Keep Your Expectations Small

When your skills evolve, so does your fear. Here’s what you can do 

Image: Eunice De Guzman/Unsplash

“Failure is the condiment that gives success its flavor,” Truman Capote’s saying goes. The inversion is equally true; even just a sample of sweet success provides failure with its bitterness. 

Three weeks ago, I decided to make a screencast, film it, and sell it for money. It was an idea my friends and I’ve had for years; some of us run ecommerce businesses, some of us run studios, but none of us have actually tried selling information products. Almost immediately I decided, the thoughts came into my head… 

What an Evolved Fear of Failure Sounds Like

Eight years ago, I got takeout sushi with my friends, went upstairs to the Xtreme Labs office, and worked from sunset till dark to write and launch an ebook. I didn’t have a worry in the world; I was with friends, and even if I launched to a beautiful, round, zero, I would just figure it out after that. Hell, I was supposed to fail. I was a student. When else was I going to experiment?

But this time, I heard myself harshly critiquing the idea from the start. All those things I didn’t know eight years ago — the joys of ignorance — stood up and spoke out.

“Your audience isn’t big enough.” 

“You haven’t validated this idea.” 

“There’s not enough time to promote.”

The truth is, these voices weren’t even wrong. They all had valid points. But they were also just sophisticated ways of saying the same thing:

“I’m scared. Don’t do it!”

In accumulating my own expertise, I realized that my own fear of failure had evolved as well; I could point out flaws and reasons why things wouldn’t work much easier than I could eight years ago. 

My fear knew all the right, logical, things to say to talk me out of this. And in many ways, it was what I’d say to a friend or client in my situation.

As I worked throughout the week, I realized that I had lost agility compared to eight years ago, when I was a beginner. I was a student, and I’d never tasted success; I’d gotten used to the taste of failure. At least I was doing something

But now, my career, client list, and body of work grew, and I developed what I call.. 

The Intermediate’s Fear of Failure

As we get better at what we do, we expect to fail at it less and less often. We lose our connection with failure. The more work experiences a person accumulates, the stronger their reputation, and the greater their own expectations for the things they work on. The more we learn, the more we earn, the more we feel like it’s normal

For example, in the few weeks I focused on this experiment, I know the amount of money I could have made, if I wanted to get a job. A month not making that money can feel like I lost it. It’s tempting to expect my hourly rate to be the quantity I need to get back from my projects to justify my earning. Opportunity cost forces me to realize I’m investing all the potential earnings into my own life and learning experiences. 

Outside comparisons play a part, too. But now, eight years after my student side project, things seem scarier. People take on corporate VP titles. (I didn’t realize Goldman Sachs had 12,000 VPs in 2012.) They’re flexing on LinkedIn. They’re making down payments.

The fear of failure kept me doing the things I know I was good at, and didn’t support me in exploring the things I could be great at. Plus, it wasn’t real; nothing bad would actually happen if this project didn’t make a single dollar. Rather than enable me to develop new skills, it was keeping me in a silo. I needed to break out.

It really took this project to really encourage me to apply what I knew. I’ve watched Gary Vaynerchuk yell at 30- and 40-year-olds, “You’re a kid!” I think it’s an admonishment to return back to the mindset of a student. Like Amazon, everyday is day one. 

Return to the Beginner’s Mindset

A beginner’s mindset has no expectations. It is, by default, loosened up. It doesn’t worry about how the work or experience will turn out. 

The beginner’s mindset is about being okay with zero. Zero Likes. Zero views. Zero sales. Zero expectations. It’s purely about the experience, and zero results. You are a student again; you are a beginner again. 

In conventional linear progression, beginners accumulate experience. Other people may see them becoming intermediates, and then experts. But with the beginner’s mindset, even the most veteran experts are humble. They know that there are so many things they don’t know; so they’re always open to exploring, or re-exploring, an old idea. 

A beginner’s mindset can’t be read about; it takes practice. This experience meant a lot to me; it wasn’t the same as reading a book about the beginner’s mindset, it was a lot better

Keep Your Expectations Small

Paul Graham once wrote about keeping your identity small. I think it’s important that as we start excelling at the things we do, that we not throw away our experimental and playful side to preserve our reputations and expectations. In short, make something just for the hell of it, and ship it. 

It might not help your legacy; Andre 3000’s meticulous body of work is an example of that. But it will keep you creative; in his podcast with Rick Rubin, Andre talks about the pains of his legacy and how he feels stifled by external expectations.


