#118. Design an Asymmetrical Life
More Upside, Less Regret—By Design
Welcome to the blog post #118! Click here to read more from previous posts.
“What would you do if you knew you could not fail?”
That was the question Graham Weaver posed in The Last Lecture Series at Stanford’s Graduate School of Business.
I realized I had never seriously asked myself that question before.
I’ve always believed in being practical. So I often thought about the “how” before defining the “what”. And when that mindset combined with limiting beliefs, the “what” became smaller. Safer. More realistic.
But Graham’s question flipped my thinking. It challenged my default approach.
In addition to teaching at Stanford, he’s the founder and CEO of Alpine Investors, a people-driven private equity firm. Beyond business acumen, he’s widely respected for his reflections on how to figure out what to do with our lives.
In one of his lectures, he talked about the idea of living an asymmetrical life, and that concept deeply resonated with me.
What Is an Asymmetrical Life?
In investing, we often hear that high returns come with high risk. But what if you could create a life where the reward is high and the risk is low?
Designing an asymmetrical life means intentionally making choices where the upside potential far outweighs the downside risk. It’s about positioning yourself so that a few bold decisions, meaningful habits, or well-placed opportunities can compound into extraordinary results, even if many others don’t pan out.
Here are four ideas I’ve reflected on from Graham Weaver’s lecture that can help shape such a life:
1. Do Hard Things
You can’t expect meaningful results, in fitness, work, or life, without putting in effort and embracing discomfort.
Athletes don’t win without sweat. Muscles don’t grow without pain. Results don’t show up without action.
But in today’s world of instant gratification, we expect progress without the process. We want results without sacrifice.
And the truth? Everything worth having lies on the other side of “worse first.”
That first attempt at change is often awkward, uncertain, and yes—worse. But stay with it, and something better is waiting.
Hard things are often what most people avoid:
Choosing a less conventional career path that excites you more than a “safe” one.
Creating your own rhythm of life instead of chasing the latest trends.
Studying after work instead of scrolling through social media.
Your hard things are often the things you fear. But that’s also where the greatest growth happens.
2. Do Things That Create Energy
Naval Ravikant, a tech entrepreneur and philosopher, once said:
“Find what feels like play to you but looks like work to others.”
That’s energy. Unlike willpower, it’s not limited. In fact, the more you use it, the more you gain.
Graham shared a quote that stayed with me:
“Life is suffering. So choose something worth suffering for.”
It’s a sharp contrast to feel-good self-help quotes, but it’s real. Growth always includes struggle, whether you’re building a business, a body, or a better self.
The question is: How do you keep going through the suffering?
The answer is: Do what brings you energy.
Not what’s easiest. Not what looks good on paper. But what deeply matters to you. That’s your renewable energy source.
3. Do It for Decades
Success doesn’t come from shortcuts. It comes from showing up consistently over time.
But effort isn’t sexy. We often only hear the end of the story—the results, the fame, the wealth. We rarely hear about the quiet, consistent effort behind it.
Graham reminds me that nothing can stop us if we do what excites us, not for months or years, but for decades.
It also reminds me of Warren Buffett. Despite being one of the greatest investors of all time, 99% of his net worth came after his 50th birthday. Just take a look at the chart below.
Source: Finmasters
We often admire the scale of his wealth but underestimate the decades of patient investing that built the foundation for it.
There’s no secret hack. The real edge is staying in the game long enough for compounding to work its magic.
4. Write Your Own Story
This part hit me hardest. Graham shared a piece of advice from his coach:
“Imagine yourself five years from now. What’s your nirvana? What would you do if you knew you could not fail?”
He said that the “how” is the killer of great dreams. We get stuck trying to plan every step instead of letting ourselves dream freely.
Don’t write a story about what’s already happened.
Write the story you want, and then go make that happen.
Of course, it’s not easy. Fear is always there. That’s why Graham suggests you name your fear, write it down, and then act immediately—before fear and procrastination take over.
Brian Tracy calls this “eating the frog.” Each of us has our own frogs—our fears—that we must face if we want to live out our dreams.
So don’t say, “Not me, not now.”
Because that usually means “I’ll never do it.”
Living an asymmetrical life isn’t about recklessness or chasing every shiny object.
It’s about placing thoughtful, bold bets on ideas, paths, and habits that, if they work, could change everything, and if they don’t, will still leave you stronger.
It’s about shifting from “How do I avoid failure?” to “What would I do if I knew I couldn’t fail?”
So start there.
Then design a life that makes that answer possible.
That’s all for today. Till next week!
Cheers,
Do Thi Dieu Thuong