Friday, September 5, 2014

A little disorienting and a little wonderful

By day, I’m having discussions about Jaccard similarity and mutual information, or ways to filter noise in entity extraction, or how to design a new review process that incorporates a data snapshotting tool. 

Then I go home and I read people’s responses to the side project emails and I write questions like these:

The people you admire seem to have found a way to just show up as themselves in the world. It reminds me of a book review I once read where the author was complimented for “finding her voice and sustaining it”. I love that thought. What would your voice be like? What would it sound like, or what would it speak of? 

Tuesday, September 2, 2014

More things I have learned from the alpha test


More things I have learned, follow up from Part 1.

  • Why aren’t strangers replying?
    At least two “strangers” had not been responding because my email went to their spam folder. :( Now I’m wondering if this is what happened to all the others. I sent them all from my personal gmail, but maybe I shouldn’t have put “free” in the subject line even though Expt #1 is called “Free Advice from a Stranger”. Looks like I should use Mailchimp or something else next time. And drop the word “free”.
  • Is personalized observational feedback scalable?
    This high touch model is totally unscalable. So far I’ve gotten to the point where I’ve written observational feedback for 3 participants. Here is the thing - if someone takes the time to write substantive answers and shares personal details about their lives, you cannot give a quick or cookie cutter answer. So my observational feedback runs in the 800-1000 word range and each one takes an hour or two to write. Scale fail. But I really enjoy these high touch exchanges! Still need to figure out the right way to package the interactions. 
  • Standardized or personalized questions?
    So far I’ve been sending people random or personalized questions that mostly come from a question bank that I’ve collected over time. I’m going to standardize the questions, at least the initial set. It is not clear that varied questions bring a lot of benefit, but personalized questions that are tailored to the participant’s response do. 
  • How many questions is enough or too many?
    I only need 5 initial questions, I don’t need 15. The alpha test was supposed to be 15 questions, but that is seriously a lot. Got a bit tiring for me and the participants. I have discovered that if you ask 5 questions that cover a spread of topics (interests / goals / fears / people / etc.), you’ll see enough of a pattern to comment meaningfully on where the person is at. 
  • Would people just reply with one-liners or would they write more substantive answers?
    Most people have written far more detailed and thoughtful answers than I expected. There was a lot of material to work with, and I was impressed by how much people were willing to invest in this project. One person replied with one-liners, which made it very hard to draw meaningful observations. But for the most part, people were willing to use the questions to probe deeply. 

Ideas for things to try:

  • Switch to Mailchimp - DONE
  • Have a fixed set of initial questions - DONE
  • Send them at once, instead of one a day - DONE
  • Have a set structure for the observational feedback
  • Or have a 30 min call?
  • Focus on a specific topic within career advising so that there is less range in topics, less ramp up time for me, more structure in my responses
  • Try giving a mini homework project that is totally custom and helps the person turn something vague into something more concrete

How all this feels:

  • It is very hard to keep the big picture in mind, while fixing all the tiny details. The big picture is the conversations. It is the privilege of getting to hear someone else’s story and offering them a listening ear and a little outside perspective. 
  • Then there is an even bigger picture that I haven’t figured out how to connect my project experiments to. The even bigger picture is about all the theories I’ve collected about good work and fulfilling work, and how you should follow your passion or not follow your passion, and how a dream job is something you discover or it isn’t and it’s really something you craft. How to build all that into the project, while I am trying to fix the height of some form button? 
Friday, August 29, 2014