The solution is to do something new, even if you think it might suck. Adopt a beginner’s mindset to overcome your intermediate fear of failure. What you’re working on today will limit or expand the things you can work on in the future. Keep your expectations small, and build the skill sets you need to do the things you want to do.

If You’re Starting to Write, Here’s the #1 Thing to Focus On

When the writing process met the theory of constraints

Image: Damir Spanic/Unsplash

“Should I write at my own blog, or at Medium?”

Of course, the question is worth considering if you’re a new writer. But a more pressing question you need to focus on is:

“How do I write something I’m proud of?”

Writing is meant to be fun and stimulating. It turns out best when you enjoy the process. Not only do you write better, but you keep writing. So the best place to start writing is wherever you get the most enjoyment from. It doesn’t really matter where it is, especially when you’re just starting out. Here’s why:

When You Start, Your Constraint Is Your Writing

In The Goal, author Eliyahu M. Goldratt introduces the theory of constraints:

Improvements made anywhere beside the bottleneck are an illusion.

In case you’re scratching your head, I made a diagram to illustrate this idea. Lastly, let’s say each piece of writing starts off as an idea, and your goal is to move it downwards as quickly as possible to add value to it (and make money). The pink bars are the measure of capacity. The red bars are the actual flow of effort and value produced and extracted:

Let’s unpack what each of these mean, starting at the far left:

The inefficient writing process: This process involves a lot of writing and editing, but is bottlenecked first by its opportunities to publish. For example, maybe the writer using this process writes only for Fast Company or New York Times. They’ve developed a strong reputation which enables their promoting capabilities. But because they don’t sell their own products (e.g., books) or offer services (e.g., speaking), they’re not maximizing what they earn. Writers pursuing this method are not interested in monetizing. Instead, they choose to focus on the craft of writing

The suboptimized writing process: This is the process of the cautious new writer we talk about in the opening section. They’re often so fixated on the place they publish, they don’t consider developing the critical parts of the writing process (ideating, writing, and editing). This process shows them eventually becoming capable of promoting and building an audience, but the underdeveloped early phases limit the amount of value they create. I see that first question, “Should I write at my own blog, or at Medium?” as an attempt to optimize for:

  • Promoting (e.g., SEO, network effects, etc.)
  • Monetizing (e.g., Medium pays for writing, whereas WordPress doesn’t)
  • Building audience (e.g., You can speak directly to readers in a newsletter, but if you write at Medium their algorithm determines your distribution)

But really, this person is best suited by focusing on writing better. Once they widen those parts of their capabilities, they’ll be able to create a larger volume of, which enables them to produce and eventually extract a lot of value.

The optimized writing process: The third is an expert writer; one that’s able to earn most of what each piece is worth. They still aren’t making the maximum money on everything they publish, but they’re getting close. Maybe they haven’t gotten their back catalog organized, so they don’t circulate (i.e., syndicate and republish) their work as much as they’d like to. Or, maybe they have so many ideas and drafts, but they’re not able to edit fast enough to keep publishing going. A lot of professional authors fit into this mould.

The high impact writing process: This process creates the maximum amount of value with each article, and extracts every single dollar out of it. This person publishes amazing work, perfectly optimizes their SEO, has a group of core fans that promote their work, sets up sponsorships and affiliate links without messing up their own reputation, and regularly attracts a ton of new readers to their audience. They also have a back catalog they often excerpt or republish at other places. This is the perfect writing process. I know of only a few people who have come close to mastering this mythical process. (I’d love to hear suggestions.)

When You’re Starting, Focus on Ideating, Writing, and Editing 

Nobody starts off writing their first article at the “optimized writing process.” When you’re first starting off, you shouldn’t worry yourself about all of those factors anyway; the main constraint is how much you’re actually writing. It’s about ideating, writing, editing, and publishing your work. 

If you’re not ideating, writing, editing, and publishing regularly, then the rest doesn’t matter: 

  • Your distribution won’t matter because you won’t have any writing to distribute
  • Your payment won’t matter because your work is not worth paying for yet
  • Your audience won’t matter because you won’t have anything to send to them

At the beginning, focus on writing better, faster, and more. The “better” part is the most important (quality), but shouldn’t come at so great a sacrifice that the other two (speed and quantity) aren’t always slowly improving. Make acceptable, not perfect; and always make sure you keep publishing.

Of course, when you write regularly, and you’ve got an audience, you might need more time to polish each article up. You can then reset your speed and quantity metrics (e.g., instead of four times a week, just once a week). Juggling these three factors will balance you out. 

When to Focus on an Ideal Place to Publish

Let’s say you’re writing regularly, and notice that each of your articles are producing the results of an inefficient writing process. You’re starting to ideate, write, edit, and publish good writing that you’re proud of. But, you’re only monetizing a small part of it. 

