The holy grail of plain text task management is finally within reach

Plain text task management? Are you serious?? Dedicated task managers exist for a reason, you know. Sheesh.

—Oh, I know. Believe me, I know! But hear me out.

I've managed projects and tasks in plain text for more than four years. Since reorganizing my to-do list, plain text task management is within reach.

Data completely yours? One billion percent. Beef it up with coding? Be my guest.

Enter: The List

The answer? A list. That’s it!

Write down tasks. Obsidian, Notenik, Drafts, or iA Writer are good plain text note-taking apps.

List too long? Of course, it is! A large list tells you what to do. Feel the itch and friction. Then fix it.

• But I want to be able to distinguish between work and personal life! List two things.

• However, I need to know what should be completed first. Put those items at the top.

• However, some things keep coming up, and I need to be reminded of them! Put those in your calendar and make an alarm for them.

• But since individual X hasn't completed task Y, I can't proceed with this. Create a Waiting section on your list by dividing it.

• But I must know what I'm supposed to be doing right now! Read your list(s). Check your calendar. Think critically.

Before I begin a new one, I remind myself that "Listory Never Repeats."

There’s no such thing as too many lists if all are needed. There is such a thing as too many lists if you make them before they’re needed. Before they complain that their previous room was small or too crowded or needed a new light.

A list that feels too long has a voice; it’s telling you what to do next.

I use one Master List. It's a control panel that tells me what to focus on short-term. If something doesn't need semi-immediate attention, it goes on my Backlog list.

Todd Lewandowski's DWTS (Done, Waiting, Top 3, Soon) performance deserves praise. His DWTS to-do list structure has transformed my plain-text task management. I didn't realize it was upside down.

This is my take on it:

D = Done

Move finished items here. If they pile up, clear them out every week or month. I have a Done Archive folder.

W = Waiting

Things seething in the background, awaiting action. Stir them occasionally so they don't burn.

T = Top 3

Three priorities. Personal comes first, then work. There will always be a top 3 (no more than 5) in every category. Projects, not chores, usually.

S = Soon

This part is action-oriented. It's for anything you can accomplish to finish one of the Top 3. This collection includes thoughts and project lists. The sole requirement is that they should be short-term goals.

Some of you have probably concluded this isn't for you. Please read Todd's piece before throwing out the baby. Often. You shouldn't miss a newborn.

As much as Dancing With The Stars helps me recall this method, I may try switching their order. TSWD; Drilling Tunnel Seismic? Serenity After Task?

Master List Showcase

My Master List lives alone in its own file, but sometimes appears in other places.  It's included in my Weekly List template. Here's a (soon-to-be-updated) demo vault of my Obsidian planning setup to download for free.

Here's the code behind my weekly screenshot:

## [[Master List - 2022|✓]]  TO DO

![[Master List - 2022]]

FYI, I use the Minimal Theme in Obsidian, with a few tweaks.

You may note I'm utilizing a checkmark as a link. For me, that's easier than locating the proper spot to click on the embed.

Blue headings for Done and Waiting are links. Done links to the Done Archive page and Waiting to a general waiting page.

Read my full article here.

I've spent the last 10 years of my career mastering time management. I've tried different approaches and followed multiple people and sources. My knowledge is summarized.

Great people, including entrepreneurs, master time management. I learned time management in college. I was studying Computer Science and Finance and leading Tanzanian students in Bangalore, India. I had 24 hours per day to do this and enjoy campus. I graduated and received several awards. I've learned to maximize my time. These tips and tools help me finish quickly.

Eisenhower-Box

I don't remember when I read the article. James Clear, one of my favorite bloggers, introduced me to the Eisenhower Box, which I've used for years. Eliminate waste to master time management. By grouping your activities by importance and urgency, the tool helps you prioritize what matters and drop what doesn't. If it's urgent, do it. Delegate if it's urgent but not necessary. If it's important but not urgent, reschedule it; otherwise, drop it. I integrated the tool with Trello to manage my daily tasks. Since 2007, I've done this.

James Clear's article mentions Eisenhower Box.

Essentialism rules

Greg McKeown's book Essentialism introduced me to disciplined pursuit of less. I once wrote about this. I wasn't sure what my career's real opportunities and distractions were. A non-essentialist thinks everything is essential; you want to be everything to everyone, and your life lacks satisfaction. Poor time management starts it all. Reading and applying this book will change your life.

Essential vs non-essential

Life Calendar

Most of us make corporate calendars. Peter Njonjo, founder of Twiga Foods, said he manages time by putting life activities in his core calendars. It includes family retreats, weddings, and other events. He joked that his wife always complained to him to avoid becoming a calendar item. It's key. "Time Masters" manages life's four burners, not just work and corporate life. There's no "work-life balance"; it's life.

