How to play the money game

I’ve recently got back to writing my 2nd book (about how to find ideas you love, make ’em happen, and make money out of them). And as a result I’ve been thinking about the monetisation part – turning the things you love into an income.

I’ve realised that the very first step to playing the money game successfully is to realise that it IS a game. And a really fun one at that.

You see, the majority of people make a living as an employee and therefore have little control over their income beyond asking for a pay-rise or changing jobs. But self-employed people know that their income is completely up to them. If we can find a better way of providing more value to more people and a good way to charge for it, we can increase our income.

If we want more money for something in particular like a holiday or a new car, we can give a push to some aspect of our business and go get it.

And when you realise that there are many different ways to package and deliver what you do, you can start getting creative about it. You can play with it.

Choosing the right form and right price could make you 10, 100 or even 1000 times what another one will.

So you might discover that selling your kindle book for 59p makes you more money than selling it for £8 (as author John Locke discovered when he sold one million kindle books in 5 months). Or that giving it away for free for a fixed time could benefit you financially in the long run.

An example from my own business is the creation of the 30 Day Challenge. Instead of only helping people one to one, creating the 30 Day Challenge with Selina has allowed me to help 200 people at once, to have fantastic fun doing it, and bring nearly £30,000 into the business in one month. And having 200 people on the 30 Day Challenge makes it all the more powerful experience for the people taking part.

This is the real delight of playing the money game creatively – everybody wins.

So, having spent the last couple of years sharing how to find the work you love, now I want to explore this money game with you and share some of the fun stuff I’ve learned in my ten years of self employment – so that you too can play the money game and win.

How is your game?

I’d love to know where you are with the money game. Whether you’re already making a living without a job or still planning your escape, where do you get stuck most in the money game?

And if you’ve managed to play the money game well, what was the breakthrough for you in getting there?

Leave a comment to share it with us…


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  • Adam

    Hi John,

    I’ve recently escaped the corporate rat race to properly follow my passion. Whilst things are moving along slowly I do hope to earn a proper income from it soon. I’m excited by the topic of your new book and look forward to reading it.
    In the meantime, if I do hit the jackpot I’ll let you know!

  • johnsw

    Go for it Adam! What’s your new line of work?

  • Bebe

    I’m more or less on the square 2 in my illustration/drawing carrier. Earn some money from time to time if the opportunity happens, but nothing regular. Mostly, because I hit the wall pretty quickly with the lack of knowledge on how to produce/print larger amounts of pictures/t-shirts and send them to people who would like to buy it. The amount of business-management overwhelms me.

  • johnsw

    I would have thought having someone else print them would be more efficient Bebe?

  • Bebe

    I try to find a place that would print them for me, but all are so expensive that at the end I can’t sell anything. But there are so many people doing this (eg. Etsy) that it must be possible. I find that in making business sometimes the access to the knowledge about right people and ways to do things is the first and possible biggest obstacle. And one have to fight for it…..I wish more sharing.

  • Cheryl Joy Adamson

    Such a timely post for me – thank you! Having left one major profession (law) 3 years ago and then trying to find my passion. I have finally pinned the slippery fella down and am planning inspiring events as part of it. Due to hand notice in on cage job in approx 1 week. I had my first event on Tuesday but I didn’t set the pricing right at all. It was always going to be a test so it didn’t matter toooo much that I didn’t break even, but it’s not sustaible. I know that paying for great parties for strangers is not a tenable business model!! It took me enough guts to charge at all, but to compensate for that i gave loads and loads and loads which meant that people had a fab time but it wasn’t practical. Would love to get over this hurdle so I can start making ‘real money’ rather than ‘playing business’ which is actually working a job I hate to create money to pay for giving stuff away : /

  • Youcanthidethespark

    I like the idea of playing the money game but have never quite got to this point myself. I have been self-employed for 12 years and have been paid a good daily rate, but always needed more days’ work in the month so never ultimately earned that much! I have FINALLY figured out what I want to do (thanks to the 30 Day Challenge I was on recently) but sadly neither of my passions (writing children’s books, and putting my character designs on cards and t-shirts) are going to earn me much money anytime soon. (And not on a regular basis.) So I am now looking for full time work which will give me stability whilst I work on my passions in my spare time…On a positive note, I’m really happy and excited to have finally found my thing. I just wish I didn’t have to go back to full time office work (sounds like I need to read your book)…

  • Joanne

    Earning is erratic. Have moved house a lot and this may continue so I want to be location independent – or have an element of this. The stuck bit is getting to a point where I am happy to share my web and promote myself, I feel I need to be much clearer with what I offer and who my ideal client is. Have half completed many different (written) projects and been disappointed with how they were evolving. Still excited about the topics though and want to finish these projects. The good news is that the clients I have keep hiring me back and let me do exactly what I want.

