Stories of Late Bloomers Who Left a Business Career to Flourish in the Arts

How four mid-career professionals rekindled the creative part of themselves and used their business skills while switching to a new life as full-time artists.

By Claire Harbour and Antoine Tirard

Since the Covid-19 pandemic set its ugly teeth into our lives, many of us have had time and opportunity to explore other activities than those we were used to performing in our daily working lives. The jokes about sourdough bread or beautifully created handicrafts abound, and many of us can be thankful for the sanity that cooking or other more artistic activities have provided along the way. Meanwhile, many individuals from all kinds of backgrounds have chosen, or been forced, to pivot in their careers and some have turned to more creative areas in which to make their living. In this article, we look at a group of four business professionals who pivoted to an artistic career before the pandemic catalyzed such changes. We wanted to understand what factors led them to their choices, the skills that they brought with them, and their outlook for the future in their artistic roles. You will meet a singer-songwriter, an author of fiction, a cartoonist and a painter, who worked previously in strategy consulting, banking, insurance and corporate fundraising. We leave it to you to guess at this stage which one left which sector.

Oliver: Swapping bonds for cartoons

Oliver grew up in a family of artistic and creative people. His Swiss mother had a brother who was a renowned architect and his British father took care of the family business. Throughout his schooling, Oliver won prizes and awards for his work and went to Eton College where he pursued his artistic talent. When home from school, Oliver would relax by poring over and imitating tomes of cartoons, sent to his father from New York, especially inspired by Charles Addams cartoons. He also devoured all he could of the French language comic books like Tintin and Astérix that were sent from the other side of the Channel.

Oliver was not given much choice in his initial plans for study. His school tutors recommended the top art school in the UK. But his father pushed back at this, quite possibly because he had been frustrated previously in his dream of becoming an actor. So Oliver studied Geography at the University of Exeter and then went off to work in “The City”. He found the environment “really good fun: hard work, a great team environment, learning a lot about financial instruments, sales and excellent client service”. And he thrived, from a start at Lloyds Insurance, where he was involved in insuring rockets, satellites and planes; then on to a Japanese investment bank, and from there to the erstwhile Lehman Brothers, at the time a power house in bond trading.

What Oliver experienced at Lehman reflects the cracks in the banking system, even though this was almost 30 years ago. He sensed that the increasingly complex instruments –- like derivatives, structured products and mortgage-backed securities – which he was pushed to sell, were “pretty arbitrary, and I honestly wondered if anybody understood them properly, as I certainly did not”. The firm was on a mission to be more like Goldman Sachs or Morgan Stanley, and Oliver felt less and less a “fit” than before. Sure enough, he was soon invited to resign, and escorted from the building. He struggled for a while, despite clients and competitors rallying round and inviting him to interview all over the City. It was only when the outplacement consultant to whom he had been reluctantly assigned made a comment about how his eyes looked up when talking about cartooning, but looked down when discussing banking, that Oliver was inspired to write a list of pros and cons to explore a radically new career path.

The pros side of the list was filled with “move to the country”, “get a dog”, “spend my time drawing cartoons”, while there was only one item on the other column, which was “money”. While Oliver had definitely enjoyed making money at Lehman Brothers, he realized the City was a train he wanted to get off. So, boosted by a course on how to start your own business, Oliver bought his own computer for the first time – an irony, given he had spent the previous ten years surrounded by at least five screens all day every day. And thus, to the dismay of his father, he became a cartoonist at the age of 33.

Oliver had a head start with his business experience and understanding of client work and this is what allowed him to get off on a good footing. Via friends and family, he was closely linked to most of the PR agencies in London, and the balance, he identified in trade magazines. Every single one received a cartoon from him, and commissions soon flowed for work to be done for their clients, including Mo?t Hennessy, Marmite and more. But it was not instant success, and bills needed to be paid, so there were moments of doubt in the initial years. A chance encounter with the head of the Catholic Church in the UK, Cardinal Hume, in which Hume sidled over, and in the quest of “smelling” Oliver’s sneaky cigarette smoke, gave him wise advice and the faith to continue.

