Creating a Job that Doesn’t Exist with Aileen Bennett

Creating a Job that Doesn't Exist with Aileen Bennett

This week’s guest on the 21st Century Creative Podcast is Aileen Bennett, Roving Creative Director and Idea Thinker Upper.

Aileen BennettIn today’s interview, we tackle a question that many creative people struggle with – what do you do when you look at the jobs on offer, and none of them seem the right fit? Not even the self-employed ones, like consultant or freelance designer?

Should you try to fit in, like a square peg in a round hole? Or should you do what Aileen did, and create a job that doesn’t exist?

I’m delighted to introduce you to Aileen and her work in this episode, she’s a delightfully creative thinker and maker, and a great example of how being yourself can help your business thrive as well as sparking your imagination.

You can get more inspiration from Aileen on her Creating Clever blog and Aileen’s Notebook on Instagram.

Illustrated pages from Aileen's notebook

Aileen's illustrations of Sterling Originals confectionery

Take Aileen’s Creative Challenge (and win a limited edition print)

Every week, at the end of the show, I ask my guest to set you a Creative Challenge – something practical you can do that will help you put the ideas from the show into action.

Here’s how you can take part – and maybe win the prize of a print of Aileen’s drawing of Brooklyn, NYC, and its inspiring text.

Aileen's drawing of the rooftops of Brooklyn

1. Listen to the interview part of the show, either in the player above or on iTunes or your favourite podcast platform.

2. Here’s the challenge, in Aileen’s words:

Think of a job that doesn’t exist. Combine two or three or more of your skills and create a job title, and a brief job description, of the job that would be perfect for you – without worrying whether anyone already does it, or whether anyone would ever pay you to do it.

3. Leave a comment below this post with the description of your ideal job.

You have until midnight United States Pacific time on Friday 4th August 2017 to complete the challenge and leave your comment.

4. Once the challenge has finished, I will pick 3 winners at random from the comments, who will receive the prize of a copy of Aileen’s print.

5. Over the weekend I will send a bonus recording with my feedback on your comments and what we can all learn from the challenge. I’ll be looking through the comments for common patterns, whether that’s ways a lot of you get stuck, or great solutions you’re finding to the challenge. I’ll also be sharing reflections from my own perspective.

6. As usual the feedback recording will NOT be released on iTunes or anywhere else the show is syndicated. It will only be available via the 21st Century Creative mailing list – click here to join the list (and get a free Creative Career course).

Drawing of small bird and text saying sometimes we could all use a little bird that sits on our finger and silently tweets encouragement. Be you, be you, it would say

One last thing…

If you’re enjoying the show it would be a huge help to me if you would take a moment to subscribe to The 21st Century Creative in iTunes.

And if you’d like to leave a brief review in iTunes, that would be even more helpful.

The more people who subscribe and review the show, the more visible the show will be in the iTunes store, and the more creators I can help with it.

This is particularly important in the first few weeks of a podcast – so if you enjoy the show, and you’d like to support it, taking a few moments to subscribe and/or review will give the podcast the best chance of success.

Thank you!

Mark McGuinness is a poet, a coach for creative professionals, and the host of The 21st Century Creative Podcast.

The 21st Century Creative Podcast

The 21st Century Creative Podcast

Hosted by poet and creative coach Mark McGuinness, The 21st Century Creative podcast helps you succeed as a creative professional amid the demands, distractions, and opportunities of the 21st century.

Each episode features insights from Mark and interviews with outstanding creators – including artists, writers, performers, commercial creatives, directors, producers, entrepreneurs and other creative thought leaders.

Guests include Steven Pressfield, Scott Belsky, Jocenlyn K. Glei, Joanna Penn and Michael Bungay Stanier.

Responses to this Post


  1. I’d like to be a travelling good/crazy idea, random life-improvement and quote collector, inventor and sharer.

    I’d travel the world and find / come up with good ideas, quotes and experiences and sketch them so I can share them with the world visually. I sort of already do this on my instagram (@eurydice13)… I wish it were something i can be remunerated for.

  2. Job Title: Bringer of the past to the present.
    Job Description: Not a historian, who attempts to reconstruct the past. Not an author of historical fiction who attempts to take the present to the past by projecting stories conceived in the present into the past. The Bringer of the Past enhances the present by tracing the present’s roots in the past, which provides a fuller understanding of the present. The world today is in the throes of change and many think they are, for good or bad, diving or being cast into a new world where old rules and concepts no longer apply. They are at sea far from the sight of land, but the land is under their feet if they were to put their feet down and stand up. The Bringer of the Past knows that the rules and concepts for the future are contained in the past. If something appears new, it is because we lose sight of its past in a new environment. The Bringer of the Past pulls the past close to offer understanding of the future.

