March 6

Have hope: How Falling Behind In Life Can Get You Ahead


As a self-help junkie, I know all the advice out there about comparing.

About how social media prompts you to compare more. And how you should stop comparing, because you’re always the ultimate loser.

So I was caught flummoxed and poleaxed when I found myself in a secondary school class gathering, and quietly feeling desperate, as my friends started talking about the kid that was coming, the condo that they were going to buy, and their wedding plans.

That might be you today.

You might be between jobs.

Or find yourself diligently swiping the dating app, hoping for the special one to come through.

Or you might be sitting in a gathering with friends, hearing them talk about the experiences they have flying country to country, going onto bigger things, and you think,


Where am I going?

If that’s you today, what I really want to say is this.

Falling behind is a good thing.

Nope you didn’t read that wrong.

Falling behind can push you to greater things.

Often we want a tidy narrative to progress

Look at the Singaporean narrative of progress and you will see something similar to:

  1. Study well at your PSLE,
  2. Get into a good secondary school,
  3. Then a good JC/poly,
  4. And then a good university,
  5. Before getting into a good job,
  6. Finding a partner, getting married, having kids,
  7. Progressing onto better jobs,
  8. Before finally retiring with a happy family.

This is neat and tidy. And it’s tempting for us to feel like our life isn’t working out when our lives don’t follow this narrative.

You may feel like you’ve just come out of your first job, and you’re not very clear about what to do next.

Or what you’re good at.

You may not know how to progress in your career. Do you study more, or just work in the same industry?

It’s easy for me, the writer, to plonk you on the head with more studies about how some of the most accomplished people haven’t necessarily had a neat, steady path to progress.

But you might think,

That’s them, this is me.

Stay with me.

It’s okay to specialise late, very late

In your twenties, you might feel that if you haven’t landed on your dream job, and found your best strength, and found yourself steadily climbing up the corporate ladder, you are failing.

Nope. You’re not.

You’re actually having a valuable learning process.

You’re optimising for match quality, or the quality of the fit between yourself, and your career.

You’re rapidly discarding what doesn’t work, for what works.

Ibarra, a professor of organisational behavior at London Business School was studying how young consultants and bankers were doing in the careers.

You might relate to this as you hear about your young consultant friends talking about how their companies are flying them here and there for job opportunities.

But a few years later, whilst following up with them, she realised that these budding stars had moved, or were thinking of moving. She

“concluded that we maximize match quality throughout life by sampling activities, social groups, contexts, jobs, careers, and then reflecting and adjusting our personal narratives. And repeat.”

Excerpt From: David Epstein. “Range: Why Generalists Triumph in a Specialized World”

Therefore the time you’re spending now changing jobs, searching for fit, is a precious time to build lateral skills, in different areas, rather than deeply specialised skill.

That’s why the first step is to see this as a ‘learning phase’, rather than a ‘failure’.

Rather than thinking that you’re falling behind, enjoy the process of learning different things.

When you feel like you’re falling behind, see it as a sampling period

I trained as a social worker, a highly vocational, very specialised degree for 3 years, in the U.K., at a cost of $160,000.

I came back in September 2019, worked as a social worker for 2 years, quit in October 2021.

And promptly found myself rejected by 106 different jobs.

In the meantime, I had to find some way of earning money. I went back to writing, training, and speaking.

Between October 2021 and September 2022, I wrote, trained (on things like how to transit to university), facilitated focus group discussions, and even became IT support.

It did seem like my work was all over the place. And a typical employer would have seen me as 'confused'.
It did seem like my work was all over the place. And a typical employer would have seen me as ‘confused’.

All these were on an independent basis, under the auspices of my own private company (which made it much bigger, and better than it actually was).

Sometimes I didn’t know if I could even eat more than baked beans.

It was finally in September 2022 that I finally made some headway. One day someone asked me if I could make websites for them.

I didn’t know how to, but I just agreed.

And slowly, this grew to become more.

From working with people in social work to working with computers in web development, this seems a very unconventional path.

But it’s more common than you might think.

Leonardo Da Vinci is a famous example of someone who had 5 different careers, from designing war machines to painting.

No one would say he was unsuccessful.

If we look at the world of music, we would also realise that many exceptional musicians were trying as many as 3 different instruments, before they finally settled on the one that they would be famous for.

Exceptional musicians tried more instruments, before settling on the one.
Exceptional musicians tried more instruments, before settling on the one.

Sample more, before you settle on one.

That’s why seeing this time as a helpful sampling period, rather than just you falling behind, can help you to stop feeling like a loser when you meet your friends.

Falling behind might actually make you better

But we like tidy narratives, because they are easier to follow.

Tell someone that all they need to do is get a good degree, before their career is set to fly, is much more convenient than telling someone that they will probably go through a time of confusion, and not knowing.

What if I told you that falling behind might make you better, not worse?

The path to success is not neat, and definitely not a straight line. Credit: David Epstein, in his TedxManchester talk "How falling behind can get you ahead".
The path to success is not neat, and definitely not a straight line. Credit: David Epstein, in his TedxManchester talk “How falling behind can get you ahead”.

When I kept getting rejected from jobs, the one common feedback that was given to me was that it seemed like I had many different experiences, but no one defining expertise.

That made it difficult for them to choose me.

For some time, I thought it was bad to be interested in so many different things.

Until one day, a friend told me that being interested in many different things, was not a curse.

It was a gift.

You might be in a position today where you find yourself having a surface knowledge at many different things.

People call you a generalist. You might even call yourself that.

People don’t mean that as a compliment. It’s supposed to be derogatory.

But putting yourself down for being good at many different things, and not excellent at one single thing, isn’t the way to go.

Instead, it’s about realising it’s good.

Then it’s about making it valuable.

Many companies and people won’t be able to see that.

But you have to see that yourself.

I found my way by starting a company, because that was the easiest way to combine many different skills at once.

You might find that your outperformance comes when you’re in a role that brings together many different skillsets and knowledges.

Here there’s a difference between skills, and knowledge. Many use it loosely, but there’s a subtle but vital difference.

It’s about realising that skills are those you can do well in, whilst knowledge is what you know.

Often these places where you thrive may be in fields that are blue-sky, which mean that things are not known very clearly and there’s more space for experimentation.

It may also be in roles that call for creativity, so roles like:

  1. Product development
  2. R&D
Early peakers, may not beat late bloomers. Credit: David Epstein, in his TedxManchester talk "How falling behind can get you ahead".
Early peakers, may not beat late bloomers. Credit: David Epstein, in his TedxManchester talk “How falling behind can get you ahead”.

But ultimately I think it’s this.

Sometimes, I do feel sheepish when I tell people that I did well at the Primary School Leaving Examination (PSLE) in Singapore, graduated from an elite school, won an overseas scholarship, and then got a first-class honours.

Because if they look at me now, where business is a struggle (but very fun), at how I’m unmarried, how I don’t have a big retirement account, I might look like a failure.

But my belief and hope is this.

Early peakers or late bloomers, you’re on your own journey.

And falling behind sometimes isn’t all that bad.

It gives you perspective of the pack, so that you can get perspective on what really matters to you.



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