Health, Family, Work, and Friends.

The Brutal No

In a culture where people want to look good, saying "NO" to a favor request seems rude. In reality, the crime is breaking a promise. "Time Masters" have mastered "NO".  More "YES" means less time, and more "NO" means more time for tasks and priorities. Brutal No doesn't mean being mean to your coworkers; it means explaining kindly and professionally that you have other priorities.

To-Do vs. MITs

Most people are productive with a routine to-do list. You can't be effective by just checking boxes on a To-do list. When was the last time you completed all of your daily tasks? Never. You must replace the to-do list with Most Important Tasks (MITs). MITs allow you to focus on the most important tasks on your list. You feel progress and accomplishment when you finish these tasks. MITs don't include ad-hoc emails, meetings, etc.

Journal Mapped

Most people don't journal or plan their day in the developing South. I've learned to plan my day in my journal over time. I have multiple sections on one page: MITs (things I want to accomplish that day), Other Activities (stuff I can postpone), Life (health, faith, and family issues), and Pop-Ups (things that just pop up). I leave the next page blank for notes. I reflected on the blocks to identify areas to improve the next day. You will have bad days, but at least you'll realize it was due to poor time management.

Buy time/delegate

Time or money? When you make enough money, you lose time to make more. The smart buy "Time." I resisted buying other people's time for years. I regret not hiring an assistant sooner. Learn to buy time from others and pay for time-consuming tasks. Sometimes you think you're saving money by doing things yourself, but you're actually losing money.

This post is a summary. See the full post here.

Offices without books are like bodies without souls.

After 10 years, my CEO sold his company for $30 million. I've shared many of his lessons on medium. You could ask him anything at his always-open office. He also said we could use his office for meetings while he was away. When I used his office for work, I was always struck by how many books he had.

Books are useful in almost every aspect of learning. Building a business, improving family relationships, learning a new language, a new skill... Books teach, guide, and structure. Whether fiction or nonfiction, books inspire, give ideas, and develop critical thinking skills.

My CEO prefers non-fiction and attends a Friday book club. This article discusses 5 books I found in his office that impacted my life/business. My CEO sold his company for $30 million, but I've built a steady business through blogging and video making.

I recall events and lessons I learned from my CEO and how they relate to each book, and I explain how I applied the book's lessons to my business and life.

Note: This post has no affiliate links.

1. The One Thing — Gary Keller

Gary Keller, a real estate agent, wanted more customers. So he and his team brainstormed ways to get more customers. They decided to write a bestseller about work and productivity. The more people who saw the book, the more customers they'd get.

Gary Keller focused on writing the best book on productivity, work, and efficiency for months. His business experience. Keller's business grew after the book's release.

The author summarizes the book in one question.

"What's the one thing that will make everything else easier or unnecessary?"

When I started my blog and business alongside my 9–5, I quickly identified my one thing: writing. My business relied on it, so it had to be great. Without writing, there was no content, traffic, or business.

My CEO focused on funding when he started his business. Even in his final years, he spent a lot of time on the phone with investors, either to get more money or to explain what he was doing with it. My CEO's top concern was money, and the other super important factors were handled by separate teams.

• Product tech and design

• Incredible customer support team

• Excellent promotion team

• Profitable sales team

My CEO didn't always focus on one thing and ignore the rest. He was on all of those teams when I started my job. He'd start his day in tech, have lunch with marketing, and then work in sales. He was in his office on the phone at night.

He eventually realized his errors. Investors told him he couldn't do everything for the company. If needed, he had to change internally. He learned to let go, mind his own business, and focus for the next four years. Then he sold for $30 million.

The bigger your project/company/idea, the more you'll need to delegate to stay laser-focused. I started something new every few months for 10 years before realizing this. So much to do makes it easy to avoid progress. Once you identify the most important aspect of your project and enlist others' help, you'll be successful.

2. Eat That Frog — Brian Tracy

The author quote sums up book's essence:

Mark Twain said that if you eat a live frog in the morning, it's probably the worst thing that will happen to you all day. Your "frog" is the biggest, most important task you're most likely to procrastinate on.

"Frog" and "One Thing" are both about focusing on what's most important. Eat That Frog recommends doing the most important task first thing in the morning.

I shared my CEO's calendar in an article 10 months ago. Like this:

CEO's average week (some information crossed out for confidentiality)

Notice anything about 8am-8:45am? Almost every day is the same (except Friday). My CEO started his day with a management check-in for 2 reasons:

• Checking in with all managers is cognitively demanding, and my CEO is a morning person.

• In a young startup where everyone is busy, the morning management check-in was crucial. After 10 am, you couldn't gather all managers.

