Side Hustles, Slashers, and Second Acts

Creative Life

Steve Stine was always clear on the strength of his network.

Over thirty years and while evolving his career from journalism to management consulting to business advisory, he developed and tended to relationships across the region. When he moved into the executive search business, joining Heidrick & Struggles in 2008, he had a ready-made network at his fingertips.

He has also always been passionate about storytelling. To feed that curiosity, in his spare time he studied for a master’s degree in mythology from the Pacifica Graduate Institute in California. Steve followed his offbeat tendencies as head of his firm’s Asian region by negotiating to live in Bali because he wanted his daughters to attend the Green School, an alternative school focused on experiential learning. Stine managed his workload by piling up a ton of frequent flyer miles, visiting clients and staff in different countries and around the world.

Side Hustle

His job and title put him in contact with a rich variety of Asian experts and insiders. Blending an appreciation for “story” with the tale of Asia in transition, he launched what is today Asia’s largest business-focused podcast, Inside Asia. He did this both as a creative outlet but also to enhance and enrich the quality of his network. His storytelling passion makes him very good at it.

Meanwhile, the podcast nourishes and supports his interest in grooming his leadership advisory and coaching skills, as he reaches out to people to join him in conversations. This deepens their relationships to much greater degrees than the traditional transactional nature we’re used to. In fact, his podcast has been so successful, he is thinking about how he can build or partner. His ideas go beyond, to grow a new and independent media brand. That might lead to a completely new reinvention.[1]

Slash Life / Creative Life

Similar to the side project is the “slash life,” where you may have multiple projects or career tracks simultaneously. This movement is based on a book by Marci Alboher, called One Person/Multiple Careers: A New Model for Work/Life Success.[2]

Once the purview of the waiter/actor or receptionist/writer, it is often to combine paying work and creative or more purpose-driven work. This is now morphing into the professional world with violin-maker/psychologist, dentist/NGO leader, pro-athlete/investor or CFO Company A/CFO Company B becoming more common.

In the Philippines, there is an entire movement called “Slashers”: people who focus energy on interests outside their traditional work. They might work as creative directors at an advertising agency then create jewelry on the side to sell on Instagram, using that money to travel (and putting the photos of their travel on Instagram!).

Second Act

As you build up your skills in a new area while continuing your existing role, the time pressure can be intense. Especially if everything gets busy at once but the opportunity to be creative and fulfilled is worth it. If it seems daunting, a second act, or a sort of career serial monogamy, may be more your style.

From a Banker…

Ex-banker Agnes K Y Tai is another problem solver. She is always open to a pivot, who is pursuing a major shift in her work. While she has spent her entire life in finance, she has, in fact, been an entrepreneur. Of course, without necessarily calling herself that. She told me about exploring new financial products and new markets, and about building companies. She certainly had the courage to reinvent herself multiple times as the markets shifted and new opportunities arose.

… To PhD and Sustainability

Agnes has recently passed her PhD qualifying exam, following up on one of her ultimate dreams. After fulfilling various functional roles, she decided to get a degree focused on sustainable investing, incorporating environmental, social, and governance (ESG) factors in risk-rewards analysis. ESG is a very prominent trend. And a way to focus investment on activities that are good for people and the planet. What she found was, that after forty years spent solving problems, she was in a very different environment. She was in a culture focused more on theory than practical solutions.

Agnes had a hypothesis about how this could work. But suddenly found that rather than applying an evidence-based approach, she would have to learn a new method of testing against original theories, with a historical perspective, and carry that forward. She’s soldiering through but in a completely different work environment. Same industry, new environment; always an opportunity to learn in ways we don’t expect.

Reinvention can be challenging, but you too can add a side hustle, slash field, or second act to your life. Build stepping stones to new careers by developing hobbies and the following curiosity as you go along.

Adapted from Future Proof.


[1] Steve Stine (side projects), interviewed by Diana Wu David of Future Proof, September 27, 2018.

[2] Marci Alboher, One Person/Multiple Careers: A New Model for Work/Life Success(New York: Business Plus, 2007).