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.

Don’t give a number

Google pays its software engineers generously. While many of their employees are competent, they disregard a critical skill to maximize their pay.

Negotiation.

If Google employees have never negotiated, they're as helpless as anyone else.

In this piece, I'll reveal a compensation negotiation tip that will set you apart.

The Fallacy of Negotiating

How do you negotiate your salary? “Just give them a number twice the amount you really want”. - Someplace on the internet

Above is typical negotiation advice. If you ask for more than you want, the recruiter may meet you halfway.

It seems logical and great, but here's why you shouldn't follow that advice.

Haitian hostage rescue

In 1977, an official's aunt was kidnapped in Haiti. The kidnappers demanded $150,000 for the aunt's life. It seems reasonable until you realize why kidnappers want $150,000.

FBI detective and negotiator Chris Voss researched why they demanded so much.

“So they could party through the weekend”

When he realized their ransom was for partying, he offered $4,751 and a CD stereo. Criminals freed the aunt.

These thieves gave 31.57x their estimated amount and got a fraction. You shouldn't trust these thieves to negotiate your compensation.

What happened?

Negotiating your offer and Haiti

This narrative teaches you how to negotiate with a large number.

You can and will be talked down.

If a recruiter asks your wage expectation and you offer double, be ready to explain why.

If you can't justify your request, you may be offered less. The recruiter will notice and talk you down.

Reasonably,

• a tiny bit more than the present amount you earn

• a small premium over an alternative offer

• a little less than the role's allotted amount

Real-World Illustration

Recruiter: What’s your expected salary? Candidate: (I know the role is usually $100,000) $200,000 Recruiter: How much are you compensated in your current role? Candidate: $90,000 Recruiter: We’d be excited to offer you $95,000 for your experiences for the role.

So Why Do They Even Ask?

Recruiters ask for a number to negotiate a lower one. Asking yourself limits you.

You'll rarely get more than you asked for, and your request can be lowered.

The takeaway from all of this is to never give an expected compensation.

Tell them you haven't thought about it when you applied.

Calmness is a vital life skill.

It aids communication. It boosts creativity and performance.

I've studied calm people's habits for years. Commonalities:

Have mastered the art of self-humor.

Protectors take their job seriously, draining the room's energy.

They are fixated on positive pursuits like making cool things, building a strong physique, and having fun with others rather than on depressing influences like the news and gossip.

Every day, spend at least 20 minutes moving, whether it's walking, yoga, or lifting weights.

Discover ways to take pleasure in life's challenges.

Since perspective is malleable, they change their view.

Set your own needs first.

Stressed people neglect themselves and wonder why they struggle.

Prioritize self-care.

Don't ruin your life to please others.

Make something.

Calm people create more than react.

They love creating beautiful things—paintings, children, relationships, and projects.

Don’t hold their breath.

If you're stressed or angry, you may be surprised how much time you spend holding your breath and tightening your belly.

Release, breathe, and relax to find calm.

Stopped rushing.

Rushing is disadvantageous.

Calm people handle life better.

Are aware of their own dietary requirements.

They avoid junk food and eat foods that keep them healthy, happy, and calm.

Don’t take anything personally.

Stressed people control everything.

Self-conscious.

Calm people put others and their work first.

Keep their surroundings neat.

Maintaining an uplifting and clutter-free environment daily calms the mind.

Minimise negative people.

Calm people are ruthless with their boundaries and avoid negative and drama-prone people.

We love round numbers, don't we? $100,000 is a frequent freelancing milestone. You feel like six figures means you're doing something properly.

You've most likely already conquered initial freelancing challenges like finding clients, setting fair pricing, coping with criticism, getting through dry spells, managing funds, etc.

You think I must be doing well. Last month, my freelance income topped $100,000.

That may not sound impressive considering I've been freelancing for 2.75 years, but I made 30% of that in the previous four months, which is crazy.

Here are the things I wish I'd known during the early days of self-employment that would have helped me hit $100,000 faster.

1. The Volatility of Freelancing Will Stabilize.

Freelancing is risky. No surprise.

Here's an example.

October 2020 was my best month, earning $7,150. Between $4,004 in September and $1,730 in November. Unsteady.

Freelancing is regrettably like that. Moving clients. Content requirements change. Allocating so much time to personal pursuits wasn't smart, but yet.

