What does it take to work for yourself, be a success and not be miserable?

There is a spectrum that exists, running between working for someone else and working for yourself. Theoretically, the ultimate state of the ‘working for yourself’ end of the spectrum is having money work for you and not requiring to do any work at all.

Of course, what you do depends on what you want in life.


Most of us aspire to push ourselves further along towards the right, working for ourselves rather than making someone else’s company rich.

I’ve worked for myself for the best part of five years now, but I can’t say it’s always been easy. Working on your own terms can be hugely liberating, but it can also bring in a host of discomforts, including sporadic income, loneliness, and overwork.

Others either experience the same, or struggle to actually get to a position where they are 100% working for themselves.

Having had a good deal of experience now as a self-employed illustrator, and having interacted with many other freelancers in my time, I’ve put together a list of what we all need to make it work. My view is that if any of the following are missing, your maintained joy and success will be compromised.

I’ve also included some encouraging comments from a range of Red Lemon Club subscribers who currently work for themselves (thanks for contributing!).

A product that meets a desire that people will pay for

This is where those of us who do what we love but fail to earn money from it are placed uncomfortably in the light.

Just because you really enjoy what you create, does not mean that you can make consistent and rewarding income from it.

As we have seen all over, it is possible to make money from all kinds of creative work, from weird sculptures of bones, to formaldehyde dead animals. There is hope for everyone, but it comes with awareness of audience and hard work.


Your product or service must meet a genuine need from people who want something and are willing to pay for it.

In the arts, there are several things that contribute to the demand behind various kinds of creative work.

This includes actually solving a practical problem, such as having a brand identity, to something that is hugely fashionable, to simply being a tasteful addition to someone’s living room interior.

With my own work, I’m constantly thinking about how I can be an actual source of increased sales and user engagement for the businesses I work with. I explain to prospects how my art can make their brands more memorable, encourage trust and ultimately make more sales.

People will pay for something they regard as valuable. Creative work that is not distinct, clearly useful and devoid of honed, experienced craft is unlikely to motivate desire in someone to pay money for it.


Knowing your audience

Self-employed people who eventually lose steam and struggle are very often those who never identified and actually served a defined audience.

Knowing who you are creating for makes everything about working for yourself easier, but also more fulfilling. There is real joy that comes with serving the needs of people that interest you.


Knowing who your target market is, especially if it is a small group, makes getting work more manageable, because if you are taking action to reach out to new prospects, you know exactly who you are approaching and what you can do for them.

This means the process is much more efficient and effective, rather than wasting time trying to please a wider range, and suffering their lack of interest.

Focus on an audience that is as small as it can be without it being so small that the number of opportunities through that group, are diminished.

Too many people I consult try and be everything to everyone, and their sales suck as a result.

Right now, my defined market is designers and marketers in rapidly-growing software companies. This is where I’ve had my most lucrative work opportunities in the past, and it is where I see most continued potential.


Awareness of getting your social needs met

Working for yourself is, by default, isolating. When left unchecked, it is likely that your much-needed regular social interaction gets discarded.

We all need to be aware of how much alone-time we are having and how much social interaction we personally need to feel good as social beings.


A lot of the time, it requires effort to be social. Sometimes we need to be plain anti-social in order to get larger projects done, and that’s ok.

I’m going through this right now in order to build some products for Red Lemon Club. It will take months of me being isolated and I know that that the social side of my life is being neglected. But understand that socialising is a necessary element to our success as freelancers, not something that is separate to it.

Know that by building in social time even if you don’t feel like it, your own fulfilment will improve. This will have a direct impact on the quality of your work and your motivation.

I don’t need to party or be around groups to feel better, but I always feel invigorated after a good talk with a friend.


Regular connecting

‘It’s not who you know, it’s who knows you.’

I recently gave a talk where my goal was for the audience to go away with the phrase: ‘Connect Every Day’ burned into their memories.

Especially if you are not yet super-famous and have PR people and agents doing all the connecting work for you (which is still no excuse for not regularly reaching out to people), you need to be making connections. All the time. Every single day.

Many hundreds of thousands of people make things like you make things. You will disappear into obscurity if you don’t stir the pot and keep your connections hot, into the long term.

The most effective way to generate opportunities for new projects and value in knowing other people, is to regularly communicate with relevant individuals.


Most of us either try to promote to anyone and everyone, or to no one at all.

No creative business should be without regular connection-making. You need to be doing more than you think, and then some more. You need to do more connecting than you even feel comfortable doing, especially if you are starting out.

It’s a GOOD thing to be turning down client opportunities if you have too many. In fact, to bring in consistent income to your business, you need to be in a situation where you are regularly turning down opportunities.

All this will do is improve your reputation for being fully booked, and high value. If you rarely turn people down, it’s time to AMP UP your connection-building.

Use email, send out physical mail outs, call people, go to events, and tweet. Someone you email today could give you a job in three, even ten years if you keep the connection going.


Being profitable

‘Money is better than poverty, if only for financial reasons.’

Woody Allen

No business that does not make a solid profit every month is a healthy one.

An unhealthy business financially means an unhappy business owner.

I’ve experienced too many months of zero to low profit to return to waiting around for opportunities to come to me. Connecting with people every day is now a habit I’m forming so that my businesses stay profitable.