  3. Stella C. Theriot says:

    The job title that doesn’t exist that I would like to create is a C-level position . As Creative Comedic Cheerleader (CCC) / Funky Artistic Nurturer (FAN), I would utilize my positive attitude and unique perspective on life to encourage others via blog pieces, in-person and online presentations, social media posts, and any other avenues to reach people.

  4. My dream Job Title is “Marketplace Diplomat”
    Job Description: Creative thinker with extraordinary communication skills and proven business capabilities will bridge the chasm between divisions and foster collaboration between marketing and engineering, sales and manufacturing, research and regulatory. Individual will be deeply intuitive and exhibit right/left brain balance. Diplomat will be charged with fostering communication and cooperation throughout the workforce, building frameworks for alignment and orchestrating harmonious partnerships within the enterprise.

  5. Creative Existence Enhancer

    Thanks Mark – great series and this last episode was very thought provoking.

    Listening to Aileen I got a sense of her as having her creativity really at the service of others. She is all about branding and the company experience. Her quick wit and intelligence are really honed in on that. I was very impressed by her way of thinking.

    I have to admit, I was impressed and intimidated ! She is so literally “on the money”. I feel like I’m some arty airy fairy type listening to her ! I know these are all ridiculous arguments but I just thought it would be nice to disagree slightly. Its not so much that I disagree but I think that some creative jobs just do not exist at all.

    What I feel is that creative people really do develop extraordinary skills and some of them are directly and easily applicable to the business world. Some of them however, are not as easily applicable. I know this is not at all what you intend by the creative challenge but sometimes we develop skills where there is no point in trying to lever them into the business world. Sometimes those artistic skills are good enough to exist by themselves.
    I’m not a penniless artist but I’m not far from it… like many creative types I make my money from other jobs.

    Poetry could be applied to business in interesting ways, I am sure. Sometimes I prefer to take refuge in poetry even though I am sure the poet is also a teacher, or a copywriter…

    I tried the creative challenge and I came up with things that I can do artistically but I really feel some of my skills are so niche that I cannot imagine how to fit this particular peg into that square hole. I do lots of different things as it is, and in some of them you have to really put a lid on your creative aspects… at first anyway. Then as you go a little deeper you can see that people love the creative aspects. I would love to be able to be totally transparent about my creative skills. That is not in everything I do of course but in France they have strange expressions like “comme un artiste” meaning that you are disorganised and shambolic. So in certain contexts you have to keep it quiet. It is a little like what Aileen mentions when she says jack of all trades and master of none. So I do not usually tell people everything I do.

    I think the fact that we can do many different things is actually an advantage, it is a capacity to build links. The downside is that you can get lots of projects on the go but not finish them correctly. And also you can get a lot of negative attitudes from people around who do not understand and who can also just be downright jealous.
    While on the subject you should check out Emilie Wapnick, who uses the expression multipotentialite and could be interesting for the next season of your podcast.
    Anyway here is my dream job opening

    Wanted : Creative Existence Enhancer
    Profile : Able to link diverse people, objects and ideas in a creative manner. Knowledge of diverse creative approaches and concrete exercises to coach people and organisations how to produce creative solutions. Shows people how magical their existence is.

    Skills : disinhibited and capable of disinhibiting others. Create poetry without other people realising that poetry it is, and thereby allowing all to access realms of infinity previously unsuspected. Can rhyme but not required ; written, spoken or performed.
    Distance allied with surprising proximity permits people to think critically about their masks and public persona. Showing chinks in personality shell with equal mix humour and drama sends messages deeper.
    Performance skills required : trumpet playing, singing and dancing but at beginner/ intermediate level that allows others to project themselves in an entertaining fashion (“anything you can do, I can do better”). Happy to do all of the above in underpants.
    Essential : able to get behind words that are used.
    Teaching : experience of at least 20 years, meaning knowledge of group dynamics and able to read groups, create atmospheres where individuals (both introvert and extrovert) feel confident and relaxed.
    Soft skills : Seduction of the secret part of each individual through a mixture of humour, originality and appealing to truly humanistic values.
    Confidence in public speaking and ability to improvise anything in front of groups of up to and above 10,000 people. Enjoy applause, heckling and booing as different manifestations of interest.
    Drawing skills : figurative drawing skills through 40 plus years observation of real and unreal worlds, links between dreams and reality. Capacity to lift details and to imagine other scenes with no link to reality. Persistence in bringing these visions to fruition. Will and can work from photos or life. Interest in teaching others how to enjoy their own drawing. Drawing used as a form of meditation. Drawing in pencil, ink and with colours. Painting not essential but appreciated.
    Link between drawing and performance. Gestural aspect of drawings in relation to scene that is portrayed and gestures in performance. Can and will do illustrations, fanzines, record covers, merchandising…
    Good humoured, enjoys working collaboratively, highly prolific. Joie de vivre. Sensitive and also insensitive.
    Also : this job will only be given to a person we already know. We are just putting this ad out here to pretend to recruit openly but in fact we have already selected the perfect candidate.
    Please apply even though you don’t have a snowball’s chance in hell anyway with your CV and a letter of introduction.