This is the time to focus on where you’re building your home on the internet. By then, writing should no longer be too serious a constraint; you’ve developed your skills as a writer, your ideating, writing, and editing capabilities are there, and you’ve refined your skillset. 

You’ve also likely developed a body of work that’s starting to get readers, hopefully passively through search engine traffic or social media. In situations like that, migration can be painful (e.g., you might be kicking yourself for not setting it up at your own blog), but it’s important to remember… 

You could not be writing at all.

It’s a challenge I face, and I see others wrestling with too. Starting to write is easy; constantly figuring out something worth writing, and polishing it up, is hard. It needs to stay enjoyable if you’re going to succeed at it. It’s easy to give up from the discouragement, or from a sense of overwhelm. The enjoyment and intrinsic motivation can counterbalance this.

When you’re first writing, it’s important to dial back; it’s the same as learning to cook. Signing up for a meal kit delivery plan can be crucial to starting the habit of cooking and building capacity. Eventually, when you’ve gotten a grip on cooking, you’ll make your own meal plans and order your own groceries. But if you give up, then you lose a chance to build a rewarding habit (and to enjoy the results).

The Key is Focus

Naturally, in a lot of situations, you can improve more than one thing at any given moment. In theory you can become a better writer, find more places to publish, and promote better at the same time. 


But focus can be the difference that makes or breaks your efforts as a writer, especially for anyone starting this part-time. When you identify your focus, then you can also set more realistic and reasonable goals, level your expectations, and move forward with a plan. At the beginning, every extra drop of effort needs to be focused into making something you’re proud of. You can sort everything else out after.

Hard Decisions Become Easy When You Do This

4 Ways to Gain Clarity When Opportunity Knocks

Image: 傅甬 华/Unsplash

Last week, a friend had a job offer come up. It was a stable job opportunity in a chaotic time. It would be a step up in his field of work, it promised good money, and it could open up very interesting doors.

He also experienced high stress while interviewing for the opportunity, he wasn’t sure about this specific career, and he wasn’t desperate for the money. 

He wasn’t sure yet about what he should do.

He called me because I was in a similar situation just a year and a half ago. Long story short, I decided to take on a big work contract. I was lucky things unfolded the way they did, but I should have known how to make that decision more deliberately. 

We chatted for an hour or so. I talked about my experiences, and almost started wandering down the path of what I’d do in his case. Then, I smartened up. 

In my note-taking system, I started a thread about how to make difficult decisions. I ran to get it, and read the notes in it to my friend during the call.

A few days later, he texted me and said he knew what he needed to do, and that our call gave him a lot of clarity into his situation. 

I was happy. I wrote the thread for myself, and I knew it would be useful for him, but didn’t realize how clarifying it could be. 

Here’s what I’ve written down in my notes, and what I told him:

Define the Important Areas of Your Life

I really like Skillshare and Otis founder Mike Karnjanaprakorn’s post on setting goals. The short of it is, he defines the areas of his life that are important to him, and sets goals he wants to achieve. Each week, and quarter, he checks in on his own progress.

The key to this is not just in the goal-setting portion, but actually in quarterly and weekly reviews. Are you actually making progress on those goals? What are you doing that’s working and not working?

In my experience, setting the initial goals can take maybe even less than an hour. The best way to come up with the best answer you can in that moment, then think and improve it the next quarter. Goals and plans are guesses, and you can always improve them. This way, whenever you check on your goals, you have the best version of them.

These goals will determine what you want your life to look like, as well as how you evaluate your opportunities. If, for example, my friend was interested in mental health, he’d consider that the interviewing process created a stressful experience for him. He might consider whether or not it was indicative of how the job would be, and decide deliberately whether or not it was worth it to him.

Define Your Anti-Goals

Metalab and Tiny founder Andrew Wilkinson writes about the power of knowing what you don’t want to do. He figured out what he wanted his days to look like by calling out the things he didn’t like (e.g., long meetings, packed calendars, etc.).

Back to my friend — he could quickly list the worst parts of his days. Or, if he wasn’t sure, he could look back at the worst 5 days of the month (or year), and see what they had in common. 

For example, if he hates meetings as much as Andrew does, and the job clearly requires a lot of meetings with stakeholders, etc., then he’d know this opportunity might not be worth his time. On the other hand, if there were no meetings at all, then this opportunity could be interesting. 

