I consider myself a cautious risk-taker. I've often said "I only gamble when I know I will win, but don't always look before jumping in." But I think challenging one's assumptions and concerns is a powerful tool in growth.
Quotes to remind you to jump sometimes
"Twenty years from now, you will be more disappointed by the things you didn't do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover." - Mark Twain
"The biggest risk is not taking any risk... In a world that is changing really quickly, the only strategy that is guaranteed to fail is not taking risks." - Mark Zuckerberg
"Do not be embarrassed by your failures, learn from them and start again." - Richard Branson
"Security is mostly a superstition. Life is either a daring adventure or nothing." - Helen Keller
"Only those who will risk going too far can possibly find out how far one can go." - T.S. Eliot
"If you are not willing to risk the usual, you will have to settle for the ordinary." - Jim Rohn
"Life is inherently risky. There is only one big risk you should avoid at all costs, and that is the risk of doing nothing." - Denis Waitley
"Take risks: if you win, you will be happy; if you lose, you will be wise." - Unknown