How to Switch Careers — The Ultimate Guide

“No man ever steps into the same river twice.”

This post is for anyone who’s ever wanted to switch careers but is scared. “Fintech is sooooo cool,” you might say. “But I don’t have any relevant experience. And I don’t know anyone in that industry. What could I possibly do?”

I’ll try to address the questions above, along with any doubts you might have that mid-career switches are possible. A lot of this post comes from personal experience. I’ve done a couple of diverse things (many unrelated to my degree) in my 11-year career: from working with a national oil company, to an American MNC, to a Malaysian social enterprise, and am currently smack in the middle of potentially the largest financial disruption of all time.

But I’ve also observed friends and colleagues who’ve made leaps of faith. I’ll bring up points which I learned from them, as well as good stuff I’ve picked up from books and the Internet.

Caveat: if you’re looking for an entrepreneurial success story, about someone who left his job to build a multi-million company — you won’t find it here. I’m not really an entrepreneur, and besides — there are plenty of those already. But this one is for the maybe 65% of people who work normal day jobs, but want to get to a better one.

I’m convinced that our job landscape will continue to evolve rapidly. Traditional jobs are gonna get less and less in the coming years, so maybe we’ll all be independent workers one day. But hopefully these points are universal enough to help us through the next great wave of change. I hope you find them helpful.


1. Understand Why It’s So Scary

First of all, let’s talk about why career moves are so scary…

Change, by nature is scary and uncomfortable. Because our human bodies are biologically programmed to look for comfort and security. Research shows that uncertainty makes us miserable.

But also, for most of us change (or the prospect of change) is scary because we’ve spent most of our lives according to “the plan.” Whats “the plan“? It’s the one that society — our parents, teachers and peers — preaches to us. If you have typical Asian parents: “Doctor, Engineer or Lawyer.”

In his recent magnificent article about careers, Tim Urban uses a great analogy: Most of us spend our early years following a predefined path. Like tadpoles down a river…

“We’re told the rules of the river and the way we should swim and what our goals should be… “

Hence, many of us never develop the skills to become “CEOs of our own lives.” We’re not comfortable deciding our own paths. The easy alternative? Follow what someone else tells you to do.

For most of my early life — I was a great follower of the “tried and true” path too. But I think my breakthrough came when I read something and realized that everyone has power to shape their own careers. It also helped that I had a mentor; who pushed me to do more with my life, instead of following someone else’s plan.

It wasn’t easy, but if someone like me who pretty much grew up following “the plan” can break free and forge my own path — maybe you can too.

Here’s how.


2. Work the Feedback Loop

The feedback loop is one of humanity’s basic survival tools. You probably use it all the time without thinking. For example, remember the first time you got punished in school? If we broke it down in slow-motion-HD replay, maybe it went something like this:

  1. Initial state: The classroom is quiet. Both you and Nora are happily minding your own business.
  2. Action: For some weird reason, you think it’s a good idea to give Nora’s ponytail a sharp pull.
  3. Feedback: Nora falls down and starts crying. The classroom descends into chaos. The teacher comes up to you with a thick ruler…

And that’s the story of how you learned not to pull little girls’ hair in class.

Hopefully you learned your lesson. But what has any of this got to do with switching careers?

Well, it turns out the feedback loop is how you find the answers to all your tough “life questions” — including your career ones.


Feedback Loops for Your Life

Because unlike school, there are no black and white answers for life’s difficult questions. Instead, you usually have to figure it out using a trial and error process:

  1. Initial state: Look at your current situation
  2. Action: Try something new
  3. Feedback: Evaluate how the new things affect you

The idea is that you’re never a “finished product.” You’re constantly improving. Sure, you have some core values — but everything else in your life is constantly being tried and tested.

Don’t like the way your colleagues treat you? Can’t understand why you never get good increments? Feel that your job is meaningless? Whatever your situation is, work the feedback loop: Change something, give it some time, and see what happens. Repeat until you get better results.

Now I know this sounds like a hell lot of work. “I’m already so exhausted, and now you want me to start testing every part of my life?!”

