How does one discover new ways to spend money? In essence, if you had $25k each year to spend on new hobbies, or activities, or items, what would you spend it on?

Save it till you can do the one thing you've always wanted to do without fear of running out of money while doing it. If you must spend: 1. Dont Buy stuff, buy experiences - kiteboarding, jumping out of planes. Do it with the people you love. 2. Spend it on travel like working for habitat for humanity or going to truly beautiful places like trekking in the Himalayas. 3. Use it to meet and spend time with all sorts of people with different experiences. This will educate you like nothing else will. A different point of view is worth 40 IQ points as they say. 4. Buy a comfortable bed. 5. Save as much as you can. Life happens fast. Have fun!

I'd go hike the Camino de Santiago. Or the Appalachian Trail again. Or go tramping in New Zealand again. Or I'd take up hang-gliding. 

After reading "59 seconds" I have some scientific proof to say: If you want to be happier, expend on experience not goods.

25K may not be as as much as you think it is, barely enough to buy a good sofa in some stores, for example. But to answer your question: First, budget your charity dollars the same way you budget your household expenses. Give enough so that it hurts a little. Second, save it save it save it! In five years 25K becomes 50K and then 50K becomes 100K, and so on and so on and so on. Never underestimate the power of compound interest. Third, set your priorities. My priority is to have a serene, beautiful place to come home to every day; so rather than travel or eat at expensive restaurants, I am constantly improving my space. (I also like cars.) Your priority, I suspect, is to socialize and be out and about with friends. If so, there's your answer.

First off, big income is a fluke not a lifestyle.  It won't last.   So I DONT recommend looking for ways to spend it.  Invest/save it and only spend what you really, really want to. Now having said that... go shopping.  Women know how to do this so you nmght want to take one with you.  Just walk around the mall and look at whatever strikes your fancy.  Make yourself a list of anything that looks interesting.  Then, go find a magazine about your new potential hobby.  be it pistols, motorcycles, or macrame there are magazines for hobbiests.  Read a bit about it and learn whats involved and how to get started. If it still interests you, go ahead and start!

There are a million things you can do! 1. Go skydiving 2. Learn Scuba diving 3. Rent a hot air balloon and keep going 4. Travel to unknown places 5. Learn to fly, get a pilots license 6. Build a robot (technology, its an awesome feeling when your robo works) 7. Buy awesome and rare wine 8. Paragliding 9. Mountaineering 10. Invest in your physique, join a gym get a six pack maybe (If you dont already have it) 11. Photography, buy a SLR/DSLR The list goes on!

Money can not buy you happiness, but the lack of it will buy misery. Don't look so hard for ways to spend your money. You say that you are saving some. Save more and buy some long term security.  Now is the time to look at disability insurance and long term care insurance. What if you were suddenly unable to work or produce an income due to injury or illness? What if you discover next week that you have an aggressive form of cancer and will require travel for special treatment or evaluation which could take extensive surgery and rehabilitation over a year or more? What if you sustain a life altering injury like a spinal trauma or severe burn? Are you prepared? Your first obligation is to protect your income and then any accumulated wealth. One thing you can buy with your additional income is long term financial security. After that, follow your whims. Know that experiences bring more satisfaction than things. Giving to others brings more satisfaction than personal indulgence. Start small. Buy a friend lunch. Take in a film together. Share a trip with someone who would never afford it. Find a passion and support it. Be a friend who shows concern and support. Make yourself into the example that you would want to follow.

Whenever I have had extra cash - and I am quite a satisfied soul too so I understand the difficulty in deciding what to do with it - I have given it away. My interest, for various reasons, is in helping young girls from poor families realise their potential, and in women's rights to dignity and self-reliance. The former is what I always end up giving my money to. Helping individual girls through charities I have checked up in advance. I never miss the money and their lives are immensely better for every little bit I can do to help. You are in a great position to help those less fortunate. For my money - literally - I'd help someone in need whose need I can empathise with.

Given that you are already paying down your mortgage, are adequately prepared in case of a personal financial downturn, have therapy already if it's useful to you, and good medical insurance, here are my suggestions: 1. Help seed a great new nonprofit. $5,000 can be pivotal to a promising new NGO (and help it raise more money), but means little to an organization with a $5 million budget. After you make the contribution, stay involved with the group--ask them to call you every few months to update you and chat. 2. Find ways to invest in your personal life if this is not your usual bent: A personal trainer, clothes, fencing lessons, etc. Polish yourself up physically. Meet people if you want to be meeting people. 3. Learn to cook something cool. Have a dinner party of new or old friends where you cook this. 4. Take your parents on a trip. Good luck!