Work Backwards from the Future

In 2013, Pixar set a goal to make their movies cheaper and faster. On average, each movie cost them 22,000-person weeks, and they wanted to bring that down to 18,500. In Creativity, Inc., Pixar co-founder Ed Catmull shares how he prompted his team for suggestions: 

“The year is 2017. Both of this year’s films were completed in well under 18,500 person-weeks. … What innovations helped these productions meet their budget goals? What are some specific things that we did differently?” 

It’s a simple prompt, but one that I really like. They forecast the setting four years later, and ask for suggestions on specific things done differently. Without a realistic way to get there, a vision remains little more than just that. It won’t become reality.

If my friend had defined his goals, he could use this to determine how to get there. He’d have an idea of whether this opportunity sets him up to achieve his goals, or takes him further away.

Assess the Current Situation

Ryan Holiday asks, what’s the absolute worst thing that could happen? What would you miss out on if you did it? 

The answers need to be clear here. If they’re not, go ask someone who has either done something similar, or knows someone who did. Ask them what happened with the decision and what the outcome was. Or, go read a book about it. 

And as Ryan advises, most people can’t see your goals and vision beyond their own experiences. Don’t outsource your decision-making to them and ask, “What would you do?” They’ll give you an answer for what they’ll do, which they might position as what they would do if they were you, but neither is the same answer as what you should do.

I emphasized this to my friend, calling myself out, cognizant I might’ve biased him towards one decision or another. (Of course I had an idea what I would do in that situation, but that doesn’t mean I knew what was best for him. There is a subtle, but very important, difference.)

Clarity Makes Hard Decisions Easy

If there’s a common thread in all of these exercises, it’s that they clarify your goals, desires, and enable you to put a plan together for yourself. Whenever an opportunity comes up, you at least have a destination you’re working towards. 

From there, it’s just a simple matter of figuring out whether the opportunity supports you to getting closer to it, whether you can finesse it into such a vehicle, or whether it’s a trap — a swamp that will keep you stuck, forcing you to chase something you didn’t want to in the first place.

The Power of the 10% Read

Remember, 10% Is Better than 0%

Image: Nicole Wolf/Unsplash

“I wish I knew about this 10 years ago!”

I exclaimed this after I started organizing my notes and writing with them. And I only did that because after I read parts of How to Take Smart Notes. The book had been on my shelf for years; I’d even moved a couple of times with it. Yet I only picked it up after I resolved to spend 20 minutes reading it; I couldn’t put it down until two hours later.

The main subject of the book is a man named Niklas Luhmann, who wrote 60 books and published a two-volume grand theory, The Society of Society, on time. He did all this, as you can probably guess, with the help of his note-taking system.

I don’t know what Niklas ate for breakfast, or how he solved specific note-taking problems (like adding a card between 1 and 1a), but I started my note-taking system right after reading just a portion of that book. I also completely see a better way of doing it; a system that can be both analog and digital, and how to make time to maintain it. If a contemporary disciple of Niklas Luhmann had a look at my slipbox, they’d probably:

  • Turn me into a meme and laugh themselves silly
  • Cringe so hard they give me access to their thousand-dollar courses so they never have to see it again
  • Make a note to add to their thread about the deteriorating nature of notes… 

Hell, maybe all three. (Some note takers have big personalities!) But without having been willing to read parts of the book, and apply a lesson imperfectly, I’d never have learned or experienced any of this. So I propose a method to reading now, moving forward:

The 10% Read

The 10% Read idea is useful to everyone, but probably most useful to people who aren’t already reading 25 pages per day, and want to get value out of books: 

Read 10% of a non-fiction book, and apply one lesson from it.

The point of the 10% Read is to give yourself permission to speed-read through a book. Get acquainted with its best ideas, through looking at the table of contents, the index, and just randomly flipping through it. Accept a superficial understanding of an idea, and acknowledge it’s just the start. 

Take action on what you learned. If you’ve read 10% of Deep Work, start blocking chunks of time in your calendar. If you read Radical Acceptance, pay attention to your self-talk. Put reminders of these applications and ideas in your phone notes, your wallpapers, and your journals.

The 10% Read is meant to lower the barrier of reading a book so aggressively that you can’t help but show up. Then, apply just one lesson to apply to your life in some way. 

Most of us are taught to read cover to cover, and you may think it’s not worth your time to read just part of a book. But the truth is, even just getting one of a book’s best ideas are better than leaving it on your shelf and getting none of them. (And more importantly, not every book is worth your time to read in full!)

Ideas are worthless to you as mere words on a page. They’re only useful after you understand and apply them somehow.

The Power of Taking Away Just One Idea

It’s so tempting to say, “If I’m not going to remember this whole book, I might as well not read it. Why bother?” 

