Achieving difficult goals usually requires thinking in systems. Processes over results. Execute an optimal plan for long enough, and you’re likely to accomplish The Thing.

Productivity nerds internalize Systems Are Good and Goals Are Bad to the extreme. These losers often have no idea they’ve done so until they wake up months later realizing their system has lulled them into an autopilot trance. They’ve forgotten the entire purpose their system was created for.

I know this to be true because I am one of those losers.

As a devout 80/20er I’m usually one to simplify. If Andrew Huberman spends 2 hours and 32 minutes yapping about optimal protein dosage, frequency, and delivery method, I’m asking Gemini to summarize the video. And then I’m still ignoring anything that comes with a behavior cost unless it offers an outsized return on my effort investment.

absorb(hubermanPodcast) only while benefitToMe > effortRequired

The process breaks without the condition. Listening to endless hours of scientific research that I’m going to forget 1.5 meaningful life events later is not what I want to spend hours of my AirPods battery life on.

Systems almost always require end conditions to be useful. There are very few specific things you should want to repeat for the rest of your life.

Take exercise.

Exercising for the rest of your life is a win. But you probably don’t want to be following the identical exercise routine for eternity. Instead, you probably want to schedule in some variation, or at least difficulty adjustments ala progressive overload to avoid freezing progress.

Not too long ago I realized I had been adhering to the same calorie goal for nearly a year without a second thought.

eat(2000 calories) is a reasonable goal.

repeat while weight > 185lbs: eat(2000 calories) is a better system.

Few systems within your business will last months, let alone years, without needing to be updated in response to change. Change in software, personnel, or market conditions. Now more than ever, we know it’s inevitable.

In practice this means assigning expiration dates to SOPs and best practices. An outdated process is worse than useless: it plants a seed of doubt in your entire library of company documentation.

If this doc is wrong, how can I trust any doc?

In startups this concept can apply to roles too. It’s worth revisiting if you have the right people in the right chairs on a semi-regular basis.

Treat your decisions as ongoing responsibilities. Deciding something forever is rarely optimal. Make your decisions inside while loops to keep your systems from taking you too far off course.

When I want to be healthy, I police my environment.

No chocolate, liquid calories, nor bakery items can be within walking distance of my desk unless they’re being guarded by a series of social interactions and financial consequences.

Avoid the temptations of glazed donuts and pavlova cake long enough and you start realizing that you feel better without it. Personally, this is the exact moment I typically like to let my monkey brain take the wheel.

I don’t cheat my diet by sneaking an Oreo and choosing not to log its 55 calories. I quickly identify and procure the densest sources of carbohydrates within a 5km radius of my apartment and pay several strangers to simultaneously deliver them to me as fast as possible.

The best part of this glorious feast? The moment I pull up a chair to my kitchen table, covered in a full spread of all the flavors I could ask for. My satisfaction levels dip the moment I take my first bite.

I was scammed by desire. I believed that I could relieve my wanting by giving into its demands. I believed that the wanting would go away if only I gave it what it asked for.

Today it’s a dozen plain Krispy Kremes. Tomorrow it’s whatever new product Apple releases. Next week it’s something, anything, that’s 65% off for a limited time only. Wanting never ends.

Sustaining habits may become significantly easier once we can reframe wanting from something that requires action, to something that requires acceptance.

I wouldn’t know. I love Krispy Kreme.

Knowing things makes me feel smart.

But learning can also be a trap, because knowing more things often isn't necessary to progress towards your life goals.

The moment you've learned enough to get from where you are now, to where you want to be, is the moment when knowledge is no longer bottlenecking your success.

Every cliché piece of life advice you've ever heard provides enough bite-sized wisdom to legitimately change your life:

• Exercise regularly

• Save your money

• Upskill often

And yet we'll listen to a 2 hour podcast on the best time of day to slurp back our protein shake before we reach 6 months of consistent exercise.

The fear and hesitation that paralyze us when we imagine taking action towards our goals is conveniently misinterpreted as "I don't know how to".

It makes us feel smart to sink hours, days, weeks, months, and years into accumulating information. The value of the next tweet, blog post, or podcast we consume is irrelevant. We just like the feeling of novel information entering our brain and massaging our neurons.

Learning is useful for finding out which actions and routines are required to achieve your goal. After that point, it's probably a distraction.

One of the best career decisions I've made over the past decade is saving up a large cash position to allow me to take on more career risk.

I've been extremely privileged to have worked at every job I've ever held. Save for a few pre-teen years where I quickly realized physical labor was not what I wanted to be doing, I've always worked remotely.

Better yet, every single job I've worked has allowed me to set my own hours within reason (at worst) or been completely async (at best).

Trying to sculpt work you like into a job you love isn't easy.

Asking for a raise is scary. Asking not to be included in meetings anymore is scary. No matter how much value you're able to deliver, these non-traditional asks are often new territory for even the most understanding and progressive bosses.

Managing employees is difficult. I respect that. But early on in my "career"(probably during high school, when I hard committed to working online) I decided that I wasn't going to settle for jobs that didn't afford me control over how and when I work.

My work life has been 100% async for the past ~5 years and I don't think I can ever go back. Naturally, this makes finding work 10x more difficult.

That's where the unemployment fund comes in.

The unemployment fund exists to buy me time and courage. It affords me X months of fully covered lifestyle expenses, so I can risk losing a good job when I'm trying to find a great job.

It would have my back if I were to wake up tomorrow to an email from my boss, informing me of a new company-wide initiative to have a daily standup call. Or if budget cuts butchered my effective hourly rate.

When your life is prepaid 6 months/9 months/12 months++ in advance, you have the option to be bold and ask for the things you really want.

Is it still scary? Yes.

Does it suck if you don't get the outcome you want? Yes.

