6 Things I’ve learned about careers in the last decade

I’ve been working full-time for the past decade or so, and here’s everything I’ve learned about careers.


Believe in your f***ing self.  That’s it.  That’s all that matters.  Everything else stems from this.  

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1. Failure opens doors to success.

My first job out of college was in customer support/sales in Tokyo.  Getting that job was a total fluke.  One month into it, I got fired.  I couldn’t speak or write Japanese very well, so my company didn’t want me talking with customers.

I was devastated.  Who gets fired from their first job within a month???

Youre Fired Donald Trump GIF

Turns out it was one of the best things that happened to me.  In the subsequent weeks,

  • I got moved into the marketing department at the same company.  Even though they’d fired me, they let me stay for a year, and my job was much more interesting going forward.
  • Because I was not allowed to stay at my job for more than a year, I got into business school at MIT Sloan at age 23.

When one door closes, you’re forced to find another one to open, and that one could be better.

2. Don’t worry about what other people think.

One day in grade school, I was upset by something that some kid on the playground said.  My dad said, “Don’t worry about what other people think.  They can think whatever they want.  They can think you’re 10 feet tall, and there’s nothing you can do about it!”

This turned out to be the best advice I’ve ever followed.

In late 2008, Sequoia came out with their famous presentation on how they were going to stop investing.  This was a week before I’d planned to turn in my 2 week notice at Google.  I briefly thought that maybe I should not go through with leaving Google to start my own company.

In the end, I decided to leave.  I left during the biggest downturn in the last decade.  Everyone thought I was crazy and stupid, and lots of people told me so.

Believe Black And White GIF

This turned out to be one of the best decisions of my career.  Had I cared what other people thought, I would’ve lost out on the opportunity to learn a TON about growing a company, work with amazing people and partners, sell my company, and get multiple opportunities to join various VC firms as a partner (not to mention a financially better outcome than staying at the GOOG all these years…).

Worrying about what other people think prevents you from taking risks and, by definition, limits your reward.

3. Persistence trumps all.

When you learn to play the piano or soccer, people always tell you to practice to get better.  You read stories about Michael Jordan, who got cut from his basketball team initially and then practiced night and day to eventually become the best basketball player to play the game.

When it comes to other things such as starting a business, no one tells you to practice.  No one tells you that you need to do 5-100 startups before hitting upon some semblance of success.

Since high school, I’ve had many startups and side projects including Pajel, Bazaar, The Stacks, &Backpocket, Parrotview, Shiny Orb, DressMob, and LaunchBit.

The first one (Pajel) was horrible.  It was a web design company that my friends and I started in high school.  This was in the dark ages when no one had websites.  We had 0 paying customers. Zippo.  Nada.  I was so scared to talk to customers, so no one paid us.

Each venture I’ve done has gotten better.  Still no billion dollar successes yet, but each one has been a step in the right direction.

Goals Just Keep Swimming GIF

For LaunchBit, I was still scared to pick up the damn phone, but I had no choice in the beginning. I had to work the phones, or we wouldn’t have ramen to eat.  Like everything else, you get better.  By the time we brought onboard our first sales hire, I had sold near $1m in ads myself.

Anything worth doing is hard.  Just keep going.

4. Optimize for one thing.

There are many blogs that give you advice on what job you should take.  They tell you things like: Take a big corporate job that will challenge you.  Work at a startup.  Start your own company.  Work for the best boss possible.  Hop on a rocket ship.

You can only optimize for one thing at a time in your career.  Think about what that one thing is.

In my early 20s, I optimized for travel.  I wanted to be paid to work internationally.  That’s it.  This is how I ended up working, interning, and doing gigs in Switzerland, Japan, New Zealand, and India between college graduation and when I turned 25.  During that time, I had to forgo making lots of money or working at a notable company or fast-growing startup, or even living near my friends in San Francisco.


What you optimize for may change over time, but you can only optimize for one thing at a time.

5. Find feedback buried in a haystack and improve yourself.

We all hate criticism and avoid it, but the best thing you can do for yourself is actually the opposite: grow a thick skin and seek feedback on how you can improve yourself.

The best entrepreneurs I’ve met – even rejected – ask questions like, “What can I do to win your business?”  Or, “What would it take to get you to say yes?”

Feedback is sometimes very nebulous, though.  I remember pitching one investor on my company LaunchBit.  At the end of that meeting, I asked him, “So what do you think?”  to which he responded, “Well, I don’t want to say the wrong thing and call you a meek Asian woman, but I question how you will lead 100 people…”

I was shocked.  And pissed.  Who says that?

Days later, I was reflecting back on that conversation.  I started to look at it in a different light.  I was no longer thinking about it in an angry way, but rather, what could I learn from it?  Clearly, he didn’t have conviction that I could lead a company.  If he didn’t have conviction, then how many other investors also didn’t have conviction?

Going forward, I did everything I could to combat any “meek-Asian-woman” impression that investors might have when meeting me.  I became over-the-top loud.  I sat up in my chair more.  I was more outgoing.  And it worked.  After that, I closed a lot more investors.

6. Keep perspective

As an entrepreneur, it can be easy to lose sight of the big picture.  A customer asks for a $45k refund – and you’re wondering, how am I going to deal with this?  (True situation that happened to me).  Your problems can feel so big and overwhelming sometimes.

But, in the last decade, I’ve had several friends my age die.  Cancer, car accidents, childbirth, and other sudden unfortunate fates have taken them.  Though there are plenty of problems left to solve, we live in an amazing world, and all of this can be gone in an instant.

Time is actually your most important commodity, not money.  You don’t know how much more time you have, and every day that passes, it becomes even more valuable.

Keep perspective and make sure that you are using your time wisely.

Happy Thanksgiving everyone!


Cover photo by Simon Abrams on Unsplash

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