Ray Dalio's super-effective roadmap 

Ray Dalio's $22 billion net worth ranks him 36th globally. From 1975 to 2011, he built the world's most successful hedge fund, never losing more than 4% from 1991 to 2020. (and only doing so during 3 calendar years). 

Dalio describes a 5-step process in his best-selling book Principles. It's the playbook he's used to build his hedge fund, beat the markets, and face personal challenges. 

This 5-step system is so valuable and well-explained that I didn't edit or change anything; I only added my own insights in the parts I found most relevant and/or relatable as a young entrepreneur. The system's overview: 

1. Have clear goals 

2. Identify and don’t tolerate problems 

3. Diagnose problems to get at their root causes 

4. Design plans that will get you around those problems 

5. Do what is necessary to push through the plans to get results 

If you follow these 5 steps in a virtuous loop, you'll almost always see results. Repeat the process for each goal you have. 

1. Have clear goals 

a) Prioritize: You can have almost anything, but not everything. 

I started and never launched dozens of projects for 10 years because I was scattered. I opened a t-shirt store, traded algorithms, sold art on Instagram, painted skateboards, and tinkered with electronics. I decided to try blogging for 6 months to see where it took me. Still going after 3 years. 

b) Don’t confuse goals with desires. 

A goal inspires you to act. Unreasonable desires prevent you from achieving your goals. 

c) Reconcile your goals and desires to decide what you want. 

d) Don't confuse success with its trappings. 

e) Never dismiss a goal as unattainable. 

Always one path is best. Your perception of what's possible depends on what you know now. I never thought I'd make money writing online so quickly, and now I see a whole new horizon of business opportunities I didn't know about before. 

f) Expectations create abilities. 

Don't limit your abilities. More you strive, the more you'll achieve. 

g) Flexibility and self-accountability can almost guarantee success. 

Flexible people accept what reality or others teach them. Self-accountability is the ability to recognize your mistakes and be more creative, flexible, and determined. 

h) Handling setbacks well is as important as moving forward. 

Learn when to minimize losses and when to let go and move on. 

2. Don't ignore problems 

a) See painful problems as improvement opportunities. 

Every problem, painful situation, and challenge is an opportunity. Read The Art of Happiness for more. 

b) Don't avoid problems because of harsh realities. 

Recognizing your weaknesses isn't the same as giving in. It's the first step in overcoming them. 

c) Specify your issues. 

There is no "one-size-fits-all" solution. 

d) Don’t mistake a cause of a problem with the real problem. 

"I can't sleep" is a cause, not a problem. "I'm underperforming" could be a problem. 

e) Separate big from small problems. 

You have limited time and energy, so focus on the biggest problems. 

f) Don't ignore a problem. 

Identifying a problem and tolerating it is like not identifying it. 

3. Identify problems' root causes 

a) Decide "what to do" after assessing "what is." 

"A good diagnosis takes 15 to 60 minutes, depending on its accuracy and complexity. [...] Like principles, root causes recur in different situations. 

b) Separate proximate and root causes. 

"You can only solve problems by removing their root causes, and to do that, you must distinguish symptoms from disease." 

c) Knowing someone's (or your own) personality can help you predict their behavior. 

4. Design plans that will get you around the problems 

a) Retrace your steps. 

Analyze your past to determine your future. 

b) Consider your problem a machine's output. 

Consider how to improve your machine. It's a game then. 

c) There are many ways to reach your goals. 

Find a solution. 

d) Visualize who will do what in your plan like a movie script. 

Consider your movie's actors and script's turning points, then act accordingly. The game continues. 

e) Document your plan so others can judge your progress. 

Accountability boosts success. 

f) Know that a good plan doesn't take much time. 

The execution is usually the hardest part, but most people either don't have a plan or keep changing it. Don't drive while building the car. Build it first, because it'll be bumpy. 

5. Do what is necessary to push through the plans to get results 

a) Great planners without execution fail. 

Life is won with more than just planning. Similarly, practice without talent beats talent without practice. 

b) Work ethic is undervalued. 

Hyper-productivity is praised in corporate America, even if it leads nowhere. To get things done, use checklists, fewer emails, and more desk time. 

c) Set clear metrics to ensure plan adherence. 