Watching your unemployment fund burn down as you email founders to ask them if they'd be open to an async work environment is about as fun as chewing sand.

I want to form longterm relationships with people who not only appreciate the quality of my work, but who get excited about watching me level up while I'm doing it, on my own schedule.

The unemployment fund, miraculously, has allowed me to pass up on good jobs that check most of my boxes to pursue great ones that check them all.

It often takes me several attempts to finally scratch off goals I've set for myself.

Learning Spanish is a current example. For 2 years straight, I've told myself that I'd be fluent in Spanish by Christmas time.

The culprit responsible for delaying mi celebración is no stranger: irrational overconfidence in my ability to juggle multiple medium-sized habits at once.

I've made tons of progress over that timeframe. I can watch some Spanish movies and TV shows and more or less understand what's going on.

But I've yet to cross the finish line, and that drives me crazy.

What helps me collect myself and bounce back stronger is the understanding that I'm not uniquely unqualified to learn Spanish.

There's nothing hardwired in my genetic makeup making it harder to acquire this skill. Like almost any other skill, success is inevitable if consistency is maintained over a long enough timeframe.

If I do what my goals require from me, for a long enough period of time, I'll end up at the finish line.

I have stayed in 31 different cities across 11 countries over the past 5 years. I travel light and try to stay places for at least 1 month or longer.

At least once per year I try to ask myself if living nomadically is something I still want to be doing. Like any other major life decision I make, I want the decision to travel to be an intentional one.

How I feel about being a nomad has changed.

The stories and experiences I've collected while getting lost in these once foreign countries have numbed my ability to feel culture shock.

The dopamine buffet I'd feast on while eating up new cultural experiences in a new city has progressively faded into the occasional "oh, that's different" observation.

Crossing a busy street without a crosswalk, eating street food, and butchering the local language used to give me a rush. Now it's a typical Thursday.

I know there's still an unlimited supply of novelty patiently waiting for me beyond the borders of my comfort zone; I just don't accidentally bump into it during day-to-day life as often as I used to.

In this way, the reason why I travel has changed.

I used to travel because I wanted to experience more of the world. I still like how romantic that sentence reads, but I'd be lying if I said the constant pursuit of vacation-worthy experiences hasn't let me craving more routine comforts.

I want to own my bed sheets and have a favorite coffee mug. I want to have access to blender for protein shakes, a bulky electric toothbrush, and an air fryer for when I pretend I'm going to order delivery food less often.

At this stage in my life, I'm seeking locations that accommodate my vision of a perfect day.

Practically speaking this means spending most of the year within the same 1-2 shortlisted locations. Establishing home bases for living most of the year, leaving room for spontaneous vacations to chase novelty when I feel like exploring again.

🛒

The shopping list for my ideal home base:

Large desk
Comfy chair
Step-on garbage bins
Great lighting and good view
My own bed sheets & towels
Kettle, air fryer, electric toothbrush
Gym within walking distance
Groceries within walking distance
2 good cafes within walking distance
Diverse variety of food and people nearby

This may be the final stage of nomadism. The gradual transition from weekly trips, to monthly trips, to having established home bases is a familiar pattern.

Every meaningful working relationship I've created to date has been the result of a cold email or cold DM.

Before I had any experience working online whatsoever, it was sending cold DMs on vBulletin forums that opened the door for me to forge a career without any degrees or certifications.

Cold outreach can change your life by creating friendships, landing jobs, or simply receiving advice. There are few low-hanging fruit opportunities with this much upside. I'm realizing as I write this that I'm not doing enough proactive cold outreach.

I can't tell you whether my cold outreach technique is good or not, but it has landed me incredible working opportunities and connected me with amazing people who would have never known who I was otherwise.

This is how I approach personal cold outreach.

I don't try to influence or persuade. My objective is to present myself and my situation as authentically as possible. The recipient is free to decide whether or not they want to get involved once all the facts are on the table.

I completely avoid candy coating. I want to be as honest as possible by clearly expressing what I need from them, why I want it, and what's in it for them.

I explain why I'm contacting them instead of somebody else. This separates my message from spray and pray spammers who don't show a personal interest. It makes clear that they have a unique ability to help me.

I share how the opportunity fits into my bigger picture. Explaining how I will benefit from their help, and where exactly it will take me, helps paint a picture of the positive impact they can have on my life, if they decide to give me a chance.

I explain why they will benefit from helping or hiring me. Successful people (usually) love to help people hungry to succeed. If you're hungry and you can build a strong case as to why they would benefit from hiring you, everybody wins.

Your success rate on cold emails is dependent on your ability to authentically present yourself, meaningfully connect with the recipient, and craft convincing win-win situations.

I have likely sent less than 50 cold emails in my lifetime—and I'm conflicted about this. More outreach would lead to more opportunities. But I kind of like having this skill, which sometimes feels like a superpower, in my back pocket for only the opportunities I really, really want.

From day 1 of working online, I've been paid to write. I understand the concept of cold outreach may be more intimidating for those without a writing background.

Your message needs to standout if you want a positive response. If you don't have the writing ability to standout via email or DM, you need to get creative and/or work harder to capture attention.

I've been lucky enough not to need to resort to the more creative tactics, so I'll save my thoughts on those until I try them for myself.

I'll end this post with what I believe to be the best reason to do cold outreach: landing your dream remote job.

This is the advice I give most often to friends toying with the idea of getting a (new) remote job:

• Make a list of 3-5 people or companies you'd love to work for

• Find out how you can help them by looking at their past job postings

• Craft a convincing case on why you're the perfect person for the job

If you're not qualified, ask them if that's even an issue first. Ambition can sometimes make up for lack of experience.

If your lack of experience turns out to be a dealbreaker, share with them a 90 day gameplan you're going to follow to become drastically more qualified. Then ask them if your gameplan is missing anything important.

