Don't Ask What You Did Wrong — Ask What You Did Right: The Six WHY

"What did we do wrong?"

That's a question one of my students asked me. It's also the question my friends and I — 37, 38, almost thirty — keep throwing at each other when we get together. Career stalled, relationships stuck, health declining, bank balance flat. Everyone's lost.

I didn't answer right away. I asked back: what do you think you did right?

The student froze, gave an awkward laugh, then trailed off: "I guess… nothing."

I spent some time on this and put together 6 questions (The Six WHY) to audit my own choices over the past decade. This article isn't here to give you answers. It's a worksheet — you have to think through it yourself to find your own.

Here are the 6 questions:

What do you think you did right? Why?
Concretely, what did you do? Why?
What did you really want to do but didn't? Why?
What did you really want to do but missed? Why?
What should you have done but didn't? Why?
What shouldn't you have done but did? Why?

When you can confidently answer these questions, the answers to your bigger questions show up on their own.

Now I'll walk you through all six using my own life as the example. Start with the most important one.

Question 1: What did you do right?

If you can answer the first question, you don't need to answer the rest.

Because anyone who can answer Question 1 usually already knows what they did wrong.

I audited my major life decisions from the past decade. A few things I think I got right:

Came to Taiwan to study in 2011
Stayed in Taiwan for grad school and start working in 2014
Worked as a research assistant at National Chengchi University in 2018
Decided to marry my girlfriend in 2019
Started learning to invest in stocks in 2019
Started investing in crypto in 2022

Update (2026): This was written back in 2024. Two years on, looking back at the "what did I do right" list, things keep stacking —

2023: Took 3 months off, got married at the end of the year

2024: Daughter born, started writing a book, decided to do a PhD, started building personal brand business

2025: Busy with the kid, holding down work, kept building personal brand

Early 2026: Officially incorporated my company, getting the book ready, building a PM community

Result: I'm busier than ever. If I can swing it, I'd love to take all of 2027 off — these last three years have been brutal.

What I want you to take away: you won't know you got it right before deciding. You have to do it first, then find out later.

In 2011, after my restaurant startup in Malaysia failed, I followed friends to Taiwan to start university.

Because of that failure, I wasn't really in the mood for a normal college life. All I did was study.

Two years of that, my grades shot up, and I met a Filipino friend named Jeff who got me into the gym.

As my body and mind got healthier, I fell in love with Taiwan's pace, its everyday human warmth, the way information flowed.

In 2014, I told my parents I was staying in Taiwan for grad school and work.

In 2018, I joined National Chengchi University as a research assistant. That's where I got familiar with academic research — the foundation that later got me into the PhD program in the Science Education and Digital Learning division at the Graduate Institute of Applied Science and Technology, National Taiwan University of Science and Technology.

In 2019 I met my now-wife. We decided to marry not long after, and we're still very happy.

From 2019–2022 I learned to invest. It completely changed how I think about money. No big wins, but at least I survived a bear market, lol.

If you read all that, you should be feeling something:

You won't know you got it right before deciding. You have to do it first, then find out later.

Which means in the moment you don't actually know if you're right. But you have to trust yourself. Trust that your choice is the right one.

This is exactly what Steve Jobs meant by "connect the dots."

Three sentences, one principle:

Right or wrong is a verdict only hindsight can deliver — no one can guarantee it in the moment
Action matters more than correctness — if you don't act, there are no dots to connect later
Trust your own choices — not as a feel-good slogan, but as the prerequisite for connecting any dots

Question 2: Concretely, what did you do? Write down the 10 most memorable things

Audit the decisions and actions of the past few years. List them out — aim for 10.

If you're still in college, you can do this exercise too. Just shift the lens:

Courses you took: programming, game-based learning theory
Your capstone project: built an action game
Your internship: web design Company
Your physical/mental health: started taking supplement, started therapy
Skill development: studying copywriting
Friend circle changes: drifted from some people, met new ones
Diet habits: got into coffee, quit bread

Then next to each item, ask yourself "why" and write down the reason.

For example:

You picked game-based learning because you wanted to know how to embed knowledge into a game so players actually learn.
You interned because you wanted to learn web design at a company with a really cool website.
You met new friends because they're positive and proactive, and being around them pushes you to work harder.
You started lifting and running because your stamina was tanking and you needed to move more to feel healthy again.
You drifted from some circles because they'd become echo chambers.

If something doesn't have a strong "why" — or no real reason at all — flag it with an O.