I've written about the OKR strategy for organizations with multiple people here. If you're on your own, I recommend the Wheel of Life approach. Both systems start with goals and tasks to achieve them. Then start executing on a realistic timeline. 

If you find solutions, weaknesses don't matter. 

Everyone's weak. You, me, Gates, Dalio, even Musk. Nobody will be great at all 5 steps of the system because no one can think in all the ways required. Some are good at analyzing and diagnosing but bad at executing. Some are good planners but poor communicators. Others lack self-discipline. 

Stay humble and ask for help when needed. Nobody has ever succeeded 100% on their own, without anyone else's help. That's the paradox of individual success: teamwork is the only way to get there. 

Most people won't have the skills to execute even the best plan. You can get missing skills in two ways: 

1. Self-taught (time-consuming) 

2. Others' (requires humility) light

On knowing what to do with your life 

“Some people have good mental maps and know what to do on their own. Maybe they learned them or were blessed with common sense. They have more answers than others. Others are more humble and open-minded. […] Open-mindedness and mental maps are most powerful.” — Ray Dalio 

I've always known what I wanted to do, so I'm lucky. I'm almost 30 and have always had trouble executing. Good thing I never stopped experimenting, but I never committed to anything long-term. I jumped between projects. I decided 3 years ago to stick to one project for at least 6 months and haven't looked back. 

Maybe you're good at staying focused and executing, but you don't know what to do. Maybe you have none of these because you haven't found your purpose. Always try new projects and talk to as many people as possible. It will give you inspiration and ideas and set you up for success. 

There is almost always a way to achieve a crazy goal or idea. 

Enjoy the journey, whichever path you take.

His regular regimen teaches stress management.

In 1995, an Indian graduate visited the US. He obtained a scholarship to Stanford after graduating from IIT with a silver medal. First flight. His ticket cost a year's income. His head was full.

Pichai Sundararajan is his full name. He became Google's CEO and a world leader. Mr. Pichai transformed technology and inspired millions to dream big.

This article reveals his daily schedule.

Mornings

While many of us dread Mondays, Mr. Pichai uses the day to contemplate.

A typical Indian morning. He awakens between 6:30 and 7 a.m. He avoids working out in the mornings.

Mr. Pichai oversees the internet, but he reads a real newspaper every morning.

Pichai mentioned that he usually enjoys a quiet breakfast during which he reads the news to get a good sense of what’s happening in the world. Pichai often has an omelet for breakfast and reads while doing so. The native of Chennai, India, continues to enjoy his daily cup of tea, which he describes as being “very English.”

Pichai starts his day. BuzzFeed's Mat Honan called the CEO Banana Republic dad.

Overthinking in the morning is a bad idea. It's crucial to clear our brains and give ourselves time in the morning before we hit traffic.

Mr. Pichai's morning ritual shows how to stay calm. Wharton Business School found that those who start the day calmly tend to stay that way. It's worth doing regularly.

And he didn't forget his roots.

Afternoons

He has a busy work schedule, as you can imagine. Running one of the world's largest firm takes time, energy, and effort. He prioritizes his work. Monitoring corporate performance and guaranteeing worker efficiency.

Sundar Pichai spends 7-8 hours a day to improve Google. He's noted for changing the company's culture. He wants to boost employee job satisfaction and performance.

His work won him recognition within the company.

Pichai received a 96% approval rating from Glassdoor users in 2017.

Mr. Pichai stresses work satisfaction. Each day is a new canvas for him to find ways to enrich people's job and personal lives.

His work offers countless lessons. According to several profiles and press sources, the Google CEO is a savvy negotiator. Mr. Pichai's success came from his strong personality, work ethic, discipline, simplicity, and hard labor.

Evenings

His evenings are spent with family after a busy day. Sundar Pichai's professional and personal lives are balanced. Sundar Pichai is a night owl who re-energizes about 9 p.m.

However, he claims to be most productive after 10 p.m., and he thinks doing a lot of work at that time is really useful. But he ensures he sleeps for around 7–8 hours every day. He enjoys long walks with his dog and enjoys watching NSDR on YouTube. It helps him in relaxing and sleep better.

His regular routine teaches us what? Work wisely, not hard, discipline, vision, etc. His stress management is key. Leading one of the world's largest firm with 85,000 employees is scary.