Execute the gameplan and email them again in 90 days or less.

The jobs/gigs/clients you will land by being proactive on cold outreach like this are 100x more rewarding than the stale opportunities you'll find on remote job boards.

And that's how I've created a career, with zero qualifications, out of cold outreach and working hard.

The start of the pandemic ruined everything.

With my first taste of solo travel still fresh on my tongue, I was forced to pack my bags and return home from Vietnam, only the third country I had lugged my backpack to since making my first long-haul flight from Toronto.

What followed was a serious case of the post-travel blues. I had just been 8,474 miles out of my comfort zone and now I was being abruptly yanked back into the mundane routines I so badly wanted to escape in the first place.

On the bright side, I'd have a lot of time at my disposal: my city was among those with the world's longest COVID-19 lockdowns. I made a decision early on, way before we really knew how long the pandemic would last for, that I was going to do everything I could to make the most of my time under lockdown.

Learning a Second Language

I'll never forget how I was treated when I landed back in Canada. The pandemic was finally hitting peak news coverage in North America, though Asia had been on top of it for months prior. Airport security was visibly startled that I was wearing a mask. Masks were a requirement to leave the house in Vietnam, but they were still completely foreign back home in Canada.

The government mandated 14-day quarantine for new arrivals banished me to basement apartment I found on Airbnb and left my wallet $1,400 lighter. I installed Duolingo on a whim, hoping that productive exposure to a foreign culture would scratch my travel itch. I had no plans of learning a language to fluency.

The beauty of Duolingo is its mastery of gamification lulls you into believing you open the app to learn a language, not to get your hit of dopamine from the pretty colors and rewarding sounds triggered by submitting correct answers and building your streak. But this is a good thing—it's the latter that leads to the former.

The hardest part of any productive habit is getting started. Duolingo is incredible at dangling a carrot at just the right height above your nose, forcing you to exert just the right amount of effort, gradually leading you towards a larger vocabulary and a real sense of progress. I was seriously proud of myself once I knew how to say 10-15 new phrases in my target language by memory.

These quick wins supplied by Duolingo manufactured my desire to really learn a language, something I never thought was possible prior to installing the app out of boredom.

At that point, not having spoken to a native speaker yet, I figured I needed to break free from the hypnotic drip of dopamine being supplied by Duolingo and actually practice speaking. This terrified me, but after some convincing from a friend, I knew it was necessary. And that's when I signed up for a private class on Italki.

Scheduling 1 class every week on Italki gave me someone to try and impress. What started as doing simple exercises and reviewing my mistakes became a weekly catchup call with a friend from the other side of the world. I started spending even more time grinding on Duolingo, hoping I'd master new words my language tutor on Italki wouldn't expect me to know already.

I stumbled on the Tandem language exchange app somewhere around the 30-40 class milestone. Tandem gives you access to native speakers of your target language who are studying your native language. I went from speaking with 1 native speaker to speaking with dozens, overnight.

I cringe when I look back on these chat logs now: my choice of words are consistently too formal, my grammar is suspect, and my phrasing is awkward—but I'm speaking a foreign language and being understood.

This combination of Duolingo, Italki, and Tandem brought me to the tipping point of language learning: being able to sufficiently understand native media.

According to modern language learning theory, you don't learn a language, you acquire a language via prolonged exposure. The ability to understand native media—movies, TV shows, or YouTube videos—puts language learning on autopilot.

By the time lockdowns were being phased out and borders were being opened again, I had reached the early stages of conversational fluency in my target language. A little part of me still doubted that strangers on the streets would understand me to the same degree that strangers on the internet did.

I was 1.5 years into studying my target language from my home country, a little less than an hour per day, when I found enough courage to speak to someone at the airport. They understood me! And I understood them! I had built a strong base of vocabulary and was able to express myself (in a basic way) to people who could not speak English. But there was still more work to be done.

I might have earned the proverbial 'basic conversational fluency' badge at this point, but there were gaps in my knowledge. Here's a story of when one of those gaps revealed themselves:

When learning a new language, it’s typically wise to focus on learning the words that occur most frequently in casual conversation. You may go weeks without saying “obstruction” yet the words “almost” or “because” could be spoken dozens of times every day.

“Cross” is not a word I had ever needed to use in conversation until this past week. It turns out that it’s very difficult to ask “how do I cross this street?” when you don’t know how to say “cross”.

"I want to go there", while pointing at nothingness across the street, does not work. "How do I get from here to there" is slightly better, but I didn’t think of it until after. I had to accept failure and pull out Google Translate for this one.

Living in the country where my target language is spoken has gone a long way in filling these gaps and training me to speak in a way that sounds more natural to native speakers. For example, imagine greeting someone with "has anything changed with you?" versus "what's new?"—both ask roughly the same thing, but the latter is just... weird. There were (and still are) plenty of small adjustments like that to be made.

Self-study took me 65% of the way to conversational fluency. Living in the country for almost a full calendar year has brought me to 75%. Now I have friends who can't speak English, and others who do, but still prefer to speak their native language with me. It's been an immensely rewarding challenge that I never planned on taking on until I installed Duolingo out of boredom.

As proficiency increases, gains are harder and harder to make. The path forward is slow: more exposure, more learning via osmosis. Since I don't plan on using this language professionally, I have no intention to reach advanced fluency. But I am looking forward to applying what I learned this time around to try and acquire a third language before the end of 2023.

You won't get rich renting out your time. This concept is repeated in every book about business, entrepreneurship, and financial success.

And still, instead of taking a leap of faith to embody these essential truths of entrepreneurship, I find myself more likely to reach for Another Book, hoping it will reveal a secret loophole to success.

🔖

The three most harmful addictions are heroin, carbohydrates, and a monthly salary. - Nassim Taleb 

My name is Jamie, and I might be addicted to a semi-regular paycheck.

