Boss Ladies
2/15/19 - Self employment realtalk: how we went from office workers to freelance to boss ladies. We bust myths about staff jobs and incorporating your own business. Is it hard? Yes. Is it for everyone? No. Could you stand to make a lot of money and forge your own path? Yes! We discuss our career trajectories, how much to charge, who to ask for help, and how much you should have in savings.
Transcript below.
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CREDITS
Producer: Gina Delvac
Hosts: Aminatou Sow & Ann Friedman
Theme song: Call Your Girlfriend by Robyn
Composer: Carolyn Pennypacker Riggs.
Associate Producer: Destry Maria Sibley
Visual Creative Director: Kenesha Sneed
Merch Director: Caroline Knowles
Editorial Assistant: Laura Bertocci
Ad sales: Midroll
TRANSCRIPT: BOSS LADIES
[Ads]
(0:58)
Aminatou: Welcome to Call Your Girlfriend.
Ann: A podcast for long-distance besties everywhere.
Aminatou: I'm Aminatou Sow, the CEO of Deliberate and Not Afraid, LLC and a co-owner of Call Your Girlfriend, LLC.
Ann: I'm Ann Friedman, CEO, president, and pretty much everything of Ladyswagger, Inc. and also a co-owner of Call Your Girlfriend, LLC.
Aminatou: Hey girl!
Ann: [Laughs] Are you ready to talk about self-employment?
Aminatou: I'm ready. I'm ready. My tax stuff is staring me in the eye so I'm a little . . . I'm not going to lie to you, the anxiety is jumping out, but also, you know, the pleasure is jumping out so it's cool.
Ann: It's admin season. Like it cannot be denied that it's admin season.
[Theme Song]
(2:02)
Ann: Okay, so we are both self-employed humans. We were having a conversation some months ago about the ways in which the skills we have had to develop in working for ourselves and on our own do and don't translate to staff employment and also about some of the myths surrounding self-employment that I think are perpetuated by a lot of self-labeled creative class digital people who are like this is a thing that everyone should aspire to. So we kind of want to talk about this whole cocktail of stuff.
Aminatou: Right. I mean it probably helps to talk about how we ended up being self-employed right?
Ann: I agree. How did you end up self-employed?
Aminatou: Whew, child, my serotonin went to war. My dopamine went to war. Nobody is back yet. [Laughter]
Ann: And that's how you ended up self-employed?
Aminatou: That's how I ended up self-employed. All my life I had to fight for myself. I started off in office jobs because that's the immigrant thing that you're supposed to do. I worked at a bunch of different places like at a think tank, at a marketing PR place, at a digital PR place, and then my last real job was at a tech company, the artist formally known as Google. You might know her as Alphabet. [Laughter] You know, even in-between the different jobs that I'd had I definitely had like a tiny period where I had dipped my foot into trying to do freelance and it was too early. It was like whoa, you've got too much dip on your chip Amina. Like it was too early and it didn't work out and I went back full-time. I think I literally lasted like 60 days then I went back into for real work, like went back into working in an office.
(3:48)
And I think what I did then was try to do a little bit of comms consulting and then some writing which LOLOLOL that did not pay the bills for me. The real reason that I ended up self-employed honestly is because I was reaching maximum burnout at work and also for me that was really colliding into a lot of health issues that I didn't know that I had. It's like I was working too much. I hated living in San Francisco. Like the work itself was not overwhelming but I just threw myself into work because I hated everything else, you know? And at the same time it turned out that I had the early beginnings of cancer which I didn't know about but it just meant that I was tired all the time. I had all this -- just like my body was failing me. And so when I looked in the mirror and it was like well, you can keep doing this thing or I can take some time out to actually figure out what is wrong with me. And at the time that's . . .
Ann: Wait, you mean the American workplace is not a good place to heal and figure out what's going on with your body? Weird.
Aminatou: No, but you know, honestly Ann it's like in hindsight that I recognize that those are the choices I made. At the time I was just like I am fully just fed up. I'm fed up of, you know, I'm fed up of living here with the robot Americans. Like I'm just done. You know, and now with a lot of looking back it's like oh, no, the reasons I was miserable are actually 100% because I had cancer and I didn't know about it. [Laughs] And so thinking about just the pressure I felt of never taking time off to go to the doctor or how annoyed I was at the fact that my body couldn't keep up with where my brain was or the productivity level I had, I'm only recognizing now that this was part of the issue. At the time I was just like I am fed up.
But also a thing that I was really lucky to do is I got to quit a big, well-paying tech job and then essentially freelance did that exact same job. And so in the beginning really what it meant was like oh, I can do this at home without my pants on? No bra. You know, and nobody hovering kind of over me. I wasn't part of an institutional mandate. I had become a contractor.
(5:58)
For me emotionally that remove was huge. It was huge to feel like okay, I'm not part of a team in the way that you are part of a team if you have to go into an office every day. And that removed like a ton of pressure for me. In the meantime we had also formed CYG LLC.
Ann: Oh wow, did that happen right around the time that you . . . I guess that's true. We had started doing -- when we started doing the podcast you were still staff employed. Yeah.
Aminatou: Yeah. We started doing the podcast before. Yeah. I was still staff employed when we were doing the podcast and so through doing some of the podcast stuff it just gave me a lot of knowledge and also honestly a confidence boost to be like oh, we're not going to IRS jail. We can do this. And so my past self-employment was very circuitous and honestly, yeah, at the beginning I did mostly . . . like my entire consultancy was built on doing tech marketing and today that is 0% of my work.
Ann: Okay, so when was your . . . the last day of work you put in as a staff member full-time in an office?
