Tim Herrera On the Writing Hacks That Will Drastically Improve Your Freelance Career

                        

  

Photo by Earl Wilson

For all of the interest in freelance writing, it’s surprising how little good information is available on the topic. Tim Herrera is the anecdote to that. The former New York Times journalist now runs Freelancing with Tim, a newsletter and consulting service that offers advice, insight, and guidance into freelancing.

On the pod, Tim offers invaluable advice on starting a freelance hustle, from building your digital presence to crafting the perfect pitch. He gives an overview of the freelancing landscape today, and what strategies you can implement to put your best foot forward. Tim and Jon also talk about drawing the line between your work and your identity (which can be really hard as a writer), and how helping others uplifts everyone in the industry.

Here’s a transcript of the interview:

Well, Tim Herrera, welcome to the Write About Now podcast.

Tim Herrera: Thank you so much for having me on. Glad to be here.

Jonathan Small: I am so excited to talk to you. I've been a fan of your writing for a long time. And it was funny, I was reaching out to some friends, I was like, I've got to get a really good editor on the show. Somebody who understands, you know, how to pitch publications. And somebody's like, have you talked to Tim Herrera? And I was like, Tim Herrera? That would be awesome. And then I looked you up and wow, you are like right on the nose as the guy that I should be talking to that I think can really help our writers and listeners understand the sort of inner workings of editors and what they look for in pitches and how to work well with an editor and that kind of thing. So I'm so excited to have you on the show. Before we get into what you're doing now, I'd love to talk about from whence you came, and a little bit about your origin story. How did you break into the business?

Tim Herrera: I've been doing this for, now, I guess, like 11, 12 years. I've been lucky enough to basically have steady employment since graduation. So I went to NYU. I studied anthropology and journalism. And pretty much, right after graduation, was lucky enough to get an internship that summer. A newspaper here in New York City called am New York. And am New York is owned by Newsday, so by extension, I was able to write and report both for am New York and Newsday. So it was like an amazing experience. And, you know, am New York was a relatively small newspaper for the market, and the staff was relatively small as well. But that was perfect because it essentially meant that I could hoover up all kinds of responsibilities, that if I were interning at a larger paper I would never have the opportunity to do.

And so this is why, you know, anytime I talk to students, I always say like, sure, if you can get the Washington Post internship, the Wall Street Journal internship, great. You should not turn that down. But, you know, if you're not getting those huge ones, like I think getting out of major media cities and working for smaller outlets, smaller newspapers, smaller websites, whatever it may be, really opens up the opportunity to just start exploring things that you would never have the opportunity to do if you're interning at a larger paper. So I interned that summer and then somehow tricked them into hiring me right after the internship. And so I started as a reporter writing for am New York and Newsday full-time, which was amazing. And it was really - a lot of it was right place, right time. Because I was very young, especially for Newsday. I kind of got a lot of the - what we would call back then - digital responsibilities or online responsibilities just kind of shoved on me.

Jonathan Small: Because you're the kid, right?

Tim Herrera: And, you know, was able to kind of spin into those really hard and developed this relatively wide set of skills that eventually I was able to leverage for a job at the Washington Post.

Jonathan Small: Nice. So it paid off to get the small job and then, yeah. Which is not that small by the way.

Tim Herrera: Totally. And, you know, it was perfect. Like I was able to get that job because I had done so much for the small paper. So this was maybe 2014 when we were all still kind of figuring out the internet, we didn't really know how to do social well, SEO was still a real black box, but I happened to have skills in most of those areas on top of reporting and writing skills. You know, one thing that I always like to tell writers is, being as well-rounded and having as much of foundational knowledge as possible in a lot of different areas is such an advantage. I've been on many, many hiring panels over the years, and a lot of times, the best candidates are those who can do a small handful of things exceptionally well, but also can do a bunch of secondary and tertiary things also pretty well. That's the kind of trick that I've been using for my whole career. I think it's been working okay so far.

Jonathan Small: Yeah. I think there's many hyphens these days with writers. It's not just like, I'm a science writer, you know? It's like, I'm a science writer who also has experience in social media and has SEO experience and can also write about relationships. I mean, I think the days of sort of specializing in one thing are probably gone. Because I've been in this game a long time and early on I would tell people - in the nineties - oh, you've got to specialize. It really helps to specialize in one thing and be good at one thing and then people know you're that writer. Like, who's my health writer I can call about this story? But I don't think that's really true anymore. I think it's changed.

Tim Herrera: This is a question that I get so much. You know, I do a lot of coaching and working directly with writers and freelancers now. And one of the most common issues that comes up is, should I be a generalist or should I have a specific beat? And this is particularly an important question for freelancers. Because, you know, when you're on staff, generally you're going to have something of a beat if you're a reporter. Or at least a general category that you're focused on. But if you're not in that system and you have the ability to do everything, I'm of the opinion that I think you should lean into that.

In the writing that I do now as a freelancer, I do a little bit of everything. You know, the writing that I've done throughout my career, I've done a little bit of everything. And to me, that just seems more interesting. But on the other hand, I know so many freelancers who are known as the person for X, and they make careers out of that. And I think that's great too. So I think a lot of it really comes down - you know, there's no right answer. It's just like, what sounds fun to you? It's really the way that I always answer that question.

Jonathan Small: I think that's so important. It's like, what do you wake up and want to write about? If you're somebody who just loves writing about, say, science and health stuff or let's just say you're a health writer and that's really what gets you up in the morning, then yeah, that's fine to specialize. But if you're like me - and it sounds like you - and you're kind of interested in a lot of different things and don't have one specialty, go, I think, be a generalist. I think that's totally fine.

Tim Herrera: It's fun. You can do a little bit of everything. I think it's great.

Jonathan Small: Yeah. Alright. So you're at the post and that's a big job and you're pretty young, what brought you to the times? Because then you went to the New York Times, Right? I mean, I don't know if I got that right, but it seems like that was the next step.

Tim Herrera: Yeah, that's great. So I was at the post for a little under a year and a half. And when I was there, I was doing reporting and writing and I was also producer working on the social team. So doing a lot of social stuff, a lot of audience stuff, a lot of growth stuff, SEO stuff. And again, this was 2014 when we were still kind of figuring this stuff out for ourselves while we're doing it. Again, I was able to take this skillset that I had brought to the post and really expand it and just super go really, really big with it, because it's the Washington Post. And so that was just like an unbelievable training ground and a place where I was able to implement ideas and things that I wanted to do in ways that had a lot of impact and had a lot of scale.

