My worst financial decision

1. Not taking up a career in the City.
2. Following conventional wisdom and putting money into Equitable Life. (Got most of it out before the grisly end - the only good advice my then financial adviser gave me.)
3. Missing out on the gold price hike.
4. Ditto the above with every other boom.
But I'm not complaining

Wha? Sorry, wasn't listening...

Buying a share in overvalued joint equity property with an endowment mortgage just at the peak of the market in 1990.

Though thanks to a error by the local authority, and the threat of a class action against them it all turned out in my favour.

The properties were developed and sold by the local authority as joint equity at £32,000 for a 50% share which valued them at £64,000 about £10,000 above the freehold value of equivalent properties so we were effectively in negative equity even before the market crashed. When purchased there was a peppercorn ground rent (described as such in the lease) on the half that was not owned, however over a period of about 6 years this peppercorn rent rose to such a point that it was the same as residents were paying for their mortgages. During this period the LA had always claimed that the properties were outside the normal social housing stock however we discovered they were treating them as social housing stock when calculating the ground rent increases hence the phenomenal increases. Armed with this information the newly form residents' association put an ultimatum to the LA either include the properties in the social housing stock and give us the right to buy discounts, recalculate the rent increases using a separate process that kept the rent as a peppercorn rent and rebate the over charging or face a class action. The LA capitulated by doing not what we had demanded but by setting up a separate scheme which allowed us to purchase the remaining 50% at market price (a right we always had) but with a discount equivalent to the right to buy discounts in operation at the time. Given the depressed house prices, and the discount most of us bought the freehold at a price which meant that we went overnight from having negative equity to positive equity in the properties and our monthly outgoings dropped because resulting mortgage payments were less than the previous mortgage payments plus the ground rent.   

and the key takeaway from that is that we SHOULD listen to anything batchoy says.

My worst ever financial decision ? Not buying the winning ticket on the other weeks Euro Millions. (or whatever it is called)

A more serious worst financial decision: taking out an endowment when buying my first place. Add to that, I went through a friend who worked for a major company. That person couldn't sell directly so it was routed through an IFA. They weren't meant to have done this (I guess they weren't meant to give me "advice").  I got half the comissions back up front (good). But when the s**t hit the fan on endowments, I felt I couldn't open up the pandora's box in case it had some fallout on my friend (even though she was no longer there). So I never benefited from the compensation when I almost certainly could have. To make matters worse, I realised/discoverd a few years ago that it was a non-qualifying policy, which I'm told is pretty unusual for an endowment to cover a mortgage. So any gains are income tax chargeable at a wonderful tax rate. It is still running: a few, but not many years to run. I've almost cashed it in a few times: also got 3/4 of the way to at least stopping payments into it, but somehow paper work never seemed to quite get sorted. Would have been better had I cashed it in. Plus of course releasing me from stupid b****Y fees. But somehow its never quite happened.

And to think that every pore of my body was telling me 'repayment mortgage'.

Still, at least that mortgage was paid off a long time ago. Just as well, as the endowment is going to struggle to hit 35-40% of the value that it was meant to give.

My worst mistake was to buy pep funds from Legg Mason, one was called Hy1 and invested in the first or maybe second highest yielding share in the FTSE 30, as a single company pep, a theory of Jim Slater which ended up worthless when it chose Marconi.   The other was managed by his son Mark Slater and had lost 2 thirds of it's value after 6 years.   It was called the Slater Growth Trust.