I'm generally comfortable with financial risk:

• I've earned an income freelancing far longer than I've collected fixed paychecks

• If a client can no longer work within the conditions that allow me to produce my best work, I typically part ways as soon as possible  

• I optimize my work life towards my lifestyle instead of optimizing my lifestyle to my work. In practical terms, this means I don't work anywhere near 40 hrs/week

I'm proud of what I've achieved working online, evolving from a curious writer producing keyword stuffed articles for SEO marketers, to writing email copy that makes me laugh for trendy ecommerce brands. The number next to the dollar sign on my invoices has grown along with my confidence and ability, but still I find myself unsatisfied.

Given the choice between doubling my freelancing income, or adding a much smaller income stream that has no direct correlation to the amount of time it steals from my weekday—I'd choose the latter.

In my ideal reality, my income is primarily derived from the results of yesterday. Jack Butcher would call this Build Once, Sell Twice.    

I knew about this concept before discovering Jack Butcher. This same idea has been repackaged dozens of times in tweets, books, and blog posts. Jack Butcher. Naval Ravikant. Nat Eliason. Daniel Vassallo. Ryan Kulp.  I've read them all and still I've yet to make meaningful progress towards a reality where my income is a result of my past concentrated efforts.  

What I've realized too late is that this failure to create can't be traced back to lacking knowledge. Somewhere along the way I became addicted to consuming information about the outcomes I want to achieve instead of making efforts to create them for myself.  But information was never the bottleneck.

Training, upskilling, and learning are all essential parts of growth, but they won't propel you any closer to your goals if you already knew how to make progress prior to entering your credit card on Gumroad for Yet Another Course.  

I believe there are 3 reasons why I've failed to achieve my goals:

1. Making money freelancing is way easier, and more certain

2. I'm scared of wasting too much time on uncertain returns

3. I'm not entirely convinced I'm capable of doing it, causing me to consume more information as a sense of security

At the end of the day, maybe I'm better suited as a great freelancer or a high performing employee. I don't know just yet. What I do know is that I'm growing impatient waiting to find out.  

Here is the software I install the moment I get a new computer:

AutoHotkey

What is it? An easy way to create custom hotkeys or automations within Windows.

Why you should use it: Using more hotkeys instantly improves your experience using a computer.

How I use it: Here are some of my most used scripts:

• Win+D = Open Downloads folder

• Alt+- = Turn a dash into an Em dash (—)

• Alt+Shift+LeftArrow = Open Chrome profile dedicated to client work

• Alt+Shift+RightArrow = Open Chrome profile dedicated to not work

• Ctrl+Q = Open notes app

Keypirinha

What is it? An application launcher.

Why you should use it: It makes you faster finding and launching things. Once you use it for 2 weeks you won't be able to go without it again.

How I use it: I press Alt+Space and a search bar appears on my screen. It will search my PC for whatever I type (among other features), removing the need to use desktop icons. i.e. "Alt+Space - "ch" - Enter" is enough to open Chrome without using my mouse.

ShareX

What is it? Lightweight, open-source screenshot app.

Why you should use it: Easy screenshots with customizable next actions (save, copy, upload, etc).

How I use it: PrtSc for screenshots. 1-click options for copying to clipboard, editing the image, or uploading to Imgur.

Open Shell

What is it? A skin for Windows Explorer and the Start Menu.

Why you should use it: You don't want to use the new Start Menu and/or you miss Windows XP/Windows 7.

How I use it: I want my Windows 11 to look like Windows XP. I use both the Classic Start Menu and the Classic Explorer.

Microsoft PowerToys

What is it? A package of useful tiny tools.

Why you should use it: This one is on you.

How I use it: I use the Color Picker and Text Extractor most often.

Obsidian

What is it? A simple markdown notetaking app.

Why you should use it: All files are simple markdown that can be exported to most other notes apps. You can leave the ecosystem anytime you want. It's Notepad levels of simple and only as complex as you want it to be.

How I use it: Journaling and reference notes live in my Obsidian database. As a reformed productivity addict I try to keep this simple.

PatchMyPC

What is it? A tool that checks to see if your software is outdated.

Why you should use it: Keep your software up to date.

How I use it: Open every so often to check for updates.

Veracrypt

What is it? A tool to encrypt your hard drive and/or create encrypted volumes.

Why you should use it: A strong personal security practice.

How I use it: I encrypyt my system drive and any USB drives I carry around.

Random Windows hotkeys

Trying to learn more of these.

• Alt+Tab - Cycle between open windows

• Ctrl+L - Jump to address bar when browser is open

• Ctrl+W - Close active browser tab

• Win+RightArrowKey - Push open window to right side of screen

• Win+M - Minimize active window

When things move inefficiently I'm hungry to find a better way to do things. I love knowing a change implemented on my suggestion has made somebody's job easier, enabling them to achieve the same result in less time.

Below are observations on how to optimize remote workflows based on 10 years of working remotely—mostly asynchronously—for small marketing teams and agencies.

1️⃣ Empower your team to work on the work

I believe the secret to a culture of productive remote work is the absence of ambiguity. Clear communication enables your team to work on the work, instead of defining and redefining what needs to be done over and over again before the work is even started.

Remote employees who communicate ambiguously create Metawork for the rest of the team. Metawork is any clarifying question that must be answered before someone can actually work on the work. Metawork is costly to turnaround times, annoying to deal with, and a telltale sign of unrefined operation procedures.    

How can you eliminate Metawork?

By standardizing task assignments and task handoffs. Exactly what information does each person in your company need to complete their tasks?

If I am assigned a task with incomplete information, the following Metawork is created:

1. 👦 I must write out a friendly comment explaining what information I need and send it to the person who assigned the task.

