• Pip Usher’s Website
• Pip Usher’s Instagram
• Paula Scher
• Seth Godin’s Freelancer Course
• David McCullough
• Esther Perel
• The Kinfolk Entrepreneur

• Introduction [00:00]
• Episode Introduction [00:51]
• How to Become a Freelance Writer [02:04]
• Advice for Aspiring Writers [05:46]
• Routines of a Professional Freelance Journalist [07:53]
• How to Make Money As a Freelance Writer [20:31]
• Short Episode Break – Support the Podcast [25:00]
• Challenges of Being a Professional Writer [25:43]
• Self-development As a Creative Professional and Freelancer [30:28]
• How to Improve Writing Skills [38:55]
• What Makes a Good Interview [41:23]
• How to Stay Motivated As a Creative Professional [47:41]
• How to Be a Better Creative Professional [52:00]
• Episode Outro [53:30]

Pip: “Treat each piece of work seriously. Even if it’s something that you don’t feel very invested in, you need to treat it with care.”

This is the Creative Voyage Podcast, a long form interview show with the mission to help creative professionals to level up. I’m your host Mario Depicolzuane. I’m a creative professional myself active in the fields of graphic design, art direction, and creative consulting. In this podcast, I present in depth interviews with some of the world’s most inspiring creative professionals revealing the stories that shape their lives and careers, plus actionable strategies to help you take your mindset and skills to the next level. I invite you to join me on this journey.

Mario: In this episode, I talk to a freelance writer.

Pip: I’m Pip Usher. I am currently living in Jerusalem and I am a writer.

Mario: Pip Usher is a journalist known for her cultural pieces and long-form profiles. She has written for titles that include The Financial Times, Vogue, Kinfolk, Departures, Wallpapers and GOOD. Referred to by Kinfolk as their secret weapon, Pip has interviewed leading names in the fashion, entertainment and art world. In addition to her editorial work, Pip crafts high-quality content for Vodafone and tradition at Cathay Pacific. 

Prior to journalism, she worked in advertising and account in Burberry and Tiffany & Co. amongst her clients. After living in London, New York, Beirut and Bangkok, Pip has made Jerusalem at her home at least for now. 

In this episode, we’re going to listen to the highlights of the conversation I had with Pip in June 2019. In our conversation, we covered topics such as advice for writers who are just starting, tips on how to improve our writing skills, what makes a good interview, challenges of being a freelance journalist, the influence of recent motherhood to her work and much more.  

Pip has been fascinated by words ever since she was a child. As a kid, her favorite sweatshirt had a print saying, “So many books, so little time,” a sentiment that I’m sure a lot of us can relate to, that early inclinations certainly shapes her path. However, working with words as a professional came as an outcome of a gradual process one shaped by circumstances, determination and early self-doubts. 

I started my conversation with Pip talking about how she became a full-time freelance writer and the lessons she learned during the time. 

Pip: I would say that I made that jump out of circumstances rather than a deliberate decision on my part. We were living in Beirut and up until that point I had always had like a pretty linear career trajectory. Then as soon as I left London and the kind of safety net of like, “Oh! This is a good job and with a company, and then this is what’s going to come after that, and get your pay rise here, and you’re this, that, there.” It just forced me to be more creative in terms of how I made money.

In Beirut I started working for a magazine and writing every day and I enjoyed it, but it wasn’t until we moved again to Bangkok and I just thought I don’t want to work for another local company where I don’t speak the language and my experiences at least in Lebanon were like it’s usually mayhem in this company. I thought, “Okay. Well, I’m going to do it myself.”

Then even when I started freelancing, there was a whole process in terms of my mindset needing to change, because first it was like this is something that I’m trying to do, and then the time as I grew in confidence. My work got better and better and I started understanding really how the nuts and bolts of it worked. I was like, “No. I need to own this. I’m a journalist.” That’s what I do. So I need to step into that. I didn’t see and feel confident introducing myself as that and identifying it on a personal level for myself.

Mario: Yeah. That was basically like a transition in a way. 

Pip: It was definitely a transition, yeah. I could feel myself in the early stages not feeling confident enough to say this is what I do, because I didn’t have a staff job with The New York Times or something and then it was like, “Well, why am I not taking myself serious? “How can you expect other people to do that if you’re not going to step into that role?

Mario: Yeah. Was that like – I mean, you started, was it around like 4 years ago?

Pip: Freelancing, yeah. Yeah. That was four years ago.

Mario: What would you advice yourself looking back now with your current experience?

Pip: I think it was a process that I have to go through and I don’t think I would view any of it differently. I guess I would maybe be a bit more gentle on myself. I’m impatient. If I have an idea, then I want to do that idea straight away. If I send an e-mail to an editor, then I want a response right away. I think with freelancing, you have to understand that it’s a gradual process and it’s like building up these layers, right? You don’t just get to the top of the mountain in the first month, but I think I would get really frustrated in the beginning that I wasn’t there.