But it’s the difference being a teachable person who’s able to switch careers, and a closed-minded oldie who’s stuck.

Because we have so much going on in our daily lives, we often lose track of where we’re headed. And I can’t tell you how many times I’ve met people who keep complaining about their jobs, yet never make any changes.

Unless we constantly evaluate our lives, and try new things — we will never make progress.


Woman thinking at work
Nora: “Why did he pull my hair all those years ago?”


3. “But I Don’t Have the Correct Degree…”

So you’ve decided you wanna start taking control of your career. You’ve examined your current situation, and are excited to try something new…

But then, the “comfort and security” part of your brain starts coming up with reasons why you’ll fail… The first being: “I’m not qualified!”

To that, I offer two rebuttals.  The first: for most people — your paper qualification is just your entrance ticket to the game of careers. After that, it’s your work experience and track record that matters.

(The exception here is for really technical things or highly-regulated industries. Like, you’d probably want a brain surgeon to go through years of certified medical training before opening your skull.)

In the case of other highly-regulated industries though — they’re starting to be disrupted too. People are finding faster, better, cheaper ways of doing things — that don’t necessarily need years and years of exams. (Ever wondered if the people who put those requirements in place actually do it to keep the market artificially scarce, and ensure they stay in power?)

Cracks are appearing everywhere in the wall of “you can’t get in because you don’t have the papers.” This is good for you and me. This is opportunity; this is democracy.


What Does “Qualified” Even Mean?

My second rebuttal about “not qualified” is this: no one’s ever really qualified for anything. In another of life’s most-ironic mindf*cks, the most qualified people always feel that they’re not (a.k.a. impostor syndrome). On the contrary, you should be worried if you constantly feel like you’re better than everyone else. You’re not.

Anyway, let’s say you want to work in Sales for your dream company. Which of the fictional two people below do you think your future employers would like more?

a. Bob has a PhD in “Sales and Marketing” but no experience
b. Mariah “only” has a diploma, but was the number #1 salesperson in her current company for 2017.

I’m guessing you agree with me that Mariah gets the call first. But it’s not just you and me making that logical decision. More and more companies are joining the chorus that degrees aren’t a requirement to hire any more.

The real-life Tony Stark of our time, Elon Musk says so too: “Skills matter more than degrees.”

It’s not that degrees or paper qualifications are useless. But they shouldn’t be a barrier between you and the job you want.


4. Find Relevance in Experience

“That’s great,” you say. “I always hated studying anyways. But what if my experience is in a totally different field? What if I’m actually an expert in geophysics, but am now looking to join a food-delivery business? Help!”

This is where we delve into the art of connecting the dots.

Perhaps most popularized by appearing in a Steve Jobs speech — “connecting the dots” means looking back at how things in the past have helped you become who you are today. Let’s think about a familiar example:

Apple still produces some of the most beautiful tech products in the world. Ever wondered how Apple mastered this, while most of the tech world continues to struggle with ugly?

Well, one of the reasons is Apple co-founder Steve Jobs was greatly inspired by a calligraphy class he took in college. You’d never imagine that such an abstract (most parents would call it “useless”) course would be valuable to a tech entrepreneur. Steve Jobs never thought it would be useful either, but it was. And the world is better for it.


Connecting Your Own Dots

Of course, some work experience will be more relevant than others. Say, you’ve been a practicing engineer for a decade — it’s not hard to see you apply that experience as a lecturer. But if you’re a restaurant manager, and wanna jump to a tech startup — those branches of knowledge aren’t as close.

You can still find overlaps though. Ask yourself: what valuable things have you learned before that will help you in your new career?

Going back to our restaurant manager example: maybe you don’t know how to code. But as an F&B person — you probably know how to deliver excellent customer service. This is very useful.

Remember, some skills are valuable across all industries. For example, people management will always be required in any job that deals with people. Problem-solving skills will always be valuable anywhere. And my personal favorite: critical thinking will always be necessary, so you make wise decisions.

