Creatively Handling the Admin Side of Freelancing


There are very few who would argue against the notion that most freelance professionals, especially those operating in the design/development and writing arenas, tend to operate from a creative base. They are, by and large, a group that has chosen to let the right side of their brain steer them as far as the road stretches out before them. Having embraced their creative and artistic nature, merging it into their career path and never looking back. And for the most part, a creative mind fits well in this freelance environment because they ultimately call all the shots and are bound by very few restraints — for the most part.


This road, however, is not without its bumps, and for a lot of freelancers, these bumps come when the left brain must be engaged to navigate the terrain. Most of us are familiar with the concept of right brain vs. left brain, wherein it has been shown that the two hemispheres of the brain control different modes of thinking. The right is the creative and artistic side, the left being the more logical and analytical.

Given that most of us are less apt to be full-minded (meaning we excel in both modes of thinking), there tend to be some issues when it comes time for you to mentally cross over for a short time to the other side. This can be a problem in freelancing, because though we might prefer to turn right, we have to handle every aspect of our business and that means every so often going left.

The administrative side of the job tends to be left-brain-heavy, and can prove difficult for some right-brainers to tackle. Below, I have broken down the offending areas that often hang us up, and have provided some tips for how to make it through these left-brained business barriers.

Also consider our previous articles:



The first administrative task we will look at is scheduling. Not only because of its importance to our freelance business, but because effective time management can aid with the other elements of your admin responsibilities. This tends to be very difficult for extremely creative individuals for the simple fact that right-brainers tend to be more random and less sequential in thought. And since scheduling creativity is not something we can always effectively manage, we tend to overlook the idea of scheduling our work altogether.

Ironically, this often-avoided admin element by creatives can actually help stimulate our creative workflow. Scheduling different left-brained administrative tasks to be handled throughout the day offers your creative mind a change of gears. It essentially unplugs you from the mindset you’re in when you create and gives your often overworked right brain a bit of a break. So when you return to the right side of things, you do so refreshed and recharged. Scheduling your day, therefore, can benefit both sides of your freelance business.

For more on this…

Tips for Tackling

  • The more fun that it is for you to use, the more likely it is that you’re going to use it. Find an easy-to-use time management app with a fun UI and you will find that it is easier to motivate yourself to open it up and dive in.
  • Be strict with yourself about all the self-imposed schedules you have come up with. By enforcing the schedules and through repetition, they will eventually become second nature and will be easier to work into your routine.
  • Do not be too hard on yourself, just let your system evolve with you. Chances are, you are going to have a period of adjustment for this, so let it evolve and grow to suit you better rather than get frustrated and give up. The better the fit, the better it will serve your business.
  • Always set yourself up with a redundancy system! Given that you may not be used to scheduling yourself, it may behoove you to have to have a backup plan. Having the extra coverage may also provide some peace of mind.



The next administrative task we’ll talk about is the bookkeeping side of business. I have always had an aversion to numbers, math and anything accounting related, so this was a big adjustment for me as I imagine it has been for a lot of other freelancers. The easy answer for these woes is to simply hire an accountant, but for some — especially those just starting out in the business — this is not necessarily an affordable plan of attack. So we have to take these tasks upon ourselves and be able to make sense of it all.

The great thing about this area of your freelance life is that so many application authors understand our pain and they have developed wonderful programs that take most of the guesswork out of the equation for you. Client, account, and project management are becoming easier-than-ever for the right-brained inhabitants with applications like Billings8. In these cases the software essentially handles most of this for you, while you simply input a bit of data.

For more on this…

Tips for Tackling

  • Find a program that is suited to your needs only. The bells and whistles that go above and beyond are not necessary, and may only cause confusion. Especially in the beginning, keep it simple so you do not get overwhelmed.
  • Make sure that you stay on top of these tasks. The bookkeeping is what keeps you going and stable, so make sure you do not get behind in your billing…that’s the client’s job. Set billing reminders and collection reminders so that you do not let anything fall through the cracks.
  • The less time it takes to get done, the less apt we are to put it off. Creating templates for your accounting paperwork can help cut down the time and thought that has to go into it. And that will naturally make us more prone to tackling.
  • Help avoid penalties for your accounting practices. Each country and province has different laws and regulations that are governing your business and the taxes that accompany it. Be sure that you find out what they are and keep up with changes to avoid accumulating penalties and fines.



Another aspect of the administrative side to your freelance business that will often draw periods of procrastination is your business correspondence. This is not referring to replying to a pen pal or any kind of creative writing; this generally is detailed and contractual which immediately presents itself as a barrier to the right-brained thinkers. So it is a natural reaction for the creatively minded to avoid dealing with the inbox or returning messages that we cannot deny are important. Even though this is not occurring face-to-face, we still feel out of our element, so we put off until tomorrow what should have been done today.

