Dear ____: Advice on writing an advice column

We invited several Substack writers – Yanyi, Kirstie Taylor, and Default Friend – to share their insights on advice columns during our 2021 Substack On! Conference. All three writers grew their audiences by providing thoughtful advice to readers who submit questions through their newsletters.

  • Yanyi writes The Reading, a newsletter of writing advice. He is a writer, poet and critic, and author of the poetry collection The Year of Blue Water. He’s also the poetry editor at Foundry

  • Kirstie Taylor writes Words With Kirstie, which offers advice to the hopeful romantics of the world. She's a dating and relationship writer and the author of the forthcoming book, What I Wish I Knew About Love from Thought Catalog Books.

  • Default Friend is the author of the newsletter Default Wisdom, an advice column about startups, culture, and relationships, with occasional bouts of serialized fiction.

The conversation was moderated by Sophia Efthimiatou, who’s on the Partnerships team at Substack. This transcript has been lightly edited for readability. 

You are all very good at giving advice. If you could go back and give yourself one piece of advice for when you first started doing writing, what would that be?

Yanyi: When I was living in New York City, I had so many conversations with emerging writers who were struggling with their writing. And it often had to do with something else that was going on for them that they needed help on. Usually, they would come to me with a question about something they're trying to do in a book, and then we would end up talking about their life. So it seemed like a very natural thing for me to start an advice column.

If I were to give myself a piece of advice from when I started The Reading, it would be that things will happen for me and that things will come and it's just a matter of working on it every single week. What’s been magical for me has been discovering that people who love my newsletter, really love it, and have really supported it in a way that I didn't know could be possible.

You just have to go for it at some point and not have high expectations. You never know where an opportunity could lead.

Kirstie Taylor: You just have to go for it at some point and not have high expectations. You never know where an opportunity could lead. At some point, you just have to start, you just have to write your first thing. The best advice that I would give myself is to just keep my head down and focus on the content that I really want to produce, and be really authentic to myself. Because if you look around and read everyone else's Substack, or look at someone that's been in the game for 3-5 years, and compare your beginning to where they're at now, that's going to feel so overwhelming. I compared myself a lot and it just made me feel like I had imposter syndrome, or like I wasn't good enough.

Once I just started focusing on my unique voice and thoughts, and just became more authentic to myself, that's when my newsletter started to get a lot better. So that would be my biggest piece of advice: just focus on what you're doing, and don’t really pay attention to what everyone else is doing and compare yourself.

Default Friend: The thing about starting at Substack is it reminds me of starting a blog or a podcast. I've had this conversation with people a bunch of times, and they're like, “I want to start a Substack, but there's so many already in the niche that I want to be in. How do I distinguish myself?” There's two answers to this. One, there's never too many blogs, right? Like when blogs were the medium, there was an infinite number that you could go to and people were still reading them. There's almost no way for it to be oversaturated.

Secondly, this is a really funny analogy, but I think of the “dirtbag left” podcasts. I remember when Chapo Trap House got really popular, and that was the first one to really hit the mainstream, it was like, “There can only be one podcast like this, there's no way.” Then people were like, “All right, there's two podcasts like this, there's no way.” And then here comes Red Scare, and it's like, “Okay, there's three podcasts like this, and they're all making $65,000 a month off Patreon.”

And people were like, “This is really oversaturated.” And then here comes TrueAnon. If the content is good, basically, it will always elevate. As far as the advice I would give myself, I don't know. My Substack started as an events list and COVID turned it into advice. I am guilty of taking very long breaks. So I guess it'd be just don't stop writing. Just keep doing it even if you change course.

How do you distinguish yourself from everyone else out there?

Kirstie Taylor: I got hung up on that a lot at the beginning of creating my Substack. There's so much relationship and dating advice out there. I found that really the only way to differentiate myself was to write from personal experience, and in my specific voice and humor. And that alone set me apart from other people, because no one's going to have the same story as I did, or the same conversation with people that I have.

I found that really tapping in and focusing on my voice, rather than what could drastically set me apart content-wise, ended up being the better strategy. That's a great strategy for a lot of people. It doesn't have to be this wildly new concept, you don't have to reinvent the wheel, you just have to tweak it a little bit. And that tweak could be your unique personality.

I found that really tapping in and focusing on my voice, rather than what could drastically set me apart content-wise, ended up being the better strategy.

