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"I think it's extra hard for women and people of colour because we're so often told what our gut says is wrong or an over-reaction. Carving your own way out—of what's expected, of what you need to do to pay rent, or even your own uncertainty—is especially hard when now it's so easy to see or hear about other successful people online and off."
 
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I think a lot about timing whenever I hear about a mass shooting because the stories that come out of tragedy have so much to do with our conceptions about fate: how people end up in the wrong place, at the wrong time and at the wrong end of a weapon. Almost ten years ago, there was a shooting at my school. I still don't remember much of that day but I can never forget how adrenaline simultaneously fuelled my legs and made them feel light as they carried me out of a door.

The school was Dawson College, which is a CEGEP. If you are not familiar with this aspect of the Quebec education system: CEGEP a middle ground between high school and university. It’s a kind of self-discovery phase, where you can hold onto the last dregs of your adolescence and slowly put the feelers out into the world. At this age, you’re still too naive to grasp the immensity of a world beyond your bubble. And yet you’re desperately trying outgrow the guilelessness that binds you to your adolescence (if life hasn’t already done this for you). A few days after the shooting, two questions started to nag me. One had to do with timing—what if? The other had to do with intent—why? Eventually, I would force myself to stop asking these questions.

Just days after the shooting—before some of us could sort out what we saw and heard—the bullet holes in the walls were filled, the blood was scrubbed away, and shattered glass was replaced with new panes. The school quickly became a symbol for mending. Things looked and smelled new and with the signs of intrusion erased, it became even harder to ask those what if and why questions because there would be no simple answers. Eventually, I forced myself to stop asking these questions because I thought that this was how you moved on.

I think that sometimes we hesitate to ask questions because we’re either scared of the answers or we’re terrified there will be none. When I wanted to introduce Karen K. Ho, I wanted to talk to you about how she and I discuss not quitting a lot. Instead, I want to tell you that one of the many things I admire about her work is how she asks questions that don’t always yield straightforward answers. Case in point: Back in July, she wrote a powerful piece for Toronto Life about Jennifer Pan, a woman who, along with her boyfriend Daniel Wong, hired two men to kill her parents. At the end, Karen admits to being left in a “purgatory” of not knowing what Jennifer and Daniel “were thinking, feeling and hoping for” because both had declined her request for an interview. I still think about this ending because the question we always want answered the most is the one that is so out of our reach; the one that will likely never be answered. I think that how you deal with this ending says a lot about how you see the world—because sometimes there are still lessons that can be learned from the questions that are left unanswered.

Karen is a writer and a business reporter currently based in Yellowknife. (She’s set to come back to Toronto in January.) Here we discuss the thing that keeps her going and asking those questions: good advice. And here are the pieces we talk about, in order of appearance:

“Should I Be a Poorly Paid Writer or a Better-Paid Publicist?” from The Concessionist

Ira Glass on good storytelling and taste

This American Life’s Episode “The Giant Pool of Money”

(And finally, sorry for hitting you up in the middle of the night—MailChimp has been down all day.)

Sara Black McCulloch: You sent me a lot of pieces dealing with advice. Have you found advice more helpful in person or by reading it?

Karen K. Ho: It's a mix of both. I read the words sometimes at work, when I'm scared to reach out to people/friends/family/mentors. Sometimes I don't believe people when they tell me something similar in person. There's this weird thing in my brain where reading it is a different process. I think it's the lack of interruption, you get a chance to ruminate and reflect afterwards for as long as you need.

SBM: Do you find that it feels more objective too? Because, with an advice column, it isn't someone you know and there's this implied critical distance?

KKH: Yeah. It eliminates a lot of excuses.

SBM: What was it about Choire Sicha's advice that really struck you?

KKH: I think it was the idea that it [writing] was what I wanted to do, I just couldn't give myself permission. And Choire, who has done a lot—gone through a lot and seen a lot—was in a position to say in this column, "I am giving you permission. It is okay to take the jump. Things will work out." To clarify, I knew I wanted to write full-time, I was scared about the idea of leaving Toronto for Yellowknife. Choire's line about going hard and all the way—that was like an extra push to take a risk I wouldn't have taken on my own.

SBM: But he gives permission to make mistakes and bad decisions, too. Have you ever been scared of failure?

KKH: Yeah. I've been terrified. I grew up with a constant fear of mistakes and failure from my dad. It caused a lot of anxiety and low self-esteem. And I've been working on being kinder to myself about it for the last year and a bit. But hearing Choire, who has accomplished a lot, admit that he still makes mistakes too—that shouldn't be surprising but it helped normalize it a little more in my head.

SBM: Do you find that you're really apprehensive about the future? I wonder if you find some kind of solace in someone saying "I don't know what to expect either and it's ok”—the idea of working towards something and not knowing what that'll be or who you will be?

