Have a direction, not a plan

When I was in school, I remember during my freshman orientation course for Computer Science, one of the professors said that if you want to do the 5-year Master’s degree track, you had to “plan ahead”. This mean having a strict plan of the courses you were going to take per quarter, and making sure they all added up accordingly so that you could graduate with a Master’s degree within those 5 years.

I didn’t take that track because I didn’t want to at that time, but even as college went on, I found the generic wisdom of that advice to be flawed:

1. There were so many people fighting for the classes they wanted to take, especially in an impacted CS program that seemed to have more students than it had classes. So there was no way that a highly rigid gameplan would have survived beyond maybe the 1st year of classes.
2. Reflecting on everything that has happened in college, there was a lot of unpredictable life things that affected my motivation and schedule during those years. I think people who were extremely focused on getting that Master’s degree, and didn’t have anything super distressful happen to them, would have had their original plans intact.

After 7 years in the work force, I’ve realized that it’s always better to have a direction of where you want to go versus having a strict plan. Plans are inherently inflexible and brittle; if one thing goes wrong and you can’t adapt the plan, then everything breaks for a bit. Directions are more fuzzy and anti-fragile; even if something goes wrong, you can adapt and adjust the direction, and still move forward.

That time when my plan went wrong

I wrote about this very early on (🚸On competitive Bay Area high schools and their rippling effects ) but I distinctly remember in high school, I had a plan to go to a top tier university. It required years of focused concentration on AP classes, bringing my “A game” to every sport and club I joined, and generally just giving my heart and soul into becoming the best candidate for the college I wanted to go to.

This plan was like a house of cards. All it took was a “B” in a class for the balloon of pressure to pop for me, because getting a “B” was not part of the plan. And that’s basically what happened. I thought my plan, and my life was over at that point. Seems very, very, very silly now that I reflect on it as a 29 year old. But that is an example of how worshipping a plan can go way too far, and affect you mentally as a person if you try to stick too much with it.

I often say this to my friends in real life, but I wish I had more of a direction in high school, because it would’ve allowed me to zoom out and think of the bigger picture. In hindsight, my plan and goals at this point in life were very naive. I’ve learned that it really doesn’t matter which college you go to, so long as you learn and network with the right people accordingly. A better direction would have been to learn as much as I can, and to work more on self-discovery and what I enjoyed doing, not just what would’ve gotten me into a good school.

There were friends in high school that had that direction, and I can say that today they’re much better for it.

What is a direction?

Overall, I would describe having a good direction as having a very loose plan instead of a strict one, where you fill in the minor details along the way, and are open to adjusting if things need to stall or something goes wrong for a bit.

One thing that has always helped me maintain direction is to build optionality at certain waypoints in life. Basically, a series of “if-this-then-that” forks. You never want to feel like you’re stuck because things aren’t going according to plan. In the college example, I always had a handful of 3 or 4 classes that I could sign up for, even if they weren’t exactly interesting to me. Mostly because I was able to determine that the direction I wanted was a technial degree and a SWE job, and whatever helped me get that was “good enough” for the plan (even though looking back, there were a few interesting classes I missed out on).

Another more recent example: I had no idea that this year I would move to Philadelphia, but it directionally made sense for myself and Jillene because she wanted to go into a great nursing school program, and I wanted a change of pace and escape the SF monoculture for a bit. I don’t think we knew until March that this was going to happen. But it was directionally aligned, and it ended up being a great decision for us and our current life stage.

Another thing that helps with direction is appreciating the amount of time it takes to reach the final destination. I think being early-to-mid twenties in a dense metropolitan area tends to surround you with a lot of folks that like to rush through life. I think appreciating the fact that yes, it does take time to make money and gain experience, allows us the time and space to figure out where the time boxed waypoints in life should be, as well as give us more space to figure out the options we could take when it’s time to make a decision.

Be untethered

We never know what life is going to throw at us. Family might get sick and we may need to take leave from work to help with that (trust me, I would know as part of my current corporate job). Jobs might be scarce due to the macroeconomy. So to be flexible with a direction will always be preferable IMHO than a strict plan that doesn’t.

A strict plan feels like a prison, but a direction gives you the freedom and motivation to do anything you want.