Struggle (failure) or how we get better

Rose Yao
5 min readJan 23, 2019

I was lucky enough to have the luxury of almost 3 weeks unplugged from work. This means pilates/spin/yoga most days, all the chores I’ve been meaning to do (marie kondoing my closets), lots of cooking, a trip to Europe with my husband, and binge watched Game of Thrones. This time has also given me space to reflect about what I hope for in 2019.

I’ve been thinking about how we help each other. Most of my posts try to distill something complex that took me years to learn into a 3–5 min story with actionable takeaways. A lot of them follow a classic ‘hero’s journey’. There was a goal, then there was a struggle, and finally I conquered it. Here’s how you can too.

I don’t write about the struggling nearly as much as I do the conquering. And I’m not alone. We don’t like to relive tough moments and we don’t like being vulnerable. It’s nice to make the hero’s journey look easy in hindsight. But is that really helpful? The tendency to mask one’s struggles became more apparent to me last year when I noticed a common question amongst young PMs I mentor.

“I don’t think I am good enough. If I’m struggling this much, I must not be special or l might not be cut out for this job. ”

That’s not true, everyone struggles. So here’s a post dedicated to the struggles. Because that’s the part of the story that really matters and it’s where real growth comes from.

My top 3 struggles

#3: the beginning and crying at work

I was very lucky to join Google as an APM. I had my dream job as 1 of 2 PMs on Gmail, the newest and most exciting product at Google. I was surrounded by confident and smart people who were building the future of communications. It all sounds great!

Being a Gmail APM was far from easy. At that time, Google was pretty chaotic and my manager left the company my second week on the job. A job I had no idea how to do… Everyday I struggled to figure out what I was was suppose to doing and the other PM on the team made it look so easy. I couldn’t figure out why I was struggling so much.

My first round of performance reviews actually made me cry at work… For someone who’s gotten straight As for a decade, it was a rude awakening. I was trying so hard but I just had a lot to learn. I struggled to add value in a high functioning team, to build consensus and drive decisions, and to think clearly about product design. It didn’t all soak in immediately, but there’s no doubt that the feedback made me more focused and helped me become a better PM. Thank you to everyone on the Gmail team for their patience and mentorship. Particularly the design team who gave me a crash course on what product design was.

#2: fb years — not thinking big enough

I left Google to join Facebook in 2010. It was a pivotal moment in Facebook’s history. I felt confident that I knew how to be a great PM and I wanted to leave my mark on Facebook during a time where anything was possible. Luckily, I got the opportunity to work on some great products with great people: early mobile, profile, platform, and photos.

My struggle began as I stepped into leadership positions and got consistent feedback: think bigger, be visionary, and be more strategic. What did that mean? To say I was frustrated and felt like an imposter is an understatement. There is no hero’s tale here. There was no eureka moment when I suddenly became Steve Jobs. It took hard work, a lot of trial and error, a lot of humbling myself to ask for help and a lot of listening before I started to understand how to create real product strategies. I am forever grateful to my coworkers at FB who taught me how to think about strategy and the psychology of a product.

#1: Athos — startup life and leadership lessons

I’ve written a lot about my time at startups. I have posts on joining a startup, hiring for startups, advising for startups, and etc. Makes it sound like I have it all figured out. Well… I’ve learned a lot but I definitely don’t have it figured out.

I went into Athos with a lot of assumptions. I did the opposite of what I now tell every new person who join my team: take time to really listen, to figure out what the team needs from you, to form relationships before forming opinions. I went in with strong opinions and I didn’t take time to listen and build consensus. I got swept away with that startup sense of urgency and a giddiness about finally being the decider. I didn’t take the time to get the whole team on board and so when the results weren’t immediately positive, it wasn’t hard for everyone to doubt and question the strategy we took. This experience has made me approach leadership and team building very differently today than I did before my time at Athos.

No Regrets

That’s it. I don’t regret any of my struggles because they taught me important lessons as a leader and as a human being. I came out of each of those journeys better and more self aware. But it wasn’t easy and it wasn’t always pretty. I hope this post helps everyone in the middle of their own struggle right now. You are not alone and the greatest growth only comes from the greatest struggle.

I can’t resist ending with this quote from Theodore Roosevelt

The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.

Happy 2019!

May we conquer our current struggles whatever they are and may we all feel a little safer sharing these struggles authentically.



Rose Yao

I spent the last 16+ years building products mostly at FB and Google. Also a food, travel, and fitness addict. Follow me @dozenrose or on