And so from there, it's kind of a weird trajectory. The editor who hired me at the post, about six months after I started, took a job at the New York Times, on the New York Time's audience team. Maybe six months after that - he's a real mentor figure for me, and we always stayed in contact - but about six months after he went up, we kind of started having conversations and it turned out I had a skillset that filled a lot of what they were looking for on the audience team. Not even a year and a half after I started the post, I went up to the times and I joined the audience team. The job was called growth editor. That's a very ambiguous and a very -

Jonathan Small: Very 21st century, right?

Tim Herrera: Like, what does that mean? Like, I had that job and I don't know what it meant. But so, essentially, what the team of growth editors, which was within the wider umbrella of the audience team, what we were focused on was growing audiences, but more specifically, getting New York Times journalism in front of people who wanted it but weren't necessarily getting it, didn't know what we were offering and just implementing smarter strategies on how to do the internet as a large international organization. And, you know, this is a never ending battle and the stuff that we were doing in 2015, 2016, is wholly irrelevant now, just because it changes so fast. But we were out to kind of grow and adapt, and I think we had a lot of wins and successes. From my time there, that was really a stepping stone job.

I did that for about a year, I want to say. But for kind of the tail end of that year, I and the editor who hired me - the one that I worked with at the Washington Post - we kind of had this dream of doing something around service journalism. We weren't sure what that thing was, but we knew that there was a hunger for it based on research that we had done on the audience team and what we knew to be coverage that the times could do to improve on. And we knew that service was a really big part of that.

Jonathan Small: And by service, just for our listeners, it's advice. It's how to improve. How do you define service? I guess so.

Tim Herrera: Correct. Yeah, we define it very broadly, essentially as any journalism that helps readers live a better life, whatever form that may be. A lot of right place, right time, while we were kind of thinking about this, one of the mass editors there - who is one of the top editors in the newsroom - also had dreams to do something around service. And so, put two and two together and we were able to - after four or five months of pretty intense research and testing - launch Smarter Living, the times first standalone section that was just dedicated to service journalism. And that was 2016. And then I did that up until the summer when I left the times.

Jonathan Small: Yeah. And let's talk about Smarter Living for a minute. It is a great column, section, whatever you call it, and how many stories did you - when you were doing Smart Living, you did that for a number of years. I mean, you must have written hundreds of stories, right?

Tim Herrera: That was a perfect job for me, because it really called on all the skills that I had spent the previous seven or eight years developing. Because my primary role was editor, but I also was the writer of the weekly newsletter. I was also a writer of stories in general. I was focused on building the community for it. I was working with the social team, I was working really closely with the SEO team. And so I kind of like had so many different roles within that. Again, like, right place, right time. I had the weird primary, secondary, tertiary skills needed to launch this new thing. I'm very aware that like - again, right place, right time. But it was great. You know, over the years, I edited, probably, thousands of stories, wrote hundreds of stories, built the newsletter into one of the most subscribed to newsletters in the newsroom, had this huge engaged community. It was like, I don't believe in dream jobs, but it was about as close as I could come to a dream job.

Jonathan Small: Alright. So here comes the million dollar question. You left this dream job, right? I mean, a lot of people, if they had that kind of a job, I would think most of our listeners, including me, if I had that kind of job, I would probably be like, this is a dream job. I can never let this one go. And yet, you made a very bold decision to leave at a certain point. Can you talk a little bit about why you left?

Tim Herrera: It was the combination of like 18 different things coming together and really, at the core of it, the pandemic kind of forced my hand. That's the wrong term. I don't want to say forced my hand, but the pandemic was the push I needed, I'll say. As it relates to the pandemic, I - like so many other people - just got super, super burned out. Was really just having such a rough time with the pandemic a year, year and a half in. So I just kind of needed to take a break, get off the mountain for a little bit. And so I did. I took a couple of months off. In that time, I really thought through what I wanted to be doing over the next couple of years, what I wanted my next move to be, whatever it was. And so I went through so many iterations of this conversation with myself to think through like, when I go back, what do I want to be doing? Do I want to go back? Do I want to stay in media? Should I just go live on an island somewhere? All these crazy different thoughts. So that's one track.

Jonathan Small: So before we move on to the next track, what was it about the pandemic? I mean, it would seem to me - and if you don't mind, if I'm getting too personal, let me know. It would seem to me, like sometimes, in terms of the pandemic, it simplified things a lot for people because now you're working from home, you don't have as many distractions being in the office, you're kind of like your own boss at this point. What was it about the pandemic that kind of pushed it to a different level for you and kind of caused you to be more stressed about it?

Tim Herrera: So Smarter Living was particularly well positioned to cover the pandemic. Because, you know, we've been doing service for - at this point, it would've been five and a half years. And so we really had the infrastructure already built to switch gears extremely fast and do nonstop Corona, Corona all the time. Again, solely focused on service. I was very honored and thrilled to be able to offer that type of coverage and that service for people when we all had no idea what was happening, and we were all figuring it out together. Like, we were writing this coverage and we were also living it. So it was just a very weird combination of things. At times, felt really relentless. And everybody in the media switched gears and was only doing Corona stuff.

But it was just really intense, like it was for everybody. I think, like a lot of other folks who just felt burnout, it was just the combination of that plus working from home plus not being able to see anybody plus not being able to go out, all the stuff that we all dealt with for whatever reason just really hit me that winter and that spring of earlier this year in a way that just felt unsustainable. And it's hard to kind of pinpoint it, but it was the combination of one thousand things. And it just led to this moment where I was like, I need to do something drastic or I'm going to have a fucking crisis. It was time to just like step away and take some time off.

Jonathan Small: And you took some time off and the New York Times allowed you to take a little time off at first, right?

Tim Herrera: Yeah. They were super, super flexible with that. I should just write about this, but I've been telling people, everybody about this. So I live in New York, and in New York - this is relatively new, over the last couple years - you can take what essentially amounts to paid mental health leave. Which is what I did. So I was out for two months on that. You know, times couldn't have been more helpful and more amenable to that. Very understanding. I know of other folks in that newsroom who've done the exact same thing this year. So quick aside, if you need mental health time off, ask your manager, there are systems in place to do that.

Jonathan Small: Okay. Well that's good to know. You know, it's interesting. So here you are, you've written thousands of stories, edited thousands of stories of giving advice about how to handle - I'm sure you've written stories specifically about the situation that you were going through in your life. Did you sort of feel like when it was actually happening to you, it was a little different than offering advice to other people? I ask this because for a long time I wrote a relationship column for Glamour Magazine then Kozmo. I would always tell people, I was pretty good at giving advice, but when I had to follow my own advice, it was harder. It was a lot harder. Did you find the same experience where it's like, oh my God, I should know how to handle this because this is all I write about.

