Captain’s Log

A dictated journal for an unprecedented moment

I’ve journaled on and off in various formats throughout my life.

I kept a paper diary, shifted to a “4 lines a day” style daily journal, moved to Day One’s electronic journal, and also do a personal review and quarterly updates to friends. Plus I write a monthly update for my investors for my business.

I’m trying something new that I wanted to share — a digital journal powered by voice.

Think of it like a captain’s log. The original term (sometimes ship log or logbook) was used to document a ship’s position, wind speed & direction, and … Read the rest

33

Developing a new mantra

I turned 33 a few weeks ago.

I remember when my gymnastics coach turned 33 and told me about it. I was 12. He was not only my first serious gymnastics coach, he was one of the owners of the gym. He was in charge and he seemed to know everything.

I replied by saying that he had run through a third of his life. Probably not what he wanted to hear and but given he was a smoker, it was actually a pretty optimistic forecast.

Turns out of course that you don’t have it all figured out at 33, … Read the rest

Starting Over

Due to an unfortunate combination of bad actors and my own neglect, I’ve had to do a full reboot of my blog. I should be able to recover / republish many of the posts over time, but backlinks may be an issue, perhaps indefinitely.

While this is of course frustrating, there’s also a sense of relief. A fresh start. There’s something uplifting about a blank slate and having a chance to redefine myself and what I write about.

Early on, I tried to make everything I wrote a direct reflection of personal experience. My shield was always “this is what … Read the rest

32

Reflections on turning 32

I turned 32 a month ago and long-time readers know I try to use birthdays as opportunities to reflect and learn. The past couple years are here: 313029282726.

The past 13 months have seen a lot of change — I was part of a mass lay off, worked as a freelance product manager, got engaged, gave a TED talk, started a new company, raised capital, and helped people find exciting new job opportunities. As such, I have a new set of thoughts, sometimes a re-statement of … Read the rest

Goodbye Etsy, Hello World

Leaving Etsy and Starting Something New

I joined Etsy in August of 2015, five months after the IPO. I had admired Etsy from afar for years and I was excited do product at an established, publicly-traded technology company after leaving a privately-held B2B software company.

Over the past two years, I’ve built products and features to support our global seller community of 1.7 million creative entrepreneurs. I helped launch a marketing / promotional tool called Shop Updates, oversaw a major rewrite of the system we use to assess listing and transaction fees, and introduced powerful new functionality for Sell on Etsy, our seller-facing iOS and Android … Read the rest

31

31 Lessons at 31

It’s sort of a tradition at this point for me to do a post around my birthday (see: 3029282726. This year, I decided to write down 31 lessons I’ve learned in the past few years. Anything older than that tends to become a “known fact of life” and stands out a lot less.

These were initially written with modifiers like “most”, “often”, or “tend to”, but since that makes the points less pithy, I’ve taken them out. However, know that I don’t mean these lessons literally to be true in all … Read the rest

30

Photo by Martin Reisch on Unsplash

About a week ago I celebrated a major milestone and turned *gasp* 30. Over the last few years, I’ve kept very careful track of how much time I had left until thirty, which was the age I thought I needed to have “made it”. In retrospect, the anxiety was unwarranted and thankfully in my old(er) age, I’ve gained the wisdom to see that.

Yes, in getting older, I’ve lost some naïveté, I look a bit more before I leap, and I get hangovers. But I haven’t lost my enthusiasm for building new things, and … Read the rest

The 10x Job Application: What You Do When You Really Want the Gig

We talk a lot about the war for talent: the idea that organizations need to fight to recruit, retain, and grow great people. Harvard Business Review recently put it this way:

“Finding and nurturing ambitious, hard-driving, and international-minded managers and technical staff are major challenges for multinationals and will become ever more crucial. HR operations at many companies have traditionally been seen in terms of compliance, record keeping, and support. But as talent shortages grow more acute in idea-intensive industries, human capital management should become a much higher strategic priority.”

— The Future and How to Survive It (HBR October

Read the rest

Goodbye Percolate, Hello Etsy

Leaving Percolate and Joining Etsy

I joined Percolate in March of 2014 as the 100th employee at the company (today: 250+). Back then, we were all piled into a single floor of our NY office in SoHo. We’ve grown tremendously, raising two rounds of funding, opening offices around the world, and delivering The System of Record for global Fortune 500 brands like Unilever and GE.

But in the next chapter of my career in product management, it is time to say goodbye to Percolate, and hello to Etsy.

I bought my first item on Etsy eight years ago, as a Christmas gift to my college sweetheart, Olivia. It … Read the rest

The Extraordinary Power of Self-Reflection

I recently stumbled across an old document on my laptop. It was a PDF with journal entries from several years ago. While many of the entries were typical day-to-day activities, I also found about 100 short lessons that I had captured during this journaling period and I shared a few on Twitter.

Some of them were very specific:

As a panel moderator, you are the advocate for the audience – don’t just suck up to the big shots.

— Jason Shen (@JasonShen) July 16, 2015

Others were more generally applicable:

A few gems: If you don’t set clear expectations about

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