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.

Sometimes doing everything correctly isn't enough.

In 2020, I could fix my life.

After failing to start a business, I owed $40,000 and had no work.

A $1.2 billion startup on the cusp of going public pulled me up.

Ironically, it was getting ready for an epic fall — with the world watching.

Life sometimes helps. Without a base, even the strongest fall. A corporation that did everything right failed 3 months after going public.

First-row view.

Apple is the creator of Adore.

Out of respect, I've altered the company and employees' names in this account, despite their failure.

Although being a publicly traded company, it may become obvious.

We’ll call it “Adore” — a revolutionary concept in retail shopping.

Two Apple execs established Adore in 2014 with a focus on people-first purchasing.

Jon and Tim:

• The concept for the stylish Apple retail locations you see today was developed by retail expert Jon Swanson, who collaborated closely with Steve Jobs.

• Tim Cruiter is a graphic designer who produced the recognizable bouncing lamp video that appears at the start of every Pixar film.

The dynamic duo realized their vision.

“What if you could combine the convenience of online shopping with the confidence of the conventional brick-and-mortar store experience.”

Adore's mobile store concept combined traditional retail with online shopping.

Adore brought joy to 70+ cities and 4 countries over 7 years, including the US, Canada, and the UK.

Being employed on the ground floor, with world dominance and IPO on the horizon, was exciting.

I started as an Adore Expert.

I delivered cell phones, helped consumers set them up, and sold add-ons.

As the company grew, I became a Virtual Learning Facilitator and trained new employees across North America using Zoom.

In this capacity, I gained corporate insider knowledge. I worked with the creative team and Jon and Tim.

It's where I saw company foundation fissures. Despite appearances, investors were concerned.

The business strategy was ground-breaking.

Even after seeing my employee stocks fall from a home down payment to $0 (when Adore filed for bankruptcy), it's hard to pinpoint what went wrong.

Solid business model, well-executed.

Jon and Tim's chase for public funding ended in glory.

Here’s the business model in a nutshell:

Buying cell phones is cumbersome. You have two choices:

1. Online purchase: not knowing what plan you require or how to operate your device.

2. Enter a store, which can be troublesome and stressful.

Apple, AT&T, and Rogers offered Adore as a free delivery add-on. Customers could:

• Have their phone delivered by UPS or Canada Post in 1-2 weeks.

• Alternately, arrange for a person to visit them the same day (or sometimes even the same hour) to assist them set up their phone and demonstrate how to use it (transferring contacts, switching the SIM card, etc.).

Each Adore Expert brought a van with extra devices and accessories to customers.

Happy customers.

Here’s how Adore and its partners made money:

Adores partners appreciated sending Experts to consumers' homes since they improved customer satisfaction, average sale, and gadget returns.

**Telecom enterprises have low customer satisfaction. The average NPS is 30/100. Adore's global NPS was 80.

Adore made money by:

• a set cost for each delivery

• commission on sold warranties and extras

Consumer product applications seemed infinite.

A proprietary scheduling system (“The Adore App”), allowed for same-day, even same-hour deliveries.

It differentiates Adore.

They treated staff generously by:

• Options on stock

• health advantages

• sales enticements

• high rates per hour

Four-day workweeks were set by experts.

Being hired early felt like joining Uber, Netflix, or Tesla. We hoped the company's stocks would rise.

Exciting times.

I smiled as I greeted more than 1,000 new staff.

I spent a decade in retail before joining Adore. I needed a change.

After a leap of faith, I needed a lifeline. So, I applied for retail sales jobs in the spring of 2019.

The universe typically offers you what you want after you accept what you need. I needed a job to settle my debt and reach $0 again.

And the universe listened.

After being hired as an Adore Expert, I became a Virtual Learning Facilitator. Enough said.

After weeks of economic damage from the pandemic.

This employment let me work from home during the pandemic. It taught me excellent business skills.

I was active in brainstorming, onboarding new personnel, and expanding communication as we grew.

This job gave me vital skills and a regular paycheck during the pandemic.