Aminatou: Summer 2015.
Ann: Dang.
Aminatou: Four years. That seems truly wild. I could not have predicted that.
Ann: Well my last day of full-time employment in an office was May 31st 2012.
Aminatou: Wow.
Ann: I know. I know. About to be going on my eighth year. I became self-employed because I got fired. [Laughs] You know, the tale that everyone always loves to think about when they think about how they will start their much-anticipated self-employment period. It for me did not start as a plan. It did not start as an oh, this is what I'm going to do and I'm definitely going to be self-employed. I had been working at a magazine and I had been an editor for a long time, like six years or something like that, a magazine editor. And I really just didn't want to move to New York which is where all the magazine editing jobs were. And so I was like okay, I'm going to stay in Los Angeles and see about this writing thing, like maybe see if I can make some money in the interim while I figure out how to reconcile the fact that I want an editing job but editing jobs do not exist in this city that I really love living in.
(8:10)
And so there was a period of time, a couple of years at least, where when I would meet someone new and they would ask what I did I would be like "I used to be an editor. I'm kind of writing now. I don't know, I'm a writer. I'm a journalist sort of." I didn't have a clear . . .
Aminatou: You didn't have a pitch to them?
Ann: I know, I didn't have a one sentence description of what I did for a living that was not due to the fact that I wasn't working because save for like a maybe two-week period of just getting stoned in my underwear and not working after being fired I was like okay, got to pay the bills and started accepting writing assignments.
And so at the time most people were asking me that I could've said yes, I'm a self-employed writer. It took me a shockingly long amount of time to do that. And then it took me also about three years before I incorporated myself. I mentioned that distinction because I think that it marked a real turning point for me in how I thought about self-employment, so those first three years from like the middle of 2012 to probably the middle of 2015 or maybe the end of 2014 I was 100% a freelancer. You know, I took assignments from magazines and from digital publications. I worked really, really hard for not a lot of money per word which means I had to write a lot which means I spent a lot of hours hunched over my laptop. And I didn't really have the structural supports of a business.
And yes, I mean that in the sense of health insurance and all the things you think about with a staff job but I also mean in things like I did not have a business bank account. I didn't really have a sense of myself as like this is a business. I was still like I just work for other people. And I think for me deciding to incorporate, deciding to start making money off of this email newsletter that I send and selling ads in it, all of that stuff happened in 2015 which again is right around the time I think we incorporated Call Your Girlfriend as well. And all of that marks this shift where I'm like oh, from that point on I do feel I'm really self-employed. I'm not exclusively working for other people on a contract basis. A large portion of the work I do is for myself or for myself and my collaborators in like the case of Call Your Girlfriend.
(10:25)
So that's how I ended up self-employed. That is how I talk about my situation now and why I think it's important to distinguish like you and I as people who are incorporated business ladies who have a diversified income stream from people who are in what I would say is a more precarious position of freelancing on a 1099 basis for a variety of places. So I don't know, I think these are all nerdy but important distinctions when you say self-employment.
Aminatou: You also had that period when you were in Austin where you were freelancing.
Ann: Much like you, yes.
Aminatou: you dipped your toe in then dipped back out, so we had some sort of idea about what that looked like.
Ann: Oh my god, completely. At the end of 2010 I was like I don't want to live in DC anymore. I don't want to put up with these people who have decided not to promote me. I am striking out on my own, kind of like you post-tech job in the sense of I think I had a small contract to continue doing work for the magazine that had employed me as an editor. But I lasted two months max as a self-employed freelancer in that phase. And I think there are two big differences between that period and between my post-being fired period of being self-employed. And that is 1) I had a little bit more experience. Like in 2012 I had had a job previously where I had to oversee a budget and I had to think about business things in a way that I hadn't really had to before my first freelance attempt. That made a big difference.
(12:00)
I mean I was also a little bit more motivated by circumstance. I was like I don't want to leave this life I've setup for myself in Los Angeles so I'm going to find a way to make it work. I was like kind of deciding to come towards something as opposed to deciding to leave something and I think those two distinctions of experience and then this sense of okay, I'm actually doubling down on the things I do want rather than saying no to the things I don't want made all the difference for me in what took.
Aminatou: Right. We knew what the turmoil of not being tied to an institution looked like because I think that while a lot of people talk about the freedom of it the first time that I at least tried to like freelance or work for myself or whatever the instability of it all was terrifying to me. I think the first time that I had done that I had saved up like the proverbial you need three months of -- you know, a three month cushion of rent and bills and whatever. That did not seem like nearly enough money. Even the payment cycles that we're on, like some of the places I billed to are on a 90-day payment. [Laughs]
Ann: 90 days? Oh my god.
Aminatou: Oh yeah, there are a couple people that I work for that are on a 90-day payment cycle. But, you know, just thinking really about the instability of it all and how I personally was just not setup for that yet. I did not know how to live off a couple paychecks a year. I didn't know -- and forget the money part, like the actual how I'm spending money. What I really wasn't setup for was to find work. You know? And the kind of work that I like to do and the kind of work that would be fulfilling and the kind of work that was . . . you know, like contracts I would be okay living with essentially, like that just took a while.
(13:40)
And I think that, you know, while it is a huge privilege to say that I had saved up like three months -- like on the first stint that I had saved up three months of rent, my financial situation is also that I support my family. So I don't even know where I found the time to . . . like it took me forever to save up three months of rent. Like truly forever, like years.
Ann: Absolutely.
Aminatou: And then when I think about the actual big leap that I did after Google it was a little bit easier financially because I was sitting on a stack of cash, you know? Where it was like well, this should probably go towards buying a house or it should go towards something that is not blowing up your entire career in doing that. [Laughs] But when you work in tech and you make a lot of money and, you know, they give you stock or whatever there's all this money that you can play around with.