Curtis Jackson writes in Hustle Harder, Hustle Smarter:

“After you finish this book, you might only take a few of the principles with you. Even just one. That’s fine. That was the case when I read Robert’s 48 Laws of Power. Ask me today what that book was about and all I can really tell you is, ‘As the student, never outshine the master.’

“There were forty-seven other laws in that book, but that’s the one that stayed lodged in my brain. And because it’s never left me, I’ve been able to apply it so many times over the years. I’ve literally made millions by remembering to follow that principle.”

Similarly, when Joss Whedon admits to never finishing the Getting Things Done book, he still says that he applies the principles constantly. He says, “‘Next actions’ is one of the most important things that you can say in any endeavor.” 

Both of these people took away one important thing from their books, applied it, and used the techniques to great success. 

Each Application can Change Your Life

Imagine if Curtis had decided not to read The 48 Laws of Power until he had a proper note-taking system in place. Or Joss decided because he couldn’t finish Getting Things Done, that it wasn’t worth reading. Sure, they might’ve succeeded nonetheless, but they each would be missing an incredibly valuable tool in their belts. (After all, Curtis directly attributes earning millions to his adherence of the principle.)

Oftentimes, you just need one opportunity to exploit, or an idea to connect two dots. The more dots you expose yourself to, the greater the connections you can make, and the more value you can get from a book. 

Don’t leave a book closed because you don’t have time to finish it. Open it, skim it, and get what you can out of it.

Of course, even in Curtis’s and Joss’s cases, you could say that they might be even more successful if they read or retained the whole book. That’s why it’s worth considering the next evolution after you’ve mastered and gotten value out of the 10% Read.

From 10%, to 100%

Without the 10% Read, How to Take Smart Notes would still be on my shelf, and I’d still be without a note-taking system. I wouldn’t have gotten any value out of it. But after my read, I know that there’s much more value that I can get out of it.

 The 10% Read is all about starting at 10%. It’s not about staying there. And it certainly isn’t conflating 10% with 100%. It’s very clear I haven’t grokked some of the important ideas and philosophies yet. As Philip Stanhope, the 4th Earl of Chesterfield, wrote, “Whatever is worth doing at all, is worth doing well.”.

Understanding and applying 10% of a book might not be as powerful as understanding and applying 100%. I’ve now learned that How to Take Smart Notes is worth my time; I’m applying it every day, and I know how to improve it. Reading 10% of the book and applying the note-taking system already improved my writing process drastically. I can’t wait to read, and apply, the rest of it.

Respond, Don’t Create

Creating Content that Shares Your Perspective and Personality

Image: Joe Calomeni/Pexels

For many of us writing online, finding something worth saying is half the battle. And yet, this problem runs counter to one strategy to making ourselves heard: speak loudly and frequently. VaynerMedia CEO Gary Vaynerchuk, a successful user of such a strategy, has talked about how he was releasing 40+ pieces of content per day, but he wanted to figure out ways to release 1,000 pieces of content per day. It increases his chances of winning the social media lottery. His mantra, “Document, don’t create,” has gained a lot of momentum in the marketing world.

The idea of documenting is really about adding a more concrete prompt for us to create. And yet, while documenting our lives is one way to do things, there’s another — equally powerful — way to create more high-quality content each day: responding.

To borrow an analogy from How to Read a Book; the act of writing is like throwing, and the act of reading is like catching. Reading is not merely watching the ball go by; it takes work to receive it and understand it. Responding, in this case, involves catching the ball (catching), and then returning the ball back to the writer (writing). It does not catching the ball, dropping it, and losing our tempers.

Responding enables you to use the scale and communities of the internet to your advantage. It’s a very simple technique: 

  1. Select a few good sources (ones that you, and your peers and heroes, would like)
  2. Pay attention to what’s taking place
  3. Read or watch the things that pique your curiosity or provoke a feeling
  4. Feel, relax, think, remember, research, and collect facts
  5. Write a response to what you’re noticing

This is particularly useful on days that you’re short of ideas and inspiration; you can scan through the headlines of your favorite publications and see what’s trending. Use them as mirrors to see yourself, and for coming up with ideas. 

It helps to put some time and space between looking through the headlines, and seeing what you can actually remember maybe an hour (or 24 hours) later. Those have stood the test of time and stand out in your memory for a reason. Plus, any initial emotional reaction is likely to have cooled off. 