Later, Oliver met his wife, who had also given up a successful global career and was flipping apartments in London. The two set up a publishing house to avoid abusive commissions from traditional publishers, and added greetings cards and merchandise to their range of books and original cartoon prints. Oliver took over as chairman of the board of trustees of the Cartoon Art Trust and co-founded the cartoon museum in London, which provides the opportunity for him to go there regularly and oversee the museum and its exhibitions. His cartoons have become instantly recognizable, whether they appear in The Spectator, The Times, The Field Magazine or Country Life, and he is frequently commissioned to create “deal toys” for big IPO’s or acquisitions, leaning heavily on his City connections, as well as his ability to create lurid but hilarious depictions of all the stakeholders involved in such transactions.

Will Oliver ever do anything else? “The drug of making people laugh is far too addictive to give up. I intend to be doing this until I drop!” His understanding of economic principles gave Oliver the confidence to push his prices consistently up, and to recognize that he is not accessible to all. “After all, you would not go to Tiffany’s and offer 200 bucks for a two-carat diamond, would you?” He also strongly recommends that, however low the starting point, the wonders of compound finance and savings need to be understood by all, but most especially those taking the risk of going out on their own professionally. And most of all, he admits to still being utterly amazed at how the characters develop from a blank sheet of paper, almost without understanding his process. This is a man in love with his career, without any doubt.

Sumana: Shifting from underwriting to songwriting

Sumana is an Indian national who spent her childhood in Yemen. War struck when she was 11, she remembers with awe the repatriation program that returned her to the country that was supposed to be “hers”, but which felt almighty unfamiliar and strange.

Having started school early, Sumana now needed not only to find new friends, but to fit in with students who were older and more sophisticated than her. Connection was achieved via singing, as her voice and performance skills won her a place in the a cappella teams that went out and won competitions and championships far and wide. Despite her artistic talents, Sumana made a “sensible” choice at university and studied commerce and accounting.

As her older sister took off to study in France, Sumana began to study at the Alliance Fran?aise in Bangalore, while still in university. Her talents were spotted by one of the professors, and she was put forward for a role at a Swiss re-insurance firm. The serendipity continued, and Sumana progressed swiftly; by 22, she was an assistant vice president, and ready for a change.

The “change” Sumana was after was somewhat nebulous in her mind, but she knew she had a desire for faraway horizons. France turned out to be the right place for her, and she was offered a substantial MBA scholarship to HEC in Paris. 

After graduation, Sumana joined the insurance firm Allianz, shifting towards Marketing and Innovation roles. She found her work sufficiently gratifying and challenging that she spent seven years there. Right at the beginning of her stint, she was walking through the corridors of the Paris Métro, and caught the strains of a beautiful male voice. Like a sailor to a siren, she was guided towards a dreadlocked musician called Vanupié, and she spent a while, transfixed by his energy and passion. After several days watching him perform, Sumana finally plucked up courage to get into conversation one evening, as Vanupié was finishing up his session. All charged up emotionally, she was deeply hit by the realization that this was what she needed to do: “He woke it up in me and I knew I needed to get back to music, to pick up my guitar and sing”.

Coincidentally, Vanupié also came from a corporate background, so his promise to Sumana that “anything is possible” felt both aligned and credible. She began taking classes with him, and was inspired by both his artistic genius, and his assiduous, humble presence, in the Métro halls every single day. For almost four years, Sumana was doing her corporate job by day, and plugging away at the guitar and voice training in the evenings and on weekends. As she grew in confidence, Vanupié pushed her to see that she could only improve as a performer if she actually performed regularly in front of an audience. So, with no connections to concert halls at that stage, Sumana set out on the path to become a subway artist, like her mentor. She passed the audition process, and the first session approached.

Sumana had decided to “go big or go home” and went to the crowded Montparnasse station for her debut. Vanupié had given lots of advice on choosing a location, for acoustics, security, and so on. Predictably enough, a drunkard approached her, inducing some panic, but, as recommended, she looked him in the eye and continued her song. He staggered past her and returned a few moments later, with a rose, which he deposited in her guitar case with a smile, a small bow, and a “vive la France!”. “What an opportunity to reflect on how most of us judge too harshly!”