2. 👦 I must wait for that person to see my comment before I can complete the task.

3. 👨 That person must stop working on their active tasks and either (a) pass over the required information or (b) write out a friendly comment explaining they don't have what's required, but will seek it out for me.

4. ️️️️👦I must stop what I'm doing and check my inbox until I notice that the step above has been completed and the information I require to do my job is available to me.

This entire 4-step process could have been avoided entirely, allowing for interrupted work, if the task assigned to me arrived with complete information.

Takeaway: Only assign tasks with complete information. Make perfect handoffs by asking the next person in line what they need to complete their highest frequency tasks, then create templated tasks that require the assignee to add that information before the task is assigned.  

2️⃣ Answer every question once. Document every answer.

A question asked once is an opportunity for filling a gap in team knowledge. A question asked twice is a symptom of poor documentation.

Documentation is automation. Documenting detailed answers to today's questions prevents future metawork from being created when a new team member joins and requires the same information.

Ideally everybody on your team is taught and encouraged how to create functional SOPs with screenshots, Loom videos, and clear instructions. Partial participation is better than none, but baking documentation into team culture will ensure SOPs are always updated and relevant.

Nobody on your team should have to re-teach the work they do to every new hire. That's an added responsibility keeping them from working on the work. Again, documentation is automation. An SOP written or recorded once can teach 10 new hires.        

The better your library of documentation the easier it will be to onboard new hires.

3️⃣ Have a non-negotiable single source of truth  

It should be clear to everybody in your business where they can find the data required to produce the product or service they are responsible for.

The less notifications across unique applications your team has to track the happier they will be. The less pages they need to monitor and maintain the more time they will have to work on the work. A single source of truth empowers them to know at a glance what needs to be done.

📧

What questions do you need your software to answer for you?

The questions your software answers for you will vary depending on your role within the company. Here's how I broke it down for an email marketing agency:

👷‍♀️ Employees building the emails needed the software to answer: what tasks do I need to get done today?

👨‍💼 Project managers controlling the flow of work needed the software to answer: what is the status of project X?

📞 Client specialists managing client relationships needed the software to answer: what have we done for client X recently?

When a human is asking another human these questions, it's a sign your workflow is broken and your task management software isn't living up to its potential. 

Store information about the work (SOPs, company policies, client notes) in Notion or Google Docs and store tasks (aka the work itself) inside of task management software.

A task doesn't exist if it's not assigned in Asana. Company policies, SOPs, and critical notes about clients don't exist if they don't live in Notion.

These rules must be strictly enforced or else the collective trust in your systems will quickly dissolve. The moment your single source of truth doesn't contain 100% of the information your team needs it creates a seed of doubt that's difficult to recover from.

The efficiency of your systems are irrelevant if you're unable to persuade your team to use them as intended. Managers get comfortable holding meetings to get caught up on tasks in progress instead of simply glancing at a dashboard. Project information occasionally gets passed over Slack, damaging the integrity of your single source of truth.  Navigating buy-in is the most difficult part of building workflows.

4️⃣ Standardize how to ask for help

There is no such thing as a stupid question, but incomplete questions create metawork.

hey do you have a minute?

can you help me with something?

can I borrow you for a bit?

Standardizing how questions are asked via Slack/email reduces the amount of wasteful metawork created.

This is the framework I use for asking complete questions:

1. Explain what you're trying to accomplish and what you've already tried. This makes it easier for us to help you.

2. Keep questions as close to the relevant task as much as possible. Questions about an Asana task should be asked in the Asana comment section.

3. Include screenshots (with arrows!) whenever possible.

4. If you need to ask a question on Slack, ask your question to a channel, not a person. This allows everybody the chance to learn together.

5. If you're having trouble typing up a complete question, create a short <5 minute Loom video where you explain what you're trying to accomplish and what you've already tried.

5️⃣ Minimize the use of Slack as much as possible

Slack is a distraction machine that does everything it can to interrupt your team and prevent them working on the work.

Instant messaging promotes stream of consciousness communication and endless back and forth. The metawork created by Slack keeps your team from working on the work.

Slack can be useful when actively chewing on a problem with a coworker in between accomplishing tasks. It's not all bad—Slack can also be an upgrade over email communication which feels impersonal, if not obsolete.

The best compromise I've found is to use Slack for urgent emergencies, personal conversations, or asking questions that aren't relevant to a specific task in Asana. Notification muting should be encouraged to allow everybody to work on the work.

Slack can also be useful in place of a Zoom call or GMeet to collaborate on solving a difficult problem. Neither assigning tasks or discussing tasks should take place in Slack, as this breaks your single source of truth and creates a situation where part of a task lives in Slack and another part lives in your task management software.    

Questions asked in Slack should be asked in channels—not in DMs—so pressure isn't put on a specific person to pause working and answer, and so the answer is visible to everybody who could benefit from seeing it. Answers to questions can then be copied and pasted into an SOP or onboarding doc for the next hire.

6️⃣ Automate or outsource recurring tasks

Recurring non-creative tasks are best done by computers to free up time for humans to work on tasks best done by humans. Hire a marketing automation specialist to review all your SOPs so they can tell you which tasks they can retire from your workflow by means of automation.

Not everything should be automated. Automation is rarely ever perfect. Automations require maintenance, monitoring, and quality control. It's important these trade-offs are made obvious and documented in your SOPs.

Outsourcing to a micro-freelancer can be another form of automation.

Small companies often have employees handling tasks outside of their core competencies. This results in mediocre output and damages team morale, because nobody wants to be responsible for work they know they're not very good at. Hiring a freelancer or virtual assistant to handle these tasks will make work more enjoyable for your employees and potentially even improve the output.  

