We tend to be quite mediocre when it comes to judging ourselves, assessing our situations, even remembering our own lives.  So it’s helpful to reach out to friends, family, mentors, or co-workers for advice. This advice could be about anything, but it can be particularly valuable when you’re at a crossroads in your career. The people you ask should be ones you trust and are comfortable with. This may not be the best time to ask your wacky aunt for advice. You also want to make sure that whoever you ask is willing, and ideally enthusiastic, about this favor. That shouldn't be too hard as most people like giving their opinion. It can also be helpful, if you’re comfortable with it, to reach out to past friends, bosses, teachers, and other people in your life you haven’t spoken to in a while. Those outside your immediate circle can sometimes have the most interesting observations about you.


The people who know you the best might, at least on the surface, possess the best well of advice. This isn’t always the case though. It depends on what you're asking about. If you want career advice, your friends & family may not know that much about that part of your life. In this case, make sure to give whoever you’re asking as much context as possible. Although, you could do an experiment. Ask them for advice about your desired topic without giving them context and see what they say. Then give them context and see how, if at all, their advice changes.  

This is actually one of the best reasons to ask friends & family for career advice. They can give you an outside perspective. When asking them questions, it can be helpful to prepare a little bit before hand. You don't want the conversation to go off the rails, and you want to make sure to cover every topic you had in mind. Also, before going to anyone for advice, it’s important that you’ve thought things through yourself. This is probably a no-brainer as most people do that first anyway, but it’s important to note. Whatever questions you've asked yourself, those are the questions you should be asking others.


While family and friends can give you an outsider's perspective in terms of your career, they can sometimes be too close in other ways. They have known you a long time, to the point where the advice they give is exactly what you had been thinking. Sometimes this assurance can be good, but sometimes you need a perspective that's less informed about you. Reaching out to your colleagues and mentors can provide that perspective. They will also be far more informed as to your specific career situation. Rather than basing their advice on their knowledge of you, they base it on your specific career situation. Perhaps they’ve been in the exact same career crossroads that you’re currently in and can share some super specific insight.

The biggest difference between asking colleagues and asking family or friends is that the latter is likely willing to help you out whenever. Your colleagues may not be quite as available. There’s little doubt that they’ll help you, but they’re busy people and you can’t just call them up whenever. Set up a chat or a meeting that works for them, and make sure to come with prepared questions, and be clear about what it is you're looking for.


Sometimes we really need a perspective we can’t imagine. We’ve heard the same thing too many times and we just need one voice that breaks the mold. Perhaps the career path you’re thinking about following is too radical or unexpected for your friends and colleagues (like becoming a freelancer). A person in neither of those groups can sometimes understand where you’re coming from more than those close to you. Someone who has little knowledge of you, with no stake in the game, can often give the truest advice. You probably don’t want to talk to a complete stranger, but an acquaintance or old colleague can work just as well. Set up a time that works for them, and have a list of questions ready. As you don’t really know these people, this advice session will probably feel more like an interview than a conversation. You might be surprised by how revealing it can be.

Advice is important, we should ask for it often, but it’s important to know how to best decipher it. Be careful not to get your own decisions confused with the decisions of the people around you. We all impart our own values, desires, and opinion onto each other, and it can make it difficult sometimes to figure what it is we really want. When asking for advice going forward, it’s essential to know who to go to, what to ask, and when to go with your gut.