I’m making a little cheat sheet for myself. As I progress in my career, much of my work revolves around communication, and I’d be remiss if I don’t share a formal framework I use. I like checklists, spreadsheets, and anything else that organizes the world around me, and it’s fun to make one about communications.

Checklist

This is a checklist for high stakes emails, let’s dig in:

• Goals
  • What are you trying to accomplish? Why? (It could be worth asking why multiple times.)
  • Will this email help you accomplish the goal?
  • Can the goal be summarized in a single sentence? If not, it’s probably not specific enough.
• Audience
  • Who is the audience?
  • What does the audience care about? How can you connect the subject of your email to things they care about?
  • Does every recipient need to be there? Who’s missing?
  • What action do you want the reader to take? Is there a clear call for action? For executive communications (who have notoriously short attention span), you’ll want to both start and end with the same call for action.
• Content
  • Is there a nuance that would be lost in email that requires face to face conversation? Does this need to be an email?
  • Does every sentence and paragraph support your goal?
  • Does this need a TL;DR?
  • Is the narrative structure in place? Is there a clear beginning, middle, and end? No need to write a novel, but without this the content risks being disjoined.
• Impulse
  • Is now the best time to send it? Friday afternoon is almost always a no-no, unless you purposely want the reader to pay less attention to the issue.
  • If this was shared broadly, would you rephrase it? If yes - you definitely should.
    • To double down, if email is about someone, write as if that someone will eventually see it. It’s fine to be candid, it’s not fine to be rude.
  • Are you angry? Upset? I get notoriously cranky in the late afternoon, and avoid sending anything important until the next day - or, if time sensitive, until taking a short break or a walk.

Example

Let’s apply this to an example. Say, I’m writing a book, and the editor I’m working with hasn’t been responsive. I’ve tried talking to them about it, but they’re not responsive. I think it’s the time to escalate to their supervisor.

Here’s the quick, dirty, and impulsive draft I would write:

Hello X,

Y hasn’t been responsive when reviewing the chapters, and it’s really difficult to get back to chapters after a whole week passes by. By then I don’t even have the context! I’ve raised this multiple times and to no avail. Can you please get Y to be more responsive or find another editor for me to work with? I haven’t been able to make meaningful progress in a month!

Pretty brusque, isn’t it? I don’t normally dissect every email like this, but sometimes it helps to take a closer look and formalize the decision making behind each sentence. Thankfully, much of this becomes habitual over time.

Goals

First things first, I want the editor to be more responsive. Why? To have a shorter feedback loop when it comes to making changes. Why? To make it easier to write - it’s difficult to come back to the chapter after a long amount of time passed. Why? This pushes back timelines for each chapter.

I don’t really care about how to achieve this goal: the same person can be more responsive, or maybe I get a new point of contact to work with. Maybe there are other options I haven’t considered.

To summarize in a single sentence, the goal is to “reduce the feedback loop”.

Audience

The audience is the editor’s supervisor, or maybe someone else from the editorial team who’ll have the incentive to escalate.

I know that the timelines are very important to this publisher, which is something I can use. I can frame the concerns around impacts of the timeline - even if it’s not something I necessarily care about myself.

Since there are multiple ways to achieve my goal and I don’t particularly care about how, I can make the call for action open ended. I’m doing this because I’m comfortable with either outcomes - like the editor not being to improve response times, but the publisher providing more leniency around the schedule - which, while isn’t ideal, still helps.

Content

As multiple people can help me accomplish a goal, and I might not be aware of all of relevant parties - email format works best.

Narrative structure here is simple - I have a problem (the beginning), here’s why it’s bad (the middle), let’s fix it (the end).

This email is short enough not to require a TL;DR.

Impulse

As my concern is about a particular person, I have to talk about them. I don’t want to avoid candor, but I can approach the situation with empathy and assumption of best intentions something along the lines of: “I understand X has other commitments”. Focusing on facts and leading with empathy would help here.

Having an unresponsive editor is definitely frustrating, so it’s worth taking a step back, and maybe paying extra attention - there’s no use having frustration show through.

The result

After running through the checklist, we end up with (what I hope is) a better, more actionable, and less icky email:

Hello X,

When working with Y, it takes up to a week for me to receive feedback on the chapters I wrote. I understand Y is working with multiple engagements, but I’m concerned about the timelines for the book. If we continue as is, it’s likely we’ll have to push publishing date by X months.

