Podcast 1: Remote Working vs Freelancing

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In our very first podcast, we tackle remote working vs freelancing.

They both involve working from home, but are very different. On one side you have a boss, but also a regular paycheck. On the other you have total freedom, but no job security and income that come in in fits and starts.

Included in this podcast:

  • An introduction to HomeWorkingClub (0.57).
  • Remote working vs freelancing (2:52).
  • Convincing a boss to let you work remotely (3:55).
  • An introduction to freelancing (7:34).
  • Similarities between freelancing and remote working (10:02).
  • Big companies that hire remote workers (14:05).
  • A sneak preview of the next two podcasts (16:27).

 Supplementary Links and Information

Remote Working vs 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, and I’m here with Ben Taylor, the founder, CEO and president of Home Working Club. Did I build you up rather a lot there?!

BEN: Ha ha, yeah, I don’t call myself CEO or President. But yes, I am the Founder of HomeWorkingClub, yes,

ALEX: This is a brand new podcast, and we’re coming to you from HomeWorkingClub World Headquarters. Actually, it’s a shed at the bottom of the garden. But that’s what it’s all about.

BEN: Well it’s your shed, and it’s a very nice shed.

ALEX: The point of this podcast really is to help you find your way through the minefield of working from home – be that as a freelancer or working remotely.

Before we go into that subject, though, I think it’s really useful just to get a little bit of background on Home Working Club itself. Ben, you set up HomeWorkingClub up in 2017?

BEN: I did. Yes, I set it up after having worked for myself freelance since 2004.

I did IT consultancy for the first five years, which was successful but burnt me out to the point that I decided to jack it all in and move to Portugal!

It was a wonderful experience, but I did find myself sitting there – cross legged on the bed – trying to work out how I was going to make any money, after I walked away from my IT business.

Like so many people, I found myself just with a web search bar, typing in “how to make money online” – like I think many of my readers do.

I realised very quickly that there’s a lot of misinformation; There are a lot of scams, and it’s possible to get lost down an awful lot of rabbit holes while you work out what to do.

HomeWorkingClub was born, well, we’re talking eight years after that. I’d managed to negotiate these things. I wasted a lot of time, did a lot of work I didn’t earn much money for, but also found ways to be successful working for myself.

ALEX: Eight years of bitter experience?!

BEN: Yes, bitter experience and paying a lot of dues. But I felt that I had a lot to a lot of information to share, and certainly the desire to help people. And also to provide more of an honest take on this kind of thing than is particularly easy to find.

There are a lot of people with hidden agendas, and we don’t really have one at HomeWorkingClub.

ALEX: Excellent. Just a quick note before we before we go any further: Anything that we mention throughout the course of the broadcast today will be in the show notes.

So I don’t feel the need to furiously take notes, particularly if you’re driving. That’s not an excellent idea.

BEN: No!

ALEX: So, really, the point today is what is the difference between freelancing and remote working? I can’t answer that question, but luckily Ben can. What IS the difference between freelancing and remote working?

BEN: Well, essentially, if we look at the similarities to start with. Home working could mean that you’re working for one company and just being allowed to do your work from home – remote working. Or there’s freelancing, which is essentially still working from home, but very different, because you’re really running a business of your own and very much responsible for your own destiny.

ALEX: So, remote working, what’s are the main things? Presumably you’ve still got a boss?

BEN: Yes, you’ve still got a boss. You’ve probably got set hours that you’ve got to work. And, you’re probably fixed working from one location, even if that one location is at home. But on the big, big big side – for a lot of people – you still get a regular monthly paycheck.

ALEX: OK, so say at the moment, if I was gainfully employed but commuting every day, what would be the moves to try and try and work remotely?

BEN: Well, you could do what my wife did when we moved to Portugal, which was that she actually put in a proposal to her boss to say, “we’re planning to move to Portugal, but I’d like to continue to work for you.” And she did actually persuade her company to allow her to work remotely.

ALEX: Yeah, so that fine for everyone really, isn’t it? Saves the company money…

BEN: Absolutely. And I think since then well, just over a decade has passed since then, and remote working is a lot more common. And I think a lot of companies have begun to realise the benefits of it as well, because they don’t have to pay for so much for office space, and they aren’t restricted to a kind of a circle around their headquarters where they can employ people from.

ALEX: I think that’s true. A lot of people find themselves in offices these days hot-desking.

