Pledges, persistence, and the performing arts

Recently, I met with my former boss in arts fundraising, and he said that he believed every artist should work in fundraising sometime in their lives--the lessons you learn there teach you a lot about the resilience and perseverance you need to pursue a career in the arts. In my experience working in fundraising, I absolutely agree with him, and here are a few of the things I've learned that I'd like to pass on:

Rough periods come with the territory
One of my current bosses said to me that sometimes, even the most experienced agents (people who close over $1,000 in one phone call) can go for as long as three weeks without closing so much as a $5 token gift in that period. 
This is not for lack of fine tuning how you pitch, or how you work on your craft and branding as a singer. This is to say that even when those things are finely tuned, you'll still go through rough periods. There are many things that are in your control, such as what you offer in your audition package, or how you tailor your fundraising pitch. At the same time, there are still many factors that aren't in your control, such as the stock market--in the case of fundraising--, or whether you happen to be what the panelists are looking for--in the case of singing.
When you know periods like these come with the territory, you're able to be much more resilient, and far less likely to beat yourself up. I've been through those sale-less periods, and I know how disheartening they can be. I'd be told by my bosses and managers that nothing was wrong, and to just keep pitching until I finally close. The same has been true for singing. And all of that said...

Tides change
When you know your pitch, or audition, is strong, and you continue to fine tune them, then it's just a matter of time before the tides change. I've personally experienced this, in both these areas of my life. 
In fundraising, there was a period in which I went a full week without a single sale--then, I closed $3,600 in one phone call, and then $2,000 a couple of days after that. There wasn't much rhyme or reason as to what I did differently--I offered more or less the same pitch as I had done the entire week before. Other external factors had changed, and that's all that happened--those external factors weren't in my control, and I had to persist in pitching until those fell into place. 
Similarly, there was a period about a couple of years ago which looked quite bleak--I was about to produce one of my concerts, but I couldn't see far past that. Four days after I performed that concert, I got a phone call asking if I'd like to have that performance broadcast on national radio. That experience was my singing equivalent of going a full week without closing a single sale, and then closing $3,600, and then $2,000 in only two phone calls. 
That big "yes" could be right around the corner, but you can't necessarily see it yet. 

Celebrate every success along the way
Of course we all strive to close those big individual sales, or to get those big gigs (radio broadcast or otherwise). If you don't celebrate every success along the way, though--small and big--, you're all but guaranteed to burn out. In fundraising, every token gift matters. Celebrating even the most seemingly minor of token gifts is important as a validation of your ability to close sales--also, that token gift helped open the door to hundreds of thousands of dollars of corporate grants, which are awarded to arts organizations on the basis of participation; besides, as one of my managers said, "That's five dollars the [arts organization] didn't have before!"* 
In singing, there is typically a prescreening round for an audition, and the live audition round which follows. Auditions are incredibly selective, and not everyone gets to the live audition round--there are far more talented singers than there are slots available for that round of auditions. The competition to get from that live round to being accepted for a job is even more selective. Even getting to the live audition round, or the next round of a competition, is an achievement, regardless of the outcome--it is a validation that you were strong enough to stand out among many other singers to make it to that next level. While singers continue to strive for the highest possible results, making the next audition round is absolutely a success, and one shouldn't lose sight of that. (Also, even if you don't get that particular audition, you will have sung for people who could possibly hire you in the future. That's another reason getting to that next round is something to be proud of!)

Of course, all of the above is on the condition that you're fine tuning what you do, and that you have people around you who will help you get better and also encourage you along the way. 
If you are, though, and you're still passionate about what you're doing, then keep persevering. Your own personal $3,600 sale, or radio broadcast, could be right around the corner, even if you can't see it yet.

*(On a separate-but-related note, if every person called gave even only $5 each, that arts organization would raise an enormous amount of money in no time!)