How To Hit Up Your Heroes For Career Advice

When you’re looking for career advice, who better to approach than the people you admire? After all, they’ve accomplished what you’d like to.

But the idea of contacting people who seem a lot more important and successful than you can feel intimidating, awkward and contrived. Well, we believe that in stepping outside your comfort zone, great things can happen. Because really, what’s the worst that’s going to happen? The person says ‘no’? Here are some pointers on how to approach your heroes and get the best outcomes possible.

#1 Keep It Real

Be genuine about why you’re approaching someone and let it inform everything you do in seeking their advice. Madeleine Dore is the founder and editor of Extraordinary Routines, a project that interviews creatives about their habits and experiences in daily life. “Asking someone to tell you about how they spend their day and their inner-ponderings and struggles can feel quite intrusive on the surface, but maintaining genuine curiosity has been the key to drawing out the best in my subjects,” she explains.

Remember that your heroes are humans too. Complimenting them before asking for their advice is a nice way to get the conversation started, but being overly gushy is only going to sound fake and make them feel uncomfortable.

If it’s only one specific question you need to ask, so be it, but surrounding yourself with people and projects that interest you could be more fulfilling in the long term. Artist Honor Eastly started the podcast Starving Artist as a way of asking creatives about their financial situations, and recommends becoming actively involved in the work of people you admire in an authentic way over time. “Maybe they’re doing a workshop? Or a talk? Or working on a project you could contribute to?”

#2 Do Your Research

Understanding the career trajectory of your hero can be as simple as a quick Google search or a glance through their LinkedIn profile. It might feel a bit stalkery, but it would be rude to not know some background information before contacting them. Plus, as Alex, a 28-year-old doctor explains, “It isn’t like they aren’t aware that their research or department profile is out there.”

While it would be nice to ask Barack Obama how he spends his day, or to see what Lady Gaga’s preferred concert venues are, be realistic about who you approach. As Collette, a junior lawyer explains, “the person you admire may be too high up in an organisation and someone closer to your current level may provide better advice.” Consider the conventions of the industry within which you’re operating. A psychologist, for example, may prefer to be approached through a professional organisation, or a book author may find it easier to manage enquiries through a publicist.

#3 Be Respectful

Approaching your heroes can feel nerve-wracking, but don’t let that get in the way of being clear and succinct – they’ll appreciate you being respectful of their time. Express interest in their work, be specific about what you seek and the process that’s involved in getting it. Being flexible on the arrangement also helps.

“Don’t use the phrase ‘pick your brain,’” says Madeleine. “It’s such a one-sided request and conjures up an image that the other person will be left picked-over, drained and brainless!” Consider instead how this interaction can be mutually beneficial. Can you offer the person coffee or lunch, publicity, or the opportunity to engage in a project that interests them? Likewise, reflect on how you’re asking the question. As Honor explains, “asking ‘what audio gear do you use?’ is very different to ‘have you thought about including what audio gear you use in a FAQ on your website? I’d like to know more about it and I’m sure many others would.’”

Because of her fairly structured and successful medicine career, Alex is often approached by young doctors for advice. For her, basic manners go a long way. “I get demanding patients and families all day long. The least you can do is ask me how I’m going,” she explains.

It’s important to remember that even if your hero is willing to participate, this doesn’t mean you can email them on a weekly basis or have them as referee on your CV instantly. Be mindful of the arrangement you have both agreed to, and let it evolve naturally, if at all.

#4 Be Open To Rejection

If you receive an outright ‘no’ or never hear back from your hero after following up, try not to be disheartened. If you’ve been genuine and respectful in the way that you’ve approached them, you’ve done all you can. “It’s important to remember it’s not personal,” explains Madeleine.

Honor agrees: “For me it’s reached a point where I absolutely cannot reply to all the emails I receive, let alone meet everyone’s requests. If I did I would never get any of the stuff done that people are emailing me about!”

There are other options if your hero can’t provide what you need when you need it. They may be willing to help you out at a later date when they’re less busy, or direct you to someone else who is available. Formalised mentorship programs or member organisations may also provide assistance.

It’s also worth considering people within your existing networks who could facilitate an introduction or surprise you with their own wisdom. And hey, you might even realise that the real version of your hero doesn’t match your imagined one, and look elsewhere for advice.

Once you’ve committed to approaching your hero, go for it – as obvious as it may sound, it’s the only way to get it. Who knows, one day you’ll be the hero being asked for advice and realise how great it is when people do it properly.

Chelsea McIver is a freelance writer and editor based in Melbourne. Her work appears in titles including VICE, Junkee, Broadsheet and The Big Issue. Tweet her @ChelseaMcIver