It wasn’t until January of 2022 that I left on my own accord to try to work for myself again — this time, it’s going much better.

Adore was perfect. We valued:

• Connection

• Discovery

• Empathy

Everything we did centered on compassion, and we held frequent Justice Calls to discuss diversity and work culture.

The last day of onboarding typically ended in tears as employees felt like they'd found a home, as I had.

Like all nice things, the wonderful vibes ended.

First indication of distress

My first day at the workplace was great.

Fun, intuitive, and they wanted creative individuals, not salesman.

While sales were important, the company's vision was more important.

“To deliver joy through life-changing mobile retail experiences.”

Thorough, forward-thinking training. We had a module on intuition. It gave us role ownership.

We were flown cross-country for training, gave feedback, and felt like we made a difference. Multiple contacts responded immediately and enthusiastically.

The atmosphere was genuine.

Making money was secondary, though. Incredible service was a priority.

Jon and Tim answered new hires' questions during Zoom calls during onboarding. CEOs seldom meet new hires this way, but they seemed to enjoy it.

All appeared well.

But in late 2021, things started changing.

Adore's leadership changed after its IPO. From basic values to sales maximization. We lost communication and were forced to fend for ourselves.

Removed the training wheels.

It got tougher to gain instructions from those above me, and new employees told me their roles weren't as advertised.

External money-focused managers were hired.

Instead of creative types, we hired salespeople.

With a new focus on numbers, Adore's uniqueness began to crumble.

Via Zoom, hundreds of workers were let go.

So.

Early in 2022, mass Zoom firings were trending. A CEO firing 900 workers over Zoom went viral.

Adore was special to me, but it became a headline.

30 June 2022, Vice Motherboard published Watch as Adore's CEO Fires Hundreds.

It described a leaked video of Jon Swanson laying off all staff in Canada and the UK.

They called it a “notice of redundancy”.

The corporation couldn't pay its employees.

I loved Adore's underlying ideals, among other things. We called clients Adorers and sold solutions, not add-ons.

But, like anything, a company is only as strong as its weakest link. And obviously, the people-first focus wasn’t making enough money.

There were signs. The expansion was presumably a race against time and money.

Adore finally declared bankruptcy.

Adore declared bankruptcy 3 months after going public. It happened in waves, like any large-scale fall.

• Initial key players to leave were

• Then, communication deteriorated.

• Lastly, the corporate culture disintegrated.

6 months after leaving Adore, I received a letter in the mail from a Law firm — it was about my stocks.

Adore filed Chapter 11. I had to sue to collect my worthless investments.

I hoped those stocks will be valuable someday. Nope. Nope.

Sad, I sighed.

$1.2 billion firm gone.

I left the workplace 3 months before starting a writing business. Despite being mediocre, I'm doing fine.

I got up as Adore fell.

Finally, can we scale kindness?

I trust my gut. Changes at Adore made me leave before it sank.

Adores' unceremonious slide from a top startup to bankruptcy is astonishing to me.

The company did everything perfectly, in my opinion.

• first to market,

• provided excellent service

• paid their staff handsomely.

• was responsible and attentive to criticism

The company wasn't led by an egotistical eccentric. The crew had centuries of cumulative space experience.

I'm optimistic about the future of work culture, but is compassion scalable?

Prioritize big-ticket purchases

I've made several spending blunders. I get sick thinking about how much money I spent.

My financial mental model was poor back then.

Stoicism and mindfulness keep me from attaching to those feelings. It still hurts.

Until four or five years ago, I bought a new winter jacket every year.

Ten years ago, I spent twice as much. Now that I have a fantastic, warm winter parka, I don't even consider acquiring another one. No more spending. I'm not looking for jackets either.

Saving time and money by spending well is my thinking paradigm.

The philosophy is expressed in most languages. Cheap is expensive in the Netherlands. This applies beyond shopping.

In this essay, I will offer three examples of how this mental paradigm transformed my financial life.

Publishing books

In 2015, I presented and positioned my first book poorly.

