When we began to write this, we thought it might be a mirror reflection of an article we wrote about for-profit executives moving into purpose-driven roles. We had the somewhat naïve and possibly judgmental hypothesis that a transition the other way around involved some sort of selling out. Through the diverse stories that follow, we discovered some illuminating advice on how to thrive in a career that takes on a chiaroscuro quality – a study of deep contrasts in light and dark.

The provocative Serbian journalist who enlightened energy and tech sectors

Tanja’s quest for justice and human rights started in early childhood. At 6, she was taking karate lessons “to fight bullies and protect the weak” and was soon circulating petitions. Pursuing a childhood dream, she became a journalist, even though it involved being beaten over the head at student protests by the police, under the autocratic regime of Slobodan Milosevic in her native Serbia.

However, after publishing an article criticising police corruption in one of the few opposition-led newspapers in the country, Tanja was subjected to a heavy interrogation and forced to leave her career. She then worked in schools on digitalisation projects which led to a post as the right hand to the Minister of Finance. Having heard that “other earning opportunities were significant”, she left a few days later, disillusioned.

After further studies, Tanja landed a role heading a team of PR professionals in the Serbian judicial system. This was a potentially “dark” place, but her work increasing transparency resulted in an international prize. She began to understand that “good” and “bad” could meet at interesting crossroads, and that there was potential for more light.

Tanja then chose to use her vision, conviction and determination to enlighten the petrochemicals sector. She was working in one of the “darkest” industries, but her corporate communications and social responsibility initiatives opened it up to the public and increased accountability. She also established a foundation, which still does important work for society and the environment.

It became abundantly clear to her that the resources of profit-driven organisations provided unparalleled opportunities to do more good. This persuaded Tanja to join Microsoft eight years ago. As she says, when “you take money from the for-profit and donate it to purpose-driven parts … the feeling is completely Robin-Hoodish!”

She admits that learning to be a diplomat has been hard, and she still asks those “questions that not everyone is ready to answer”. She now measures her success by whether she has achieved one positive thing a week, by teaching someone something, improving a small business function, or helping an organisation.

While she misses her days as a journalist, Tanja is also lucid about the current state of journalism and wonders if she would thrive in that environment. Her advice to aspiring Robin Hoods: “Make the starry sky together and light your way. A lone star can never give enough light, and so it usually just burns out on its own.”

The South African doctor in corporate America to advance global health

Growing up in an open-minded and privileged household in South Africa during apartheid, Derek questioned why suffering, physical or otherwise, was so unfairly distributed. He chose to pursue medicine, a profession where he could have an impact.

Early on, Derek chose to work in epidemiology, at the frontier of research into how health was affected by class, ethnicity and education in this deeply divided society. As apartheid faded, the academic boycott of South African doctors started to lift, opening up an international horizon. After researching HIV and tuberculosis, he became interested in reducing tobacco smoking around the world.

Joining the World Health Organization as their first South African medic in thirty years, Derek soon got involved in a host of anti-smoking projects. He was part of the group behind the world’s first international health treaty, which led to sports stadia across over 180 countries to become smoke free.

Tired of UN bureaucracy, Derek left for a stint at Yale, where he discovered the value of working with – instead of against – the “bad guys” in the food and pharmaceutical industries. He participated in the creation of a private-public partnership including Novo Nordisk, McDonald’s, PepsiCo, Nestlé and others committed to gradual change “for the better”. He felt more and more comfortable straddling ideological bridges if it meant speeding up progress towards the prevention of chronic diseases.

That is when PepsiCo persuaded Derek to head new initiatives aimed at accelerating the transformation of its portfolio. Backed by CEO Indra Nooyi, these initiatives focused on creating healthier products and changing consumer behaviour. But many in public health accused Derek of turning to the dark side. The fact is, in the nearly six years he spent at PepsiCo, he helped remove palm oil from the group’s products in Mexico and, alongside other food giants, trimmed a collective 6 trillion calories from the diet of Americans.

Derek later joined the Vitality Group, a company that incentivises people to adopt a healthy lifestyle. Although the firm had its own, clearly lucrative agenda, engaging with insurance companies for mutual profit, evidence-based reports and papers show that the tools he helped develop genuinely increased life expectancy.