For an aspiring writer, it can be a daunting mission to start working professionally. Pip successfully embarked on the journey, so I was curious to hear what advice she would give to a new talent entering at journalism.

Pip: I have a twofold answer. The first part from a more creative standpoint would be to actually be a really good writer. Just because you like reading and maybe you wrote a couple of essays for your A level, that doesn’t necessarily translate to writing a thousand words a day. I think you need to maybe just be like a realistic grasp of your abilities and how much you’re actually really want to do this, because you have to work fast and you have to write copy pretty quickly. Yeah, it’s competitive. I think that’s one side of it, is just understanding what it’s going to look like for you.

Then the second side of it, which I don’t think gets talked about enough because I think it makes people uncomfortable to acknowledge their privilege, but you need to have some sort of safety net if you’re going to just launch yourself into it. You even need to have stockpiled savings that you’re happy to spend or you need to have a setup, like I did, when we moved to Thailand that I meant that I could freelance and have, in those early stages, months, where I wasn’t having money come in and still have my apartment and still have healthcare.

I think you have to be realistic about what your financial setup is and whether you can take that risk. I know that’s like not the advice that anyone wants to hear, but the only reason that I could take that leap is because I lived in a very inexpensive country and I was with someone who is like, “Yeah, I’ll cover the cost while you could get going on this,” and that’s a really big privilege to have that.

A work of a creative professional, especially a freelancer, takes more than simply doing the activity implied by the title. A freelance photographer does much more than take photos. A freelance writer doesn’t just write. The things we do around our craft plays a significant role in us being able to do that craft professionally. Here, I talk with Pip about her typical work week, the opportunities and challenges of a freelance schedule and how recently becoming a mother is influencing her work.

Pip: Last week I had a bunch of deadlines that were hanging over me and I knew that I wanted to get them done before. I flew to England on Friday, because – maybe we’ll touch on this later. When you freelance, you basically never really feel like you’re on holiday. Even though you have so much freedom, you also constantly feel like you’re going to get an e-mail that you have to say yes to and then you’re like relaxing week away goes out the window.

I had two big news articles that I need to write for Vodafone. I do a lot of commercial work for them, and those are about a thousand words each. Then I had another big travel piece for a luxury fashion site for Matthew Fashion. Then I was also pulling together a ton of interviews for a long-form piece that I’m writing for Vogue in this recent week, and I have a now six-months-old baby. Quite demanding.

I would wake up. I have to leave the house, because I can’t work when I’m in the house with her. From 9 till 1, I go to a café down the road. I get a very big coffee as soon as I arrive. Then I have a do-to-list for each day. I don’t necessarily stick to it. A lot of the time I’ll get to the end of the day and then I’ll be copying and pasting bits from Wednesday into – Just like try and refigure it, but it makes me feel like I’ve got things under control and it often makes me feel extremely satisfied when I can delete some things in the to-do-list. 

I just try and write, like one of these big Vodafone news stories, I’ll just – God! It’s quite weird to try and think like what do I actually give. What do I give? Yeah, I guess I start putting quotes down on the page that I think are insightful and I build around with stats and research that I think adds to the piece and then I just go over and over. Some people sit down and they just write from start to finish and then they go back and fine tune it, whereas I like to constantly fine tune as I’m going through. So I’ll like write a paragraph, go back, read it through, change it. Get on to the second one. Read through from the very beginning again. It’s like this constant refinement. Then I get to the end, and by that point I just never want to look at it again. Then I usually get Oli, my husband, to have a read. Well, only if it’s a big thing. If it’s a big thing, I make him have a read and to tell me if he thinks it’s good and engaging. 

Yeah. What did I do? I did like a thousand words over the weekend, then I did another thousand words on I think Wednesday, another thousand words on Thursday. Then in the evenings, because I was speaking to people in the West Coast of America, I was interviewing, which you then have to transcribe and then figure out what’s interesting from that. It’s just like I guess quite a bit of coordination. You’re setting things up and then you also need to allow yourself chunks of time where you just actually start writing, which can be the part that you put off the most. 

Mario: Yeah, and besides coordinating about things that you’re going to be writing about and writing those things and making sure you can make that happen. I’m sure there’s like kind of admin things or like kind of new business types of tasks.

Pip: Yeah. In terms of new business, I think I go through spurts of enthusiasm, where I’ll have a day or a week where I’m like, “Okay, I’m going to contact these editors. I’m going to contact these businesses and tell them that I want to write for them.” Then I just get distracted by the imminent deadlines in front of me. An admin is – Yeah, I guess it’s like an ongoing, like keeping on track of when invoices were submitted and when you should be paid and also just ton of checking in with people. Yeah, keeping everything taken over.

