My Career as a Series of Emails

I met with a new colleague at Notion last week and our conversation started with my career history. My half-joking summary is “falling ass-backwards into great opportunities over and over again.” My honest summary is “a series of events where I created luck for myself.”
I proceeded to rant for well over half an hour, waving my hands wildly in that conference room in true Italian-American fashion, and was given the advice to write this up. After spending a few minutes digging through my Gmail archive and smiling at old emails – I agreed.
This post is an honest chronicle of the job opportunities, mentorship, and negotiation benefits I’ve had exposure to in my career, told through the emails I sent and received.

🔗 ⌛ Asking for an update

In my junior year of college in January 2013, I started to aggressively look for an internship in San Francisco, a magical land full of people wearing Dropbox T-Shirts talking about Ruby on Rails. I was not necessarily convinced I’d spend the early years of my adult life there, but I wanted an SF startup on my resume. (Author’s note: in 2024 I no longer believe this is true and you should spend a summer in NYC because it’s better and has pizza).
This led to the following job application and email exchange with Obvious, the parent organization of a shiny new writing platform called Medium which at the time was still invite-only.

(Jan 2, 2013)

Thank you for applying to the Obvious Engineering Internship Program for the Summer of 2013.
I wanted to let you know that we've received your application successfully and have all the information we need at this time.
I'm sure you're wondering what the next steps are. We are currently accepting applications and in January 2013 we will begin evaluating candidates. You can expect to hear from us before the end of January.
Thanks again!
Four weeks later, after the end of January, I had not heard back. I had received four internship rejections from other companies (including the one I would work for after graduation), and thought it would be therapeutic to tease out a fifth.
I spent well over an hour writing, editing, deleting, re-writing the following one-sentence email to ask about the status of my application.

(Feb 6, 2013)

Hi [Redacted],
I just wanted to follow up with you regarding my application, as the month of January has now passed.
Kind regards,
Jordan Scales
A week later the following arrived in my inbox:

(Feb 13, 2013)

Hi Jordan,
Thanks for reaching out. We are actually still evaluating candidates (turns out it takes more time that you think!)
We have an open intern slot on a sizable backend project, and the mentor expressed interest in your experience.  Would you be interested in being considered for that team?
– [Redacted]

(Feb 13, 2013)

Hey [Redacted],
Thanks for the quick reply. That sounds very interesting and I'd love to hear more about it.
The very next day, I was included on another email thread with the mentor.

(Feb 14, 2013)

Hi Jordan,
I wanted to give you an update on your application to the Obvious Engineering Internship program for the summer for 2013.
[Redacted] (cc'd) has volunteered to evaluate your application and will be guiding the rest of your application process with Obvious.
(… Details about the process …)
Thank you,
A day later I received a PDF with a language-agnostic coding challenge. I submitted it that morning. 3 hours later I received another email to hop on Skype for what I thought would be a follow-up interview to discuss my solution. We scheduled this a few days into the future – giving me a few days to prep.
It ended up being a sell chat and an opportunity to ask the engineer (who would be my mentor) any questions I had about the internship. A few days after that the official offer came in.

(Feb 25, 2013)

Hi Jordan,
I'm very pleased to offer you a position at Obvious in our internship program for the summer of 2013.
Attached you'll find our offer letter to you and associated details. If you have any questions don't hesitate to ask!
To accept our offer simply print it out, sign the page at the end, then scan it and return it by email.
Congratulations and welcome!
I have many theories as to what transpired behind the scenes, but a quick “Hey can I get an update” is the reason I got this internship and, as you’ll read on, this internship led to more opportunities for me.

🔗 📜 Requesting a special interview

I had applied for an internship at Khan Academy twice while in college and was rejected both times at the resume screen. In November of 2013, armed with a coveted “SF Internship” diploma, I took a stab at a full-time position.
The phone screen consisted of a small JavaScript problem over Skype. I rushed through this and spent the remaining interview time expressing my admiration for Khan Academy and nerding out with the engineer about our shared interests.
In a series of follow-up emails, she included this snippet at the bottom.

(November 21, 2013)

Hey Jordan,
(… Details about the interview process and some links for things we discussed …)
Thanks again for reaching out, and feel free to ping me if you have any further questions! [Redacted]
P.S. - Did you see John's recent blogpost on project-based interviews at KA? http://ejohn.org/blog/project-based-interviews/

(November 21, 2013)

Awesome, thanks for the links :)
I did see John’s post earlier today (good timing!), and it was my first time hearing about project-based interviews at KA. Sounds like a pretty awesome idea - I may reach out to [Redacted] for some details on that track.
Anyway, thanks again for being super helpful,
The take-home project was being offered as an alternative to the traditional whiteboard interview which I wasn’t particularly good at. It was a perfect opportunity for me and I jumped on it by sending an email. In another thread with the recruiter:

(November 21, 2013)

Hi [Redacted],
One more thing: I was reading John’s post today on project-based interviews at KA (http://ejohn.org/blog/project-based-interviews/) and it looked really interesting. Is this something we could explore? Anyway, just interested in hearing more about it if possible - mostly out of curiosity.
Thanks again,

(November 22, 2013)

Hi Jordan,
Yes, we can definitely give you John's project-based interview if that is the route you'd like to take. Would you like me to set that up instead?
Please let me know if so, and I can send you the project-based interview if that's what you'd like.
A few days later I received the take home project, worked harder on it than all of my school projects combined, and hopped on a call with the guy who wrote jQuery to discuss it.
This interview went really well and (a) gave me the confidence I needed to go through the other interview loops (b) established a great working relationship for John and me. I’ll spare you (and John) the hero worship, but my time at Khan Academy was full of completely undeserved serendipity such as:
I often wonder what would have happened if I had not done the project interview with John.

