Some things I wish I’d realized earlier:

1. Just send one message, it’ll get easier after that. Yeah, it’s stressful to do but honestly, a lot of the time the anticipation is worse than the action itself. Once you send a single message, you’ll probably find that it gets a lot easier to reach out to people, even if you’re worried your message will feel kind of out of the blue. Same goes for approaching people in person! Once you do it once, you’ll be able to do it again.
2. You can always set meetings up during the trip! Even if you get to Monday and don’t have anything set up, it’s definitely not too late to find a time to meet up with somebody for coffee as long as you’re up front about your time constraints. If you click with somebody you meet at an agency or find a name after you leave, reach out anyway. Even if you can’t make something work, you’ve still opened a line of communication!
3. Send follow-up emails or LinkedIn connection messages when you get back to the hotel that night. Don’t wait for the end of the trip or later in the week. Sending a message when the interaction is fresh in your mind is the best way to make sure it gets done and that you actually have something to say when you reach out.

Jordan Blackburn | 5.2.19