The Price of Freelancing


Massive thank you to findingtrixie for doing the cover design and coming up with the title. To Maja for editing every single word and challenging my ideas. Lastly, my co-founder, Sabrina for responding "You want to write another one? Go on then, I'll run the business". It wouldn't have come together without any of you, so thank you.

If you use the contents of this book for any reason on your website, please link to it and credit us, Better Proposals.

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We all set out to create an amazing life for ourselves - to be the masters of our own destiny

It’s 11am, sun streaming through the window of your hotel in Ibiza. Mad night. You sit up and drink some water… euuuughh, that’s not water, it’s warm beer. You check your laptop, fire off a few emails, close your laptop and head down to the pool with the boys and try to sunbathe off this dreadful hangover.

Maybe it’s 5:30am, you’re running up the stairs to the castle on the island of Hvar in Croatia. You head back and do a little client work before meeting a client for lunch. It’s been a good month, you’ve brought on 3 new clients at your highest rate yet, perhaps you’ll rent a little boat this afternoon and go island hopping.

Perhaps you’d prefer 9:00am. You’ve dropped the kids off at school, wife’s gone to work and you head to your designated work space in the purpose built annex. You put in a solid day’s work and finish at 3pm before prepping dinner and the kids coming home. You do a few hours later tonight because you work better in the evening.

This is the dream. Three made up dreams, but it’s what we wanted when we went out on our own. Choosing when you start, choosing what your day consists of, who you work with, how much you’ll charge. That’s the holy grail of working for yourself.

So why is it that it ends up more like this?

9:37am: SHIT! I’ve got a meeting at 10am - 25 minutes away. While you’re in the meeting a server crashes and your clients are going spare. You fight the fires and promise your client the proposal first thing tomorrow. Another client calls with an urgent request and is happy to pay for it, you tell them it’ll be done.

You still haven’t eaten. Disaster after disaster and FINALLY at 1:33am, you’re done. What a day! Your head hits the pillow, you close your eyes and just as you do, BING, eyes ping open and you realise that proposal is due first thing in the morning. You drift between consciousness and sleep, feeling guilty.

Not quite what you had in mind is it?

Freelancing really does have its benefits, but it certainly has its downfalls too. The margins are pretty narrow, meaning one mistake with a client can leave you working for free, or making a mess of a proposal can leave you hungry. I’m here to help you get this right.

Why am I qualified to write this?

Before starting Better Proposals, we ran a website design agency and then a software company. The same core team we have now ran the company building custom software systems for clients. These systems would cost about $50,000 and would have maintenance costs of $3,000/month upwards. Most of us at the company worked three days a week, had very little stress and all did quality work. It wasn’t always like this though.

15 years before that, I was designing websites for $200 and I’d give them free hosting and support because I didn’t want to charge them any more than the original amount. Not exactly the hallmark of a great business. So how did we go from $200 websites to $10,000-20,000 websites then to $50,000 software systems?

Grind, mistakes, near disaster at times but they were lessons that needed to be learned along the way. Those lessons were then refined over a period of years until we distilled them down to their most potent truths. This book is those truths.

There’s little to no learning required here, whatever you put into action will immediately improve the results you’re getting. That is an indisputable fact.

Getting the most out of this book

I’m not taking time away from running Better Proposals to write this just to give you a few little tips. This book is made up of short, independent, no-waffle sledgehammers. There is no linking material, no tee-ups. These are just straightforward answers to the mystery of getting to that ideal freelancer life you imagined.

In the 18 years I’ve been running businesses, 3 of them have been spent running Better Proposals, the other 15 have been running service businesses as a web designer, then an agency, then a software company, sometimes with a team, sometimes without.

This is a choose your own adventure book about taking you from where you are now to the next step, whatever that is for you. If you’ve been up and running for a year, cool, skip the first section. If you’ve got more work than you know what to do with, skip to the part about managing work and a team.

Go get yourself a coffee, this is going to be readable in 60-minutes.

Let’s do this!

This isn't just going to be an adventure, it's going to be your adventure.

Quitting Your Job

If you have enough skill to go out on your own as a freelance designer, developer, photographer, writer, videographer or any other creative or business skill then believe me, you can replace the job you have easily.

So just quit.

Be reckless. It’s good for you.

What’s the worst thing that will happen? Save up 3-6 months money and quit. If it all goes to hell in a handbasket then just go get another job. You can probably just go back to the job you left in the first place if you really wanted to.

If you’re really worried then just get on a job site, spruce up your CV, add “freelancer for 6 months” to it and go and apply for jobs and see what kind of response you get. Once you’re confident that you’re not going to be homeless 4 minutes after you hand your notice in, then you can quit your job knowing you’re all good.

It’s worth a punt if you’re still cautious, but in the process of quitting, why not offer to do 1 or 2 days a week while they find someone else? Best of both worlds if they say yes. I would encourage you to be bold here, stand up tall and make big but reversible decisions. Your future self will thank you for it.

Take a Loan

I believe that once you’ve won your third client, you’ve done the work and they are happy, you should go to the bank and take a $10,000 loan. Now, this loan is to protect you from crappy clients.

The spiral of doom with the freelancing world is working for next to nothing, or being beaten down on price, and you take it just because you have no money.

Here’s a quick story. I had a bailiff turning up at 4pm to collect £500 (around $1,000 in those days) or take my TV from me. I was fine seeing the TV go, I barely had enough electricity on my electric meter to run it anyway, but I wanted to pay the debt back. I somehow had managed to scrape a meeting with a guy that wanted an online shop at 11am that day.

I remember sitting in that meeting listening to this guy thinking “I know this is the worst type of client to take on, but I have no choice. I’ve got to close him today”. So I went through the meeting, did the dance and took the £500 deposit, walked 6 miles home and handed the bailiff the money.

That shouldn’t have happened.

The $10,000 loan is not for marketing or paying off debt. It’s for something far more important. It will act as a buffer, there to keep you from taking bad quality clients on. We will later cover exactly what a bad client is and how to avoid them. Look at it like this. If you take on 3 clients in your first month at $1,000 each, that might seem decent but you’ve condemned yourself to that kind of work. If you quote $5,000 to your first 3 leads and they all say no but the 4th one says yes, you’re up financially and you have a better quality client.

Trust me when I tell you this is the way forward. The money is to keep you going while you’re saying no to rubbish clients and projects.

Registering your company

Disclaimer: I don’t know where you live, this is not legal advice and it’s not accounting advice, so get the advice of a qualified professional.

That said, most of these principles will likely hold true no matter who you ask. There is absolutely no point whatsoever in setting up your business properly with banking, legals, taxes etc when you have no idea if you can even pull it off.

My advice is to take on 3 clients, or get to $10,000 of business sold before you even think about setting things up “properly”. It’ll just be a distraction you can do without. That said, keep the invoices you generate and keep all receipts for what would be business expenses be it physical kit, travel, software, other freelancers.

Once you’ve done that, you can always backdate your sales so I’m not suggesting tax dodging here, I’m simply saying set it all up later.

When it comes to actually doing this, do it properly and get an accountant where you live. There’s no exception to this rule.

Everyone is put in a bucket, which do you belong in?

Human beings process so much information it’s unfathomable, but there’s also a lot that can be very quickly forgotten, because it’s not important. What colour was the front door of your second house? You knew at the time but can you remember now?

That is your selective focus at work. We do the same thing with people. It’s too difficult to actually analyse a person’s credentials, their skillset, their ability to get results so we have buckets in our minds and we’re looking for little signals to almostly instantly determine which bucket to put people in. This is where the phrase about first impressions mattering so much comes from.