No knowledge is ever wasted, if you learn to apply it to whatever you’re doing. The tree of knowledge might have many branches — but they all link back to the same roots.

Now you just need to convince someone to let you prove it.


5. Prepare for Your Target

“Library is free.
Websites are free.
Podcasts are free.
Wifi can be free.
Content is free.

Your reasons for not learning?
All bullshit.”

How do you convince someone to give you a chance, when you have no experience in your target field? To me, the answer is simple: it’s intense preparation. The more difficult the jump, the more intense the preparation.

BTW, I still don’t understand how people sometimes show up at job interviews without doing detailed research about the company/industry they’re applying for. It’s crazy. And yet, I see it happen all the time.

Maybe most people feel that basic preparation is enough to get you the job of your dreams (re-read that sentence again — sounds silly doesn’t it?) Well this is actually a good thing for you. Because you’re gonna be somewhere in the middle between basic preparation and stalker-level preparation, you’re gonna stand out from all the other applicants.

So how do you stalker-level prepare for a job that you want? This isn’t an exhaustive list — but I can think of some things:

  • Take Coursera/Udemy/Khan Academy (free!) courses on the industry you’re targeting.
  • If you already have a company in mind, read every page of the company website. Especially the Vision/Values portion.
  • Read the first 3 pages of Google News for the top keywords being thrown around in the industry. For example, if it’s Blockchain you’re interested in, your top few keywords might be: Bitcoin, Ethereum, Blockchain, Digital Currencies, and Distributed Ledger.
  • Follow the top 10 CEOs of the top 10 companies in the industry on LinkedIn/Twitter and see what they’re all talking about. (Wasn’t kidding when I said “stalker.”)
  • Reach out to your network. Talk to friends who are either in the industry/know people who are in the industry (more on this later).
  • Prepare a presentation summarizing all your findings. Practice presenting to a friend.
  • Use the feedback loop (Point 2) to continuously add to your knowledge in this field.

(For some real next-level shit, check out this legend who wanted to work for Amazon — so he created his resume in the style of an Amazon web page. He received over 100 job offers.)

Okay, maybe I’m biased towards doing huge amounts of preparation work because I’m a geek at heart. I acknowledge it’s not the fastest or easiest way. Some might even say that it’s better to just understand the basics, and then use connections (and bullshit) to get the job.

But I also think that when you’re new to something — you’ve gotta put in the work. If it were so easy, everybody would have done it right?


Soldiers skydiving out of plane
Remember, the more difficult the jump, the greater the preparation


6. Understand the Winds of Change of Industries

“A rising tide lifts all boats.”

This portion is for those of you who are confused why some of your friends get three promotions in three years and have titles like “General Manager.” Meanwhile, you’re still an “executive” buying Starbucks for your seniors every morning.

Not to take anything away from how capable your friends are, but here’s a big factor: Right Place, Right Time.

The world is always changing. Certain parts of the economy go up and down in cycles. And as you guessed — the jobs that come along with it.

Old industries fade away, while new ones are created and take their place at the forefront. You’ve probably already heard buzz words being thrown around like “Industrial Revolution 4.0.” But what does this mean for the average worker?

It means this: Change is coming; so what the older generation taught you about work may not be true any more. And if you want huge leaps in salary/opportunities/learning, booming industries are the way to go.

(It’s also easier to jump into a booming industry with less experience, because they’re always short of talent.)

Let me qualify this a little, before anyone says I’m a heartless mercenary. I’m not saying that everyone should ditch traditional industries and jump into risky startups. What I’m saying is that for the average worker, the industry they’re in plays a huge role in their personal situation.

For example, we’ve all heard the term “hungry musician.” Everyone loves music and there are lots of musically-talented people. But the reality is unless you’re an outlier like Taylor Swift — it’s hard to make good, consistent money from music. And it takes a hell lot of hard work. Contrast that to a lucrative industry like Oil & Gas.

I can guarantee you that an average slacker in Oil & Gas (don’t let anyone fool you that there are no slackers in highly-paid industries — there are slackers everywhere) makes a lot more money than an average slacker in music. Don’t be a slacker. (But if you’re one, be a slacker in a highly-paid industry.)


