How to Work from Home: The Ultimate Guide to Working Freedom

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Deciding to work from home as a freelancer, and breaking away from the comfort and security of life as an employee, is a BIG thing.

I know from personal experience that it’s daunting and frightening. It’s this fear that causes people to squeeze onto crowded roads, buses and trains on most mornings of their adult lives.

There IS an alternative, and this article will take you through it step by step.

There are an increasing number of us in the world who don’t have to commute, don’t have to ask permission to go on holiday, and don’t have to spend Monday to Friday playing company politics. If that sounds good to you, all you need do is read on.

Contents of this guide:

What you will be able to do after reading this guide
A warning
Great things about home working
Bad things about home working
ACTION POINT 1: Working our your personal pros and cons
How to get started
Work from Home Ideas
Training and Learning
ACTION POINT 2: Decide what to do and audit your skills
How soon can you go freelance?
Case Study: Louise
ACTION POINT 3: Work out when you can start
The Big Jump!
ACTION POINT 4: First steps in freelancing
Work from home freedom

What this guide will do for you:

By this end of this extensive guide, you should be able to:

  • Decide whether a switch to freelancing is right for YOU, based on an honest assessment of the pros and cons that are specific to YOU.
  • Work out how long it might take to get started.
  • Get an idea of what actions you need to take before you’ll be ready to start to work from home.
  • Gain a clear idea of what your first steps will be along the freelance journey.


I’ve included suggested “Action Points” throughout this guide. To tailor this advice to your own situation, I’d recommend working through them.

A Warning

What you’re about to read is not some daft “work from home blueprint” that promises untold riches with minimal effort.

Choosing to go freelance is a life changing decision. It comes with inspiring highs and soul-crushing lows. The only certainty is uncertainty. However, in the long term it’s generally an endeavour that rewards the work you put in (and, equally, one that will leave you struggling to pay the bills if you slack off).

It’s NOT a life for everyone. If you have a well-paid job that you enjoy doing, think VERY carefully before assuming the grass of a work from home life is greener. You’ll find an article on whether home working is for you here. If you’re not sure if you’re ready, it’s well worth checking it out before going any further.

Still here? Good. Let’s press on.

Great Things About Home Working

The benefits of working from home go way beyond the stereotypical image of being able to work in your pyjamas, or with the TV on. (Although I strongly suspect that all the freelancers who claim not to do these things some of the time are lying!

It’s not a struggle to think of plenty more benefits of the work from home / freelancing life (terms that are essentially interchangeable for the purposes of this article).

The following list is inspired by what I personally love about this life, but you’ll no doubt be able to think up other things that apply to specifically to you:

  1. Being at home the second work finishes.

This means no commute, and no finishing at 6pm and getting home at 8pm. Most importantly (in my case) it means a full evening with my infant son instead of a snatched goodnight kiss.

  1. Having the ability to eat a decent lunch from my own kitchen.

It’s great to be able to menu plan for a whole week, and be on the spot to eat leftovers from big meals. It’s economical too.

  1. Being able to have control over social interactions.

This is unique to me, but I see it as a big attraction for fellow introverts. I find office environments rather draining, and they’re not where I do my best work. Sure, I can step up with a presentation or face-to-face meeting when needed (and it’s quite important to do this to avoid becoming a recluse!) but for me, at least, freelancing is better for my mental health.

  1. Having the ability to pick and choose who I work for, and what I work on.

This is one to be careful with, because if you’re too picky and discerning you’ll end up with no work and no money! But even at a basic level, the ability to send people packing if they drive you nuts is incredibly liberating. If you have a “traditional job,” you don’t have this option.

  1. Being able to change direction at any time.

If your work from home life starts to feel stale, you can change it at any time – just learn a new skill or sell a new service. You don’t get to change your job description every time you get bored if you have a “real” job.

  1. Unlimited earning potential and pleasant surprises.

When you are in a payroll job, you know exactly what you will get paid and when. That’s awesome in some ways (and believe me, you’ll envy it at numerous points along your freelance journey!)

But when you’re self-employed, you get good months, exciting times when you earn extra that you don’t expect and – if all goes well – a career that will pay you far more in the end than your old job used to.

  1. True freedom.

It’s unrealistic to say you’ll never have to answer to anyone again (freelancing can feel like having multiple bosses). However, you ARE ultimately in control.

Many people who dip their toe into freelancing and work from home for just a short time quickly say that they could never go back to “working for the man” again. My wife was one of these people (more on that later).

