The best books on Creating a Career You Love

You’ve become a poster girl for the portfolio career—running a prominent blog, the popular podcast Ctrl Alt Delete and a consultancy. So what are the benefits of that kind of lifestyle, and are there drawbacks?

Yes, there are drawbacks. But there are a lot of positives, and I would never ever swap what I’m doing now for the way things were. The positives 100% outweigh the negatives.

I love the fact that I can work whenever I want. I don’t have to ask anyone’s permission to do anything. I can design my week from scratch. Monday to Sunday is a blank canvas for me. There’s no society rulebook telling me how I should work.

One drawback, though, is you can end up working around the clock. You don’t even know what work is anymore, because it’s turned into your life. You can burn out pretty badly without even realising. So, even though I didn’t like working a nine-to-five, there are definitely positives to having that time ring-fenced. There are just different obstacles that come up, I suppose.

The Multi-Hyphen Method, your bestselling business advice book, is aimed at people hoping to turn their passions into sources of income. Could you tell me how your own experiences fed into the book?

Yes. I suppose The Multi-Hyphen Method came from a necessity, which is the fact that two of the magazines I used to work for folded. It’s a very scary time to be in the media publishing world; in terms of print and digital, it seems like everything is up in the air and a lot of models aren’t working, which is really sad. That’s one side of things.

The other side of things is that it’s a lifestyle choice as well: you can want to be a ‘multi-hyphen’ and not get forced into it. You can choose that way of life, which is something that a lot of people do. I interview people in the book who I find really inspiring. One was a nurse and children’s author; another is a podcaster and a chef. Another is a pilot and a photographer. We are allowed to define ourselves how we wish.

What happened with me is I always had the full-time, shiny job on paper. I had a good salary, looked good on my LinkedIn. I did all the right things that I was told to do at university and school. I just realised that I should try to protect myself as much as possible by having side projects—multiple income streams. I was passionate about that from the very beginning, because we’re in a time where anyone can be made redundant. The job for life doesn’t exist any more. We don’t have the security of knowing we can work for the same company for ten years.

So my side projects were a necessity, but also fun. In the end they were my absolute lifeline.

You wrote recently about how you have managed to leave behind that nagging sense of duty—of doing what you felt you ‘should’ be doing: “Self-employment has allowed me to rid myself so many shoulds.” The books you’ve chosen seem to return again and again to this idea of figuring out what you want to do, rather than what you feel you should do, and building a career from there. Do you agree?

Definitely. I think that there are a lot of shoulds in life. I don’t want to generalize, but I think that women especially can be made to feel grateful for a lot of things in life. That we should just be grateful to have a job, that we should be grateful if we are getting paid a little bit more. There are so many things said about how, at investment meetings, men pitch the business that they want to build, whereas women often pitch the businesses they’ve already built. It’s like we have to start from a higher place to be taken seriously. And of course it’s even often even harder for people of colour.

We go to school and are told that there’s this magical ladder waiting for us at the end. We climb this ladder at school, then climb this ladder at college or university . . . but then we’re on a cliff edge, and no one tells us where the next ladder is. I don’t think that ladder exists anymore. We have to design our own careers now.

I didn’t make this rule up. I don’t always love that this is the way that it is. I would love to work in a job that had my back and gave me security, but sadly, it doesn’t feel like they exist anymore. I don’t think they do have our best interests at heart. So I wanted to write a book that inspires people to keep on learning, and to not expect companies to train us up anymore.

The internet really empowers us to do that. That means teaching yourself the basics. That means YouTube tutorials. That means starting a side project. Going to some sort of a workshop, or downloading a free webinar, or listening to podcasts, or going on Skillshare. There’s so much out there—there’s so much out there for free—that actually, we should feel like we can do anything because the world is so up in the air.

Let’s have a look at the books you want to recommend. The first book choice is Linchpin by Seth Godin—or, you added, “any book by Godin.” Why is he so inspiring?

Whenever I’m feeling a bit out of my depth and overwhelmed and confused—which is a lot of the time—Seth really inspires me to go back to basics. We are so overwhelmed at the moment with possibility and choice and options. Because the internet has opened our world up so much, we have so many options that can lead to confusion about what we want with our lives. That’s the downside of the multi-hyphen method, to be honest: we are constantly looking around to what other people are doing.

Seth goes back to the core: what do you want to make, why do you want to make it, who do you want to reach, and what is this for? Instead of the other way around, the temptation of immediately longing for the end result, which is often about glory or fame or social media followers. What do you actually want behind all of that?