Let’s say those buckets could be “business newbie”, “average freelancer” and “mini celebrity I can’t afford”.

Now, if you roll up to a situation and give off a poor impression, you have a weak handshake, you don’t control the meeting, you don’t have clients - all these things very quickly lead to you being put in the business newbie category.

How does a business newbie get treated? They get negotiated down, made to chase up or downright ignored, and beaten down until a good deal is secured against their favour. Not what you want.

The objective is to get yourself in the mini celebrity bucket so your prices are accepted, high as they are, and you are not questioned. In other words, you are accepted as an authority.

Being a celebrity

I’m using the term ‘celebrity’ but it’s really all about being that unobtainable high value option. You don’t need to be doing video interviews everywhere and have photographers stalking you in the bushes, but it does mean you need to play high status.

High status often just means carefully crafting the presentation of yourself to the business world in such a way that you are perceived to be high value. This can be done in many ways but here are some quick hacks.

Let’s get the ethics objection out the way now.

None of these suggestions are lying, in bad taste, manipulative or whatever other negative connotation you can think of. They are the same things the big players in the world do, some by necessity, some by design. We’re just going to do it by design first and necessity second. A slight word of warning here. If you very clearly are a newbie and perhaps very young and don’t have a lot of experience in general and you use these positioning ideas to present yourself as the next Gary Vaynerchuk, everyone will see right through it. There has to be an element of truth to it.

Do not answer the phone

Never pick up a call. What high value person allows themselves to be interrupted by a phone call? Have a friend with a good secretary voice record your voicemail for you: “Hi, you’re through to the office of John Smith. Please leave your reason for calling and an email address and someone will get back to you”.

What does this say? You have an office, you have staff, you’re too busy for phone calls. This is the impression you want to give off.

Always wear a suit

No matter the situation, always wear the most professional outfit you can to any client meeting. For guys, no matter your feelings about it, wear a well fitted, quality suit. For ladies, most likely a blouse with a quality, well fitted jacket. Whatever you do, look your absolute best.

This is not a good look for any kind of professional meeting How much more seriously are you going to take this guy? Wear the outfit, don’t let it wear you. Stay well groomed and speak loudly and clearly. These are the actions of high value business people which includes you, so this is how you need to present yourself.

Great photos

It’s worth investing in a photoshoot to get some smart, professional head and body shots. The few hundred dollars it’s going to cost you to get a set of quality images of you looking dapper are going to be good for several years at least so it’s worth the money. These will work great as profile pictures, author bios, great for promotion if you’re going to give a talk, the uses are endless.

Does Tony Robbins take a selfie against a door while trying to be professional? No.

Calendar availability

Don’t be too available. If you use a service like Calendly or Book Like a Boss and have your calendar publicly available for calls and meetings then make sure it’s not full of available time slots.

I’m available for six thirty minute meetings each week on the phone - that’s it. 11am and 3pm Tuesday, Wednesday and Thursday. Maybe you won’t go that far, but don’t be afraid to make an excitable lead wait 48 hours and adjust to your calendar. You’re the busy in-demand one, remember.

Name dropping

Before I started my agency, I did some account management when I was a kid for an email marketing company that had clients like Rightmove, Innocent Drinks, Yorkshire Water and VistaPrint. I never once gave off the impression that those were my clients, that is lying and you should never do that because you’ll always get found out. There is however, absolutely nothing wrong with saying:

“I ran a test once with one of the directors at Rightmove where we experimented with putting the first name in the subject line of an email and we more than doubled their open rates. That’s one thing we should definitely try with your email marketing efforts.”

Notice I’m not saying “Loooook, I worked with Rightmove!”, I’m telling a story about how we increased open rates. I just happen to be talking about Rightmove. Anything like this can work. Once you have your own set of clients with some high profile names, then you can replace some little anecdotes and name drop away.


Be heard. Being featured on podcasts has never been easier. Podcasters are looking for new content and guests all the time. As long as you can speak well, have a good story or tips to tell, it can be a superb way of displaying logos under a “Featured in” section on your website.

Niche down

It’s hard to convince the world you’re a legitimate expert in all things video or all things web or marketing. It’s simply not believable. What you want to do is focus on something that people understand and where there’s a large need. You don’t want to be explaining some weird interpretation of something. You’re not a startup looking to change the world, you are a freelancer with a specific marketable skill.

Taking web design for instance, so many web companies are just that. There’s enough business out there for you to really focus on delivering it in a unique way or to a unique kind of audience. Cheryl Laidlaw for example runs Website in a Day. She will do your entire website in a single day. You don’t leave until it’s live. Standard issue web design done in a completely unique way.

Freestyle Digital in the New Forest in the UK have since grown but several years ago they had a very clear idea of the kinds of businesses they wanted to go after. They would hand-design the sites, which would almost always be priced at £2,000. This meant the company attracted the exact type of clients they wanted, the exact work they wanted and more importantly, the work they were brilliant and most efficient at.

What are you great at? Maybe target specific industries, specific types of sites, a specific result. If you are superb at SEO then maybe focus on companies who you can get to rank locally. Here’s a good rule of thumb, if you don’t feel like you’re not “cutting off” 90% of your audience with your niche, then go harder.

Clients are everywhere. You only want the ones that are right for you

Generating leads

As a freelancer, you can only do so much work at any one time, so you need to pick the best methods of marketing yourself and attracting work that are likely to yield the best results. Some things just don’t work particularly well for freelancers, or are too difficult to get right.

For instance, you can run Google Ads to your website or do retargeting, but the chances of making that work routinely, unless it’s your specialty, are slim. It’s more likely to drain funds than anything else. Direct marketing like flyers and cold email can work but it’s a lot of effort and starts the relationship off in a way where you’re chasing a client rather than the other way round.

The ideal scenario is making your leads come to you instead of you going to them. What we’re going to focus on here is making sure your entire setup is in place for you to receive quality leads.

There’s something I want to address here. There are good leads and there are bad leads. Good leads have a budget, a clear goal, know how to buy things and want to get moving. Bad leads have a tiny budget, want free stuff, dilly dally about and generally have no clue.

Yet when you’re down and out, having a bad month and are low on leads and a bad lead comes at you, what happens? They get upgraded to a good lead because they’re the only thing going. It’s better to be doing something than nothing right? Wrong.

Just because you don’t have much work in any given moment doesn’t make them a good lead. They’re still a bad lead. Please remember this. Bad leads are absolute poison and you need to avoid them even when you’re broke. That’s what the loan that we mentioned earlier is for.


If you can’t network effectively then you’re going to struggle in every area of this method. We’ve already covered looking the part, now you are going to need to, at the very least, not hate going to networking events. BNI is a great one because it’s so well established. Go along as a guest a few times, check out the group for a cool bunch of people and sign up.

Learn to speak to people, they want to be spoken to. Be the first one there and the last one out, always. Don’t view networking as finding leads, look at networking as a way of helping others. This doesn’t mean doing free work, it means introducing them to other people. Find out what everyone in the room does, then go round putting groups together.

I remember an amazing talk by Shaa Wasmund once. She took the mic and said this:

“I have no talk, but I’m going to spend 40 minutes putting you in touch with people you need to talk to. Hands up, who has someone that if they could speak to that person it would change their life.”

First guy puts his hand up and says he wants to speak to the purchasing manager at any major cosmetics brand. A guy stands up the other side of the room and says “I’m the purchasing director at L’Oréal. How can I help?”.

Pure magic. I’ll never forget it. Here’s the thing, I don’t remember either guy, but I remember who put them together. This was 8 years ago.

Be like Shaa.