Two years of most weekends spent playing in the metro provided Sumana the comfort that she was doing “the right thing, despite the ups and downs that made me question everything along the way”. A sense of schizophrenia began to emerge, as she felt less and less aligned with the flashy offices and the corporate politics of the daytime, while weekends were lived as a totally contrasting persona. She realized that often the “paltry fifty cent coin in the hat felt more valuable than the salary at the end of the month”.

So Sumana began setting up an ambitious savings plan to create a protective cushion, and explored the various administrative actions that would be needed to change her professional status. By the time she announced to her colleagues that she was leaving, she was experiencing absolute certainty as to her destiny, and was delighted to be encouraged on her way, with the door left wide open for a return, if ever she wished.

The reality in late 2018 was somewhat more sobering, as Sumana found herself living in fear and pressure, rather than the sense of liberation for which she had hoped. The notion that “now you are a singer-songwriter” induced panic, and the comment from a renowned music industry pro that “she should probably go back to work” did not help. However, what helped Sumana enormously was her business acumen, and her commitment. Undeterred, she tackled her work like a startup, using her skills in brand building, relationship management, partnerships, pricing, negotiation and so on. With passion and persistence, Sumana built her business solidly, and has gained sufficient momentum to be recognized by the French state as a “professional” musician. She has even begun to do corporate performances, where her unusual understanding of the business context allows her to fit in and be appreciated.

Her advice for those considering the same move? “Getting the finances right to avoid panic later, and surrounding oneself with positive friends and family, giving the naysayers a wide berth”. The magic sauce? “Committing to taking at least one small action aligned to the plan every single day: “over two years, those single daily small actions add up to more than 700 steps, and you cannot fail to progress in this way. Even the smallest thing can open up doors” Sumana sees her own present as “priceless, with no hindsight regrets possible”, whatever the longer term. Look out for her in the Paris stations, or indeed at a post-Covid concert hall near you.

Brendan: Pivoting from fund-raising to painting

Sumana’s HEC MBA friend, Brendan, was clearly artistic from the get-go. Growing up in Minnesota, he drew and painted at the kitchen table alongside his brothers. A specialist arts program in high school encouraged him, and, on admission to Brown University, he stayed within the Arts, but decided to specialize in English Literature, sensing that, beyond its inherent appeal to him, “this might open more doors professionally”.

As Brendan progressed through his bachelor’s degree, writing took over from art in his priorities. He soon moved to London, finding his way into a temporary role in the development department at the Royal Academy of Arts, where he built on some previous volunteer experience in fundraising, and learnt a great deal on the ground. So much so that he was promoted and given a more permanent status, gaining access to more and better jobs in development, including a stint as Development Director, UK for INSEAD.

With several years of exposure to prominent leaders, Brendan’s curiosity about how these “otherwise inaccessible” corporate figures functioned led him to decide to do an MBA, to be educated in business, having not taken that avenue previously.

Just before beginning his MBA at HEC, Brendan took time out to concoct a book idea, but then the realities of intense study set in, including a final semester at NYU. This was the first time he was back “at home” in ten years or so, but he saw this strictly as “just a visit”. However, graduating with an MBA in the depths of the 2010 recession led him to be opportunistic, and he accepted a role at a conservation non-profit in Washington DC.

Only two weeks after moving to DC, Brendan was violently mugged and left for dead, but fortuitously saved by a man who was walking his dog in the area. A long hospital stay was accompanied by an $80K bill, which necessitated that he stay employed as health insurance is tied to employment in the US. Twenty months after the accident, Brendan could see that the role and DC were not a fit for many reasons, so he decided it was time to pack up and go back to Minnesota. Not only would he escape a toxic environment, but his parents were ageing and he felt it was time to see more of them. 

“Near death takes away existential fear. I just knew I would be OK. More grounded.” Brendan moved into an artists’ community in 2012, as a writer, and also decided to re-explore painting. His palette was broad, as he was writing, painting, consulting and job searching. And making sure he kept on saving funds to keep aside for future risks. The painting began to take off, and he found himself in demand for studio and coffee shop shows.

