Podcast 3: An Introduction to Freelancing

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Welcome to the third episode of the HomeWorkingClub podcast, where we provide an introduction to freelancing and candidly discuss all the pros and cons. 

You have the option of listening to the podcast, or reading a full transcript below.

After discussing how remote working works last week, today we focus on the alternative, which involves working entirely for yourself. Our introduction to freelancing celebrates the freedom and variety that this brings, but doesn’t shy away from some of the more grim realties, such as enduring the “feast and famine” of inconsistent income.

Freelancing is a lifestyle choice, and for many people it’s a way to truly work to live and not live to work. This podcast will be of particular interest to anybody who likes the idea of a location independent lifestyle. With no boss to answer to and rules to follow, you really can go and work from anywhere.

Included in this podcast:

  • What is freelancing? (0:31).
  • Why we love freelancing (1:42).
  • The downsides of freelancing (4:40).
  • Dealing with social isolation (7:44).
  • More on the plusses of freelancing (9:51).
  • How to get started in freelancing (11:05).
  • The importance of ongoing training and learning (15:40).
  • Why you mustn’t become your own “horrible boss” (17:10).
  • Why networking is so important (20:08)

Supplementary Links and Information 

An Introduction to Freelancing: Full Transcription

Please note that some repeat words or unclear passages have been edited to enhance readability.

ALEX: Welcome to the HomeWorkingClub podcast. I’m Alex.

BEN: And I’m Ben.

ALEX: Hello again. Today we are talking about freelancing. Why we love freelancing, some of the downsides, and how to get started.

So, in traditional style, Ben try very hard to pretend I’m an idiot and tell me what freelancing is.

BEN: Okay, well, freelancing is working entirely for yourself. So being self-employed, doing work for multiple, different clients. I would emphasise that when I talk about freelancing I do mean doing work for several different clients.

I think some people do think freelancing could mean just working self-employed for a single client. I would call that contracting. That’s not really genuine freelancing.

So… building up a business, doing whatever it is you do, be it writing, IT consultancy, web development, design. Any one of those things or even more than one of those things.

ALEX: That’s an interesting point, actually, you said building up a business. Is it really helpful to think of yourself as a business?

BEN: I think so. I think it’s also… by taking that mindset, I think you’re more likely to succeed, rather than just thinking “Right, I am a freelance writer”, for example. You’re almost closing off other opportunities.

If you’re a freelancer, and I think that’s what’s so exciting about it, you can literally do whatever you want. Any services that you have got good experience in, anything that you’re good at, you can find someone who wants to buy those services and you are off and away.

ALEX: Fantastic. So anybody that’s even spent five minutes on Home Working Club will know that you are a massive fan of being a freelancer.

BEN: I am. Yes, it suits my lifestyle a lot. Having worked for myself since 2004, I believe… wow over 15 years! I wouldn’t want to, despite the downsides which we are going to talk about, I wouldn’t want it any other way. I do like this lifestyle.

ALEX: Excellent stuff. So what particularly is it that recommends it to you?

BEN: Well, I mean, last week I was doing my work in the Canary Islands! Which, not meaning to brag or anything, but I mean, that is something that is just truly wonderful! Being able to pick up and do my work wherever I want. But I also love the fact that I am at home when my young sons get in from school every day. I do work in my PJs sometimes… well, probably more than sometimes.

ALEX: I would like to report that Ben is not wearing pyjamas today.

BEN: No, fully clothed, always fully clothed for the podcast.

I like being my own boss. I’ve never had to say I can’t go to a Nativity play or I can’t go to a parents evening or anything like that. It feels so alien to me when I speak to friends now and they say “Oh, I’ll have to see if I can get the time off”. I think, “What’s that about?”

You almost forget. You become so conditioned to being completely in charge of what you do. It’s a wonderful thing! I can’t imagine having to ask permission for such things as seeing key moments in my children’s lives.

ALEX: Yeah, I think that’s what hits a lot of people: no more boss, no more company, no more politics.

BEN: Although, I think I should probably say that the clients do become your boss to an extent. I think, certainly more so in the early days as well, because you’ve got to keep those clients happy. So sometimes it can feel like instead of having one boss, you’ve got five. But I think that the longer you do it…

I like to encourage people to form partnerships with clients rather than kind of boss-employee style relationships. And I think the more that you end up working with clients that do feel like partners, yes, it does feel like you don’t really have a boss.

