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On building ‘career insurance’ & changing Asian mindsets about coaching




I first met David during my stint leading the internship and graduate program for Publicis Communications. At the time David's role was in career advisory and talent acquisition and he was my main point of contact for the annual career fair the industry would host for new graduates entering the industry. So when I started my Rising Sideways project, he was one the first people I wanted to speak to so that we could continue many of the conversations we had years ago about helping young graduates prepare for their career.


I didn't know at the time that he too had risen sideways. Before he pivoted to that role in career advisory and talent acquisition, he spent a majority of his career in marketing. Now he is currently a career development facilitator working with mid-career professionals. An advocate of the Rising Sideways movement, he believes that career success in the future will be about flexibility and adaptability rather than climbing the traditional corporate ladder. Keep reading discover more tips from David about his Rising Sideways journey.



Tell me about career coaching. Is it a trend in Asia and Singapore now?

The concept of career coaching is much more established in the West compared to Singapore. Over there it’s normal for successful professionals to engage a coach even when they have a job. However, in the Singapore context there are 3 barriers to overcome. Firstly, the Asian mindset will question why you need a coach because it might indicate that you are not doing well in your career. Secondly, not many people are willing to pay for coaching services especially when the results are difficult to measure. Thirdly, many of us do not proactively plan our career. Despite these barriers I believe that the coaching industry will gain more prominence now because of the changing work environment.

To my knowledge, it’s usually senior executives who use career coaching services. Do you think that professionals need to start engaging a coach much earlier i.e. mid professionals and fresh graduates?

Gone are the days when you have a stable career and you stay with a company for 20 years. There are constant changes, both voluntary and involuntary, that will occur. Our values and priorities will also change throughout our life and that will affect our career decisions. So if you know that change is inevitable then you should engage with a coach much earlier on to be more proactive instead of reactive about your career. It’s like health insurance. People buy insurance and go for health check ups. So why don’t we have the same proactive mindset about future proofing our careers? Similar to health, even though there’s not a problem now, we should be prepared.


So if people had ‘career insurance’, what would that look like?

It would be a plan, just like traditional insurance, where we feel more comfortable moving forward even if there are uncertainties. Although we can’t totally remove the risk, at least we can be better prepared and know what to do in advance. You would know how to pivot, how much upgrading your skills will cost, etc. Basically it’s about putting a career proof into your life so that you’re more confident moving forward. If possible, engage a career coach to support your ‘career insurance’.

How in your career have you moved sideways?

I spent a good part of 18 years in marketing & communication, I hit a ceiling and didn’t know what I would do next. Internally I knew I wanted to make a change. But I felt comfortable - which is human nature! So that thought of change was with me for 3-4 years. It’s always “I need to do something but maybe I’ll do it next year instead” So it snowballs and no action is taken.

Then there was a moment that I realised that I needed to take action and to make a move. I liken it to the concept of burning your bridge, which in this case means leaving my job and comfort zone. When you have a bridge, sometimes you would not put your full focus on making the change. In a sense you always have something to fall back on. At some point having a bridge is a hindrance rather than something that will benefit me.



Walk me through that process of moving sideways.

When I left my marketing job, I realised that I needed to have something in common with what I was doing previously so that it makes pivoting easier. I realised that I’ve been in the marketing world for years and I know how the agency world works. So I made a change to do community outreach and talent acquisition with the Institute of Advertising Singapore because I like to work with youths, share my experience and taking a role that create more social impact. While it was a different role, my pivot was my industry experience and that stayed the same.

However, I managed to pivot because I took a level down in terms of title and salary. Even though it was a step down, it was a strategic step down, which is an important distinction to make. But there was always constant doubt where I would ask myself “am I making the right move?” Even though it was coming from a good place, the people closest to me would also make comments such as “are you sure about moving away from a good job.” The lesson that I learned was that you don’t have to explain yourself to anyone and you have to trust that you are doing the right thing for you. That’s why it’s important to have self confidence when you pivot, know what interests you, assess and minimise your risk and move forward.


Why was that pivot downwards a strategic move?

It was a strategic move because I knew it would give me a foot into the industry and role that I wanted to get into. I formed new networks and discovered a new ecosystem. It also allowed me to gain new knowledge, build my credibility and achievements which were important when I am pivoting into a new function.

So how should we start thinking about potential for growth?

In the traditional corporate ladder, usually you progress up but you stay in the same function. If your skillset and work experience more or less stays the same, and your salary goes up because you’ve been in the same company for many years, that can be a danger sign. You are becoming more expensive, but the thing you can value add to the organisation or role is not growing. But that traditional way of looking at career growth is going to be a thing of the past

In the new world of career development, you may be a marketing manager, but if there are side projects in other areas that you can contribute to and learn, then put your hand up. That way you can create new networks with other people in the company. It makes you more flexible so that you are ready by the time you actually have to make a change. It’s about preparing for change while it still feels small versus when you don’t have a choice. Career growth need not be just vertical progression, be open to lateral movements so as to gain new work experience and skills, to stay relevant.



How ready do you think the industry is for that change?

In career development there are 2 theories that are very relevant to today’s landscape. The Chaos and Planned Happenstance theories. Overall the essence of these two theories is accepting that you can’t plan for your career 100%. You have to embrace a certain level of risk and you have to go out there and do something. When you’re doing something you create new experiences, opportunities and networks and it might evolve you into something else.

The theory also says that you have to be curious, have the propensity to learn and experiment. With the experiences gained you open yourself to other opportunities that came along.

The industry still needs time to adapt. In the local context, many of us still believe that career success is about climbing the corporate ladder. We define our identity by our titles. And alot of us are still practicing that. On the employer side, a lot of employees still hire by plug and play. We don’t look at the softer aspects of the candidate. How adaptable is this person? Can they shift from one function to another?



Any other cultural factors in Asia that we need to acknowledge?

In the local context, the traditional mindset is that failure is bad for my track record especially when it comes to career development. Instead I would reframe at failure as a lesson learned rather than a failure in itself. If you make the wrong career move, the most important thing is to extract what lesson you have learned, and how you can overcome it. You have to reframe failure so that it’s not an end for itself but it’s something that we can learn from.


What does rising sideways mean to you?

Whether you are taking a lateral or downwards move, people assume that you are not progressing. However, to me Rising Sideways doesn’t mean that you are stuck. It means that you are making yourself relevant by learning new things and embracing new work experiences, growing your career in a more sustainable way.


Spending a majority of his career in marketing, David pivoted to a role in career advisory and talent acquisition where he managed a graduate management programme for new graduates entering the media and advertising industry. An advocate of the author’s Rising Sideways movement, he believes that career success in the future will be about flexibility and adaptability rather than climbing the traditional corporate ladder. He is currently a career development facilitator working with mid-career professionals.

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