Tim Herrera: It's such a good question and it is extremely accurate and true. So earlier this year, kind of like January, February, like in the dead of winter, when I was really starting to feel the effects of this burnout, just like all these mental health issues and just feeling exhausted all the time, it was doubly frustrating. Because I have built a career on offering people advice on essentially how to dig themselves out of these scenarios. Like, I have written stories about burnout, I have edited stories about burnout, like, I know all the tricks, I know all the strategies, I know all the things that you're supposed to do. And so it was frustrating for me to know what to do and to have given advice to people on what to do, and yet I still couldn't pull myself out of it. And so that just compounded it. And that was certainly a factor in, I think, why I was feeling the way that I was. Because I know the strategies to get out of burnout and I tried to implement them and did everything I could, but nothing was working. So I was like, well, do I even know what I'm talking about? Like, do I actually know the strategies? I'm doing everything that I think works, but it's not working. And so it was just this snowball effect of the frustration - built on frustration - and just kind of cascaded in a way that, like I said, reached a point that was unsustainable.

Jonathan Small: And so you said that was one track. So you were having this kind of existential crisis fueled by the pandemic and you took some time off. And then eventually when did you make this decision to kind of actually cut ties with that life and start this new one that you're in right now? We'll get into that.

Tim Herrera: Yeah. So for a couple of years, it's been in the back of my mind that I really kind of wanted to eventually work for myself. Wanted to kind of try something a little more entrepreneurial and just dedicate myself to something that I owned. Timing - again, like my career is built on right time [20:44 Inaudible]. So last year in the early days of the pandemic, I started kind of a nights and weekends project called Freelancing With Tim. And that was a project where I was writing a weekly newsletter and hosting weekly zoom panels all based on navigating the industry from the perspective of an editor who's been editing for a long time, someone who's been a reporter for a long time, basically doing everything that I could to kind of give back to the freelance community. Because when I was an editor at the times, probably 85% of the work that I was editing was from freelancers.

And so it felt like a good opportunity to give back to that community. And also just kind of democratize information. Because being a freelancer is so difficult for the silliest reasons. And one of those is that it's really hard to find basic information about being a freelancer. About what the expectations are of editors. Like how to write a certain type of story. This information like, you can go to school and spend $40,000 getting that information. But I really wanted to democratize that and provide a resource where you can find all that information for free. So I did that in last spring, spring of 2020. And did it until December when I really was feeling the effects of burnout and it just felt unsustainable. So, the reason I mentioned that is, when I was taking my time off, as I was kind of going through what next steps were, what I wanted to be doing in the back of my mind, I was like, well, I've always wanted to do something entrepreneurial work for myself, do something that I owned.

And I had already built the infrastructure and the product to do that. So then, you know, kind of connecting the dots, I was like, well, if I did strike out on my own, it's a pretty soft landing. Because I had a very large audience, the tools and infrastructure to do it, I wasn't starting at nothing. I was starting at a place where I had already kind of done most of the hard setup. And so it was really, like I said, a very soft landing. You know, the combination of all these things. And then the last kind of track that was most significant was just the idea of working for myself. I had been extremely fortunate to have full-time employment for my entire career since graduation, and so I'd never seen what the freelance life was like, what the entrepreneur's life was like and it has always just seemed really appealing to me. And so irrespective of the pandemic, irrespective of Freelancing With Tim, just the idea of working for yourself was an idea that I always thought was really interesting, but that I never really had the right idea to do it with or the kind of - there was nothing that was pushing me out of the nest to do that.

Jonathan Small: Yeah. I mean, you've got the golden handcuffs.

Tim Herrera: I had great jobs. And like, what kind of idiot leaves a fucking editors job at the New York Times, right?

Jonathan Small: But you know, there's more and more people following your example. I see a lot of journalists that I always really enjoyed reading and now have Substacks and they're kind of doing - they've broken out into it. So it's definitely something that people are doing. It still takes a lot of bravery. I think one of the lessons to take away from you is that you did sort of have already a side hustle that you had while you were gainfully employed. And I think that's kind of a wise move rather than do kind of like, just quit cold Turkey and have nothing going on and being like, I'm going to do this. So you did have this side hustle going on the side, right? Totally.

Tim Herrera: And you know, this is something that - I talk about this all the time on panels, on my coaching calls, on anywhere I can spew this idea. Even for folks who are gainfully employed and who do have a full-time job they love, great. The industry is just so precarious, now more than ever. But the pandemic in 2020 when we're seeing newsroom budgets just slash and all of our colleagues were getting laid off, newsrooms were closing, it just, I think, really put a point on the idea that as a journalist, you always need a plan B. Even if you feel comfortable, you know? Like, I feel like I had probably one of the most stable jobs in journalism, but I still knew that at any moment the other shoe could drop. And so I think no matter how comfortable a person feels in a position, I think anybody working in journalism needs that plan B. And so for me, that turned out to be - initially, it was book writing.

Like I sold a book, and that was going to be my plan B. But then, the Freelancing With Tim project came up and that turned out to be my plan B. But I think it's just so important for anybody to start building out a presence and identity that is disentangled from the place you work. Because that's what it is. It's a place you work. And I think as journalists, we love to build our identities around the newsroom that we happen to be in at this moment or the beach that we happen to be on. But these things come and go. And I think it's harmful for a person's career to build one's identity solely around a job or an organization, whatever it may be, because these things change. And, you know, take that away and kind of what are you left with? Always have that plan B.

Jonathan Small: I think it's so wise. And you actually wrote a really great article about this topic about you aren't what your job is. What was it, the idea, the verb, it's not what you do. Explain that a little. Because I thought that was so enlightened, and especially in - I don't know, if you live in the coastal places in the world, the first question people ask you is, so what do you do? You know, it's so much about your identity, its so much about what you do for a living. That was a big thing - learning - that you shared. Can you talk about that a minute?

Tim Herrera: Yeah. That was a really important article for me, personally, as well. So the headline of that article was, what you do is not who you are. And the idea behind it was that we need to have an identity outside of the thing that we do to make money, to pay rent and buy groceries. And I think you're totally right that in certain regions and really in certain cities, what you do is who you are. I've lived in New York since college and it's when you meet someone, like you're totally right. Once you get out of the initial pleasantries, it's like, oh, so what do you do? Like what are you working on? This is very much me editorializing on this, but I think that's just so poisonous. Because that's not who I am. That's what I do so that I can pay rent. That's just one facet of my life. So for the article, it was the wake up call. Because I did fall into that trap of becoming so identified with what I was doing. Like, I was the Smarter Living guy. And I really leaned into that.