And so I remember talking to somebody about financial advice back then and them just telling me like "Hmm, that's not a great idea to use this money to live on. You should put it in a savings account or you should put it in a . . . that's a down payment for a house." Like all these other things. I was like no, this is the down payment for me taking a risk for myself and I'm really glad that I did that but it was terrifying but it was not nearly as terrifying as it was the first time around.
Ann: I mean let me tell you I was not leaving -- when I got fired I was not leaving sitting on a pile of cash. In fact they wanted me to sign an NDA in order to get a severance and I refused.
Aminatou: I remember that. That's my girl.
Ann: Yeah! But it also means I got no severance. Like they were only offering two weeks anyway but I had -- you know, it was basically pushed straight out of a nest, and I hit the ground hard. Actually in the metaphor of the ground I went beneath the ground because I was in a significant amount of credit card debt. I ran through the small savings that I had. It was honestly the sort of thing where I hate all these buzzwords of self-employment is risk or whatever.
Aminatou: It is though!
Ann: Well no, I mean it is but I think that that actually downplays the fact that the amount of risk you can take is completely related to the amount of privilege that you have. And the fact that I was able to bounce back at all, I really do count . . . I mean yes, hard work. Like obvi, yes, I will always credit myself for being a hard worker. But luck and privilege, big parts of it.
(15:55)
Aminatou: I know, you know? But when I think about a lot of people like me, my financial privilege is literally confined to the last three years of my life.
Ann: Right.
Aminatou: I'm not setup by family or by society or by anything else, and if anything the way that I still spend my money, it's legit like underprivileged people. I'm like a classic African support my entire family -- you know, I was like I need to start making some real cash because I have some real bills. So anyway when I think about that narrative also of like the amount of privilege and luck that it takes that is a thing that for a lot of people of flavor it scares us out of taking a chance for ourselves sometimes.
Ann: Mm-hmm.
Aminatou: Because it's the kind of thing that it is a crap shoot, right? I could've done this and it wouldn't have worked out, but also I come from the kind of life where things have to work out. [Laughs] Otherwise there's just no . . . there is something both terrifying and a little soothing about it in the sense where you're like oh, I actually do have to figure it out because I don't have the security net. There is no net here. Not some invisible like oh, I can go back and live with my parents. I was like I don't have any of that. So if I leap I have to fly.
You know, but at the same time the myth of the happy freelancer or whatever, when I think about that especially in our media tech circles it's always beautiful white people doing beautiful white people things. And at the same time I was like oh, they're trying to scare us out of this thing because . . . [Laughs] You know, it's like if it works out there's a lot of reward on the other side of that but it is terrifying. So I guess this is just a rambling way of saying it cuts both ways, you know?
Ann: Yes.
Aminatou: And it's such a hard thing to wrap your mind around.
Ann: Right. You don't want to deny the privilege involved in being able to do it but you also want to encourage all kinds of people to take the risks and take bets on themselves.
(17:50)
Aminatou: Right. Because a clear privilege you and I have also is we ain't got no kids and we ain't got no problems. And so when I think about the kind of person who can literally say like "I want to take a chance on myself" or "I don't want to -- the life that I've built here is great for myself," those people tend to be no kids, no mortgage. We're outliers in that sense.
Ann: Outliers in every way boo-boo. [Laughs]
Aminatou: Yeah, coastal elite outliers.
Ann: Um, okay, maybe we should take a tiny ad break and then talk about the good and the bad and the nuts and the bolts of what it is to work for yourself.
[Music and Ads]
(20:55)
Ann: Okay, so one thing I hear a lot from people who are five to ten years younger than I am, that kind of step or two earlier in their career, is they really want to be self-employed. I'm sure you hear this all the time too right?
Aminatou: Yes, I hear it about you all the time. Of course. [Laughs]
Ann: Oh my god, stop it.
Aminatou: All these media babies who are like "I want to live like Ann Friedman in a Los Angeles bungalow. How do I do that?" I was like you should get fired from a big job then you can do that.
Ann: Just decouple yourself from other people's goals. That's my number one piece of advice.
Aminatou: [Laughs]
Ann: But yeah, and so we went hunting for a survey and of course LOL there's like a survey of millennials saying 67% of employed millennials want to leave the traditional work structure to become self-employed. Which again we said earlier self-employed, people are not always using that term the same way. I'm sure those people do not want to become gig economy 1099 workers on a hamster wheel just trying to make ends meet. I'm sure those people have some kind of idealized version of what self-employment might be like. So maybe we should talk about the reality a little bit? Like your day-to-day.
(22:05)
Aminatou: Man, you know, the day-to-day is really interesting. Again when I left my tech job and I had a tech contract my day-to-day, besides the fact that I could work from anywhere I wanted, seemed all good at the time right? Like okay, I don't have to go into an office? What? I don't have to go to these stand-ups and the all hands? I'm just responsible for specific pieces of the puzzle that need to get made, like this is great.
Ann: And you weren't horrified by the tax bill? [Laughs]
Aminatou: Thank you, you know what I mean? But then reality starts setting in. First of all depending on your personality and who you are not having a structure to your day can be very destructive to the rest of your mental health and life and a lot of things. And it turns out that I'm one of those people. Cannot be left to my own devices. And then there is also the thing about learning -- you're your own boss now. Like in the sense where you're your own manager. You're your own boss. You're your own HR. You are everything. You are doing everything and you need to figure out a way to put on all those hats at different times of the day and give yourself the semblance of normalcy.