ALEX: That’s interesting. Hitting on that point, I suppose a lot of people freelancing will have that client relationship. But then again, I suppose some people are in a situation where they are actually just doing their own thing. So you know, if you’re just completely creating your own work and you’re working for yourself, there’s a difference there that perhaps it isn’t going to be the complete freedom that you might initially think.

BEN: No, it´s not. Another thing that I like to encourage…for example….Home Working Club is entirely my own project, no boss at all. But then this afternoon, when we finish recording these podcasts, I’ve got a couple of articles to finish for a client.

That’s obviously leaning a little bit more to having a boss because, believe me, if I don’t hit that deadline there will be some trouble involved. But obviously, that client and the other clients do know that they are buying my time and they’re buying my output, they’re not buying my soul. Which it can feel a lot more like when you’re an employee, even a home-based employee.

ALEX: Well, before we get into the full metaphysical range of what it’s like to be freelancing. What are the downsides?

BEN: The big one: feast or famine. Now, I know a lot of people who went through some famine last year. The annoying thing with it is that it always, I mean any conversation I have with any freelancer always seems to have the same theme, you’re either super, super busy or everything is dead and you’re worrying about how to pay the bills.

I would love to say that after years and years of doing it, that goes away, and I think yes, it lessens but… it’s either stupid busy or stupid quiet. You really do have to learn to tolerate and withstand those peaks and troughs without getting into a huge panic about it.

ALEX: I suppose part of the skill as well is actually preparing for the fact that it’s not always gonna be amazing and stuff coming through the door all the time, and actually working out how you deal with those fallow periods a little bit more.

BEN: Very much so. I think it’s also coping with the busy periods as well because you have to make hay while the sun shines. So, I think that what I try to do is enjoy the quiet bits. Hard though that is when it means that your income has dropped because if you don’t enjoy those quiet bits and get out and sit in the garden more and go for a walk more and things like that, you’re not gonna have time to do it when it does get busy.

And when it does get busy… my wife’s good example here, she’s a freelancer as well. She can either be quiet or she’s sitting up in bed working in the evenings because when the work does come piling in, you don’t really want to turn it away. And it would be lovely to say I’m a freelancer and I’m gonna religiously work 35 hours a week. It doesn’t work like that.

ALEX: Yeah.

BEN: So that’s a big, big downside. Different people have a different level of tolerance for that, as well.

The other one I would say is, on a personal level, that there’s a lot of bureaucracy and a lot of paperwork that you have to do. Things like… I think employees don’t necessarily realise how much is going on behind the scenes about, taxation and benefits and all that kind of stuff.

And you’re dealing with all of that yourself and responsible for your own tax returns and dealing with accountants and things like that. I think that what a lot of people don’t realise to start with is that all that stuff takes time and you don’t earn any money while you’re doing it. So, they’re probably the biggest downsides for me.

ALEX: There is a very good reason why a lot of freelancers are accountants, or rather, a lot of accountants are freelancers. There’s always lots of work for them!

BEN: One that’s not really a downside for me, but I think is a downside that I should mention is just managing time and managing your own motivation. If you think in your heart of hearts that you’re going to struggle to self motivate and that you’re going to switch the TV on and not get work done and you’re going to procrastinate a lot, freelancing might not be great for you because no-one’s going to be there, other than clients if you´re missing deadlines.

No-one’s actually going to be in your ear pushing you along and keeping that motivation, that energy level up. It’s not really that much of a problem for me personally, but I know that it certainly is a problem for a lot of people who I hear from.

ALEX: What about isolation? Because I think it’s brilliant. I certainly feel that when I’ve been in a full-time office environment, the idea of being able to be my own boss and not be part of that structure has felt incredibly liberating.

But also what about that fact that, actually, after a while, if you’re not seeing people, you don’t perhaps… something crazy, like 1/4 of people meet their partners through their work. That kind of thing. How do you replace that?

BEN: I do think you need to work hard to replace it. I mean… a personal story on this was when I moved to Portugal back in 2009-10. I had been doing freelance IT consultancy but that involved going on site and loads of different clients, so I was seeing dozens of people each week. And then I went to sort of real, true home-based freelancing where I was doing a lot of writing, stuff like that. And I think I started going a bit peculiar, to be honest.

ALEX: A bit more peculiar?!

BEN: Well, okay! But, yes, when I did find myself going to occasional board meetings and things like that, I did find it was really quite an adjustment. That those kinds of things made me quite anxious. So I do think it’s really important to maintain a social life outside of work if work was a key part of your social life. The isolation doesn’t bother me but I think it would be very wrong not to say that it could be a problem for other people.