So Which Industry Should I Go for?

Well, knowing how “qualifications” are becoming less of a barrier today, where do you want your career to go? What’s your dream job?

“I don’t know Aaron. This is so confusing. Why don’t you just f*cking tell me where I should go if I wanna make a ton of money?”

Well, I can’t tell you what to do, but I can share my stories. Personally, I recently uprooted myself from social enterprise work and dived into the digital currency (cryptocurrency) space. Because I think this industry will grow like crazy. It’s not really about money though. Instead, I wanted the learning, growth, and opportunity to be a pioneer. It’s the right choice for me; right now.

But I can’t say it’ll be the same for you. My objective here isn’t to tell you which industry to choose. It’s to help you figure out for yourself.

Some resources might help:

There’s no simple answer — but the more preparation work you put in, the better your chances of making a good decision.

But also, remember the all-powerful feedback loop? Even if you give something a try, and it doesn’t work out for you — it’s okay. You just need to re-adjust.

Don’t be afraid of failure. Be afraid of being stagnant.


Singer holding guitar on stage
p.s. I once wanted to be a singer/musician too


7. Work Your Connections

“But wait,” you say. “I know better than your nerdy ways, Aaron. Instead of wasting all my time reading, I’m just gonna take a shortcut and ask a mentor!” Boom! #lifehack

And… I… 50% agree. I haven’t covered enough about working your connections yet — so let’s talk about it in a bit.

But firstly, I don’t know a single successful person who doesn’t read a lot. (Just for fun, I Googled “Successful people who don’t read a lot.” You know what came up? Donald Trump.)

Secondly, I’m assuming your mentor is a successful person. Well, successful people usually don’t like lazy people who ask lots of basic questions without doing their own research first. It shows disrespect.

Instead, to make full use of your mentor’s time — ask for guidance after you’ve already done the work and still can’t figure something out. Not something that anyone can Google easily. That brings a lot more value to both you and your mentor.

“Huh? I’m supposed to bring value to my mentor? Isn’t he/she supposed to be the one teaching me?”

Yes, mentorship is a two-way street. But also, you’re supposed to bring value to everyone you interact with. That’s how you become well-connected.


How to Find Mentors

“What if I’m just a young person who doesn’t know anyone? How do I even get a mentor, and why would they want to help me?”

Well first of all, a “mentor” isn’t necessarily someone you meet once a week to drink cappuccino and share breakup stories. It would be great if you had someone like this — but mentorship can take other forms.

For example, we’ve already talked a lot about reading. It’s a miracle really — someone successful put down all their life lessons into a book, and we get to soak it up for cheap. But if you’re less text-inclined, there are also tons of websites and podcasts and videos to learn from. What a privileged time we live in!

Let’s take it one step further though. Let’s say you want a direct response from someone. Well, in today’s day and age it’s not that hard to reach out to anyone via the Internet anymore. With a little bit of “stalking” (which you’re already good at right?), you’d be able to at least get connected to some people within the industry you’re targeting.

(p.s. Here’s the best article I’ve ever read about cold emailing. For when you wanna get connected to someone important.)

But first, you have to understand that they’re busy


How to Talk to Busy People

Ever felt that the more rich and successful a person becomes, the more he/she behaves like an asshole? Like…

“Tony’s an asshole. He can’t even reply my email when it would only take him five minutes.”

Well, the problem is, important people have huge numbers of people wanting “five minutes” of their time every day. Now, this might be hard to imagine, especially when you’re young and carefree. But for people who’ve figured life out, time is truly their most precious resource.

And as much as they’d like to be nice — sometimes they really can’t afford that five minutes.

How do we get around this? It comes down to two things:

  • Answer the question: “Why should this person help me? What’s in it for them?”
  • Make your request short, and easy to say YES to.

So let’s say you wanna ask Tan Sri Tony Fernandes out for coffee. Take a minute to imagine yourself in his shoes… Would he be excited if all you can offer is the opportunity to take selfies and talk about your fave travel destination? I know you’re pretty — but everybody else offers that too.