The simplest way of doing this is to spend time with an actual article, post, question, video, or book, and then respond to it. For example:

  • Draft founder Nathan Kontny’s response to a Reddit question about PPC campaigns. It’s worth noting this post, with four upvotes, didn’t exactly go viral at Reddit. It doesn’t matter. Spend your time at the places that you and your peers or heroes like to hang out, and let things catch your attention.
  • Author and Baohaus founder Eddie Huang’s response to a New York Times’ review of Peter Luger Steak House. Eddie deconstructs the essay and calls out flaws, and he does it all in his signature voice. 
  • Research Alex Guzey’s response to reading “Why We Sleep.” Alex uses his perspective and knowledge as a researcher to reveal that the science may not be as concrete as the original author would have us believe.

The key here is to use your perspective to do this. But of course, as you’re noticing and observing, you may notice some larger movements. That also provides you with a chance to put a name to a thing, which each of the following examples do:

  • Developmental psychologist Uta Frith’s Fast Lane to Slow Science is a response to the rise of fast science and the replication crisis. Not only does Uta tie together the observations to point out the trend, she also calls out specific ways for scientists and institutions to slow down fast science; namely, restricting output, emphasizing teamwork, and putting a greater focus on quality and societal impact.
  • Author Steven Gambardella’s response to the self-help stoicism movement (which he calls “pop stoicism”). Steven noticed the tons of trending self-help stoicism articles out there, and boils down his response to two points. I’ll bet he has more, but these two were the most relevant and developed of them.
  • Stratechery founder Ben Thompson’s response to Google Shopping serves as the hook to highlighting what he calls the “anti-Amazon alliance.” Ben’s clearly been observing and thinking about this for a long time, and he notices the Google Shopping move to be an important development in a larger thread. He uses the news to talk about his thread.

It would be fair for you to say, actually, that this piece itself is a response. I’m calling out a technique that I’ve noticed, that I haven’t seen as much of a spotlight on. 

Of course, the response adds a potential promotional benefit to spread your ideas; if your work is thoughtful, adds context, and reveals some sort of truth that the original piece didn’t, it could continue the conversation in social media or in some other publications. The original author might see it and respond. If you’re writing at Medium, readers will see it after they’ve read the original article. (From a marketing perspective, it “newsjacks” the original story and adds your perspective to it.)

For me, it helps to think of each response like a “Letter to the editor.” Here are some of my responses:

Social media requires a strange mixture of quantity and quality. While I started this particular article off with quantity, I want to highlight that each of the examples here are really thoughtful; they’re “high quality.” There’s no point in making something that you’re not proud of, or that you don’t find useful. 

If you’re ever in doubt, figure out what qualifies as acceptable work for you to put out. Don’t try to make everything perfect. It’s not only how you win at social media, but also how you practice and progress at your craft.

How to Learn, and Earn, like Curtis “50 Cent” Jackson

6 simple lessons, for a complex world, that will change your life

Image: Alex Const/Flickr

You may know Curtis “50 Cent” Jackson for selling 30 million records, for his hit TV show Power, or his lollapalooza business successes (including owning Vitamin Water, which sold to Coca-Cola for $4.2 billion). 

What you may not know is Curtis Jackson writes books. At this point in my life, I’ve read hundreds of books; hell, I’ve even professionally reviewed them. Curtis Jackson is one of my favourite authors. Despite working with different co-writers (I’ve got a book he co-wrote with Kris Ex, and another with Robert Greene), Curtis consistently provides interesting stories, and his voice is an energetic mix of hope and practicality.

Even though Curtis’s Hustle Harder, Hustle Smarter was branded as a self-help book (a genre I generally steer clear of), I read it and got a lot out of it. Here are six insights on how to learn and earn like Curtis Jackson:

How to Learn like Curtis Jackson

“Money is the goal, but oftentimes in order to get it, you have to retrain your brain to value experience. Especially if you weren’t born with a silver spoon in your mouth,” writes Curtis. He continues to soak up new ideas all the time, turning seemingly hopeless experiences into opportunities in the process. Here are a few ways Curtis learns:

Turn an obstacle into an internship: Before he famously signed with Eminem and Interscope Records, he was signed to Columbia, and they were stalling his album release. He assessed his situation, and noticed, “The way I saw it, Columbia might have been stalling, but I was still signed to them. I still had access to their office. I was going to make the most of that access.” Curtis took the subway every day, from South Jamaica to the Sony Building in Midtown Manhattan. When he got there, he would visit every team — street radio promotion, publicity, and graphic design — to watch them work on other people’s albums, and ask questions about their thought processes. The executives had no problem with it; they simply hoped he wouldn’t ask them about his album.