    Thanks for a cool creative challenge ! And sorry for a really long post but it really made me think a lot – really looking forward to the next season !

  6. Job – Resident writer, hermit and garden elf at a secret garden.

    I’m a professional gardener and so I have a lot of gardening skills that would go unused if I became a full time writer so I think writing from a hidden woodland hut on the edge of a secret garden would suit me. I would also have responsibility for maintaining the magic of the garden; making unexpected plantings, creating small works of garden art and encouraging the wildlife.

    • adore your job title:))) a garden elf at a secret garden!!!

    • Libby, did you know that being a professional hermit was totally a real job in Victorian England?? It was very fashionable to have a hermitage on large estates and to keep a hermit there, who would generally add some kind of artistic legitimacy to the area and the estate owner. Sometimes they were musicians or writers or holy men. Often they had a bit of land by the hermitage they could garden in, although it was considered barbaric not to feed your hermit from the estate’s kitchens. This is a real thing!

  7. Position Title: Happy Families Creator

    Requirements: The successful candidate possesses an extensive education in human development and a good understanding of what makes people – children, especially – tick.

    The candidate’s communication skills are impeccable, and used to help parents understand why their children do the seemingly insane things that they do. (Sample question from actual parent: “Why, after I read my 5-year-old the riot act for unreasonably not wanting to go in Daddy’s car at all ever again, does she clap and cheer about going in Daddy’s car the very next day?”)

    TSC (The Successful Candidate) uses these communication skills to conduct interviews with people whose ideas will help parents feel better in themselves, in their parenting, and get along better with their children. TSC is expected to interview a wide-ranging variety of guests, from the sitting President of the American Academy of Pediatrics, to former Assistant Secretaries of Homeland Security, to authors of New York Times bestsellers, to the sometimes confused and often bewildered parents themselves.

    Ultimately, TSC brings together the key traits of:

    – Chutzpah to learn about all the different technologies necessary to create a website, podcast, and private coaching group including forums, courses, and parent coaching calls
    – 8-10 years’ teaching experience with young children; included in this experience must be learning to aid parents as they help their children (those with special needs and more typical development) interact with the world around them, and learn, and grow
    – Mom or Dad of, at youngest, teenagers (so that TSC can make all the mistakes – and learn from them – that his/her clients will need advice about)
    – Demonstrated ability to help people understand their children
    – Outstanding communication skills to help parents act in ways that foster happiness in their families

    Does this sound like you? Please send cover letter, qualifications, and a large packet of Swedish Fish candy to the We Turned Out Okay podcast.

    (This job posting went up in 2015 and was filled in May of that year by Karen Lock Kolp, M.Ed. She’s been podcasting and creating happy families ever since, and hopes she’ll be forgiven for contributing to this challenge with a job that does actually exist… It did not before she created it in May 2015 : )

    • Literally my first thought as I opened my eyes this morning: “that’s the wrong job title!”

      Parents already have everything they need inside themselves to create their happy families.

      I facilitate, help bring out, these traits with and for parents.

      That makes me, not a Happy Families Creator – but a Facilitator of Happy Families.

      So, that’s my job title!

      Thanks again, Mark and Aileen, for this challenge. It’s helped me think differently about the job I’ve created for myself.

  8. Job: The guy at the bar.

    You know, the one you can share all your ideas & dreams with because you’ve had a couple of drinks and fear and inhibitions are low. And most importantly, you don’t know this guy so your not worried about being judged. Also this guy is so excited and encouraging and gives awesome feedback. You leave the bar ready to launch your dream! Everybody needs some of that positive, non-judging encouragement and feedback. That’s me, the guy at the bar!

  9. Coralie Rozenblum says:

    Job title : An Incarnated Sourcerer

    Job description

    Search for what is sparkling, bubbling, vibrating underneath the stagnant, obstructed, cluttered state of a person’s life be it its mind, body, spirit as well as its environment, relationship, ideas, goals, dreams…
    May include some tidying up workshops, some nature exposure, some bodywork endeavour…
    – to get in touch with the core or heart (or the cœur in french) of one’s source
    – to bring movement, energy’s flowing and sensitivity/intuition’s back
    – help find one’s own ressources (internal/external) to keep that source alive and well.