ALEX: Yeah. So, really, you’ve got that level of uncertainty, you´ve got to work out your own time management, you don’t necessarily have the support of a big company. I think that point is absolutely true.

I certainly didn’t realise quite how much, when all of your tax is done by the company, all of your benefits, even the car, that kind of thing. You’ve got to sort all that stuff out yourself. And again, talking as a man who has been involved with a bit of IT support, you know, if your computer breaks and you’ve got deadlines, you’ve got to sort that stuff out for yourself.

BEN: Yeah. I mean, there have been three occasions in the last 10 years when either myself or my wife have had to quite literally down tools and go and buy a computer. We now have a spare one in a drawer! Things like that happen, and it’s entirely on you, the buck stops with you all the time.

I do feel that I should reemphasise the pluses, though, at this point because I feel we’ve gone down the downsides too much. You’ve also got complete freedom. Your time is your own. All of those big, big pluses. They do balance each other out.

ALEX: Well, I wouldn’t be talking to you if I didn’t think that it’s more than balanced out. I absolutely love freelancing, and I think the thought of going back to a full-time job, particularly a high pressure fulltime job is something I wouldn’t want to do. And particularly for that work-life balance.

BEN: Absolutely. And I also love… when I talk about freedom, it´s the freedom to sort of branch out into other things as you can decide, “You know what? Next year I’m going to start doing this thing as well.” A completely random one: “I’m going to go on Etsy and have a sideline designing T-shirts and motivational slogans.”

I know, however random something like that might sound, you can literally do anything. Well, try telling a boss you want to spend two hours a day designing T-shirts. He’s not gonna be up for it, I don’t think.

ALEX: This mythical boss we always talk about on these podcasts, he sounds like a bit of an old nightmare really.

BEN: Yes! I think the mythical boss that we talk about in the podcast is a sort of amalgamation of all the different bosses that we have both worked with over the years. Nasty piece of work, he or she.

ALEX: Okay, we’ll go back in a minute. We decided that perhaps, you know.. getting back into work or going from a full-time job, how do I get started freelancing?

BEN: Okay, well, you are going to need some clients, is the first thing. Now, what I do find, a lot of people do seem to delay that inevitable moment where they switch. And I think it is important to emphasise that at some point you do have to kind of make the jump and you do have to pitch for those first few jobs.

A lot of people, and I mean a lot of people I know who have moved into freelancing, that first client is often their most recent employer or an ex-employer.

A lot of people move into freelancing by telling again that mythical boss, this time a slightly nicer version of that boss, that they intend to go freelance and saying, “But I’d love to continue doing this part my work, perhaps I could do that as a consultant for a day a week”. Or something like that. That’s quite a nice way to sort of slightly smooth yourself into it. Um, so that is a way to do it.

Obviously, I would recommend, perhaps thinking about what activity it is that you want to do and thinking whether you need to do any courses or training. There may be a freelancing course coming out from HomeWorkingClub soon, but I’m not going to take the plug any further than that at this point.

ALEX: I´ve said before Ben, you’re allowed to plug Home Working Club on the HomeWorkingClub podcast. I don’t think people are going to be upset by that.

BEN: Okay, fair enough! I´ll say no more, but there may be a course of my own coming soon. So…update your training. Make sure that you’re fully competent in what it is that you’re going to sell.

ALEX: I think this gets to the point, actually. Certainly, some people seem to think that “Okay, I’m gonna give up the job. I’m gonna burn the tie. I’m gonna burn the suit. You know, and then go away and make T-shirts and sell them on Etsy.”

Is it much more common that people will do what they’re currently doing for day job freelance rather than completely changing their career and being their own boss?

BEN: I think it’s different for every person, and I think everyone has a very individual situation. Obviously, all of us have bills to pay. Just deciding you’re going to hand your notice in and that you’re going to start hitting up work and pitching for freelance work is a very high-risk strategy.

But then, I do also think that you do need to make the jump at some point. So it might be a question of getting yourself a sort of rainy day fund. A lot of people talk about three or six months worth of income to get you through the start. I also think, when people talk about that, that’s a little bit unrealistic.

I mean, it would be lovely if we were all in a position to save up that much money before making the jump. I think you do have to do it at some point, but obviously starting to do some groundwork so that you know that if you’re leaving your full-time, well-paid job on a Friday, you know, at least roughly, what you’re going to do on a Monday and know that you’re going to earn some money for it.