I worked in one office where there suddenly appeared one day a massive bank of lockers, like a high school, where you were supposed to leave your stuff overnight, and have a clear desk so you couldn’t return to it.

People were locking pictures of their family up overnight and then putting on the desk the next day, every morning! I think companies are getting into that mindset where they don’t want to reserve a desk for every single person.

What can you do in terms of just some steps? If you’re going to make a proposal to the boss, what can you do – to give them some security that you’re gonna work as hard, if not harder, than the people in the office?

BEN: I think that is a very good point because I think different bosses have very different views on home working. I think some people are quite progressive, and see the benefits from it, especially if they’re allowing people to have a more flexible family life fitting in around school runs and things like that.

Other bosses are a lot more traditional. And I think especially some of these kind of…very workaholic bosses. Some of them I suspect don’t like being at home, and so would rather be in the office and therefore think everyone else should be in the office with them!

So it really does depend who you’re dealing with and who you’re pitching the idea to. But I think with the kind of thing my wife did, an idea is trying to do it gradually. So maybe suggesting initially, “can I do a day a week from home?” or “can I do two days a week from home?”

And then, hopefully, during that time you prove yourself, you prove that you’re just as available and just as efficient, perhaps more available and more efficient and less stressed because you’ve not just been in someone’s armpit on a train to work for an hour!

So yes, I think doing it gradually and providing yourself is a route to them accepting it as an idea.

ALEX: Yeah, I’ve seen that working for people, actually. Working from home is so common now that it’s not even a question. But I think there was always that thing where “I want to work from home one day a week….and guess what day that is? It’s Friday!

That was definitely the thing, maybe five or six years ago, even. But now I think it’s much more accepted that you can work around it.

BEN: I think so. And I think although you have still got those “die hards” on leadership teams who don’t want to let anybody work from home. I don’t think there’s any data to support the fact that people work less hard.

In fact, I think it’s easier to find data to support the opposite.

ALEX: Well, no, I definitely remember seeing stuff on that basis. And I think there’s that point that it’s a trust thing. If the company trust you to work under your own steam, you want to repay that trust. You want to keep hold of that flexibility

I certainly knows, when I managed teams remotely, that people are more judged on the work than they are on being in the office. And I think we’ve all done jobs where we can be in the office all day and not be incredibly productive!

BEN: Yeah, those “water cooler moments!”

ALEX: Which stretch longer and longer through the day! Yes, so let’s talk about freelancing briefly. What’s freelancing?

BEN: So, freelancing is very different. I mean, yes, you’re still working from home, but you don’t have a boss, you don’t have a fixed timeframe to do anything in. You can even work at night and sleep all day if you want, when you’re freelancing.

But going back to that key point, you don’t have that regular monthly paycheck. And that, for many people, is a very scary thing.

ALEX: Yeah, I was talking to a friend of mine. He was thinking about going freelance and giving up a really, really good job, actually. And I’d been working for myself for a few years by that point

He said: “is it incredibly liberating, or massively scary?” And I said “both, all the time!”

BEN: Absolutely, absolutely. In equal measure.

Yeah, I think you don’t miss the company politics..but then you realise when your computer stops working, that you don’t have an IT team to speak to. Then there are those things with health care and benefits and stuff like that, where you used to go to human resources. You don’t get to do that anymore.

You do suddenly feel very alone at times!

ALEX: Absolutely. That support matters, and I think sometimes, particularly when you’re slightly longer in the tooth as I am, and you’ve been used to working in large companies. You’re suddenly away from there, and it can be really, really difficult not to actually be able to pick up the phone.

In fact, that’s how I first met you. You  picking up the phone to answer problems that were way below your pay grade.

BEN: That’s true, actually! But I don’t think we need to go into that for the podast!

But yes. With freelancing. I think it does kind of work in reverse as well, because I simply cannot imagine, after 16 years of working for myself, EVER having a boss again, and I think that’s very common.

Obviously I speak to a lot of freelancers in running the site, and in my personal life is well. And there are very few who go freelance for more than a year or so who ever would want to go back.

ALEX: Yes, absolutely. I think that that freedom really does become something you definitely don’t want to give up.

So, those are some of the different things. What about some of the similarities between the two?