Mario: I mean, as you mentioned, when you’re a freelancer it’s – Yeah, easy to – Even though you have a lot of freedom in how you operate and how your schedule looks like, you can always feel like you can do more or work more. How are you navigating that? I mean, on average, how much do you work a day?

Pip: At the minute, I would say that I work – I was going to say four hours a day, but it’s actually more, because then the evenings come into play. Let’s say maybe like 5 or 6 hours, but spread out in the morning. Then I’ll have Zadie my daughter throughout the afternoon and evening and then I’ll like start again in the evening with interviews. One thing I’ll say is that having a baby makes you so productive.

I could be so relaxed in terms of like, “Oh! I’ve got the whole day, and even if I don’t finish it today, then I’ve got all of tomorrow.” Now, it’s a race against the clock, and that is really – It really like puts a fire up your ass. It’s great. 

Mario: Yeah, which is actually kind of – 

Pip: Stressful, but it’s great.

Mario: Yeah. It is kind of what you need. I mean, that’s why like deadlines really help, and when it’s time to like turn in something, that would do it.

Pip: Yeah. Yeah.

Mario: Not like two weeks before.

Pip: Yeah.

Mario: That way, that’s interesting.

Pip: Yeah. My other advice for freelancers, have a baby.

Mario: Actually, I wanted to like talk to you about motherhood, because you became a mother recently. I’m just curious like how that besides what you mentioned now, kind of how that influences your work.

Pip: I think it’s ultimately been really positive, do what I do and have a baby, because it has given me a load of freedom to work around my schedule. Yeah, I can have a day where I’m like, “Okay, I don’t have that much to do. So I’m just not going to do anything,” rather than feel pressure to go into an office. 

However, I would say like at least every couple of weeks I now have some sort of existential crisis, because I just feel like I can never take a breath. I’ll finish everything on my to-do-list. I’ll feel euphoric for like maybe three hours and then something else will come in. That is a really great feeling in the sense that, “Okay, I’ve got enough work now that I’m not even actively seeking it, like stuff that’s just coming my way. As a creative, that’s the position you want to be in.” But when you’re balancing it with a small baby and like her erratic schedule and not sleeping through the night and all of that stuff, it can just sometimes feel really overwhelming, because like we said earlier, it’s not like there’s a set time that you’re working or like set days that you work. It can kind of be always. I also think when you build something up yourself, it’s really hard to let opportunities pass by or go to someone else. It means that when someone e-mails me and says, “Hey, we’ve got this. Do you want to do it?” It’s basically just feels impossible for me to say no, because it just pains me even if sometimes maybe I should say no for my own sanity. 

Mario: Yeah. I mean, there’s a lot of challenges when you’re like just starting to freelance or then be a creative professional. But then, if things go well and you go through some of those initial hurdles, then these new challenges, which are let’s say better problems to have, which is good. But it’s, yeah, equally important to address them.

Pip: Yeah. I think it just becomes hard to say no because for so long, as you’re building this, you just desperately want to get these e-mails. It feels really crazy and counterintuitive to say like, “Oh, I just can’t.” That can definitely – It can mean then that because I’m trying to fit everything in that I then – I’m also working at the weekends or – Yeah, it can feel quite constant. 

But ultimately, it’s great. It really gives you a separate identity to raising a baby. I’ve really enjoyed having that time away to write and to just be like normal, like my old self, whatever, and then come back to Zadie. It just feels like you can enjoy both sides of your life a little bit more having that other aspect. Does that make sense?

Mario: Yeah. None of us is like one-dimensional – 

Pip: Yeah, exactly. Exactly.

Mario: Part of trying to know how to work in a freelance way, for me, it’s also in the future, if I have a family, I feel that those skills, or that freedom that can come with it can be good for family life, or for raising kids. Have you ever thought about that in that way?

Pip: I don’t think I thought of it in relation to having a family, but I definitely thought of it because I knew it was a lot. It sort of became like a way of being able to move countries and not start again. It’s like being a turtle and then having your shell on your back and you can just go from one spot to another and you still got everything you need with you.

I moved from Thailand to Israel and that’s a huge move, but I carry all my work over with me, and that creates a really nice sense of continuity as well. It has definitely given me the flexibility to move around the world, to travel a ton and to like lead my life with a lot of freedom. I guess that applies now that I’ve had a kid as well, being able to really flexible about the hours that I work and the times that I spend with her. 

Mario: Let’s go back a bit to your last week. You said most of the mornings you would like go work for a couple of hours. Then like how does the rest of your day look like?