ALEX: Well, I think that’s a really good point. Not just at the beginning, but all the way through, it’s planning and having an idea of where your next money is coming from. It’s not all about money, of course!

I had a really good piece of advice when I first went freelance from an old boss, a nice one this time. He said, “Just look at the work that you’re going to do when you start talking to people. If it’s work that you really think you’re gonna enjoy doing, then price that really competitively.

And if something comes through that’s gonna be really difficult and a bit of a drag, price that quite high so that if you get the work you don’t mind the drag so much because you´re getting paid well. But if you lose out on the stuff that you think you’d really enjoy, you actually don’t mind being paid a bit less.” Which is the freedom a normal job doesn’t give you, I suppose.

BEN: Well, you’ve given me permission to plug my own website here and I do have an article on this, about setting freelance rates, actually. One of the things I did say there is that sometimes the difference between a job that you don’t want to do and a job that you are quite happy to do might be the rate that you’re getting paid for it.

So I’ll drop a link to that in the show notes, that particular article.

Yeah, I think you’re very much right there.

ALEX: So I mean, again, I think that hits on stuff that we touch on all the way through. Actually, part of being your own boss is actually having an idea of what you’re worth, what your time’s worth as opposed to what you’re worth as an automaton within the machine of a large company.

Gosh, I´m making it sound terrible! I´ve really enjoyed a lot of the work I’ve done in my career!

BEN: I think you do get quite conditioned into freelancing… that just the thought of being back in the corporate machine… it really does make me shudder. The thought of actually having to be at a place at a certain time and having to answer to people. It’s alien to me after this much time.

ALEX: So going back to getting started, again. Courses I think are interesting. And it sometimes… you know we talked about accountancy earlier on. There may be a case that, if you’re looking to be a freelance accountant, that kind of thing, there might be certain things that you want to look at where there are skills that you didn’t use in your day job that would actually be really important for clients.

And then presumably, as you keep doing work, you will be able to find areas where you think, “Actually, I could do with a bit more training in that area.”

BEN: Yeah, I think this is something… it’s very easy to get left behind. If you’re at a decent company, you will get put through training courses and things like that. It is quite easy as a freelancer to almost get stuck in a rut and forget that you need to keep updating your training.

The reality is that a lot of freelancers out there are being very proactive about this. Especially when you are talking about technical things and new social networks, or anything like that. You will get left behind if you don’t carry on learning all the time.

If you’re with a good company who’s putting you through courses, they´re probably putting quite a bit of money behind that training. Thankfully, there are a lot of ways to learn by spending little or no money. I mean, even Google, Apple, Facebook all do really good, detailed training courses that they don’t charge a penny for.

So, it is easy to keep your training up-to-date. It is something well worth doing both once you´ve become a freelancer and in the run-up to it in order to prepare yourself for it.

ALEX: Well, if you think about large companies, they spend a huge amount of time and actually have big departments full of people that are actually looking after the training of their employees, the health and well being of their employees.

I think that’s another thing to be really strong about when you are your own boss. Don’t be that horrible boss. Allow yourself a little bit of time off. Allow yourself to go for a run or go to the gym, if that’s your thing. Allow yourself to sit down and read a book, or whatever. Allow yourself that headspace to make you a more effective person.

I think you can see a lot of people… I’ve certainly seen it – people get into burnout mode when their own boss.

BEN: It is and I have written about this recently in an article and I can’t for the life…

ALEX: What website is that on?

BEN: It´s on HomeWorkingClub.com.

ALEX: Oh, right, okay!

BEN: I’ve written about this recently, that I do think a lot of people do turn themselves into their own horrible boss. Over here, where we are in the UK, we’re currently looking out the window at a very windy and grey typical sort of winter British day. Well, when we do get our first day of sunshine, which I’m hoping will be around…

ALEX: In about six months time!

BEN: When we get that first day of sunshine, I will be dropping anything that I’m doing and I’ll be out in that weather, I’ll be going and having a drink in the pub, I´ll be sitting by the sea, or something like that.

That to me is one of the most wonderful things about freelancing! But, trying to persuade other freelancers, even in my social circle, that it is all right to do that… it´s just… Don’t be your own horrible boss. Give yourself the afternoon off! Otherwise, what’s the point in putting up with the downsides? And I think, yeah, not becoming your own horrible boss is really important.