Nowadays, people greatly underestimate how much we just really love to connect with the person, like your favorite podcast host or like your favorite writer. Their ideas are great, and they might not always be these totally new ideas. But it's their personality and the way that they look at things and the way that they think about things that people really connect with.

Yanyi: The thing about giving advice, especially if you're doing it in letter form, is that your content is driven by your community. The people who write to you, and the people who read, are the same people. So for me, I wasn't really calibrating as much. I noticed that some posts would get more traction than others. Maybe they hit a nerve in a way that was a little more significant or salient to people in a given moment.

But basically, the way that I move around in my content is I see that these letters are evergreen. Like if you've ever read Letters to a Young Poet by Rilke, that's evergreen, because it's really about life advice and about helping someone who's feeling as though they might find an answer somewhere in your words.

I started doing audio a few months in because I noticed that, especially because of pandemic, I was spending so much time on the screen. I wanted all of these newsletters that I was reading to have some audio component. I often use the screen reader on my phone, because I cook and bake a lot, and I'm just listening to things all the time. When you're walking with a friend, you're taking a walk and you're not actually looking at them. I want people to be able to have that experience when they listen to my work.

When you're walking with a friend, you're taking a walk and you're not actually looking at them. I want people to be able to have that experience when they listen to my work.

That's a perk for subscribers. I put audio behind the paywall because you can still use your screen reader, but it does take extra work to do the recording. There’s this whole setup in my partner's room where we have a closet that has this cut-up mattress pad with recording things. It takes time to put that together. So I'm learning a lot in terms of how much I want my work to be valued.

How do you deal with difficult questions, and what is your process of selecting which questions to answer?

Default Friend: When I get heavier questions, I make sure to display it like, “This is just my opinion. It's my perspective.” And that if it doesn't resonate with them, that they should search inside themselves to see what feels right, or ask a family member or close friend.

I do try to take it seriously. When I'm answering questions like that, I try to literally imagine what I would do if I were in the same exact situation, and then think of all the possible ways that different actions could play out.

Oftentimes when I'm giving advice, I give people a list of questions they should ask themselves – so if the actions that I propose don't feel organic, they know how to suss out an action plan that they've created on their own. I think that is a big thing with advice: a lot of people don't know how to ask themselves questions, and giving the right questions to ask is just as valuable as giving concrete actions to take.

I think that is a big thing with advice: a lot of people don't know how to ask themselves questions, and giving the right questions to ask is just as valuable as giving concrete actions to take.

As far as how I choose questions, it's difficult and it's easy. I get a very high volume of questions, but most of them are the same. I would say that if I get around 300 questions a week, 275 will be a generic relationship question that I've usually answered three or four times already. If I'm seeing something come up a lot, I will answer it in slightly different ways.

The other thing that I get over and over again is, “I'm an incel. I feel completely alienated from the world around me. I don't know what to do – what city should I live in, or how can I break free from my situation?” And I don't feel super comfortable speaking to a more masculine or male experience. I have tried to answer it a couple of times, but I don't want to pretend like I know better. So then, the remaining questions are the ones that I'll end up answering, because those are the ones that don't fall into one of those two buckets.

Kirstie Taylor: I find that I tend to gravitate towards answering questions that I can have more personal thoughts on or have more experience with. If someone comes to me, and they're like, “I am 60 years old, and I'm divorced,” that's going to be very hard for me to relate to. I've never had any super deep questions where I was like, “Oh, this might be too much.”

For any advice on deep questions that I give, at the end I'll say something like, “These are just my thoughts, and if things feel too overwhelming, I highly suggest seeing a therapist. It's worked well for me, and there are affordable ways to do it nowadays.” But I usually gravitate towards questions that I feel like I have the ability to answer, because I don't want to be grasping at straws on a subject I've had zero experience with that would be better handled by someone else.

Yanyi: There are questions that come in where I'm like, “I don't know how to answer this, and I need to let it marinate for a little bit.” But those are also challenging and interesting. I do get a lot of similar questions – a lot of people have similar roadblocks when they start writing.

Like Default Friend, I've answered certain questions more than once, but in slightly different ways. Sometimes you'll get a letter that asks like three questions, so if you've exhausted two of them, you can answer that one question that you haven't answered already.

Also, my identity matters as the letter responder. For example, I get more questions specifically from Asian-Americans about-Asian American issues in ethics and in publishing. Those are questions that I'm grateful that I get to answer, because those are literally things I've had to think about by myself or with a small coterie of friends that I get to do in public. That's part of the consciousness of what I end up choosing to respond to: is this a question that most likely I'm one of the only people who give public advice on?

