December 28

How to make the transitions from childhood to adulthood



It’s not fair. University or school never prepared you for adulthood. If you’re struggling today, it’s not your fault. The transition between school to work-life is challenging.

And the worst thing is that how well you did in school has little indication of how well you might do in work.

Why do I say this?

Because from my conversation with clients, and my own personal experience, the academic excellence one shows seems to correlate with poorer outcomes in work.

Why does this happen? Shouldn’t academic excellence indicate that you would do pretty well in life?

After all, how different is work from school life?

In this article, I would like to share

  1. Why school prepares you poorly for work
  2. The four key transitory challenges from childhood to adulthood
  3. The three mindsets that can help
  4. How you can better adjust to these challenges.

Why does school prepare you poorly for work?

Before we look at the transitory challenges, let’s look at why school and university prevent you from transiting well to work.

School supports you to be a worker

Every year, universities in Singapore publish the median earnings of the graduates of various courses. Universities use that as marketing material for why you should enter a certain course. Sure, that works as good marketing. But it won’t work for you.

Are you struggling at work
Struggling in your work transition? Maybe it’s time to understand why.

Because whilst universities can prepare you for how to get a job, they don’t teach you why a job is even important. Or what happens after you get a job.

Universities do all they can to look at your CV, read through your cover letters and guide you in the interview process. But have you thought of the wider life skills of being an adult, and not just a worker?

There’s more to life than work. Here’s a question for you:

Do you live to work?

Or do you work to live?

If you live to work, much of your identity and security is tied up in your work. What happens if you lose a job? Or find it difficult to find a job for the next 6 months? Does that mean that you’re any less?

What will you do then to adapt to the situation of not having a job?

School may not necessarily prepare you for the situations when life doesn’t turn out to be as straightforward as you think.

Let me share my own experience.

I graduated in September 2019. Since I formally ended my job in October 2021, I have struggled to find the next job. This wasn’t what I expected when I first graduated. After all, university painted such a rosy picture of our chances, talking about how they were the ‘Number 1 University for Career and Employability’. It didn’t seem that hard to get a job.

But 60 job applications later, I’ve found that the situation is much different. If I had depended on university to give me the resources to succeed in my job-hunt, I would still be struggling. But what really helped was a different mindset – one that university didn’t teach.

Mindset shift 1: You’re not the customer, you’re the salesman

You were probably used to a certain set of service standards in university. After all, you were paying a few thousands a year for your education. The university should treat you well. After all, you’re the customer.

No longer. When you’re looking for a job, you’re the salesman. That means that no one owes you anything anymore. When I first started looking for a job, I was very angry.

Why didn’t anyone get back to me?

Didn’t they know this was basic etiquette?

Well, it’s not, if you’re not the customer. Just as you would say ‘thank you, goodbye’ to the slimy salesman who tries to sell you something you don’t need, companies may also end up hanging up on you, or ‘ghosting’ you.

Get used to it.

What I find helpful is to tell myself,

It’s their loss, not mine.

Reminding yourself of the value you bring, and the value you leave behind, is vital when you’re transiting between university to your first job. Otherwise, you can find the rejections extremely painful, especially when you take them personally.

Jordan Peterson, the writer behind 12 More Rules for Life, says that a good gauge is to expect:

1 interview for every 50 applications.

You didn’t read that wrongly.

That means that you might be getting a better hit rate on your Tinder account than on your job applications. Thinking of yourself as a salesman also means preparing for the sale, everytime, all the time.

  1. You need to know who you’re selling to.
  2. You need to know what they want.
  3. You need to know what they need.
  4. You need to know what you can bring to solve their problem.
The 4-step framework to selling yourself to future employers
The 4-step framework to selling yourself to future employers

Notice how the first three points aren’t about you, but about your customer? Make no mistake. Your employer is going to be a customer. And you want them to buy you.

Think of it this way. You’re not only selling a solution. You’re selling the problem. You need to make it clear to your potential employers about the pain they are facing, hammer in the pain they face, so that they end up with a bleeding neck (and run to you for help).

Sounds crude? I didn’t come up with the bleeding neck analogy.

Blame Perry, the author behind 80/20 Sales and Marketing.

School gives you work, with no stakes.

What happened if you missed a deadline at school? Okay, maybe you had a few marks off your final grade… but it was no life and death matter, right?

Compare that to your job. If you lose your job, you may not make rent. Or pay for your kid’s school. You risk being thrown out into the streets.

Those are real stakes.

Come on, don’t tell you had an internship.

What did we really do on our internships? Photocopy papers, scan documents, and take coffee to the boss?

Okay, maybe you did something more. Internships are all the fad today, especially when universities are looking to make a closer connection between work and school. But internships still end up missing the point because companies provide work that has low stakes. I remember my first internship where I had the chance to research into two esoteric topics. I had no idea how these topics would contribute to the organisation’s wider work. Nor did they explain it.

I should have asked.

Mindset shift 2: Don’t wait for people to give you what you want, ask for what you want.

After two years of graduating, I’ve come to realise this.

If you don’t ask, you’ll never get.