Could you help me find a resolution here?

It’s short, omits unnecessary details, and leaves the reader with a clear (but open ended) call for action. Now, all that’s left is to schedule send that email in a morning, and wait for a response!

Following Europe’s 2016 General Data Protection Regulation (GDPR), California passed its own California Consumer Privacy Act (CCPA) in 2020. I won’t pretend to understand the intricacies of the law or the differences between the two, but from what I understand this gives you the right to know exactly what data of yours do businesses use, and request that this information is to not be sold or to be deleted.

As a California resident, I decided to dedicate a long weekend to exercising my privacy rights. The long weekend turned into a week worth of back and forth with a dozen-or-so companies, and me having a much better idea of what information about me is out there.

Turned out many large websites provide privacy dashboards where you’re able to review and see information collected or inferred about you. But most of this data is hidden behind a formal request process which takes a few days to a week.

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First, I decided to stroll through Google’s privacy settings. There are two ways forward: privacy dashboard, or full-on Google Takeout. Google Takeout allows you to download an archive of everything Google has on you, which took a few days to process, and is near impossible to go through while keeping your sanity. So I decided to play with the privacy dashboard instead.

Google Maps has location history of most places I’ve visited for the past ten or so years (creepy, but I found it useful on more than one occasion), and YouTube and Search history stores thousands of searches. I already had Assistant history disabled, since storing audio recordings is apparently where I draw the line when it comes to privacy. Targeted ad profile was an interesting thing to look at, accurately summing up my lifestyle in 50 words or less. I ended up disabling targeted ads from Google (and all other services as I went about on my privacy crusade).

Google had some of the finest privacy controls compared to other services, with actionable privacy-leaning suggestions. Google’s not known for its services playing well together, but privacy is where Google feels closer to Apple experience - everything is in a single place, surfaced in the same format, easy to control, and plays well together. Given the amount of transparency and fine grained control, I feel pretty good staying in the Google ecosystem.

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Next I looked at LinkedIn. Outside of the expected things – emails, phone numbers, messages, invitations, and a history of just about everything I’ve ever clicked on, a file labeled “inferences” stood out. Whether LinkedIn thinks you’re open to job seeking opportunities, or what stage of career you are in, or if you travel for businesses, or if you’re a recruiter or maybe a senior leader in your company.

Since LinkedIn is a professional network, all information I share is well curated and is meant as public by default – and I found LinkedIn privacy settings in line with my expectations.

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As an avid gamer, I went through Steam, Good Old Games, Ubisoft, Epic Games, and Origin privacy details. Unsurprisingly, the services tracked every time I launched every game, shopping preferences, and so on. Thankfully the data seemed confined to the world of gaming – which made this level of being creepy somewhat okay in my book.

I also looked at random websites I use somewhat frequently – Reddit, StackOverflow, PayPal, Venmo, AirBnB, and some others – not too many surprises there, although I did end up tightening privacy settings and opting out of personal data sharing and ad tracking for every service.

Last year I requested deletion of all my data on Mint, Personal Capital, and YNAB (You Need a Budget), and to be honest I’m a little relived that I didn’t have to look at the data these companies had on me.

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Amazon data sharing turned out to be the scariest finding. Until now I didn’t really self-identify as a heavy Amazon user, but that turned out to be a lie: Prime shopping, Kindle, Audible, Prime Video.

The amount of data Amazon kept on me was overwhelming: Kindle and Audible track every time I read, play, or pause books, the Amazon website keeps full track of browsing habits, and Prime Video has detailed watch times and history. Most of this data ties back into real world – including nearly every address I ever lived at or phone numbers I had.

Even scarier, despite never using Alexa, I found numerous recordings of my voice from close to a decade ago – me checking status of the packages, but a few of me just breathing and walking around. I found no way of deleting these, as they didn’t show up in any privacy settings (including me installing an Alexa app just to get into privacy settings).

All of this gave me pause. It feels like the privacy controls are either lacking, hidden, or spread out thin across Amazon’s various apps. And I’ve only briefly scanned through the data Amazon had on me.

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That’s where I had to take a break.

I have accounts with hundreds of services, and I have no idea how my personal data is used, and what it’s joined with. As I’m go on about my daily life, I’ll start tightening privacy controls, and maybe deleting services and their data where possible.

