Working from Home: Are YOU Cut out for it?

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I’ll get immediately to the point with this one: Not everyone is cut out for working from home. 

During the approximately 15 years I have been working for myself, I’ve spoken to countless people about self-employment, freelancing and working from home in a remote position.

Reactions are hugely varied. Some people immediately say they’d never take the home working route and would never want to. At the other end of the scale, you have people who are hugely curious and inquisitive. This is sometimes to the point of asking for specific advice on how they could get started with it themselves. Presumably, if you’re reading this, you’re in the latter category?

All of those questions contributed to why I founded (Along with the fact that working from home is becoming increasingly popular. Self-employment, in particular, is booming globally, and about to overtake the entire public sector in the UK, according to figures in The Telegraph).

Here, we aim to help everyone who truly wants a career as a home worker to get that career off the ground. 

The Two Varieties of Working from Home

If you want to work from home, you have two options:

If it’s a remote job for a single company you’re after, both FlexJobs and Virtual Vocations are worth a look. Neither are perfect but they do give you a chance of finding home-based jobs you may otherwise be unaware of.

You’ll find full reviews of both here:

At HomeWorkingClub, I aim to help people taking either home working path. I report on relevant news such as Apple recruiting for home workers. This particular article does place an emphasis on those who’d prefer to freelance, but you’ll still find some useful information within.

Branching Out on Your Own

As I said at the start, over the years I’ve been approached by a ton of people for advice on how to create a life around working from home.

But here’s the thing:

The percentage of people I’ve given detailed advice to in the past who’ve gone on to do anything remotely useful with it is depressingly small.

The fact is that establishing yourself as a successful freelancer, in any sector, is hard work. In terms of anything resembling instant gratification, it doesn’t come close to a traditional job – even one where you have to wait a month for the first pay-check.

In most freelance endeavours, you’ll still be setting things up and paying your dues when your employed counterparts see their first salary payment hit the bank. The real rewards come much later.

I’ve always had the above firmly in mind throughout the process of setting up I decided before I wrote anything for the site that I wouldn’t hold back on home truths and honesty.

Honesty is something sadly lacking throughout much of the home worker / make money online industry. Everyone’s so busy trying to tell you how easy things can be and how much money can be made that they don’t take the time to tell it how it really is.

This is what we aim to do differently here, even if it may sometimes come across as slightly bossy and cynical! In late 2018 I conducted a reader survey, and one of the main pieces of feedback I received was that people like this honest approach.

Life as a Freelancer

I LOVE being a home working freelancer. My wife adores it too, even though she was forced into it by a redundancy and thought she would hate it. We get to work in PJs, in bed, on the sofa or on a hotel balcony; We can enjoy unexpected warm days in the garden instead of looking at them out of an office window; We can take Christmas off every year instead of when it’s our turn; And we can ramp up our work if we want to bring in some extra cash for something special.

These are all fantastic things, but they don’t come without hard work and sacrifice. I mean the nights of sitting up until 3am getting projects finished, doing assignments for chump change to build up good online reputations, selling our souls here and there on projects we detest but need the money for, and putting up with ongoing uncertainty and cycles of feast and famine, which will always be part of a freelance life. (I discuss more specific pro and cons here).

Not everyone is cut out for this type of existence – and that’s OK! Nobody said everybody should be the same. But the purpose of this article is to find out whether YOU are suited to being a self-employed home worker, or whether you’d be better off finding a more traditional day job.

The following questions may be tough to answer. They’re supposed to be. There’s also absolutely no point in bending the truth with your answers. If you can’t answer “yes” to the majority of these questions, your chances of freelance success are slim. Now how’s that for honest?

How to Work Out if YOU Are Suited to Freelancing

1. Are you willing to pay your dues with low-paid work?

Whether you’re planning to set up shop as a freelancer on a site like UpWork or start selling on eBay, you’re going to have to start at the bottom.

With freelance platforms like UpWork, that means accepting jobs at super-low rates to build up your star-rating and reputation. With eBay selling it means letting some items go for below market value until your feedback is good enough for people to trust you.

In both of these cases (and plenty of others), this means ploughing hours into something for next to no reward, and certainly a level of reward that’s often far below a living wage in the western world.

For experienced people, this makes perfect sense. Often businesses take months or years to make money. However, I’ve personally spent hours explaining to people how to get established on platforms like UpWork, and been extremely clear on this part of it all, only to see them walk away grumpy and dejected long before getting their first assignment.

If you’re not willing to put some serious work in to learn and to establish yourself, go and get a job in a bar with a guaranteed wage. Freelancing is NOT for you.

2. Are you prepared to go where the money is?

Home working is something that gets easier as you get more established, but in the early stages you won’t get that much choice in what you do.

An example always springs to mind from when I was getting started as a freelance writer. I spent two days researching pallets and waste management, in order to write 10,000 words of related website content. That’s basically a dissertation on wooden pallets.

I don’t think I earned very much from it and hated every minute, but I put my head down, got the money and got the five-star feedback.

My favourite example of “going where the money is” is something my wife and I did about six or seven years ago.

We both used to do very basic product description writing for a now-defunct Facebook-based freelance platform called CloudCrowd. About a month before Christmas they had a huge rush-job on and were begging for more workers to help over a specific weekend. My wife and I reached out to everyone we could remember who’d said “ooh, let me know if you ever get any extra work I could do…”

We thought people would bite our hands off, especially with it being just before Christmas. In fact, as far as I’m aware just one of our associates managed to do a few descriptions and earn a token amount.

Meanwhile, my wife and I cancelled our plans, ordered pizza and beer, and earned around $2500 (£2000) that weekend writing mind-numbingly boring product descriptions. It comfortably paid for Christmas.

