This ONE: What’s the point? The leadership grill, unstuck from tech roles, and job searching in a bad market

Happy This ONE Friday!

As I write this article, I am going to watch the Singapore-China Football ⚽ match in the Singapore Stadium, part of the Asian World Cup Qualifying games. Neither is known to be a great team. China ranks 88th, and Singapore ranks 156th in the world.

One might say, what’s the point! Neither team will ever win the World Cup anyway.


Today’s issue is musing over a classic response called “What’s the point!” when the future looks grim. I will share my personal experience (of defeat), my hard learnings, and how they might be helpful in three common scenarios:

  • Leading an underperforming team
  • Progressing beyond a technical role
  • Job search in a bad economy with high competition

Do you believe in fortune-telling? This is not my kind of thing, but I must tell you a story here. When I was 23 and worked in a tech start-up, the business owner next door claimed to be a self-made astrologer. He took the birthdates of a few of us young employees. As my chart revealed to him, I would author books one day and become well-known. It also seemed that I’d have good luck with real estate and own multiple of them.

Fast forward to today, I am not sure if I lived up to my full potential in real estate, but certainly, I have authored quite a few books by now.

The amusing fact is not that the astrologer was “accurate” but that I couldn’t have been farther from publishing a book at that time. I loved writing since young and dreamed of becoming a big-name writer like Tolstoy, Milan Kundera, or Garcia Marquez. But I soon realized that I didn’t live in a magical country at a fast-changing time with lots of fantastic materials. Nor did I possess any significant literary talent. Low chance of success, and yet it demands an enormous amount of effort.

 “What’s the point!” I said to myself. I stopped writing altogether.

I only started writing again when I found out “What’s the point.” It took me 12 years though, which I could have spent writing, or at least, learning about writing.

This painful loss of 12 years has been keeping my learning alive.


This ONE Idea

If you hear yourself saying “What’s the point!”, turn it into a question and approach it with curiosity.

“What’s the point?”

Perhaps it’s about the learning in the journey. Perhaps it’s about the massive potential you can unlock in your life.


I. Doing Something Difficult and The Leadership Grill

Leadership is hard. Just like how people complain about their bosses, leaders complain about their teams, too. The lazy team. The toxic team. The team that resists changes. The team that defends itself against growth. The leader gets exhausted like Sisyphus who has to keep pushing a rock up the mountain, only for it to fall back again. And then, “What’s the point!” sets in.


Sisyphus statue, image source: internet


Everybody loves good outcomes. Few love the process.

The process of doing something difficult can be a painful quest filled with failure, rejection, and hopelessness in life.

Or we can choose to see it differently. For example, an experiment.

That’s when we can learn to fall in love with the process. That comes from knowing a few facts.

  • The fact that every failure is not failure but a learning itself.
  • The fact that every single improvement is worth celebration.
  • The fact that there is never an end. Success is not a destination but a process of experimenting and learning.
  • The fact that we can never be completely right.
  • The fact that we can still move ahead with what we know whilst knowing the limitations of our knowledge.


Think about how science is always built on hypothesises. We believed in Newton till his first law broke down in Quantum Physics, just like we “believe” in Quantum Physics now while new science frontiers keep getting established.


Quantum mechanics is very worthy of regard, but an inner voice tells me that this is not yet the right track. – Albert Einstein

It is the same in leadership or doing anything difficult. The point lies in the process of learning. Take an experiment mindset and we can move forward boldly and relentlessly.


Image by Issac Young

II. Tech Leadership Transition: Tech to Top

Transition from technical expert to tech leader requires a great deal of mindset shift. This is a process of unlearning what has been true to us for a long time.

Sometimes, this unlearning can feel like a gigantic task. Compared to the logical, rational technical world, the complicated business world may feel scary with its unpredictability. Tech leaders often find themselves not well equipped with the necessary confidence and communication skills, not to mention influencing skills for success.

Some start to believe that they are not cut for a management career, being “introverts.” So, what’s the point of trying if we are not even cut for it?



There are a lot of great introverted leaders in the tech world, just like in everywhere else. Being introverted brings you unique challenges, but also unique strengths in the process of growing into top management.

