Investing the money...
My husband would be the first to tell you I can be a bit conservative with my money (I have Scottish ancestry). To me, that means I want to make sure I'm spending my money on something I really desire, and I want to make sure that I'm getting what I expected. When it comes to writing conferences, contests, and other writing expenses, that can be a murky pool. It's important to do your research. There are a lot of conferences out there - pick one that focuses on your chosen genre. Find a contest that seems reasonable (if you're writing for the first time ever, you may not be ready for a contest based on New York Times best sellers). Same with editors - find out what they specialize in. And remember, you get what you pay for.
Investing the time...
We all spend a lot of time writing (although sometimes not as much as we should or want). Trying to squeeze out any extra time out of the rest of our lives can be harrowing. But you need to invest in any endeavor. So spend the time to do the research on your editor. Spend the time to prepare for your conference by putting together business cards and making a game plan for programs and networking opportunities. Spend the time to review your contest entry and make sure it's the best it can possibly be. Otherwise, you're wasting your time, and the time of the writer/editor/agent on the other end as well.
Your story has a lot of you in it. You've spent hours, days, weeks, months with these characters. You love them and you hate them and you can't live without them. Now you have to send them away to be read by someone else? By someone who will - gasp - judge them? Yes. We write for ourselves. But we also write for others. And others will judge us. And we will get good and bad feedback. So be ready for the heart-racing when you walk up to an agent at your next conference, be ready for the frustration when you get your manuscript back from an editor and it's covered in notes, be ready for the thrill of being a contest finalist - it can happen!
What I'm trying to convey is that, even though writing is a very solitary activity, you also have to take part in the community, get out there and share your work, get the feedback and chug it around so your next piece is that much greater. It's worth it.
Some of my favorite conferences and contests:
Check out Writers Digest, they always have some kind of contest going on. And they offer an annual East Coast and West Coast conference. (I'm dying to get to New York this summer!)
For children's and YA writers, Society of Children's Books Writers and Illustrators offers an annual conference, plus regional events. And, you can find out about a bunch of contests that way, too. Not a children's writer? There's a group for pretty much every genre out there - just Google them and you'll be amazed.
Sign up for email notices. Most writing magazines offer these. It seems like they could fill your in box, but I love discovering a gem of a contest (while simply deleting the rest). Like the Dear Lucky Agent free middle grade contest just announced.
Shaw's guides: No matter where you are, you'll find something of interest for you. But beware, some of this information can be out of date so always check the organization's website directly.