Hello Reader,

Al here.

Next week is my birthday, so for that totally unrelated reason, before I send out the usual "study efficiently" schtick, I decided to let out something different. ;)

I've been wanting to write about career change a couple of times now, but never had the courage to do so — I don't even know why.

So here it is...hopefully this helps at least 1 person.

Maybe that's you, maybe not.

But maybe this could spark your thinking in one way or another. I feel like it's too valuable not to share.

Enjoy!

I’ve changed careers four times, and I’m not even 30 yet.

Engineering → Grad school (quit) → Online Marketing (a few blogs) → Dental clinic marketer → E-commerce → Back to being a learning coach + dental clinic.

Each transition was messy. Some people called me indecisive. Others said I was wasting my potential.

But every single career change taught me something that compounds. And those lessons from “failing” at different things were actually worth MORE than any single successful career path could’ve given me.

Let me share what actually happened...

Lesson 1: Get brutally clear on the life you want (not the career)

Growing up in the Philippines, I watched my family struggle with something that wasn’t just money — it was time.

My parents would leave before I woke up and come home exhausted after 4- to 5-hour commutes through rush hour traffic. Family dinners were rare. Weekends were for recovering from the week, not for being together.

I remember thinking: When I start my own family, I want something completely different.

So while everyone was asking “What career do you want?” I was asking myself a different question:

I wrote it down:

• Wake up without an alarm
• Work that uses my brain, not just my time
• No soul-crushing commutes that waste half of my life that I could've used somewhere else
• Actually see my family and spend unplanned time
• Financial freedom without selling my soul to get it

Then I worked backward from there.

During my research (aka YouTube), I came across a book on passive income. It was the best $3 I’ve ever spent — it opened the world of freedom through the internet.

This was 2017, and remote work was still weird.

I learned that there are actually a plethora of ways to build income online, most of which were earning based on my KNOWLEDGE, not time. And most of which take advantage of compound effects.

I was too shy for YouTube (everyone was doing video then), and my English wasn’t perfect. But writing? Writing was just thinking on paper. And I could think for hours.

So I took out my first $100 loan from my dad and started a few websites.

Writing was a pretty basic thing for me back then, and knowing that I could actually earn while doing what I loved most...man, that was genuine fulfillment.

Then, after 1.5 years of figuring things out — BAM! I finally earned my first $7.

Eventually, I reached a point where what I was doing was aligned with my goals, and was earning $500 in a month with only my ideas doing the work. So technically, I was living a “financially free” life because I had zero responsibilities.

But really, I just struggled to earn real income.

It came to a point that LeanAnki wasn’t serving me financially anymore. I wanted to move out to move on with my life. I had the passion, but passion wasn’t enough to pay the bills. I felt stuck.

I needed to find other income sources.

So I reached out to a friend and got into e-commerce.

Which brings us to lesson two…that I learned the hard way.

Lesson 2: Alignment matters more than advancement

After getting into e-commerce, I built a dropshipping business with 10+ people. Some were partners, some were employees. Money was flowing. From the outside, I’d “made it.”

$1m/year business! Buy a sports car! Fancy clothes!

But the truth is I was miserable.

I was earning a lot, but was living paycheck to paycheck since I had to pay all of these people and business expenses to pay.

And the root problem is the business model itself — dropshipping random products — which created zero real value. We were just middlemen making quick margins. No real impact, no real purpose.

With the mental models I’d developed, I could see exactly where this was heading. Building on a foundation of no value creation was OBVIOUSLY a recipe for eventual collapse.

So I left. Walked away from the money, the status, the “success.”

Went back to what actually aligned with who I am — teaching people how to learn better.

Lower income at first, but every skill transferred:

• Marketing knowledge from all those blogs and hundreds of e-commerce
• Systems thinking from engineering & business
• Research & learning skills from that brief grad school stint
• The deep understanding of learning that became my core offering

I realized something profound: You can change careers while still moving in the same direction. You’re just switching vehicles, not abandoning the journey.

Now, just because there are faster vehicles doesn't mean it's easy.

Much like a hermit crab trying to find a new shell, you are the MOST vulnerable when you are changing your vehicles.

Let me explain.

Lesson 3: Dark motivation as your fuel (to avoid comfort zones)

When I started to become serious about studying after barely passing all my subjects, friends told me: “You will fail anyway, so why study?”

When I ranked #1 in my mock boards and decided that I wanted to rank #1 in my boards, some relatives told me: “You just need to pass. Don’t aim too high but disappoint yourself in the end.”

When I finished at the top 6 and decided to join a paid grad school scholarship after: “You are wasting your opportunity for a high paying job!”

(...which was a freaking $400/month job — like $2/hour)

When I finally started earning online, my parents told me to “Get a real job. You’re throwing away your degree.”