Having set himself a target of “make or break within a year”, Brendan was offered a job as Regional Director of Development at NPR more or less a year to the day after his return to Minnesota. He was so excited at the key role NPR played in Americans’ lives, that he took the job, relegating painting to evenings and weekends. Over the coming months and years, he juggled his two careers, and, to his surprise, began to sell paintings at substantial prices, and could imagine a life in which painting was “his business”. Up till then, he had treated painting “like going to the gym –- something that I did regularly with pleasure and with strong results, but nevertheless not my full-time role”.

The business degree kicked in and Brendan set about planning and analyzing: How many shows? How many paintings? How long was a typical sales cycle? What resources were required to make it all work? He continued his work in fundraising, but also travelled across the country to bigger and more prestigious shows, fine tuning his trade. In early 2019, he officially exited his development role, moving out slowly, and building up his reputation in the art world, to the extent that he was admitted to the coveted stable of Saatchi “Other Art” fairs, both in the US and subsequently overseas.

Then came Covid-19, and all the shows dried up. Every single event was cancelled for a whole year. But, with the crazy travel schedule gone, Brendan went back to the studio, did what he could, found himself creating new channels to market, and selling more than ever. He has been sufficiently emboldened by the commissions and his full order book to embark on a public art project in the offing. He wants to be “part of the storytelling of cities”.

This lifestyle is the perfect storm of all Brendan learnt in business: the high touch client relationship building and management, the gentle follow-up, and the “willingness to put myself out there”. His Luxury Marketing classes from HEC have come in handier than he ever imagined, and he has learnt from the best of the Instagrammers that there are different segments to be sold to.

Does he miss earlier parts of his career? Brendan is fulfilled by sending out a monthly, writing-heavy newsletter, and can see that he might create hybrid art using both word and paint in the future. He is also flirting with the idea of creating a podcast about the arts, to keep up the intellectual challenge he misses.

And advice? “Experiment along the way, ask yourself some tough questions like ‘have you already sold?’ And keep up the day job while you test things out”. Indeed Brendan still keeps a hand in the “day job” mentality, just for an extra piece of security, as an MBA admissions coach. He also strongly recommends becoming part of an artists’ community, sharing how much inspiration can be derived from such a setup. Don’t be surprised to see a creation by Brendan in a city near you over the coming years.

Kate: Navigating new territories as a novelist

Kate grew up a tomboy, having at one stage attended school sporting a crew cut and full combat uniform. Logically enough, while studying for a degree in Psychology, she joined the Territorial Army where she spent five years, first as an officer trainee and later as a Troop Commander in the Royal Engineers.

She then joined global military intelligence publisher, Jane’s Information Group, and her rise was dazzling. A managing editor at 25, she had to curtail her reservist activity, due to lack of time.

Curious about landmines and their devastating effects across the globe, Kate found the opportunity to spend a month in Cambodia, far off the beaten track in the northwest. While there, and feeling overwhelmed by the cruelty of the five million or so mines across the country, an idea for a novel emerged. She had no inclination to write it at that stage, but stored it away with no further thought. 

Kate then pursued an MBA at INSEAD “to enhance earnings and to enjoy the ‘fun’ atmosphere”. This led Kate to a prized job at McKinsey, a star candidate with her mix of leadership, creativity and problem-solving. She describes it as more serendipitous, as she did not have a particular career plan. A Dotcom startup lured her away after almost five years of what she describes as “the best and worst job of my life”. Some assignments had fascinated her, while others had been hostile and uncomfortable for her. She had felt like a fish out of water, but made some friends, including a young woman with whom she talked somewhat idly about “leaving McKinsey to become writers”.

When the dotcom turned out to be less shiny than she had thought, Kate decided to break away and do a master’s degree in creative writing. She was initially rejected due to the fact that, “despite the brilliant idea, your writing is appalling”. She found a way in, eventually joined the master’s program in 2002, and began to improve her technique. Inspirational teachers and mentors aided her in writing a finished manuscript for her novel, White Crocodile, a thriller set in the landmine fields of Cambodia inspired by her personal experience. Her business nose helped her to see that the first challenge of becoming a published author was not to waste time going direct to publishers, but to find an agent. Unfortunately, this stage eluded her, despite knocking “at every door there was in the UK”.

