Start by figuring out who you might want to talk to––this can be more challenging that you might think! There’s no right path here, but the best way to set yourself up for success is to start from a place of openness and curiosity:
Are there particular fields within politics (e.g. digital, comms, organizing, data, etc.) that seem especially exciting to you? Types of organizations that you’d want to work at? Roles that you might one day want to have? What questions do you have about your next career steps? Which ones feel the most important or exciting? Hypothetically, who might you want to shadow for a day? Is there someone at a certain organization or holding a certain role who you’d have lots of questions for? Are there particular jobs that you just want to know more about? From there, you’ll want to build a list of folks to reach out to. Not everyone needs to be super senior, but I usually recommend chatting with folks who are at least a few years into their career. I’d try to prioritize people who:
Are connected and networked: It seems like they have solid roots in progressive politics, probably know a lot of people, and really get the landscape. (This is both helpful in enabling them to make connections for you down the road, and in making sure that they can offer advice about career paths that go beyond their particular role at their particular organization. Seem to be doing cool stuff: Make sure that you’re connecting with folks whose jobs seem at least potentially interesting and impactful. You don’t need to be an expert on their story before you reach out, but you should know enough that you’d be prepared to ask thoughtful, informed questions. Make you curious: When you look at their bio or LinkedIn profile, do you want to know more? Do you have at least a few questions that you’d want to ask them? If the meeting led no where (they totally ghosted you afterwards, didn’t help you get a job at their org, and didn’t make any introductions for you), do you think it’s possible that you’d have learned enough in 30 mins that it’d still have been worth your time? From there, there are a few sets of people you could think about connecting with:
Core relationships. These are folks who already know you and want you to succeed. That could include your current boss, someone at Progressive Pipeline, or others in your network who could offer valuable advice. We often underestimate how useful these folks can be, and tend not to engage them enough. Consider reaching out for an informal catch-up, ideally grounded in a core question you’re trying to answer (often “what do I do after college?”) Extended network. You've met once or twice, or know lots of folks in common, but they aren't quite in your corner yet. Maybe you were in a group meeting once, or they reviewed a project you worked on. You can use broadly similar tactics to the ones in the Cold Outreach section, but with a more personal touch––they’ll be much more likely to respond than total strangers. A note that says something like this can go a long way: “We met during that meeting with Sarah and Paula a few weeks ago, and I saw that you’d managed a bunch of House campaigns. I’m trying to think about my next careers steps, and whether I might want to go work on a campaign––would you be open to finding 20 mins to hop on a call and walk me through the landscape?” Shared interests. You have something in common (maybe a school, or workplace, or identity), but you don't them yet. Your approach can be very similar to completely cold outreach, but a warm note that mentions the connection can add a lot. Everyone else. This is a little more intimidating, but it has a surprisingly high success rate. If you write a thoughtful, personalized, curious email (see below), people will often be flattered and respond. If you’re looking to build a list of folks to reach out to, I’d recommend either doing some LinkedIn searching, or just making a list of organizations that you think are cool, and then going to their “Our Team” pages and reaching out to 1-2 people at each orgs who seem to be doing meaningful work that’s related to your areas of interest. This often works! 
Building A List