KKH: Oddly enough, I'm more optimistic about it. I have a few different plans depending on how things go in the next few months, but none of those plans are longer than the next year or so. I do have a better sense of what I want, what I do that makes me happy. And I've learned that little everyday things add up.
I have no idea what my career will look like or who I'll be even two years from now. I think that's something our generation has accepted right out of school. But I feel good about where I am now. And I think it was important how Choire reminded everyone we often have more time than we think to try stuff, fuck up, and try again.

SBM: Was there a particular time when you turned to advice columns a lot?

KKH: Yeah. When I had jobs that I really hated, where I wondered why I was there or dreaded going to work. Especially after I had been in them for a few months but didn't know what to do next.

SBM: How important is a writer's voice to you?

KKH: I think voice is incredibly important. I used to read Ask a Clean Person and Dear Sugar a lot and it was because of how they used voice to deliver advice in a way that dug deep into your brain and made you think. Voice is so powerful at conveying love, non-judgment, empathy, encouragement, sass and more. A writer's voice is crucial to building trust. It brings people back.

SBM: Sometimes it feels like a lot of what we do involves trusting the gut but also carving your own way out. You also sent me Ira Glass’ advice on taste. What did you like about his advice?

KKH: I think it's extra hard for women and people of colour because we're so often told what our gut says is wrong or an over-reaction. Carving your own way out—of what's expected, of what you need to do to pay rent, or even your own uncertainty—is especially hard when now it's so easy to see or hear about other successful people online and off.

I think Ira's advice about taste was important because of how it reminded people that most of us start off not very good, frustrated about that, and yet both of those things are totally normal. Even for a megastar like him. I really like how he emphasized the importance of hard work, diligence, persistence and the importance of not quitting in that weird middle period. How it's normal for it to take years of work before you make serious leaps in that gap between your ability and your taste. And to not forget that your taste means you know what's good, and you can use that to help guide you to where you need to go.

SBM: Who do you think is permitted, more often than not, to give advice? Who gets left of out these conversations? (Or who would you rather hear more from?)

KKH: I think white dudes will often volunteer or give advice without a second thought. I've asked women for comment, even informally, only to watch men jump in. I think it's how society has raised men and women to behave. And it's really frustrating sometimes to be aware of how the situation unfairly occurs all the time. I get tired sometimes when I see how advice columnists get treated differently because of their genders. I think the genre has earned a lot more respect in the last few years, especially with the popularity of Dan Savage, Dear Sugar, Ask a Clean Person, Heather Havrilesky, Dear Prudence, The Concessionist (Choire!) and The Ethicist. I think people of colour and non-Ivy League grads get left out of these conversations sometimes. I'm really glad that Denise Balkissoon and Desmond Cole have columns in major Canadian newspapers now, because even though they don't necessarily give advice, they do often give a lot of guidance about how people can or should think differently, and that's really important.

(Personally, I proactively ask for advice from other women, my mentors, my go team of close friends, other female writers like you, friends in the industry, sometimes my sister and my mom. Sometimes I ask for advice from too many people, mostly because I don't trust my own gut feeling.)

Also if Arabelle Sicardi started offering advice about relationships, selfies, makeup, dyeing your hair, navigating the ridiculous world that is New York Media or pretty much anything else, I would sign up for that right away.

SBM: Have you ever gotten good advice from women? Or do you find it's much more difficult for women to do so?

KKH: I've definitely received good advice from women. One of my mentors, CBC producer Ing Wong-Ward, gave me a talk at a student journalism conference once that I'm pretty sure I'll never forget, and my mom is one of the smart people I know. But I've also received some terrible advice from men. I think it definitely can be hard for many women to publicly talk about wanting to quit and struggling to keep going, but I'm lucky my female mentor, who is also named Karen, totally kicks ass, is very headstrong about what she wants to accomplish in life and has a very clear idea of what's she's worth. That has a huge impact on me.

I think the conversation is definitely changing rapidly and people are more open to talking about it. But there's still a taboo among women to some degree. And there's also a kind of competition and cattiness that can occur between some women that often discourages us from helping each other.

SBM: How important has mentorship been for you? I find that today, it's less of a thing—there's less guidance/general pooling of advice when it comes to people's careers.

KKH: Mentorship has been incredibly important to me. I think my main mentor has been in my life for at least 6 years, possibly 8 or more. A really, really long time. They've watched me, my career and both of those things evolve in a way that has been incredibly valuable. Their decades in the industry also give me a perspective that crosses so many workplaces and experiences I could never access otherwise. And it helps they're also a person of colour, because they've gone through everything already. I can't remember making a major career decision without consulting them first.

I also try to mentor younger writers and journalists when I can. They're mostly female and often Asian due to my membership in AAJA. I don't know how good I am at it, but I'm always open to helping other people avoid my mistakes, benefit from my experience, and learn all the stuff I wish someone had told me when I was their age. I always tell them to hoard as much money as they can, learn how to cover business because it's useful for everything, and to join organizations like AAJA while they're still in school.