7️⃣ Standardize how to give feedback

When someone deviates from a SOP it could be a sign that your process isn't the best way to achieve the output you're looking for. Standardize a way your employees can propose changes to existing SOPs so nobody feels trapped performing a task in a sub-standard manner.

It's also a good idea to standardize how to give feedback to someone who has (accidentally) deviated from procedure. Using a template to inform someone that they made a mistake, how they should fix it, and how they can avoid it in the future, saves a ton of time and awkwardness many people feel when correcting others.      

I’ve spent more time traveling than being "home" over the past few years. I’m still learning how to travel in a way that allows me to be my best self regardless of which country I'm in.

I’ve recently solidified my belief that you can’t treat long-term travel like a vacation. When your definition of travel shifts from a temporary escape to an ongoing lifestyle, you no longer get a free pass to let yourself go.

Vacationers seek novelty when they travel. Their goal is to compress as many novel experiences as they can into the limited time they have to explore before their obligations at home claw them back into “the real world”.

Having a limited time budget afforded to travel, vacationers drop spending time on real world habits—exercise, eating healthy, maintaining hobbies—to maximize itinerary events: beaches, postcard views, and socially accepted alcoholism (because vacation).

Suspending everyday responsibilities to enjoy a brief escape from life makes for a memorable vacation. But prioritize itinerary events over habits and routines long enough and you’ll quickly realize the novelty of a just desserts lifestyle leaves you craving the nutritious fulfilment of boring-but-healthy routines.

This is my nomad conundrum: sufficiently experiencing a new destination while also maintaining habits that (1) pay the bills and (2) fuel the person I want to be.

The real world rarely hands over fulfilment for free. To feel accomplished we need to accomplish things. No matter what country we happen to be living in.

Being able to work anywhere, at any time, for not that many hours, is a privilege I’m proud of. But that freedom doesn’t change the formula for fulfilment.

No amount of new friends or new foods will replace the enduring gratification of completing a full month of workouts, finishing the right book, or making progress towards a meaningful goal.

Optimizing nomadic travel for happiness

Travel changes your environment and the people around you but it doesn’t change what makes you happy. In a practical sense this means knowing what you need to be at your best, and then ensuring it can be obtained at your next destination.

💪 If the gym is too busy or too far away, I won't go.

🍳 If I can't make eggs from my apartment, I'll eat an unhealthy breakfast.

🌞 If I don't have easy access to sunlight, I'll spend too much time indoors and have a hard time waking up in the morning. 

Trial and error has taught me I need to live somewhere that minimizes friction around meeting my goals. These are not nice-to-haves, they're non-negotiable parts of choosing a place to stay that have the potential to make or break my happiness for an entire month or longer.

I've learned it's much harder to check these boxes (among others) during short stays of 1 month or less.

👶 When I first started traveling: the excitement of hopping between cities, meeting new people, and telling stories about yet another new country was fun.

👴 Now: I hate airports, am tired of packing and unpacking my one bag, and restarting somewhere else right after I've built some momentum.

It's just easier to build routines with 3+ months of leeway. 1 month is barely enough (for me) to get comfortable in a neighborhood. Moving forward I'm looking at staying places for at least 2+ months at a time, outside of short side trips.

🔗 Similar vibes

More To ThatLawrence Yeo

You owe something to every thing you own.

Each item you cram into your suitcase is an obligation you’re committing to maintain, protect, or give attention to for the duration of your trip. The less you bring, the less responsibility you have.

You need money and a passport to travel. Everything else is optional. Finding out how much stuff is ‘enough’ is for you, and then packing just a little bit less than that, is where the challenge lies.

I try to make sure all the clothing I bring can be mix-and-matched, so my navy shirt isn’t waiting for me to change out of my navy pants to avoid offending international fashion laws.

I shoot for a full week’s worth of clothing. Doing laundry once a week is manageable. If I can get an Airbnb with a washing machine, that's a win. Otherwise I'll compare the cost of laundry service against the hassle of planning around a local laundromat.

Made-for-travel clothing can often be washed in the bathroom sink with minimal effort. This isn't my first choice, but it's a viable plan B and a bonus for spending a little extra on quality clothing.

Shirts are the highest maintenance clothing items. Decent pants can be worn at least 4-5 days in a row. Socks and underwear are easy candidates to be washed in the sink before bed. I haven’t figured out shirts yet.

A recent optimization I've made to my travel packing routine is minimizing charging cables and adapters. All my electronics can now be charged via a USB-C cable, including my electric shaver. Bulky power adapters are no longer necessary, just 2x USB-C cables and a USB wall charger.

My stuff is split into smaller bags and pouches before being put into my main bag. This is the secret to organized one bag travel.

My clothes live inside of a packing cube, my electronics and cables live inside of a large pouch, my liquids in a freezer bag, toiletries in another, and my laptop inside of a collapsible day bag. Packing takes 10 minutes, unpacking takes 1 minute.

The cost of packing less essentially comes down to having a small wardrobe. I deal with this by doing laundry weekly, buying durable clothes, and/or buying more clothes on location, if I need to.

In return I get to travel with a small 25L backpack that wouldn’t look out of place if I wore it to school. No checked baggage. No baggage claim lines. No thinking about stuff whatsoever.

My One Bag Travel Packing List

This is my current packing list for indefinite one bag international travel. This is (more or less) what I've taken on trips as long as 11 months.

Travel essentials

I like to remind myself that I could technically get by with only these things and the clothes on my back.

• Passport

• Wallet

• Phone

• Laptop

• USB-C charger (for phone + laptop)

• Packable, waterproof day bag (Matador brand)

• Red folder for travel documents (visas, etc)

Clothing for indefinite travel

I spend most of my time in warmer climates. I'll occasionally buy cheap clothes to wear around the house if needed.

All my clothes are packed inside my Peak Designs packing cube.