BEN: Well, you work from home, and you don’t have to commute, which I think it is wonderful in so many ways. Because I mean, when I worked in London, I commuted at least an hour each way, and I don’t think that’s uncommon. Also, I think everyone’s a lot more environmentally aware these days as well.

And you’re giving up two hours a day. You’re giving up 10 hours of your life every single week. That’s 10 hours where you could actually be achieving more. Also, all of the pollution that’s being created by all of those car journeys and things like that.

So similarities, however you’re going to be a home worker, then you are working from home. Whether you’re a freelancer or whether you’re working remotely. There’s dress code too.

I know there’s a bit of a kind of stereotype that all of us freelancers sit working in our pants or our PJs. And, yes, that IS the case sometimes. Although I can assure you that Alex and I are both clothed.

ALEX: Yes, fully, FULLY clothed!

BEN: There is less formality, and I think yes, you’re immune to office politics to an extent when you work remotely.

But obviously, when you’re a freelancer, you could pretty much ignore office politics. Which is a wonderful thing.

ALEX: Of course, you do have the the prevalence of Skype video calls these days. Yeah I’ve certainly had those moments where I throw on a shirt and tie, so I’m looking very business…from the desk up.

BEN: Yeah, yeah, I think that does genuinely happen! I have to say that there have been many occasions when I’ve said I can’t put my video on right now because….there’s a problem with my webcam or “my wife’s on another video call and I don’t want to use up all the bandwidth.”

That’s that’s an excuse I’ve used many times. So if you ever have call to talk to me on a video call and I make that excuse on, I am probably lying!

ALEX: Don’t admit you’re lying!

Getting into some of these things. Something I know from speaking to people is that – particularly if you’re new to working from home – either freelance or remote working – is that it can be really difficult to get into that routine.

The one thing about going into an office is you have the commute. You’re mentally prepared. You walked through the doors. You said at your desk. You’re AT WORK. Then, at the end of the day, you go home, you get back, you get out of the car. You’re AT HOME.

What can you do? Any easy tips to help getting into that mode?

BEN: I have a bit of a controversial view on this. Because there are all these “by numbers” articles on how to work from home effectively that you read. They will say, “have a dedicated workspace” and “dress for the office even if you’re working from home.”

I think a lot of the time it’s almost just like a “fill in the gaps” article that you’ve read 100 times before. And I think really it depends on the individual.

I quite often wake up in the morning and pick up my laptop and start working, and I will stop and get up and have a shower at a suitable moment. That’s one of the wonderful parts of the freedom of freelance and working for myself.

My wife is completely the opposite. She very much feels that she has to work at a dedicated desk. She even likes to keep the times that she works more regular than than I do. So I really think it’s down to the individual.

But obviously, if you’re remote working, you will probably have less freedom with that kind of stuff than if you’re freelancing.

ALEX: Yeah, I think a lot of remote working offices have messaging systems. They know that you’re at your laptop and if you step away from it. But what you’re saying is that it’s really about finding your own comfortable way of working.

So, in terms of that, actually choosing what it is that you do: freelancer vs remote worker. How can you work out what’s right for you? That’s a massively broad question isn’t it?!

BEN: It is rather!

Freelancing, and this is something that I was writing about just the other day…I think if you’re going to be a freelancer, it IS running a business of your own. With that comes being entrepreneurial, and with that comes risk.

If you are someone who is not going too be happy if you don’t get that regular paycheck, freelancing is going to be a very uncomfortable step for you.

And it’s not as if remote work working is rare. We plan to discuss this in a future podcast, but there are an awful lot of companies who routinely hire remote workers.

So if you want to work from home and you don’t want to freelance and you don’t want that kind of that risk in your life, there’s still plenty of options. And whether you’re at entry level – at the beginning of your career – or whether you’re a high powered executive, there is still plenty of home working positions out there. And so really, I’d say that’s probably the most important thing to consider: how comfortable are you with risk.

I’m not saying I enjoy the feast or famine nature of freelancing, because that never gets any easier. But I do quite like the “flying by the seat of my pants” feeling. I enjoy that, but I know it doesn’t appeal to certain people.

ALEX: I know a phrase I see in your writing a lot is “paying your dues.” And I think that’s the point. We’ve known each other a long time, and I’ve seen you doing that, being a freelancer way before I was. There’s that point that you can’t go from a “full benefit” office job with similar lifestyle and similar wages. When you’re freelancing, it takes some time to build it up, doesn’t it?