I’m aware this probably comes across as “ooh, check US out!” but I have a really important point to make here: Any one of our friends could have made that money that weekend – or just set aside half a day and made a proportion of it. But they didn’t.

The point is that there’s oodles of money to be made in the online world, but the people making the lion’s share of it are the people willing to put in the graft. Yep, it’s just like the real world.

I’ve written more about this topic in Jobs for Lazy People. It’s a topic I have plenty to say about!

3. Are you comfortable with uncertainty as a freelancer?

I know several highly skilled professional people who could at least double their income if they switched from their payrolled jobs to freelance consultancy. They could wave the office goodbye and swap commuting for a life working from home. They have absolutely no desire to do so.

(I’m also pleased to say that since writing the first version of this article, I’ve seen two good friends make the jump and reap the benefits). 

The reason many people shy away or delay making the jump is the inherent uncertainty that comes with home working and freelancing – and it’s completely impossible to deny that it’s a very valid factor.

(If you’re tempted to make the jump, I have a detailed free guide to help you prepare for the transition).

I could cite so many examples of uncertainty that self-employment has brought me. A couple of years after setting up in IT consultancy, I finally started to feel successful, only to abruptly lose my biggest client. This was not due to any problem, but because their own success had resulted in a buy-out by a bigger company with its own IT department.

The Christmas when I was owed a five-figure sum in outstanding invoices and didn’t know if I’d be able to buy food or presents until a couple were finally paid on Christmas Eve was another highlight too.

I’d be the first person to agree that uncertainty is part and parcel of freelancing life.

That said, in reality uncertainty is part of being employed too. Anyone could lose an old-school job at any time, with anything from a week to three months’ of notice. There is an argument that a home worker with several different streams of income is actually subject to less risk of a monumental life change than someone with just one job. That’s the argument that keeps me (just about) sane.

4. Are your computer skills up to scratch?

As I’ve discussed in a previous post on computer fundamentals for home working, computer skills are all but essential for modern home workers.

Obviously, you need to know far more as an Internet marketer (for example), than someone making crafts and listing them on Etsy or eBay. But the basics of file and folder management, image manipulation and keeping backups of data are still real essentials.

I won’t reiterate everything mentioned in the previous post here, but it does bear repeating that inadequate computer skills will, at best, drastically slow you down and reduce your home working earning potential.

5. Can you prioritise and manage your time?

If you’re prone to procrastination or easily distracted by the TV, you may well struggle as a home worker.

I’m perhaps lucky in that I enjoy the buzz of having a lot to do far more than I enjoy vegetating on the sofa. In fact, in the early days of a project like HomeWorkingClub, my bigger problem is that I tend not to sleep, eat, exercise or bathe!

But this is a serious question. When it comes to freelancing you get out what you put in, and thanks to a global army of freelancers competing for work, someone else will do the work you don’t get around to. If you don’t think you can motivate yourself, you may be better off with a traditional job, where you can be motivated by the fact that you’ll eventually get fired if you don’t turn up.

I have some useful tips for time management here. 

6. Can you handle rejection?

Rejection is part and parcel of working freelance.

I remember reading something once that said people applying for freelance gigs on UpWork try for an average of forty positions before landing the first one. That’s a whole bunch of rejection.

It’s the same in all kinds of home worker roles. eBay items that take an age to list and then go for 99p; Blog posts that nobody reads; And, worst of all, incredible pitches that don’t even get an acknowledgement.

It does get easier to deal with this, and really bad examples of rejection get less frequent with experience, but plenty of people bottle out before they turn that corner.

This, however, is good news for those who stay the distance. I know people who can land as many as one in three of their UpWork pitches now. That basically turns a hugely competitive marketplace into a tap of new projects that can be turned on at any time.

7. Are you professional?

If you are consistent and highly professional when you’re completing your freelance jobs, nobody really cares if you’re working in your PJs (people assume we all do it anyway!)

But it IS important that you are professional, whether you’re selling on eBay or selling consultancy services for a thousand a day.

I’ve been personally involved in hiring and managing freelancers for plenty of clients and projects. Here are just some of the things I’ve seen:

  • People sending a fantastic pitch for a role (a pitch that will have taken them ages to produce), only to fail to respond to any further communications.
  • Individuals negotiating great rates and then disappearing completely.
  • Freelancers continually turning in work late. (I’ll admit I’ve been known to sometimes keep on freelancers like this and work around their tardiness, but you can be sure they’re last in the queue for any raises or exciting new projects).

This “are you professional?” question is going to be the hardest one to answer honestly because nobody wants to admit to themselves that they’re not.

However, it’s utterly pointless for anyone to lie to themselves about this, because every day their shortcomings are shown up by all the people out there who are professional. These are the ones making the money, and the ones far further along the path to a lucrative career working from home.

So how do you feel having read through all of that? Do YOU have what it takes? Would you e better off going freelance, seeking a remote position, or sticking to the commute and the day job?

Share your thoughts in the comments!


4 thoughts on “Working from Home: Are YOU Cut out for it?”

  1. What can I say other than “I’d rather put in this work to make god on what I have than put in similar work for a more certain dead-end”? Writing is my dream and freelance seems the way for a nobody to work towards being somebody. Rejection isn’t an issue after selling insurance; ten-thousand words about pesticides – or about anything technical – is nothing compared to an appellate legal brief. Where I may come up short today, I have every intention of improving already. *Stares down clock.* Thank you for your frank and clear descriptions of important realities in professional writing. Your points have not dissuaded me, only caused me to reevaluate my early expectations.

  2. Thanks for the completely honest take on starting off as a freelance writer. After reading through the entire list I’m still willing to plough ahead (after taking a deep breath)


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