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.
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.
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.
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.
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
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!
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?
On crossing the Atlantic and the possibility of failure by chickening out
"But there’s an interesting thing about rowing an ocean. Essentially you are just a very expensive… cork, really, more or less at the mercy of the currents and the winds. An hour after leaving harbor… you can still see the harbor, but you cannot return to that harbor… It’s impossible to get that boat back to the start line. So the only possible thing you can do is just keep rowing 3,000 miles until you get to the other side of the ocean."
- Adventurer Alastair Humphreys, who did row across the Atlantic Ocean - and cycle around the world and cross major deserts and complete other macro and micro feats
Some of us might call that “terrifying”; Alastair Humphreys chose the word “liberating”. “Because it removes the possibility of failure,” he adds, “Well, I might as well just keep going to get to the other side.”
I have no wish to row across an ocean, and I do think that even if you remove the possibility of failure by chickening out, you still live with the possibility of the ocean deciding that you will fail.
But it got me thinking about all the scary things we do, and what if we could row just far out enough, beyond the reach of shore, so that you have no choice but to keep going, keep going until the ocean stops you - or you are carried by momentum and willpower and you make it all the way to the other side.
How people feel about work
"I believe that having a job you love is transformative."
"I just want to like going to work every day. Is that high or low expectations?"
"That job made me feel like a better person, because I had the resources to live generously."
These are the kinds of things people tell me in my user research interviews for the side project. When I’m doing the interviews, I’m too busy trying to listen and take notes and steer the conversation and give space. But later on, when I go back to the recording to make little sticky notes, these sentiments emerge. Maybe it’s just me and my deep fascination with how people relate to their work, but sometimes it makes me gasp. I just feel like, what a privilege to hear someone share that. What insight into their lives. Thank you so much for sharing that.
Thinking twice as big
"Your playing small does not serve the world. There’s nothing enlightening about shrinking so that other people won’t feel insecure around you.”
- Marianne Williamson (HT Brene Brown)
I’ve been working on the side project. First one in a very long time. What is the project about? It combines two things that I spend a lot of time thinking about - career advising and building products.
I wanted to say, “It combines two things that I love,” but I feel that these are two very odd things to love. They are not warm, fuzzy hobbies, like fly fishing or scrapbooking or train collecting. They are too strangely shaped and frankly can be rather frustrating ways to spend my time. Calling them “passions” sounds too over the top. It feels more appropriate to simply say that they are two things I really enjoy spending a lot of time working on.
Here is the challenge I am posing to myself. I don’t want it to just be a small side project. The problem with my side projects, I feel, is that while they have been successful, I have consistently thought too small. I have a tendency to think about a nice goal that has a very high chance of success, and then I just execute against it.
I am very good at the execution. I need to work on the dreaming.
My last side project was the Skillshare class - “How to land a job at a startup even if you can’t code”. The class sold out every single time. It received rave reviews. But I only taught it 3 times. I didn’t take it further, even though it could have grown in many interesting directions - more classes, an online version, guest blogging, an advice column, a consulting business. Who knows. The possibilities - that I never explored.
I want to approach this as a not-small side project. I don’t really know what that means, but I want to push myself to think bigger. I don’t want to get scared even if I can’t see the end in sight. If I like the way something sounds, I should ask myself, “What if you made it twice as big?”
P.S. If you’re in NYC and you’re working on a side project, you should totally apply for Gary Chou’s Orbital Bootcamp. It sounds awesome.
I made some sketches
I’m the kind of person who thinks in spreadsheets. Habit from my investment banking days. I mean, most things that pop into my head can be expressed in lists or tables - that can be sorted or pivoted or somehow rearranged.
At some point, I became more of a slides person, because some ideas have to be expressed - no, not as bullet points - but as shapes and spaces between shapes.
Lately, while working on the side project, sometimes I just can’t think in spreadsheets or slides or Evernotes anymore, and I need to get a pen out and draw. It’s refreshing. New medium, new thoughts.