Jonathan Small: And it's cool, right? So you tell people that on a plane or at a party and they're like, oh, you work for the New York Times, the Smarter Living? I read that. You know, it's like, you can get very wrapped up in that, I can imagine.

Tim Herrera: And you do. I think it happens to so many journalists because there's this sense that - nobody thinks journalism is more important than journalists. And I think we just love identifying with what we do because we think it's a public good. And newsrooms have a genuinely good mission, but it is still just a job. So for me, in writing that article, really was this wake up call because that was my identity. All my friends were journalists, everybody I knew in my life knew me as like the Smarter Living guy. I dedicated so much time, effort, tears, blood and sweat into that job. At the end of the day, it's like, that's just a job. And so one of the things in that article that I thought was most important was I had interviewed - I forget who it was.

He's a psychology professor at UT. And one of the things that he said - he told me this years ago, because I had interviewed him for a separate article and he told me this years ago and it always stuck with me - we should think of jobs more as verbs rather than nouns. And so for me, for example, I would say, I do journalism rather than I'm a journalist. It feels like kind of a silly arbitrary word swap. And like obviously, it's used as an example. Because, you know, a surgeon is never going to walk up to someone at a party and say, I cut people open. But really, it's more of a mindset shift where we're thinking about where we are from nine to five is just the thing - it's perfectly fine to love what you do and enjoy it and love your coworkers and enjoy hanging out with them and everything.

But at the end of the day, it's what you do so that you can pay rent. I think it's so much healthier to think of it that way. Because there was another part of that article where the same guy had said that - oh my, I'm totally going to butcher it - but essentially, life is a roller coaster with ups and downs. And if all of your life is devoted to work, if that part of your life is at a dip, then your entire life is at a dip. But if that's just one thing, there are still other parts of your life that could be going well. I think this is such an important philosophy. And truly, I think the pandemic has kind of forced a lot of us to think that way. You read one thousand articles every week about the great resignation. And I think that is a huge component of that. That we're realizing that we can't build our lives around our work identity. And I think it's wonderful to see it. I'm so happy that collectively we are realizing that.

Jonathan Small: It reminds me of, a shrink once said to me, what do you want your epitaph to read? Like what do you - so you don't want the top of your thing. You know, he was a successful podcaster and wrote for magazines, like that's not - you want people that say, he was a great father and a wonderful friend and made people laugh. Like, those are the things you want to be identified with. Like, what really are your values? I think that's so important.

Tim Herrera: Exactly. Right, right.

Jonathan Small: Alright. So let's talk about Freelancing with Tim. It's really a great resource. I strongly recommend it to my listeners. It's interesting because it kind of reminded me - when I first started reading, I was like, people are still really interested in this information. Because way back in the day, I was involved with this organization, I think it still exists, called Media Bistro. Do you remember Media Bistro?

Tim Herrera: I do. Yeah.

Jonathan Small: It's actually how I know Taffy Brodesser-Akner who was a former colleague of yours at the New York Times. She was technically my boss there. But I used to teach for them. I used to do a lot of what you're doing now, like teach how to pitch and how to do this. And that was at a time when magazines were actually - you could make a living as a freelance writer for magazines when they actually existed in a print form and newspapers, et cetera. And I wondered, is this still a viable career for people? Like, can you still make a living being a freelance writer? Because now that you know - I am guilty of assigning people on assignments, having only being able to pay them like 25 cents a word. I mean, it's crazy. I used to make $3 a word in the nineties, you know? So it's definitely depreciated in value. So talk to me about that. Like, why is this relevant now?

Tim Herrera: I just always love hearing from folks who were writing in the nineties and hearing about 3, 4, $5 word assignments

Jonathan Small: Yeah. The golden age.

Tim Herrera: It's just insane. It's insane. I think being a freelancer right now is great, but also really, really tough. You know, I think it's great because there are more places than ever to write for. There are more forms to be doing as a freelance journalist. And I think there's just a lot of - the barrier to entry, I think, has gotten increasingly lower, which I think is great. But at the same time, rates are so depressed, even more so by the pandemic. I think one of the central issues, what I think is so silly, is that basic information about being a freelancer is just so hard to come by. When I started Freelancing with Tim, most of the initial panels and most of the initial content that I was putting out was just around pitching. I think I'm somewhat of an expert on this.

Jonathan Small: Yeah you are. We'll talk about it.

Tim Herrera: Any editor at the times gets dozens of pitches a day. You know, there were weeks when I would put out calls for pitches. I would get 6, 700 pitches in a week. So I've seen many, many pitches. So initially, the panels and the newsletter were just about how to write better pitches. And as I was kind of doing my own research, there's not really a lot of solid, reliable information around that. You know, one of the things that I still cite is this article I wrote for Harvard's Neman lab in 2018 about writing better pitches. And that was kind of the germ of the freelancing with Tim wider cinematic universe. I just wanted to provide a resource that was free, that came from someone reliable, someone who actually knows what they're talking about, and just put out all this information that for a long time is sometimes intentionally kind of kept secret and very opaque. The most popular newsletter that I've written - and it was actually one of the first projects that I had done with Freelancing with Tim. This is way back in June or July of 2020 - was I and my assistant at the time spent hours and hours rounding up pitching guides for every publication we could find and essentially just built a database. And literally the headline for that newsletter is like, here's a shit ton of pitching guides, like, take a look. And so it's literally just this alphabetizing [32:52 Inaudible]

Jonathan Small: It's awesome. It's free.

Tim Herrera: And that's it. Like, it's the most simple thing. Like, there's hardly any -

Jonathan Small: It's like, who's the editor to pitch what they're looking for? That's great.

Tim Herrera: Exactly. 150,000 people have read that. And it's just like the simplest thing, but it didn't exist before. And so that's the kind of core idea around all this. Taking this information that's kind of just sitting out there just beyond our view and saying like, hey, here it is, look, here, go, read this. This is what you need. That's really like the mission that's driving all of this.

Jonathan Small: Yeah. And let's talk about - you mentioned you already had this big following. Can we talk about the different content offerings you do and sort of your different revenue streams for those? You don't have to talk about actually your revenue details. What is the content, first of all, that you're putting out into the world? You've got this Substack newsletter, which has a subscription, which I just subscribed to. Really recommend. It's called freelancing with Tim. That's one thing. And tell me a little bit more about what freelancing with Tim is?

