A friend of mine was until recently the proud owner of one Arsenal share, given to him by his father.  Last summer the Arsenal takeover completed and, although he had never imagined he would sell his share in the club he loved, he consoled himself with the fact he had a a lump sum to spend on a family holiday of a lifetime.

"Don't forget the tax!" I reminded him.  "When were you given the share and what was it worth then?  You will need to know that to work out the capital gain."

But he had not got around to thinking about his 2017/18 tax return yet - the 2018/19 return was too far away to worry about.  He would book the flights and worry about the tax bill (whatever it might be) later.

In advance of its Making Tax Digital initiative, HMRC is already encouraging real time reporting of capital gains, and provides a paper-based "post transaction valuation checking service". However, for many people tax is something that is sorted out in a rush just before submission deadline - when time and HMRC's resources to provide assistance may be in short supply.

Technology must be the answer here.  Surely it would have been preferable for my friend to go on-line immediately and enter the receipt, and for a pop-up box to then ask him how and when he acquired the share and whether he needed help in getting a valuation?  It could have also indicated how much of that cash he should squirrel away to cover the eventual tax bill.

A big policy question is how far we would want to go to make our lives easier.  Should Arsenal have been required to notify HMRC of the details of all the sellers and how much they received?  Should my friend's bank have notified the receipt?  Should the tax system have real-time access to his bank statements and other financial information?   All this would allow his tax account to be pre-populated with financial information, but at some point most of us would say that that goes too far.  

We will need to find the right balance between convenience and confidentiality of our finances, but there must be a way for technology to help avoid the current annual tax return panic.