Once you finish the audit, you'll usually get a WOW moment about everything you've actually done these past years.

Recommendation: do this one on paper.

Question 3: What did you really want to do but didn't?

Got things you regret not doing? I deeply regret not buying Bitcoin earlier!

Take some time. The things you wanted to do but didn't — write them down. 10 is enough.

Then like before, write the "why" — why didn't you do it.

I really wanted to go to Japan, didn't because I had no money
I really wanted to learn guitar, didn't because I had no time
I really wanted to study design, didn't because my parents wanted me in med school
I really wanted to make games, didn't because I didn't know how to start

Once you're done, I want you to say this out loud:

I didn't not do it. I just haven't done it yet!

Yes — you just haven't done it yet. Don't beat yourself up.

Now, on the right side of each item, write the "cost / condition."

Right — there's a price or condition you'd have to pay to make this happen.

Is the cost too high? Is the condition too hard? If it's too hard, are you still willing to grind it out?

I've spent a ton of time learning across a lot of fields. You could call me well-rounded (my own words, lol).

Even so, my career hasn't gone smoothly.

I wanted a freelance life, but my marketing and sales game isn't strong.

My side gigs and contract work aren't stable, so I never made the full jump to freelance.

I keep trying. Still trying. That's a cost — the cost might be a career that never quite takes off.

But "willing to pay" is at least a choice you get to make. The scarier kind: things where it's not about willingness anymore, it's about having missed the window entirely.

Question 4: What did you really want to do but missed?

Some things are never too late to start. Other things — once you miss them, they're gone. Like the Bitcoin price.

Hope you're not sick of me using crypto as the example, but I genuinely can't find anything that beats Bitcoin.

Something I've started noticing recently: I've barely spent any time on my own family.

When you're young you can run on adrenaline and grind for your career. Even if it doesn't work out, life can still feel intense and worth it.

But seeing my parents getting old — that shook me.

Some things, once you miss them, are missed for good. I've been grinding in Taiwan for years and barely stayed in touch with home.

Getting married made it even clearer: I can't keep being the wandering ronin I used to be.

Write down at least 5 things you really wanted to do but missed — things you may never be able to do again.

At minimum, they become signposts. They show you the road ahead and clarify your choices.

There are lots of reasons things get missed. The reasons aren't the point. The point is: why do these missed things matter?

The "why" here is: why do these missed things matter to you?

Question 5: What should you have done but didn't?

If you've made it through the previous questions, we're close to the end!

The keyword here is "should." What counts as should and what doesn't — that's your call to make.

If you think you should do something but you didn't, there's an internal contradiction sitting in there.

Should we have studied harder? Did we?

Should we have saved more and spent less?

Recommended: write down 5, with the "why" you didn't.

Then ask yourself: do the things you "should" do conflict with the things you "want" to do?

For example: you should study hard, but you don't actually like the major — your parents pushed you into it.

If that's the situation, flag it with an O.

Question 6: What shouldn't you have done but did?

Save this one for late-night reflection. You don't need to write it out.

Sometimes we don't even know what happened — things just happened.

Reflection usually only works long after the fact, because in the moment there's emotion in the way.

Sometimes it's the emotion itself that makes us do things we shouldn't.

Sometimes reflection is just a way to make peace with our past selves.

If it's about making peace, you don't need to write it. Knowing it in your heart is enough.

After you finish all six

Two things I'd recommend after writing all six.

First, put the worksheet in a drawer and pull it out three months later. You'll find some "missed" things are still standing right where you left them, waiting. Some "should-haves" have quietly disappeared.

Second, find someone you trust and talk it through. Not to debate the answers — to let them challenge your "whys." The reason you think you have is often not the real reason.

The Six WHY isn't a one-shot test. It's a ritual you can re-do every few years.

FAQ

Q: Do The Six WHY questions have to be answered in order? A: Yes — go in order. Question 1 (what you did right) is the anchor. People who can answer it honestly find that the other five answers surface on their own. If Question 1 stalls you, walk away and come back in a few days.

Q: How often should I do this exercise? A: I do it around my birthday every year — comparing year to year shows me my decision patterns. For most people, every 1–3 years is enough. Any shorter and you won't see the change.

Q: What if I can't write anything down? A: Usually it's "afraid to face it," not "no answer." Start with Question 2 (what you concretely did) — facts are the easiest entry point. Once the other five flow, come back to Question 1.

Q: I'm in my early twenties. Is this exercise even for me? A: Yes. The point isn't how long a life you're reviewing. It's building the habit of looking back.