    Part of the job will also be to motivate the ones who
    – teach, train, animate workshops… to embody their knowledge and making it alive for students
    – learn (or/and want to learn) to know what’s important to them to learn and find out how they enjoy learning.

  10. I am a Proper Problem Pinpointer. All my life I’ve seen people struggle to solve problems because they were working on the wrong problem. I was born with an almost magical ability to start divergent and move toward convergent, to see grand chaotic tableaux and find the pattern that points to The One Thing.

    Here’s the challenge I’ve had with ever turning it into making a living: when these things are pointed out, they are invariably infinitely obvious after the fact, like knowing how a magic trick is done.

    And then everything thinks hey, that was easy, I could have done that myself.

    It would, though, be nice to be able to perform this magic trick while looking in a mirror, ’cause that guy often misses some very obvious stuff . . .

    • . . . everyone thinks . . .

    • Finola Jennings Clark says:

      this is kind of similar to my first idea for a job that doesn’t exist title – “finder of treasures hidden in plain sight’ – the things that you think, “Damn, that’s EXACTLY it!” – they happen randomly in life when finally the way someone suggests something to you, resonates and you have your ‘Aha Moment’.
      I’ve realised I’m good at helping people see something that’s just hidden just a little, it’s the same in my own art and writing, so I changed the title up a bit. It’s been a good exercise for me, trying to tie in very disparate things by pinpointing what’s at the core. Not sure I’m 100% happy with how I’m expressing it as a job title yet, but it has helped in the transformation from feeling like a Jill of All Trades, into something more

  11. I came up with Internal Page Creator. This is how I connect to the world. Using sensory tools like words and facial expressions, I reach into your internal processes. On that page we experience love, we share ideas, and that fuels my creations. I like contextualizing that on two levels. There is the world where I physically express myself, and then a world where I fictionally express myself.

  12. job title: a renaissance faerie

    fine art photographer
    a magic anna pavlova ballerina
    a kate bush faerie singer
    a mary oliver kind of poet
    editor of the faerie tales of violette
    film creator

    such a wonderful brilliant & fun challenge this was:)))

  13. My title would be
    Systems Simplification Engineer

    I would take an overly complicated design for a system (example would be feedwater – to feed water to a system and take out and stop water going into) and question, question, question how to keep the safety features IN but get the extra stuff OUT. This would work for almost anything.

  14. Finola Jennings Clark says:

    This really made me think about how to pull my many-faceted skills into ‘a job’… “Finder, Creator and Sharer of Life’s Treasures”
    I think that covers development consultancy, creating art including photography, writing about life and places and even creating fiction. Sounds pretty corny, but it’ll do for now 🙂

  15. Job Title: Facilitator of Run/Swim/Sketch/Write experiential workshops
    I hold workshops that help people de-stress and start their day in a fabulous creative way. The participants jog along the beach, swim in the ocean, then sit on the sand dunes to silently sketch a found object like a shell and finish up by writing what they see/feel/hear/smell.
    Exercise, nature, creativity, focus and mindfulness all packaged together : )

  16. Thank you for the podcast and this interview. I haven’t listened to the other episodes yet, but will go back to them now. One of the questions on my mind during this interview was how Aileen started out communicating with potential clients about her skills and what she could do to help them. I’d love to hear more ideas about that.

    My title: Human-centered Design Strategist. The work: applying empathy and humanity to organizational and project challenges; helping organizations and businesses create better products and services for their customers and clients; bringing a human-centered mindset to tricky challenges and improving how things get done.

  17. Job title: Traveling Self-Care Expert

    The Traveling Self-Care Expert has your back for whatever you need to nourish yourself in body, mind, and soul.

    Are you burnt out and need a restorative vacation away from all demands and stresses? She can book that for you, and even come with you as a personal guide and translator if you would like.

    Does your body ache at the end of the day and you don’t even know why? She can set you up with the best bodywork or other healing modalities to see that you feel you absolute best all day, every day.

    Maybe there’s just something missing, something unnameable or hard to pin down. The Traveling Self-Care Expert can work with you to name it and actually address this unmet need so that you can live a completely satisfied and fulfilling life.

  18. Thanks everyone, I really enjoyed reading these! The Creative Challenge is now closed for this week – and this season!

  19. You certainly got some pretty cool suggestions.
    Darn it that I missed our deadline, I was hoping to put in a bid as director of marketing and paddle-surf without portfolio.