When I started my blog, writing was my passion. I'm a morning person, so I woke up at 6 am and started writing by 6:30 am every day for a year. This allowed me to publish 3 articles a week for 52 weeks to build my blog and audience. After 2 years, I'm not stopping.

3. Deep Work — Cal Newport

Deep work is focusing on a cognitively demanding task without distractions (like a morning management meeting). It helps you master complex information quickly and produce better results faster. In a competitive world 10 or 20 years ago, focus wasn't a huge advantage. Smartphones, emails, and social media made focus a rare, valuable skill.

Most people can't focus anymore. Screens light up, notifications buzz, emails arrive, Instagram feeds... Many people don't realize they're interrupted because it's become part of their normal workflow.

Cal Newport mentions Bill Gates' "Think Weeks" in Deep Work.

Microsoft CEO Bill Gates would isolate himself (often in a lakeside cottage) twice a year to read and think big thoughts.

Inside Bill's Brain on Netflix shows Newport's lakeside cottage. I've always wanted a lakeside cabin to work in. My CEO bought a lakehouse after selling his company, but now he's retired.

As a company grows, you can focus less on it. In a previous section, I said investors told my CEO to get back to basics and stop micromanaging. My CEO's commitment and ability to get work done helped save the company. His deep work and new frameworks helped us survive the corona crisis (more on this later).

The ability to deep work will be a huge competitive advantage in the next century. Those who learn to work deeply will likely be successful while everyone else is glued to their screens, Bluetooth-synced to their watches, and playing Candy Crush on their tablets.

4. The 7 Habits of Highly Effective People — Stephen R. Covey

It took me a while to start reading this book because it seemed like another shallow self-help bible. I kept finding this book when researching self-improvement. I tried it because it was everywhere.

Stephen Covey taught me 2 years ago to have a personal mission statement.

A 7 Habits mission statement describes the life you want to lead, the character traits you want to embody, and the impact you want to have on others. shortform.com

I've had many lunches with my CEO and talked about Vipassana meditation and Sunday forest runs, but I've never seen his mission statement. I'm sure his family is important, though. In the above calendar screenshot, you can see he always included family events (in green) so we could all see those time slots. We couldn't book him then. Although he never spent as much time with his family as he wanted, he always made sure to be on time for his kid's birthday rather than a conference call.

My CEO emphasized his company's mission. Your mission statement should answer 3 questions.

• What does your company do?

• How does it do it?

• Why does your company do it?

As a graphic designer, I had to create mission-statement posters. My CEO hung posters in each office.

5. Measure What Matters — John Doerr

This book is about Andrew Grove's OKR strategy, developed in 1968. When he joined Google's early investors board, he introduced it to Larry Page and Sergey Brin. Google still uses OKR.

Objective Key Results

• Objective: It explains your goals and desired outcome. When one goal is reached, another replaces it. OKR objectives aren't technical, measured, or numerical. They must be clear.

• Key Result should be precise, technical, and measurable, unlike the Objective. It shows if the Goal is being worked on. Time-bound results are quarterly or yearly.

Our company almost sank several times. Sales goals were missed, management failed, and bad decisions were made. On a Monday, our CEO announced we'd implement OKR to revamp our processes.

This was a year before the pandemic, and I'm certain we wouldn't have sold millions or survived without this change. This book impacted the company the most, not just management but all levels. Organization and transparency improved. We reached realistic goals. Happy investors. We used the online tool Gtmhub to implement OKR across the organization.

My CEO's company went from near bankruptcy to being acquired for $30 million in 2 years after implementing OKR.

I hope you enjoyed this booklist. Here's a recap of the 5 books and the lessons I learned from each.

1. The 7 Habits of Highly Effective People — Stephen R. Covey

Have a mission statement that outlines your goals, character traits, and impact on others.

1. Deep Work — Cal Newport

Focus is a rare skill; master it. Deep workers will succeed in our hyper-connected, distracted world.

1. The One Thing — Gary Keller

What can you do that will make everything else easier or unnecessary? Once you've identified it, focus on it.

1. Eat That Frog — Brian Tracy

Identify your most important task the night before and do it first thing in the morning. You'll have a lighter day.

1. Measure What Matters — John Doerr

On a timeline, divide each long-term goal into chunks. Divide those slices into daily tasks (your goals). Time-bound results are quarterly or yearly. Objectives aren't measured or numbered.

Thanks for reading. Enjoy the ride!

A top-down company plan facilitates decision-making and impresses investors.

A startup business plan starts with the product, the target customers, how to reach them, and how to grow the business.

Bottom-up is terrific unless venture investors fund it.

If it can prove how it can exceed $100M in sales, investors will invest. If not, the business may be wonderful, but it's not venture capital-investable.