Profit means more money coming in each month than the costs of running that business. Make sure you stay profitable from as early as possible. Profitability should be your number one goal beyond all else. Without funds, you will be unable to keep the business, or your passion, going.

Successful businesses, creative or otherwise, move fast to ensure enough new clients and sales are coming in.

Screw ‘starving artist’. You’re in this to make money, and lots of it. Bringing a great product to enough of the people that need it and are willing to pay well for it, is the way.


Financial awareness

A basic understanding of finance is crucial if you have nominated yourself to make money from your art. Read basic blog posts about the basic finance stuff like profit and expenses, then read a book on the basics.

Being on top of your finances rather than knowing everything about it is key.

But the more you know, the more in control you will be. Being in control financially means you are experiencing what it feels to run a business.

A lot of future financial pain and worry can be avoided through knowing how much needs to be earned, set aside, how to record it, and when and how taxes should be paid.

Now you’re in the driving seat, unlike so many other businesses, let alone creative businesses, that fail fail fail because they don’t get simple finance.


Passion is maintained

Doing things that are in line with your passion will keep you motivated.

When the work you do serves your passion, and you can maintain it, you are on the right track, and you will stay fulfilled.

What is passion?

It is the fuel that drives you. It’s the thing you engage in that brings you to life because it agrees with your skills, your values and your interests all at once.

Work out your passion by asking questions like:

If I had to choose one thing that I had to do every day for the rest of my life, what would that be?

What is the most important change the world needs to see right now?

What gets me really worked up that I must campaign for?

What types of books do I read the most and how might they indicate what I’m passionate about?

Make sure that your work, or your eventual work, allows you to do what fires you up.


In my case, my passion is to better promote the arts, so as to enliven people (makers and their audiences) for the good of the planet.

My illustration work fits in with this passion because I’m creating visual art to enliven people, but the work also allows me to earn money that I invest in Red Lemon Club, which also serves this passion.

You must be constantly hungry to set to work.

You must actually want to create, and promote what you create, on a daily basis because your passion demands it.

A successful creative business requires superior work, and passion will get you to the level you need to be in order to do superior work.

What else do you think is important for running your own business and being ‘happy’ in the process?


  1. Thank you for this article. There are some days, when one needs to read or listen to it again, at one piece. It is one of those days for me.

  2. So many truths here, Alex. I really like how you dispense with the ‘starving artist’ mentality with this post. I feel like many creatives hold themselves back when it really comes down to it. Especially with regards to finances and money matters… when it comes time to invoice that client and call them to the counter (as uncomfortable as it can be), that ability is what really separates the amateurs from the pros. At the end of the day, it’s a business… a fun one that we love, but a business nonetheless.
    Great insights, thanks for sharing!

    • Thank you Mike. Yes, there are many blocks in many creatives for when it comes to making and closing sales, and this is something I will be pushing to change at Red Lemon Club. Thanks for reading! Alex

  3. Thanks Alex. Yes I agree it can be lonely working on your own and I certainly have a few days when I wish I worked in a busy office again. However, working for yourself provides so much more freedom and space that I don’t think I could go back to an office environment full time. Getting out and seeing friends and attending creative social events is the key I think to staying inspired and happy.

    • Hi Mark. Yes, it can take a little effort, but the options to socialise for freelancers and self-employed people are wide.

  4. As usual a great post, very thought provoking.

    The questions at the end are really good because I’m having a hard time at the moment trying to figure out what to do, so these will really help me make some decisions about what to do now//next.

  5. Really nice article, Alex! It really got me fired up, especially the financial planning part. Know what’s coming in and going out. I definitely need to be a lot better about that. Thank you for sharing! 🙂

  6. Alex, I’m constantly reading and listening to advice about how to advance my illustration career. I can honestly say your articles are absolutely the most helpful, concise and truthful written advice I’ve come across {big thank you to my friend Masha who recommended your site!}. As far as being ‘happy’ it’s simple to me. I strive for people to respect my career choice daily. Of course, making a living is a close second! 😉

      • Hi Alex, Sure! I was greeted with lots of negative reactions in the past when sharing that I was an artist as a living. I’ve found that the more you can explain exactly what you do… the more people will be open to you and your career choice. For instance, when I say ‘picture book illustrator’ instead of just ‘artist’ I’m greeted with intrigue instead of the classic eye roll 😉 It’s also easier to network the more specific your job title is…

  7. Thank you. I’ve been pondering where to steer my somewhat-still-afloat freelance ship lately, not without bouts of anxiety, and I needed this brutal yet honest wake up call.

  8. Excellent article! Thank you for sharing your thoughts about building a freelance art related career. You’re very helpful. 🙂

  9. Great piece Alex. There was a few sections in particular that resonated with my recent experience as a freelancer. The times when no business is coming in and there are hundreds of FT jobs you could walk right into, are the hardest. Requires a lot of resilience and patience to keep on the freelance path you started.

  10. Hey Alex! I’m a Product Designer from Mexico, and I’ve been trying to start making illustrations. I think it’s one of my passions because it’s what I would do for the rest of my life! But I don´t know how to start making money from them. I know I have to find my target market and start making connections, but in Mexico creative careers are hard to sustain. Do you have any advise? Btw you can check my work in my instagram account if you like and tell me what you think, i know I still have a lot of work to improve! Thanks 🙂 @inkthoughts

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