If you need help, ask. If you want to meet someone, introduce yourself.
This year has been full of asks and introductions for me, two things I'm not naturally inclined to do. It has been an amazing experience.
I've had wonderful conversations with interesting people and, as these things tend to go, those interesting people have introduced me to others. A few people that I greatly admire are helping me make something I've always wanted to make. I'm writing here because of an ask and an introduction.
The answer hasn't always been yes; far from it. Every person has been kind and generous, though, and I have learned something each time. And a conversation now makes a yes a little more likely in the future.
It's an uncomfortable experience to ask a favor or reach out to someone you don't know well. Here are three things that make it easier.
First, get to know the person long before the ask. Follow them on Twitter, read their blog, comment or reply now and then. In other words, engage with them and what they're sharing with the world. Reference some of those things when you contact them. Show you've been paying attention.
Second, be very patient. I've received incredibly kind and generous replies weeks after I sent an email. People are busy and most likely your email falls outside their typical queue. One of the kindest responses I've ever received said, "I wanted to give this the attention it deserved." It made my day.
Don't assume anything and in most cases, don't follow-up. Once you put something out there, it's no longer in your hands. Let it go and trust the result.
Third, and most importantly, remember that the favor is the listening, not the outcome. If someone takes the time to listen to what you have to say, consider it thoughtfully, and respond, you have received a real gift, regardless of the result. Thank them, offer to return the favor, buy them coffee or a drink if you have the chance, and wish them the best.
Stop hesitating. Say what you want to say, ask for help, introduce yourself.
Then hit send.