Bad Things About Home Working

Freelance reality

I hope that last section provided you with plenty of inspiration, because it’s reality time.

There are plenty of negatives when you work from home too, I’m afraid. Again, this list is rather tailored to my own experience, but I’m sure you’ll think of some ideas of your own.

  1. Being at home the second work finishes.

Yep, it’s the same point I put on the “good things” list! Most of the time it is a blessing, but sometimes…just sometimes, having to go from ultimate freelancer to ultimate parent without a second to catch your breath in between is exhausting.

And when you fail to finish on time and just have to get something done, it’s really hard to explain that to a toddler when you’re shut away working in the same house.

  1. Struggling to switch off.

I’m typing this post at 11pm. Now, it’s important to note that that’s because it’s for my own site, which is something of a labour of love. I also don’t personally see it as that bad a thing when I enjoy some of my work more than binge watching Netflix.

However, boundaries are important, and when you work from home they can get really blurred.

Some home workers claim that they get around the boundary issues of home working by having a dedicated home office space or a ban on technology after a certain time in the evening. I call bullshit on the vast majority of these claims.

I work within various teams of home workers, and they are online at all kinds of hours. The thing is, most of the people with traditional jobs are too. This is a problem with modern society, not with home working.

I’m not ignoring the importance of strategies around this, but they’re different for everyone. At least when you’re freelancing, you’re doing it for yourself and not for someone else.

  1. No holiday or sick pay.

This one seriously sucks. My wife and I both freelance, so taking a week completely off means both of us either doubling up work on the days before and after to fund it, or simply taking the hit and not earning while we’re off.

Being ill is even worse. In fact, being ill as a freelancer and knowing that you’re either going to piss your clients off or have to work all hours to catch up (invariably the latter), is possibly the worst thing about home working.

What tends to happen is that you try to power through every time, and end up prolonging whatever illness you have. With a payroll job, you’d just take a day or two off and get some proper rest. When you work from home you end up ill for a fortnight with a bug you can’t shake off, working throughout.

  1. Having to do everything.

This one doesn’t bother me that much, but having to do every possible business task is a real pain for many freelancers.

My most hated tasks involve annual accounts and insurance policy renewals. They take ages, cost money, and I earn nothing at all while I’m dealing with them.

Freelance life turns you into an expert in all kinds of business things. Some of them are things you’d happily have never learned anything about.

  1. Lack of social interaction. 

I’ve already made it clear above that the lack of social interaction when I work from home doesn’t bother me. In fact, if I spend too long in any one day on Skype, Slack and other such systems, that can be enough for me to wish everyone would leave me alone!

However, I’m including this because a recent Plan Sponsor survey highlighted “lack of social interaction with coworkers” as the biggest downside of home working, selected by 62% of the people they spoke to. So it obviously bothers plenty of people.

  1. Lack of exercise.

You might think that all the extra time home working saves in terms of commuting would provide time for exercise, and in theory it should. However, this all depends on your mind-set.

Personally, I’m terribly unmotivated when it comes to exercise, and equally terrible at stepping away while there’s still work to do. This adds up to a very sedentary combination. At least commuters walk from their trains to their offices.

  1. People not “getting” that you work from home.

This one isn’t such a problem for us these days, but it was a real issue when we lived in a small village where everyone knew us.

Essentially, people don’t “get” home working if they don’t do it themselves. It’s as if they assume that you’ll finish at 5.30pm regardless. They don’t realise that it will end up being 7.30pm if they pop in and chat for two hours during the day.

Action Point 1 Home Working
Have a good think about the positives and negatives of freelancing from your own perspective. Then write them down.

You may choose some of the same reasons I’ve highlighted above, but there will be others personal to you.

You may have the motivation to run every lunchtime, for example, or have a gym near to your home that you’d visit. Social interaction (or lack of it) may be important to you.

The important thing is that you’re completely honest with your answers. Base them on who you ARE and not who you’d like to be.

If you’ve never stuck to an exercise regime in your life, starting to work from home will NOT be the magic change that makes you do it. Similarly, while working from home, for me, means being able to eat healthier food from the kitchen than I would from an outlet in the city, for you it might mean snacking on chocolate all day.

Another example is that I don’t tend to succumb to distractions like TV or household tasks. If you know, deep down, that you would, you should include this as a negative that could impact your success.