Tim Herrera: Up until this summer, everything was free, very much by design. I've always kind of really taken issue with places and folks who kind of offer this information but charge really high rates for it. And so I really wanted to put everything out there for free. So up until I didn't have a job, it was all free. And so now I've been spending a lot of time really strategizing and thinking through revenue streams. So first, I turned on paid subscriptions for the Substack. That was the first initial foray into monetizing this. You can subscribe to freelancingwithtim.substack.com. So that was the first thing. And so I offer a couple of different tiers that offer added benefits. So there's still the free newsletter which comes out every Tuesday or Wednesday and then there's additional paid newsletter only for paid subscribers. And then there's subscriber only events and a bunch of other stuff like that.

So the Substack is one. That's kind of the core. On top of that, I do free zoom panels around a given topic. And so this is what I was saying when I started was just around pitching. And so I would come on, invite a couple of other editors at publications and we would just spend an hour and a half answering reader, viewer questions about the pitching process, what makes a good pitch? What should I avoid? What do editors want to see? All that stuff. And they were super, super successful. Before I even really started strategizing trying to build it out, I would have hundreds of people on these zoom calls. That was kind of an indication to me that like, maybe there's something here and I should really start building it out. And so that summer I hired an assistant and we started thinking through like, what else can we do around this?

Like, we know this format and structure works, how do we build? And so I started offering free zoom panels on stuff like travel writing and writing personal essays and writing long form features and doing culture criticism. Basically, any type of writing that a freelancer could potentially do, we had a zoom panel about it with industry experts and people who've been doing it for years. One of the other offerings with the newsletter, the free zoom panels and something that I've started doing since this became my primary job, is I'm offering paid workshops. And these are limited space and they go really, really into very explicit detail around just one thing. So for example, next week, I'm doing one of the most popular workshops that I do. It's just 90 minutes around how to structure a long form narrative feature.

That's it, that's all we talk about. I have an hour of curriculum, we do a half hour of questions. And the idea is that by the end of that, everybody watching walks away with the knowledge of how to organize and structure a 4,000 word piece. That's been something that I've been really leaning into. And I've been very grateful that there's been a desire for that. Paid workshops. I've also gotten into doing one-on-one coaching with writers on everything from pitch reviews, to story ideation and development, to writing critiques, editing critiques, stuff like that. So I'm really leaning into that as well. And then hopefully, fingers crossed, maybe early next year, I'm going to be - you know, this is such a question mark - but maybe getting into doing events. There are a couple event spaces that I've been in contact with for the last couple months who are interested in partnering and doing stuff, but it's just like, anything IRL is just so difficult logistically and also like, are people even going to show up?

Jonathan Small: Right. It's tricky to know.

Tim Herrera: Once there's a little more clarity on that, hopefully we'll be doing actual IRL events.

Jonathan Small: Yeah. Real quick, just to go back to a question I asked, is it a legitimate line of work to be a freelance writer in 2021? You had one really great article you wrote where you talked to somebody who made, I think, like $27,000 a month freelancing. So that answers the question. But I don't know how that person did it and you kind of go into it a bit. But it sounds like the answer to my question might be, yes, you can still make a living as a freelance writer.

Tim Herrera: The answer is yes. I think the question of what a freelance writer does is evolving and shifting. And I think that's the more important question, its I think it's perfectly - you know, many, many people make a living freelancing, but extremely few people make a living doing freelancing only doing news and journalism writing. So the person that I interviewed for that newsletter, she had made $27,000 in September. And she did some news and journalistic writing, but mostly, it was doing copywriting, it was doing brand work, technical writing, writing that we don't traditionally think of as what a freelance journalist would do. But I think the way to make a successful freelance business is to diversify the type of writing you're doing. I've had conversation with folks who are a little uneasy with that idea, because again, we think of ourselves as journalists.

Like, I write the news. That's what I do, that's who I am. You know, I could probably count on one hand the number of journalists I know who make one hundred percent of their income just from news writing as a freelancer. Yes, you can be a freelancer, but diversify what you consider the type of work that you're interested in doing. And, you know, the truth is once you kind of open that Pandora's box - and I've seen this firsthand now that I'm doing freelance writing - news and journalistic writing is by orders of magnitude, the least lucrative writing you can do as a freelancer. I'm doing some work where I am making like 4 or $5 a word, but it's not news writing. Like, I'm doing gigs where I'm pulling in $90 an hour, but it's not news writing.

Jonathan Small: What is it? It's copy editing for brands -

Tim Herrera: One of them's been editing and one of them's copywriting. Yeah. And so I think just being okay with not solely doing journalism, I think, is the way to build a successful business, but also, it's the way to get paid. And like, that's why we were like, nobody's doing this because it's like a fun hobby, we're trying to get paid. And so the way to get paid as a freelancer is to branch out of just their traditional news and journalistic writing. The freelancers I know who make the most money, that's what they do. Once you kind of see the other side, it's almost like, why bother with these things where I'm making 20 cents a word when I could be making $2 a word.

Jonathan Small: If you will indulge us for a minute, I do want to talk about pitching because you are sort of the pitch master. And I don't talk a lot about pitching on my show. If you wouldn't mind divulging some of your secrets. I still want people to subscribe to your newsletter, so we'll talk about as much as we can that you're comfortable talking about. Let's just talk about - you talk about, there's basic sort of rules of pitching. We can narrow it down to even pitching the New York Times since you worked there for so many years, but it could just be, maybe these are basic rules for any place that you pitch. Every magazine and sort of publication or entity is going to have different rules. But I was very intrigued by this. It seems so obvious when you've done it, but for people who are maybe new to this game, your dos and don'ts, can you sort of go through some of those with us?

Tim Herrera: Yeah, absolutely. Two quick things before we dive in. First off, these very much are not secrets and I will sing this information from the rooftops.

Jonathan Small: Oh, good. Okay. Thank you. Yeah, no, you're very generous with your knowledge. But I think it's smart because what you've done is, it's like that freemium model where you started off, you gave it away for free. It's kind of what I do, to be honest with you. And then eventually you say, okay, well, if you want to really take a deep dive, please pay me this money.

Tim Herrera: And so the other super quick thing is, I always like to stress this when I do pitching panels and workshop, that there aren't rules. Every piece of pitching advice that anyone has ever given is a guideline and not a rule. That includes me and my newsletter. It's all just guidelines. There's a thousand ways to pitch every story. None of them is necessarily right or wrong, but some things can be a little more right, and a little less wrong. A quick button on that. I actually just did newsletter about the only four unbreakable rules of pitching. And these actually have nothing to do with the story itself, these are all structural issues. So first, never send a full draft unless you're pitching an opinion piece or a personal essay. Editors, generally, when we see a full draft, we think to ourselves, this person's done the story, it's take it or leave it.