Pip: Well, then I’ll come back and put my laptop to one side and have Zadie usually until – I don’t know, 5 or 6PM, and then by that point America is awake and the people that I wanted to speak to are ready to go. So I hand her over and lock myself in a study. Although I have noticed that when I’ve transcribed interviews recently, you can hear a baby crying in the background with every single one, like without fail, you can just hear like, “Eee,” in the background.

Yeah. So then I’ll do that for a few hours. Then if I can still bare to look at my laptop, I’ll usually try and look over one of the pieces that I’ve written a final time or just tighten it up a bit more. But it’s stressful. It’s one of those weeks where you start out really motivated and then you get the first piece of work done and you’re like, “Yeah!” and you get the second piece done and you’re like, “God! I’m on fire.” Then by the third piece, you just can’t. You’ve like lost all momentum. It’s like, “Ugh! I have to do this, but I’m so tired by this point.” Yes. I mean, I did it. I was really proud of myself.

As designer Paula Scher observed, “It will never be enough money if you don’t like the work. That’s just the truth.” However, when that’s checked off, a common source of struggle for freelance creatives could be making enough money doing what they like. I’ve asked Pip to share how she’s navigating the financial aspects of her creative practice.

Pip: As I’ve gone on, I’ve realized that the best way to do it is to have – One of the most sustainable way to do it is to have a mix of editorial clients and commercial clients, and the editorial clients are – How many? I probably write really regularly for about 3 and then ad hoc for probably another 3 or 4. There’s constantly stuff that I have to do for different magazines and websites that I write for, and that’s really fun and filling and varied and I love doing that. 

However, that doesn’t pay that well and it can a bit stop-start, because if you’re working through a magazine’s timeline, then there’s going to be like birth and then quiet periods and so on. I have now maybe, yeah, at the moment. I’ve got two commercial clients. I have Vodafone, who I write all sorts of news stories for around technology and then I have – &Tradition, who I do press releases, like storytelling around their product. That not only pays much better, but it’s really enjoyable as well. It’s a different type of writing, but I really like having the variety and working in different environments and with different voices. I think I like having that mix not only from a financial perspective, but also just for my own enjoyment. It keeps things fresh. 

Then another thing which has been really helpful is that I have always taught yoga, and not in Jerusalem, because I became pregnant, but in Beirut and then in Bangkok I was teaching like four or five times a week as well as all of my writing. So not only did I love having like a very physical outlet and something where I’m working with people and building relationships, which you don’t do when you’re a freelance writer. You’re alone in front of the computer. It’s really nice to have physical human contact. But also it meant that I would have a very steady source of income from that, which would balance out the month where I wouldn’t have any income coming in.

I really, really recommend whatever creative or freelance profession you go into having a few trades, I guess, so that you’re not tied to one and it means that if you’re having a bit of a famine moment with your writing, then maybe do teach a little more. Yeah, it just puts less pressure, I think.

Mario: Yeah, exactly.

Pip: I just always like to have as much variety, I guess, with everything that I do as possible and it’s given me that.

Mario: Yeah, and also you’re not from like a creative perspective. Maybe you’re not like too tied to just like one thing. You’re not like too identified with only writing. If that’s not going well, in a sense, you have other things.

Pip: Yeah, exactly. I think something that I guess pride myself on is being adaptable. I’ve moved all around the world. I’ve around a lot as a kid as well and I want to be adaptable in my career as well. If I really strongly identify as a print journalist, then that’s all that I will ever do. Maybe that will work. But also, the media landscape is changing a lot and maybe that won’t work, and I think I’ll have a better time with it and enjoy my career more if I can kind of roll with it.

Mario: Yeah. 

Pip: Yeah. I like to keep my options open, I guess.

Hey friends. You’re listening to the Creative Voyage podcast. We’re in the middle of this episode, so it’s time for a short break. If you like this podcast, I’m confident you’re going to enjoy the Creative Voyage Monthly Edit, a newsletter for which every month I ask a different creative professional to curate 10 brief recommendations of cool things to inform and inspire including books, articles, products, portfolios, podcasts, and more, and deliver it exclusively to your inbox. It’s a newsletter curated by creatives for creatives. To sign up, visit creative.voyage/newsletter. Thanks, everyone. Let’s get back to the show.

Every vocation faces its particular difficulties. Recognizing these challenges can help those who are struggling and could be insightful for the ones considering that profession. Here, Pip discussed the main challenges of being a professional writer working today.

Pip: The money is a big one. Also because the industry is changing a lot, it means that stories are becoming shorter and budgets are becoming much tighter and you’re – Like I did last week, you’re writing three a thousand-word pieces in a week. That’s a lot. That’s a lot of writing. I interviewed someone the other day who years ago, like 25 years ago, was a Vogue journalist, and then she went on to become a travel writer and she was saying how like they would have 10,000-word stories. They would spend months researching and contemplating and revising again and again, and you just don’t have that luxury now.

