One time at a place I worked our CEO brought together all of the software developers and gave us a presentation to help us better understand the other side of the business.
"Engineers," he said, "care about the truth. Engineers want to know their product is perfect; they want to know it's better than the competition's; that it's bug-free and feature-rich. Engineers are perfectionists - they're willing to put in extra hours to fix a bug that only they know about and that will never affect a customer, or to complete a feature that will never actually land us a sale.
"Salespeople," he continued, "don't give a damn about the truth. Don't get me wrong - they don't want to lie. Lying to customers is bad for business. It's just that facts aren't interesting. Stories sell. Value sells. Relationships sell. Salespeople want the story; the angle that will get our product in the door and get us a contract.
"Salespeople don't care about perfection. They're selling imperfect, buggy software, because all software is imperfect and buggy, and they've got no control over that. Most of their leads are dead-ends. Verbal agreements and offers fall through all the time. Salespeople are coin-operated. They want to know what the return on their investment of time and energy is. They'll work overtime - they work a ton of overtime - but only if they think there's something in it for them. And when a sale falls through, they don't take it personally - they get up the next morning and do it again."
I'm not telling you this story because I think you should think like a salesperson all the time. Not everyone is cut out for it - I'm certainly not! But there is certainly something to learn from the sales mindset, especially for us creative types who tend to be self-critical and constantly question our own success.
Dealing with Success
"What if I'm not any good?" we ask ourselves. "What if this is a fluke? What if people suddenly realize I suck? What if everything I've done suddenly gets exposed as some kind of massive fraud?" And then there's the constant obsessing over whether our work is good enough to release to the public. We polish and polish; we discard or bury stuff we shouldn't; we never get around to finally putting ourselves out there for fear we'll be rejected. These are natural feelings. They're natural because we care - we care about what we're doing and what other people think of us.
But try to go back to the sales mindset for a moment: what if your competitor's product is objectively better than yours? You still have to go out; sell what you have; tell the compelling story. Because even if you get a third, or a fourth, or a tenth of the sales that your competitor does, at the end of the day, the fact is you've made a sale and that's all that really counts. Maybe the customer hasn't heard of your competitor - lucky for you! Maybe the customer has been burned by the competitor, or likes you more, or the competitor's product doesn't fulfill all their needs. Regardless, they've chosen you. You fulfill a need for them. There's no point in wondering why; there's no time to sit and wonder why - just move on to the next sale.
You will never know exactly why people like your work and it doesn't matter anyway. What if you were a writer and found out that people read your stories because they're like Terry Pratchett's but not as good? That could be emotionally crushing - finding out that you're a cheap substitute for something awesome. But you know what? A lot of people are going to finish all of the Discworld novels and then ask, "Hey, is there something else out here that's like this?" And if some of them find your work, and a fraction of those people enjoy it enough to keep buying it, then you're going to make a lot of royalty money. It doesn't matter that you're not top dog at what you do.
Remember that Terry Pratchett wasn't top dog in his genre when he started writing - that would have been Douglas Adams. And both of those men got to where they did through decades of practice. You are not as good as you could be yet either, but the only way to get there is to keep putting yourself out there - to forget whatever setbacks you had today, get up tomorrow morning, dust yourself off, drink a bunch of coffee, and get right back to work.
Dealing with Failure
Engineers and creative types tend to internalize our failures and externalize our successes. We blame ourselves when things go badly and blame others when they go well. Did nobody reshare that story you posted to Tumblr? Yes, it's possible it was terrible. But it's also possible nobody saw it because you posted it right as CNN was starting coverage of our new war with Syria.
You don't need to be delusional and think that everything you do is perfect and that the only reason you're failing is because the world is out to get you. But you do need to at least identify both the internal and external factors and give them all reasonable weight. Sometimes things are out of your control. I worked on a very good video game that had to go up against fricking Halo in more or less the same market segment and genre. I can tell you a story about "external factors".
Look - you're gonna fail sometimes. Life is full of failure. I have a cousin who made millions with Microsoft and left to start his own business. Which promptly failed. So he started another one, which also failed. Then he started another one which burned down, fell over, sank into a swamp, and failed. But the fourth one, that stayed up, and now he's considered a successful entrepreneur. They say the definition of insanity is doing the same thing over and over and expecting different results; I say that if you're practicing your trade and improving then you're being persistent, not crazy. A little failure up front is expected; the only way to truly fail is to quit.
Be Persistent, Always Sell
You only get better by doing. You only get feedback by putting yourself out there. If you're serious about whatever it is you've decided to do, you just have to go do it. And sell it! Don't make excuses. Don't apologize for your work. Nothing turns people off more than answering "What do you do?" with "Oh, I make crappy things which you probably wouldn't like anyway I'm going to go hide now."
When someone asks me what I do, I tell them I develop engineering software - but I'm also a semi-professional musician who creates computer play aids for tabletop games and who produces an indie gaming podcast. I tell them where they can go to see all of my work. I may have doubts about the awesomeness of some of the things I do (thankfully not what I do for a living!) but I never say that to people. Instead, I sell it as hard as I can without being obnoxious and trust that they'll make up their own minds.
And you know what? People listen to the podcast. People pay money to come to our gigs. People use my software. I think I'm doing a pretty good job. Maybe I'm delusional, of course, but at the end of the day, if all of those things are true and I'm enjoying what I do, does it really matter?