And, you know, the editor's job is to kind of work with the writer and mold that story for the publication and their readership. So never send a full draft. It costs you money. The second rule is the structure of your subject line, which should always be freelance pitch: proposed headline for your story. Three, always include clips and a brief bio. Three or four recent ish clips is enough. They don't necessarily have to be really recent, but they should be the best work that you've done that you think represents who you are as a writer and what you're capable of. And last, just double checking all the small things. Which is like your typos and making sure you're addressing the right publication in your pitch and the right editor and making sure your links go where they should go and making sure the publication didn't just run something on this.

No single of those things is going to be a deciding factor. But if there's 18 tiny things that you got wrong, that's going to give the edit a pause. Okay. So those are the only rules. But a couple of general guidelines. Once start talking about length, I don't think there's any story in the world, whether it's a next day news story or a 4,000 word investigation that can't be pitched in under, say, 12 or 15 sentences. There are more reasons than that, than the editor just doesn't have time to read it long pitch. But the core and why I like to focus on that is when an editor gets a pitch, it's always clear whether the writer knows what their story is, or if they're trying to find that story in the pitch. And most of the times when we get a pitch like that, it's these 700, 800 word meandering stories and narratives where you can tell the writer is trying to find the story in the pitch it's self.

And I think forcing yourself to really be incredibly concise and thoughtful with the words that you're using in the pitch is kind of a check on yourself to make sure that you actually know what you're pitching. You know, one of the most common reasons that pitches fall flat is the writer doesn't know what their story is. And this is a very fixable problem, but it's a really common one too. And there are things that you can do to check against that. But you have to know what your story is. And editors, we see enough pitches that we have a pretty good sense of when the writer is trying to find the story in the pitch.

Jonathan Small: I think that's so important when you mentioned that the headline in the - a lot of times we editors think in terms of headline. How am I going to package this story? Like, what is the headline? You know, back in the day, it was what's the cover line of this story? Because we used to think a lot about cover lines when I worked at magazines. I think that helped you focus the idea of what your story is about in a way

Tim Herrera: That's exactly right. And that's the reason that I always like to - so there are three checks against knowing what your story is. The length is one. And you're exactly right that the headline forces you to think through, do I actually know what I'm talking about here? Do I know what the story is? When you find yourself killing yourself for like 15 minutes, just struggling to write a headline or a subject line, that's generally a pretty good sense that maybe I don't actually know what the story is that I'm pitching. So that's the second check. The third is I always like to encourage people to include at least a skeleton of a nut graph. Obviously, that's going to change from pitch to publication because you haven't done the reporting yet.

But when you force yourself to write a nut graph for your story, you don't have an option but to know what your story is. Because you can't write a nut graph if you don't know what you're talking about or what you're writing about and what's important about it. It makes for a compelling pitch, but it also ensures that you actually know what your story is. And, you know, again, there are many ways the pitches fall flat, but not knowing what the story is in my experience and experience of editors that I've spoken with, that's generally the most common and it's so fixable. And a lot of times it just takes an extra day of thinking through your story.

Jonathan Small: How do you, quickly, define a nut graph? Just for those who might not understand those journalistic terms. A nut graph is like the summary of what you write of your story, the kind of roadmap of what your story is going to be about,

Tim Herrera: Exactly. The traditional, who, what, when, where and why, all that. The encapsulation of the story, and what's important about it.

Jonathan Small: These are great things. I mean, some of the things that you don't want to do, like you mentioned not sending a full manuscript, that's definitely a red flag. You also said - I remember reading - don't send a laundry list of ideas. Because a lot of times when I get pitches, it's like, here are five ideas I propose. And it's like making a lot of work for the editor, right? Why is that not a good thing to do?

Tim Herrera: This is something that I love talking with other editors about, because whenever this question comes up, it is literally - I've done dozens of panels just on pitching and it is such a 50, 50 exact split among editors who like to see a single pitch in an email or batch pitches. And a batch pitch is just a pitch email that contains more than one idea. So I actually am of the thinking that I like to see batch pitches. You know, it kind of feels like you're going shopping. Like, oh, I'll take this one, I'll leave that one on the stand. But the caveat to that is if a person wants to write a batch pitch, devote the same amount of time and energy to each pitch that you would if you were pitching it on its own.

Because I think the trap that we fall into when we start writing batch pitches is we think, oh, there's a couple of ideas, I can just kind of like just throw it in a little bit. It's like the quantity versus quality issue. So, you know, just be as thoughtful with each pitch as you can. But on the other hand, 50% of editors never want to see a batch pitch, only want to see one pitch per email. Which is perfectly fine. You know, the major caveat here - and again, there are only guidelines, no rules. One maybe half rule, strong guideline is in a first pitch email, a cold pitch to an editor you've never worked with, in that instance, I generally would not advise sending a batch pitch. I would just stick with one idea, the best idea that you have for that editor at that publication.

And that's a super quick little tangent that I just talked myself into. It's, generally, you want to pitch the editor and not the publication. And so what I mean by that is know the editors, what they're about, what kind of stories they like, what their vibe is, what topics they're interested in, what their style of editing and writing may be. Because, you know, every editor at every publication has different things they look for, different ways of working, they want to see different things in stories. So just do a little research, like make sure you know who your editor is and what they're all about. So the best pitch that I've ever gotten was ostensibly like kind of a very silly idea. It was a pitch about why people should buy a home printer. Which feels kind of silly and it wasn't really up my alley. But it's the best pitch that I've ever gotten.

So this came from a writer that I had never worked with before, but that I kind of generally knew from the internet. We had exchanged a couple of tweets here and there over the years. But we knew enough about each other that she knew what type of editor I was and what my vibe was. And so the subject line for this pitch was love yourself and just buy a fucking printer. And I think that is so genius, because she knew that I would respond positively to that. She knew that that silly tone is what I love in a story. And she knew that I wouldn't be offended by someone putting a swear in a subject line. But she knew who I was. And the way that she had written the pitch was just so specifically tailored for me and my interests and my vibe and my tone and the way that I like to work with people, that it was just that she could never send that pitch anywhere else. Not only because of the vulgarity, but because that was a pitch for Tim Herrera, not a pitch for the New York Times or for Smarter Living. And I think that's just so, so important.

Jonathan Small: Yeah. I mean, people will tend to - they'll pitch things that would never appear in the publication they're pitching or would never appear in the column or the section that the editor is - it's amazing. You have to do your research and before you pitch, you have to at least read five stories that this editor, I think, has edited or written to get a sense of the tone. It's always surprising to me. I mean, I remember way back when I worked at Max and I've told this story before, we got, like, pitches for poetry. Like, in what universe to ever do poetry?

Tim Herrera: Maybe you should have taken that.

