If my life had taken a few different turns, I might still be painting portraits of the gifted and famous (not always mutually exclusive) instead of playing with gadgets, waving my arms around in front of an audience and helping to design the future. I’m pretty sure I wouldn’t be writing this.

It doesn’t hurt to imagine an alternate reality from time to time so I thought I’d consider what I’d be doing if those two worlds had collided. If I’d turned right instead of left and continued on my path to artistic infamy, yet maintained a healthy interest in all things digital. More about my past creative endeavours in Face Time.

Where does one start? I didn’t want this to be a long drawn-out process so I’m not writing full technical reviews of each device. This is about the artistic and emotional rollercoaster, not screen resolution – you can follow the links for more info!

My plan was to test a variety of hardware, from the smallest and simplest to the largest and most complex. Each had one thing in common – a stylus of some kind, but they all use different methods to communicate with the surface or screen.

All but one device is manufactured by the industry-leader, Wacom. First-up is the Inkling £84.95.

A small black box clips to the top edge of a sheet of paper or pad then monitors the movements of a hybrid stylus/ink pen as you draw on the surface.

In theory, this sounds like a superb way to retain a natural drawing style whilst digitising the results. In practice, it’s actually quite remarkable. Once your sketch is complete, you plug the black box into your computer via a USB cable and download the results to the supplied software. This displays your artwork in staggering detail with the option to export as bitmap or vector files. You can even save an animated movie of your illustration in progress!

I love the freedom and the lack of compromise when drawing. I’d like to see a wireless transfer or real-time screen rendering option at some stage but for the relatively cheap entry point, this is a superb product for preliminary sketches.

Jot Script Evernote Edition £49.95 / $74.95 (plus an iPad!)

Making use of the iPad’s Retina screen and a fine-tipped bluetooth-connected pen seems the perfect combination. It so nearly is, but there’s a fraction of lag evident when using apps such as 53’s Paper (not Facebook’s!), Procreate or Evernote’s own Penultimate. The lag can be overcome by using your finger instead of the stylus, but I’ve never been big on finger painting and the pen’s lag just highlights the shortcomings of this compared to ‘real’ art materials.

Wacom Bamboo (now Intuos Pen & Touch £169.99 / $199)

I wanted to refresh my memory of working with a basic tablet and Wacom’s Bamboo was a cool looking device, with bright colours, interesting textures and a material label at one end to hold the stylus when not in use. My view remains unchanged – I’m still not a fan of the disconnected pen and screen. It has always felt unnatural to me when the result of your input is displayed so far away from the tip of the stylus, despite the fact that I’m perfectly comfortable with a mouse in similar circumstances.

Unnatural or not, here's one I made earlier...

I started this process a while ago and the Bamboo has since been replaced by the Intuos range, a more sober look but it sits comfortably with Apple’s current visual approach to hardware design.

Wacom Cintiq 24HD £2,499.99 / $2,999

Wow. This was my reaction before I even manhandled the Cintiq onto my desk. This really is the big daddy of the digital art world, an enormous 24” multitouch drawing board where the image you create is rendered directly under the stylus, just like a real drawing board or easel.

The large drawing area immediately encouraged me to (quite literally) think big, to take large unrestricted strokes and adopt a freedom of creative expression that required less image zooming than other devices. It all feels right and I’m glad I saved this beast until last as it finally convinced me to plunge back into the art world.

I took my alter-ego as inspiration and created a quick illustration of Apptain America, using a wide range of brushes and materials. Having stepped away from my portraiture for nearly two decades I admit to being tempted to pick up where I left off thanks to the Cintiq (and the Inkling). Wacom offers a smaller mobile version but I’m not interested as they’ve been hobbled by Windows and Android operating systems – they’re not allowed to use Apple’s. I’m a creative so It’s Cupertino kit all the way.

So, do I miss the artistic life I rejected 20 years ago? I miss being able to offer a simple answer to the question “what do you do?” I’m still part of the team that creates amazing things but I’m less ‘hands-on’ than I ever have been. It makes me sad that my wife and children aren’t impressed by what I do and it doesn’t make them proud.

I’d like to change that, so maybe I’ll find more time to sketch and paint in a digital world. I have a hunger to bring faces to life again so I’ll start making my hit list to add to my previous scalps, whoever they may be...

Whenever I lecture on design career paths and take a journey along my own creative timeline, I find that behind the twists and turns there are no regrets. Each new choice has resulted in a fresh set of challenges, life-lessons and opportunities.

Before focusing on graphic design, I had a calling to be an artist. Yes, one of those easel-munching, brush-wielding, weirdy-beardies but before I had a chance to sign up for a fine art degree, it turned out that my original calling wasn’t shouting loud enough and my practicality gene kicked in.

I realised that my enrolment into higher education should result in more than a piece of paper qualifying me to sit in a loft painting priceless masterpieces in exchange for soup and soap. Graphic design would become my friend and provide a sensible wage to supplement cars, gadgets, a wife and children.

This was the early 90s and the cult of celebrity hadn’t quite become the all-consuming monster it is today. Simon Cowell wasn’t yet selling a dream of fame for fame’s sake so I decided to launch a parallel career whilst at college studying the art of typography, branding and page-layouts. Never one to give up on a dream, I would paint celebrity portraits under the professional guise of ‘Artistic License’.

The fact that I had branded myself as a serious contender opened more doors than a smock and beret ever would. Having worked on a newspaper before starting college also helped, with a group of entertainment journalists (and their contacts) at my disposal.

The first portrait I ever tackled was born from a series of photographs taken of ‘Little Eagle’ – a genuine Sioux chief living and working in... Cornwall.

This one painting focussed my creative style and began a partnership with guache, pencil and card that would last for the next three years, resulting in commissions for a diverse collection of extraordinary characters, including Chris Eubank, George Melly, Patrick Moore, Michael Douglas, Tiff Needel, Bernard Cribbins, Robert Hardy and numerous leaders within the business and sports communities.

So why didn’t I carry on? Well, the cult of celebrity eventually caught up and PA’s were no longer willing to give the same level of access I had previously enjoyed. At the same time, I had graduated and needed some focus – graphic design won.

This is the point where I usually explain to eager students looking for some direction that each stage in my career has enriched the next. Running Artistic License as a company provided invaluable financial, operational and social experience when it came to starting my creative agency Fijit.

The ability to translate creative thinking into creative communication is a useful skill that has followed me from job to job and I still believe passionately that a designer should always be able to focus their preliminary thoughts into effective imagery. Dexterity with a pen or pencil should always precede the digitized phase on a Mac.

I now struggle to find time to get as ‘hands on’ as I used to. The last portrait I tackled was Tim Burton’s, as featured in my blog entry Gone For a Burton. I am however looking forward to more illustration work in some of our forthcoming Brandwidth iPad apps with innovative storytelling and games.

I will always look back fondly on the celebrity portrait world and I intend to write more on the challenges, rewards and antics at a later date. Accusations of wrong eye colouring by Bernard Cribbins, xylophone lessons with Patrick Moore or blocking Michael Douglas into Leicester Square with a taxi thanks to our late film premiere arrival – all part of a designer’s rich career tapestry!