Word of mouth

Personal recommendations will happen if you do great work. You don’t need to force this but you do need to give it a nudge. Ask your clients to recommend you at a great moment like a website launch or after signing their proposal, “Do you know anyone else who could benefit from [the main benefit]?”.

You want to encourage word of mouth because a personal recommendation from a trusted source is always going to carry significantly more weight than anything else. There’s no better way of encouraging this than simply doing what you are promising. Not over delivering, not under delivering. Just deliver exactly what you’ve promised in the timeframe with no exceptions.

Results will always speak for themselves.


This is never going to be instant but you want to try and rank for “[service] [location]” ultimately. This is going to serve you leads in the long run. If you are still in full-time work, then get your site online as early as you can and start putting content out there to get yourself ranked.


This is a great task to outsource as a little bit of practice for finding dependable workers who can handle simple, repeatable tasks that require little skill and a sprinkling of common sense. Get yourself listed on 10-20 local and national listings. It’s a good little boost for SEO, some of these directories aren’t bad and you might get the odd lead or two. In the early days, it’s worth a half day smashing this out.

Side benefit of doing this is you’re going to get asked for your website, descriptions, images, links and all sorts. It’s great to go through this exercise. Apart from anything else, it’s a boring as hell job so if you can stomach this then you can pretty well deal with anything.


Facebook can be enough of a lead generation tool in itself if you do it right. Quality photos only, so scroll right back to when you were 18 and drunk and take that picture of your ass offline. This is your new LinkedIn now so that stuff has to go.

Get yourself in some industry groups and network online with some like-minded individuals. I suggest posting regular material which helps your target audience get a micro-step closer to their goals. If you want to learn how to post, I suggest following Mitch Miller’s Facebook page for quality material. No-one I see on Facebook uses their personal profile to such brilliant effect as Mitch. Over time, you’ll accumulate somewhat of a tribe on your Facebook account.

There’s a lot to be said on this and someone like Mitch is a great place to start. Another great place is's Self Employed Guide. It's full of tips, tricks and ideas on how to manage life as a self employed person.

Once you have a lead

This is where you’ll lose it if you don’t play it right. It’s this moment here that your personality is going to shine through. Is the positioning you’ve done of yourself and your personal brand real or are you fake?

It’s a test.

Do you call them the second they ask you to or do you make them book a call in your online calendar?

Do you get in the car and drive to them for a meeting at a time and date they set just because they asked to see you, or did you make them have a call first to work out if a meeting was necessary?

I could go on. The important thing is whatever rules you decide you want to enforce, you must enforce them every single time. You are not going to put off a good lead by making them wait 24 hours for a phone call. You might put off a bad lead which is exactly the point.

Be the person you need to be to attract the people you want.

When you get a lead, no matter how your enquiries come in, you need to get them on a level playing field so they need to fill in an application form of sorts. You can make this as strict as you like but the point is to get them to jump through a hoop. It doesn’t have to be a big one but it’s a vital step. It’s a requirement to make them respect you and get into the habit of following your rules. You can use something like Typeform for this. It's free.

This will also indicate their seriousness. It can simply include info like business details, budget, any key project completion dates. Basic stuff, but it’s the simple manipulation of getting clients to give you information on your terms that’s important.

Once that is done, assuming you’re happy with the information in their application, you can set up the call. Send them a message with the great news that it looks provisionally like you might be a fit, and you’d love to arrange a time to speak.

From there, you ask them questions on the call that you need to know in order to write a proposal together. Get an idea for their goals, dig into those timescales, who is responsible for saying yes, gather any key dates around that decision, find out specifics of what they’re after, find out in their words what would make the project a success.

Once you know these things and have them written down, only then can you think about putting a proposal together. Now, some people will want to run this call, that’s just in their nature. If you get off the call and you don’t have the answers you need, it’s going to look really weak.

The easiest thing to do if they start trying to take over is just say;

“Absolutely and we’ll get to that shortly, do you mind if I just whizz through some basics first? After that, I’m all yours.”

Only a ridiculously unreasonable person would say no. If they do, red flag. See ya.

Play to your strengths

We all have unique advantages. You might have opportunities, skills and experiences others don’t have and vice versa. Let’s be honest, some of us scrub up better than others too. Use this.

If you are an outgoing, confident person, go and speak at events. If you are a great writer then maybe write ebooks for credibility and something to give away during follow up.

Maybe you’re one of the few that can talk to a camera and that’s the thing you do well, perhaps you could lead with doing Facebook Live videos. Likewise if you have a well connected Uncle then work his contacts.

Your advantages are your advantages. Use them.

Now once you have your lead what now?

Running a client meeting

There's a lot riding on a good client meeting but fortunately, people are so bad at them it doesn't actually take much to leapfrog everyone. A great client meeting has two outcomes:

  • You get the information you came for
  • They are excited

If those two things happen then everything else will fall into place.

Getting the information you need

It sounds obvious but actually asking questions is key here. It's insane how many conversations I've had with freelancers where they let the client dictate the pace of the meeting and leave with more questions than they went in with.

In order to be able to ask the questions, you need to set the pace and run the meeting. There are a few subtle things you can do.

The first is to have the meeting at a location that suits you. You set it. Unless I needed to, I'd always meet in a hotel reception area and get there 40 minutes or so early. That way, you're not rushing, you've had a drink, you know where things are like the bar, reception, toilets etc. This gives you situational confidence that they likely won't have.

The other reason is it shows what kind of person you are. Try and imagine the scenario walking into a coffee shop vs walking into a smart hotel receiption area?

What kind of impression does this set? Isn't this the kind of place you'd rather meet someone?

Here's the funny thing, the price of coffee is only marginally more expensive, if at all, than the average coffee shop.

A good rule of thumb is to cut off the smalltalk when the waiter or waitress brings the drinks. It's a good little cue and all you need to do is just transition and say:

"So I can understand your project better, I've got some questions, I'm going to go through this first and then any gaps, we can discuss after - that ok?"

Tell them what you're going to do then a little token "that ok?" at the end. it's far more commanding than asking first.

Now you can just ask your questions and write down the answers in their exact words.

You should have a list of questions that you need in order to put the proposal together. You should be finding out what the goals of the project are, what the main problems are and what the cost is of not solving those problems. If you're in the digital, web or marketing space then get their metrics like conversion rates etc.

Once you're happy you've got your answers then you're all good. You can let them rattle on for as long as you have time for after that. Once you've had enough just wrap up, always cover the drinks and stay exactly where you are.

Now it's time to write the proposal

Proposal writing shouldn't be a challenge. There are really only two things that cause them to be difficult to produce:

  • Not knowing what to say
  • Spending ages getting the formatting right

Now, if you've worked out in advance what information you need, you've just conducted the meeting and have just written down the answers, you shouldn't have any trouble figuring out what to say.

Knowing what to say in your proposal

Stick to your proposal template and don't invent parts of the proposal just for them. That's what will take ages and mess up the flow. The most important part of the proposal is the introduction.

The introduction, or executive summary is the part they will read first and read properly. Everything else generally gets skipped over, this is why it's so important to write it immediately after the meeting.

The details will be fresh in your head. All you want to be doing in the introduction is writing the goal of the project and state it in their words. That's your headline done.

You then want to write two short, punchy paragraphs going into a little more detail but really, this should just be using their words you've written down from the discovery session. In school we were taught to "put things in our own words", maybe you were taught the same.

Don't do that here.

You want to use their exact words and phrases - even if you wouldn't use them. That is the part that gives them the feeling that you were listening and "get it".

If you spend 30-40 minutes writing the proposal, which is all it should take, half of that time should be spent writing the introduction.

The rest of the proposal is relatively straight forward. The specification, or the part where you describe what you're going to do should be fairly templated already, you're just putting their specifics in.