I think that’s part of when I said earlier about you need to be a good writer. You need to be able to produce like sharp, interesting prose, but also you need to be able to turn it around. You can’t sit and contemplate for weeks and weeks, because you won’t make a living. I think one of the challenges is just like the olden days, so I’ve heard, I mean, I didn’t exist, but I guess there was a lot more time to really focus on the writing itself, and that seems to have gone by the wayside.

Another challenge I think is more of an emotional challenge. It’s a solitary profession, and I’m not a solitary person. That in the beginning especially was really difficult. Now I’ve kind of got to used to it and also now live somewhere where people around me speak English, which really helps. In Thailand, there was like an added layer of isolation, because I lived somewhat that felt so foreign and where people didn’t speak English. But now at least, I’m like a creative of habit. I go to the exact same coffee shop every day and order the exact same thing and it’s always the same people there and it just give me a sense of – Like I have created my own office space even though it’s in a café. That’s important for me. I think that’s important for most people.

Another thing I think is really important if you’re going to be a creative is you need to pick yourself up a lot, because other people – You don’t have a boss who’s going to say, “Oh, Pip! Well done. God! You’re fantastic. I’d love to give you a performance review and give you five stars and raise your salary.” You don’t have that. You need to celebrate the victories. I think it’s really important to acknowledge them and celebrate them even if it’s just an e-mail from someone saying, “God! Your piece is brilliant.” Enjoy that moment, because you worked hard for that it might only be a few words, but like that’s what you’re going to get. Yeah, you need to stop and savor that and feel good about yourself. 

Mario: Is there anything else?

Pip: Yeah, also that there’s just no one holding you to account, except yourself. All of these are like a doubled-edged sword. There’s just amazing aspects to that, but it can also feel lonely and solitary and you’re creating your own path, so you don’t necessarily have like a roadmap of exactly where you’re supposed to go.

Mario: Yeah, and there’s a lot of responsibility with that.

Pip: Yeah. 

Mario: And that’s going to be hard. It’s going to be hard to like do that, because often even through education, we’re more trained to abdicate this responsibility in a lot of ways.

Pip: Yeah. I would agree with that. Yeah, you’re really taking ownership of your own path, instead of being in a company that’s sort of like showing you exactly where you’re going to go. That, again, I guess lead back to finances, because you have very different sums of money coming in each month. When I had a job where I was like, “Okay, this is what I get each month,” I was so much more reckless with money because I was like, “Oh! So I’ll just get the same amount next month.” Whereas now, I just have to consider, “Oh! Pension, and what if I don’t have much come in next month and I still need to have money to tag me over,” and you just have to be more responsible, like you said, and be more long-term in the way you think. 

I believe self-development is a crucial factor in long-term career success as well as personal satisfaction, making it one of the central topics of this podcast. Throughout our life, the work we do is a part of an arc, and as professional, we need to manage many various aspects of it. I was curious to hear how Pip is making sure to grow both as a writer and as a freelancer.

Pip: That’s an ongoing process, and I think you can get kind of stuck and complaisant especially if you freelance and you don’t have like a mentor who’s giving you constant feedback. I don’t even know if a mentor exists in a staff job somewhere, but in my mind, there’s like a mentor and always improving you. 

I think the best thing to do is just read the work of great writers, like read The New Yorker. Read New York Times. Read fiction and figure out who you like and which type of style and the voices that resonate with you. Also just look at the way that sentences are put together. If you enjoy an article, like why did you enjoy it so much? Why did you want to keep reading to the end? I think it is inspiring to me to read the work of better writers and think like, “Okay, I got to keep going.” I’m not fully baked yet. 

Mario: For you, I guess it’s a continual process in a way. Are you constantly being or trying to be like mindful of that? 

Pip: Yeah, I think so. I think sometimes I can become aware that I’m getting – I guess I’m just comfortable in what I’m doing and I think that’s what you want to avoid. I think it’s good to take on things that’s still a bit scary, or unknown, or to a pitch a story that’s going to be much longer than you’ve ever written before, or to tackle a subject that’s maybe usually steer clear of. I think it’s good to just keep testing yourself.

Mario: Yeah. 

Pip: You don’t want to get stale.

Mario: When you’re freelancing, or in general, even if you have a creative job, I mean there’re a lot of stuff to do and it’s easy to just spend days, yeah, just kind of like going through a to-do-list or kind of like turning off fires. But then to kind of develop and to go to the next phase and then probably just feel like satisfied, you need to kind of grow and be more like strategic about it. I’m curious, if that’s like a part of your routine, how are you, in a way, like making sure that like besides the job part, you’re also developing both as a writer, but also as a creative professional and just like kind of being more strategic about some of these challenges that are talked about, which you are like aware of, but then it’s also about dealing with them.