For me it was really important to really sit down with myself and be like okay, what does the day look like 9 to 5? Because this can't turn into like we're just fucking around and going to movies when we want to, going to museums at 4 p.m. stoned, because that's how I want to live.
Ann: So what -- so how did you do that? Did you make yourself like a . . . did you make a date with yourself to sit down and make a schedule? Or how did you learn? How did you learn what that schedule needed to look like?
Aminatou: I think I failed a lot in the beginning. Because the day was unstructured I felt like if I wanted to go to lunch with a food I could just pick up and do that. If somebody wanted to have a call I could just do that. And then I felt like my days were a lot of chaos.
(23:55)
And so I basically sat down and I was like what do I want 9 to 5 to look like? And what is the one thing that can ground me? And it's going to sound really dumb but for me it ended up being lunch. I was like it is very important to me that I make lunch at home as many days of the week as I can. It was also important to me that I work in chunks of time that could be interrupted. Whether it was like okay, from 7 to 11 I am sitting at the desk and I'm doing something and there's no calls, no breakfast, no nothing. That was something that was important for me to protect.
Also just figuring out how to get a rhythm for both the busy kind of work that you have to do and then also making room for the creative, big thinking picture stuff that you have to do and also the life admin that you have to do. That is just like, again, when I say that you're every part of a business, you have to take care of your own overhead now.
For me that ended up meaning blocking a lot of time to do specific tasks. I'm somebody who struggles a lot with that and it turned out it was very helpful. I've been doing it for long enough now that I have a very clear sense for myself of like okay, on Sunday night what do I want Monday through Friday to look like? And really sticking to that.
Ann: Yeah, I think for me it was the idea of thinking about weeks as opposed to days. The thing about my days is my body and my brain kind of regulate. Like I've got my good concentration hours in the morning and if I don't spend those wisely the writing is not getting done in the afternoon most of the time. Like most of it.
Aminatou: Yeah.
Ann: And so I think just being responsive to that in a day-to-day way was maybe more intuitive for me. It's also intuitive actually for me on the timezone schedule where most of the people I work with including you, my beloved friend and co-host, are on the east coast which means that mornings are more productive times to be in collaboration with people too for me on the west coast.
Aminatou: That's so funny. I love working the other way around because it means that I get mornings to myself and then all of my tech work and a lot of my creative work flows west and then I don't have to deal with it. It's like mornings are my own.
Ann: Ugh, it's almost like we're both happy in the places we live. [Laughs]
Aminatou: Whew, child, I know. But that's luck.
Ann: I know. But I think the thing for me that was really revelatory was thinking about my life and then my money as well in terms of weeks. And so one reason why I started doing an email newsletter on Fridays was because I was really feeling this sense of oh god, I've just been head down and really in it and what did I really do this week? What did I read? What did I write? Who did I talk to? How did I move closer to anything I actually care about? And sitting down to write a newsletter is a practice that in the very beginning was just that, a practice for myself to kind of orient my week and to think a little bit about making a catalog of what I consumed and produced. That is not something that I ever felt the need to do when I was on staff.
(26:55)
And it really also shapes the way I schedule now moving forward. So Friday mornings are set aside to do the newsletter but also there's we usually podcast at the beginning of the week. My weeks tend to have this structure to them that is a little bit more reliable week-to-week than my days are day-to-day. And that really works for me too, and I think despite all the caveats we gave about money and needing to do so many things for yourself that is one reason why I'm ultimately so happy self-employed is that I get to not only learn that about myself but then set that rule of it's fine that no two days look alike. And it's actually fine if I take some time off in the middle of the day to get stoned and go to a museum as long as it's not like every day of the week. I only get one of those a week or something like that, you know?
And so the weekly model has been very important for me. And also early on I made most of my money on recurring columns that I wrote once a week and so again scheduling-wise I'd be like okay, so I set aside this day to pitch for that column and this day to write the other column and then it added up to making some kind of structural sense.
(28:00)
But I would say like the biggest thing that I had to learn, if I could travel back in time to those early days of freelancing, I would really just remind myself that I was a business. I'd be like listen, I know that you are full-time writing and it feels like you're not a boss anymore or you don't have to worry about budgets or spreadsheets or planning. But holy hell please get a business credit card immediately. [Laughs] Like start to think of yourself as much as possible as a one-person business. Because once I started to do that I really -- I feel like my schedule got a lot more humane.
Aminatou: Yeah. I mean let's get into that then because I do think that this thing about seeing yourself as a business is so . . . that took me a while to see because like you in the beginning I was just a 1099 employee where I was like I make things for other people. And it took me a while to be like no, actually I want to setup a company that makes things for other people. And that distinction was so important for me.
Ann: Like it's an identity-level distinction almost.
Aminatou: Yeah. Aminatou, like me, I am obviously the one doing all the things. But having the front of an LLC, even though it is literally a pass-through that is done for taxes, having that -- like incorporating for myself changed the way that I thought about how I produced work. And I think like ultimately made me more accountable to the work I was making because it just seemed like a scaling up, you know? And a thinking of like okay, what does this company do? And what do I want it to do and what kind of work do I want it to produce? Which felt so much less daunting somehow, or I guess felt so much less pressured than I only have 24 hours in the day like Beyonce. Why am I not doing Beyonce-level work?
(29:55)
I think it did that for me. But back to the money, figuring that out also like how cash flow worked and I think at that point I had been doing it enough that I knew I . . . I basically knew how to chase a contract, like get signed on, on-boarded. You know, that whole song and dance that you have to do to get work. That I felt confident enough that I was like okay, there's actually a way to structure all of this so that it seems I can both have a little bit of personal removed from it and also feel that I'm a good steward of the company I've setup essentially. And so . . .