Slotting in a relevant case study is super easy as you start to build up a library of them. Lastly, pricing shouldn't take you long.

A common mistake is to put loads of technical information in the pricing table, don't - keep it simple. Save the technical stuff for an FAQ section.

Getting the formatting right

If you're trying to send a proposal in Microsoft Word or InDesign, just stop. It's a total and utter disaster and will take you hours.

Some things you can do without spending money, your proposal writing shouldn't be one of them. There are plenty of online proposal systems, Better Proposals just happens to be one of the market leaders in the proposal software space.

You shouldn't be spending your time formatting proposals. It takes hours if you're efficient and have a system. If you don't, it can easily be half a day gone.

Get yourself a system sorted. Better Proposals for instance has over 100+ templates for different industries and sub-industries, client sign off, contracts, brochures and more. Use this to your advantage.

All you need to do is take one of our templates, customise them a little bit to suit your business, maybe change some images or colours then it's ready to be used. All you're doing when you've had your client meeting is filling in the gaps and sending it.


In the 2017 Proposal Report we looked into what happened to your conversion rate and time to sign if you send the proposal quickly. It turns out if you send your proposal within 24 hours it gets signed in an average of 6 days vs 10 if you send just 1 day later.

You're also 25.9% more likely to close the deal if you send the proposal within 24 hours. This is enough of a reason to get it done quickly. Not only is it much easier to write but it's better for your bank account.

Data taken from Data taken from

Great relationships are built on clear communication and setting expectations.

Managing Expectations

When you first meet someone, there are no rules, you make them up between you. You’re trying to work out who should adjust to whose schedule, who has the higher status and value and thousands of other things.

Many of those things can be handled by “feeling your way” through an interaction but you can’t do this with managing expectations. It seems awkward to say to someone “Here are some rules about dealing with me”, but in a way, that’s what needs to happen. Is it okay for someone to call you at 3am with a silly question? Of course not, but basic etiquette should handle that. Ok then, but what about calling you at 7pm on a Friday night? That’s not totally out of the question so is that okay?

Yes, cool, tell them. If not, you need to make that clear too.

A simple enough way to do this is simply say, “Just to manage your expectations, there’s a couple of things I’d like to run by you”. The main things like timescales to get things delivered by are handled in the proposal - they’re easy and straightforward. Business relationships can often be strained because you have not responded to communication when your client thought you were going to.

Now this doesn’t mean respond in seconds, it means let them know you do all your email at regular intervals several times a day so it’s unlikely they’ll get an instant response. It keeps them in the loop.

It might seem like between making them fill forms in, abiding by your calendar, setting out rules they need to follow, that you’d wind your clients up. Quite the opposite. Our brains don’t have time to work out why someone works the way they work, we just assume that if it’s different to us then it’s for a reason.

This all assumes you are incredible at your craft and when you deliver, they lose their mind with excitement. That has to be the balance. No-one’s going to put up with strict working rules and a substandard product.

When things go sour

Things will go wrong. You will fall out with clients, it will just happen from time to time and to pretend it won’t is just deluded. There are many things you can do to prevent this. Keeping communication singular and organised, and setting expectations are two great ways of keeping things on track.

Another excellent tool to have up your sleeve is milestone sign-off. A simple example might be the design portion of the website and the development part: there’s a clear divide there, and it makes complete sense to get the design signed off before starting the development. If you were to do this, the client would have to agree the design before proceeding.

Let’s assume the worst. Client signs off the design, then changes their mind. Perhaps you don’t have a signature on paper, but you might have said to them verbally that they can’t change the design past this point. A verbal promise is easily forgotten, and in your client’s mind: your job is the project, so what does it matter if they request another tweak or two?

If you get it signed off as done and unquestionable, they might still ask for design changes at a later stage, but the point is they know they are asking for a favour. This puts you in a much stronger position. You might make an exception and allow it, you might add a week to the timescales, you could charge them extra but it’s all fine. They are just grateful it’s possible. These are your rules of business, they need to play along.

Milestone sign-off at key stages will save you from almost all arguments. Another method if things really are heading south is to do a “final snag” list. So if they’re pushing back with change after change, just tell them to go through everything, snag it all and then send them a small agreement detailing the final snags and get them to sign it.

This starts to draw a line under the problems, and chunks things down. Instead of arguing over the whole project going wrong, you’re splitting it up into little bits. It makes it pretty hard to go completely mental when all you’re arguing about is the shade of red being slightly wrong.

You can do all of this in Better Proposals, so you're sending your proposals, contracts and milestone signoff from the same system. Keeps you organised, looking professional and keeps your client in order.

Look, fixing broken relationships is tricky so it’s much easier to prevent it from happening in the first place. If the worst does happen then don’t hide behind email. Get on the phone and LISTEN. Make notes with paper and a pen and really understand what is frustrating them. Let them get it all out then repeat back to them their issues and explain what the best way forward is.

If you were born after 1990 and grew up in a world of texting as a primary form of communication, it’s possible this is not going to be natural to you but it’s something you’ll need to get good at.

Firing a client

There’s no scenario where everyone wins here. If you need to fire a client and you’re all square with them financially and work-wise then it’s not too difficult. Just keep it short and sweet, explain you’re going in different directions and while you were a good fit in the beginning you’re not anymore. Then give them everything, all files, footage, whatever media it is. Just get rid of them.

If you drag it out, trying to get some settlement from them, it’s just going to murder your business, your time and emotional energy.

If you are mid-project and it’s truly not working, they’re not listening, not following your rules and ideas and you need to cut them off, then it’s slightly more tricky but it’s a similar approach.

It’s best to take a three strikes rule here. If they won’t play ball with milestone sign-off, won’t play ball with the snag list sign off and it’s all a mess at the end, then tell them you’ll forego the balance and you’re cutting off communication with them.

Always sleep on decisions like this and don’t argue. Just sleep, make the decision, action it with a firm email and that’s it. You must stand your ground here. One of the potential titles of this book was going to be “Don’t be a little bitch”. It was moments like this with nightmare clients that inspired me to think of this apt title.

Think about it - there are millions of potential clients out there. Your job as a freelancer is to constantly filter that list so you always have the best quality clients.

Getting paid what you deserve isn't a right, it's a game plan


There are 4 ways to charge people:

  • By the hour or day
  • Costs + a markup
  • Commission
  • Value

Some industries have simply decided how you should price. For instance, the video industry seems to want everyone on day rate. That doesn’t mean you have to, in fact, it’s even more a reason not to charge like this.

Charging on time

Let’s look at why charging on time is awful. The incentive is for you to take as long as possible. If you’re happy with $50/hour then why do you care where you get that $50/hour from. There’s no incentive for you to finish the job quickly. Some people say “Well, I’ve told them a maximum hour limit”.

This makes it even worse. So you’ve capped your earnings but if you use your skill and experience to finish the job quickly then that’s their gain. Huh?!

Stop charging for your time. It makes zero sense.

Costs + Markup

This makes an element of sense for some businesses but it’s still so unbelievably limited. Say you’re a flooring company. You have the hard costs of say, $1,000 of flooring, plus labour of two guys for a day at $200/day.

So your total costs are $1,400, you then charge the customer $2,800. You know you’re always in profit, so it’s safe. The same logic doesn’t apply to most service businesses because it’s mostly your expertise and a certain result you’re selling, not something physical.


Again, in certain businesses this makes sense and does get closer to how we should be charging. In the property and real estate world, you charge a commission of the sale price. It’s like charging based purely on results, but with the final amount directly linked to the amount you’ve made for your client. It is therefore in everyone’s interests to make this as great as possible, so both you and your client have the same goal in mind.

