In 2004, I was the PM for the largest product launch in the history of PayPal - making PayPal fit domestic China (L10N and I18N only covered the tip of the iceberg).
Then disaster hit - PayPal went down for a week (I saw it on CNN in HK!). Code red, all resources pulled, China project went into hibernation. However, as Deb said above, I couldn't guarantee we'd win China, but I knew for sure that we'd lose if we didn't even enter the market.
It scared me to death to write up an options document (e.g., we could build the product with eBay's dev team in China) and sending it up the chain, skipping my manager, and manager's manager when I wasn't getting any responses. Yes, I was ignoring corporate hierarchy, but I believed in the cause more than my personal welfare.
4 months later, with PP (sort of) stable again, the senior execs at PP swapped roles with eBay (career rotation for them), and suddenly the new CEO asked about China. A scramble among my bosses surfaced my options doc. I was called in before the new CEO. One of my options was picked, and we were back in the game: deliver to the original date (6/2005) after having lost 4 months.
Needless to say, it was insane but we delivered. Yay, success, right? Well, as you may know, our parent company (at that time) eBay lost the China market to Alibaba's startup TaoBao, and we, PP, consequently lost to Alipay.
Tragedy right? Well, after 18 months of useless JV work, eBay skipped out of town, but we convinced PP execs to keep the PP cross-border (XB) experiment going - helping Chinese merchants sell to the 100+M PP buyers around the world.
5 years later, we grew that tiny business to over a quarter million dollars in revenue. With huge profit margins (XB margins >> domestic).
So I got promoted to VP, right? Nope, China was the largest country by revenue (and profit) in Asia Pacific, but I was still Sr. Director. My friend, coming from SJ, became GM in Australia, smaller by revenue but a large domestic market, at VP level.
What does this all mean?
- You miss 100% of the shots you don't take
- Failure begets success, but success in one area (e.g., product) may not mean overall success (e.g., market)
- Meeting / beating metrics doesn't mean you'll get promoted. How much was it glass-ceiling being an Asian American? Maybe some, but now that I'm out of the rat race, I think it's because I didn't play the corporate game. When I flew back to HQ in SJ, I didn't go drinking and play golf with my bosses, so when it came promotion time, the known entity back home got more votes than the guy quietly delivering across the ocean.
I hope this story gives you some other Perspectives on navigating your career so you can learn from my "failures."
Having known you from the day we met in that interview, seeing you thrive and struggle and thrive again has been encouraging. You are so much more than a title and promotion. We are all better having worked with you.
What stands out here is how often fear of failure hides inside “competence.”
High performers think they’re being careful, but really they’re protecting an identity they were praised for early in life — smart, reliable, the one who always delivers. The irony is that the higher you rise, the more that identity becomes a constraint.
In my experience, nothing shifts a team faster than a leader who models failure out loud. When we stop treating mistakes like quiet personal flaws and start treating them as shared data, the whole room changes — ideas surface faster, risks get smarter, and people stop managing their image and start managing the work.
The article nails it: the real leadership leap isn’t about getting more right.
Accept a mis-judgement in public and what you learned from it. Showing vulnerability is not a sign of weakness. It is a sign of self-confidence and a way to build trust and let your teams know that taking risks and failing (failing fast) is an option
In 2004, I was the PM for the largest product launch in the history of PayPal - making PayPal fit domestic China (L10N and I18N only covered the tip of the iceberg).
Then disaster hit - PayPal went down for a week (I saw it on CNN in HK!). Code red, all resources pulled, China project went into hibernation. However, as Deb said above, I couldn't guarantee we'd win China, but I knew for sure that we'd lose if we didn't even enter the market.
It scared me to death to write up an options document (e.g., we could build the product with eBay's dev team in China) and sending it up the chain, skipping my manager, and manager's manager when I wasn't getting any responses. Yes, I was ignoring corporate hierarchy, but I believed in the cause more than my personal welfare.
4 months later, with PP (sort of) stable again, the senior execs at PP swapped roles with eBay (career rotation for them), and suddenly the new CEO asked about China. A scramble among my bosses surfaced my options doc. I was called in before the new CEO. One of my options was picked, and we were back in the game: deliver to the original date (6/2005) after having lost 4 months.
Needless to say, it was insane but we delivered. Yay, success, right? Well, as you may know, our parent company (at that time) eBay lost the China market to Alibaba's startup TaoBao, and we, PP, consequently lost to Alipay.
Tragedy right? Well, after 18 months of useless JV work, eBay skipped out of town, but we convinced PP execs to keep the PP cross-border (XB) experiment going - helping Chinese merchants sell to the 100+M PP buyers around the world.
5 years later, we grew that tiny business to over a quarter million dollars in revenue. With huge profit margins (XB margins >> domestic).
So I got promoted to VP, right? Nope, China was the largest country by revenue (and profit) in Asia Pacific, but I was still Sr. Director. My friend, coming from SJ, became GM in Australia, smaller by revenue but a large domestic market, at VP level.
What does this all mean?
- You miss 100% of the shots you don't take
- Failure begets success, but success in one area (e.g., product) may not mean overall success (e.g., market)
- Meeting / beating metrics doesn't mean you'll get promoted. How much was it glass-ceiling being an Asian American? Maybe some, but now that I'm out of the rat race, I think it's because I didn't play the corporate game. When I flew back to HQ in SJ, I didn't go drinking and play golf with my bosses, so when it came promotion time, the known entity back home got more votes than the guy quietly delivering across the ocean.
I hope this story gives you some other Perspectives on navigating your career so you can learn from my "failures."
Having known you from the day we met in that interview, seeing you thrive and struggle and thrive again has been encouraging. You are so much more than a title and promotion. We are all better having worked with you.
What stands out here is how often fear of failure hides inside “competence.”
High performers think they’re being careful, but really they’re protecting an identity they were praised for early in life — smart, reliable, the one who always delivers. The irony is that the higher you rise, the more that identity becomes a constraint.
In my experience, nothing shifts a team faster than a leader who models failure out loud. When we stop treating mistakes like quiet personal flaws and start treating them as shared data, the whole room changes — ideas surface faster, risks get smarter, and people stop managing their image and start managing the work.
The article nails it: the real leadership leap isn’t about getting more right.
It’s about getting less afraid.
Accept a mis-judgement in public and what you learned from it. Showing vulnerability is not a sign of weakness. It is a sign of self-confidence and a way to build trust and let your teams know that taking risks and failing (failing fast) is an option