You know the feeling well: you've decided to attend a networking Meetup, you get to the location and only see one other car in the parking lot. You go into the building and your stomach sinks as you enter the appointed room. There's only one other person there, and it looks like the organizer. You quickly check your phone: it's 20 minutes past the starting time. How embarrassing. You're the only schmuck who turned up. There are unopened drinks on the table next to uneaten food. You look desperately around: this poor organizer looks ready to talk to anyone and you see the next 2 hours of your life vaporizing in a mist of uncomfortable conversation as you try to politely leave.
You're Doing it Wrong
Most people I know would be uncomfortable with the situation I described above. In fact, I would have been uncomfortable with it until very recently, when I realized how much it was holding me back. I don't like being witness to, much less a part of a failing enterprise as much as the next person, but if you are going to start something new, you better get used to that feeling and stop letting it affect you.
Almost every new venture starts with discomfort. It's easy to forget that when you are starting a company because coding a site allows people to hide from that sort of discomfort for far too long. I would wager that if every web startup required the founders to knock on a 1,000 doors and pitch their product to the resident inside before being allowed to write code, very few businesses would get started, but those that did would be 1,000 times better off.
I'm talking about being willing to physically put yourself in socially uncomfortable situations to push your vision forward. I'm talking about hard sales, cold calls, meet and greets, and asking people for favors. I'm talking about being willing to politely ignore the unwritten rules of social decorum and get down to business. I think the more you are able to do that in your life, the more successful you will be at achieving your goals.
How to Do it Right
It's all well and good to talk about being brassy and hustling for your vision, but how do you go from being a shy, socially-hypersensitive person (like I used to be) to a self-determined success? Here are two tricks that I use:
1) Prediction Boxing
When you are faced with something uncomfortable, you will find yourself making excuses to avoid it. What you are doing is trying to avoid encountering the worst case scenario. Let's say you are going to cold call a potential customer. You have been putting it off for a week, but why?
There's a quick mental exercise I do which helps me put possible outcomes into perspective. It works like this: think about what you are going to do, and generate a scenario in which everything turns out impossibly well, and I mean push this to the extreme. To use the cold calling example, the extreme positive situation is that your customer not only buys what you are selling, but they 100 copies of it and refers 100 of their corporate friends. Bam, your company is now a success.
Now, think about the absolute worst case, and I mean the most god-awful worst way this could turn out. This time, your customer screams curses at you for the unsolicited sales call, tells all their corporate friends you're an idiot, and adds you number to their block list. Okay, that would suck pretty hard.
Finally, think about a situation in the middle. Maybe you get a curt hangup, or a polite denial. Maybe they tentatively agree to try your software for free with no obligation, maybe they try to get you off the phone by making up an excuse not to talk with you.
I have found time and time again that the middle situation is the most likely, and so long as it doesn't contain any truly horrible results, you should probably do what you are contemplating. Remember: think of the best, then the worst, then the middle situation, and if the middle doesn't seem bad, go for it.
This is a motivational hack that one of my good friends shared with me, and has proven effective time and time again: tell people what you are going to do, and tell them when you are going to do it. You will get the most out of this if you tell people you respect, and since we are talking about intimidating challenges in a business context, I would recommend your co-founders. Here's how I was able to push myself out of my comfort zone repeatedly to get stuff done:
Whenever my co-founders and I would come up with a marketing or sales suggestion that was uncomfortable, I would volunteer to do it regardless of my comfort level with the task and set a concrete deadline. This part is easy: it makes you appear valuable and important to your cofounders, and that feels good. The hard part comes later and you can build up the courage when that time comes. The most important thing is that you tell them exactly what you are going to do "I will cold-call 5 of our potential customers" and give it a deadline "and I will call them by this coming Monday."
By making a formal, concrete, public commitment, you have raised the stakes of failure, and made it that much harder to back out. Now if you fail, you can't hide: the people you respect most will know. You've put yourself in the position of having to succeed. Make no mistake, you don't end up hustling accidentally. I recently saw a talk by a guy talking about customer development in which he said that he would never have done it if the alternative hadn't been firing his best friends. One cold call may not push you to that extreme, but it's a good indicator of how difficult it is to make a habit of hustling.
If you're interested in learning more about the tips and tricks I use, you should read my cofounder's book: The Motivation Hacker.
Starting something new is scary because failure is scary. You maximize your chances of success by improving your hustle and overcoming that fear. To use the example at the beginning of this post, there is no reason to be scared of an empty room. Worst case scenario: you lose a bit of time, learn what doesn't work, pack up early and try again.