Once again, the right-brainers tend to think more randomly than sequentially, so communicating our thoughts to those populating the opposite sphere can prove problematic. But this is where the scheduling can further assist you. Most of our business runs on some form of back-and-forth communication — be it with clients, users, colleagues, etc. — so making time every day to sort through your inbox will keep it running smoothly. Getting back in a timely fashion will reflect positively on you and build trust in your brand.

For more on this…

Tips for Tackling

  • Again, get time on your side and this will help get you going. If you find that you are regularly responding to the same types of queries, create copy templates to move your mail along.
  • Prioritize and categorize and the task will fly past. Keeping a hierarchy of your correspondences and having them separated by types will keep you rolling through quick and easy. Again, this breaking down and separating of your messages may not be the easiest for the right-brainers to build into a habit, but it is certainly worth a try.
  • Get in and get out! Try to keep your inbox empty and your messages filed away for easy reference and prioritization. If it is a message that can be replied to quickly, then go ahead and immediately get this done, otherwise file it for later.
  • Brevity is beyond key; it is your best friend. Keep your correspondence brief and to the point and avoid venturing down unnecessary avenues that open yourself up to further questions. If you ramble on, you are simply wasting time that you could be using elsewhere.

Client Relations


Another oftentimes administrative nightmare that freelancers come across is the client relations portion of the position. There is a reason we like the solitude that tends to accompany the freelance career path, and so breaking out of that solitary shell to be able to effectively communicate with clients can be daunting. It’s no secret that in order for your business to thrive, you need to have a client base to build upon. And as should be no secret to anyone, the way you deal with your clients will often determine if they will return.

As a creative individual whose train of thought pulls right, interacting with those on the left side of the tracks will not always go smoothly. In fact, it may not translate well. The means and methods that right-brainers subscribe to, even in explanations and conversations, can tend to be hard to follow for lefters, and vice versa. So it is imperative that we try to make an effort to keep these interactions focused and on topic. And by understanding that such a translation gap exists, we can make more of an effort to bridge the gap when we deal with our clients.

For more on this…

Tips for Tackling

  • Try to step outside your regular right-brained random ways. Momentarily leave them behind and organize your thoughts before meetings. Taking notes and outlining the points you need to cover beforehand can help you stay focused and have an easier time following.
  • Just as we are often responsible for steering clients towards a decision once they employ us, we need to continue to make strides towards being able to steer the conversation. This helps to ensure we stay comfortable as we converse, and it keeps us in our element as much as possible.
  • Since it is necessary for us to understand the project from every angle, have your clients explain their approach from many directions. This may help you find a way to relate to it when you otherwise wouldn’t.
  • It may sound cheesy, but you may want to set up dry-run practices with some of your non-creative friends or family. Running through your side of the conversation with someone who does not work from a creative place may prepare you for meetings with clients.

Backups and Updates


When it comes to important administrative tasks that so many freelancers tend to let slip through the cracks, keeping up with backups and updates ranks high on the list for right-brainers. Creative people tend to work in the moment of inspiration, and we are enveloped by that moment. But the moment moves on, and when it does move on, we are swallowed up by the next task. With our ever-forward-moving momentum pushing against us, we forget to look back, let alone backup (…sorry). And stopping in the middle of our creative flow to update our software doesn’t exactly rank high either.

Naturally, as a freelancer you are going to be the only one managing and keeping records of what is happening on your end, including those ever-precious works-in-progress. Losing them would be devastating, but remembering to back them up, wouldn’t exactly be a right-brainer move …though I think it may be a both-brain sphere issue. It seems that most of us do not consider backing up our files until something actually happens to cause our drive to crash and we lose them all. But again, in the freelance field you are on your own when it comes to data loss, there is no IT department backing you up, so to speak.

For more on this…

Tips for Tackling

  • Automation is a right-brainer’s buddy, and it just means that you may actually get your backups and updates done! Finding a service that backs up your data automatically takes the stress off you and ensures that you won’t have to worry about any right-brained interference in this area.
  • Take a moment, and take a hike! For many of us, as long as we are at our computer, we will not have the willpower to stop working and get our backups and updates done. So walk away. Give yourself a break, start the process and come back later ready to go.
  • A lot of basic software updates are quick and easy and do not interrupt your workflow for very long. Scheduling can definitely work with you in this arena, as most productivity methods encourage you to take short breaks throughout your work day. Set up to run updates during these breaks so that you know they get done.
  • Once again, turn to prioritization and a left-brained-style breakdown to get over the procrastination hump that bars most creatives (and so many more) from getting their updates and backups done. Decide what are your most important files and programs, and make sure that they get done first and foremost. Then as you work through your week, work through your lower-priority items.