Ann: Oh my god.
Aminatou: Tell me.
Ann: Sorry, I relate to one piece of this so much because I think for me I actually went through and wrote some form emails or some rules. It's like we don't work unless a contract is signed.
Aminatou: Yes!
Ann: We here at Ladyswagger, Inc. don't work for free unless these three conditions are met. And I do work sometimes for less than my rate.
Aminatou: Ann, we have those rules at Deliberate and Not Afraid. Isn't that wild?
Ann: It's wild but that idea too because I think actually people -- please check me on this if you disagree but I think people really respect you a lot more if you say "Listen, I have a policy of only doing X" versus "Hey, look, I would really appreciate it if you could get me a contract before I start this work." It's like no, my policy is X. And I don't know, like people can really I feel tell the difference when you are coming from a place of my one woman corporate policy.
Aminatou: I think people can tell the difference but I also think that honestly the thing that has happened is it took you a while to figure it out and so you have more of a sense of worth and you are also clear about your boundaries, you know? So I think it is like both things. But again part of having a corporation is you do have clear boundaries. Like that for me was like a huge -- it's like galaxy brain exploding. And you're right, that's also the time where I was like okay, where's the kind of work I want to take. Here is the floor of money that I need to make to live kind of at the lifestyle that I have and also be fulfilled. And that was like . . . it was like "Oh!" Like we can do this. But also, you know, to be honest I've just been doing it enough that I knew how to handle cash flow. I knew how to track money at that point. If you don't have a bookkeeping system you're a fool. You should get a bookkeeping system.
(32:15)
Ann: A spreadsheet. A QuickBooks, a whatever you need. Something that is just your business money, yeah.
Aminatou: A QuickBooks, a human being. Like this is also the time where honestly there is me, Amina, like my money and the things that I do and how I spend and then there is the company money. And getting into that mindset of oh, actually I work to pay myself was something that was also like an illuminating process for me.
Like I have a credit card for my company which is the best advice you've ever given me. You were like oh, if you just get a work credit card it's easier to keep track of expenses. Galaxy brain, like poof. This is crazy.
Ann: [Laughs]
Aminatou: But the thing that also did for me was like well, I have a company credit card and I don't do personal expenses on that credit card.
Ann: Yep.
Aminatou: And it's been really good to separate that out. It's like sure, even though I would love to buy a [0:33:12] on the DNA tab, not going to do that because that is a personal expense. And so I think too that you just start seeing the ins and outs of how you spend money, how you can expense things, and truly how you can budget and the lifestyle you can lead ultimately.
Ann: I have a question. How did you figure out how much your time was worth? Because for me I don't feel that I was really trained in that. Writers are often paid per piece or per word. You're not paid per hour and therefore when I started to think about okay, if I want to make more money this year than I made last year and I can't physically write more than I did in 2012 or 2013 how am I going to do that?
(33:55)
And I think that part of that answer was figure out how much I want to make in a day or how much I want to make in an hour. And maybe it's a little different for you based on how you bill but I'm always curious about that question of how do you judge the value of your time in American dollars?
Aminatou: You know, honestly that for me also was a lot of trial and error. I think that it was a little easier for me because I tend to work more on a project base. I think that if I'd had to write or do it for pieces it would probably drive me nuts. And so I think of my time really as a day rate or as an hourly rate. And friend of the podcast Elana Berkowitz who is on the Tech LadyMafia listserv that Erie Meyer and I started gave some really good advice a while back about figuring out your hourly and your day rates was to take however much money you wanted to make in a year, take off either two or three zeroes to figure out your hourly and your day rates.
That was like -- I'm not quite sure how she came to that but I remember just having that as a baseline for me, thinking like okay, this just means I can be flexible. I also work with people from across the money spectrum, like anywhere from corporations to small non-profits. And so it really -- it made me feel like okay, there are places where I could stick to the rate even if it sounded outrageous to me and honestly nobody has ever pushed back on it, like of the top-tier people that I work with, which makes me feel like it's not enough money. But that's a conversation for a different day.
But it meant if I could be flexible enough to get that rate with big corporations that if there was a non-profit that I wanted to work with I could be flexible with them in terms of that, you know? But I think that now it's a thing that I just know intuitively. I have a rule now that is like -- god, this is going to get me in so much trouble with brands that I work with, but it's fine. I have a rule now that if I get asked to do something that is -- it just feels like a one-off or just a thing that it's like a nebulous amount of time spent, you know those requests?
Ann: Where you're not sure how much of your time something is really going to take.
(36:00)
Aminatou: Right. Could take 30 seconds. Could take four days. Who knows? The thing is just very nebulous. I'm like I don't get out of bed for less than a month of rent. That's the price for doing that. Like it's not a thing that is part of my regular work stream. It is not a way that I have factored in that I needed to make income that year. It is just a weird, nebulous opportunity that has presented itself. I was like it has to at least be worth a month of rent. This is not financial advice. This is how I do this and so far it has panned out.
Ann: I love that. I'm always curious where other people draw their boundaries. One thing that's been helpful for me is not only answering some of those questions but being a little bit more transparent with the people I work with about it. So for example if I do take something that is almost like an in-kind donation, say it's like I'm giving my time because I care about a cause of a publication or whatever, or if I'm writing for some other reason for less than my rate, I will say that. I'll be like "Listen, my rate for something like this would normally bottom out at a thousand dollars or whatever."
Aminatou: Yes.