The pressure to achieve may ruin a day. Overworked employees are more likely to make mistakes or be angry with coworkers, according to the Family Work Institute. They can't handle daily problems, making the house more stressful than the office.

Walking your dog, having fun with friends, and having hobbies are as vital as your office.

"Don't let technology control you; manage your phone."

"Don't become a slave to technology," said Richard Branson. "Manage your phone, don't let it manage you."

Unfortunately, most people are addicted to smartphones.

Worrying smartphone statistics:

• 46% of smartphone users spend 5–6 hours daily on their device.

• The average adult spends 3 hours 54 minutes per day on mobile devices.

• We check our phones 150–344 times per day (every 4 minutes).

• During the pandemic, children's daily smartphone use doubled.

Having a list of productive, healthy, and fulfilling replacement activities is an effective way to reduce smartphone use.

The more you practice these smartphone replacements, the less time you'll waste.

Skills Development

Most people say they 'don't have time' to learn new skills or read more. Lazy justification. The issue isn't time, but time management. Distractions and low-quality entertainment waste hours every day.

The majority of time is spent in low-quality ways, according to Richard Koch, author of The 80/20 Principle.

What if you swapped daily phone scrolling for skill-building?

There are dozens of skills to learn, from high-value skills to make more money to new languages and party tricks.

Learning a new skill will last for years, if not a lifetime, compared to scrolling through your phone.

Watch Docs

Love documentaries. It's educational and relaxing. A good documentary helps you understand the world, broadens your mind, and inspires you to change.

Recent documentaries I liked include:

• 14 Peaks: Nothing Is Impossible

• The Social Dilemma

• Jim & Andy: The Great Beyond

• Fantastic Fungi

Make money online

If you've ever complained about not earning enough money, put away your phone and get to work.

Instead of passively consuming mobile content, start creating it. Create something worthwhile. Freelance.

Internet makes starting a business or earning extra money easier than ever.

(Grand)parents didn't have this. Someone made them work 40+ hours. Few alternatives existed.

Today, all you need is internet and a monetizable skill. Use the internet instead of letting it distract you. Profit from it.

Bookworm

Jack Canfield, author of Chicken Soup For The Soul, said, "Everyone spends 2–3 hours a day watching TV." If you read that much, you'll be in the top 1% of your field."

Few people have more than two hours per day to read.

If you read 15 pages daily, you'd finish 27 books a year (as the average non-fiction book is about 200 pages).

Jack Canfield's quote remains relevant even though 15 pages can be read in 20–30 minutes per day. Most spend this time watching TV or on their phones.

What if you swapped 20 minutes of mindless scrolling for reading? You'd gain knowledge and skills.

Favorite books include:

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

• The War of Art — Steven Pressfield

• The Psychology of Money — Morgan Housel

• A New Earth — Eckart Tolle

Get Organized

All that screen time could've been spent organizing. It could have been used to clean, cook, or plan your week.

If you're always 'behind,' spend 15 minutes less on your phone to get organized.

"Give me six hours to chop down a tree, and I'll spend the first four sharpening the ax," said Abraham Lincoln. Getting organized is like sharpening an ax, making each day more efficient.

Creativity

Why not be creative instead of consuming others'? Do something creative, like:

• Painting

• Musically

• Photography\sWriting

• Do-it-yourself

• Construction/repair

Creative projects boost happiness, cognitive functioning, and reduce stress and anxiety. Creative pursuits induce a flow state, a powerful mental state.

This contrasts with smartphones' effects. Heavy smartphone use correlates with stress, depression, and anxiety.

Hike

People spend 90% of their time indoors, according to research. This generation is the 'Indoor Generation'

We lack an active lifestyle, fresh air, and vitamin D3 due to our indoor lifestyle (generated through direct sunlight exposure). Mental and physical health issues result.

Put away your phone and get outside. Go on nature walks. Explore your city on foot (or by bike, as we do in Amsterdam) if you live in a city. Move around! Outdoors!

You can't spend your whole life staring at screens.

Podcasting

Okay, a smartphone is needed to listen to podcasts. When you use your phone to get smarter, you're more productive than 95% of people.

Favorite podcasts:

• The Pomp Podcast (about cryptocurrencies)

• The Joe Rogan Experience

• Kwik Brain (by Jim Kwik)

Podcasts can be enjoyed while walking, cleaning, or doing laundry. Win-win.

