practicing grounded optimism
"The world is built on 'and' [...] have an open mind." -- Alfred Lin
Summary
I was recently reminded how being optimistic is (1) a muscle that can be trained and makes me stronger, and (2) even more useful when I stay grounded (aka not toxic positivity).
Full
When I worked at Zappos, I heard a lot of good things about the former CFO, COO, and Chairman Alfred Lin, a Taiwanese-American who had already joined Sequoia VC as a Managing Partner by the time I started working there.
He was a recent guest at a podcast I like called The Knowledge Project with Shane Parrish, so I gave it a listen since I was curious why he had such a great reputation at Zappos. It didn’t disappoint!
Alfred’s insights were mostly targeted towards the tech community and were quite relatable, and I’ll expand on them more later, but I listened to this episode because I wanted to get to know him better and understand how he made such a big impact at Zappos, to the point that even after he left, people still spoke of him so fondly at such a large company.
Overall, I think his attitude of always seeing the positive side to things, though not in the naive or ignorant way, is probably how he was so successful in helping build Zappos and is now a renowned investor at one of the leading VC firms in the world.
It made me think about how most successful people I know all have this kind of perspective. I think it’s a valuable human trait to hope and believe in the future as well as in the goodness of the world, while at the same time, being naive or ignorant about it starts to enter toxic positivity territory, so it’s also important to acknowledge the negative situations in life, which then can lead to figuring out how to overcome them.
And based on Alfred's sharing, it seems like this mindset is something that can be built and ingrained in yourself over time (something his dad taught him and something he’s teaching his son now).

Here are some examples of the lessons shared by Alfred that emphasizes grounded optimism:
He was taught by his dad that you can learn something from every single person in the world, and that you are the accumulation of all the things you learned from others;
The best companies keep pushing and have a higher velocity, which is a better measurement than speed because it includes both direction and force;
Removing obstacles are just as important as applying pressure. Leaders tend to focus on applying pressure more than removing obstacles, and the good thing is that it sometimes leads to identifying what obstacles need to be removed;
The first sign of hubris is too much success, so you need to actively work to not be complacent. It’s too easy to ruin your reputation and generally, people value good processes > quick decision-making;
Strategic planning should also be looking backwards, not just forward, on what we did right vs wrong;
Founder mode vs manager mode is actually just an evolution of a founder’s journey of working and thinking differently about their company. “It pains me to see you have to choose. Calling it creator mode instead of founder mode, then operator mode to make their creations better;”
Figuring out the process before you start the journey is the path to success.
Personally, being realistically optimistic is something I’ve been trying to practice too.
I believe most people don’t want to see themselves as negative people, but being optimistic isn’t the equivalent to being happy. I think optimism is closer to adjusting the mindset to see the good side in things that are happening, to give people the benefit of the doubt, and to trust that most people don’t have bad intentions.
Sometimes it’s not easy, especially when someone doesn't have malicious intent but the outcome turns out really bad. In these scenarios, I tell myself that it’s ok to be upset about this specific situation while still staying optimistic on the whole (even though it can be really hard in the moment to feel better about it).
Overall, I think I’m getting better at being optimistic, but there's also the chance that I’m just at home so much these days with the baby that I don’t encounter enough situations that might make me angry.
On the other hand, I think I need to be more intentional about the “grounded” part and check myself when it comes to toxic positivity. It’s easy to brush off bad things and only focus on the positives, because I think I would probably get very sad (among other emotions) if I think too long about the negatives. I see it as a kind of coping mechanism to mask the “bad” feelings within.
However, in these moments of pain and suffering, we do tend to grow our character, and then we find a way to become better and stronger. I mean, if Jensen Huang says so, there must be some truth in it, right?
Being more mindful about grounded optimism has made it easier over time to retain this mindset for every situation. I definitely still have many moments where I feel neither optimistic nor grounded, but as I try to move myself back on track, I’ve slowly noticed that I’ve been getting better at it over the years. Nowadays, bouncing back from a setback is a lot quicker than it used to be!
Here are some other great lessons I got from listening to Alfred’s interview:
He learned from a math teacher that it’s not enough to know how to solve a problem correctly, but to be a good leader, you also need to know how to get the team to perform their best;
It’s valuable to have people who are different from you to keep you accountable and ask different kinds of questions;
You can’t just be better, you also have to be different;
Many good decisions are about sequencing. Knowing what’s right is one thing, but how you do things is what will define you.
Thank you for reading the second edition of munchies!
I created a Google form where you can share ideas or feedback. Do any of Alfred’s takeaways resonate with you? Would also be interested to hear if you disagree or have another angle to see things ~