Learnings from a week of alpha testing

  • I have 15 alpha testers, out of which 6 are people I know personally, and 9 are strangers.
  • Most of the participants who know me personally have been active in responding to the emailed questions. None of strangers have responded to a single email. 
  • If I simply want to collect emails, then the current system is great. I was surprised by how many strangers were willing to sign up. 
  • But if my goal was to get more engaged users, I would do something like include a question in the sign up process, so it’ll be Name, Email, Answer this question. The question can be something like, “What does it mean to be creative in your work?” Raises the bar for a sign up, but it also filters out people who just want to be passive users. 
  • Why don’t strangers respond? Not interested? No time? Feels odd to share personal details with a strangers? Is mystery. Perhaps a silent stranger will be brave and speak an answer. 
  • I thought it might be interesting to let people sign up with a friend. I bet the people answering questions are very curious about what other people say. 
  • The original plan was for 15 days of 1 question emailed per day. After about 5 days, I realized how long 15 days felt. A user also said it was a little frustrating to have to write answers to all 15 before getting the “magics” so to speak. Writing answers takes a lot of effort! So I am considering a few adjustments:
    (1) Give the “magics” to users after 5 questions, then give an option to continue or not.
    (2) If they want to continue, I could send the next batch of questions at one go. 
    (3) We get into interesting combinations of how many questions before a “magics” response, and whether batches of questions are better than individual questions.
    (4) At some point in the process, I feel my question needs to be, “What do you want to tell me about your career? What do you want me to ask you?”
  • I feel like the whole exercise has been full of fascinating anecdotes. I love reading what every single person has written to every question. I have learned so much about people - in general - and how we really are. 
  • At the same time, it has me wondering about what the next experiment should be. I haven’t even finished Expt #1 and I’m thinking about #2, #3, right. But I feel like the manifestation of the project has shifted from the original inspiration for the project. It has me asking myself, what is the goal of this project? What is it that I believe? What do I want the world to have? 
  • In reading some of these answers to one of my favorite questions in the set, I had a true moment of enlightenment about what it means to struggle with receiving compliments. But I shall save that for another post. 
Monday, August 25, 2014

The kindness of strangers & an accidental alpha launch


As you have probably noticed, the career side project has been paused. For that matter, this blog has gone silent for awhile.

If you were wondering what happened, well, my day job happened. Got moved to a new product, new teams to work with, new role, some reorganization, a lot of new things to adjust to. It is all very exciting, and I do believe I’m onto what might become the most interesting role I’ve ever had, but it’s also quite exhausting. My work hours got a bit longer, but the real impact was on my energy levels. It has taken so much energy to adapt to everything new, that when I come home my brain is fried. The side project was born in a time when I was cruising, relatively speaking. It was not designed to complement a steep learning curve at the day job.

So the side project got paused. 

But! the internet is a curious place. Let me try to retrace this. This is a story that involves 3 people, all of whom I have never met in person.

I think it started with Gary Chou, who runs the side project bootcamp called OrbitalNYC, retweeting one of my blog posts. Then Nikki, who is also into side projects and has thought a lot about career pathing, saw the post and reached out to me. We had a video call and had a wonderful and very animated discussion about our career stories and how people approach their careers. Nikki told some people about my project, one of whom was Brendan, another participant in Orbital. He is working on a side project called the Self Starter’s Guide, which also involves rethinking how we think about our careers. He, too, reached out to me.

Are you following? Because now we get to the un-pause part. 

I sent Brendan a long email explaining my project, and by then I already had a live but not yet launched site, so I shared the site as well. The site has a box where you can enter your email and sign up for what I’m calling Experiment #1. The box happens to actually work. I know this because I got a notification that Brendan signed up for Experiment #1. I thought, “Wait a minute, I have an email sign up, this is not what I intended, what do I do now!” Of course, the answer is, “I should just start. Now.”

So I threw out all those grand visions of automated systems. In some future world, that would have involved Mailchimp plugged into something else and a well orchestrated drip email campaign that randomly and intelligently selects career questions. To start this thing, I literally just opened up a new email and manually typed the message and hit send. 

And there you go - alpha launch. 

While I was at it, I thought, why don’t I get a few more testers. So I emailed the handful of people who were kind enough to let me do user research interviews a few months ago, and invited them to sign up as alpha testers too. 

As of this evening, I have 3 alpha testers. I already have a couple of responses and it is so fun to see how people play along with this thing.

As for next steps, I plan to complete this round of alpha testing, which should take about 2 weeks. It should give me enough feedback for some tweaks. And then… and then we launch this thing for real. 

P.S. If you really want a sneak peek, you can guess at what the site is called based on the tags on this post. 

Monday, July 21, 2014

A snippet from About Me - My Career Story


One of the last things I need to write for the career side project is the About Me section. I had been putting it off because it just seemed so daunting. It had to be more than just a bio describing my employment history. I felt that, just as I would be asking for my audience share their career stories, I would have to share mine. I had to put it out there and that just sounded like so much hard work.

Yesterday I finally sat down on a clear afternoon and wrote 2800 words in 4 hours. A first full draft. It will need much revising, but the hardest part - the part that involves staring at a blank page - is done. 