Pip: Yeah. I actually don’t think I’m doing that good a job on that front.

Mario: Okay.

Pip: I think that as you were saying that question, I was like, “Oh! We can keep a bit more.” I’ll add that to my never-ending to-do-list. Look, I constantly have ideas of different mediums that I want to explore, of different projects I’d like to do, of different people I’d like to collaborate with. I think that is the best way that I’m going to continue to develop, is that I not only have one of these ideas, but I hold myself accountable and push myself to see it through even if it’s an area that I’m not familiar with.

Also, another thing that has been on my radar for ages and I haven’t done it yet is sign up for a writing course, because I’m not going to get this mentor, but I would really like to have my work critiqued by other people. I think that is the best route for me to do that. That’s another thing that I’ve thought about a lot, is just having one within a week where I commit to something like that. But no, I think honestly, that I could get much more strategic. I think it’s something that I’m becoming more aware of overtime and with experience, but there’s like definitely a long way to go at least in my opinion.

Mario: I’ve been kind of like quite obsessed by that in a way, because I mean, I didn’t have any kind of like hard start, but it really was far from where I am currently and I’ve really kind of – I wasn’t that good at the beginning. I didn’t get like a lot of I think good like solid foundation from my studies. Kind of everything was up to me in that sense. A lot of those things were kind of like constantly in my mind. But it’s kind of funny because even if I am like self-aware of that and working on it, then it’s much harder to actually go through it, because often it’s like, “Okay.” I realize, “Okay, I have to do this and this. I should probably like be better with picking projects and maybe saying no to some and then I have more capacity or I can pursue some better ones.” But then when it gets to it, it’s like that’s where like the bell happens. 

Pip: I completely agree, and it’s really hard to say no to something that’s going to bring in money when you might think, “Okay, but long-term, if I put my energy into this, it might pay off in a different way.” That’s a very hard thing to let an intangible thing win over a tangible sum of money.

Mario: Exactly. As humans, we’re like, yeah, bad at that.

Pip: Yeah, and as a freelancer, then you have to like feast or famine mindset, which I think can translate into this like scarcity mindset what you just constantly think of, “I’ve got to take this. I’ve got to take this, because I don’t know what’s going to come next.” Then I think that goes against that long-term strategic planning that you were talking about where you’re really developing in a more like cohesive way.

Mario: Seth Godin, who is one of my favorite authors and just like teachers, he also teaches a lot about freelancing. I took one of his like online courses about freelancing, which was really helpful and insightful and it’s very much about like strategies and kind of high-level thinking, it sounds about, like how to freelance as a writer or a designer or a photographer. It’s about how to approach freelancing, which was very interesting. 

Pip: Is that a book, did you say?

Mario: No. It’s a course, like on Udemy.

Pip: Oh, okay. Yeah, that’s something that I should do. That’s really – 

Mario: Yeah, it really changed my perspective. I mean, there’s like a lot of interesting kind of nuggets that he shares. One thing to develop as a freelancer, basically you need like better clients. That’s basically one of the challenges of freelancing. Better means like it can be better in a creative sense, but then also better from a financial standpoint and anything else.

Pip: It means so that you can be like more selective about what you take on and then –

Mario: Yeah.

Pip: Yeah.

Mario: Because there is always – Even in like kind of hard times, there are always clients or people who actually have a bit more respect and have more understanding and have more money. Just kind of both like finding them, and that takes time, and that takes a lot of, yeah, strategic thinking and positioning and how you’re like marketing yourself. Basically, it does come to kind of actually taking a part of your time to work on that which I’ve been trying to do, and I think it is helpful. But it is really a challenge.  

Pip: Yeah. I think a large part of that as well is confidence, like that transition that I had to make my mind from, “Oh, I’m sort of doing this,” to “I’m a journalist.” It’s that same mindset where you think, “Well, I am good enough to send a pitch to this editor, or to approach this business. I’ve worked hard enough and I know I’m good enough to do that.” But that you have to have a level of self-belief, I think. 

It’s been said by many thinkers in various iterations; writing helps clarify thoughts. As the author, David McCullough remarked, “Writing is thinking. To write well is to think clearly. That’s why it’s so hard.” Also, writing is becoming an increasing necessary skill needed to participate in a contemporary and ever-connected market. I’ve asked Pip if she had any advice on how we, as creative professionals, can improve our writing skills.