But let’s say you have an idea that can help him make millions. And you’ve actually done some testing work on it already. Your chances are a lot higher now.

That’s an extreme example. Of course, you don’t have to aim for someone like Tony. Maybe you want a career in consulting, and your friend’s friend works for PWC. He might be willing to advise you just because he’s a nice guy who likes helping younger people.

But do you really need him to leave work, fight through traffic, and endure horrible coffee in an overpriced cafe — to chat with you for an hour? What if you could put your questions in a simple email so he can reply at his own pace? Or if you could just schedule a quick 10-minute phone call? Remember, show ultimate respect for the other person’s time. Make it easy for them to say “Yes.”

Above all, don’t be that person who only talks to people when he/she needs help. Instead, be that person who always tries to think for others.


Businessman in chair explaining something
Bring value to every relationship, even if it’s with someone much older and wiser


8. Consider the Cost

Remember the classic quote?

“The grass is always greener on the other side.”

Because we’re human beings, all of us have a tendency to look at other people’s careers and get jealous. So I think it’s important to remind everyone here that switching careers isn’t a bed of roses. There are costs, and the costs are often steep.

Research has shown that switching jobs is the key to earning a higher salary faster. But understand that when it comes to big career shifts, you might have to take a pay cut instead. I did — and four years later, I still haven’t made it back to my salary during my Oil & Gas days.

Also, when you change careers, it’s not just your salary or morning commute that changes. Because our lives are so interwoven with our careers, almost everything — including the way you look at yourself, and the way others look at you — will change too.

There are other less-obvious things to consider. Like seniority. It often takes years to build a reputation within an industry.  And once you’ve developed influence and respect, it becomes easier to get things done. People are more willing to open their doors to you.

Would you be willing to give that up, to try something new? Where you’ll be coming in fresh and have to build up your reputation again?

I’ve made three career shifts in my life now. And while I absolutely have no regrets, I can also tell you that it’s jarring to the system. Uprooting yourself and having to settle into a new environment can get tiring. And I can’t tell you the number of times I’ve had to eat humble pie. But that’s just the way life is — when you’re new to something, you’re gonna get humbled a lot.

I mean, if you’re the type of person who likes blowing things up and starting again — it’s great. But most of us aren’t.

Not to mention, it sometimes feels really scary.


9. Find Your Courage

How do you find courage to do the hardest things in life?

Because you could prepare for your next career move by drowning in articles about  “the next industrial revolution” and endless networking sessions with mentors. But unless you make a move, it’s all just mental masturbation.

Well, to me the secret isn’t to attend “Absolute Power” seminars, or even to read a hundred motivational books. The secret is in taking micro-steps:

Do things in your life that are outside your comfort zone. That scare you a little — but not so much that you’re paralyzed with fear. For example, most people are scared to death of public speaking. The way to conquer this isn’t to volunteer to be MC for a 1,000-pax Annual General Meeting. For most people, that’s too much; too soon.

Instead, start small: give a three-minute talk to two of your close friends. Then five; ten; and then maybe join a local Toastmasters.

The all-powerful feedback loop (from part 2) will kick in and tell you: “Hey this isn’t so bad, next time we can try something scary again. Maybe something even scarier.”

We’re talking all about careers here, but micro-steps can help you in every area of life. Because when you gain confidence in one area, it helps you in other areas too.

For me, the courage to switch careers multiple times didn’t come from any single moment of enlightenment, or some fancy leadership summit. It all started when I was a young teenager, frightened to say “Hi!” to the girl I had a crush on. Well I forced myself to, and it didn’t turn out so bad. I haven’t stopped trying small, scary things ever since.

Courage to make one big step comes from confidence gained through a hundred small wins.


Staircase under open skies
The stairway to heaven begins with one small step


10. Stay in Touch

You made it — you pushed through the fear, the obstacles and now find yourself on the other side — embarking on a new career. It’s gonna be exciting, but there’s one last thing:

Remember to remember the people you left behind.