Here is a snippet about a part of my career that I seldom share. It usually gets glossed over in the details, but looking back it marked an important change in my path.

Right before business school, I did something else that would change how I thought about fulfilling work - I created my own internship. It was perhaps the first side-project type work I had ever done. While at Goldman Sachs, I attended a presentation by the GAVI Alliance, a global health non-profit that works on increasing access to vaccines. I liked what they did, so I opened the brochure folder they had handed out and emailed the person whose business card was embedded in the folder. I introduced myself and said I would very much like to offer any skills I had to their good cause in the form of an internship. Much to my surprise - I had never cold emailed this way before - I was referred to a wonderful woman who was on their Board of Directors, and I would get to do an internship. I learned an important lesson: it is possible to create a job for yourself where there was none before.

Saturday, July 12, 2014

When other people have great ideas

It used to be that when someone else on my team came up with an idea, I would feel slightly bad. I would feel like, oh, I should have thought of that! I thought the way you contribute is to make sure you come up with the best ideas. 

Now when someone on the team comes up with a great idea, I’m thrilled. I think, I am so glad that we have a team dynamic that allows each person to voice great ideas.

I think of all the times I’ve been a participant on teams where the people in charge say they want to hear everyone’s ideas but their actions fail to foster it, and I think, I don’t want that, that is a failure in leadership. So now when different people are able to share their ideas, I feel like, yes, we must be doing something right. 

Wednesday, June 18, 2014

How “nerditude” leads to fulfilling work


"Isn’t that just nerditude?"

We were talking about why some people are good at developing their interests while others seem to lack that instinct. I believe this ability is an essential ingredient for finding fulfilling work and building great careers. 

This conversation was inspired by the Costco checkout line. We were waiting in line and noticed that this particular line had two employees managing checkout. The first person would rearrange all the items in our shopping carts so that all the barcodes were facing upwards and were easy to spot. The second person would use a barcode scanner to quickly scan all the items. How smart. It seemed to us that someone must have obsessed enough checkout processes to figure out that this simple division of labor would lead to faster checkout times. Some employee probably had a well developed interest in optimizing processes. 

We define “interests” broadly. It could be visiting every country in the world or figuring out algorithms to crack 2048 or cooking eggs at precise temperatures or observing human interaction with everyday things or thinking about issues like the end of print or replicating every molecular gastronomy recipe in the Alinea cookbook. An interest is a thing to which you devote exceptional attention. Not necessarily a lot of attention - it could be a fleeting interest - but there is a notion of wanting to really figure it out. In other words, we could call it “nerditude”.

The people who are good at developing their interests seem to:
- Believe that it is worthwhile to follow your curiosity
- Pursue that curiosity by delving into it
- Understand the nature of their interests and are able to incorporate some of them into their lives in fulfilling ways - as hobbies, as side projects, as enjoyable wastes of time, as elements of a career.  

The people who lack that instinct don’t seem to know what excites them. Is it that:
- They have never encountered things that truly excite them? 
- They haven’t developed that muscle to identify that feeling of interest? (Is it a muscle?)
- They don’t know how to go about furthering that interest so that it grows as a source of joy? 

And how can we move people from the second category to the first? 

As I talk to people about the careers side project, I’ve noticed that this seems to be one of the central themes - the people who are better at developing their interests find greater fulfillment in their work. 

Wednesday, June 11, 2014

John Green on your responsibility to the gift

Maybe they will notice how hard you worked, and maybe they won’t — and if they don’t notice, I know it’s frustrating. But, ultimately, that doesn’t change anything — because your responsibility is not to the people you’re making the gift for, but to the gift itself.

- John Green, author of The Fault in Our Stars and Looking for Alaska (via Brainpickings)

I really like that. Maybe that’s why John Green is so good at being gracious even when he has become a superstar of young adult fiction. 

I have been thinking about what is the gift. What does the gift want to be. What does it mean to serve the gift and share it.

Sunday, June 8, 2014

Getting unstuck (& working in public)


I’ve been stuck on the side project. I have these user interviews. I have all these notes and findings. I want the project to have this. And this. And this. I’ve even started working on the website… except that I don’t know what the product is. What am I making? What is this thing??