Overall Advice

You are creative, so act like it!

Overall, you cannot ignore your administrative responsibilities and hope they go away. So do what it is that you do best — approach it creatively. The interwebs are alive with creative solutions to so many different problems that you are bound to be able to find one that fits yours. If not, maybe come up with your own. Nothing is out of reach for the creative mind, because we know no limitations…even the occasional cross-over to the left side.

Inspiration is the easy part, now lets talk motivation!

One of the hardest things for most creative-minded individuals to do when approaching the territory of the left, is getting motivated to tackle these tasks. Even those of us not prone to procrastination will tend to let the left work pile up longer than the right simply because it is a less comfortable fit for us. The thing to remember is that getting started is usually the hardest part. Not to go all Nike on you, but just do it. Force yourself to get started, and let it roll. Immerse yourself in as much of a creative environ as you can to help smooth the transition, and run with it!

Do not elaborate, that just complicates!

You know if it rhymes it’s got to be true (even though that absolute doesn’t rhyme, but still…). Another important thing to remember is to keep things simple to help with these momentary forays into foreign territories. Remember that this is not where your strengths lie, so it may be best for you not to take on too much in one bite. Keep things as concise and brief as you can, taking them a piece at a time. As right-brained thinkers we tend to see things as a whole rather than in parts, so try to find the different parts and break them down, tackling one at a time. That was the reason for breaking everything apart above, so that you could see a way to start separating the different parts from the whole. This can make the tasks at hand seem less overwhelming.

It’s in your reach, you just have to try for it!

An important thing to remember, overall, is that just because we tend to prefer one mode of thinking (be it right- or left-brained), we can improve our abilities within each side through exercises that stimulate the different hemispheres. The problem tends to arise when there is an imbalance in educational focus that fails to appeal to both sides of the brain. This doesn’t mean it is beyond us, just that we have not worked at improving the opposite sphere. So the more that we keep those sides stimulated, the easier the tasks that fall to that side of the brain will be to take on.

Further Resources

That was a look at the administrative side of the freelancing gig, from a right-brained perspective. Below are a few more resources that will further fill you in on the creative’s take on the linear-thinking side of the coin.

  • Billings21 – Billings 3 is a great user-friendly accounting app for Macs built with right-brained creatives in mind.
  • Dropbox22 – Dropbox is a great automated backup system with a range of packages and benefits for keeping your data safe.
  • Collabtive23 – Collabtive is web-based project management software geared towards freelancers and small businesses.
  • Invoice Journal24 – Invoice Journal is an awesome open source app for invoicing that is web-based so you can access your account from anywhere.
  • Skype25 – Skype is a fantastic communications tool for freelancers to contact their clients and colleagues via their computers.
  • Left-Brained vs. Right-Brained – The Developer/Designer Paradox26 – A great article on My Ink Blog which looks at the different sides of the brain in relation to designers and developers.
  • Understanding Your Brain for Better Design: Left vs. Right27 – Web Designer Depot’s post which examines the brain and the different hemispheres that operate within it.


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Robert Bowen is an emerging author, celebrated podcaster and poet, and most recently the co-founder and imaginative co-contributor of the creative design and blogging duo at the Arbenting Freebies Blog and Dead Wings Designs.

  1. 1

    Cracking article Rob. We’ve just launched a web app for UK freelancers which takes care of much of the business admin and accounting – time tracking, invoicing, paying yourself and *eugh* paying tax. It’s at

  2. 2

    Brilliant!!! Advice such as this really does help! Many creative thinkers really do mush up projects due to their lack of administration. Thanks for a great read!

  3. 3

    yesss…this is can be an inspiration for looking good idea

  4. 4

    Excellent article!! Made me laugh, thanks :0)

    Of course, if you still can’t manage to steer your brain in the right direction, you can always call on a VA to help you ;0p

    KC Virtual Solutions

  5. 5

    Now, that’s something I love.
    Totally my thingy article, loved and enjoyed reading.
    Many thanks ! :)

  6. 6

    I so needed this article today. Thank you for the practical advice and for sharing the resources. Today is my 1 year anniversary in launching my practice and the recommendations on setting up a billing system were great. And also, the writing was fantastic. Keep up the genius!

  7. 7

    Thanks! I always like this kind of articles… :)

  8. 8

    Thanks everyone for the kind words. Glad that you all enjoyed the post, as much as I did writing it. Also that you found it helpful, that is always my hope.

  9. 9

    It’s really a good website for web designer. yeah, very nice, I like it.

