How to Ask Someone for Career Advice Without Being Annoying

“It can’t hurt to ask” is extremely common advice, but when we’re all so accessible online, just being able to reach someone and ask for their help doesn’t mean what it used to.
Viktor Solomin via Stocksy

Networking is excruciatingly important. It’s how I’ve gotten every writing job I’ve ever had, including writing copy for an insurance company and trivia for a TV show’s app. But I am tremendously bad at formal networking: Asking someone out to coffee to pick their brain for career advice and establishing a professional working relationship. If you’re new to a field or dreaming of a career but unsure how to get it, odds are you’ve come across the phrase: “there’s no harm in asking” when it comes to seeking advice. Fire off that email, slide into that DM, ask that person to help you climb the ladder and seize your glory! This, my beautiful new best friend, is based on acutely outdated thinking.


Recognize that times have changed

In the industrial U.S. (around the 1940s to 1950s), a narrative bloomed about how to get a job thanks in part to an abundance of white-collar work and a lack of resources to more efficiently recruit for those jobs. There was no LinkedIn or Indeed, no hundreds of applicants for every one job posting, no “We’re hiring!” tweets passing through your timeline. Through this, gumption became the mythical key to unlocking a career. The narrative goes something like this: Your grandfather (or a similar white, male octogenarian) regales you with a story of how he got his first job: “I was 4, fresh out of a fancy college that cost a nickel to attend, and I walked into the first building I saw and shouted “I WANT TO WORK HERE.” The boss overheard, and that’s how I became CEO of BLORGCORP, the world’s number one proprietor of BLORG! So there’s no reason why you can’t get a job! Just show ‘em you want it! Now, eat your BLORG before it gets cold.”

Me: "The academic job market is highly competitive."

My grandma: "Have you tried reaching out to your top schools and telling them you really want to work there? I think if they knew you were interested, it would make a big difference."

— Laura Jákli (@laurajakli) September 9, 2019

The times have changed and, aside from nepotism and in-hiring, a majority of companies have automated boundaries set up before the interview process even starts. Yet the gumption narrative still persists among prospective employees like myself. As it turns out, we’re doing it all wrong.


Don’t just DM your heroes

As technology and social media have grown to become essential in our daily lives, it’s easier than ever to reach out to people you want to work for. I once DMed a screenshot of my whole resume to Nick Kroll on instagram, with zero consideration that he probably has hundreds of unread resumes in his message requests from fellow “no harm in asking!”-ers.

The result of this accessibility? Successful people in network-heavy fields learn to create their own tools to cut through requests to “pick your brain.”

Aminatou Sow is a writer and host who hates having her brain picked, especially outside of email. “I personally think there are too many inboxes to access people now,” says Sow. “I get work requests via Twitter or Instagram DM and that's bananas. Email is for work!” When I reached out to Sow for this piece, I had to censor my email to avoid getting caught in any junk filters that would assume I was one of many asking to pick her brain. I was just one of one, asking to pick her brain about “pick your brain.” It’s meta!

Adam Conover is the host, creator, writer, and showrunner of Adam Ruins Everything on TruTV. He is busy on top of busy. Despite this, he still dedicates himself to helping as many people as he can, whether that’s specific career advice or job recommendations or a pep talk. “Being where I am in my career, I'm committed to mentoring people and helping people out and giving people a hand up.” His focus is limited to comedy, with the intention of increasing the diversity of his field. “But,” he notes, “I have a limited number of people I can do that for because my time is limited.”


To save time, Conover has worked to cultivate an answer to the broadest array of advice anyone could ask of him, sprinkled across interviews and profiles, with the broadest details on his easily accessible Wikipedia page. When we spoke, it boiled down to: perform and create however you can, pay attention to other comics, and make friends…for 14 years. Despite this, he still receives general “pick your brain”-type requests across his social media platforms all the time. He’s had to create a personal heuristic centered on non-marginalized people he doesn’t know who use “pick your brain” to cut through the masses so he can help marginalized voices: “Is it possible that I've accidentally disqualified some deserving people? Perhaps. But again, I get a lot of requests like this and I need to sort them somehow.”

Lisa Hanawalt is the creator of Netflix’s Tuca & Bertie and the production designer behind Bojack Horseman. She enjoys helping young artists through pep talks and friendly nudges, when she can. She knows that “it's lonely being an artist. Most of the time you're working, no one's there to tell you 'Yes, you're doing the right thing. Yes, continue this stupid project that for some reason you're obsessed with.'

“I sometimes feel like oh, I'm actually able to lay out some bread crumbs for artists who are younger than me and they can at least see some sort of path to things that they want,” says Hanawalt. “Or see some kind of way of someone advocating for themselves and taking care of themselves and not doing too much work for too little pay. And I can provide some comfort there or some guidance, even if I can't provide an easy answer. Sometimes people just need someone else to be like 'Hey, you're doing okay. You're on the right path.' And I think, yeah, I can help with that.”


Generalized questions eat up space Hanawalt could be using to nudge along young artists. “We're all humans and we're all flawed and we're all busy,” she tells me. It takes two seconds to find this talk she gave detailing how she became the production designer on Bojack Horseman, yet she receives simplistic messages from people asking “How do I become an illustrator?” with “zero evidence” of the messengers “having made art, ever.”