Jonathan Small: Maybe we should have done poetry. The whole world would've changed. Yeah. Lead to all the douchebags that came out of the world of Maxum. But no, I mean, seriously, it's incredible to me and it feels very lazy because I feel like if you won't take the time to do a little research into the kind of stories, then why would I want to work with you as a writer? It's just very indicative of the kind of person that you might be professionally. And we're not dumb. Like, we get it. You're much nicer about freelancers than me. Maybe it's because I've been a freelancer. You're like super nice about them. Maybe it's because I've been a freelancer and I get mad when I - I've been on both sides like you, I've been on both sides. I've been a freelancer, but I've also been an editor. And sometimes I can't believe the kind of pitches I get as an editor, having been a freelancer and know what they're expecting.

Tim Herrera: Right. And it's so funny being on the other side of it. I know what makes a good pitch, but I still feel anxiety sending out pitches. Like I know it's a good pitch, but, like, ah, are they going to take it? What if they don't like me?

Jonathan Small: They're going to hate it. I know. And one of the mistakes, another mistake that people make is that they will pitch something that has already appeared in the section. And not only has it already appeared, but within the last two months. So again, research, right?

Tim Herrera: That's the - like, I've mellowed out a lot. But that was one of the things that used to drive me up the wall. When you're doing the pre-research before the pitch, that's like the literal least you can do. If you do one single thing, check the archives.

Jonathan Small: Just put in Google, New York Times.

Tim Herrera: That's it. Like, do that and you've satisfied such a huge check mark. So when people pitch something that I ran two weeks ago, I'm like, come on man. Like, come on. This is literally the least you can do.

Jonathan Small: You talk, you had another thing about why do pitches get rejected. And you're very kind there again. And it's true that I think when you get rejected - if you hear back at all, because a lot of people don't even hear back at all. But if you actually get like we're going to pass on this type of email or a TBNT. Thanks, but no thanks. I used to be in charge of mailing those out back in the day and when we still did snow mail. You come up with things which are illegitimate of reasons that people do get rejected and it's not always personal. Probably 95% of the time it really isn't personal. It's never really personal, but it's not about your writing so much as it is about situations that are sort of out of your control, right? Like, budget?

Tim Herrera: This is another thing that I think - there's this bucket of ideas that I always like to talk about of things that freelancers really stress about that editors don't even think about. And I think a lot of this stuff comes into rejections. And so the top line is, I interviewed a freelance writer named Racks King last year. And we talked about rejection and she said the smartest thing that I've ever heard about this. And she said that in terms of pitching, rejection is not feedback. For me, that's such a huge mind shift. Because it feels terrible when your idea's rejected. And in the moment, it kind of draws your worth into question as a writer. But reframing that as like, no, this says nothing about the story. It may not just be the right time or maybe there's not the budget.

And so this newsletter that I had written about reasons that editors reject a pitch, like you said, 95% of the time, it really doesn't have anything to do with the story itself, but it has to do with operations and logistics. And so we were talking about things like, is the budget there? Is there even money to commission a story right now? Did we just run something on this? You know, is this the right idea for the right editor? Is this idea outside of that editor's purview or area of expertise. Maybe they just never even opened your email. We personalize rejection so, so much, but like, the truth is there are a thousand reasons that editors reject story ideas and pitches and four of them have to do with the actual story.

Jonathan Small: Right. And we've talked about that. We've talked about what you screw up, maybe you pitched the wrong editor or you sent a full manuscript, you know? There are things that we've already talked about. But most of the time it has to do with just like, there's no way you could know that there was a similar idea in the works. But I often hear sayings like, they stole my idea and I'm like, no. Again, that doesn't happen.

Tim Herrera: It doesn't. That's another thing that freelancers stress about so much. And I've had this happen to me on both sides. Like, I'm sure it has happened, but just on the scale that freelancers think it happens, it does not.

Jonathan Small: Yeah. The panic of that. Like, how do I know that my idea is safe? I don't know why that question has always been, I don't know. That is like an urban legend.

Tim Herrera: I so agree, but I get asked about it so much.

Jonathan Small: Me too. So let's put this to rest right here. Ideas generally do not get stolen. It's not like editors sit around and be like, this is a good idea. We should assign it to this writer and not this - it's like, first of all, ideas are out there. Especially if it's a current kind of a topical idea, chances are somebody else has had a similar idea. Unless it's really out there, something like the printer idea you had, which sounds to me like a very unique idea that would be very unusual for another person to have, but you never know.

Tim Herrera: I don't want to keep talking about this, but it's just so funny to think, like, if that really ever were to happen, the editor who did that would be fired. Like, that's not something you do as an editor, stealing ideas from freelancers. That is just such a breach. And to do that, it's so outside of - I don't know. It's just crazy to me that so many people think this happens. It just doesn't happen.

Jonathan Small: Do you think it ever is wise to write an - if an editor just doesn't tell you why they rejected your story, which they probably won't, do you like it when writers say, like, I'm just trying to improve my pitching skills. Can you tell me what it was about my pitch you didn't like? Or what can I pitch that you would like more? Do you kind of find that to be a bit tedious to get that kind of an email? Or do you think it's useful to send that email or to receive that email?

Tim Herrera: No, I love to get those emails. And I generally encourage folks to write them if they want feedback on that particular pitch. You know, the reason editors don't reply is if they replied to every pitch they got, that's all they would do in their day. For me, I generally didn't reply unless I was interested. But anytime someone who got a no from me or didn't get a response followed up to say, hey, just wondering why this wasn't the right story or wasn't a good pitch or whatever it may be, I loved writing that. It's minimal effort for the editor, because they could probably dash that email off in six minutes. But for the writer, that is such huge information and such valuable information to have. Editors that I know and have talked about this with are generally fine doing that. Because again, it's such a low lift for the editor, but it's a huge, huge benefit for the writer. And so I always tell people, if you don't hear back or if you've got to know, just send a very polite, very casual follow up that just says, hey, you know, sorry this idea didn't work out, just wondering if I could get a little info about why this didn't work for you. That's it. It's super simple and super easy.

Jonathan Small: What do you think of the question of like, well, can you tell me what kind of stories you're looking for? That seems like you're asking the editor to do the freelancer's work. Or unless you specifically have like, God, we really do need a story on this particular topic, and if you happen to have one. But I don't know, what's your feeling on that?

Tim Herrera: That's a little bit more of an ask. But to me, I always tell freelancers that the way to kind of do that is, I'm a really big fan of writers just introducing themselves to editors. This happens to me all the time. I do this as a writer. Just a super casual Twitter DM to say like, hey, I'm Tim, I'm a freelance writer. I just wanted to introduce myself and ask if you're commissioning right now. And if so, what are you looking for? You know, that, I think, taking it out of an email makes a little less of a lift and a little bit more casual. And I think, generally, editors are going to be a little bit more amenable to responding to it in that format. Feels a lot less intense.

