"Your (university) major is your insurance policy," my classmate noted.

We were role-playing during our coaching certification class back in August 2023. I had volunteered to be the client, hoping for some clarity about pivoting out of tech.

The phrase "insurance policy" made me uncomfortable, because it was true.

Today, I'll be delving into:

1. What an "insurance policy" endeavor is
2. How much insurance is too much insurance
3. How I'm managing my "insurance policy" endeavors

What is an "insurance policy" endeavor?

It's a Plan B that you put time and effort into, just in case Plan A doesn't work out.

For example, my Bachelor's in Computer Science—specifically, AI and Machine Learning—had been my Plan A since August 2021.

However, I felt increasingly dehumanized as I applied for internship after internship in my first two years of university.

This made me doubt whether doing tech in the traditional employment sense is the career I want. So I took my own advice: I deliberately experimented with online writing and content creation in Summer 2023.

I ended up liking it more than tech, and I've decided to pursue it as my Plan A.

However, I'm still dedicating time and effort to my academics so that I have something to fall back on—in case my Plan A doesn't work out.

How much insurance is too much insurance?

When you buy insurance, you're usually protecting yourself against emergencies and catastrophic events.

These events might never happen. In that fortunate scenario, you (unfortunately) won't get the money you've paid back.

Thus, if you buy too much insurance, you're spending a lot of money on something that has a low chance of returns. That money could've been invested towards growing another source of income.

The cost of insurance policy endeavors is similar: The time and effort you spend on Plan B could've been used towards accelerating your progress on Plan A.

When your Plan B starts interfering with your Plan A—that's when you might have too much insurance.

How I'm managing my "insurance policy" endeavors

In 2019, I was blessed to read There's No Plan B for Your A-Game.

In this book, former NFL All-Pro Bo Eason describes how his single-minded focus and dedication helped him manifest his 20-year life plan—a plan he first created using crayons when he was 9 years old.

Applying this single-minded focus has helped me achieve my goals in the past 3 years. However, as I grow older, I also realize that circumstances, constraints, and curiosities can—and will—change over time.

Pursuing Plan B while executing Plan A can help you adapt better to these changes.

So, my current principle towards insurance policy endeavors:

You can pursue Plan B as long as it doesn't interfere unsatisfactorily with your progress on Plan A.

Based on this principle, I came up with 3 strategies to manage my Plan B better:

1) Check if pursuing Plan B satisfies your constraints

I have two big constraints for my university studies:

1. I can't change my major. If I switch my major now as a third-year student, I'll have to delay my graduation to fulfill my new major's requirements. This is something I don't want, so I can't change my major.
2. I can't drop out of school. If I do that, I'd have to start over again at a university in my home country, Singapore. It's not a bad environment, but not a conducive environment for me to be in either.

Continuing my Bachelor's in Computer Science will satisfy these constraints, so I won't drop it.

2) Assign a stronger purpose to Plan B (if needed)

My grandma couldn't read or write.

She was born into a very poor family during World War II—a very patriarchal period where educating girls was viewed as a waste of money.

However, she saw how formal education—and having a Bachelor's degree—had unlocked numerous opportunities for other people.

This spurred her to work hard—at one point, she was working three jobs—to put her three kids through high school.

Naturally, my grandma was worried when I told her about my gap year plans. The people she knew who took a break from school to earn money (my parents included) never attended university in the end.

So, before I started my gap year, I promised her that I'd graduate from university.

And no matter how much I dislike my major now, I'm not going to break that promise.

3) Focus less on outcomes and more on the process

Whenever my academics (Plan B) got in the way of my Plan A, it was usually because I was focused on getting good grades.

I haven't found a way to completely detach myself from grades. But focusing on the process of getting good grades has helped immensely:

• Striving for intuition and understanding about what's being taught (not regurgitation ability)
• Practising for progress in a particular skill (even if they're baby steps)

This also shifts my focus towards skills and experiences—the best assets you can acquire when pursuing any endeavor.

Note: Doing Plan (A + B) well will require more effort.

So, if you can go all-in on one thing, do that.

But if you can't do that yet:

1. Check if pursuing Plan B satisfies your constraints
2. Assign a stronger purpose to Plan B (if needed)
3. Focus less on outcomes and more on the process

Take care, and I'll see you next week!