Click to Read how I debunk the myths about introverts




The keyword is “connection.” Ultimately, a good tech leader connects business and people with technology. This requires a willingness to connect with co-workers, a broader work scope, the bigger organization, and to some extent, the industry.

And connection can be learned. As a coach, my work is to coach connection: connection with oneself (self-awareness), with others (interpersonal), and with the bigger system (systemic awareness).

So, the mountain is not that monstrous nor mysterious. The path is unclear. But you have tools, technologies, sherpas, and food supplies. It’s about time to drop the question of “What’s the point” and self-doubts. Start moving.

III. Job search in a tough market

The job market is bad. The tech industry has been retrenching (both because of good and bad reasons). “What’s the point!” sneaks into the minds of many. And if you are job seeking, you know clearly that losing motivation is the last thing you need right now.

Acknowledge yourself for your insights about reality: that good opportunities might be far and few, that the job search process will take long, and that rejections will be prescribed on daily dosage.

So the question is, how can you honour your insights, and make plans and take actions accordingly?

But hey, if you find yourself anxious and demotivated, you will need to address this question first: “What is the point?”

And this question is not about the outcome such as career growth or stable income. But,

What’s the point in applying for jobs if I will be rejected by most of them?

What’s the point in trying new industries if I may only get it after 2 years?

If you look harder, you will find answers specific to you. But let me share some answers others found for themselves:

  • So that my future self won’t regret that I never gave it all.
  • The job search process is a huge learning experience where I learn about new industries, new jobs through reading up JDs and meeting new people to understand their worlds.
  • It is a rare period in my life when I (am forced to) pause to examine what truly matters to me. Life transforming.
  • The long search process makes me rebuild my personal branding in a way I never considered before.
  • It is an opportunity to get out a sinking ship.
  • I finally get some rest!
  • I learn how to activate my resources and network.

The list goes on.

In essence, shift your mindset of pessimism to one of optimism, go full drive with your resilience and resourcefulness.


Read: “Not Applying for Enough Jobs” – Are You Denying Yourself Interviews for Fear of Rejection?

Read: Job Search after being laid off or a career break

A Reminder on the concept of REST

Cover image, The Myth of Sisyphus, Albert Camus

If you are unemployed, remember Job search is not a full-time work. Beyond a certain threshold, the more time you spend thinking about job search, the more unproductive it becomes.

Have a life. Enjoy people around you. Do something else. Get charged up with mini projects (or Netflix). Be productive and strategic about job search. And be patient. Fortunately (and unfortunately), time (and the probability of luck) is an important factor for your success.


Question For You

Have you found your answer(s) to “What’s the point?”


I found mine about writing. I fell in love with the process of writing, not the outcome of getting somewhere. Writing offers a wonderful space to spread out ideas, develop them, connect the dots, and find innovative expressions. And I love it precisely because I’m not very good at it yet. There are always better ways to do things. And the good thing is that I am on the journey.


What’s the Use?
A little poem by Anonymous

What’s the use of a tear?
Who’ll buy it, night?
What’s the use of a sigh?
No one in sight.

What’s the use of a heart?
What’s the use of a name?
Who’ll carry the care?
What’s the use of a dream?


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This ONE: What’s the point? The leadership grill, unstuck from tech roles, and job searching in a bad market


Pass issues:

Issue #1 On Fulfilling career potential, How to be more assertive, and the powerful way to manage difficult conversations



p.s. I am speaking at the following webinar,

Fireside Chat with Nandini Joshi, COO, StashAway

Is it just me or do you also feel clueless about making a career change? Tickets, Thu 28 Mar 2024 at 7:00 PM | Eventbrite.



portrait_Yolanda Yu_YL_r

Empowering Change From Within

Career & Leadership Coach, Start-up Mentor, and two-time Penguin Author, Yolanda has over 20 years’ corporate experience and served leadership positions in world top technology companies such as Alibaba, Visa, and Mastercard.

From software engineer to sales, headhunter, entrepreneur, to business leader in eCommerce and Fintech industries, Yolanda reinvented her career for countless times. She specializes in tailored coaching programs for professionals in the phases of career change and leadership transition.

Yolanda is particularly passionate about equipping technical leaders with leadership skills. She delivers leadership 101 courses through group coaching and 1:1 engagement.