so I don’t know how much my advice is worth, but…

As I’ve gone along, I found that I just can’t keep as many projects in the air as when I was younger. The context-switching seems to cost more and I also seem to take more down time than before.

Now, that might not apply to you, but it brings up a question that will: Being honest with yourself, how many projects can you keep forward progress on at one time?

My first step once I’d answered that question was to identify which ones seemed really important to me at this time and “park” some of the others. I won’t claim to have got it down to the ideal number and the “parked ideas” list is always growing, but, I think a key element of just about every realistic “organisation scheme” is what I tend to call “triage.”

That is, there are hard choices to be made, CDE (can’t do everything) right now, so some things have to wait.

Creatively, that’s really hard, we have the ability to work in many media and the internet is always reminding us how much various media interact. But if you’re at the point where you’re asking the question of “what to quit” then for me there’s 3 sorts of filtering questions:

Am I doing this project for love or money? If it’s money, is it going to pay off with a defined effort? If it’s undefined, just how likely is it? Is that defined effort worth it for the money? Will this project be worth a lot less if I do it next year?

That can help you find some projects to park on the money side.

On the love side, I think you have to consider your artistic identity a little. Excellence requires some focus. If you currently have 4 kinds of projects going: Writing, singing, film making, photoshop (or still image skills) then it’s worth asking yourself, which of these things group together and which group do I tend to introduce myself at parties at?

From your short bio on the site, the feeling is that writing and singing have a big part to play for you, and they go together well, being grouped around words… Maybe it’s time to ask if you can “park” film-making or photoshop for a while?

After all, in the end, does “I write screenplays and my own songs, but I know photoshop too” really get you going more than “I write screenplays and my own songs.”

I’m also in the creative industry, so I understand perfectly. It is in my personal life where all these creativity-enhancing extras overflow the worst, as opposed to my work life which is practically a model of organizational structure and efficiency. There are just too many things I want to pursue, some of which could be really important someday.

So how to know? I think you can never really know what is important and worth the extra investment. Life, opportunities, trends are just too random. But this basic formula makes sense to me: How much (insofar as can be objectively ascertained, or else guesstimated) does this help me with my current projects and what I expect to be doing within the next 6-12 months? That question helps you answer the next one: Is it keeping me from doing other things that would have more value in the next 6-12 months? If the answer is yes, can it. If the answer is no, then feel free to pursue it as long as it’s not stressing you out or ruining your life. I think keeping in a happy flow has more to do with long term success than magical breakthroughs.

Of course there are also the hobbies and pursuits that do not bear fruit until after longer periods of time … maybe 5, 10, 15 years. If you are chasing any of those, you need to decide how much they are worth. It might be worth it. But don’t even think about taking on so many of those kinds of projects that finding fulfillment in all of them (and therefore any of them) will be impossible.

Seth has written a short little book all about this subject: http://sethgodin.typepad.com/the_dip/

It doesn’t sound to me as if your problem is knowing when to quit. It may be that your problem is knowing how to commit.

it seems to me the time to quit is when you no longer enjoy what your doing or it’s costing you too much in terms of your family and personal relationships/health.

if you love what you do and find it rewarding there’s no reason to quit.

Maybe not the best advice, but— Life as we know it now requires all hands [sic] ready to catch anything falling your way. Time was a job lasted. Careers seemed linear and possibly lucrative over the decades. Now, well, tomorrow if I’m lucky I could be on a picket line.

I tend to view the work and interests as tag clouds: Where does my energy want to go, but also how much money do I need now? Learning Photoshop tricks means nothing if I don’t need it Tuesday. Does the script focus me? Or do I want to write about the loose crocodiles in Vietnam? Or loose aliens on Broadway?

The actual workflow? It’s nothing but a river: A lot of detritus gets left on the bank. I might come back for it; I might not. But I didn’t “bank” it myself.

It’s a zen thing—

Worry less about what to leave behind, and just, forgive the expression, do it — by which I mean launch yourself into the next gd-awful thing you can’t get out of your soul.

You can’t do everything in life. Prioritize the fun things and the important things you really want to get done. Work your way down. If you focus on one too much you may get really sucked into it and not have time for others, but you may excel in it. And remember not to turn the fun things into a labor.

This is where Covey is quite good… Yes, the Seven Habits guy, I tend to think of him as the antithesis of the David.

He focuses on your identity as a set of roles in the world. That helps establish who you might think you are. When a set of projects is nagging/attracting/distracting you it’s helpful to know the part of you that they belong to as it were.

The War of Art by Steven Pressfield is very useful on cutting through the crap and as he calls it ‘turning pro’ about your work and whatever creative practice you are engaged in. I cant say I’d endorse the whole book but the initial two thirds or so are terrific.

I find having a healthy and uncritical someday/maybe list helps. For me it’s sometimes a borderline “probably never” list, but at least once a project is listed there it’s not constantly on my mind. It also gets me past the initial high of having come up with an idea and lets me examine it in the harsh light of day a week later.

On a deeper level, I’m slowly growing out of my tendency to pursue things that I’d like to like, but don’t necessarily actually like. Paul Graham talks about this a bit in his How to do what you love essay. Basically if I find myself halfway through something wondering how long it’ll be till it’s over, it’s a good sign that maybe it’s something I shouldn’t be doing.

Finally an oddball outlet I have is halfbakery.com. I have a lot of what seem like semi-decent ideas that I’ll never realistically have the time and/or resources to pursue. If I post them there, I can at least claim bragging rights when someone else gets rich off the idea.