Yesterday afternoon while we were at one of our regular coffee spots, I just started to make myself write. For 3 hours, I wrote a lot of things. This is part of it:


I was browsing all these career advice sites and frankly it was a rather depressing way to spend my Saturday morning. None of my career transitions have ever been inspired by a career site, and yet here I am trying to build such a thing. How will it be different. They say you shouldn’t feel compelled to invent new business models when viable ones already exist. But I really want this to be about what I believe. I don’t want it to be about promising someone that they can land their dream job if they just follow 3 easy steps. This work - not this project, but the work of seeking career fulfillment - is hard. This project, in comparison, is easy. Except that I don’t know what the project is. Hmm. 

I’m at that point where I’m feeling the stones, as the expression goes. Feeling the stones to figure out what it is I’m looking for. In this phase, we speak in negatives. “I can tell you what it is not,” said a friend I interviewed who went on to describe her dream next role. (She landed it days after we spoke, isn’t that great.)

So it is not a career quiz where you answer 50 multiple choice questions and you’re told that you should be a teacher or naval engineer or singer. (This one quiz told me to be a singer. Righttt.) It is also not a long process where I help you overcome your fears and unleash your hidden powers. It is not therapy. I don’t want it to be a tactical thing where I tell you 10 tricks to make your resume stand out or 5 ways to ace that interview. I’ve employed creative tactics to land jobs before and I’m happy to share them, but it’s not what I really want to talk about. 

What I want to talk about is… discovery. Discovery of the self and discovery of possibilities.


And then I started to write about my own experience with career transitions. I ask it of everyone I interview, “Tell me about your path, describe your experience.” I call it the warm up question, but it is a strange experience to have to answer it myself. Where do I even start. Whichever way I describe it, it feels so incomplete. 

There is the short form:

I was in finance, then I switched to tech. 

But there is the longer form:

Government finance job
Hated it, went through a long, complicated, life-defining process to leave
Market risk finance job
Investment banking
Burn out and wish to save the world - whatever that means
A social impact phase
Made up my own internship with a global health non-profit
Business school, because I didn’t really know what else to do 
Social venture capital internship

And then I struggle to describe how it led to tech. I think it had to do with venture capital being really about startups, and then I read a ton about startups. At some point, I let go of the notion that I had to be employed to do finance type work, which I had assumed was my strongest selling point. I got it into my head that I wanted to be an operator. I cannot tell you why exactly I thought I’d enjoy it or be any good at it. But connecting the dots, I can trace it to my admiration for my father’s career. He is an operator.


Then just as I was about to write about how I got into product management, it hit me what I needed to do next.

I have been trying to define the minimum viable product, but I decided that I should actually go smaller - for a sub-minimum viable product. While I’ve been saying dream bigger, I also think I need to start smaller. So that I actually just start.

Out of nowhere - ok, I had been thinking about it for days, so maybe out of somewhere - I had this idea that it would just be a bunch of questions. I have this note titled “100 questions” and it is meant to be a list of open ended questions people ask themselves when they’re trying to figure out their career. The sub-MVP is basically that material turned into a product. 

Ok, I need to go work on the thing. But that’s where I’m at. I’m excited!

Tuesday, June 3, 2014

Discovery of interest


How do people find their careers. Specifically, how do people figure out that a particular job or company or career is interesting to them? I’m curious about the discovery of interest, because what I’m really trying to figure out is the reverse. If you don’t have a passion - as most of us don’t - how do you go about discovering your interests? 

These are the stories I’ve heard: 

"I met someone inspiring who does exactly that."

"I’ve always admired the work that they do."

"I realized that my favorite projects from my previous jobs had this in common, so it’s what I want to do next."

"I love their products as a consumer."

"I found myself reading about it in my free time anyway."

"I want to be more like the people I’ve learned about in that industry. I like how they see the world. That’s my tribe."

"I like the problems they’re solving."

"I grew up in a family with entrepreneurs [or doctors or even corporate managers], so it made sense to me to make a career of it."

"I’ve always been doing it kind of as a hobby, but I never thought I could turn it into a job."

"I started out volunteering, and as I got more involved, it turns out that there are organizations that do this. Then I realized I could do this for a career."

"It was a good fit for my skills, and since then the more I’ve learned about it, the more interested I’ve become." 

"I talked to a lot of people and I would gauge my reaction. Does what they’re describing intrigue me, excite me, bore me?" 

All of this is to say there is no magic formula. But exposure to people and ideas is good. Curiosity is good. Paying attention to what makes you buzz with excitement is good. Be open to inspiration. 

How did you become interested in what you do?