ALEX: Just to recap, and we’ll go back through it in a minute. I mean, I think it’s fairly obvious, at least I hope it’s fairly obvious, that we love freelancing. I think that’s kind of the ethos behind the Home Working Club.

But there are some things you need to be aware of. Actually, I know I say this a lot, but it’s really, really helpful to learn from other people’s experience. So that’s what Home Working Club is there for, but also talk to friends who’ve done that.

I know that friends… I probably freelanced a lot before my friends did. I think I spoke to Ben when I first went freelance. I’ve spoken to a lot… a lot of friends have spoken to me and said, “You know, where should I go? When should I make that jump? What should I do?” And I think… what we’ve covered here.

Be really, really certain that (a) you want to do it (b) what it is that you’re going to do – if that is doing the same work you’re doing now or making that complete jump into a different business idea you’ve had for years.

There’s great freedom and flexibility. But with great freedom and flexibility comes a huge amount of risk. Really be aware of what you need from a technical perspective. Really be aware of what you need to set up as a business: tax, finances, bank accounts, all of this kind of stuff that you’ll get into. It can seem horribly daunting, but actually, it’s quite easy once you get into it.

BEN: Yeah, I think it seems daunting, but it’s one of those things that, if you just do one small step at a time… you can start to lay the groundwork for a freelance career months and months before you finish a full-time job.

That could be in terms of just cutting your cloth a bit differently and not spending so much money; saving yourself up an emergency fund; getting your training up-to-date; starting to reach out to people on LinkedIn and people in your social circle, talking about what you might plan to do.

And I think, that networking element of it… I’m not fond of networking. I prefer to keep myself to myself largely… But I do think a lot of the time when you’re speaking to other freelancers, you end up having ideas, “Oh, well, I’ve got a client who needs that” and you do end up…

There is an element of “it’s not what you know but who you know” quite a lot of the time. And quite often you do find that those jobs do come from people who you dealt with even 10 years ago in a job.

ALEX: Yeah, I find that… Well, networking is a huge part of what I actually do so I find it vital for me. That I have to keep in touch. I actually did, for a short period of time, I kind of didn’t tend my networks very well and I got people going “Oh, I´ve not seen you for ages. What’s going on?”

Actually, probably from my own sanity´s point of view, it was really important. But actually, it was important from a work perspective because it’s not necessarily that one conversation you have with that person on that day.

It can be a conversation you have with someone and you go, “Oh, this is what I’m doing.” and then they will talk to somebody three months later and go “Oh, hold on, I know someone who’s doing that.” And that’s how things can build.

BEN: Absolutely. One thing I think I’d like to add is…don’t panic if you think, “Well, I want to freelance but I don’t really feel that I have this network.” I mean, you can pitch for jobs on Upwork. There are thousands of new jobs added to the freelance job boards every single day. Every one of those jobs could be a new partnership, a new person.

I’ve got people who I work for who I’ve met kind of “in the real world,” but then I’ve got people who I wrote one article for eight years ago who have become regular clients years and years on. You never know who is going to become part of that network. And so, don’t despair if you think, “I don’t feel that I do have anybody to ask”, because you can always build on it.

ALEX: Yeah. And I suppose that comes back to the central point: is it right for you? And actually, you can probably, more than any job, work in a way that suits you. So it’s a good idea to have an idea of how you work and what it is that you want to do. And then you can really kind of make it work around yourself.

BEN: Absolutely. And going back to something I said at the beginning, you don’t have to only do one thing. I mean, I wouldn’t encourage going scattergun and trying five new activities all at once.

I am very much copying something here that I heard in another podcast, so I have to credit, I think, the Neil Patel podcast that I heard this on. That if you see success as a circle that you’re working out from the middle of, eventually success lies on the edge of that circle.

So, the more you stay going in one direction, the more likely you are to get there. So you don’t want to keep changing direction. But at the same time, having two or three different income streams, even if they’re from completely different types of work, is, I think, a very good idea. And I’ve got an article on that, on portfolio careers, which I´ll put in the show notes.

ALEX: Excellent stuff. Hopefully, that’s given you a little taste of what it is to be a freelancer… some of the downsides. We’re all about being honest here and there is plenty of hard graft involved.

But actually, we’re two testaments to what a liberating and fantastic way of living it can be.

So thank you very much for listening. I do hope that you’ll listen to us again, but also, please do like and subscribe. Recommend us to your friends and network because we’ve taked about that, be that personal or virtual. And, of course, come visit us at HomeWorkingClub.com.

BEN: Yes, please do. Thanks very much.

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