Think of it like this: If you want to help someone, you don’t start by guessing their age, job, or hobbies. You start by asking, “What are they struggling with?”

Photo by Ben McLeod on Unsplash
As a kid, do you recall being asked, “What do you want to be when you grow up?”
What was your answer? Did you say you wanted to be a fireman? Or a nurse?
I’m always intrigued by the answers I get from children who are often emphatically sure about their future career choices. Quite often, their answers come from their limited exposure to career options as introduced by their teachers.

My 7-year-old daughter regularly showers me with her ambitious plans whenever she encounters a new career she is fascinated with. On one occasion, she excitedly claimed she wanted to be a clown! Surprisingly to me, her simple reasoning behind this choice was that she wanted to bring happiness to others.
Based on many of these interactions, I’m led to think children choose their ideal occupation not because it will bring the highest salary or status recognition, but rather based on what they enjoy doing. And quite often, they do not feel tied to one choice, especially when the child in question has multiple interests.
My kid’s nimble career hopping got me thinking about how we choose — or don’t choose — the jobs we find ourselves in, and what, if anything, we can do to secure our careers as we face these uncertain times.
“Oh, how cute, but you can’t be a violin maker and a psychologist. You have to choose.” — Emily Wapnick
According to Emily Wapnick in her TED talk, not all of us have one true calling. In fact, some of us have multiple interests and creative pursuits, which she terms “multipotentialite.”
In today’s job industry framework, many of us are an outcome of the linear, factory system of education, where we choose a career path to focus on once we reach a career-choosing age. Then we spend 3 to 4 years studying in a formal school setting in the hope that with the right certification, the career we decided to pursue will be a rewarding one.

Photo by Matese Fields on Unsplash
But what of those people whose current job is not the one they received formal education for? How do they make that switch?
The urge to make a career change looms large in one’s late 20s when many face a quarter-life crisis where they experience a period of negative thoughts and feelings. It’s a time when conflicting emotional needs and personal passions now confront the initial reason for choosing a certain career path (i.e., job security, financial stability).
I have a client who has run a social enterprise for wildlife rescue. He mentioned that in recent years, when attending University career fairs, he has seen a decline in students seeking jobs in the finance sector and an increasing number who show an interest in becoming wildlife rescue officers, despite a marginal salary. “When given the opportunity, people want to explore more,” he explained.
As opposed to being an expert in just one thing (I-shaped), the term ‘T-shaped people’ became popular in the 90s when Tim Brown, from IDEO design consultancy, endorsed this approach to résumé assessment.
People with T-shaped skills are those who are experts in one thing but also somewhat capable in many other areas as well. The value of T-shaped people is shown in this video of the IDEO shopping cart problem, where a diverse group with varied skills solve a design problem, highlighting the importance of expertise from a range of fields and capitalising on a cumulative breadth of knowledge in order to move forward.

I believe this means of assessment has gradually caught on. And many hiring managers are starting to accept that individuals can have multiple specialised skills — which can lead to long-term success. We can be masters of some vs. masters of one.
If you are facing the idea that the current skill you have mastered might become less relevant in the days ahead, mastering more skills is one way to future-proof your career.
But what would that look like on a practical level?
If you want to be a master of some skills (vs. one skill), how many skills is it even possible to master in one person’s lifetime?

Using the 10,000-hour rule popularised by Malcolm Gladwell in his book Outliers, you would need around 5 years at a full-time job to achieve a level of mastery, provided you are spending 7 hours daily at that job, and those hours are spent focusing on perfecting the skill.
Put this way, the amount of time needed for mastery can seem painfully challenging, especially if you are trying to orchestrate a career change while picking up the new skill. Attending a one-day intense workshop or taking a 3-month course might seem futile in comparison to what is really needed.
Is there a better way? Or at least, a different way to approach the idea of mastering new skills?
Is there a way to compress 10,000 hours of learning into a few months, or even days, so that we learn faster? Josh Kaufma answers this question in his video where he states that you only need 20 hours to learn anything — and you can do it in just 4 easy steps.
Kaufma’s approach to learning anything in 20 hours is as follows:
1. Deconstruct the skill. Decide exactly want you want to do with the skill and then break the skill down, practicing the most important aspects.
2. Learn enough to correct yourself. Practice just enough to notice when you make mistakes and get on the right path.
3. Remove the distractions. Disable notifications and remove all distracting elements.
4. Practice for at least 20 hours. Do 20 hours of deliberate practice. Stick with it no matter what.
Why focus on 20 hours of deliberate practice? Based on the learning curve theory, you can reach a basic level of proficiency within just 20 hours. If you divide the 20 hours into daily chunks of time, that’s just 45 minutes of practise every day for 1 month. (A vast difference from 10,000 hours!)
Some may argue that 20 hours would only provide a basic level of proficiency, and this 20-hours-to-proficiency concept can only be applied to certain skills at a smaller scale, therefore, it wouldn’t lead to any career progression. However, in the book Micromastery by Robert Twigger, there’s an interesting notion about mastering small skills. Twigger states, “A micromastery is a self-contained unit of doing, complete in itself but connected to a greater field.”
What is intriguing about this idea is that an initial foray can lead to greater heights. For example, a simple start with learning and mastering 4 basic chords could lead to playing hundreds of songs later on. Or learning 59 ways of cooking an egg — through transfer of learning and methodology — you could be able to cook potatoes in 59 ways!

