If God wills, in exactly 4 months I leave for my attempt to climb the Riffelhorn in the Swiss Alps. The Riffelhorn has a number of routes you can take to the top. I'm told that the South peak has the best route options as well as the best views of the Breithorn (which I've already climbed) and the Gorner Glacier down below. The East side is said to be the easiest side to climb and is used by most beginners. The West ridge is said to be the most challenging climbing route. Whichever you route you take, you will be in Matterhorn-like terrain. Which route I take will be up to my guide based on my current fitness level. Pictures like this one will help him make that decision.
In the Alps, even the "easiest" routes have tremendous exposure, so you need to be prepared to be challenged. You absolutely MUST have solid fitness and endurance to do this. If you are overweight you will almost certainly fail. I would never attempt it without a professional mountain guide (fee: $800.00 per day). Climbing with a knowledgeable guide is like having a mentor by your side, offering not just safety but words of encouragement as you're climbing.
During our journey of life, overcoming a challenge offers a greater feeling of success than something easy enough to do every day. I've spent a lot of time talking to my family about this. I assured them I wouldn't take any unnecessary risks. Risk can be calculated. We realize that even great hardships in life can be acceptable. When you step out of your comfort zone you can develop great skills that can enrich your life. I tell students who are contemplating getting a doctorate to choose, not the easiest program, but the most difficult one. Much of the growth I've experienced as a teacher has come from the risks I took by choosing to go to Basel for my D.Theol. We had to live in a different culture. We had to become fluent in a foreign language. We had to get accustomed to a completely different educational system. We would be living far from home. Despite the fears, uncertainties, and so on, I look back on our stay in Basel as some of the very best years of my life. Taking that risk helped me to discover my strengths and weaknesses as a Greek teacher. I think even taking small risks can improve our judgment and life skills. Taking a risk just to be taking a risk is stupid. Personally, I don't want to live in regret and what-ifs. I'd rather live my life trying than never doing anything. Though no longer young, I'm still adventurous. But before taking a risk I always try to perform my due diligence.
In short, you don't want to look back over life thinking about all the things you should have done. Everyone will have regrets, but ideally you don't wish you'd done it all differently.