It’s just too creepy for my taste.

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While you have control over the services you have accounts for, companies and ISPs collect a trove of private information on you even while you’re not logged in. For that, I strongly recommend using a VPN. I’ve been using PIA since 2019 and I’ve been very happy with it. Wholeheartedly recommend.

As I’m starting to write more about early retirement, I think more and more about financial planners and advisors I’ve talked to along the way. The first financial planner I ever talked to (who’s been now fired from a role of my financial advisor and promoted into a position of friendship) reminded me about the beginning of the journey after reading one of the FIRE articles I’ve posted earlier this month.

I’ve talked to half a dozen financial planners over the past 5-or-so years. Some of those conversations have been very influential, and some have been more aggravating than anything else – but it was a net positive experience for me.

The aforementioned financial advisor I’ve had the pleasure to talk to was a colleague’s spouse. I’ve voiced my interest in early retirement, and we decided to sit down and run through a financial overview.

I’ve learned a lot from this meeting, and the advisor helped me frame my knowledge, and fill in the gaps for everything I’ve learned on the Internets. The biggest value came from leveraging tax-advantaged accounts and employment benefits: maximizing 401(k), IRA, and HSA contributions, leveraging IRA backdoor and 401(k) megabackdoor (I just talked about these in detail in “Accessing retirement funds early”). We discussed fund selections, risk profiles, and even touched on housing. It was great to have an opportunity to have someone who knows what they’re talking about answer all the questions that built up over the years.

The conversation had profound impact on my initial portfolio and investment strategy, and set pace for early retirement planning. With the confidence of having my plan and assumptions validated, I went on with my investments (employing the “slow, boring and steady” strategy, if you’re interested).

After some time said colleague and his spouse became our family friends: and I don’t much care for doing business with friends.

After that experience, I struggled to find the person I would work with for a prolonged amount of time.

At some point I thought I found “my guy”: a financial planner who was familiar with early retirement, and was eager to do additional research for just about any topic I could ask. Unfortunately for me it didn’t take long for “my guy” to soar through corporate ranks and get promoted past working with individual clients.

This is where the cracks started to show. For many financial planners, early retirement refers to age 55. And that makes sense – retirement in your 30s is such a niche topic! Most financial planning tools don’t account for this. Things like tapping into 401(k) or IRA balances before age 59 1/2 is not something supported by the rigid financial projection tooling.

Your typical financial planner will not be intimately familiar with the intricacies of early retirement – or any other niche topics for that matter. And that’s okay. Because financial professionals still know their shit – and it’s much easier for them to make professional judgement about things your smart ass found online.

The best financial planners I talked to were willing to listen and put in work outside of our calls. Those folks would understand my concerns, supplement their answers with research, and come back with educated opinions.

A model that works for me is providing my questions and concerns in advance of the call, giving the advisor time to research niche and domain specific questions.

Financial planners worked for me especially well for two purposes:

1. Confirm that my understanding of something is correct.
2. Tell me about things I don’t know or haven’t thought about.

This is where a financial planner pointed out that I misunderstood 401(k) contribution limits, or didn’t consider implications of varied cost of health insurance in retirement. This is the person I bombarded with an hour worth of questions about my auto insurance or the need for umbrella policy.

One time fee advisors worked best for me. I know some folks who moved assets under management for a certain percentage of those assets in fees, and are now trying to get out. This worked okay for them early on, but ended up not being what they want as they became more financially savvy. And it turned out to be oh-so-expensive in the long run.

And there are many things I had to watch out for along the road. Some advisors I’ve talked to seem to have no idea what they’re talking about, and just sound misguided. And it’s not solely my opinion - sometimes I would write down something a person would say, ask for independent opinion, and get back “What drugs are they on? I would like some of that!”

There’s also the question of their interest.

Some financial advisors might be inclined to sell things like lucrative whole term life insurance, and while in certain cases it’s appropriate, it might not always work for all individuals. But it sure as hell pays well for those advisors, so it’s hard to fault them for peddling the insurance.

The United States has a fiduciary system that’s supposedly requires a planner to work in your best interest (I personally learned about it from this Last Week Tonight show episode).

If you’ve done a lot of your own research (and especially if you haven’t) – it certainly wouldn’t hurt to talk to professional and review your decisions. Someone who has an idea of what they’re doing can go a long way in making sure you’re not heading down the wrong path – and if you are – you’re doing it with full awareness of the trade offs you’re making. Just be mindful of pitfalls when doing so.

