John,

Sounds like you need more than watches and cars to lift your life. However, you seem to be making some progress. Here are some further suggestions. Work out and lose some weight. Make those hidden muscles bulge. Get rid of that uncle haircut. Gel up some spiky hair and have some mild red highlights. With the new body, switch to tight shirts in shiny white cloth, Hugo Boss outfits. Fancy Prada shoes. Walk with a swagger.

At 38 and doing well, you can afford to take some risk. Clearly you will get to your financial targets if you continue the current job/lifestyle, but looks like you hate it. When you find your new job, see if you can take a 3-6 month break before starting then take an adventure vacation. Climb up the Nepal peaks. Trek down the Grand Canyon. Jump out of an airplane (or at least bungee jump) Learn to dive at the Great Barrier Reef. Rent and drive exotic cars (Lambos, Astons etc) in the UK. When you get back, you'll be ready to conquer the next peak and exceed your monetary forecasts.

Forget the Maseratis or Whizzard's Panamera. Get a 2 door sports car, like a 911, Audi R8 or Nissan GTR. When chicks see Maserati or Panamera, they think Uncle. When you wait at the light with a 911, R8 or GTR (more affordable), all the loose chicks give you that look. You feel like 24 again. The car goes with the swagger, tight shirts and fancy hair. Your Audi Q5 is a fast and nice family car so its no wonder you got bored after a few weeks. It's much more difficult to get bored of a supercar with its punishing ride, fantastic cornering and screaming engine. In fact, its the polar opposite of your Q5.

Don't pay off the debt on that investment property. That's what an Uncle would do and that's not what you want to be. With DBS willing to lend you at 1.5%, surely even conservative you can beat that. In fact, borrow more. A little leverage will allow you to reach your financial goals much faster.