I called the book Huge Life Success and made a funny Canva cover in 30 minutes. This:

That looks nothing like my present books. No logo or style. The book felt amateurish.

The book started bothering me a few weeks after publication. The advice was good, but it didn't appear professional. I studied the book business extensively.

I created a style for all my designs. Branding. Win Your Inner Wars was reissued a year later.

Title, cover, and description changed. Rearranging the chapters improved readability.

Seven years later, the book sells hundreds of copies a month. That taught me a lot.

Rushing to finish a project is enticing. Send it and move forward.

Avoid rushing everything. Relax. Develop your projects. Perform well. Perform the job well.

My first novel was underfunded and underworked. A bad book arrived. I then invested time and money in writing the greatest book I could.

That book still sells.

Traveling

I hate travel. Airports, flights, trains, and lines irritate me.

But, I enjoy traveling to beautiful areas.

I do it strangely. I make up travel rules. I never go to airports in summer. I hate being near airports on holidays. Unworthy.

No vacation packages for me. Those airline packages with a flight, shuttle, and hotel. I've had enough.

I try to avoid crowds and popular spots. July Paris? Nuts and bolts, please. Christmas in NYC? No, please keep me sane.

I fly business class behind. I accept upgrades upon check-in. I prefer driving. I drove from the Netherlands to southern Spain.

Thankfully, no lines. What if travel costs more? Thus? I enjoy it from the start. I start traveling then.

I rarely travel since I'm so difficult. One great excursion beats several average ones.

Personal effectiveness

New apps, tools, and strategies intrigue most productivity professionals.

No.

I researched years ago. I spent years investigating productivity in university.

I bought books, courses, applications, and tools. It was expensive and time-consuming.

Im finished. Productivity no longer costs me time or money. OK. I worked on it once and now follow my strategy.

I avoid new programs and systems. My stuff works. Why change winners?

Spending wisely saves time and money.

Spending wisely means spending once. Many people ignore productivity. It's understudied. No classes.

Some assume reading a few articles or a book is enough. Productivity is personal. You need a personal system.

Time invested is one-time. You can trust your system for life once you find it.

Concentrate on the expensive choices.

Life's short. Saving money quickly is enticing.

Spend less on groceries today. True. That won't fix your finances.

Adopt a lifestyle that makes you affluent over time. Consider major choices.

Are they causing long-term poverty? Are you richer?

Leasing cars comes to mind. The automobile costs a fortune today. The premium could accomplish a million nice things.

Focusing on important decisions makes life easier. Consider your future. You want to improve next year.

During the dot-com bust, I started my internet career. People used the internet intermittently to check email, plan travel, and do research. The average internet user spent 30 minutes online a day, compared to 7 today. To use the internet, you had to "log on" (most people still used dial-up), unlike today's always-on, high-speed mobile internet. In 2001, Amazon's market cap was $2.2B, 1/500th of what it is today. A study asked Americans if they'd adopt broadband, and most said no. They didn't see a need to speed up email, the most popular internet use. The National Academy of Sciences ranked the internet 13th among the 100 greatest inventions, below radio and phones. The internet was a cool invention, but it had limited uses and wasn't a good place to build a business. 

A small but growing movement of developers and founders believed the internet could be more than a read-only medium, allowing anyone to create and publish. This is web 2. The runner up name was read-write web. (These terms were used in prominent publications and conferences.) 

Web 2 concepts included letting users publish whatever they want ("user generated content" was a buzzword), social graphs, APIs and mashups (what we call composability today), and tagging over hierarchical navigation. Technical innovations occurred. A seemingly simple but important one was dynamically updating web pages without reloading. This is now how people expect web apps to work. Mobile devices that could access the web were niche (I was an avid Sidekick user). 

The contrast between what smart founders and engineers discussed over dinner and on weekends and what the mainstream tech world took seriously during the week was striking. Enterprise security appliances, essentially preloaded servers with security software, were a popular trend. Many of the same people would talk about "serious" products at work, then talk about consumer internet products and web 2. It was tech's biggest news. Web 2 products were seen as toys, not real businesses. They were hobbies, not work-related. 