Ann: But I'm going to write it for you for 350 for XYZ reason. Just know that in the future this is it not a rate that I will frequently say yes to/this is not a living wage or market rate. And that's how I get around the fact that a lot of the writing work that I do is frankly subsidized by ad income from Call Your Girlfriend or other business streams that I have. I recognize that by saying yes to a rate that is ultimately not a living wage if I were just purely a freelance writer, I want something that is written that editors can use to go back to their higher-ups and be like "Hey, we're way under market." You know, something that is at least a trail acknowledging that I am not trying to undercut the market for other people.
(37:50)
Aminatou: Yeah. I mean that's really interesting. Like I don't find myself in that situation, again because I don't write. Media notoriously cheap. But that conversation is interesting because I realized over the past two years that I do have a very firm boundary on not working for free unless it is a request from a friend and it has to be tied into a larger cause. So it's like if you were like "Hey Amina, I would love for you to moderate my book event," this is one line of request that we get a lot that I don't think a lot of people realize. You and I moderate a lot of book conversations for other people.
Ann: Right, with authors who are on tour to promote a new book.
Aminatou: Exactly. That is not compensated work. It doesn't mean that I don't spend the entire time reading the book. Probably I would say like a couple of hours prepping. All in all it's like close to 20 hours of work if we want to be honest, you know? 10 maybe to be honest. But doing all the things. Like we are good moderators of conversations. And so like requests like that for Amina, you have to be a friend or you have to be somebody that I have a connection with at least and then we'll talk about it. Because I dot think that it vastly undercuts the market for other people which is not cool, which I would say especially in tech and marketing you see a lot more.
Ann: Right. Moderating a public conversation is a skill that should be compensated frankly.
Aminatou: Yes. I'm like very good at it. Hello? So with those requests I have been more transparent with people where it's like okay, here's the deal. I'm doing this because you are a pal or like it's a cause that I really believe in but this is a thing -- this is not a request that you should be asking a lot of people. Like if you find yourself frequently asking people to work for free you should really fucking check yourself because it's gross. And a lot of times you are getting paid for the thing that you are asking other people to work for free for which makes it even grosser.
Ann: One reason why we wanted to talk about this on an episode of the podcast rather than just on our personal text thread where we talk about stuff like this all the time is that we were talking about some people we know who are in staff jobs and about how a lot of these skills that we're talking about of like recognizing when something is getting added to your plate or being aware of how much your time is really worth, things like that, would've really helped us in our days on-staff to think about our work that way.
(40:10)
You know, yes, you don't get to negotiate with your boss about whether a project is going to require so many hours that you're undercutting your own salary for example. However that is good info for you, a human being, to have and raise at your next performance review. And the mentality that everything that you do in the scope of a job is a skill, like that is presumably agreed upon in a job description and if your employer goes outside the bounds of that you need to redraw the contract. Some of those ideas are things that I'm like I really wish more people in the working world, women in particular, were thinking about as they advocated for themselves within their jobs.
Aminatou: I think about this all the time and especially as it relates to women that we know in staff jobs that we sometimes have to work with, you know, in a freelance capacity is just this idea that you can just keep adding on to the plate. Like a thing that I wish that -- you're right, that I had known when I was working in the office is I should probably think of every different skill that I have or think about how many different projects I am juggling at work and looking at them that way as opposed to just like oh, I'm an analyst here or I'm a -- like I do XYZ job here and then everything has to get done.
It's like no, you should account more for your hours. Like one thing that is great about the kind of work that we do is I at least, I keep my hours down to the quarter. Like I know exactly how much every single task that I do takes me to do and I log all those hours.
Ann: I do not do that. [Laughs]
(41:50)
Aminatou: Well that's also because you're writing but when you're working on a project basis you kind of have to do that, you know?
Ann: Right.
Aminatou: Like that was very eye-opening for me, like oh! Okay, some things only take 25 minutes to do. Some things take 25 hours to do. And when I started seeing it that way, like with a time tracker, it was so much easier to just -- to understand like the bullshit of what the work plate looks like, you know? And it's also like welcome to being in a line of work where if you want more than what is in the contract you've got to pay for more than is in the contract. That's how we do over here.
Ann: I agree. And I think the other thing that I think about sometimes is when it comes to growing your skill set, that goes hand-in-hand with things getting added to your plate. Like one reason we are even speaking today on a podcast is because a million years ago when I believe Gina planted the seed that we should do a podcast I was like oh, wow, audio. A thing I don't know anything about making would probably be a cool thing to learn how to do. Not in the sense of oh, I'm definitely going to add this as a revenue stream to my independent business but much more in the sense of like this is a skill set that I want to grow. And sometimes when you're on staff it does not come easily to think about learning new things in that same way.
You know, I would say the same thing is true with figuring out how to monetize my newsletter. I could've just put a banner ad on it and kept going. But I was like no, I want to muddle through and figure out this software solution and this multifaceted way of funding it which is honest to god a huge nightmare most of the time. But I have learned a thing that I otherwise had no idea about and I gave myself permission to do that. And sometimes I think about huh, what if I had applied that line of thinking to my staff jobs where it was possible? And the best staff jobs I had really enabled that anyway, like really enabled a lot of growth because I was pushed to do things that were outside my skill set.
[Ads]
(45:00)
Aminatou: I have another money question for you.
Ann: Hit me.
Aminatou: How did you figure out basically how you were going to pay yourself, how you were going to live, and how to do that with the inconsistent ways you are paid when you work for yourself?