Jonathan Small: Alright. Writers that you want to continue working with, aside from just being their good writers and they have good ideas, talk to me a little bit about - because we've all kind of worked with difficult writers, and I think there's a certain type of writer out there who does not like being edited, who is very attached to what they've written and kind of pushes back. Talk to me about the kind of writers that you like to work with.

Tim Herrera: I wrote a newsletter about this. And the headline was like, how to get on an editor's regulars list or whatever. One of the things I wrote about this was the best freelancers are freelancers - aside from the obvious things like filing on time and all that stuff - but writers who file copy without surprises. Like, when I get a story that's exactly what we talked about and there's nothing new in here, it's the structure that we talked about, it's the source list that we discussed, maybe a new source here or there, or a new ID here or there, but generally, I'm not surprised of anything that's in there. Those are the writers who I love working with. Because the editing process is so much easier and it's so much smoother on both sides. Like, if you file a story that is exactly what you and your editor had talked about, prefect.

Everybody wins in that scenario, because it saves you time. So it's saving you money. And it saves the editor time and effort and just moves the process along. And that's not to say that things don't change with a story. But the best freelancers are the ones who know that when the story that you had talked about with your editor or the source list or whatever it may be, doesn't actually work, now that you've done the reporting, what you thought the story was, it's actually this. Like, that's not really a problem so long as you email your editor and say like, hey, can we hop on the phone for 10 minutes? Just want to talk about this and say, you know, I've been doing some reporting on this and what we thought the issue was here is actually not the issue, but this is what it is.

I've had that conversation so many times. And the best writers are the writers who know to have that conversation right when things change, not when you're filing a draft to say like, hey, I know we had talked about this story was X, but I'm going to file a story around Y because when I did the reporting, this is what it actually was. Like, a changing story is not a problem and a lot of times is a good thing, because the story should just follow the reporting rather than vice versa. So it's not an issue. It only becomes an issue when you file a draft that is full of surprises. To me, those are the best writers to work with.

Jonathan Small: No surprises. What about when writers push back on your edits a bit? Like, what's your feeling of that?

Tim Herrera: I love that.

Jonathan Small: Really?

Tim Herrera: I do.

Jonathan Small: You should be my editor.

Tim Herrera: I generally try to have kind of a light touch. And I try to do everything I can to preserve the tone and style and ticks of the writer and to let them shine through as much as possible. And so, you know, I do all my edits in a Google doc and suggestions and I kind of try to train my writers to push back on something that they don't see as a net positive. And the way that I like to have these conversations is I tell writers, an editor should be able to justify every single change they made to your story. Even if it's like a comma or they made a semicolon, an M dash, whatever it is. Like, if you said to the editor, why did you do that? They should have a concrete justification for making that change.

And if they don't, maybe push back if you don't like it. It's not worth raising hell over a couple of different commas and M dashes. Being free to push back makes you comfortable to push back when it matters. If the editor makes a change that you really think harms the story and gets away from your vision for it or your voice or whatever it is, that is the time when maybe it's worth raising a little hell. But if you feel comfortable just knowing that you can push back, it makes that conversation a lot less daunting. And that's the other thing. I feel like there are a lot of freelancers who don't really know that you can push back. And it is intimidating. And like, I've had these conversations that if you're pitching The New Yorker or something or the times, you kind of take on faith that they're going to make changes that only improve your story, but that is not always the case. Like, you can push back on edits. And I think that freelancers can sometimes feel uncomfortable doing that. But like, for me, I like it. I like to get challenged a little bit. And I think, you know, when I've made a change that I actually can't justify, I think that makes me a better editor. So it's kind of like reverse psychology training me to be a better editor also. I like this conversation. I think it's good for everybody involved.

Jonathan Small: Alright. So to conclude here, what's the kind of one bit of advice that you've received or you've written in your column, in smarter living, but also now with freelancing with Tim, that has just stuck with you, that has kind of guided you through your journey here. Because you've been through a lot in the last few years, right? Big transition in your life.

Tim Herrera: I'll say two things. First, you know, to call back to what we were talking about earlier, disentangling your professional life from your personal life, that to me has been an existential change in my self-perception. And I think it's so difficult for journalists. Because again, it's good that we think what we do is important because it is, but it's not your identity, it's still just a job. Journalism is not a calling, it's not a duty of a higher honor, like, it is a job that you get paid to do. And so for me, that was just such a profound shift in how I view myself and the way that I interact with the world. In such a positive way. It really changed who I am and the way that I view myself. So that's been such a crucial mental shift for me. And the other thing is just a bit of career advice that my mentor I was talking about earlier, the editor at the post and the times who hired me. Years ago, he said, when you advance, don't pull up the ladder behind you, throw down ropes.

And, you know, I think that is a lesson that I really have taken to heart. And that's really why I wanted to do freelancing with Tim in the first place. It was like, I had all this knowledge that was just kind of sitting in my stupid brain not helping anybody. And so I figured out a way to dispense that and throw it out into the world. Journalism can be a really cutthroat industry, but it doesn't need to be. And being a cutthroat industry is bad for everybody and it doesn't help anyone. And so I think any opportunity that you have to help someone out, especially if you're not getting anything from it, like, I always think those opportunities are worth it. Even totally cynically looking at it, the self-satisfaction you can get from, oh, I helped that person. It's such a benefit for everyone in the industry. It's a benefit for person doing it. And I think it's just like such a good way to live one's life by and a good way to navigate one's career by.

Jonathan Small: Well, I thank you for throwing down many ropes to us today. I feel like I want to grab onto a bunch of those. I'm sure everybody feels the same way. If people want - you've mentioned it before, but if people really want to follow you, there's a lot of different ways to kind of find out about you. So I'll give you this opportunity to kind of share some of those URLs and things.

Tim Herrera: Yeah, thank you. So if you want to subscribe to the newsletter, again, it's freelancingwithtim.subs.com. You can follow us on Instagram, just at freelancing with Tim. You can follow me on Twitter just @TimHerrera. H-E-R-R-E-R-A. And I think those are the main ways.

Jonathan Small: Yeah, those are big ones. Tim, I'm so excited about your new venture here and it's just really valuable and I kind of wish I had thought of the idea first, but I'm glad you're there. I'm just kidding. But thanks Tim for everything. And I hope to have you come back on the show. You got any books in the works or anything?

Tim Herrera: Nothing I can talk about at the moment. But no, thank you so much. This is such a great conversation. Thank you so much for having me on. This is just wonderful to chat with you.