Singapore ex-pat’s guest post – Jonathan Hardy on moving from a corporate life to the gig economy.

Singapore ex-pat’s guest post – Jonathan Hardy on moving from a corporate life to the gig economy.

In 2019, after a long career in advertising sales, Jonathan Hardy, aged 54, left his company to build a ‘portfolio career’ intended to carry him into the last 10-20 years of his working life. Unfortunately, unpredictable world events, like the disturbances in Hong Kong and Covid 19, significantly impacted his plan almost before it started. However, Jon pressed on and I’m delighted that he’s agreed to share his journey towards his ‘second act.’

Jonathan Hardy

Firstly, what is a portfolio career?

“One that provides the freedom to get involved with different projects and opportunities that align not just with your previous business experience and core skills, but also your interests and passions.”

What was your previous business experience?

“Over 30 years in advertising sales within media and technology companies. I worked for a range of large and small companies which took me around the world. I moved to Hong Kong in my early twenties which revealed opportunities in both the media business and the expat lifestyle that I couldn’t have imagined when I was growing up in South London. I left Hong Kong to work in New York but returned to Hong Kong in the 2000’s where I set up and ran up my own media sales agency. A decade later, in Singapore, I launched the APAC business for a Silicon Valley based online travel advertising start up.”

What prompted your decision to leave advertising and develop a portfolio career in 2019?

“I was thinking about how to create a different, more sustainable and more controllable working life before 2019, because I wanted to do something else with my life. Those thoughts became more focused when my wife, Elaine, fell sick. While she made a full recovery, that experience increased the sense of urgency to live life on my own terms and have the freedom to choose what I worked on and who I spent time with.

Once this idea of ‘corporate escape’ entered my mind, I began to watch and listen to countless second career, early retirement and personal finance videos and podcasts. I created multiple savings and cash flow spreadsheets. It then came down to timing but that was made easy when a round of corporate restructuring allowed me to make my exit in mid 2019.”

Have things gone to plan since then?

“Yes and I’m roughly where I hoped I might be at this stage.

The foundations were laid when I allowed myself a break ‘to just go and do what I wanted to do.’ I pursued my interest in Asian colonial history by training to become a volunteer guide (Docent) at the National Museum of Singapore. This was hugely rewarding. I delved deeply into a subject I am passionate about which opened up a completely new working and social environment. The training reminded me how much I enjoyed teaching and coaching and I’ve since secured a position as an adjunct lecturer teaching a business information technology course at Singapore Polytechnic.

It was also through the museum community that I connected with a Singapore history and culture tours business that needed digital marketing support. Finding a project that combined my personal interest and work experience told me that I was on the right track.

My new-found freedom also enabled me to re-connect with many old contacts without the pre-determined, restrictive agenda that typically defines a corporate business call. I could explore opportunities with people I liked and trusted and with whom I could form very flexible trial partnerships.  As a result, I’m helping an old friend with the global expansion of his health and medical news syndication business.”

What has been your greatest achievement during this time?

“My ability to re-gain control over my time and prioritize the time I spend with my family. This has made the transition truly worthwhile.”

Jonathan and Elaine with their 12-year-old son helping with food distribution to elderly residents in Chinatown during COVID 19 lockdown in Singapore.


What challenges have you faced during this transition period?

“The key challenge was how I identified myself. Your role and position in the corporate world is easy to define and explain. Creating a multi-faceted working life built on a portfolio of opportunities and roles is much harder for people to pigeonhole and understand. I’m gradually finding it easier to articulate, but still lack a simple term or phase to cover it all. Strangely, at times, I also felt guilty about having so much control and being able to do what I want, almost as if aspiring to achieve a good work life balance was wrong.”

What advice would you give someone in their 50s who wants a career change?

“If they know what they want to do, then it’s a case of how best to get from A to B based on individual circumstance. If they know they want to do something but are unsure what, it’s obviously more problematic. You can have a broad vision of what you want and where you want to be. I imagined working in a flexible way with people I liked and projects I enjoyed but not much else. When I started planning, I listed all the things I enjoyed. I thought about how to get more involved in those areas, even if I hadn’t figured out if it would pay. That approach led me to the docent training which has proved to be a key transition point.

Clearly, you still need to do all the sensible stuff around planning finances, ensuring partner and family support etc. But I’m a big believer in mottos like, ‘If there is a will there’s a way’ and ‘If you think you can, you will. If you think you can’t, you won’t.’ With that mentality, achieving a goal often comes down to timing and determination. If you can identify an interest with the potential to lead to a second career, (even laying the groundwork before you leave), you are halfway there. Good luck to those who take the plunge.”

Thank you Jon for sharing your fascinating story. I think it takes courage and conviction to make a leap but it sounds so life-affirming.

I’ll be back on 14th August with Jane Iyer, owner of award-winning Jane’s SG Tours, who will be sharing her admiration and affection for Singapore, her beloved home.

Thanks for dropping by and see you on 14th August.

2 Responses to Singapore ex-pat’s guest post – Jonathan Hardy on moving from a corporate life to the gig economy.

  1. Thanks Liz… & Jon, even tho we’ve now worked together for some time I learnt a lot about you from this !
    I love your attitude & it has been great to collaborate.
    Look forward to more adventures ahead!
    All best, Jane

  2. Hi Jane,

    Thanks for your comment. I agree and I hope that Jon will be willing to share some of them too.

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