Pip: I think grammar and spelling is just a big thing. So I think trying to keep that as clean as possible goes a long way in terms of making a good impression. If you’re writing that’s more creative, I think as tempting as it is, trying and stay away from clichés. Sometimes you don’t even know that you’re doing a cliché, because they’re so embedded in our consciousness, but try and avoid like those clichés ending or – I remember when I first started writing, I really wanted to wrap everything up with like a witty little one-liner, and sometimes you don’t need to do that. A piece doesn’t need to just go out with this “ba-boomch” moment. 

Mario: Yeah, mic drop.

Pip: Like what? 

Mario: Like a mic drop.

Pip: Yeah, exactly. When I was starting, I really felt like it all needed to end with this kind of like, “Mmm.” That was definitely like something I need to let go off. Also, use thesaurus.com. I spent so much time with thesaurus.com. It’s like don’t let it be like Joey from FRIENDS when he – Do you remember when he writes a letter and thesauruses everything he finds himself off as baby kangaroo? Do you remember that?

Mario: I don’t know. I don’t remember that actually.

Pip: You want to know what the words mean that you’re putting in, but I think it helps a lot, because otherwise, I can get a bit stop using the same adjective, for example, and that can make my writing – It can just feel a bit samey after a while. So use the tools out there on the Internet. Check your grammar. Expand your vocabulary.

From discussing the paradoxes of intimacy with the world-renowned psychotherapist, Esther Perel, to understanding the rise of virtual boyfriends, Pip places her subjects at the heart of her stories. In the domain of long-form profiles, she contributed extensively to The Kinfolk Entrepreneur, a collection of interviews with today’s creative class. Undoubtedly, she’s a master of her craft. Somewhat selfishly, I’ve asked Pip to share what for her makes a good interview and if she had any specific interview practices or tips. 

Pip: When I feel really satisfied by an interview, it will be because I feel like that person and I have connected. I’ll feel like we could go out for lunch the next day and have a really nice time together and have lots to talk about and they would feel comfortable in my company and I would feel comfortable in theirs. I would feel like we have managed to establish a bond and enjoy one another’s company. 

I think – I mean, selfishly for me, I want – If I’m going to speak to someone for an hour, I want to enjoy that and I want them to feel relaxed, because if they feel relaxed and comfortable around me, then they’re going to open up a lot more and reveal who they are. Yeah, it’s a really great feeling to end a call and walk away from it thinking, I’ve just really liked getting to know that person.

Mario: My next question, which naturally goes from there. You have a lot of experience with it. I’m curious like kind of how you achieved that? What would be like your interview tips? I’m sure like it’s something just like serendipity and you can’t do much about it, but I’m sure there’re also some steps or processes that you can do to at least try to make sure it goes the way you want it.

Pip: Well, I think naturally, I’m just an interrogator. I love questioning people. I love finding out about them. If I go to a dinner party and I’m sat next to someone that I’ve never met before, I’m going to know their entire life story, like devastating breakup of the last 5 years, lost in the family. I would know it all by the end. I’ve always been like that. 

It definitely helps if you are an interrogator. But I think there are other things you can do even if you’re not naturally like that. I do my research. So you want to go into an interview having an idea of this person and their work and things have said before in other interviews. I try and make my questions a bit offbeat, I guess. I don’t want them to just be questions that are going to be produce quite short matter-of-fact answers.

You want to open up a conversation where that person can segue into an anecdote from their life, or an interesting thought they had the other day or something that frustrated them. You want it to feel personal. If you just go into it with a kind of chronological approach, let’s say, you’re going to get pretty matter-of-fact answers. Then that makes it so much harder to write, because you don’t have any of those quotes that really like show you who a person is.

One thing that I read this somewhere is there’s an interview with a journalist and I remember thinking, “Yeah, that’s really good advice,” is just like resist the urge to butt in, which is so hard when someone says something that’s really – I think we all have that instinct to be like, “Yeah, I know what you mean,” or “It reminds me of this.” But if you can try and sit back and let them explore their idea, that can also just reveal more of a person or take it in a direction that is a bit more unexpected.

I think, finally, sometimes, not always. It kind of depends on the person and the conversation that we’re having, but sometimes is I feel like it’s appropriate, then I’ll – when they tell something, I’ll say, “Oh, you know. That’s like this experience I had recently. Then it can feel like more of a back and forth conversation rather than me interrogating them for answers. Yeah, it can just make it feel more friendly.

Mario: When you make like an interview for, let’s say, Kinfolk or some other publication, do you have like a similar process for it?

Pip: I’ll research them before. Jot down key facts and then I’ll have a list of questions. I guess, I must have some idea of where I want the piece to go, because my questions, they must be driving that. But I also just think like – I don’t know. What would I like to ask this person? What do I think is interesting? It doesn’t necessarily have to be directly related to their work. I think it’s really – Again, this is something that I just, again, really am interested in, but I think it’s really interesting to make sure that I approach things from how they feel or what they think about something rather than just how it happened.

