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.

I've summarized each.

Anne Lamott said books are important. Books help us understand ourselves and our behavior. They teach us about community, friendship, and death.

I read. One of my few life-changing habits. 100+ books a year improve my life. I'll list life-changing books you can read in a day. I hope you like them too.

Let's get started!

1) Seneca's Letters from a Stoic

One of my favorite philosophy books. Ryan Holiday, Naval Ravikant, and other prolific readers recommend it.

Seneca wrote 124 letters at the end of his life after working for Nero. Death, friendship, and virtue are discussed.

It's worth rereading. When I'm in trouble, I consult Seneca.

It's brief. The book could be read in one day. However, use it for guidance during difficult times.

My favorite book quotes:

• Many men find that becoming wealthy only alters their problems rather than solving them.

• You will never be poor if you live in harmony with nature; you will never be wealthy if you live according to what other people think.

• We suffer more frequently in our imagination than in reality; there are more things that are likely to frighten us than to crush us.

2) Steven Pressfield's book The War of Art

I’ve read this book twice. I'll likely reread it before 2022 is over.

The War Of Art is the best productivity book. Steven offers procrastination-fighting tips.

Writers, musicians, and creative types will love The War of Art. Workplace procrastinators should also read this book.

My favorite book quotes:

• The act of creation is what matters most in art. Other than sitting down and making an effort every day, nothing else matters.

• Working creatively is not a selfish endeavor or an attempt by the actor to gain attention. It serves as a gift for all living things in the world. Don't steal your contribution from us. Give us everything you have.

• Fear is healthy. Fear is a signal, just like self-doubt. Fear instructs us on what to do. The more terrified we are of a task or calling, the more certain we can be that we must complete it.

3) Darren Hardy's The Compound Effect

The Compound Effect offers practical tips to boost productivity by 10x.

The author believes each choice shapes your future. Pizza may seem harmless. However, daily use increases heart disease risk.

Positive outcomes too. Daily gym visits improve fitness. Reading an hour each night can help you learn. Writing 1,000 words per day would allow you to write a novel in under a year.

Your daily choices affect compound interest and your future. Thus, better habits can improve your life.

My favorite book quotes:

• Until you alter a daily habit, you cannot change your life. The key to your success can be found in the actions you take each day.

• The hundreds, thousands, or millions of little things are what distinguish the ordinary from the extraordinary; it is not the big things that add up in the end.

• Don't worry about willpower. Time to use why-power. Only when you relate your decisions to your aspirations and dreams will they have any real meaning. The decisions that are in line with what you define as your purpose, your core self, and your highest values are the wisest and most inspiring ones. To avoid giving up too easily, you must want something and understand why you want it.

Skip this if you don't want to discover why your lively, no-brainer pitch isn't making $10k a month.

You don't want to be repulsive as an entrepreneur or anyone else. Making friends, influencing people, and converting strangers into customers will be difficult if your words evoke disgust, distrust, or disrespect. You may be one of many entrepreneurs who do this obliviously and involuntarily.

I've had to master selling my skills to recruiters (to land 6-figure jobs on Wall Street), selling companies to buyers in M&A transactions, and selling my own companies' products to strangers-turned-customers. I probably committed every cardinal sin of sales repulsion before realizing it was me or my poor salesmanship strategy.

If you're launching a new business, frustrated by low conversion rates, or just curious if you're repelling customers, read on to identify (and avoid) the 6 fatal errors that can kill any sales pitch.

1. The first indication

So many people fumble before they even speak because they assume their role is to convince the buyer. In other words, they expect to pressure, arm-twist, and combat objections until they convert the buyer. Actuality, the approach stinks of disgust, and emotionally-aware buyers would feel "gross" immediately.

Instead of trying to persuade a customer to buy, ask questions that will lead them to do so on their own. When a customer discovers your product or service on their own, they need less outside persuasion. Why not position your offer in a way that leads customers to sell themselves on it?

2. A flawless performance

Are you memorizing a sales script, tweaking video testimonials, and expunging historical blemishes before hitting "publish" on your new campaign? If so, you may be hurting your conversion rate.

Perfection may be a step too far and cause prospects to mistrust your sincerity. Become a great conversationalist to boost your sales. Seriously. Being charismatic is hard without being genuine and showing a little vulnerability.

People like vulnerability, even if it dents your perfect facade. Show the customer's stuttering testimonial. Open up about your or your company's past mistakes (and how you've since improved). Make your sales pitch a two-way conversation. Let the customer talk about themselves to build rapport. Real people sell, not canned scripts and movie-trailer testimonials.