Stabilizing income takes time. Consider my rolling three-month average income since I started freelancing. My three-month average monthly income. In February, this metric topped $5,000. Now, it's in the mid-$7,000s, but it took a while to get there.

Finding freelance gigs that provide high pay, high volume, and recurring revenue is difficult. But it's not impossible.

TLDR: Don't expect a steady income increase at first. Be patient.

2. You Have More Value Than You Realize.

Writing is difficult. Assembling words, communicating a message, and provoking action are a puzzle.

People are willing to pay you for it because they can't do what you do or don't have enough time.

Keeping that in mind can have huge commercial repercussions.

When talking to clients, don't tiptoe. You can ignore ridiculous deadlines. You don't have to take unmanageable work.

You solve an issue, so make sure you get rightly paid.

TLDR: Frame services as problem-solutions. This will let you charge more and set boundaries.

3. Increase Your Prices.

I studied hard before freelancing. I read articles and watched videos about writing businesses.

I didn't want to work for pennies. Despite this clarity, I had no real strategy to raise my rates.

I then luckily stumbled into higher-paying work. We discussed fees and hours with a friend who launched a consulting business. It's subjective and speculative because value isn't standardized. One company may laugh at your charges. If your solution helps them create a solid ROI, another client may pay $200 per hour.

When he told me he charged his first client $125 per hour, I thought, Why not?

A new-ish client wanted to discuss a huge forthcoming project, so I raised my rates. They knew my worth, so they didn't blink when I handed them my new number.

TLDR: Increase rates periodically (e.g., every 6 or 12 months). Writing skill develops with practice. You'll gain value over time.

4. Remember Your Limits.

If you can squeeze additional time into a day, let me know. I can't manipulate time yet.

We all have time and economic limits. You could theoretically keep boosting rates, but your prospect pool diminishes. Outsourcing and establishing extra revenue sources might boost monthly revenues.

I've devoted a lot of time to side projects (hopefully extra cash sources), but I've only just started outsourcing. I wish I'd tried this earlier.

If you can discover good freelancers, you can grow your firm without sacrificing time.

TLDR: Expand your writing network immediately. You'll meet freelancers who understand your daily grind and locate reference sources.

5. Every Action You Take Involves an Investment. Be Certain to Select Correctly.

Investing in stocks or crypto requires paying money, right?

In business, time is your currency (and maybe money too). Your daily habits define your future. If you spend time collecting software customers and compiling content in the space, you'll end up with both. So be sure.

I only spend around 50% of my time on client work, therefore it's taken me nearly three years to earn $100,000. I spend the remainder of my time on personal projects including a freelance book, an investment newsletter, and this blog.

Why? I don't want to rely on client work forever. So, I'm working on projects that could pay off later and help me live a more fulfilling life.

TLDR: Consider the long-term impact of your time commitments, and don't overextend. You can only make so many "investments" in a given time.

6. LinkedIn Is an Endless Mine of Gold. Use It.

Why didn't I use LinkedIn earlier?

I designed a LinkedIn inbound lead strategy that generates 12 leads a month and a few high-quality offers. As a result, I've turned down good gigs. Wish I'd begun earlier.

If you want to create a freelance business, prioritize LinkedIn. Too many freelancers ignore this site, missing out on high-paying clients. Build your profile, post often, and interact.

TLDR: Study LinkedIn's top creators. Once you understand their audiences, start posting and participating daily.

For 99% of People, Freelancing is Not a Get-Rich-Quick Scheme.

Here's a list of things I wish I'd known when I started freelancing.

1. Although it is erratic, freelancing eventually becomes stable.

2. You deserve respect and discretion over how you conduct business because you have solved an issue.

3. Increase your charges rather than undervaluing yourself. If necessary, add a reminder to your calendar. Your worth grows with time.

4. In order to grow your firm, outsource jobs. After that, you can work on the things that are most important to you.

5. Take into account how your present time commitments may affect the future. It will assist in putting things into perspective and determining whether what you are doing is indeed worthwhile.

6. Participate on LinkedIn. You'll get better jobs as a result.

If I could give my old self (and other freelancers) one bit of advice, it's this:

Despite appearances, you're making progress.

Each job. Tweets. Newsletters. Progress. It's simpler to see retroactively than in the moment.

Consistent, intentional work pays off. No good comes from doing nothing. You must set goals, divide them into time-based targets, and then optimize your calendar.

Then you'll understand you're doing well.

Want to learn more? I’ll teach you.

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.