Understand the cause and effect: As he spent time with Columbia, he came to the insight: “… the labels could build on momentum, but they were limited when it came to creating it.” In order to get Columbia to put resources behind his album, he’d need to create his own energy and buzz. He applied this insight to make, “How to Rob.” The tactic worked, and 50 built buzz. (Unfortunately, after he was shot nine times, Columbia saw him as too great a risk and dropped him.)

Apply your insights to difficult circumstances, and exploit it: In The 50th Law, which Curtis Jackson co-wrote with Robert Greene, they described how labels lavished artists with money and perks, but created a feeling of dependence similar to highly paid employees. Labels usually decided how to position the artists, and directed key decisions on creative and publicity. They enticed artists into relying on the labels’ processes, making artists feel “helpless in the face of a viciously competitive business.” In this arrangement, most artists essentially exchanged their freedom for the label’s money. After his experiences with Columbia, after his successful debut at his second label, Interscope, Curtis wouldn’t let this happen. He put up his own money to shoot his own music videos, saving the label time and resources, but also regaining control over his creative and image. He also started his own G-Unit Records imprint with Interscope, using it to teach himself every aspect of music production and to run things on his own. Curtis manoeuvred his way into retaining control and freedom, while making the most of his label’s support. Even though the working arrangement wouldn’t last forever, Curtis could walk away with his own insights, processes, and team to continue moving forward as a successful independent artist.

It’s important to note that even after Curtis became a successful artist, he still seized every opportunity — no matter how difficult — to learn. As Curtis writes later in the book, “Your time is never wasted when you’re gathering information. This is why I’ll always prioritize information over a check.” 

How to Earn like Curtis Jackson

The saying goes, “You don’t get what you deserve. You get what you negotiate.” Negotiating is an art that directly affects how much you earn. Having seen his fair share of deals, Curtis shares a few principles on deal-making in Hustle Harder, Hustle Smarter:

Negotiations are not a reflection of yourself: Curtis writes, “I don’t care if you’re dealing with a longtime business partner, a friend, or a family member: the other person is never going to start at a number you think is fair. It’s just not how the process works.” Whenever you, or the other party, take a negotiation or deal personally, then the negotiation starts taking its toll on the relationship. Make sure you don’t let that happen. If you sense the other person’s guard come up, back off, reassure them, and offer to meet them in the middle.

Keep the equity in your relationships: When Curtis’s former collaborator Sha Money XL sent him an unexpected, and overinflated, bill for $50,000, Curtis countered with an offer for $30,000, and 1% of the profit on Get Rich or Die Tryin’. Sha didn’t budge from the original deal (despite even his own lawyer’s protests), and Curtis gave Sha his original request for $50,000. Unfortunately, the 1% of the album’s profits would’ve made Sha $1 million. Worse yet, it cost Sha his working relationship with Curtis. Curtis writes, “Our relationship was never the same. In just a few months I’d gone from seeing Sha as a partner I was prepared to share millions with to just another contractor.”

Start a deal to build leverage: Deals don’t just pop up magically; they require a body of work, relationships, case studies, and other forms of leverage. When Curtis took a deal with Starz that was way under his market value, he did it because he knew he didn’t have much leverage yet. His strategy with Starz was to create the biggest opportunity possible. His first deal started at $17,000 per episode for the first season of Power, which was less than he’d make spending a few minutes making an appearance at a nightclub. But Power became a hit, putting him in a position to re-sign with Starz for $150 million. Even if Power wasn’t the runaway success it is, at the very least Curtis would have been able to add to his body of work, learn from Starz, and build more leverage for his future productions.

How to Grow like Curtis Jackson

In the 2010s, Curtis Jackson had a decision to make. His incredibly successful music career as 50 Cent was turning, and he felt the crowds were no longer responding to his music the way they used to. He also observed that the entire music industry was changing drastically. When Interscope co-founder Jimmy Iovine started focusing on selling Beats headphones instead of selling records, Curtis realized it was time for him to make a change, too. He experimented with many ventures, tying them in with his social media (#smsaudio #effenvodka) for promotion. He also doubled down on his efforts with film, continuing his acting career and starting his TV show with Starz, which debuted in 2014.

Curtis writes about the attitude we all need to develop in response to setbacks; instead of dwelling on them, the self-talk could be, “I’ll get it back on the next one.” He talks about an insight he came to early in his business career, which is that there’s no “happily ever after” in business. And as in life, new problems always come up. The key is to adapt, be fearless, and keep moving forward. It’s a practical worldview, one that’s rooted in a blend of hope and practicality that has become Curtis’s signature in Hustle Harder, Hustle Smarter, and the rest of his books.

