thick end of £50,000 later, he’s been there and back with the family, and still looks like death dug up because he couldn’t sleep properly on the plane’s flat beds on the way home. That was mostly, he said, because he was worrying about the bonus incentives on his package and whether they’d cough up.

The clearing out of my bank account by HM Revenue & Customs is a twice-yearly event. As someone who is freelance it’s particularly painful in January. But no, I am not on the streets. If I go to Aldi, it’s by choice. And talking of choice I have a range of clothes to wear. There’s a fat wardrobe (filled with Ralph “custom” or fat fit clothes) and an optimistically thin wardrobe (filled with “slim fit” designer items). Of course there’s also a midlife crisis wardrobe (which is where the Balenciaga shoes live).

We sometimes forget that “rich” is a relative term. It’s also one that at times seems meaningless when you see pictures of people who have lost everything because of a natural disaster, or can’t travel because they genuinely don’t have the money or live in a country that won’t allow them to do so.

This is why we should focus on what we have rather than what we don’t, and realise that with some hard graft and entrepreneurial spirit the bank account can be filled again. I’d better get back to work. 

James Max is a property expert and radio presenter. The views expressed are personal. Twitter: @thejamesmax. If you have a problem for James, contact him at richpeoplesproblems@ft.com

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