Then I don’t – Yeah, I probably interview people between 30 minutes and an hour depending on how long the piece is, depending on how much we have to say to one another.  Then I transcribe it, and that’s a painful process. I know there’s a million different piece of technology you can use, but I do think it’s helpful to sit and listen again to what’s been said. When you’re having a conversation with someone, you don’t always pick up on like the nuances. Then when you just move back through things can stand out that didn’t the first time around. Yeah, I stop putting quotes that I think are really interesting in one place and take it from there. 

At this point in our conversation, I was curious to hear what are Pip’s current professional challenges. Here’s what she shared with me.

Pip: I think right now, I’m struggling the most with balancing work with the baby. It’s a pretty obvious struggle if you’ve got a 6-months-old baby. But it can feel difficult to sit it all in, and I’ve got standards and expectations for myself, and I don’t want those too less, or I don’t want to hand something in late, or do it in a rushed way. It’s maintaining the standards that I have for myself with a lot less time, a lot less freedom and spontaneity at the minute and a lot less sleep. That’s just a huge life change.

Then as we were talking about earlier, I think another broader challenge is just, yeah, what does this grow into? How do I keep getting better? How do I stay excited and engaged? It all comes from me. There are some days where I feel really energized and excited and I’m just this boss bitch doing as I want, and then there other days where it’s like, “I don’t know. I don’t have any ideas. Can someone else tell me what to do?”

Yeah, I’m sure you can relate. Those are the days where you just think like, “This sucks, and I want structure, and I want a set amount of money coming in each month, and I want this, that and the other.”  I think, yeah, those are the two things that I’m dealing with right now and that I’m going to continue. Those aren’t going to go away. It’s just figuring out how to make the most out of my work and out of my skills and really appreciating the great moments.

Mario: Yeah, exactly. I think that’s really crucial, because if you’re a freelancer for a couple of years and you’re managing that and you’re sustaining that, but in a creative way and financially, that means you’re quite driven. It’s hard to pull it off you’re not like driven and pushing. But with that type of approach or personality, it’s also, yeah, easy to not be grateful or not have those like little celebrations that you mentioned earlier.

Pip: Actually, I know a freelance journalist in Jerusalem covers news in politics. I was umming and ahing about getting a personal trainer after I’ve had the baby, but it’s so expensive and I’ve always done yoga, so I’ve always practiced by myself, or if I want to do like cardio workout, then I’ll find a YouTube video and I’ll do that by myself, and it’s always been self-motivated and disciplined with that as well as everything else. I was speaking to this friend and she’s like, “Yeah. You know what? I freelance all day and I have to be completely self-motivated. I just get a personal trainer, because that is one aspect of my life that I don’t want to have to also be really disciplined about.” I was like, “You know what? That is so true.” 

I think you should – If you can stretch to it with things like that now and again, I think it can be really good to handover some of the motivation into someone else and just say, “What? Once a week, I want you to come and tell me what to do rather than me having to find the mental strength to get up and do this.”

Mario: Sounds like a good way to get some balance. Yeah.

Pip: Yeah. Actually, since I started seeing him, it’s not even once a week. It probably is less than that, but it has been kick-started me to the rest of the week doing my own thing. But some of you just need that push from someone else.

We’ve come to the very end of the conversation I had with Pip, and as with previous guests, I’ve asked her to highlight three parting pieces of advice based on what she experienced so far on her professional journey.

Pip: Tip number one would be to treat each piece of work seriously. Even if it’s something that you don’t feel very invested in, or maybe it’s not your greatest passion and life goal to write about it, you need to treat it with care and do your best on it, because you never know where something will lead or who will see it. I think it’s really important to have that basic standard for yourself.

Secondly, I think you need to read the work of writers that you respect so that you don’t get complacent and you remember that there are people much better than you out there, and I think that can feel discouraging, but that can also feel really encouraging, because it’s a journey and it’s exciting to do something which you can continue to get better at.

Finally, I think it’s important to know your value. So that means asking for higher fees, pushing back on contracts and just generally treating your work as a business as well as something creative, because it’s your livelihood and you need to treat it as such.

Hey, everyone. That’s it for this episode. I hope you find it useful, and if you like this podcast, tell a friend. I want to thank Pip for coming on to the show. She’s an incredibly talented writer and I’m grateful for her sincerity and all the practical insights she shared.

Links to Pip’s work as well as some others mentioned during the conversation can be found in the show notes at creative.voyage/podcast. Also, you can follow @creative.voyage on Instagram, join The Monthly Edit newsletter, and if you haven’t already, be sure to subscribe. Until next time my friends. Take care.