What has worked for you in terms of monetization?

Kirstie Taylor: Actually, my newsletter is all free right now. I'm focusing on giving my best content away for free as long as I can. I make a full-time living writing on a different platform, where I direct all of that traffic to my Substack. That's how I accumulate newsletter subscribers. I'm still deciding what exactly I do want to put behind a paywall, because it is my goal to make a monetized newsletter. But until I feel like I've really gotten to the point where I have something that I want to have everyone pay for, I like keeping it free.

A lot of people succeed by giving away their content for free for a long time, accumulating a big audience, and then finding something that they want to put behind a paywall. I think it's interesting how Yanyi monetized with audio, and I've been considering the same thing because I used to have a podcast. It's a very interesting concept to have a newsletter where you can hear someone's voice along with the words.

Default Friend: I'm in a weirder boat because I tweet over 100 times a day on Twitter. And I post on Substack a lot too. So for me, monetizing and putting stuff behind a paywall is to protect my audience from me. I'm dead serious: you will get 20 emails from me in your inbox if you are paid. The people who really want it are going to pay for it, and the people who are like, “I don't need this much Default Friend” can get the regular-flavor newsletter once a week. That way, I can be super manic and frenetic with my posts and say what I want to say.

Yanyi: That is actually a funny thing about the Substack model: you have to balance protecting your readers from getting too many emails from you. Like if they sign up, they must really like hearing from you because they are inviting more emails into their inbox. I think that says a lot about who subscribers are and how much they want to be in your community and have access to the things you have to say.

A funny thing about the Substack model is that you have to balance protecting your readers from getting too many emails from you.

My main advice letter, which goes out every Sunday, is completely free. I've written many times that it will stay free and that I have no intention of putting it behind a paywall. Part of the reason that I started the newsletter was because, unless you live in New York City or LA or go to the Iowa Writers' Workshop, the amount of information that you can get about being a writer and what the industry is like and finding mentorship is extremely difficult. A lot of people who read my newsletter are writing in a place where you may not expect to find people engaged with the writing industry. The point of the newsletter was to make it more accessible.

For the audio part of my Substack, the idea was to create the product I want from other Substacks, which is for someone to read things out loud so I don't have to read myself, because my eyes hurt. That created the model for me to follow my ethics a little bit, while also creating something that I could give to subscribers once I went paid. I'm still tinkering with what I offer behind the paywall, because right now my conversion rate is lower than 10%, which is considered “good.” 

Was there ever a moment that led to a big jump in subscribers?

Kirstie Taylor: It's always interesting to see what resonates with people and goes viral, and what doesn't. I had a lot of success with getting really specific to a relationship psychology theory called attachment style. I’ve always found that this type of content brings in a lot of new readers. Maybe it's because anxious people are more likely to go looking for answers and wanting to fix things, but whenever I write about anxious attachment theory, people come flooding into my newsletter. 

Or maybe they can tell that I'm among them, and they're like, “I resonate with this girl.” I like that my readers can resonate with the type of feelings that I feel, because it is harder to write content for people that are on the exact opposite spectrum as me. I get emails from them like, “This newsletter resonated with me so much – you went into my brain and picked out everything that I was thinking that no one's ever said.”

Default Friend: I've had three posts that have led to huge jumps in subscribers. The first one got posted to Hacker News and did pretty well there. It was about what to do when you have imposter syndrome but actually are under-qualified, which I don't think is discussed super often. The second one that did pretty well was when somebody asked me if they should start an OnlyFans. In my answer, I didn't give them a clear yes or no, but I basically proposed that sex work isn't for everyone, but it works very well for the people for whom it works. With the third one, I wrote what basically amounted to fan fiction about Bitcoin. For some reason, people loved that one.

Yanyi: I feel as though my newsletter is successful because of the ongoing ethos of what it is. It's less about content than it is about the way that I write about what I'm writing and the kinds of questions that I answer. But I've had a couple of recent jumps. My newsletter was recommended by the artist Kim Lam on the newsletter Dense Discovery in December. It seems very popular.

I also wrote an advice column about a dilemma for this Chinese American writer who was asking about how to write authentically about identity, and I basically responded very honestly in the terms that I had figured out for myself – and the writer Alexander Chee, who is way more famous than I am, tweeted it and posted it on Instagram. That was the first huge lift that I got, so I have him to thank for introducing me to a bunch of new readers.

Read more resources for writers.