  • theamp

    Have you seen these guys for t-shirts?

  • johnsw

    Sounds like you’ve got the value thing sorted Joanne and that’s the most important. The rest is just about getting better at marketing

  • theamp

    Sorry here is the link

  • johnsw

    Well if you’re going to get full-time work, make it the best full-time work you possibly can while you work on the other stuff

  • johnsw

    Ah yes, charging what you’re worth is an important part of the game. Keep working on it!

  • Youcanthidethespark

    Will do.

  • Joanne

    I wish I had your confidence that I have the value thing sorted! Thanks for saying that though.

  • johnsw

    If clients keep hiring you back, you do!

  • stacey

    My problem is I get stuck. I have a lot of knowledgeand information, but I can’t move forward. I procrastinate and feel guilty about item. Instead of doing the work I make up excuses to not do it and or I start all over again with the next educational thing. It’s really self-sabotage. Torture!

  • johnsw

    You probably shouldn’t be trying to it on your own then, Stacey.
    Are you willing to start small, and willing for your first thing not to work? If so, do a Play Project.

  • Julia

    I always seem to get stuck on knowing what to charge, whether it’s how to price a 2-hour workshop or how to value and price another person’s artwork for an exhibition. I find myself getting very stressed when trying to make these decisions, wanting to offer good value to customers, but also make a decent income for the effort I put in.

  • Bebe

    Thanks theamp! I have too look for something like that in Europe 🙂

  • Christine Hurst

    Still planning my escape, but I have a weekly plan and by this time next year, I WILL BE FREE OF THE RAT RACE. (Hows that for certainty!).

  • Trevor

    Hi John,
    At stage 2 and stage 1.
    Stage 2: Jumped ship at a consultant electrical engineering firm 3 years ago to work for myself. It’s almost impossible to get data on pricing and whilst I always feel I’m overpricing my time, I always get paid and never have anyone haggle. Would like to charge more but don’t want to risk what I have. How do you push the envelope without losing customers?
    Stage 1: I’ve always loved sci-fi,nfantasy, design and CAD which makes my passion creating 3D CGI models but I’m struggling to find direction. I’ve taught myself a lot technically but finding a market or niche escapes me.
    The ultimate aim is to reduce my hours but maintain income through self-selling products rather than selling my time & experience on a project by project basis. I’m now on 1/4 of my former salary but I’m way way happier being my own boss.
    I love to teach (used to teach engineering at college part time) but struggle to see how that can fit with my chosen areas of work/play.
    Love your book and am looking forward to the next one.

  • johnsw

    Great questions, Trevor. First off, I realised in my consultancy days if you’re getting work OK and no one is haggling, you’re not charging enough – because it means everyone can comfortably afford you. If you move up within the band of pricing for your industry, you’ll start to get a small number of rejections – but you’ll be making more overall. I can’t guarantee it for you but you can always try it out with one or two new clients and see what happens.

    For the other stuff, I think you should be doing more play projects – create a CGI project you’re really excited about and put it out there on youtube etc. Do it for fun first time and see where it leads you. The important thing though is to ship and share so others can see it. Then you start to get others involved and you might get noticed. Or if nothing else you’ll have the satisfaction of finished stuff.

    Same thing for teaching. If you love teaching, how can you go teach something? At first these things might not make much but it’s better to going out doing real projects than thinking about it.

  • Adam

    Cheers John, I was still only half way through your last book when I left the rat race (it’s that good!).

    I’ve more than dabbled in Photography for years, even had a wedding and portrait business for a while. Anyway, its not specifically that which I’m doing now but I have realised that photography is my passion (only took me 21 years to grasp this!). Just getting closer and closer to defining the parts of it I love by getting out there and doing it more.