I used to be passive about what I wanted at work. Rather than laying out my expectations of my supervisor, and seeing if those needed to be adjusted, I waited for her to take the lead. It wasn’t until the end of my job that I realised that I should have told her clearly that our supervisory sessions weren’t working. And that I expected more.

This isn’t about being mean or demanding. Rather, it’s about being clear.

Working in a small company in Singapore, my personal experience has been that colleagues may sometimes go in a roundabout way to tell you that they are unhappy, or to share their expectations of you. They will complain to everyone except the party involved, expecting others to take the lead in solving the problem. It was something I was unused to, especially after moving back from a different culture.

Back in England, it was more common for colleagues to take you aside and have a private word with you in a 1-1 setting.

Asking for what you want can help in the long run.

School teaches you to plan

Remember how university functioned? You went to class, sat in the lectures, did your assignments and then sat for your exams. It teaches you to plan your day and your work.

It doesn’t teach you how to plan to learn.

We are now coming to the part where you’ve started work.

The process involved in transiting between different roles
The process involved in transiting between different roles

As you can see from the diagram above, rather than looking at it as a continuous process, look at it as an interchangeable process whereby you’re constantly transiting between different stages.

This helps you to normalise your transitions, rather than seeing it as something impossible to conquer.

You’ve 90 days to be of value to the company.

Start on the wrong foot, and it will be hard to change the impression of you.

During my first job, I struggled with the transition from university. I spent lunches in a room alone. I hardly interacted with the rest of my colleagues. I was disengaged from most of the work, because I was dealing with the grief of losing everything I had known in England. Rather than taking time to learn about the organisation, I retreated into learning more about myself.

I thought my subsequent performance in the next 6 months would put me in a good place to adjust the perception of me. But it didn’t.

Your first 90 days are the most important days of your transition into your new job. If you want to make the most of it, plan to learn.

Mindset shift 3: Plan to learn, not learn to plan

I never knew how much work needed to go into my transition until I read ‘The First 90 Days’, written by Michael Watkins.

Before I started my first job, I had little idea that the transition began before the job, rather than after the first day. Learning all that I could about the organisation would prepare me to hit the ground running, rather than going in cold. It would have also prepared you for the culture you will face in the organisation.

What you can do before your entry (adapted from The First 90 Days, from Michael Watkins)
What you can do before your entry (adapted from The First 90 Days, from Michael Watkins)

During the first 90 days of my first job, I had a blast! I didn’t think of learning anything. In fact, I thought it was great that I didn’t have to do much to get a full salary. I would spend most of my day researching into Search Engine Optimisation, figuring out how to invest, and surfing the internet, doing the occasional assignment that was sent my way.

It wasn’t until I read Watkins’ book that I realised the focus of your first 30 days should be on learning.

Have a plan to learn.

As Watkins explains, in this plan to learn, you need to have two things. A learning agenda, and a learning plan.

In your learning agenda, you should try to understand the following.

Adapted from Michael Watkins (The First 90 Days)
Adapted from Michael Watkins (The First 90 Days)

How do you go about doing that?

Through your learning plan.

What your learning process should look like (Michael Watkins)
What your learning process should look like (Michael Watkins)

Even if you are coming in at an entry level job, you should try your best to understand different aspects of the organisation.

According to Michael Watkins, there are 4 different aspects of learning you need to undertake.

  1. Technical
    1. technologies
    2. processes
    3. Systems
    4. Markets
  2. Interpersonal domain
    1. Know your boss
    2. peers
    3. Direct reports
  3. Cultural domain
    1. norms
    2. values
    3. Behavioural expectations
  4. Political domain
    1. Know the shadow organisation – the unofficial set of ‘processes and alliances that strong influence how work actually gets done’

Does this sound like too much for your first job?

You’re getting paid for a reason. And rather than looking at it as a crazy assignment to take on, look at it as crafting a master thesis.


The transition between childhood and adulthood involves three important mindset shifts. But more than that, it involves you looking at how you can prepare to drop the models you’ve learnt previously, so that you can learn new ones. Many talk about how you need to unlearn, learn and relearn. I beg to differ.

I don’t think it’s about unlearning what you’ve learnt. Rather, it’s about building onto what you’ve learnt, so that you come out stronger and more adept.

But most importantly, the transition between childhood and adulthood requires curiosity. It can be painful to be searching for jobs, tossing your CV left, right and centre, and hoping for someone to take you on. You may be hoping for someone to give you a chance. But you know something?

You have to give yourself a chance first. More than anything else, this has been the greatest lesson of the last 3 months in my search for a job. Quitting without a job has been a difficult decision. And the past 3 months been the most painful period of my life.

But it has forced me to look at all the times when I refused to be kind to myself, criticising myself for all the flaws I had in my life. But today, I’m reminded that your base of security should come from within. It doesn’t need to come externally, from what’s around you.

Rather, it should come from within you. Because you know the skills, qualities and values you have, you’re proud of yourself for who you are, rather than what you do.

Today, if you’re transiting poorly between childhood and adulthood, give yourself a chance. Remember that you’re more than a job. You’re more than a salary.

You’re more than the rejection you’ve received.

You’re more, because you’re still fighting. And it’s in the fight where you find grit, strength and hope.


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