Another thing I love about him is that he inspires me to start new projects, because he really believes that we just need a small audience. We don’t need a million followers on Instagram to be successful. He says we need 1,000 people to believe in our idea at the very beginning, which sounds like a lot of people but over time that’s quite easy to reach online. He believes in starting really small, and that’s something I believe too. We should always start small, and if it starts taking off, then invest. Don’t spend all your money on the latest equipment to start your new shiny project, only to realise it’s not working. I think we have to make sure that we start planting a very small seed and seeing what happens.

Yes, that makes sense. This particular title, Linchpin, focuses on making yourself ‘indispensable’ to a workplace. It sounds quite a defensive way to think about a job—anticipating the fact that you could lose it. But maybe that’s necessary, given what you said earlier about job insecurity.

Linchpin is his most famous book and therefore has received the most attention, but it’s also quite divisive. It might seem outdated, but I believe that we can all make ourselves indispensable. We are all human, and are all quite unique in our offering. I think that the workplace made us feel like we had to be machines. We had to turn ourselves on at 9 am; we had to turn ourselves off 5 pm; we had to work when someone told us to work. In the future, robots will take over the jobs we used to do, so being human in the workplace is becoming more of an asset than it was before. It allows us to be ourselves; it allows us to be a parent in the workplace and be honest about that, not have to lie about it and then leave the office feeling rubbish about ourselves. It means that we can kind of be open about our identity, our background, our orientation in all sorts of different ways. Why can’t we bring our human aspects to work?

That’s kind of how I see Linchpin: it’s just about celebrating how we’re all different and our actions matter.

I worked for a while as a junior in a competitive office where a mentor gave me the opposite advice. He said: “Don’t become too useful in your current role, or you’ll never be promoted out of it.” Is that a flaw in the linchpin argument?

Well, that is true. I’m taking the Linchpin approach and moulding it to my own, if that makes sense. I do this quite a lot with books. I take an idea and kind of rejig it in my head. He is talking about working in an office, and obviously I don’t work in an office. I think being a linchpin is making sure you are useful and able to work your way up. If you keep on learning and educating yourself and being a source of knowledge for others, your bosses or clients won’t want to keep you squashed down because you’ll be able to bring so much more to the table in higher positions.

You mentioned earlier that he makes the point that the education system doesn’t prepare us well for the working world. Could you expand on that?

Yes. He says that the education system as it stands is really quite outdated. He thinks that school just prepares you to be obedient, and obedience isn’t a metric of success anymore. Being obedient used to get you promotions, it used to get you pay rises—because being obedient just means following the rules and sitting at your desk until midnight.

But success (for me) doesn’t mean following the rules any more. It means the complete opposite. It means rebelling in some way. Every single good thing that’s come off the back of my career is from rebelling. It is scary, but I think it’s needed, especially at the moment we’re at in the world. We don’t need more people just following the rules, I think.

Absolutely. I really relate to that. I was a very obedient child at school and then again in my early career. But I’ve spent my working life learning not to be so biddable. Maybe we could move onto your second choice, The Artist’s Way: A Course in Discovering and Recovering Your Creative Self. What impact has this book had on you?

I absolutely love this book. It cuts to the core and truth of why people have a side hustle.

Personally, I don’t mind the phrase side hustle, although I think it’s quite American. I think it’s a phrase that just got trendy. I never called my side projects a side hustle, ever, until the last few years when, let’s be honest, my publisher probably thought, ‘Oh, that’s a good word to get us some more press.’ But really, at the heart of it, for me, my projects were passion projects. They were things that kept me sane.

The blog that I started about eight years ago, it’s now a side hustle—because I made money from it in the end. But really that blog was . . . you know, I’d get home, my soul felt shrunk to the size of a raisin, and writing that blog was a way of me genuinely living my life and not feeling so miserable. It kept some joy in my life, and reminded me that actually, maybe I can write. Even if no one reads it, I can still just get something from writing. I think everyone should have something that’s just for them. Whether or not you monetise it is up to you.

“At the heart of it, for me, my projects were passion projects. They were things that kept me sane”

The Artist’s Way is for anyone who thinks: ‘I want to have a side project, but I wonder what that would be.’ It’s a really good starting point to discover what lights you up. It could be anything. It could be gardening; it could be ice skating; it could be writing poems. There are two things—tools, or practices—that Julia Cameron recommends.