Ann: I would say for probably at least the first two-and-a-half to three years of my self-employment I did not. It was literally just money comes in. Money goes out. I'm in a scramble. I rely on my credit card to fill the gaps. That's the honest truth. And then once I started to get more of a foothold which I just have to stress it came with having some of my own revenue streams and not always being reliant on writing contracts, that's when I was like okay, what seems like a reasonable salary? That's when I started putting away the max contribution limit for a Roth IRA and, you know, working backwards from this is what I made last year. This is how much more I have to do if I want to save more next year. And kind of your 101 budgeting things that I'm sure every personal finance book can do better than I can, but applying that to a business.
(46:10)
So yeah, I just want to stress that actually answering that question of how much do I pay myself and how do I think about the way I'm moving my money around, it honestly felt like a privilege when I got to start answering that because it wasn't just scramble, scramble, scramble, money goes out as soon as it comes in.
Aminatou: And do you have a specific thing that you do with every check that you have? Like for me it's like 25% automatically goes to a savings account for taxes because freelancer taxes are whew child. Like 25% goes to taxes. I send 20% to my SEP IRA. It's a kind of retirement account that you can have if you're self-employed which is also great because it means that it reduces your tax burden so it's kind of like giving yourself a 20% raise anyway. But those are things that I had to systematically learn how to do. And so that also for me factors into how much I ask for when I give a rate quote for something. It's like half of it is already out of the door as far as I'm concerned. Like you don't see half of the money immediately, or you shouldn't see it. And so that's a thing that's always top of mind for you. Do you have a system?
Ann: I mean I don't get -- it's different. A rate quote and a project rate are not the ways I work. So basically what I do is I can say okay, here is how much I can roughly rely on based on the previous year from my newsletter and from Call Your Girlfriend which are the revenue streams that I own and are fairly consistent and predictable. At least kind of a minimum amount. And then the delta in there is what I have to make through speaking or writing or whatever, whatever other cocktail -- other audio things, whatever other cocktail of stuff I'm doing. So that's usually just a hard number.
(47:45)
And I can often know at the beginning of the year, like for example when I had a column contract, I was like okay well I'm going to write one column a week and that factors out to X and that means I need to write three more features this year in order to make up the difference or something like that. When I look at my income as a pie -- you know I love a pie chart -- nothing is more than . . .
Aminatou: [Laughs]
Ann: Nothing is more than a third. And so what's kind of nice in a way is if I had a really bad year in one area it's like it's okay. I mean I feel like I'm diversified enough. So I don't have quite like that this is my hourly rate because that's just not how I get paid but I do think about and rely very heavily on the things that I own and that's why I always tell -- you know, we reference those people who are a little bit earlier in their career who really want to be self-employed. I always ask not just who do you want to work for as a self-employed person but also what do you want to make and what do you want to own? What little micro business do you want to own? What IP do you want to own? What are you doing to set yourself up to have a little bit of if not passive income at least more stable income so that if, you know, your industry kind of collapses -- [Coughs] media, I'm sorry -- but it's like you are protected in some ways from the fates and fortunes of that one big client or that one major publication that you're doing all your work for. And for me that is more the name of the game than precisely gaming out how many projects at what rate.
Aminatou: Yeah. I think I'm really glad that you brought that up and especially having a diverse stream of income is so important. Like one of the things that I always tell the babies who are like "How do I live your life?" I'm like hmm, don't do it. But if you're going to put your own shingle up or however that metaphor works . . .
Ann: Yeah, hang out your own shingle? What is that weird shingle metaphor?
Aminatou: Yeah, I don't know. You know, some white man metaphor. But anyway if you're going to shingle out with the white man you need -- I would say if you're going to strike out on your own at least two contracts that you're working on and having two clients that you have that are a reliable source of income for you. And also, you know, another thing that is helpful about this stuff, talk to your other freelance friends.
(50:00)
I remember in the early days of this always feeling like it was a scramble to the finish line and I was like how is everybody else making this look so good? And then I found out that most of the women that were in my same kind of line of work had very rich husbands. I was like oh! Good. I was like you also have a diverse stream of income.
Ann: [Laughs]
Aminatou: This is great. But I remember the friend who told me that. She was very blunt about it. She was like oh, the reason I can work these hours or I took this job that you didn't want to take or whatever, because you know Shine Theory is also always referring your pals for jobs that you don't take, like that's how we stay happy in the freelance community, and so I remember her and being like "How can you afford to take this job that was truly not a good deal for a lot of other people?" Like she wanted the experience but really the money came from her marriage. Which is like fine, this is not a knock on people who marry rich people. I hope to marry a rich person one day. That's the whole point of how marriage works according to Amina. But so anyway thinking about not comparing yourself to other people unless you have the full scope of what's going on.
Ann: Right, unless they're being transparent with you. Yeah.
Aminatou: Yeah. And I found that at least in my little digital tech community before -- I don't do that anymore, but when I did that, I was in a crew of people who were very transparent and very generous and I don't think I could've scaled myself or my business without a lot of the information that I got from them.
Ann: Absolutely. And I think it is incumbent on people like us who are making a living self-employed to talk to people who are in our fields about how we make that work, you know? And I really think that there are some things that are not transferable as advice or information that are high specific to each person but there's a lot that is. God, I just kept thinking when I was first coming to terms with the fact that oh, I was self-employed for a while now. I'm not just doing a freelance writer thing while I figure my life out. I really wish there were some kind of guide of okay, now you need this kind of bank account. Now you follow this guide to figure out how much money. You know, like some kind of plug-and-play solution.
Aminatou: Yeah.
(52:15)
Ann: And at the time I was like oh, this is a huge opportunity. Somebody should write it. And now with a little more distance I'm like it's unwritable for anyone but yourself. All you can really do is gain resources and information from the people that you know.
Aminatou: Yeah. And also going back to the people that you know part of the reason why we were able to go into freelance is that we worked in offices for so long.