What you’re looking to aim for is your own list of pros and cons. One which either inspires you to take your planning further, or one that shows you that perhaps freelancing isn’t for you.

How to Get Started

If you’re still with me, I’ll assume you found enough positives to outweigh the negatives of home working?

The next thing to do is to come up with an idea of what you want to do. Hopefully, that’s an easier exercise than deciding whether you’re ready to go freelance at all.

Working freedom

The thing that makes choosing a freelance career both wonderful and slightly dizzying in equal measure is that you can literally do anything you want. For anyone making the switch from a full-time job, that’s quite an extraordinary choice to be faced with.

Let’s consider some of the work from home jobs people can do. I’m literally going to pick the first ten that come into my head:

Work From Home Ideas

  1. Freelance writing.
  2. Setting up an eBay store.
  3. Making crafts to sell online or at local events.
  4. Running a blog.
  5. Foreign exchange trading.
  6. Virtual assistance work.
  7. Online counselling.
  8. Data entry.
  9. Website testing.
  10. Designing T-shirts and selling them online.

Not only is that list merely the first ten things I thought of, I could think of 100 more.

And best of all, you don’t need to only choose one. I do four of those myself on a regular basis and have dabbled in some of the others.

This next part is very important. So important, in fact, that I’m putting it in bold:

You must be really honest with yourself at this point; Not just about what you WANT to do, but about what you CAN do.

An example: You might adore the idea of being a writer. But if you flunked English at school and still struggle with grammar and punctuation, you’re not going to be a good one, or make much money doing it.

Or, perhaps you’d like to run a blog, but are a real computing novice. While you may get one off the ground, your lack of knowledge will really slow you down.

The Good News – Training and Learning

The good news is that you have two options here:

  1. Choose a home working job (or jobs) you know you’re already skilled and qualified to do.
  2. Choose what you want to do, and work on building up the skills in your spare time until you’re confident enough to make the leap.

The even better news for people considering option two is that there are countless free resources online for people who want to learn.

Some examples: CodeAcademy teaches programming in all kinds of languages; English Grammar 101 will help you brush up on those bits of English you’ve forgotten from school, and the likes of Coursera and eDx deliver courses in all topics from the likes of Harvard and Berkeley.

I also recommend everyone checks out my own guide to computer fundamentals for freelancers. Computer skills are essential for almost every home working endeavour, so make sure yours are up to scratch.

Action Point 2 Home Working

 It’s now time to do two things:

  • Decide what you’d like to do once you work from home.
  • Perform an honest “skills inventory” on yourself.

The purpose of these exercises is to work out how ready you are to make the leap into freelancing.

Let’s say, for example, that you want to be a freelance web designer.

If you’ve spent years working for web design companies, and have a good set of contacts and a portfolio to show, you could probably hand your notice in tomorrow and make a success of it. (Assuming you have drive, enthusiasm and strong nerves!)

On the other hand, if you have the same ambition but have yet to build your first site, you will need to do some serious learning first. You will need to put aside some time to work on some courses and build up a portfolio.

We’re not trying to come up with a masterplan here. We just want an idea of what you’re aiming for, and what steps you need to take to kick things off.

How Soon Can You Go Freelance? 

How soon you can quit your job and go freelance is a huge question. The answers to the previous exercise will at least help you to answer it.

Home working calendar

Let’s assume you know what home working you want to do, and you’re confident you have the skills to do it. When do you make the leap?

Conventional wisdom seems to suggest you should have a significant emergency fund behind you before going freelance. I read one article earlier today that referred to the equivalent of nine months’ income.

I would never want to encourage irresponsibility, and clearly you need some kind of backup plan to pay the bills, especially if you have people depending on you.

BUT…NINE months’ income in a backup fund? I’m not sure that many people have that, or ever will!

A recent survey from Inc suggested that “most Americans have less that $1000 in savings.” Non-savers include those earning well over $100,000 per year. A similar study in the UK found that 16 Million Brits have less than £100 saved.

As such, people who “wait for the right moment” to start their home working journey will probably never find that moment. My wife and I do pretty well from freelancing now, but we’ve taken risks to get to where we are.

CASE STUDY: Louise  

Back in 2012, my wife and I were living abroad, enjoying the sunshine and having a pretty sweet life, thanks to the fact she had a well-paid job and I had reasonably decent freelance income coming in.

Out of the blue, she was made redundant.