One of them is ‘morning pages,’ which is when you wake up—before you check your phone, before you make a cup of tea, before you look out of the window, before you do anything—write three pages. It can be anything (I mean, it’s normally rubbish because it’s just your brain filtering), but it gets your creative juices going for the day.

Then, the second thing she calls an ‘artist’s date.’ Basically, once a month, you take yourself out on a date. I know it sounds a little bit cheesy, but all it means is take yourself off to a coffee shop for the afternoon and treat it as just your time to read or write or think or listen to music. She basically says you will come up with an incredible idea being on your own, thinking—it won’t take long. I love it, and it’s true: you do.

Instead of reading all these fast paced books saying: ‘Here’s how to be amazing, here’s how to get a side hustle, here’s how to hustle, hustle, hustle.’ This is the total opposite. It’s about slowing right down and connecting with yourself again.

This reminds me of a word you hear a lot in creative writing circles. Many people—women, particularly—say that they need to give themselves ‘permission’ to write, or spend time on creative practices. To spend time on something that’s not immediately, tangibly productive—money-making or otherwise useful.

Yes, and maybe that comes from a level of guilt. It’s always bottom of the list, you know. There’s helping others, doing the laundry, work, and then right at the very bottom, maybe there’s some time for you. I definitely think that is true for many people.

Elizabeth Gilbert’s book Big Magic was another really inspiring read for me, because she talks a lot about permission. I think confidence and permission are kind of linked, because it almost feels arrogant to say, ‘I think I’m creative,’ or, ‘I think I can write.’ There’s something in there that wants you to squash that and tell yourself you’re rubbish and that you can’t.

“Asking for reassurance is pointless. Other people’s reassurances just don’t stick”

There is a level of permission, and that takes us back to Seth Godin quickly. I interviewed him on my podcast last year and something he said really stuck with me, and actually changed the way that I approach things. He said that asking for reassurance is pointless. That reassurance is something that fades instantly in a human mind. If I say to you: “Do you think I can do it, do you think I could maybe write this next book?” You say, “Yeah, yeah, I think you can.” But it just vanishes. What you really need to do is give yourself reassurance, because other people’s reassurance just doesn’t stick.

I was someone who always asked for reassurance, and actually now starting a project without hearing you can do it from random strangers is really empowering.

Your next book is not one I’d come across before, but it sounds incredibly useful. Can you tell me about The Decision Book?

Oh, it’s so good. I guess it goes back to what I was saying before—about how there’s so much choice now, and this is, I guess, a criticism of a portfolio life, that we can do too many wrong things at once. Why does anyone want to add something else on? We’re busy enough. Why do you want us to work more?

I get it—multi-hyphen life can sound like more. It sounds complicated. It sounds stressful. It sounds like you’re piling stuff onto me. But that is 100% not what the book is: it’s saying if you want to do multiple things and have multiple strands in your life and not have one career, here’s how, and here’s how to streamline that. Here’s how to do less. The multi-hyphen method isn’t about multi-tasking—it’s about picking a few things to do well.

The Decision Book is one that I come back to a lot. I’ll just explain one page from it that I always come back to. There’s this graph with two axes: importance and urgency. It splits the page into four areas: urgent and important; important but not urgent; urgent but not important; and not important, not urgent.

Sorry if that sounds complicated, but for so long I didn’t see the difference between urgent and important. I looked at my to-do list in completely the wrong way. It really has encouraged me to understand there are things you can just do immediately—like an email that takes two seconds; things that you can delegate; and things that you can just do later, even a week later. I think that’s the problem with living in this modern world where people think if you haven’t replied to an email in three hours then you’re dead. There’s no room for taking some time.

It’s an amazing book. If you are confused by how to get through the day with your multiple projects, it tells you how to prioritise your day. It’s incredible.

The models presented in this book are taught to MBA students. Have you ever thought about studying business?

I don’t really believe in it, no. For me, a lot comes from getting your hands dirty and jumping in the deep end. I don’t think there’s anything you can learn out of business school that you can’t learn from doing it yourself and maybe getting it wrong a few times. I’ve always been that person who really struggled with academia. It never really stuck in my head. I don’t know whether that’s because I’m a visual person or because I remember things when I hear them said out loud, or maybe I am just like better in real-life situations than in hypothetical situations.

But I also believe that you don’t need to spend money on courses to be successful. That, to me, says that maybe there can be some sort of fairness in this industry. That you can come up with a brilliant idea and execute it and reach millions of people without having to have money, and spend it on a degree. Maybe it’s wishful thinking, that I just like the idea of everyone having a fair go. But I actually think that a lot of people are better at just rolling up their sleeves and getting on with it.