Journalize

I find journaling helpful for mental clarity. Writing helps organize thoughts.

Instead of reading internet opinions, comments, and discussions, look inward. Instead of Twitter or TikTok, look inward.

“It never ceases to amaze me: we all love ourselves more than other people, but care more about their opinion than our own.” — Marcus Aurelius

Give your mind free reign with pen and paper. It will highlight important thoughts, emotions, or ideas.

Never write for another person. You want unfiltered writing. So you get the best ideas.

Find your best hobbies

List your best hobbies. I guarantee 95% of people won't list smartphone scrolling.

It's often low-quality entertainment. The dopamine spike is short-lived, and it leaves us feeling emotionally 'empty'

High-quality leisure sparks happiness. They make us happy and alive. Everyone has different interests, so these activities vary.

My favorite quality hobbies are:

• Nature walks (especially the mountains)

• Video game party

• Watching a film with my girlfriend

• Gym weightlifting

• Complexity learning (such as the blockchain and the universe)

This brings me joy. They make me feel more fulfilled and 'rich' than social media scrolling.

Make a list of your best hobbies to refer to when you're spending too much time on your phone.

Product game mindsets? How do these vary from Project mindset?

1950s spawned the Iron Triangle. Project people everywhere know and live by it. In stakeholder meetings, it is used to stretch the timeframe, request additional money, or reduce scope.

Quality was added to this triangle as things matured.

Quality was intended to be transformative, but none of these principles addressed why we conduct projects.

Value and benefits are key.

Product value is quantified by ROI, revenue, profit, savings, or other metrics. For me, every project or product delivery is about value.

Most project managers, especially those schooled 5-10 years or more ago (thousands working in huge corporations worldwide), understand the world in terms of the iron triangle. What does that imply? They worry about:

a) enough time to get the thing done.

b) have enough resources (budget) to get the thing done.

c) have enough scope to fit within (a) and (b) >> note, they never have too little scope, not that I have ever seen! although, theoretically, this could happen.

Boom—iron triangle.

To make the triangle function, project managers will utilize formal governance (Steering) to move those things. Increase money, scope, or both if time is short. Lacking funds? Increase time, scope, or both.

In current product development, shifting each item considerably may not yield value/benefit.

Even terrible. This approach will fail because it deprioritizes Value/Benefit by focusing the major stakeholders (Steering participants) and delivery team(s) on Time, Scope, and Budget restrictions.

Pre-agile, this problem was terrible. IT projects failed wildly. History is here.

Value, or benefit, is central to the product method. Product managers spend most of their time planning value-delivery paths.

Product people consider risk, schedules, scope, and budget, but value comes first. Let me illustrate.

Imagine managing internal products in an enterprise. Your core customer team needs a rapid text record of a chat to fix a problem. The consumer wants a feature/features added to a product you're producing because they think it's the greatest spot.

Project-minded, I may say;

Ok, I have budget as this is an existing project, due to run for a year. This is a new requirement to add to the features we’re already building. I think I can keep the deadline, and include this scope, as it sounds related to the feature set we’re building to give the desired result”.

This attitude repeats Scope, Time, and Budget.

Since it meets those standards, a project manager will likely approve it. If they have a backlog, they may add it and start specking it out assuming it will be built.

Instead, think like a product;

What problem does this feature idea solve? Is that problem relevant to the product I am building? Can that problem be solved quicker/better via another route ? Is it the most valuable problem to solve now? Is the problem space aligned to our current or future strategy? or do I need to alter/update the strategy?

A product mindset allows you to focus on timing, resource/cost, feasibility, feature detail, and so on after answering the aforementioned questions.

The above oversimplifies because

Leadership in discovery

Project managers are facilitators of ideas. This is as far as they normally go in the ‘idea’ space.

Business Requirements collection in classic project delivery requires extensive upfront documentation.

Agile project delivery analyzes requirements iteratively.

However, the project manager is a facilitator/planner first and foremost, therefore topic knowledge is not expected.

I mean business domain, not technical domain (to confuse matters, it is true that in some instances, it can be both technical and business domains that are important for a single individual to master).

Product managers are domain experts. They will become one if they are training/new.

