If you're super cool and hip like me you'll know that the term "Shoot your Shot" is a popular term used by super cool and hip young people (also me?) to explain taking a chance with a romantic interest. If you like someone and don't want to wait for them to make the first move, you'll shoot your shot and tell them you have feelings for them. Generally, the move is thought of as bold or courageous and even if it ends with the wrong outcome, its seen as admirable.
Despite originally being a call to action to ramp up your confidence in pursuing romantic relationships, it can be an empowering concept in the realm of business as well. And as a married thirty-something, I'm definitely not cool enough (despite the assertion of my hip-ness just one paragraph ago) to use it in any other way. So let's take this concept and apply it to something I actually know about, ok?
Shooting Your Shot as an Entrepreneur:
When you're in business for yourself your motivation to succeed (or simply your motivation to pay your light bill) wills you to make connections, land deals, and work with like-minded people. Often times, these relationships and opportunities will develop organically. But sometimes, you'll need to move them along a little bit to really get what you want. Is there a client you've been dying to work for? An industry leader you want to collaborate with? A pipe dream you just can't shake and a person that can help you make it happen?
Instead of pining from afar, why not just go for it?
Before you get all inspired and start to fire off emails to everyone under the sun, you need to put some thought into your approach. Shooting your shot as an entrepreneur takes finesse, confidence, and a little luck. Get comfortable with this skill and you'll be well on your way to creating some awesome opportunities for yourself.
What are your intentions?
Just as if you were contacting a romantic interest, determine exactly what you're asking for. Do you just want to reach out and thank someone for their work? Are you asking for mentorship? Collaboration? A meeting? Do you want this person to hire you? Make sure you're clear about your intentions from the beginning so things don't get weird as you progress.
Sell yourself but be humble
Yes, you should tell this person how great you are but just as if you were on a first date don't overdo it. Master the art of the humble brag. Let them know why you're awesome and why they would want to work with you but keep it short and sweet. Props if you can sneak in a few compliments, too.
The other day I sent a 'shoot your shot email' to someone in an industry that I've been dreaming about participating in for a while now. Does this person need to know that I had a "holy crap I'm the worst entrepreneur ever" freak out 10 minutes before I crafted this email? Absolutely not. (Side query: Aforementioned freak out is super normal, right?) The same way that you don't talk about your 5 cats or your crippling fear of beanie babies ad nauseam on a first date, keep all of those business-related insecurities tucked away for the time being.
At the end of the day, why not?
If you really think about it, as long as you're respectful and professional, is there any reason to NOT try? Maybe that person that you're dying to work with could use an extra hand. Maybe that industry expert would love someone to mentor. Maybe your big break is just one ballsy email away. Or, maybe it's not- but there's only one way to find out.