“Well,” says Hanawalt, “If you're not even going to start with anything, and you're not even going to risk any sort of failure whatsoever, or even experience the slightest discomfort of making something and having it be bad, then I don't know how to help you because you have to meet me halfway. You have to try.”

Update your tactics

As worker productivity has hit mind-boggling new heights over the last thirty years and the gig economy is steadily taking over our lives, the midcentury “gumption” tactic has been replaced with asking a distant connection, or even truly random person, out for coffee to “pick their brain.” It’s an attractive little phrase to indicate minimal time waste: I’d just like to pluck some stray thoughts from your noggin! No worries if not!!

Everyone I spoke with for this article echoed the same advice: Be precise. Why are you reaching out to this person, specifically? What answers can they provide to your specific questions? What are you doing or working on that indicates that you could use their help in particular? Working from a place of shared experiences and specificity makes it easier for those you’re contacting as well as you to get feedback. As Sow says, “The lower the lift, the easier the request is to consider.”


It sounds simplistic, but just cutting out phrases like “pick your brain” or “shooting my shot” from a request could be the difference between hearing back and ending up in someone’s spam.

Shoot your shot

For many emerging creators, the desire to network with successful people in their fields serves as a useful tool in growing and learning, which makes accessibility an incredibly valuable tool. But boilerplate “pick your brain” queries create a lot of white noise that can be hard to cut through. It’s like trying to climb a ladder covered in trash, especially when the one person you could most use help from is dodging a bunch of unserious advice requests.

Everyone I spoke with for this piece had a focus on helping marginalized voices. As Conover puts it: “I have a vested interest in increasing the amount of diversity in my own business. That's something that I care about. So mentoring people who are trying to break into the business who could use a hand, that's the type of person I look for.”

“If a black woman emails me, I will almost always reply and help any way that I can,” said Sow.

“If someone's question is succinct and actionable, I am more inclined to respond. If I know the person and am familiar with their work/work ethic, I will also try to help.”

“I get messages from 21-year old white dudes who have just gotten out of an expensive college and say ‘Hey can I pick your brain?’ and I have nothing to say to them because A. They already have all the advantages and B. My advice would be the same as anyone else: Go do open mics. And if you can't figure that out yourself, well then I don't know, maybe you shouldn't be in the business. I have less time for people who don't need the help as much,” said Conover.


In fields dominated by cis white men (that is to say, most of them), the most valuable tool a marginalized person can have is deciding to take the shot regardless of whether they hear back. If the system is rigged against you, there’s no reason why you shouldn’t rig it back in your favor. Obviously just cutting ‘pick your brain’ from an email won’t be the solution, but the barriers and walls you’re up against are ones that can be broken down through developing genuine connections with people on your level, creating for the sake of it, and finding mentors who are on record saying they want to help voices that have a harder time breaking in.

Consider whether you’re just procrastinating

The accessibility that social media affords us – or at least the perception of it – is the perfect gateway to procrastinating, stalling ourselves in the “research” phase of our aspirations for fear we might not do the right things or take the right steps. I’d much rather ask my editor “how to write a good article?” than put in the work and write one. Obtaining the knowledge is easy. Executing it, not so much. And it’s in this viciously tempting copout where the harm flourishes like a mid-summer yeast infection. I don’t want to learn how to write a screenplay. I want to know how James Cameron sold Titanic, and I want him to tell me face-to-face because maybe while I am staring deeply into the place where his eyes should be, he’ll realize I’m the Chosen One and I should direct his next movie. Never mind the fact I don’t know how to direct.

The central harm may not be in the questions themselves—the busy folks further up the ladder likely won’t even see them. It’s what the questions represent: you, afraid of failure, telling yourself “there’s no harm in asking” because there is harm in trying.

The generic queries via Instagram DMs aren't the problem, except in that they often clutter inboxes and make it harder for people committed to holding the ladder steady to provide useful guidance to those who actually need it. But more than that, they're a symptom of our own insecurities. We’re using ideas like I just need to talk with Kathryn Bigelow about Point Break as an excuse to avoid doing the hard work. But a lot of times, it’s in that work that we find the answers. And if Nick Kroll, Lux Alptraum, Aminatou Sow, Lisa Hanawalt, or Adam Conover happen to see it? It’ll have been after a lot of trial and error and fearlessly growing into ourselves. And there’s no harm in that.

Be a nice person, be kind, help other people out.

A second universal piece of advice from the people interviewed here: in lieu of spray-DMing higher-ups you don’t know, make friends with people on your level. Whether you’ve just started working mics, illustrating, or writing, it’s more beneficial to connect with people on the same level as you. You can support each other, lean on each other in times of insecurity and celebrate each other in your successes. As your work grows and you climb that ladder, you’re going to want to bring friends along with you – and your friends will think of you as they climb, too.

Conover’s highlights an important aspect necessary for finding your place in comedy that’s really applicable for any field: “You should watch other people going up and you should observe who's doing it well, who's doing it poorly, who has good habits who has bad habits, who you think is funny, who you don't think is funny. Then you should meet those people, befriend them. Be a nice person, be kind, help other people out.”