All of these served as my dark motivation. They fueled me when I got too comfortable.

So whenever you feel like things are "okay" — they're actually not. It's NOT okay to be "just okay". That's like saying you're okay to "just know a few things" but when exam time comes you fully regret that you didn't prepare very well.

I don't care what anyone says: if an emotion feels "negative energy" to you, ACTUALLY FEEL that anger and the humiliation, and use that as fuel for your growth!

Now, this is just the baseline.

As with anything else, this should also have a "check and balance" type of motivation: Learning to LOVE what you do.

I know it sounds cheesy, but we're too "into science" that these holistic concepts of "love" and "hate" aren't even talked about:

You'll do anything for the things/people you love.

And if you think about it, you ALSO feel hate because people have wronged something/someone you love.

So yes, while I felt all of that resentment boiling within me, I also loved every second I spent learning! Because when you are a lifelong learner, everything is interesting. That’s what kept me going.

The doubters gave me fuel for the dark days. The love of learning gave me joy for the journey.

You need both.

So yes, I kinda threw away my degree. And every voice of doubt became another log on my fire.

But you can lean into that dark motivation without hurting anyone. Let the doubters fuel your drive. Let your passion permeate everything else.

Lesson 4: Moving out (even if it’s crazy)

The most transformative thing I’ve ever done:

Moving out just to prepare for board exams.

In the Philippines, it’s normal to live with your parents until you’re old. But I moved out temporarily with only 5 months to learn 5 years of engineering. I was ready to try whatever was possible to succeed.

Social life could wait. I was introverted anyways.

And my results exploded.

Same thing happened when I moved out (again) after 3 years.

Although I lost (and found) my soul in the process...

I know if I didn't make that bold decision, I would've been the same person today.

Now if moving out is NOT really an option, well, if you can find at least "5 voices" — through content, audiobooks, whatever — that align with your goals, and you always create personal quiet time to think, that’s already a huge step.

But if you can physically change your environment to match your ambitions? That investment pays for itself tenfold.

Lesson 5: You are your ultimate safety net

After quitting ecom, I lost my income overnight and went into serious debt. Hard decision, but I had to "tank" everything to move forward. The obstacle is the way.

Five years ago, that would’ve destroyed me. Back in 2021, I was diagnosed with depression and anxiety, so a crisis like this would’ve sent me spiraling.

But this time, I barely flinched.

All because I learned something that no "learning technique" could ever acquire: When things go to shit, there is no safety net except yourself.

When I entered grad school after topping the boards, everyone asked about my backup plan.

When I quit grad school for my online business, my parents kept saying it was unsafe and I should "get a real job".

When I left corporate e-commerce, they said I was insane to walk away from the money.

When I pivoted back to teaching, the questions got louder. I could even hear them in my own head.

Now, this sounds too good and "lucky", so let's just take a look at the real risk profile:

If I stayed on my path before, it was safe — there was a 100% chance to stay the same and earn $400 with 4 hour long commutes every single day.

If I made the risky decision, I had like a 10% chance of succeeding, but the payoff was having the life that I want sooner.

Besides, there was a 90% chance that I’d learn new skills and become even more valuable since my skills were a bit rare.

So in the end, the strategy kind of set me up for success.

When all else fails, all I need is one company to believe in me and my bets to get back to paying the bills.

I'm not saying all of these to brag.

My point is: Every time I bet on myself — even when I “failed” financially — I won in learning. And those learnings compounded.

When you bet on yourself, you either earn or you learn. Both are wins. Both make the next bet easier.

So your "personal safety net" actually consists both your personal development, and your skillset.

Taking responsibility for everything — even things that aren’t technically your fault — is what transforms you from victim to victor.

The mental models I built, the mindset shifts I developed, the skills I accumulated — nobody can take those away. They’re mine forever.

And they’re the only safety net that actually matters.

Phew. That was a mouthful. I only expected to spend just a few minutes here, but I made sure I actually got the experience on point.

Now, just to make things clear...

My goal here isn't to persuade you into changing your career — not at all!

In fact, if you were to take one point from this message, it's hopefully to create your own freedom through a lifelong commitment to learning and taking action.

Whether you're still in school, in your job, working on your business...

That loop has never been a losing game.

And it's not even for your grades or for a certification exam. It's for your own good.

The world isn't going to be more kind. And worst of all, do know that the world already has a default life plan for you if you don't choose for yourself — and it's not pretty.

You only have control over how you might respond, and learning a lot prepares you for all of that.

So learn a lot. Take action. Learn again.

To my younger self: you did great, and I'm endlessly grateful you chose this path. Now read a shitton of weirdly interesting books, apply everything you learn, then start writing!

Question for you...

Have you been thinking of changing careers? If yes, what's the biggest fear holding you back?

Genuinely curious.

To smarter studying,
Al Khan