    I’d love to run workshops to help other budding and professional photographers. It would also be great to create a practical community for them too. I’m finding that in order to do this I need to get more work under my belt first so I have a broader portfolio of work and experience.
    So far this year I have completed some commercial product work and am also starting to work on modelling portfolios.
    As a personal project I am creating photography essays about my local area. This is a personal project as it brings in my passion for travel photography and I’m hoping that by posting them on social media it might create some interest and lead to other things.

    So whilst I can’t help you with successful earning stories yet, that is my main aim and I’m working out various routes to get there.

    Beyond all money though I have to say I’m in a much happier place these days and don’t even feel the need to earn lots of money, just an income of sorts would be nice 🙂

  • Adam

    I had a whole plan for my departure from the rat race too which I called “my escape tunnel”. When it was a bad day at work I just used to say “better keep digging the tunnel” and revise the plan to make it happen quicker and better.
    I just wanted to let you know that it worked out perfectly and to keep going, yours will too. Just make sure you stay on track.

  • PJ

    Having trouble getting myself to do publicity work/PR etc. The creation isn’t the hard part for me. I get terrified about approaching influential people in case I get it wrong, but then instead I endlessly procrastinate or start a new project.

  • johnsw

    Can you choose someone you think you’d really enjoy working with and approach them first? You’ll have to be willing to get it ‘wrong’ in order to learn

  • johnsw

    That sounds good Christine. If you’re making progress each month while still in your job, rather than starting when you quit, you’ll be way ahead

  • johnsw

    The nature of the free market, Julia, is that the value of something like art is whatever the buyer is willing to pay.
    The pricing of workshops is very dependent on what the perceived value for people (what they’re going to get out of it) but also on how you present your status and value as leader of it

  • johnsw

    Sounds good Adam. Do mix the pure passion projects with some commercial ones so you can continue to explore the market and where the money is too.

  • Adam

    Thanks John, that’s a valid point. I guess it can’t be all play all the time but if its a good balance then it works. Will be consider this during my planning and structuring week (this week), thank you.

  • johnsw

    Well hopefully you can find some commercial ones that you really enjoy too!

  • Adam

    Sounds ideal!
    I think I need to start my marketing to let people know that I not only like, but can do this for them. Need to show I am the solution to their problem somehow.

  • L.P.

    Like nearly every actor I know, I struggle to find the flexible “day job”, which allows subsistence level while also allowing the time to go to auditions, (often at short notice), promote myself, and not drive me crazy. Actors standard fare is call centre work, door-to-door market research, promotions work etc. Generally the stuff no-one else wants! The older you get, the harder this level of work is to accept, and the more depressing it becomes. I am re-entering the game after a fairly successful career in my youth; also attempting to set up a voice over business, and spend some time marketing myself as an actor and voice over. I find that the time to do this is very hard to come by; yet without the time spent marketing – where am I in the ‘money game”, and how quickly is my “career” moving forward? Guess! (L.P.)

  • johnsw

    That’s not easy to juggle but finding a better income stream to support you would be worth the effort I’m sure.

  • Rob F.

    I’m in the nine-to-five but wanting to start freelancing boat, and I’m not playing the money game yet. I think I’ve taking defining and marketing my services and setting price points a bit too seriously, so much so that I’ve scared myself away from it. I’m asking some help in solopreneur fora and the like.

  • Rob F.

    I know just how you feel, PJ! 🙂

  • johnsw

    Is there any way you can get some freelance work while still in your 9 to 5? Then you can experiment with pricing before you quit. Preplanning marketing etc is usually a distraction.

  • Rob F.

    I’ve already had a couple of freelance gigs, but they’e not been ongoing ones, unfortunately. I’d like to keep my momentum up, but I’m not sure how!

  • billtaichi

    Trevor if you can create 3D models you should look at selling models for people making games. Unity software (game creation software) has a online store and good animated models usually sell well. Maybe you should look at making models for gaming software, it is something that once you get it setup at a few places it could become passive income. There is definitely a damand for it and work done once can pay off for a long time.

  • The Amazing and Incredible Mr0

    Right now I’m unemployed, living with the parents, and trying my best to avoid working thankless work for some asshole boss.

  • Kara Adams

    Great read thanks for sharing! Crowdfunding is another effective way to easily raise funds and more people are benefiting from it everyday. Check out crowdfunding platforms like to learn more about its benefits.