Online advertising companies charge a percentage of the advertising spend, which makes sense to a degree. The bigger account you’re managing, the more time it needs spending on it.

What you absolutely should not do is charge depending on someone else’s results when you can’t control it. Commission of sales on an online shop would be an example of something to run away as fast as you can from. There are too many variables there to make it work.

Value Based Pricing

This is where you’re not charging by the hour or day, you’re charging them based on the amount of value they will get from your service. This works better for some industries than others but ultimately, this has and will always make the most sense. It means you can benefit from the skills and experience you’ve picked up over the years. It means you’re not punishing your client if you make a mess and need to mop it up.

Most people at this point can get on board with the idea of value based pricing, but have no idea how to do it. I will dispel this myth for you. It starts with questions. If you ask the right questions, everything else falls into place with little effort.

You need to genuinely work out what the value you can offer to the client is. This is how you make your case. If you know through a series of questioning that they are likely to increase their monthly revenue by $76,000 and you quote $1,000 to do so, then you’re not only massively under charging for your skills but you’re also not pricing in line with what makes sense.

Let’s go over the questions you should be asking. Of course this depends on what you’re selling, so adjust accordingly. If we assume I’m selling a new website, here are some things I want to know about the current website:

  • Current traffic levels
  • Current conversion rate to either a sale or to a lead.
  • If the conversion rate is to a lead, I want to know the conversion rate from lead to sale too.
  • Average transaction value.
  • Rough average profit percentage on each sale.
  • Where they feel they lose people along the funnel most.

I could go on but with just the answers to these six questions I can tell roughly what their current site is making, what money they have to spend on fixing the issue, if it’s improvable and if so, by how much.

All of this leads me to being able to present a case for why this new website could cost them $10,000, when otherwise I’m just plucking a figure out the air hoping it fits. Asking these questions also allows you to call things into question, so get good at working through the maths from lead to sale if you’re in the digital space.

For example: Let’s say they tell you they have a budget of $2,000. Let’s also say they’re doing 10,000 unique visitors to their website every month with 1% converting to a lead (100) and converting 30% of those (30). You know they make around $500 profit on each sale so you can reasonably assume they are making 30 x $500 or $15,000 a month.

Does $2,000 seem reasonable if you could get their conversion rate from 1% to 2% - effectively doubling their turnover with relative ease and you had previous case studies to back this up?

Also watch timings - the above scenario would means the client could get their money back on their investment in you in about two days. Wouldn’t it make more sense if the price was maybe $12,000 or $14,000 to start with - to get that initial 1% boost, then continue working to improve it further over the following year?

This is value based pricing. Charging based on the value you are going to provide and not on the amount of time it takes you or a markup on costs.

Taking Free out of Freelance

It does seem that a freelancer’s favourite thing to do is work for free. Let’s try to avoid doing this shall we?

Now, there are two common occasions where you might end up doing work you’re not being paid for. Upfront, and at the end. There are other times, but let’s focus on those two being the most common.


This is much easier to avoid. If you have your positioning in place you generally won’t find this crops up much. People assume you won’t work for free so they don’t even attempt to do it. What some nasty clients will do is try to get you to do a “mockup” or some part of the job for free in advance. In design this is called Spec Work, or put properly, ‘speculative work’. I’m not sure about you, but I don’t like the word speculative and work being in the same sentence together.

In the freelance business you need to be on “red flag” alert. There are certain things that indicate without any doubt that someone is going to ruin the next few months if not years of your life. The problem is, some of these people have serious money and are happy to spend it but that doesn’t make them a good client. Being asked to do work upfront is a very clear indicator that someone doesn’t understand how to buy creative services and these are people you should steer well clear of.

If you do get asked to “show what you can do” or “give us a little taste” then you simply say the following: “I’m sorry, we don’t do free work. If you’d like us to work with you then we’d love to work with you too. If you’re still unsure because you’re not certain we can get you the results you’re looking for, then let me know what it is you’re unsure about and I’ll give you the reassurance you need”.

If they push then it just strengthens the case for running. If they push back at that point then you know they’re just after free work for ideas, then will probably give it to someone else to finish. You just have to be harder in your stance at this stage.

At the end

This is where it’s messiest but fortunately it’s far easier to fix. If you’re not getting milestones signed off yet with Better Proposals then this will help massively in keeping projects on track and not having them be a hot mess by the end of the project.

One thing that has served any successful freelancer well or any agency for that matter is the concept of a “Phase 2 list”. Now, this is best mentioned as early as possible and positioned as something positive. We would say things like this:

“As the project unfolds you’ll notice things you want to change. This is normal and expected. What we do with those things is put them on the Phase 2 list. This means we can keep to spec and get the project done in the timeframe and for the amount we’ve quoted you. We build in time to work on the Phase 2 list immediately after this project is signed off and finished. We’ll price it up when the project is done, then you can cherry pick the things you want and just remove things you don’t.”

That statement will get you out of such a jam. Any request that comes in you just say “Cool. I’ll add it to the Phase 2 list”. It’s such an easy little hack. The earlier you mention it in the process the better. We stuck it in the proposals in the end because it was almost a selling point.

That is the easiest way of getting out of doing free work at the end of a project. Without the Phase 2 list you just end up in this spiral of working for free in the hope the final payment comes.

Another hack is payment terms. If you leave a massive 50% at the end then what you find happens is that you end up “trading” the last few snags for that final payment. The best way to do this is move more of the money upfront.

So if it’s a website that’s say $10,000, you would charge 50% when signing the proposal then 25% when the design is signed off. Possibly even another 20% when the raw functionality is done, leaving just the remaining 5% for snagging.

This means worst case scenario, your client can only withhold 5% which isn’t the end of the world.

Managing Finances

Get an accountant and don’t skimp on this. You don’t need to go mental but don’t get a bookkeeper who thinks they’re an accountant. Get a real one.

Keep your personal expenses and your business expenses separate. Keep your receipts and use Xero, Freshbooks or any reputable online accounting software. You can do this with spreadsheets but it’s simply not worth the grief for the sake of $20/mo or whatever these systems cost.

Some things you can do on the cheap, managing finances is not one of them.

Work out roughly what percentage of your income you need to put aside to pay taxes and do this the second it enters your bank account, no matter how hard up you might be. If at the end of the year you’ve overestimated - fantastic! But whatever you do, avoid underestimating. The last thing you want is to get to deadline day and find you need to pull $5,000 out of thin air.

Thinking beyond day-to-day management of your business, you need to think about life after work or a very rainy day. There are many ways to do this but some automatic way of paying into a fund or pension that just happens without you thinking about it is the only way forward here. Relying on having a huge business in twenty, thirty, forty years time is insane, you can’t possibly predict this.

There’s something called the Own The World fund by Andrew Craig. You can start by putting $100/mo into it and it buys up a mix of everything, stocks, bonds, crypto, precious metals, gold, silver etc. Advantage of this is things might take a dip but there’s enough variety in there that it’s never going to tank. For instance, when stocks dip, metals, gold and silver usually go up in price.

This is not my area of expertise but you want to keep the work you do on finances to a minimum. Get a system like Xero, get a good accountant and invest a small but regular amount in your future.

Sick Pay

You’re not going to be getting paid when you’re not able to work. You’re also not going to get paid time off, you’re not getting insurances automatically paid for, and bad news, there’s no cover for those times when things aren’t going well.

This is why your rate can’t be compared to the salary of a similarly skilled worker and is another reason why hourly rates aren’t great, because your potential client won’t be necessarily comparing apples to apples. They’re potentially looking at $20/hour as a designer’s hourly rate from a salary perspective, not taking into account that you’re not getting sick pay, a guaranteed amount of money each month and many other things. Your revenue needs to make up for this shortfall.