Your next choice tackles an important issue for the internet generation: How to Not Always Be Working by Marlee Grace. I’ve been thinking of it as a kind of manual for avoiding burnout. Is that a fair characterisation?

Yes. It’s a really sweet little book. It’s pocket-sized. It’s pastel pink. But it’s also funny.

I think it taps into this weird problem we’ve got at the moment. Maybe it’s millennials, maybe it’s everyone, but we feel so guilty when we’re not working. It’s almost a good problem to have in the world, isn’t it? That we’re all obsessed with working. The opposite would be a problem, wouldn’t it, if no one wanted to ever do any work.

It feels like we’re full of an incredible energy at the moment. Young people want to be activists; they want to do things for the world. And it feels like there’s a nervous energy around taking time off. That’s something that always comes up in Q&As. People will say: “I feel guilty when I’m not working.”

“This is something that always comes up in Q&As: people feel guilty when they’re not working”

This book is really great. It’s quite practical but it’s also written in a kind of memoir style. One of the exercises is the most basic thing ever, but it’s one of those things where you realise, ‘Oh, I’ve never actually done this before.’ To do it, you write down what ‘work’ is, and you write down all the things that aren’t work.

Then you have these crossovers, the grey area of what could be work. For example, going on Twitter. That’s work, but it’s kind of fun, so is it? Basically, you make three lists, and the not-work is stuff like having a bath, going for a walk, eating your dinner, talking to a friend. It’s amazing just how many of them cross over, but the ones that don’t are really crucial for self-care, and if you’re not doing them on a daily basis, then you need to make more time for them.

Yeah, I love it. I love this little book.

Ann Friedman, a writer I know you admire, recently made a similar point: “Don’t treat yourself worse than you’d expect your employer to.”

Oh my god, that’s so true.

Are you guilty of this yourself?

Yeah, I mean it’s such a difficult one because what’s so amazing about being self-employed is that every single gain you make is yours to keep. Everything goes into the pocket of the business that you own, so those Sunday nights I stay up until midnight working on a project—they are never going to be the same as if someone else is barking orders at me, making me do it. Because that kind of big project might allow me to go on a massive holiday or take time off. The choices are ultimately mine, so it never feels as bad. But it’s true. We should be kind to ourselves.

There’s another very simple thing: sometimes I listen to the way I speak to my friends and think, ‘I should speak to myself in the way I speak to my friends.’ Because I am kinder to my friends than I am to myself sometimes. Because I don’t think I do that enough.

I agree.

The other myth, I will say, is that I do think that being your own boss has been romanticised. It’s not true that you don’t have a boss. You do. You’ve always got bosses—you just have them for shorter periods of time. You always have clients, people that you have to please and work hard for. I do think there are some sides of self-employment that people love to put on a t-shirt or put on a mug and glamorise. It’s not always the case.

In an interview you gave to the Huffington Post you said, “People probably think I’m physically working more than I am, because I’m constantly posting or appear on, but I schedule content online. I plan ahead. I bulk record. I outsource. I plan and schedule emails.” Do you have any other general tips for people looking to work more productively?

What I was getting at with ‘bulk recording’ is that the more that you can do of the same task in one go, the better. Even—and I’m not saying I’m perfect and I stick to this all the time, but still—only doing your emails in the morning and at night. Well, not night, but maybe 5 pm. That has changed everything for me. We shouldn’t feel like we have to be at the beck and call of everyone else all day long. As an author called Tom Chatfield wrote, “your inbox is a to-do list written by someone else.” It is something that I try and do, and although I know that not everyone can, it’s good to keep the day as free as you possibly can.

What else? One thing that is important is really, really planning ahead. Making sure that you are always at least one step ahead. For example, with my podcast, I plan that around a month in advance and I make sure all the content is up and ready. Much like a magazine would or any company plans ahead—I don’t think you should ever feel like if you’re self-employed then you shouldn’t stick to those things. Because what if you get ill? What if something happens? It’s really important to make sure that you aren’t chasing your tail, because we just don’t know what’s around the corner.

At the end of the day when you work for yourself, you need to look after yourself. I think planning ahead is something that makes me feel much more in control.

Let’s look at your final book choice. My Creative (Side) Business by Monika Kanokova, a guide to setting up creative freelance businesses. She raised money for this book on Kickstarter. Is this important—for entrepreneurs to be always looking for new, different ways to finance projects and their life?