Kate returned to her business work, and spent six years lecturing in Strategy at London Business School, and during this time, had three children. While on maternity leave with number three, she got out her manuscript, and re-read it with a critical eye. She analyzed the glaring faults, and set about rewriting, committing fully to her author career. This attempt led to both an agent and a successful book deal with Faber and Faber. White Crocodile was published in 2014 to great critical acclaim – called a ‘remarkable debut’ in The Independent, ‘a stunning debut’ in the Sunday Mirror and ‘evocative’ in The Times.

Substantial media interest ensued, due to the subject matter, and her career backstory, beyond the quality of the writing. Her second novel, Fire Damage, the first in a series featuring clinical psychologist Dr Jessie Flynn, was published in 2016 to more critical acclaim, followed by Scared to Death in 2017.

One important reflection that Kate shared is how “binary” writing is: “I am lucky to have great publishers and decent money, while many have lousy publishers and no money, or have to resort to self-publishing.” She also states that writing is significantly more competitive to get into than McKinsey, explaining that decent agents receive 1,500 or more submissions per week and read less than half a page before binning or proceeding. Her resilience and persistence have been key.

Another transferable skill that Kate brought to her writing career was focus, beyond her brilliant analytical skills and creativity. She describes numerous scenes of her children “destroying things all around” while she carried on writing, undeterred. She has equally used her skill as a business analyst to decide to end her time as a “series writer” and to focus on a standalone novel, seeing greater value in that direction. Her hunch has paid off, and this new strategy has won her a new, more suitable agent, and a top-level book deal with a publisher.

Her advice for aspiring writers? “Don’t do it!”. Joking apart, repeating her comments about the binary nature of the industry, she reminds us that she “knows literally no other successful writers from a business background”. One explanation of this is the long lead time required to become an overnight success. Most business people cannot take the time in their evenings and weekends to create that, while still working away at their team strategy or balance sheets. Consequently, many of the writers that succeed are actually former journalists, who have time and technique on their sides.

Kate sees herself sticking to her dream job as a writer for the rest of her working life. She is an introvert at heart, and “loves being on her own with her characters, and not having to attend endless meetings”. We can look forward, then, to an endless list of new titles to dig into and enjoy!

How to remain an artist once you grow up

It is heartening to observe, throughout our stories, that it is possible to create such disruptions in a career, with a great deal of determination. Our subjects have toiled long and hard to effect their transformation, and undoubtedly all of them would subscribe to the “not over till the fat lady sings” theory. But it is fair to recognize that the paths they have followed are not to be taken lightly. There is much more work and risk involved in making this sort of transition than would be the case in, say, moving from consulting to industry, or even in shifting to a faraway country and culture. Picasso told us that “Every child is an artist. The problem is how to remain an artist once he grows up”. He also said that “art washes away from the soul the dust of everyday life”. Together, these observations lead us to conclude that deciding to become an artist late is both natural and logical, if the inner child is given audience, and valuable, as the contribution is made to society at large. The only catch is the risk involved, and therein lies the rub.

8 Tips for Succeeding in Making the Move into the Arts

1. Take your time, and be sure this is what you want; experiment for as long as it takes to be convinced
2. Prepare mentally and emotionally for a huge change in the way others perceive you
3. Get your finance right; put aside savings to give you a cushion as things may take longer than you expect
4. Be disciplined, put in the hours and persevere; daily small actions add up to big steps
5. Develop a thick skin, be ready to face greater competition than anything you have ever experienced before, embrace rejection and learn from it
6. Use all your business skills to ensure that your work reaches the intended audience; being an artist also means being a business owner
7. Become part of an artists’ community and create a tribe of followers
8. Keep up the day job for as long as necessary to manage finances, time and sanity

Article notes

• Learn more about Oliver: www.oliverpreston.com
• Learn more about Sumana: www.facebook.com/sumanamusic/about/
• Learn more about Brendan: www.brendankramp.com
• Learn more about Kate: https://www.youtube.com/watch?v=WYgVmjuaEfM 
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