The context behind the advice

This was originally written for a short keynote talk at a University of Washington mentorship event on 1/29/19.

Hi there. I’ll keep this brief as I know you all are excited to talk with your mentor or mentee.

I want to talk about just one thing; the context behind advice.

I was recently reflecting on a conversation I had with a student who wanted to talk about venture capital and startups. She had reached out to me because of my work experience, but looking back, I realized that so much of what I was saying was actually a reflection of my life experience. A life experience very different than hers. She came from an unstable, single parent household, where meals and housing were consistently as risk, and much of her family was plagued by incarceration.

In contrast, I was blessed into a loving, stable family where, while we weren’t rich, we had our basic needs covered.

And yet this difference in our background wasn’t known to her, but it mattered. It still matters.

I realized that advice comes from our individual experiences, and our individual experiences comes from the world context we were born into and how we handled that.

A great example is the advice to "focus less on grades and more on learning outside the classroom", through side projects and internships. This is how I personally approached college and it worked out for me, but there's so much context behind that advice. This comes from someone who doesn't have a GPA-minimum scholarship, doesn't have to maintain a minimum number of credits for international enrollment, and has open minded parents that can stomach this risk. All these factors are the context I was born into that enabled me to make the choices I did.

This isn’t to say that a difference in context makes one’s advice invalid, but simply that understanding where the advice is rooted from helps you calibrate their words.

Vinod Khosla, a legendary venture capitalist behind over a half dozen billion dollar companies, recently said in an interview that “the single hardest decision you’ll make is who’s advice to trust on what topic.”

The more you know about who is giving you advice, the better you can assess and internalize their words. This plays even more importantly in mentorship, where topics go beyond just how to code or design, and deeper into one’s ambitions, goals, and their definition of success.

Today, whenever I meet a student who wants advice or when I meet with someone I want to learn from, I try to take time to learn about their life story, beyond the resume.

Things like where they grew up and what that was like, to what their values are today, and what their ambitions are for tomorrow. What sculpted their individual worldview.

Tonight, we have a good amount of time. I challenge you to take some time to dig a bit deeper. And while it may feel awkward, or uncomfortable in the beginning, I promise that if you approach it from a place of genuine curiosity, what will result is a stronger, lasting relationship built on trust, understanding, and advice through their context.

Enjoy tonight, and best of luck.


Here is the context that influenced my world views and outlook. Your mileage may vary.