They lead discovery.

Product Manager-led discovery is much more than requirements gathering.

Requirements gathering involves a Business Analyst interviewing people and documenting their requests.

The project manager calculates what fits and what doesn't using their Iron Triangle (presumably in their head) and reports back to Steering.

If this requirements-gathering exercise failed to identify requirements, what would a project manager do? or bewildered by project requirements and scope?

They would tell Steering they need a Business SME or Business Lead assigning or more of their time.

Product discovery requires the Product Manager's subject knowledge and a new mindset.

How should a Product Manager handle confusing requirements?

Product Managers handle these challenges with their talents and tools. They use their own knowledge to fill in ambiguity, but they have the discipline to validate those assumptions.

To define the problem, they may perform qualitative or quantitative primary research.

They might discuss with UX and Engineering on a whiteboard and test assumptions or hypotheses.

Do Product Managers escalate confusing requirements to Steering/Senior leaders? They would fix that themselves.

Product managers raise unclear strategy and outcomes to senior stakeholders. Open talks, soft skills, and data help them do this. They rarely raise requirements since they have their own means of handling them without top stakeholder participation.

Discovery is greenfield, exploratory, research-based, and needs higher-order stakeholder management, user research, and UX expertise.

Product Managers also aid discovery. They lead discovery. They will not leave customer/user engagement to a Business Analyst. Administratively, a business analyst could aid. In fact, many product organizations discourage business analysts (rely on PM, UX, and engineer involvement with end-users instead).

The Product Manager must drive user interaction, research, ideation, and problem analysis, therefore a Product professional must be skilled and confident.

Creating vs. receiving and having an entrepreneurial attitude

Product novices and project managers focus on details rather than the big picture. Project managers prefer spreadsheets to strategy whiteboards and vision statements.

These folks ask their manager or senior stakeholders, "What should we do?"

They then elaborate (in Jira, in XLS, in Confluence or whatever).

They want that plan populated fast because it reduces uncertainty about what's going on and who's supposed to do what.

Skilled Product Managers don't only ask folks Should we?

They're suggesting this, or worse, Senior stakeholders, here are some options. After asking and researching, they determine what value this product adds, what problems it solves, and what behavior it changes.

Therefore, to move into Product, you need to broaden your view and have courage in your ability to discover ideas, find insightful pieces of information, and collate them to form a valuable plan of action. You are constantly defining RoI and building Business Cases, so much so that you no longer create documents called Business Cases, it is simply ingrained in your work through metrics, intelligence, and insights.

Product Management is not a free lunch.

Plateless.

Plates and food must be prepared.

In conclusion, Product Managers must make at least three mentality shifts:

1. You put value first in all things. Time, money, and scope are not as important as knowing what is valuable.

2. You have faith in the field and have the ability to direct the search. YYou facilitate, but you don’t just facilitate. You wouldn't want to limit your domain expertise in that manner.

3. You develop concepts, strategies, and vision. You are not a waiter or an inbox where other people can post suggestions; you don't merely ask folks for opinion and record it. However, you excel at giving things that aren't clearly spoken or written down physical form.

My colleague Ilana Ovental and I examined pandemic media coverage of education at the end of last year. That analysis examined coverage changes. We tracked K-12 topic attention over the previous two decades using Lexis Nexis. See the results here.

I was struck by how cleanly the past two decades can be divided up into three (or three and a half) eras of school reform—a framing that can help us comprehend where we are and how we got here. In a time when epidemic, political unrest, frenetic news cycles, and culture war can make six months seem like a lifetime, it's worth pausing for context.

If you look at the peaks in the above graph, the 21st century looks to be divided into periods. The decade-long rise and fall of No Child Left Behind began during the Bush administration. In a few years, NCLB became the dominant K-12 framework. Advocates and financiers discussed achievement gaps and measured success with AYP.

NCLB collapsed under the weight of rigorous testing, high-stakes accountability, and a race to the bottom by the Obama years. Obama's Race to the Top garnered attention, but its most controversial component, the Common Core State Standards, rose quickly.

Academic standards replaced assessment and accountability. New math, fiction, and standards were hotly debated. Reformers and funders chanted worldwide benchmarking and systems interoperability.