You need to build this into your pricing. You don’t necessarily have to have a pot of money reserved but you totally should have enough money coming in from each project to cover for times when things aren’t going great.

Another thing to consider is the cost of hiring in people in your network to help you get a project over the line if you’re ill or need to take time off. You need to accept the fact that anything can happen, like accidents or illnesses, and it’s entirely possible that there might be weeks where you can’t work. You may not need to do anything about it right now but it’s possible it’ll crop up in the future.

Just be aware.

Working on your craft while keeping the machine running smoothly is the holy grail of freelancing

Software to run your business

New software to techie freelancers are what shoes are to 19 year old teenagers. It’s known as “Shiny Object Syndrome”. Having the latest and greatest piece of kit is cool but what’s cooler is having a well oiled machine of a business and that’s the focus here.

There are plenty of places that allow you to get lifetime deals on new startups but many aren’t complete, or even really bug free. They can become great over time but the best thing I can suggest is to not worry too much about racking up monthly fees and just get the software you need to run your business.

Accounting and invoicing - Don’t skimp here. You can use Wave which is free. Freshbooks, Quickbooks and Xero are the leaders here and there’s little reason to deviate from these.

CRM - As a freelancer you probably don’t need a full-blown CRM to start with, but Salesflare is what we use for partners and proposal design services. HubSpot CRM is free and will get you by for years to come.

Proposal Software - Better Proposals is the best value proposal software for freelancers. There are others out there but on the most part, our Starter plan is designed for freelancers and it’s the perfect plan.

Project Management - Trello is free, there’s Basecamp, Asana, Plutio. There are more project management tools these days than projects so pick the one you like and just commit to it.

If you need anything else, make sure you actually do require and not just want it, and that it justifies its place and cost.

Project Preparation

I once interviewed Cheryl Laidlaw, who runs Website in a Day. She builds websites for $3,000 and literally does the entire thing inside a single day. I mentioned her earlier.

She spends a few hours spread out over a few weeks in the lead up to the date getting the client’s content together, sorting domain names and all the technical stuff and in one single day, she blitzes the entire site.

The only way anyone would be able to do this is by being super organised, having set rules, checklists and processes and not deviating from them. By not deviating, you’d of course limit the kind of work you can do which is a good thing.

The closer your work is to that of a production line the better. It never will be completely systemised and your art will always be front and centre without needing to be compromised. You want your work have single focus, be process driven and stick to the task at hand.

The easiest way to do this is make a ‘No list’. These are the projects and tasks you can’t do a world-class job at or fall just outside your expertise. Take pride in your ‘no list’. It makes your ‘yes list’ far more powerful.

We’ve covered what your sales process should consist of and that should set things up nearly perfectly by the time it comes to actually starting your project, but it is very much worth spending a little time making a few checklists for repeatable tasks that crop up time and time again. It might seem like a waste of time when it’s just you in the business and you don’t need to delegate. However as your business grows you’ll come to realise, these things could save you time, money and grief later on if you run into issues.

Get agreements signed

We did cover this earlier but it deserves its own section. If you work with a client and you don’t get a contract signed, you are just asking to get yourself in trouble. There are many free or cheap contracts easily found online. They’re not as good as having something written specifically for your business but they are at least something. There’s simply no excuse these days, especially with tools like Better Proposals which allow you to use your sending allowance on contracts too.

You’re a professional. This might sound harsh, but act like one. Professionals send contracts to their clients and they don’t start work until they are signed. Any deviation from this practice will leave you not just looking weak but also legally vulnerable. It will hinder your chances of being able to smooth over any issues, get your ideas across and retain that high status you’ve worked so hard to earn.

If you don’t think a client is going to sign your contract then you need to be asking yourself why. Is it not perfectly normal business practice to sign a contract before working together? Of course it is so why do you think you are the exception to this? You need to accept that it’s normal behaviour, it’s expected and not doing it makes you look inexperienced.

Outsourcing non-core tasks

To start with, do your bookkeeping, there’s no sense outsourcing this. At a certain point though, you need to get rid of this task. It’s mind-numbing, it’s boring, it’s uninspiring and your time is much better spent doing something productive, or taking a walk.

It's better to have 20 productive hours per week while paying somebody to handle mundane admin tasks, than to do the same 20 hour productive week mixed with you trying to do those repetitive admin tasks. Not only will your head be clearer, but those people are specialists and will do a much better job than you.

Bookkeeping, accounting, research, writing, list building or anything repeatable and not your core skill should not be done by you. As a highly paid craftsperson, you should not be doing these things and wasting your time. Stick to what you are good at.

Building your team

This is absolutely crucial. You might not realise this straight away but as the years roll on, you’ll realise how absolutely vital it is. These people will help you if you’re stuck, you can pass work to them or bring them in, and you can do the same for them. You don’t have the stability of a business, but this creates that in effect.

Don’t see these people as competition, see them as teammates that you don’t have to pay. These are the people you can run joint events on with, attack bigger projects with, pass work to and from.

Invest in this, be cool, help others, grab coffee and beers, share tricks. These are your family. Look after them and they will look after you when you need it most.

Know your time

You will have busy periods, slow periods, mental periods. Know what these are for you. We found that October was completely bonkers from a sales perspective because all our clients wanted stuff launching Jan 1st. In October I’d spend my life in a suit and travelling from meeting to meeting. Once we were done selling though, it was amazing.

Not a suit in sight, weeks on end in dressing gowns smashing the work out, no restrictions, all calls handled between 3pm and 4pm, it was pure glory - the best part of the year.

July and August, everyone’s on holiday so prepare for this because you’re unlikely to get too many deals done over the summer. Maybe use this time to improve your processes, spruce up your website or do some outreach.

This was us when we ran our agency 10 years ago. How different are those things now? Probably not very. It probably applies to most creative businesses these days too.

That’s your year, but do you have a period in the month when it’s busy/quiet? What about your week? Are Mondays filled with customer service type stuff and Fridays with last minute fixes? Cater for that.

This is a lonely game. Take measures to stay healthy and happy.

Working from home

As a freelancer you will likely start out working from home. This is totally cool and most freelancers I know do the same. To start with if you haven’t been doing this before you’ll just be in a state of pure joy for the first few months.

Lunch when you want, play games whenever you want and finish work whenever. As long as you get your work done, it’s bliss.

Until it’s not.

At some point, the lack of human interaction will start to grate on you, you begin to lose some of your social skills somewhat. It can be a bit weird.

I remember about 10 years ago I’d been working flat out on my own since October. It was the busiest it had ever been and I was burning the candle not just at both ends, I’d chucked the candle in the furnace.

So to illustrate how much work I had on, I’d switched off or removed every single clock in the house. If I couldn’t remove it, I simply messed it up completely. It was bizarre - I’d be working away thinking it was maybe 8 or 9pm and it would be 4am. I’d eat when I was hungry not because it was lunchtime. I slept when I needed sleep regardless of the time.

So it’s December 23rd. My Dad calls me and asks if I’m coming over for Christmas in a few days. At this point, apart from thinking it was the middle of November I had obviously not done any Christmas shopping. I finish what I’m doing, get in the car and drive to Churchill Square Shopping Centre in Brighton.

I park and there’s this staircase that just comes up in the middle of the shopping centre. I walked up this thing, stood at the top and literally freaked out. I had barely seen a human for months and here I am in a shopping centre full of people the day before Christmas Eve.

I turned around, bolted back to the car and went home.

“Dad - Christmas is cancelled. I’m scared of people. I’m staying at home”

Slight digression - but don’t do that to yourself. It sounds like a funny story, but working long, solitary hours is not particularly healthy.