• 5x boxers

• 2x socks (1 long, 1 short)

• 3x button-up shirts

• 3x t-shirts

• 1x pants

• 1x shorts

• 1x workout/swim shorts

• 1x workout shirt

• 1x belt

Gadgets/electronics/accessories

• Laptop + phone (mentioned above)

• Wireless earbuds

• Kindle

• Wireless mouse

• Portable 1TB SSD

• USB-C to USB-C cable (2)

• USB-C to mUSB cable (1)

• Electric shaver

• Aeropress Go

• Manual coffee grinder

• Coffee scale

• Sunglasses

• Sleep mask

• Titanium spork

Toiletries etc

• Toothbrush

• Deodorant

• Sunscreen

• Moisturizer

• Tweezers

• Nail clippers

• Hair styling product

• Tylenol + Tylenol AM/PM for colds

• Pepto Bismol chewables

My Favorite One Bag Travel Resources

Chase Reeves is the ultimate resource for finding your ‘one bag’. He also keeps a record of the products he reviews on Matterful but his videos are way better.

The /r/onebag subreddit is also good for community sourced opinions and packing lists based on bag sizes and trip length.

Nomad List is alright. I rarely use the website itself. Membership can be worth it for access to the Slack community.

I forward all receipts from flights, accommodation bookings, etc to the TripIt app for trip tracking.

I typically use Skyscanner for finding flights. I hear Kiwi might be better.

I have a phone number parked at NumberBarn, which forwards all my texts and 2FA confirmations to my email for a few bucks each month.

I buy credits for Skype if I need to call a real phone number (i.e. can't use Telegram or WhatsApp). I use web.skype.com (not the ugly app).

My Favorite Packing Lists

• Ultralight Packing List by James Clear

• How to pack for world travel with just a carry-on bag by Pieter Levels

The marshmallow test has failed us.

People everywhere are delaying gratification for too long—or indefinitely—and patting themselves on the back for it.

We spend our waking hours doing everything we can to avoid squandering our money. What we don't realize is that we're squandering our lives in the process.

These are all things I learned from reading Die With Zero, a contrarian take on personal finance by Bill Perkins.

Enter Bill Perkins

I was first introduced to Perkins' bouncy personality through watching high stakes poker tournaments, where the ex-hedge fund manager regularly battles studied poker professionals. There's nothing poker pros love more than being seated next to a businessman. Perkins is well aware of this—and he couldn't care less.

The poker sharks surrounding Perkins at highroller poker tournaments are sitting at the table because the math adds up: they expect to finish the $100,00 buy-in tournament with a higher net worth than what they had when they started, on average. Modern poker has become more and more a game of math.

The days of staring a player down to expose their tell or risking your entire stack of chips because of a gut feeling are fading away as new age internet players outnumber the old school 'feel' players. Today's poker professionals weaponize probability and memorize complex decisions trees to gain edges on the field of fellow gamblers.

Perkins isn't much of a 'math guy' at the poker tables, but his contrarian take on personal finance is a result of leveraging his engineering background to address the following question: how do we make the most of our time on earth? By maximizing fulfilment by minimizing waste.

Perkins wants to die with zero, leaving no wasted energy behind at the end of his fulfilled life. And he believes you could benefit from doing the same thing. You don't need to be a retired hedge fund manager to see why living according to Perkins' principles could result in a memorable life.

Here are several of Perkins' principles underlying his Die With Zero philosophy:

😀 Your life is the sum of your experiences. We can't simply accumulate experiences right off the bat because experiences have a price. We need to take the intermediate step of earning money first.

💀 Dying with a massive bank account balance is a symptom of an unfulfilled life. Every dollar you don't spend is a waste of Life Energy and a misallocation of time you'll never get back.

⏰ When you experience something is more important than if you experience it at all, because our ability to enjoy different kinds of experiences changes as we age.

😖 You're probably saving too much money ""just in case"". There's a better way to protect yourself from unforeseen events than mindlessly piling more money into your savings account.

💪 Your health is a multiplier of lifetime fulfillment. Healthy people have more fun. For longer.

Money as a Measure of Life Energy

Stumbling across the concept of Life Energy forever changed the way Perkins viewed money—and this transformation happened well before he had a chance to amass millions of dollars, so pay attention:

Life Energy ⚡

This mindset changes everything. That new coat you were thinking about buying? That's no longer just a $250 coat, that's a coat that costs 10 non-refundable hours of your life at your $25/hour job. Is it worth it? That's up to you.

The objective isn't to minimize spending or practice frugality, but rather to expose the non-financial costs incurred with every purchase. Especially ones that cost time you'll never get back. Evaluating your life through the lens of Life Energy can be a real breakthrough.

Jumping ship to a new company under the promise of a large raise sounds like a financial win. But if the extra income comes with added stress, a long commute, and a difficult manager, you're paying a higher price in Life Energy for every dollar earned.

This is the core belief driving Perkins' desire to die with zero: every dollar left behind represents unrealized experience. If you earn $45,000 year and die with $90,000 in the bank, that's more than 2 entire years of hard work going to waste—considering you never redeemed your payment, you essentially worked 2 years for free.

Tiny Deaths

When you experience something is just as important as whether you experience it at all. Understanding this will instantly change your perspective on spending more money on experiences earlier in life.

• Disney World is a dream come true at age 10, but a total drag at age 17

• Navigating the jungles of Southeast Asia is the ultimate adventure in your 20s, but becomes too big of a mission to take on at age 50

• Snowboarding the most famous mountains in the world is an admirable bucket list item—until you're 70 or older... then it's a death wish

The day you die and the day you stop being able to enjoy certain experiences are different things. If being mindful of your mortality is a superpower, then being mindful of impermanence is a hyperpower. There's a 'last time' you do everything we do. And we almost never see it coming:

• A last time you walk your family dog around the block before you move out

• A last time you read a familiar children's book to your daughter before she unexpectedly grows bored of it

• A last time your parents give you a hard time over something silly before they're not around anymore

As Perkins puts it, the endpoints of experiences in your life are unknown. You will experience thousands of tiny deaths throughout your lifetime. Entire stages of your life expire without prior warning. It's crucial that we break out of our routines every now and then to do something memorable before it's too late.

