I'm guilty of playing it safe too often. Now there are plus points to this, which people who take lots of risks don't realise. A lot of compulsive risk takers are partly 'fooled by randomness'... just because nothing bad has happened by them doing stupid uncalculated risks they imagine they can't. But they can... and when you're dead you're dead. Word up.
But being honest, I'm too cautious overall. There are some pretty basic things that I should do more that I don't because I'm not used to doing them. I'm taking steps to change that, but need to push more. A lot of so called 'risks' are just in your mind. I've done some things recently that I haven't done for years- nothing bad happened even though they could. Guess you just have to look at your results too- if you're getting great results you don't have to 'take extra risks' or even push yourself too hard if you don't want to. But if you're not getting the results you feel your deserve... you probably have to push your comfort zone more.
Here are two fairly unrisky things I'm going to do more of- risk probably isn't even the right word, but it's pushing myself to make more effort. I guess I'm risking my time. I'm going to start writing some share analysis on a new blog. I've been share investing seriously for over nine years now... but I'm not yet truly able to delve into all the financials of a company and analyse them. So I'm going to learn that... combine it with an INTERESTING writing style. I'll be doing this so I can fully understand my investments more, and hopefully eventually I'll be paid for some articles. If after a while I'm not paid I'll probably stop- which is a good incentive for me to write something worthwhile. I'm also going to be more mathematical about how much of my total wealth I have in each share I invest in, and what percentage of my wealth I have in certain sectors.
And I'm going to invest more time meeting high quality people 'in real life'. Know a lot of great people 'online' but will spend a certain amount of money meeting them face to face too.
So yeah... feel a bit better now. When you realise you have to do something and start acting you often get momentum.