Ann: Absolutely.
Aminatou: You know, when I think about all of the people who have hired me or who hired me in the beginning I either worked with them or I knew them or I had hired them. Like I can't tell you how much of my kiss-down, not kiss-up tactic came back to pay full-fold. People that I helped place are now coming through for me in a very real way and that was so apparent.
And so when I think about people who are super early career who are like I want to go out the gate and do this I'm not saying you can't do this. But a part of the matrix that is maybe not apparent to you is that everybody kind of already knows everybody and everybody has worked together in some configuration.
Ann: Right. And yeah, it's absolutely you cannot decouple the fact that I can make a living as primarily a writer from the fact that I was an editor for years and the people I'm working for were my peers then and people whose brains I really understand now because I did their job for a long time. Like there's a lot of things that are not only related to connections that I've made but just like things I learned in the specific set of staff jobs I had. And I'm glad you prompted me and we both talked about our initial false start at freelancing because I think that the timing piece of it after you have built up a certain amount of knowledge and connection cannot be understated, the importance of the timing.
(54:05)
Aminatou: Right. And speaking of connections, you know, like another way -- one of the things I do miss about office culture . . .
Ann: Wow.
Aminatou: I can't believe that I'm going to say I miss it because honestly 90% of the time I don't miss it. But there are truly days I wish I could turn around and have somebody immediately there to talk to, you know? Or that sense of community. But the truth is I made that for myself within the other self-employed people that I know. And so really seeing yourself as part of a cohort, whether you're the person who you organize the monthly meet-up for everyone, they don't even have to be people who do the same job you do. They just should be self-employed like you or whatever. Or like I have time in my calendar that is blocked out every month to check in with certain people about certain kinds of work that we do. You don't need to be like working in an office side-by-side with people to feel like you have colleagues. Like your colleagues are everywhere.
And so I really think that taking your head out of the computer or whatever it is that you do and really making time to connect with other humans is so important. Probably the bulk of my creative spark comes from those moments.
Ann: I agree. I do not feel lonely in freelancing but that is because we also build community in a concerted way. You can't do this alone. Like nobody should be expected to truly do it alone.
Aminatou: We talk about this so much, like you and I. I also hope that it inspires some people to go out on their own and take a chance on themselves because it is like truly -- it's a real thrill, and if anything more people will try to hire you. I used to have the fear that if I left my big Google job nobody will ever want to hire me. The opposite is quite true; people want to hire you all the time.
(55:52)
Ann: It turns out people love not paying your benefits and getting the benefit of your brilliant brain. [Laughs]
Aminatou: Oh no, I mean hire me back into a full-time staff position which is not something that I'm interested in doing. But I also hope that for some people who have been waffling about what they wanted to do that maybe this is a good conversation that prompts them to actually put their nose down and stay where they are because, you know, these bullshit Jeffersonian Yeoman ethics, it's not for everybody. [Laughs] And there is a part of it that is truly just this American ideal of the small business owner and just feeling like you're living off of the land or whatever. The truth is our government is not great to small business owners. Most small businesses fail and a lot of those small businesses are owned by women. That's not an accident. Instead of thinking about your career as this ladder that you have to climb I would look at it more from a goal-setting and from a learning perspective and saying what are the things that you want to do in this life and what are the things that you want to learn in this life? And how can you set yourself up to do that?
Ann: Right.
Aminatou: And that doesn't have to follow a linear path at all. The economy is in shambles. Somebody will always pay you to do a skill that you have and there's something kind of exciting about that.
Ann: Right. It's not a value judgment of like it's better to work for yourself or to start a business or whatever. It's just sort of like there are a very different set of pros and cons that work for both of us who have problems with authority figures. It is not necessarily for everyone. [Laughs]
Aminatou: And also have health issues. And also have health issues.
Ann: Sure.
Aminatou: Everything has a trade-off. The flexibility that you have on setting your own schedule is a trade-off for something else. And I think I am probably done -- not probably. I am 99.99% sure I am never working in an office again unless it's in the White House when I'm president when they change the laws on that. But that feels very good to just be like oh, this is not a thing that I'm pursuing anymore and I'm happy but there are real trade-offs that were made and I'm okay with them. So you just have to pick one thing and not look back.
Ann: Right. And to all my fellow self-employed people if you don't have a business credit card do yourself a favor in 2019. If there's only one thing you've learned from this conversation make it that. [Laughs]
Aminatou: Get yourself a business credit card. Talk to your friends about dollars.
Ann: And be nice to yourself. Be as good a boss to yourself as you would want someone else to be to you. That is like the end of the day too.
Aminatou: Oh my god, what is the point of working for yourself if you can't be the boss that you wish you had? Like what is the point?
Ann: I'm silent. There is no answer to that. There is no point. [Laughs]
Aminatou: There is no point. Thanks for being a good colleague Ann Friedman.
Ann: Oh my god, love having you as a colleague. Love having Gina as a colleague and I'll see you on the Internet.
Aminatou: I'll see you on the Internet and in the Google Doc soon. You can find us many places on the Internet, on our website callyourgirlfriend.com, you can download the show anywhere you listen to your favs, or on Apple Podcasts where we would love it if you left us a review. You can email us at callyrgf@gmail.com. We're on Instagram, Twitter, and Facebook at @callyrgf. You can even leave us a short and sweet voicemail at 714-681-2943. That's 714-681-CYGF. Our theme song is by Robyn, original music is composed by Carolyn Pennypacker Riggs, our logos are by Kenesha Sneed, our associate producer is Destry Maria Sibley. This podcast is produced by Gina Delvac.