🔗 💰 Leverage and signing bonuses

In late 2017, I found myself with a job offer thanks to a referral from a former colleague at Khan Academy – who serendipitously was also my lunch buddy when I visited the Khan Academy office for my final onsite.
The entries above focused mainly on making more luck for myself. In this section I’ll talk about a different kind of opportunity – the high-leverage situation you’ll find yourself in when a salary offer comes in.
I do not consider myself an expert on the topic of negotiation, but I wanted to share my experience because my past self would have found it useful. The first order of business is to read https://www.kalzumeus.com/2012/01/23/salary-negotiation/ and on your next walk, listen to https://www.kalzumeus.com/2016/06/03/kalzumeus-podcast-episode-12-salary-negotiation-with-josh-doody/.
A couple pull-quotes from this post which resonated with me
I decided to give it a shot.
Through sweaty palms, a heart rate of 120bpm, the fear that I was about to ruin everything (protip: you’re not going to ruin everything by negotiating your salary), I spent about an hour writing, deleting, and re-writing a single sentence at the bottom of my email to the recruiter.

(October 18, 2017)

Hi [Redacted],
I've looked over the offer letter and I have a couple questions when you have some time.
(… Some questions about the contract …)
Lastly, if the base compensation is non-negotiable, is there any flexibility in my RSUs or my signing bonus?
Thanks so much, and talk to you soon,

(October 18, 2017)

Hi Jordan!
(… Answers to some of my questions …)
As I mentioned on our call, we do come in with our best offer and since we're at the max for base compensation and RSUs there isn't any room for negotiation -- However, I was able to get you an additional $5k on the sign-on bonus! I hope this helps.
I cashed in my chips and signed.
To this day this is the fastest I’ve ever made $5,000.
There’s a lot of room for improvement here: that dollar amount could have been higher, or that money could have been added to my salary paying me every year and increasing with my regular salary increases, but I don’t think too hard about that. I think about how I went from +$0 to +$5,000 with a single sentence.
Try it.

🔗 📈 More negotiations

Fast forward to 2021. I find myself with another job offer, from another referral from another Khan Academy colleague (that place really churns out opportunity, huh), and another chance to try some negotiating.
Equipped with some experience, and some coaching from another former colleague who gave me the “would make me feel great” line, I upgraded a single sentence in an email to two paragraphs. Through sweaty palms, I churned out the following and went for a walk to calm myself down after hitting send (this shit is stressful).

(July 15, 2021)

Hi [Redacted],
(… Some questions about the contract …)
I've been number-crunching and soul-searching this afternoon and really like the offer Notion has given me, but would like to discuss the salary. A base pay of $X is a decrease from my last role and absent a signing bonus I am slightly hesitant to accept. Having factored in the commute (and the commuter perks), a base pay of $[X * 115%] would make me feel great and ready to sign.
If there is instead more flexibility in the options grant, an increase from the option to purchase X shares to around [X * 115%] shares would make me feel equally great - or of course a mixture of both.
Appreciate your helpfulness throughout this process, and look forward to chatting soon,

(July 15, 2021)

Hey Jordan,
Thank you very much for your thoughtful email! I am happy to begin working on this, but would like to discuss it quickly if you wouldn't mind. I know it is a bit late EST, but would you happen to have a couple minutes now? If not, I know you mentioned you are traveling tomorrow, but is it possible you have quick window of availability at some point? Happy to work around your schedule.
We hopped on a call the next day where I was asked, directly, “Will you accept this job if we accept your counter-offer?” I replied (honestly!) yes. I was given precisely what I had asked for, but had to decide if I wanted cash or options. The ~dollar amount was the same, but I liked the idea of the upside on the options and chose that (hindsight: this was a very, very good idea).
Because of this exercise I started this job on solid ground, feeling appreciated and wanted. As with the previous gig, there’s likely some opportunity for improvement here – a higher amount, more creative suggestions, making myself a tough sell – but I’m results oriented and the result was a 15% increase in my equity grant because I sent an email.

🔗 📬 Will you write me?

I had a lot of fun digging through my old emails to copy and paste into this post, and am forever grateful to those who received them and wrote back.
I wrote this post as a gift to my former self. With each email thread above are untold hours of frantic editing, doubting myself, and generally being stressed that I was being “annoying” or “difficult.” As you find yourself in front of an empty Compose Email… prompt, remember that yes this stress is awful, but should not keep you from creating your own luck.
If you enjoyed this post or found it useful, I’d love to hear about it – me@jordanscales.com.