My recommendation is to make sure you take 2 days out the office each week. Even if it’s just for a few hours. Just the act of going to work on something specific outside the house, ordering a coffee, interacting with a cashier can be the little things that bring balance to your otherwise screen-infested week. Getting yourself away from your screen is so important when it comes to retaining perspective, getting new ideas and letting existing ones simmer in your creative brain.

During these times, resist email, don’t have work calls. You’re not going to annoy a client by not replying to an email on a Sunday night. Be brave - it’s your life, your work diary so make it work to suit you.

The rest of this chapter might seem like it borders on suicide prevention at times but I feel incredibly strongly about the fact that this stuff is important. Too many years like this and it can do some weird things to you and trigger anxiety when you otherwise never had that issue at all.

I’ve been fairly lucky in that I’ve been able to maintain a solid life working from home for 18 years but I’d be lying massively if I said I hadn’t at various points hit burnout, been massively unhealthy and struggled. Please look after yourself and remember that because you don’t have the structure that a nine-to-five brings, you need to create that proactively. If you don’t, you’ll run into trouble.

What a standard nine-to-five work setup also provides is the societal norm, a comfortable daily environment people are familiar with, and a set of unwritten social rules to play by. There’s a daily commute and therefore a reason to get up in the morning - you’ll face the sack if you miss that train and arrive after 9am. There are classic roles in every office. You’re the new temp, or the office joker, or the strict boss. Get ready to throw all of that familiarity out of the window if you work for yourself.

There was a recent study done by Upwork called Freelancing in America that predicted that the majority of the workforce will be freelance by 2027. Whether that happens or not, who knows but it’s clear which direction we’re going in. You’re going to be a part of that.

When you don’t want to work today

This happens. It’s a case of just facing it and also facing the options you have which are to embrace it or power through.

It really comes down to the work you have on and any impending deadlines. If you are flat out with work and there’s no time between you having this feeling of not wanting to work and the work needing to be finished then you’re going to have to suck it up and crack on.

We all have times when we don’t want to work but you’re paid to get a job done so you need to find a way to accomplish it. I don’t have a step by step method, but I have a bunch of things I vary to keep it exciting to push through.

If it’s late at night I might make myself a coffee, put my headphones on and commit to working all night. It’ll never happen but you breeze past the bit you were stuck on and regret the coffee when you try to sleep. The regret is part of the process.

I’m hugely into dance music, so watching sets that are a fixed length of time are great. They’re usually 60 minutes upwards which can be just what you need to get past a certain bit of work. Invest in good headphones and learn to enjoy working to music if that’s your thing.

Set the alarm for some insane time in the morning like 4am or 5am. There’s something primal about beating the sun up and making a strong start to the day. This will usually be enough to kickstart you into having a great day and blitzing past whatever is holding you back.

Another method I like is the pomodoro technique which is working solidly without interruption for 25 minutes, you then take 5 minutes to check your phone, email etc then reset the 25 minute timer again. It’s great when you have a lot to do.

Feeling guilty taking time off

Where does guilt come from? It’s a feeling of not doing your part towards something and the expectations society holds over you. So if you are feeling guilty about not working hard enough, is this because you’ve been slacking recently? If you know your output is great and you’re doing your bit then release this feeling of guilt.

It’s completely okay to go to a photoshoot, take the photos, have a day off and edit them the next day. Try to adjust your guilt-o-meter to look at the overall output and not your daily activity. As a creative it’s important you have time to yourself to reflect, think up new ideas and do things on your own time.

Don’t stress it.

Dealing with loneliness

This is something I suffered with a lot back in the day before my co-founder moved to Brighton. We worked together more, needed more discussions and actually worked as a small team on a lot of tasks.

Prior to that it’s a very real struggle and if not managed properly can leave you being a pretty miserable human being. The best way to manage this and mitigate potential issues is to keep doing things, keep aside ‘you’ time to have nights at the pub with your friends, date night with your partner or Tinder time if that’s your thing. Keep the human interactions up, you’ll need them. Try to get out the house at least once a day. Even if it’s just to go to a coffee shop for half hour and come home. It’s something.

Consider finding a co-working space you can go to every now and again. Personally I don’t like them, I prefer working from a hotel bar. I find it much nicer and the upmarket environment makes you feel good which can really come across in your work.

As someone who spent about seven years working almost in solitary confinement, take it from me - you need those moments. Go out, talk to a stranger, go for a walk, swim in the sea, play a sport, watch your sports team play in a bar not at home, eat out.

Build in those little things you can do to break up your day, experience a little human interaction. It’ll save you in the long run.

There comes a time when you need to make a choice about the direction you go in.

Let’s set the scene, you’re a year or so in. You’ve had some superb months, you’ve had some rubbish months but you’ve got some great clients and things have settled down somewhat.

It’s not to say you’re not going to have good times and bad times again, you absolutely will, but if you stay where you are, you’re going to be a lot more susceptible to coming under serious pressure during bad months.

It might seem like carrying on doing what’s got you this far is the safe option but the truth is staying where you’re at simply isn’t an option unless you’re happy to run the risk of complete failure. Let’s assume you’ve done $30,000 in your first year. That is a great start but is obviously not going to fund your dream lifestyle.

Worse yet, with that kind of money you’re literally weeks from having to get a job again or borrow money to survive. Of course this assumes you haven’t saved 8-10k of that money but I want to illustrate that as a freelancer, you need to create your own financial stability.

You need to add a layer of protection in so that if you do have a rough couple of months it doesn’t take you to the brink of disaster. To do this you need to go one of two ways, you either need to stay freelance but build it into a mini business, or grow into an agency.

Staying freelance

This is completely viable but there are some truths that need to be faced. If you are going to increase your income and stay on your own, one of three things needs to happen.

  • Increase your pricing (and probably the size of client)
  • Speed up the production side of things
  • Or - a combo of both

Increasing your price is undoubtedly the easiest thing to do. There’s a good to fair chance you have improved massively in your ability to win work, present your case and deliver on your promise. You probably have a range of case studies at this point and all of this means you can probably charge more right now.

You’re likely also in a much better place to start going for clients bigger than the ones you’re working with currently with no issue at all. The things that matter to bigger businesses are things like well written and presented case studies, presenting yourself professionally with a quality proposal, and being able to assess the result they want with historical proof you can deliver.

As you work with bigger companies, the people you’re selling to aren’t typically the business owners anymore. This means their job is to not make a mistake in hiring you. They’re not concerned with the cost as such. If they think you are the safest bet, they’ll go and get more budget to hire you.

They’re not going to choose someone that fits the budget when they’re not convinced about their ability to deliver because they’ll be risking their job.

The other method is by speeding up your ability to work. This is almost always possible. Take a step back to look hard at areas that are time consuming and analyse where there might be room to streamline some processes.

Now you have a much clearer idea of what you’re trying to achieve, it’s entirely possible that you could outsource some of the repetitive tasks eating up your time. If you’re a web designer, maybe you could get someone to put the content into the content management system for you. Or go one further, use something like Content Snare to get the content from your client and have your virtual assistant load it into the site.

Taking this further...what is stopping you from getting someone to set the sites up, (assuming you’re using WordPress), install the list of plugins you suggest, set up the page names while you focus on the design and dealing with the client.

If you’re a writer, perhaps you could outline the strategy and partner with a cheaper copywriter to do the grunt work and actually write it up. So you suggest the strategy and perhaps any finishing touches and that’s it.

If you’re a photographer maybe you forego the editing so you can shoot more. In the video business? Maybe get a junior editor to rough cut it together with your general guidance and finish it yourself.