Studies have shown that the No. 1 predictor of career success is being in a large, open network. Or simply, the more you’re exposed to new ideas — from different people, from a wide range of backgrounds — the better your chances for money, promotions, and recognition.

It makes sense when you think about it. The more contacts you have, the more influential you are. You can get things done. But also, being exposed to new ideas means your personal tree of knowledge is constantly growing. You’re more creative, and can bring more value to people. Plus you’ll be a hell lot more interesting to talk to than someone who only sticks within his/her group.

Not only is meeting exes (colleagues, I mean) fun, it’s also good for your career success.

So don’t make the mistake of losing touch with them. At the very least, keep the relationship warm with just a few ex-colleagues. Remember: relationships take effort. Because the constraints of modern-day living will make it easy to miss gatherings, stop replying messages, and eventually be forgotten.

And without conscious effort, you will.


– – –


We’ve covered a lot, from feedback loops to mentors to finding courage. But if there’s one final thought I can leave with you, it’s the same one that came to me a decade ago — when I was still firmly along “the path.” It was a good path; one that people still ask me about all the time: “Why did you leave?”

But I wanted to create my own. And even though it’s often hard, it’s this same thought that has carried me through the past decade:

Each of us has the power to change our lives.

We may not always get exactly what we want, when we want it — because life isn’t fantasy, and there’ll always be challenges. But we all have a choice. And in whatever area of your life you wish to change — whether it be money, love, politics or career — may you exercise that choice well.

The winds of life will always push us around. But will you push back?


– – –


This is by far the longest article I’ve ever written. Could I suggest that you bookmark it, and come back to re-read certain portions when you need them?

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  • Thank you Mr. Stingy for the kind article. I believed you forked out huge amount of time to get this blog lays out beautifully and convey the message.
    I read every word, and agree with you at every points. THANK YOU.

    Can I get permission from you, to quote a few lines in your article in my next YouTube video? I am doing topics unravelling the hidden truth/dark sides of travel and solo backpacking, overcoming fears and comfort zone is one of the issue that I want to talk about.

  • Thank you for this – definitely the advice I needed to read at this early stage of my career and I’ll certainly be returning to parts of it again. Stumbled upon your blog a few days ago and it’s been so comforting to read the experiences of someone who went through what I’m going through now. I appreciate your writing so much and am excited to see more of what you’ll post in the future!

    • Thanks so much Elena. Really appreciate your kind words. Please let me know if there’s anything I can write in future that will be helpful. All the best!

  • I guess one great piece that connects it all but it may appear to be the most abstract factor is what we called “Patience” or in a long winded way, it can be named as “Fighting against the needing for instant gratification/reward to prove the steps taken are correct and not wasting time/effort”. Probably the effective method to counter this is to back to the first suggestion, which is to truly understand uncertainty is inevitable.

    Another contradictory thought will be before planning for career move, might consider want to take a step back to comprehensively assess is there any opportunities that could be leverage before making that decision. There could a possibility where the root cause can be an individual not being exposed long enough or appropriately to entasked with work that could provide job satisfaction (certainly the circumstances has to be considered when such assessment is done)

  • Really enjoyed this article and it brings to light so many things that one would need to consider when switching job. Thank you for the wonderful read, Aaron! 🙂

  • To add, I made a job shift 8 months ago and I’m learning way faster than before to catch up.
    Nature of the job is similar but totally different industry and wider exposure.
    I’m very satisfied (although there are plenty of hard work), life would never be the same.
    I care less about salary (I could be earning less than their industry standard) but get lots of satisfaction from the job, and I believe hard work pays off.

    • So good to hear that you’re satisfied and also learning lots of stuff. You’re in a great position!

  • Wow
    You got so many links to the good job site and reference, industry and wind of change.
    I went to many free webinars and although the free ones usually try to sell product, sometimes they does give out one or two important clue about the future.
    It’s very true to say podcast is free, content is free, reason for not learning is bullshit.
    Thanks for another great article Aaron!

  • Read every word. (after a few hours with breaks in between)

    Thanks for sharing Aaron!

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