Initial foray can lead to greater heights — Photo by Lucas Benjamin on Unsplash
In computer games, you might have come across a skill tree, such as those in Diablo II, World of Warcraft and other role-playing games. What is a skill tree? In the context of computer games, a skill tree is a hierarchical visual representation of skills that show how characters can progress by assigning points to individual skills. Reaching certain skills enables the player to pick up related skills. This allows the player to create a character that grows with the game story.

Diablo II’s Skill Tree — Screenshot from Diablo II’s Game
What is intriguing here is that through mastering a small number of skills you can create a unique game persona that will help you to solve problems within the game play. In real life, this can be likened to the skills that define the direction of our careers. Additionally, keep in mind that a graphic designer in the print industry would have the same core abilities as a web designer, but there are smaller pieces that diverge that make it relevant to the job requirement.

Example of Customer Support Skills Tree
In the game, the skill trees are usually predefined, so that you know what you need to learn to achieve a certain role. But in the real world, where should you start your learning journey?

Matthew Might is a computer scientist, biologist, and the director of the Hugh Kaul Precision Medicine Institute at the University of Alabama Birmingham. In an illustrated article, Might explains to future Ph.D. students the meaning of attaining a Ph.D. Initially, he describes it as the quest to push our knowledge boundaries, inch by inch.

However, it was when his son fell sick that he began his quest to identify his son’s rare and fatal genetic disorder.

Photo from Matthew Might
“One small dent in the circle of knowledge; one giant leap for my son.” — Matt Might
The goal of life-long learning is to constantly search for answers so that we can make sense of our world. Consider how NASA sends out exploratory missions to find new stars and solar systems to satisfy our curiosity, while also whetting our appetite for more.
In Simon Sinek’s book, The Infinite Game, we learn that Andre Agassi became depressed after achieving the goal of ‘Greatest Tennis Player of All Time,’ which he had spent his whole life trying to achieve. But you don’t have to look at your career as a linear journey to reach only one goal. Instead, you can reframe it as a life-long learning journey to attain an infinite goal. To reach that goal, you can try all means to achieve it and not constrain yourself in one silo.
You do not need to have a hypothesis or even a detailed map of your learning journey. Rather, the primary requisite is a curious mind to learn and to glimpse the greater possibilities out there.

You do not need to have a hypothesis or even a detailed map of your learning journey. Photo from Scop.io
“The future of work consists of learning a living.” — Marshall McLuhan
So, should you be a Jack of all trades? Or a master of one? Or perhaps a master of some?
Did you know the saying “Jack of all trades and master of none” has evolved over time? Here is a general timeline of its evolution.
1618: Jack-of-all-trades
1721: Jack of all trades, and it would seem, Good at none
1732: Jack of all Trades is of no Trade
1741: Jack of all trades, and in truth, master of none
1785: A Jack of all trades, but master of none
1930: A Jack of all trades and a master of one
2007: Jack of all trades, master of none, though often time better than master of one
2015: Jack of all trades, master of some
Over the years, this saying adapted to the perceived needs of the job industry for each time period.
In 2020, in this year of uncertainty and change, where we have to learn, unlearn, and relearn new skills to adapt to the new normal — it can be challenging to know with any certainty what jobs will soon become irrelevant or require re-invention.
Asking “What do you want to be?” may not serve a purposeful meaning in directing your learning journey because uncertainty clouds the kinds of jobs that will be available in the future.
However, rephrasing “What do you want to be?” to “What problem do you want to solve?” can help give us better guidance as we adapt to these uncertain times and as we explore mastery of different skills to pursue an infinite purpose.
For example, if you want to be a better chef, you could explore how to solve the problem of creating better food experiences for your customer, which may lead you to find an answer that lies beyond your knowledge of culinary and towards solutions found in science, 3D printing, or cellular agriculture.
What will Jack be in the future of work?
There is no definite answer, but I am pretty sure that a Jack of all trades and micromaster of some will adapt better than a master of one.

“When I left you, I was but the learner. Now I am the master.” — Darth Vader. Photo from Scop.io