  10. 10

    Great Stuff Rob!

  11. 11

    Yes Dropbox is great. In case if you are looking for a securely backup service with more than 2GB for free use this link for setup: and you will get an aditional 250mb free :)

  12. 12

    Backups rulezz. Last year I got my notebook stolen and lost 50% of portfolio :(

  13. 13

    Great post – I’d love to see a followup for simple tools that allow a handful of freelancers to collaborate together or target small businesses. What is everyone using for handling small company calendars, project management, etc – especially when folks are scattered about geographically.

  14. 14

    excellent tips for a beginner like me :) thx

  15. 15

    Great post, keep up the good work!

  16. 16

    Recently it became very popular for almost everybody to write own article about managing and handling the personal freelance business. However, these articles are repeating and nothing new said which is sad. I don’t say you can’t do that, but if you do, try to be different and provide your point of view rather than writing what others wrote a time ago.

    Let it be an advice for your future articles among these empty “wows”, “nice’s” and “excellent’s”. Discussions should be useful, not just a petty talk (I mean comments).

    Good luck!

  17. 17

    great posts Thanks!!

  18. 18

    Useful article as usual ;-)

  19. 19

    Nice post, love you guys!

  20. 20

    Great article!
    I need to find an invoicing tool in portuguese and switted to Brazil.

    Off topic question: what should I do to have my picture on posts like DesignFellow, Osvaldas and others?


  21. 21

    Thank you, I need to stop procrastinating now

  22. 22

    All sound ideas here. Good compilation.

    I’d also recommend, for the head games involved in freelancing, the book War of Art, by Steven Pressfield. Saved my butt several times now.

  23. 23

    Very helpful. Thanks!

  24. 24

    Nice article, but one thing I think is missing is how to tackle non-paying clients. As a freelancer I work with clients from many different countries, so it would have been nice with some advice or links that can help me sort out stuff after invoicing.
    Might be beyond this article, but since you have listed a topic such as Accounting I thought collection of debt (unfortunately) might be the next relevant topic.

  25. 25

    Freshbooks is much better invoice journal. For dutch visitors try

  26. 26

    I am sure this is fabulous but as a 90% right brainer, its too white for me and way, way too much text with not enough pics, Id love to read it but can’t really

    any chance of making it more (right-brained) colour full :-)

    a lot of RB’ers are dyslexic so the text will look hazy and make some pepes sea sick (nauseaous) it does me anyway

    would be great if the BG colour could be changed and the text made larger and bullett pointed too

    would be great if you could

    thank you


  27. 27

    This was a helpful article Robert, thank you for sharing!

  28. 28

    Love the article! We’re a web design and development agency, and we hated the time and effort involved in business admin!

    So we set about making it easy. From contact and project management to invoicing & accounting etc. we wanted something that was integrated, full management from one login. The result is Moobiz we’d love to know what you think!

  29. 29

    I highly recommend GrandTotal for freelance invoicing on OSX – you can read my full review of different invoicing apps for mac, if you want to, here (

  30. 30

    thanks for share you are awesome smashing team ;)

  31. 31

    This article is right on. I have been trying to cut down the unbillable hours that I spend on overhead and have adopted Ofuz ( to take care of contact management, task tracking, and invoicing. It is in beta, but it already is making a huge difference in the profitability of my work day.

  32. 32

    Regarding the bookkeeping/accounting, it’s so true! It’s one of those tasks we all cannot slip on as it’s our bloodline. I used to use a desktop accounting program and do all bookkeeping myself. My biggest advice to everyone is create the invoices yourself but hire a bookkeeper to do everything else. I spent so much time at the end of the year keeping track of my bills, that I should have just paid for a bookkeeper. It’s kind of like, if my hourly charges are $30, and i spend 3 hours a month keep track of my bills, why not just pass it to a bookkeeper who can do it within an hour and i just pay $30-$50 a month?

    I use Billing Boss because it’s simple to use, free, and I can currently create unlimited invoices for unlimited customers. My clients usually pay me online when I email them the invoice. I use the tool with my own merchant account while I know other users use PayPal instead. They also have a mobile version so I can create quotes/invoices anywhere.

    Full Disclosure: This author has been compensated by Sage. I am their Social Media Consultant but I was using their product well before they contracted me. They found me when I sent them an email giving suggestions about Billing Boss!

  33. 33

    We’ve been using FreeAgent it’s a fantastic accounting package I’d highly recommend for graphic designers, web developers and photographers!

  34. 34

    I’ve learn several excellent stuff here. Certainly value bookmarking for revisiting. I surprise how much attempt you place to create this sort of excellent informative web site.


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