Yeah. I really like this book. It doesn’t look like a book that’s been self-published, if that makes sense. It’s really, really brilliant. I think it’s an interesting time for self-publishing because you can make the same amount of money as in traditional publishing.

There’s a project that’s just won an award in the UK called The Pound Project. Basically it’s a model like Kickstarter, where you pledge a pound for a book. Fine, it’s only a pound. But what happens is so many people put money in because ‘it’s only a pound’ that a book recently raised £12,000 in a few weeks.

That’s not actually that far from, say, an unknown debut author’s advance. So it’s an interesting time: if you can get the right editors and the right marketing team, who’s to say you can’t put an idea out that is just as valuable, and just as good? I really think Monika is someone who has done self-publishing brilliantly. Not to say she might not do it more traditionally in the future.

“It’s an interesting time for self-publishing because you can make the same amount of money as in traditional publishing”

What I like about this book is that has lots of interviews with people who have made their side businesses into their main business. They’re not famous people. I think, and I’m probably guilty of this because I interview a lot of well-known people on my podcast, that there are so many lessons to be learnt from people who aren’t always shouting about it, or sitting on social media every day.

This book has really opened my eyes, and I’ve discovered so many interesting people who do interesting jobs. It’s full of tips, and I love books that have interviews. It’s quite meaty, this book. There’s a lot in there. There are chapters on building multiple income streams and passive income.

We mentioned that word ‘hustle’ earlier. Do you think that being the kind of person who hustles is a necessity?

When I look back at the last decade or so, there are times where it’s been so hard because I’ve had a full-time job and was trying to make a side business. That is quite horrific in terms of time spent working. But I think it’s the antidote to the ‘quit your job and follow your dreams’ narrative, which I don’t like. I could never have quit my job. There was no way in a million years I could just have quit my job to start my side business.

It’s about transition, doing both for a bit, and saving enough money by doing both that you can then slowly do less of the full-time job and jump across. I mean, that’s the strategy that seems to have worked for a lot of people in this book; there’s always a crossover point when you feel like you’re going to burn out. But then, without that bit you don’t get to reap the reward.

Every single interview is so different, and I guess maybe that’s the point of the book. There isn’t only one way to do any of this. So many books say ‘here are the three steps to make your life easier.’ But there’s no such thing as an overnight success. I get frustrated by that approach—sometimes when I’m doing events it’s almost like people are sat there with their notepad and pen like, ‘just tell me in one word how I can be successful.’ Or, ‘tell me in one short sentence what the answer is.’

The answer is that you keep going and over time, build something. This can take a year, or years, to kind of get right. Everyone in this book has learnt by doing. I think that we like to reward starting things in society: it’s very easy to caption an Instagram post, “I’m starting this side business.” You get all the likes. Or even when people get engaged—people love people getting engaged! We want to reward people who are starting things.

Then what happens, I think, is you get such a buzz from telling people ‘I’ve started my novel’ that you end up not really finishing it. I love this book, but it’s very granular and it’s not romantic, and some of it is kind of boring. Some of it is talking about finances and how to save, how to do a spreadsheet so you know exactly how much money you need each month, because maybe you’re reaching burnout and you need to turn down a project. Can you afford to say no? How do you not go mad when you’re spending so much time on your own? It’s all these things. They’re hard, and it’s hard to keep going.

Before we finish—what would you say to someone feeling burnt out or trapped in a job they don’t like? Where should they start?

Well, this is why I’m so passionate about flexible working. What happens is that we feel so trapped and we feel so tired and we feel so exhausted when we have a full-time job, because when you don’t like something your mental energy is being used up. You’re spending so much time and energy hating it and being upset and exhausted and frustrated that when you get home, the last thing you want to do is work on a side project. But it’s about flipping that narrative: the side project will be your saviour.

In my book, I wrote about how nurses have actually prescribed to patients to go do something artistic as a way to try and help some of the mental health problems that they’ve been going through. We all need something that we can get lost in. Finding the time shouldn’t be seen as a chore. It should be seen as the opposite.

This is why I really want a lot of people and a lot of companies to kind of take on the four-day week. I think the world would be a better place if everyone had one day or even one afternoon to use their time in a way that might help themselves or the world.

Sometimes people act like I sound crazy when I suggest that. I feel like we’re so ingrained in the way things have always been done, that making any suggestions on how to do it differently is just met by, ‘no, we can’t do that, that’s not the way it’s been done.’ But I don’t think that it’s crazy to think that more people should have more time to be happier.