BEN: Absolutely, Yeah, there is a learning curve. And there’s a big “paying your dues” phase where you might have to make some personal cutbacks in your lifestyle and things like that on. You have to be willing to do that. And I’ve met a lot of people who aren’t willing to do that.

ALEX: Yeah, I think someone said (I can’t remember but will put it in the show notes), that we underestimate what we can achieve in 10 years but overestimate what we can achieve in a year. So sometimes you think by this time next year I’m gonna be fabulously successful, actually, it doesn’t always work out like that. But if you take that longer term view and say, actually, I’ve got a plan to get to this place in a certain period of time…it makes the shorter term difficulties a bit easier doesn’t it?

BEN: I think that’s true. And that’s made me think of a good way to contrast the two things.

I think in a what I would call a “traditional job,” that progression can be a lot more linear. You kind of expect, if you perform well, you’re going to get periodic promotions and that kind of thing. With freelancing, it’s a lot more “fits and starts.”

It’s a year when nothing happens, a year when everything booms, and then a year when everything goes completely to….well you know! That happens and it goes up and down a lot more, and you need to be comfortable with those peaks and troughs if you’re going to freelance.

ALEX: Good stuff. So for the next two podcasts, one will be entirely about freelancing, and one will be entirely about remote working. There are big differences between the two, although obviously the dress code is similar!

So just in terms of freelancing briefly, any idea what what sort of things you’re gonna dip into in that one?

BEN: I think I’d definitely like to cover just how many different options there are. I’m contacted by an awful lot by people who just day “I want to work from home, what can I do?”

I think a much better way to phrase that question is…I don’t know…”I want to design fashion, and sell it online through Amazon Merch. How do I do THAT?” So I’d definitely like to touch on that. But I think also with freelancing, it is a question of freelancing being the only option if they want to have a certain kind of lifestyle.

An email that I get very, very often is people saying, “I’d like to live in an RV and travel around America, and I’d like to work for a company remotely.”

The reality is not very many companies are gonna let you do that! Yes, they might let you work from home, but they’re assuming that they know your home address and that you’re gonna be there from nine to five. They will really want to know if you’re going to be in Utah or Nevada, you know what I mean? It’s not quite as straightforward as that.

It may be that you work for a company for a period of time, and you can convince them that you will continue to work effectively from your RV. But, no, it’s not that likely, to be honest. And so, yes, I think that’s definitely something I’d like to touch on as well.

And perhaps how you can turn a traditional career more into freelance remote by doing consultancy and things like that.

ALEX: Great stuff. And with the remote working podcast? Presumably you’ll look at that strategy of how you go from not being remote to being remote?

BEN: Absolutely. But also how to look on the open job market for remote roles. I mean, companies just off the top of my head. American Express, Apple, Dell…That I’ll do, for starters, American Express, Apple and Dell!

ALEX: They’ll do!

BEN: They all routinely hire remote working people at all levels. Those jobs are out there. But, sometimes they’re hidden in plain sight. So I’d like to talk about how easy it is to find those jobs once you know how to look for them.

ALEX: Well, fantastic. Thank you very much Ben. I’ve really enjoyed this chat today. I hope you listening have enjoyed it as much as we have, and have found it useful as well. Tune in again for the freelancing and the remote working podcasts, which should be coming up soon.

And again, anything that we’ve mentioned today, we will work hard to put in the notes afterwards.

Also, if you’d like to get back to us and leave any comments, leave them them underneath this and we’ll try and respond to those as well.

BEN: And if I may add, please subscribe on whatever podcast platform you’re listening to, because I’ve been told that more subscriptions means more people will find the  podcast which will give us more resources to carry on doing it.

ALEX: And obviously positive reviews as well.

BEN: Well, yeah, we don’t want negative ones :-)Thanks!

4 thoughts on “Podcast 1: Remote Working vs Freelancing”

  1. Transcription Typos…
    “jack it all in and move to Portugal!” (PACK it all in)
    “That’s not excellent idea” (that’s AN excellent idea)
    “you’re gonna be there from nice to five” (you’re gonna be there from NINE to five)

  2. Hi as the first podcast I have heard of yours it was great, almost therepy. I feel more relaxed about the whole thing already. Trust me today was a BAD day. Thanks for making it better. Now where is the next podcast…


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