SBM: Do you find it difficult to sit back and recognize your own progress?

KKH: I have to go to other people. I've learned it's really hard for my brain to recognize progress. It primarily registers setbacks, mistakes and failures. I've been really lucky to meet some incredible people who are very good at helping me recognize the progress I've made in a way I can't excuse away. Talking to them is important for me both professionally and as a form of self-care.

SBM: Is it difficult knowing when you're getting better?

KKH: Sometimes. The work I do here in Yellowknife—there are definitely moments I hear from my editors about stuff, good and bad. Other times I feel like I'm just trying not to drown in my own feelings of being overwhelmed by my workload or how little I know about this place. I know I push myself pretty hard. But sometimes it definitely feels like I don't do it enough.

SBM: Do you find you push yourself more in life than in your work (writing)?

KKH: It's hard to say. I feel like so much of my life now is about my work. I used to rock climb and work out a lot, and I could physically feel how I pushed myself outside of my day job. I worry sometimes about things like what I'm eating, the shape of my body, my lack of physical fitness, how often I'm in touch with my family, how little I socialize. Other times I think about taking more interesting photos, writing better articles, or how to reduce stress on deadline days.

When I wrote this essay for The Walrus, I felt physically drained afterwards. But a friend said that was a good sign, it meant I had really put myself into it.

SBM: What do you find sustains your attention in a long-form piece? What do you focus on in your own writing and reporting?

KKH: It's always the details. The feelings you get after reading a particular section. The reveal—a moment, an emotion and/or a detail you never expected. The pull towards a period of time or lesson you're hoping to find at the end that wraps everything together.

With The Walrus and Toronto Life pieces, it was scenes, like where I talk about people crying in different places from work-related stress. In the Toronto Life feature, I knew from reading great examples that things like the flavour of Doritos, the congee, the time marker in the 911 call would all be important.

SBM: You were telling me about a This American Life episode ("The Giant Pool of Money") and how it really drew you into business reporting. Was this the first piece that really got to you?

KKH: I think it was how it explained a really complicated financial instrument in a very patient, careful way that the general public could understand and comprehend in terms of its catastrophic impact on everyone. They [Alex Blumberg and Adam Davidson] just waded through all the jargon and terms and helped people who would never otherwise come across this information understand it. They made it enormously accessible. It was incredibly inspiring for showing the power of translating this kind of specialized subject for the general public. Also the way that This American Life episode was set up—that the producers were allowed to react very honestly to what they were learning. You feel like you're learning along with them. It made this subject far less intimidating than it could have been.

SBM: Why were those reactions significant to you?

KKH: I think it comes back to your question of voice. In this case, what happened was really shocking. It had huge ramifications. And the way the producers reacted I think confirmed for a lot of listeners they weren't crazy, they had a right to feel confused and completely taken off guard by what happened with CDOs [Collateralized Debt Obligation] and credit-default swaps. For a long time, business was seen by the general public as a serious, stodgy beat. But “The Giant Pool of Money”  showed it could be full of drama, twists and levels where people are tricked in complicated ways. And more importantly, how we got to the point that caused the financial crisis.

SBM: Why do you write? We've been talking about voice quite a bit and this internal monologue, and I wonder if you've always felt this way: that there is sort of this voice narrating along. What do you think drives your own writing? And how do you listen to your own instincts and trust your own voice?

KKH: I write because I realized a few years ago if I didn't try to do it I would wonder and regret it for the rest of my life. I like doing it. I like trying to get all the weird thoughts in my head out to great friends like you, family, strangers. I write people long emails and postcards. I scribble in journals. I am addicted to putting out mini essays full of feelings on Twitter.

I know words are powerful and I like how they can help people. I've written blog posts about advice for the Inca Trail, personal finance stuff for the Financial Post and that thing for The Walrus was stuff I had been talking about with friends for years. I also now know I have a lot of weird, interesting, detail-rich stories. Writing helps me alleviate the worry I'm missing details the next time I want to tell it to someone new.   

Reading other people's work drives my writing. Sometimes the bad stuff too, only because the world really does not need me to add to that pile. I like the idea that I am adding to world. I like pulling research, interviewing people, going to events, translating financial stuff like statements or quarterly reports and convincing people to care about it through my work. Being a reporter and writer literally allows me to meet lots of people, do interesting things, be nosy, ask questions, prompt debates. A lot of that I never had while growing up. My mentor says my career path was not an accident.

I didn't know how to trust my own voice until this year. Honestly. But then after the success of the Today in Tabs internship and the Toronto Life piece—both of which I was scared were flukes. I recently angry-ranted again on Twitter about Jon Kay's appearance on The National and The Walrus's online editor [Matthew McKinnon] reached out. I should mention finally this year I realized I am funny, sassy, observant, empathetic, sensitive and kind. And all of those things show up when I get to write things like the meritocracy essay or guest intern for Today in Tabs.
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