You’re still the creative lead here, it’s still your vision and mostly your execution but if you’re outsourcing the most labour intensive part and the most repeatable part then it means you can streamline everything else.

It’s not going to be without its issues, people will be late, do a bad job, leave you in the lurch but that’s fixed by practice. It’s entirely possible with just a little bit of help and some intelligent streamlining, you can conceivably double your workload by simply delegating tasks in this way.

Growing into an agency

Growing your freelance business into an agency is what most people see as the natural step and it’s pretty obvious why. More projects, more staff, bigger clients, offices - it’s all fun, why wouldn’t you want to do that?

Before considering this option though, remember there’s a decent sized shift that needs to take place here. Your job will not be doing the work, it’ll be selling, strategy and being a project manager. Look hard here at your skill sets, if you were interviewing someone with your skills and personality for a project manager role, would you hire them?

As a pretty introverted guy I was hardly cut out for meetings with strangers, phone calls and negotiations, but you make things work for you. If you find yourself enjoying the meetings, and the networking side of matters more and more, yet getting bored or bogged down by doing actual creative work then it’s probably a sign you’re set to run an agency.

Transitioning into an agency

Remember I said your team would come in handy at some point? Well this is that point. As you transition, you need to spend less time in front of a computer and more time in front of humans. What you need to do is start outsourcing projects from start to finish. You can be hands-on to begin with but it’s good to see that other people can do as good if not a better job than you. That’s what you want.

The aim, in a weird way, is to become the worst technician in the company. Hire a better designer, a better developer, better editor, cameraman, writer - whatever the skill is, hire people better than you.

In an ideal world, you’d already have your basic expenses covered with retainers at this point but if not, start now. You can’t sensibly hire someone full time until you know you can pay their salary every month with money to spare. While you’re building that up you can pay someone on a contract basis to take a project on start-to-finish then with any luck, transition them into being full time when you can.

Deal flow

Your full time job at some point needs to be to keep the deal flow coming in, push projects forward, increase the spend of current clients, be an account manager and keep the income of the business looking healthy.

Retainers as we’ve said are the way you’ll be able to sleep at night so whatever you can do to get your clients paying monthly for updates, consulting, whatever you can, you should do it.

Growing an agency is fun. You’ll do some amazing work, earn great money and work with some great people. Build a vehicle to facilitate these things.

Enjoy your work, but it isn't everything. Make time for you and your version of fun.

One of the most popular articles I’ve written is called “Work-life balance is bollocks”. In re-reading it, it’s as true today as it was when I wrote it so I’m going to include it here in full.

Work-Life Balance is Bollocks

Let’s assume a 40-hour work week

In order to have a proper work life balance, you’d need to have the ‘life’ part being 40-hours too. Seems simple enough.

What people refer to when they talk about the ‘life’ part though is things like going out, partying, socialising, adventure, holidays, exercise, cooking, DIY, sport, watching TV.

Here’s the problem. You can’t do 40-hours of that stuff in a week if you have a 40-hour work week.

There’s not enough time.

What happens is you end up cutting your work short and working less to accommodate for the life part, but still not having enough time to do everything you want to do.

Net result: Not happy with work results (because you’re not working enough) and not happy with the amount you’re able to enjoy yourself.

Solution 1: Mix it all up

I like to do a mix of both solutions but I lead with this. Say you want to work, earn money and spend it going away somewhere nice. Well here’s a novel idea – how about going somewhere nice, expensing the flights and working anyway.

To some of you, that might seem dumb but let’s be real. You are a business owner, are you really going to sit around and not do ANY WORK for the entire time? Nonsense. Don’t kid yourself.

Just embrace it and mix the two together. I’m not suggesting work the entire time you’re away but do it in a smarter way. Sunbathe during the day if that’s your thing and work when the sun’s gone down.

A funny thing happens when you’re working on holidays. You don’t fuck about. You get in, you get it done and you get off the computer again.

Give it some thought. If that idea doesn’t work for you, then you’ll be more a fan of this.

Solution 2: Plan the ‘Life’ part and work around it.

We all do this to some extent but I think we could do more of it. Here are a list of the ridiculous things I plan my work around:

  • Cooking
  • Barcelona matches on TV
  • Social gatherings
  • My Dad’s shift pattern
  • DIY projects

Sounds ridiculous doesn’t it? I can’t work now because I need to chop carrots. Yes, it’s dumb, but if you want an epic meal that needed prepping at 3pm to eat for 8pm then you need to schedule that in.

You will not catch me near a laptop when Barca are playing. No chance.

My Dad works mad shift patterns mixing days and nights. I’m getting older. I’m well aware that one day, the guy isn’t going to be around to have coffee with and learn from. I want to take advantage of that now.

If he’s got a Tuesday and Wednesday daytime free, I’m going to go and hang out with him for a couple of hours. Work can wait.

You can’t be using chop saws at 10pm and expect to still get a Christmas card from your neighbour. Do that stuff during the day and work later.

In conclusion

Your life is more important than your work. Of course you enjoy your work. I do too. I have the best job in the world but if you neglect the real fun - things like the countries you want to visit, people you want to meet, shows you want to see and things you want to do - then you’ll never be happy with your life. You’ll always feel stressed.

You never want your work effort to feel like a bad deal.

Having non-work time

It is so easy to slip into the idea that you should be working all the time. It doesn’t need to be whole weekends, it can be much smaller chunks of time than that but you should have sacred hours. Perhaps it’s Friday nights. Saturdays are fair game maybe but 5pm sharp Friday afternoon the laptop gets closed and you enjoy time with your family, friends, or whatever it is you want to do. Then if there are any disasters, you can pick them up Saturday morning.

I’m a single guy with no kids so I get it, where’s the incentive to close the laptop when you have nothing to close it for? If you have a family with little ones, this might become slightly easier as you have something vying for your attention anyway.

Protect this time. It’s yours. It’s time away from the laptop where ideas will come to you. Have you ever noticed your best ideas never come to you sitting at a desk? You’re always in the shower, walking the dog, cooking pancakes or something.

Keep these moments, they are vital to your creativity.

Keep the diary full

What would you do if money was no object? Truthfully, it kind of isn’t and you can do more or less whatever you want, you perhaps just can’t do it all the time. For me, I’ve made it something of a rule to make sure the following things are constantly in my diary.

  • Dinners out in nice restaurants
  • Dance music festivals
  • Comedy shows
  • Trips
  • Weekends away
  • Tinder dates (don’t judge)
  • Watching Barcelona play
  • Seeing friends

If you don’t have anything in your diary then there’s little to look forward to and it doesn’t give you that feeling of “light at the end of the tunnel” when work isn’t going great.

Make a list of these kinds of things for yourself and keep your diary topped up. Maybe it’s a good excuse to discover new things you enjoy doing. My summer has a lot more festivals and Tinder in it than the winter but it’s all swings and roundabouts.

This will mean different things to different people.

Do what’s right for you.

This is your life now, it's time to enjoy it.

This freelancer lifestyle isn’t a race. You’re not in competition with anyone, you just operate at the pace you want to operate at. You’re going to experience the highest highs and the lowest lows. Neither are permanent - remember that.

Progress however you want to, be it by making yourself more efficient and doing less work for the same money or growing the income by improving production and increasing pricing. There are many options and one of the most creative parts of the job is tweaking different factors to see what makes the biggest and most positive changes to your business and you can explore them all. Best of all, if they’re not right then you can always just go back to what you were doing before. You’re in control.

I hope this guide has been everything you hoped it would be and we’d be delighted if you’d give it a share on socials or on your email list.

Thank you for your most valuable commodity - your time. It’s appreciated more than you know.

Adam Hempenstall

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