Want your dream job? Here are the career milestones to hit at every age

When a former colleague, Eliza*, who has dedicated years in tech start-ups, quit and joined a government-linked company (GLC), it came as a surprise. Why the drastic change? 

Then she broke it down for me: The horrendous long hours, non-existent welfare and the “talented” cut-throat slave-driver boss at the start-up was driving her nuts. The “996” work schedule – a term that refers to working from 9 am to 9 pm, six days a week – wasn’t tolerable anymore.

I found out too that her headfirst dive into start-ups wasn’t because she was passionate about them, but found it necessary to help her reach her end goal – a role in an innovation lab.

After years of gaining experience first supporting one tech start-up and then managing another – she eventually landed a role at the GLC’s innovation department, where she now works regular hours and under bosses who genuinely care for her welfare.

I was reminded of her story when former Google executive Rajan Anandan announced that he’s leaving Google after eight years to join venture capital firm, Sequoia, on developing Surge – a scale-up programme for start-ups.

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Mr Anandan did not specify the reason to his departure from the Big Tech company, but rumour has it that one of the reasons was to relive his passion in nurturing early stage start-ups. Before Mr Anandan took responsibility in driving Google’s growth in India, he was an angel investor, supporting Indian entrepreneurs.

Eliza and Mr Anandan’s careers pathways are very different, but they both demonstrate how life stages bring about different needs and wants for us all, and planning ahead in your career might give you an edge in landing your eventual dream job at 40 or so.

So how do we get there? 


In planning for future jobs, take a few minutes of your day to ponder on the ideal role you want to be in 10 or 20 years’ time. Then, look for clues to help you craft your own path.

That can include looking up and tracing the journey of someone who is in a position you want to reach for in the future.

Want to work in Facebook? Dan Neary, the current Vice-President of Asia-Pacific at Facebook for example, built his career in big names – Skype, eBay and Kellogg among others, and has experience building partnerships in China, Europe, Middle East and Africa. 

But for some unsure of their end-career goal, it’s going to be more complicated.

Still, life presents many twists and turns that may change your values or perceptions, and staying open-minded and attuned to changes about what as a job gives you satisfaction can beneficial. Just count the number of banker-turned-farmer or baker or teacher.

But ultimately, what you may want to focus on is what you can achieve within each decade and how those could snowball into something valuable along the way.


Most people see their 20s as a foundational decade to gain news skills and relevant experience in a specific industry or function.

But instead of using these years to narrow yourself into one kind of role, it should be a discovery decade where you figure out what you’re good at and what parts of a career give you the most fulfillment.

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My nephew had wanted to be a successful financial consultant like his aunt whom he saw as a role model. 

But after getting his bachelor in accountancy, and joining one of the Big 5, he realised that it just wasn’t enjoyable. He finds it more fulfilling in his current job as a corporate relationship manager in a local bank.

When I started my first recruitment business at 24, I was very sure I wanted to do that for the rest of my life. 

Over that 11-year journey I learnt how to run and manage a business that includes managing cash flow, people, marketing, and the media. I picked up an important skill too – public speaking. 

While that business didn’t last, the skills and knowledge I gained were things only experience could have given. And that experience opened up many other opportunities.

Experience points accumulated during your 20s are like shiny badges: Important to attract attention of headhunters or companies in the future.

Time is the only currency of abundance at this point. Get involved in other works like charity, or a pet project. They may grow into passive income streams or help you grow your network.


Companies setting up big offices here in Singapore are likely supporting Asia-Pacific offices elsewhere in the region. If you are working in one of them, aim to get regional exposure. This would prepare you for future opportunities. 

While relocation for an overseas assignment may mean three years or so in a foreign country, the achievement will be engraved in time on your resume.

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Going overseas, moving beyond your comfort zone and proving that you can survive under ambiguity make you an asset in the eyes of future employers.

If your current company doesn’t provide overseas postings, you should check out if close competition can provide you with those opportunities.

As Reid Hoffman mentioned in his second book The Alliance, one should look at each employment as a tour of duty. Get what you aim for and then move on to the next bigger role.

Most importantly, the move should put you closer to what you want next. If you’d like to jump into the Japan market, it would make more sense to join a Japanese company.


Professionals, managers and executives in their 40s will most likely be very highly skilled in their area of expertise.

If you are a Gen X reading this and have yet to market yourself, it’s not too late to build a personal brand. Put yourself on career social media platforms like LinkedIn, go to networking sessions, or speak at events.

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Be an expert who can offer advice and opinions in matters related to your job role and/or industry. 

This can make you a thought leader in the process. And chances are if you are in a senior management level, you may even be invited to deliver a public presentation to share your insights.

My career coaching client-turned-friend Ram Dubey did just that when he transitioned from a banking career to counselling. And what better way to cement your authority by giving out a published book as your calling card.

Ideally, we should aspire to be like Rajan Anandan in his 50s: Mentoring others to help boost their businesses and career potential … rather than grinding it out yourself.

Even if that is not going to happen (there is only one Rajan Anandan after all), a firm career footing with decades of accumulated experience should put you in a good state to pursue your version of meaning when you hit your 50s.

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