If marketing or sales calls feel like a performance, you may be doing something wrong or leaving money on the table.

3. Your greatest phobia

Three minutes into prospect talks, I'd start sweating. I was talking 100 miles per hour, covering as many bases as possible to avoid the ones I feared. I knew my then-offering was inadequate and my firm had fears I hadn't addressed. So I word-vomited facts, features, and everything else to avoid the customer's concerns.

Do my prospects know I'm insecure? Maybe not, but it added an unnecessary and unhelpful layer of paranoia that kept me stressed, rushed, and on edge instead of connecting with the prospect. Skirting around a company, product, or service's flaws or objections is a poor, temporary, lazy (and cowardly) decision.

How can you project confidence and trust if you're afraid? Before you make another sales call, face your shortcomings, weak points, and objections. Your company won't be everyone's cup of tea, but you should have answers to every question or objection. You should be your business's top spokesperson and defender.

4. The unintentional apologies

Have you ever begged for a sale? I'm going to say no, however you may be unknowingly emitting sorry, inferior, insecure energy.

Young founders, first-time entrepreneurs, and those with severe imposter syndrome may elevate their target customer. This is common when trying to get first customers for obvious reasons.

• Since you're truly new at this, you naturally lack experience.

• You don't have the self-confidence boost of thousands or hundreds of closed deals or satisfied client results to remind you that your good or service is worthwhile.

• Getting those initial few clients seems like the most difficult task, as if doing so will decide the fate of your company as a whole (it probably won't, and you shouldn't actually place that much emphasis on any one transaction).

Customers can smell fear, insecurity, and anxiety just like they can smell B.S. If you believe your product or service improves clients' lives, selling it should feel like a benevolent act of service, not a sleazy money-grab. If you're a sincere entrepreneur, prospects will believe your proposition; if you're apprehensive, they'll notice.

Approach every sale as if you're fine with or without it. This has improved my salesmanship, marketing skills, and mental health. When you put pressure on yourself to close a sale or convince a difficult prospect "or else" (your company will fail, your rent will be late, your electricity will be cut), you emit desperation and lower the quality of your pitch. There's no point.

5. The endless promises

We've all read a million times how to answer or disprove prospects' arguments and add extra incentives to speed or secure the close. Some objections shouldn't be refuted. What if I told you not to offer certain incentives, bonuses, and promises? What if I told you to walk away from some prospects, even if it means losing your sales goal?

If you market to enough people, make enough sales calls, or grow enough companies, you'll encounter prospects who can't be satisfied. These prospects have endless questions, concerns, and requests for more, more, more that you'll never satisfy. These people are a distraction, a resource drain, and a test of your ability to cut losses before they erode your sanity and profit margin.

To appease or convert these insatiably needy, greedy Nellies into customers, you may agree with or acquiesce to every request and demand — even if you can't follow through. Once you overpromise and answer every hole they poke, their trust in you may wane quickly.

Telling a prospect what you can't do takes courage and integrity. If you're honest, upfront, and willing to admit when a product or service isn't right for the customer, you'll gain respect and positive customer experiences. Sometimes honesty is the most refreshing pitch and the deal-closer.

6. No matter what

Have you ever said, "I'll do anything to close this sale"? If so, you've probably already been disqualified. If a prospective customer haggles over a price, requests a discount, or continues to wear you down after you've made three concessions too many, you have a metal hook in your mouth, not them, and it may not end well. Why?

If you're so willing to cut a deal that you cut prices, comp services, extend payment plans, waive fees, etc., you betray your own confidence that your product or service was worth the stated price. They wonder if anyone is paying those prices, if you've ever had a customer (who wasn't a blood relative), and if you're legitimate or worth your rates.

Once a prospect senses that you'll do whatever it takes to get them to buy, their suspicions rise and they wonder why.

• Why are you cutting pricing if something is wrong with you or your service?

• Why are you so desperate for their sale?

• Why aren't more customers waiting in line to pay your pricing, and if they aren't, what on earth are they doing there?

That's what a prospect thinks when you reveal your lack of conviction, desperation, and willingness to give up control. Some prospects will exploit it to drain you dry, while others will be too frightened to buy from you even if you paid them.

Walking down a two-way street. Be casual.

If we track each act of repulsion to an uneasiness, fear, misperception, or impulse, it's evident that these sales and marketing disasters were forced communications. Stiff, imbalanced, divisive, combative, bravado-filled, and desperate. They were unnatural and accepted a power struggle between two sparring, suspicious, unequal warriors, rather than a harmonious oneness of two natural, but opposite parties shaking hands.