The latest part of his journey to the “dark side”  began after Derek wrote an article on “tobacco harm reduction”, a public health strategy that seeks to lower the health risks of classic tobacco products by substituting them with e-cigarettes and other less harmful nicotine products. It attracted the attention of the CEO of Philip Morris International, who invited Derek to set up an arm’s-length foundation, Smoke Free World.

Despite Derek's repeated assertion that the foundation’s funds are firewalled as required by US law, the WHO has banned him from its conferences. Yet, he remains convinced that a tobacco harm reduction strategy could reduce adult mortality rates faster than campaigns limited to educating children not to start smoking or vaping. Based on his calculations, scaling up this strategy could save 3 to 4 million lives per year for the next three decades.

Throughout his journey, Derek stuck to his convictions and avoided taking criticism too personally. His advice to those who want to change the world is “Do the research, know more than the others, and explore things far beyond your specialised subject.” He also stressed the importance of delayed gratification, as change “takes a long time”.

A serendipitous path from public service to venture capital

The son and grandson of Holocaust survivors, Jean-Marc grew up in a socially engaged, expatriate environment. Dinner conversations, whether in Geneva, Paris or Brussels, often focused on human rights. After attending boarding school in Israel, Jean-Marc went to Sciences-Po in Paris, which deepened his sense of civic responsibility.

Returning to Israel, Jean-Marc entered a yeshiva, or religious seminary, before undertaking law studies. But unlike his classmates who joined well-heeled law firms, he took roles with the Ministry of Justice and the Prime Minister’s Office, which enabled him to influence human rights, welfare and diaspora issues.

He next joined the United Nations High Commissioner for Refugees as a legal advisor. Seeing people’s despair as well as their hopes, he fell in love with the cause, which led him to do volunteer work in NGOs. He was then approached by the JDC, a Jewish relief organisation known as “The Joint”, to do fundraising work. While the causes embraced by JDC resonated with Jean-Marc, he wondered how he could be of use as he did not know the first thing about finance. Fortunately, recruiters allayed his fears by placing value on his transferable skills, such as his command of many languages, as well as his extensive network.

Jean-Marc had a fortuitous lunch with a JDC donor, who wanted to include him in his plan for a venture capital fund in Israel. Again, he was puzzled by the offer, but the donor explained that he trusted him and saw his potential as an interface between the fund and investors across the world.

Over the next few months, the offer from the venture fund, called Crescendo, rolled around in Jean-Marc’s mind. As he negotiated terms, such as having the scope to seek impact investment deals over pure profit ventures, it occurred to him how this looked like a move to the “dark side”. But he realised that he loved the privilege of being the agent who brings meaning to the donor and that there wasn’t a large difference between a donor and an investor.

When he started at Crescendo, Jean-Marc was dumbstruck by the contrast between the sleek space full of glass walls, fine art and beautiful people, and his previous offices in run-down, often makeshift accommodation. He soon discovered that he had a special role to play. He could be the link to the real people needing help on “the field” as well as that of infusing conscience or heart. An ideological realist, or a realist dreamer, he brings impact opportunities to the group, and continues his NGO work alongside.

Jean-Marc’s advice to anyone wanting to work at the intersection of the wealthy and the field: “Do anything and everything when you are starting out. Enrich your horizons and thinking. You can see great or terrible leadership in the smallest of restaurants as well as in glass skyscrapers.” With a sense of curiosity and an open heart, discover what inspires you. And remember that sometimes the less direct path to your destination is the one you are supposed to be on.

Bringing light to the darkness

Is there, indeed, a true dark side? We struggled to find a story totally devoid of light. Of course, we did not interview leaders of companies using child labour in Asia or bosses of blood diamond mines in Africa, who probably never set out to do good as part of their careers. It is also worth mentioning that we received a pushback from some professionals who were perhaps less proud of their career trajectory. What is certain is that it is quite possible to weave a positive path through industries and sectors perceived to be “bad”, without compromising one’s values.

Nine tips for making the move

1. Be clear about your true purpose and personal values before switching.
2. See the move as one that allows you to explore new ways of doing good.
3. Appreciate that resources – money, knowledge or technology – are the key to greater impact.
4. Be prepared to negotiate your terms and defend your boundaries.
5. Know your transferable skillsets and be open-minded about using them in novel ways.
6. Get ready to have your ego and personal identity tested.
7. Stay true to your moral compass.
8. Don’t hesitate to keep a broad mix of activities if it creates a balance.
9. Spot the links and connections between both worlds and be ready to walk that space.