We went from federally driven testing and accountability to government encouraged/subsidized/mandated (pick your verb) reading and math standardization. Last year, Checker Finn and I wrote The End of School Reform? The 2010s populist wave thwarted these objectives. The Tea Party, Occupy Wall Street, Black Lives Matter, and Trump/MAGA all attacked established institutions.

Consequently, once the Common Core fell, no alternative program emerged. Instead, school choice—the policy most aligned with populist suspicion of institutional power—reached a half-peak. This was less a case of choice erupting to prominence than of continuous growth in a vacuum. Even with Betsy DeVos' determined, controversial efforts, school choice received only half the media attention that NCLB and Common Core did at their heights.

Recently, culture clash-fueled attention to race-based curriculum and pedagogy has exploded (all playing out under the banner of critical race theory). This third, culture war-driven wave may not last as long as the other waves.

Even though I don't understand it, the move from slow-building policy debate to fast cultural confrontation over two decades is notable. I don't know if it's cyclical or permanent, or if it's about schooling, media, public discourse, or all three.

One final thought: After doing this work for decades, I've noticed how smoothly advocacy groups, associations, and other activists adapt to the zeitgeist. In 2007, mission statements focused on accomplishment disparities. Five years later, they promoted standardization. Language has changed again.

Part of this is unavoidable and healthy. Chasing currents can also make companies look unprincipled, promote scepticism, and keep them spinning the wheel. Bearing in mind that these tides ebb and flow may give educators, leaders, and activists more confidence to hold onto their values and pause when they feel compelled to follow the crowd.

This is how to build a car while driving.

Building a high-growth startup is compared to building a car while it's speeding down the highway.

How to plan without going crazy? Or, without losing team, board, and investor buy-in?

I just delivered our company's product roadmap for the rest of the year. Complete. Thorough. Page-long. I'm optimistic about its chances of surviving as everything around us changes, from internal priorities to the global economy.

It's tricky. This isn't the first time I've created a startup roadmap. I didn't invent a document. It took time to deliver a document that will be relevant for months.

Goals matter.

Although they never change, goals are rarely understood.

This is the third in a series about a startup's unique roadmapping needs. Velocity is the intensity at which a startup must produce to survive.

A high-growth startup moves at breakneck speed, which I alluded to when I said priorities and economic factors can change daily or weekly.

At that speed, a startup's roadmap must be flexible, bend but not break, and be brief and to the point. I can't tell you how many startups and large companies develop a product roadmap every quarter and then tuck it away.

Big, wealthy companies can do this. It's suicide for a startup.

The drawer thing happens because startup product roadmaps are often valid for a short time. The roadmap is a random list of features prioritized by different company factions and unrelated to company goals.

It's not because the goals changed that a roadmap is shelved or ignored. Because the company's goals were never communicated or documented in the context of its product.

In the previous post, I discussed how to turn company goals into a product roadmap. In this post, I'll show you how to make a one-page startup roadmap.

In a future post, I'll show you how to follow this roadmap. This roadmap helps you track company goals, something a roadmap must do.

Be vague for growth, but direct for execution.

Here's my plan. The real one has more entries and more content in each.

Let's discuss smaller boxes.

Product developers and engineers know that the further out they predict, the more wrong they'll be. When developing the product roadmap, this rule is ignored. Then it bites us three, six, or nine months later when we haven't even started.

Why do we put everything in a product roadmap like a project plan?

Yes, I know. We use it when the product roadmap isn't goal-based.

A goal-based roadmap begins with a document that outlines each goal's idea, execution, growth, and refinement.

Once the goals are broken down into epics, initiatives, projects, and programs, only the idea and execution phases should be modeled. Any goal growth or refinement items should be vague and loosely mapped.

Why? First, any idea or execution-phase goal will result in growth initiatives that are unimaginable today. Second, internal priorities and external factors will change, but the goals won't. Locking items into calendar slots reduces flexibility and forces deviation from the single source of truth.

No soothsayers. Predicting the future is pointless; just prepare.

A map is useless if you don't know where you're going.

As we speed down the road, the car and the road will change. Goals define the destination.

This quarter and next quarter's roadmap should be set. After that, you should track destination milestones, not how to get there.

When you do that, even the most critical investors will understand the roadmap and buy in. When you track progress at the end of the quarter and revise your roadmap, the destination won't change.