The Mindless Saving Loop

Nassim Taleb famously claimed the three most harmful addictions in life are heroin, carbohydrates, and a monthly salary. Once we start saving money and marvel at the size of our savings, it's hard to stop saving.

We shift the goal posts: what was once a $5,000 emergency fund has become a $10,000 emergency fund, then a $20,000 emergency fund after completing further mental gymnastics and "what if" scenarios.

The habit of mindlessly saving more money is hard to break. Perkins shares that there are people in their 70s, still adding money to their savings for the future, refusing to dip into the massive amounts of Life Energy they've been accumulating for decades.

Most people focus on growing their savings so (a) they don't run out of money when it comes time to retire, and (b) so they're prepared for a medical disaster. The problem with this is that few people know how much money is enough money.

Let's use a medical disaster as an example: how much money is enough?

To put it bluntly: no amount of savings will cover the costliest outcomes. Cancer treatments can cost upwards of $500,000/year—your savings won't save you in these scenarios. Perkins uses the grim example above to illuminate how, when the costs of medical care are uncertain, people continually save more and more towards an impossible goal they will never reach.

Saving for specific, attainable goals can be good. Saving indefinitely at the expense of your growth as a person and your memory bank, which you will later retire on, is shortsighted. A solution to breaking free of the savings loop is to trust the professional risk calculators: buy insurance.

Insurance companies quantify risks better than we can as individuals. They take a healthy fee in the process of smoothing our uncertainty, but they're also freeing us from mindlessly locking up money out of habit for the rest of our lives. Insurance products worth knowing about:

• If you're afraid of dying too soon: you want protection against mortality risk (i.e. traditional life insurance)

• If you're afraid of living too long and running out of money: you want protection against longevity risk (annuities)

Perkins mentions these insurance products can be complicated. Annuities (longevity risk) are a bad investment on paper, yet a useful way to prevent over-saving. Consult a fee-based financial advisor on your own to discuss which insurance products (if any) are right for you.

The Best Investment You Can Make

Investing in your health is the best investment you can make. Do not write this off as a cliché. Your health is a multiplier of lifetime fulfillment: investing in your health is investing in every single subsequent experience you have.

Nothing has a greater effect on your ability to enjoy experiences at any age than your health. And the best health insurance you can get comes in the form of preventative care.

Perkins makes an important distinction between your chronological age and your biological age. The average 60 year-old isn't going to be in good enough shape to experience as much as the average 30 year-old. But there are exceptions to the rule.

By investing into your health early and often you can put yourself in a position to be an exception to the rule, extending the amount of time you have in this lifetime to enjoy physically demanding experiences.

Conclusion

The game of poker is about maximizing your probability of winning the most amount of chips possible. In Die With Zero, Bill Perkins argues the game of life is about maximizing fulfillment, leaving behind as little wasted Life Energy as possible.

There were many interesting concepts from the book left out of this article, including why Perkins thinks we're doing inheritances all wrong, why the 50/30/20 savings rule is busted, and when you should start dipping into your savings.

Each person in your life experiences you in a unique way.

You're a different person to your best friend than you are to your neighbor than you are to your significant other, and everybody is better off for it.

You group most relationships into the same broad "friend" category, yet you're unlikely to treat any two "friends" identically. There's more granularity to our relationships than broad categorization can account for.

Relationships are better defined by tags than they are folders.

There are three sides to any relationship:

1. How that person makes your feel
2. How you make that person feel
3. The known overlap between the previous two factors

It's rare for any two people to make us feel identically. Any discrepancy in this three ingredient recipe will result in a unique relationship being formed.

We each see ourselves as a consistent person with certain interests and certain quirks, but the reality is that we bring a different sum of ourselves to each of our relationships. We're rarely, if ever, the same identical person to many people.

I think taking notes is the same as taking photos when you’re on a trip. All it’s doing is taking you out of the moment. - Naval Ravikant

Reading to deeply understand a topic and reading to maximize your exposure to ideas are two different approaches to reading. One of these approaches makes reading significantly more enjoyable than the other.

We feel a responsibility to retain information when reading. This is why we take notes. Notes are to reading what sweat is to exercise. Note taking is our Proof of Reading, evidence that we've extracted a sufficient amount of information from the book we've reading.

Going forward, I plan to reserve reading to deeply understand for books that have earned that right, making reading to maximize exposure to ideas my default mode of reading.

Here's why:

The goal of reading to maximize exposure to ideas is  not to retain a sufficient amount of the book to memory, but to stroll through the book to see if any passages or concepts are interesting enough to make you stop.

Do you notice the shift in mindset?

The responsibility is turned back to the book: it must entertain or inform, otherwise it will be skimmed or skipped.

I skim. I speed read. I jump around. I could not tell you specific passages or quotes from books. At some deep level, you do absorb them and they become part of the threads of the tapestry of your psyche. - Naval Ravikant

Treat your books as if they are auditioning in front of you, attempting to pitch you on their most interesting ideas. The book has to earn a second date before you commit to it.

This means worrying less about proving you've read something and more about whether it's worth reading in the first place. The difference between reading out of obligation (powered by willpower) and reading because the book has captured your attention (powered by curiosity) is refreshingly freeing.

All quotes are taken from Episode 18 of Shane Parrish's The Knowledge Project featuring Naval Ravikant. Transcript here. Podcast here.