When writing about snippets at Google earlier this week, I omitted a fairly important bit: how lists and journaling help me create distance between work and life. This became especially relevant in the pandemic, as I had to work with my therapist on being able to mentally disconnect.

I wrote about my strained relationship with ToDo lists before: all the way back in 2014. Back then I focused on moving away from a monolithic ToDo list, and focusing on just a few major things I’d like to accomplish each day. I continued to do this, but with some changes to my philosophy.

I’m back to keeping a ToDo list, but it’s a bit more complex than a single list I used to keep. I split things I care about by days, weeks, and months, and I review these lists regularly.

Last year I learned about bullet journaling, often shortened to “BuJo”. Akin to artisan coffee and avocado toast, this hipster friendly and highly marketable approach has a solid foundation. At its core bullet journaling consists of two parts. First is a consistent and simple notation for tasks, notes, and events: some simple guidelines on how to document what happened, what will happen, and what you need to remember. Second part is a rule set on organizing these lists: daily and monthly notes, custom logs, and so on.

I rigorously keep daily notes about work, meeting annotations, records of important thoughts and ideas, and things I need to do (or have already done). This helps me leave work at work – or more precisely leave work in a journal. Once it’s closed - I’m done for the day. Everything I need to think about is written down, and there’s no need for my mind to wonder back.

Some weeks I omit note taking, and the contrast in my well-being is jarring. My mind wonders back to the events of the week, and I even have trouble sleeping some days. And no one wants to dream about work – I’m sure as hell not paid enough for that.

Another technique I picked up from the bullet journal keeps me from getting overwhelmed and keeping focus. BuJo advocates for regular migration of ToDo items – meaning that you should be crossing out and rewriting the same thing over and over again, day by day, week by week. At some point it becomes either to either do something about those ToDos, or choose not to do them altogether. Either way, it’s a huge weight off my shoulders.

And this is where the aforementioned snippets come in. At the end of the week, all I have to do is go through the weekly set of notes, and transcribe noteworthy bullet points. That’s the time I take to look back at my week, migrate tasks I choose to revisit at a later date, or cross off tasks I choose not to do.

I’ve learned a lot of cool things during my tenure at Google.

One of those things are snippets. Google (and from what I hear other Silicon Valley giants as well) utilizes a system of snippets: a transparent and widely accessible set of weekly notes. It’s not mandatory, and some groups use it more often then others. Sounds ordinary, but I think it’s a lot more interesting then that.

Communication and visibility is one of the major challenges in any paid creative work, but it’s especially important in software engineering. Engineers often settle on tasks they know nothing about: tasks are hard to measure and estimate. This makes it even harder to communicate progress broadly.

There are ways around this communication barrier – regular standups or periodic reviews come to mind. But there’s a better (although not necessarily exclusive), more asynchronous way to communicate and increase visibility. Enter snippets - a condensed list of what happened with you and your colleagues last week, delivered straight to your inbox.

Every Friday, an email notification reminds you to fill in weekly snippets. These snippets might look something like this:

• Project X
  • Authored a design doc (link), sent for a review
  • Discussed roadmap with stakeholders A and B (notes)
  • Debugged issue Z, to no avail (link)
• Project Y
  • Cleared backlog for the past 6 months
• Attended a summit about G
• Had 1:1s with C, D, E, and F

On Monday, an email goes out compiling our team’s snippets in a single digest. Skimming through snippets covers any communication gaps from the past week, and raises visibility on what everyone is working on.

This system has many benefits:

• Transparency: you know what everyone around you (including higher ups) is up to.
• You actually remember what you’ve done a month from now.
• All the important documents, events, and notes are linked from snippets. Snippets are are time bound, which makes these documents easy to find.
• Teammates and managers can always check snippets to get an idea of progress on certain efforts.
• You manager (who’s hopefully your biggest ally when it comes to career development) has a great idea of what you’re up to.
• It’s easy to find artifacts and proof during performance reviews.
• Higher visibility of glue work (all the little things you do to keep the place running).

This doesn’t have to be a particularly complex system. A running doc with notes could suffice, although email notifications remove a lot of the overhead needed. Even if the organization doesn’t follow the model, I find it worthwhile to keep snippets, and to share them with my manager and team.