As a rule, venture investors only fund firms that expect to reach $100M within 5 years.

Investors get nothing until an acquisition or IPO. To make up for 90% of failed investments and still generate 20% annual returns, portfolio successes must exit with a 25x return. A $20M-valued company must be acquired for $500M or more.

This requires $100M in sales (or being on a nearly vertical trajectory to get there). The company has 5 years to attain that milestone and create the requisite ROI.

This motivates venture investors (venture funds and angel investors) to hunt for $100M firms within 5 years. When you pitch investors, you outline how you'll achieve that aim.

I'm wary of pitches after seeing a million hockey sticks predicting $5M to $100M in year 5 that never materialized. Doubtful.

Startups fail because they don't have enough clients, not because they don't produce a great product. That jump from $5M to $100M never happens. The company reaches $5M or $10M, growing at 10% or 20% per year.  That's great, but not enough for a $500 million deal.

Once it becomes clear the company won’t reach orbit, investors write it off as a loss. When a corporation runs out of money, it's shut down or sold in a fire sale. The company can survive if expenses are trimmed to match revenues, but investors lose everything.

When I hear a pitch, I'm not looking for bright income projections but a viable plan to achieve them. Answer these questions in your pitch.

• Is the market size sufficient to generate $100 million in revenue?

• Will the initial beachhead market serve as a springboard to the larger market or as quicksand that hinders progress?

• What marketing plan will bring in $100 million in revenue? Is the market diffuse and will cost millions of dollars in advertising, or is it one, focused market that can be tackled with a team of salespeople?

• Will the business be able to bridge the gap from a small but fervent set of early adopters to a larger user base and avoid lock-in with their current solution?

• Will the team be able to manage a $100 million company with hundreds of people, or will hypergrowth force the organization to collapse into chaos?

• Once the company starts stealing market share from the industry giants, how will it deter copycats?

The requirement to reach $100M may be onerous, but it provides a context for difficult decisions: What should the product be? Where should we concentrate? who should we hire? Every strategic choice must consider how to reach $100M in 5 years.

Focusing on $100M streamlines investor pitches. Instead of explaining everything, focus on how you'll attain $100M.

As an investor, I know I'll lose my money if the startup doesn't reach this milestone, so the revenue prediction is the first thing I look at in a pitch deck.

Reaching the $100M goal needs to be the first thing the entrepreneur thinks about when putting together the business plan, the central story of the pitch, and the criteria for every important decision the company makes.

Could this happen?

Medium isn't like other social media giants. It wasn't a dot-com startup that became a multi-trillion-dollar social media firm. It launched in 2012 but didn't gain popularity until later. Now, it's one of the largest sites by web traffic, but it's still little compared to most. Most of Medium's traffic is external, but they don't run advertisements, so it's all about memberships.

Medium isn't profitable, but they don't disclose how terrible the problem is. Most of the $163 million they raised has been spent or used for acquisitions. If the money turns off, Medium can't stop paying its writers since the site dies. Writers must be paid, but they can't substantially slash payment without hurting the platform. The existing model needs scale to be viable and has a low ceiling. Facebook and other free social media platforms are struggling to retain users. Here, you must pay to appreciate it, and it's bad for writers AND readers. If I had the same Medium stats on YouTube, I'd make thousands of dollars a month.

Then what? Medium has tried to monetize by offering writers a cut of new members, but that's unsustainable. People-based growth is limited. Imagine recruiting non-Facebook users and getting them to pay to join. Some may, but I'd rather write.

Alternatives:

• Donation buttons

• Tiered subscriptions ($5, $10, $25, etc.)

• Expanding content

and these may be short-term fixes, but they're not as profitable as allowing ads. Advertisements can pay several dollars per click and cents every view. If you get 40,000 views a month like me, that's several thousand instead of a few hundred. Also, Medium would have enough money to split ad revenue with writers, who would make more. I'm among the top 6% of Medium writers. Only 6% of Medium writers make more than $100, and I made $500 with 35,000 views last month. Compared to YouTube, the top 1% of Medium authors make a lot. Mr. Beast and PewDiePie make MILLIONS a month, yet top Medium writers make tens of thousands. Sure, paying 3 or 4 people a few grand, or perhaps tens of thousands, will keep them around. What if great authors leveraged their following to go huge on YouTube and abandoned Medium? If people use Medium to get successful on other platforms, Medium will be continuously cycling through authors and paying them to stay.

Ads might make writing on Medium more profitable than making videos on YouTube because they could preserve the present freemium model and pay users based on internal views. The $5 might be ad-free.

Consider: Would you accept Medium ads? A $5 ad-free version + pay-as-you-go, etc. What are your thoughts on this?

Original post available here