Sales should be natural, harmonious. Sales should feel good for both parties, not like one party is having their arm twisted.

You may be doing sales wrong if it feels repulsive, icky, or degrading. If you're thinking cringe-worthy thoughts about yourself, your product, service, or sales pitch, imagine what you're projecting to prospects. Don't make it unpleasant, repulsive, or cringeworthy.

Don't overcomplicate to-do lists. DWTS (Done, Waiting, Top 3, Soon) organizes your to-dos.

How Are You Going to Manage Everything?

Modern America is busy. Work involves meetings. Anytime, Slack communications arrive. Many software solutions offer a @-mention notification capability. Emails.

Work obligations continue. At home, there are friends, family, bills, chores, and fun things.

How are you going to keep track of it all? Enter the todo list. It’s been around forever. It’s likely to stay forever in some way, shape, or form.

Everybody has their own system. You probably modified something from middle school. Post-its? Maybe it’s an app? Maybe both, another system, or none.

I suggest a format that has worked for me in 15 years of professional and personal life.

Try it out and see if it works for you. If not, no worries. You do you! Hopefully though you can learn a thing or two, and I from you too.

It is merely a Google Doc, yes.

It's a giant list. One task per line. Indent subtasks on a new line. Add or move new tasks as needed.

I recommend using Google Docs. It's easy to use and flexible for structuring.

Prioritizing these tasks is key. I organize them using DWTS (Done, Waiting, Top 3, Soon). Chronologically is good because it implicitly provides both a priority (high, medium, low) and an ETA (now, soon, later).

Yes, I recognize the similarities to DWTS (Dancing With The Stars) TV Show. Although I'm not a fan, it's entertaining. The acronym is easy to remember and adds fun to something dull.

What each section contains

Done

All tasks' endpoint. Finish here. Don't worry about it again.

Waiting

You're blocked and can't continue. Blocked tasks usually need someone. Write Person Task so you know who's waiting.

Blocking tasks shouldn't last long. After a while, remind them kindly. If people don't help you out of kindness, they will if you're persistent.

Top 3

Mental focus areas. These can be short- to mid-term goals or recent accomplishments. 2 to 5 is a good number to stay focused.

Top 3 reminds us to prioritize. If they don't fit your Top 3 goals, delay them.

Every 1:1 at work is a project update. Another chance to list your top 3. You should know your Top 3 well and be able to discuss them confidently.

Soon

Here's your short-term to-do list. Rank them from highest to lowest.

I usually subdivide it with empty lines. First is what I have to do today, then week, then month. Subsections can be arranged however you like.

Inventories by Concept

Tasks that aren’t in your short or medium future go into the backlog. 
Eventually you’ll complete these tasks, assign them to someone else, or mark them as “wont’ do” (like done but in another sense).

Backlog tasks don't need to be organized chronologically because their timing and priority may change. Theme-organize them. When planning/strategic, you can choose themes to focus on, so future top 3 topics.

More Tips on Todos

Decide Upon a Morning Goal

Morning routines are universal. Coffee and Wordle. My to-do list is next. Two things:

• As needed, update the to-do list: based on the events of yesterday and any fresh priorities.

• Pick a few jobs to complete today: Pick a few goals that you know you can complete today. Push the remainder below and move them to the top of the Soon section. I typically select a few tasks I am confident I can complete along with one stretch task that might extend into tomorrow.

Finally. By setting and achieving small goals every day, you feel accomplished and make steady progress on medium and long-term goals.

Tech companies call this a daily standup. Everyone shares what they did yesterday, what they're doing today, and any blockers. The name comes from a tradition of holding meetings while standing up to keep them short. Even though it's virtual, everyone still wants a quick meeting.

Your team may or may not need daily standups. Make a daily review a habit with your coffee.

Review Backwards & Forwards on a regular basis

While you're updating your to-do list daily, take time to review it.

Review your Done list. Remember things you're proud of and things that could have gone better. Your Done list can be long. Archive it so your main to-do list isn't overwhelming.

Future-gaze. What you considered important may no longer be. Reorder tasks. Backlog grooming is a workplace term.

Backwards-and-forwards reviews aren't required often. Every 3-6 months is fine. They help you see the forest as often as the trees.

Final Remarks

Keep your list simple. Done, Waiting, Top 3, Soon. These are the necessary sections. If you like, add more subsections; otherwise, keep it simple.

I recommend a morning review. By having clear goals and an action-oriented attitude, you'll be successful.