Her payoff was enough to put us in the position of being debt free, but there was zero chance of her getting another “proper” job where we lived. She didn’t speak the language, for starters, and no UK company was going to pay her £50,000 per year to work remotely from a foreign country.

She had to decide: Embrace the uncertainty of freelancing and stay living in the sun, or go running back to the security of a salary.  

Now, my wife is NOT a natural freelancer. She loves certainty, and even enjoys the structure of working for a corporate firm.

But she had no option. She didn’t want to move back to the UK at that point, so she started the freelance grind. Within six months she had regular clients, and within 12 she was having months where she out-earned me. She now makes more than she did when she was employed, and flits between event organising, PR, editing and freelance writing.

Most significantly, she wouldn’t go back to a salaried position if you…er….paid her.

My point with sharing my wife’s story is that you have to leap into freelancing at some point. Much like deciding to have a baby, it’s never precisely the right time. Save up, of course, and make sure you have an emergency fund (and ideally a line of credit!) to get you through tough times.

But fortune favours the brave – so don’t wait forever.

Action point 3 home working

It’s time to work out when you could start to work from home and put your plans into action.

You don’t necessarily need to do everything at once; If you plan to quit your job, perhaps there’s a halfway point where you could go part time and start your own projects as a sideline?

This action point will be unique to you and your family. Your savings, whether you have a partner, and whether you have children to think about will all play a part. This is about building on your previous thoughts and thinking more precisely about when you could realistically make the leap into freelancing.

The Big Jump

If you’ve got this far, you’re going to reach a stage where you need to act.

It’s the most exciting stage, and the scariest too.

The “big jump” has several sub-stages of its own:

  1. Telling people about your plans

“People” can mean your family, your friends and your existing employer.

Some will take it well; some will think you’re crazy. Some will be jealous and some will be incredulous.

This period will be an emotional rollercoaster.

If you’re quitting a lucrative job, you’ll go through phases of feeling freed and liberated, and phases of feeling like you’ve made the most stupid decision ever made by a human.

If your family and friends are supportive, you may well alternate between feeling validated and being terrified of letting them down.

The best part of this rollercoaster stage is that when you’re on a rollercoaster you can’t help but feel alive. And if you’ve been stuck in a job you dislike for a while, this will be a welcome change. Try to enjoy it.

  1. Waiting 

If you have left a job and have a notice period, the weeks between announcing your plans and leaving will seriously drag.

You can take this time to take stock and, ideally, put in a bit of advance work into your new business. You may find your responsibilities drop away a little towards the end.

  1. The final paycheck 

If you’ve quit a job to go freelance, you’ll find that your last paycheck suddenly feels more valuable than the last six that you took for granted!

If you don’t get another major dose of the fear at this point, you have nerves of steel.

  1. Getting started 

The first few days and weeks of working from home on a new business are scary and exhilarating.

Suddenly it’s down to YOU to prioritise your every waking moment. This can result in enormously productive days, and (quite possibly) days of total meltdown while you try to work out which of the 100 things you plan to do should come first.

  1. The first client/sale

Your first sale could mean the first item you sell on Etsy, the first writing job you land, or the first day of consultancy work you get. Whatever it is, it’s a reason to celebrate.

  1. The comedown

The comedown will come when you realise that it might be days or weeks until the next sale.

This is when that panic will come back. Don’t worry, it’s there to keep you pushing on.

  1. The new reality

The point at which your new home working life starts to feel normal could come after a month or a year.

The chances are it won’t resemble what you expected, and that’s part of the fun. When you set off on a freelancing journey, you never have any idea where it will lead.

Right at the start of this guide, I mentioned inspiring highs and soul-crushing lows. Once you’ve been freelancing for a year, you will have experienced plenty of each. Hopefully, despite all of them, you’ll feel you made the right decision.

Action Point 4 Home working

Have another read through the seven stages listed in the last section, and imagine yourself going through each of them.

This exercise will help you identify how you truly feel about switching to a freelance life.

Not everyone has what it takes to work from home and be the master of their own destiny.

It takes guts, determination and – yes – a bit of good luck to make it work. Hopefully this guide inspires at least one person to give it a go. Over a decade on from quitting my last full-time position, I still experience those moments of fear all the time, and even some of the “soul-crushing lows.”

But would I apply for a traditional job again? Hell no.


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About Author

Founder of HomeWorkingClub.com - Ben is a long-established freelancer with a passion for helping other people take control of their destiny and break away from "working for the man." Prone to outbursts of bluntness and realism.

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