There's a strong correlation between rich product design spaces and what smart people find interesting, which took me some time to learn and led to blog posts like "The next big thing will start out looking like a toy" Web 2's novel product design possibilities sparked dinner and weekend conversations. Imagine combining these features. What if you used this pattern elsewhere? What new product ideas are next? This excited people. "Serious stuff" like security appliances seemed more limited. 

The small and passionate web 2 community also stood out. I attended the first New York Tech meetup in 2004. Everyone fit in Meetup's small conference room. Late at night, people demoed their software and chatted. I have old friends. Sometimes I get asked how I first met old friends like Fred Wilson and Alexis Ohanian. These topics didn't interest many people, especially on the east coast. We were friends. Real community. Alex Rampell, who now works with me at a16z, is someone I met in 2003 when a friend said, "Hey, I met someone else interested in consumer internet." Rare. People were focused and enthusiastic. Revolution seemed imminent. We knew a secret nobody else did. 

My web 2 startup was called SiteAdvisor. When my co-founders and I started developing the idea in 2003, web security was out of control. Phishing and spyware were common on Internet Explorer PCs. SiteAdvisor was designed to warn users about security threats like phishing and spyware, and then, using web 2 concepts like user-generated reviews, add more subjective judgments (similar to what TrustPilot seems to do today). This staged approach was common at the time; I called it "Come for the tool, stay for the network." We built APIs, encouraged mashups, and did SEO marketing. 

Yahoo's 2005 acquisitions of Flickr and Delicious boosted web 2 in 2005. By today's standards, the amounts were small, around $30M each, but it was a signal. Web 2 was assumed to be a fun hobby, a way to build cool stuff, but not a business. Yahoo was a savvy company that said it would make web 2 a priority. 

As I recall, that's when web 2 started becoming mainstream tech. Early web 2 founders transitioned successfully. Other entrepreneurs built on the early enthusiasts' work. Competition shifted from ideation to execution. You had to decide if you wanted to be an idealistic indie bar band or a pragmatic stadium band. 

Web 2 was booming in 2007 Facebook passed 10M users, Twitter grew and got VC funding, and Google bought YouTube. The 2008 financial crisis tested entrepreneurs' resolve. Smart people predicted another great depression as tech funding dried up. 

Many people struggled during the recession. 2008-2011 was a golden age for startups. By 2009, talented founders were flooding Apple's iPhone app store. Mobile apps were booming. Uber, Venmo, Snap, and Instagram were all founded between 2009 and 2011. Social media (which had replaced web 2), cloud computing (which enabled apps to scale server side), and smartphones converged. Even if social, cloud, and mobile improve linearly, the combination could improve exponentially. 

This chart shows how I view product and financial cycles. Product and financial cycles evolve separately. The Nasdaq index is a proxy for the financial sentiment. Financial sentiment wildly fluctuates. 

Next row shows iconic startup or product years. Bottom-row product cycles dictate timing. Product cycles are more predictable than financial cycles because they follow internal logic. In the incubation phase, enthusiasts build products for other enthusiasts on nights and weekends. When the right mix of technology, talent, and community knowledge arrives, products go mainstream. (I show the biggest tech cycles in the chart, but smaller ones happen, like web 2 in the 2000s and fintech and SaaS in the 2010s.) 

Tech has changed since the 2000s. Few tech giants dominate the internet, exerting economic and cultural influence. In the 2000s, web 2 was ignored or dismissed as trivial. Entrenched interests respond aggressively to new movements that could threaten them. Creative patterns from the 2000s continue today, driven by enthusiasts who see possibilities where others don't. Know where to look. Crypto and web 3 are where I'd start. 

Today's negative financial sentiment reminds me of 2008. If we face a prolonged downturn, we can learn from 2008 by preserving capital and focusing on the long term. Keep an eye on the product cycle. Smart people are interested in things with product potential. This becomes true. Toys become necessities. Hobbies become mainstream. Optimists build the future, not cynics.

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