The Creative Failure that Led to Sigmund Freud’s Success

Why Even a Dead Page can have Purpose

Image: Sigmund Freud Collection, Library of Congress/Aggregate

In 1895, Sigmund Freud started Project for a Scientific Psychology, a monograph where he tried to explain all neuroses under a single framework. The ambition and expectation of the task brought trouble of equal magnitude. In Creating Minds, Howard Gardner writes that Freud “reveals his own despair at the magnitude of the task, the meager tools at his disposal, and the seemingly contradictory mission of laying bare what the psychic censors have withheld from introspection or consciousness.”

And yet, as Gardner highlights, Freud’s breakthrough work The Interpretation of Dreams can be seen as the successor to Project for a Scientific Psychology. The editorial note in Project for a Scientific Psychology agrees, “The immediate continuation of the ‘Project’ among Freud’s published writings is to be found in The Interpretation of Dreams.”

It was only after Freud finished Project for a Scientific Psychology, that he felt the doubts of it, “I no longer understand the state of mind in which I concocted the psychology,” he writes in a letter. He didn’t end up publishing Project, and it wouldn’t see the light of day until a decade after he passed away.

New creative work can always be built at the tail end of a creative failure. In Freud’s case, The Interpretation of Dreams wasn’t an immediate success either; only years after publishing did it cement itself as something that would change the fields of social science and establish the domain of psychology.

There are lots of reasons for us to do things that won’t work out well, especially because there’s a possibility that they lead to something that will. It’s possible, of course, that Freud could have come up with Interpretation without Project. But in practice, and in actuality, he made a monograph he couldn’t bring himself to publish, before he made the one that would cement his legacy. 

Writers sit on both sides of this, and I’m sure people in creative work of all sorts do as well. Mark Manson doesn’t force his writing when he knows it’s not good; why waste the time re-writing? But Danielle Steele advocates writing dead pages, knowing she’ll have something to work with after and that re-writing is easier than getting blocked.

Not every piece of work is meant to see the light of day; but maybe that wasn’t its purpose. The decision is yours to make.

As Stupid As This Sounds

Eddie Huang and David Chang dropped a podcast yesterday, and it was as good as I thought it would be. David’s voice kinda sounds like Joe Rogan’s, so it was almost like Eddie was back talking about TED and stuff.

There’s a moment in the first year of Eddie’s restaurant Baohaus, when Eddie personally delivered baos, and he recalls delivering to David in a tenement building on Grand street. David was already a prominent chef, and Eddie couldn’t believe David lived there.

“Nobody gets into this business to truly make money,” David says. “As stupid as that sounds.”

“No man, you do [it because] you love it,” says Eddie. “It’s also most of us that ended up in the restaurant business, it wasn’t our first choice…. I grew up in a restaurant, I saw how hard my dad worked, and I saw how lucky he had to get to get the run he had and then how quickly the rug was pulled out from under him. He had, maybe like a seven year run, where he broke bread and the rest of it was just bleeding.”

Two successful artists, running two successful businesses, that may or may not make it through this pandemic. It reminds me of author Robert Caro, who could’ve made a really handsome living writing shorter, faster, good books. Instead, he chose to spend decades researching Robert Moses and Lyndon B. Johnson to make probably the best books in his time. He’s got the trophies to show for it too. He writes in his book, Working:

“It’s the research that takes the time—the research and whatever it is in myself that makes the research take so long, so very much longer than I had planned. Whatever it is that makes me do research the way I do, it’s not something I’m proud of, and it’s not something for which I can take the credit—or the blame.”

Despite being a man of many words, Robert can’t quite put his finger on it. Neither can I, but I’ve something similar. It’s certainly not for research, but for writing and business. I know a lot of market-driven entrepreneurs, who optimize purely for financial returns. “If it’s not ecommerce or SaaS, don’t talk to me.” Frankly, I honestly think that they have what Caro describes as well, and can’t optimize the other way around. They feel a need to chase the money.

But it’s got to be OK for that not to be the goal. We need more businesses, whose interests are tied more locally, to have thriving communities. More businesses that are genuinely mission-driven, and still see money just as oxygen. That’s not just geographic, but can count digitally too, where a lot of people congregate. We can’t let the unicorns and VCs hog entrepreneurship.

There almost has to be something greater, if not just for cognitive dissonance. The numbers don’t work otherwise. Eddie and David talk about how most restaurateurs make 10–12% profit margins, and how some chef-owners work 72 hour weeks to take home $60,000.

I’ve always thought, and still think, there’s a way to balance it out; to make money, and to stay true to the vision. To compromise on inessentials. To hedge bets. Outside of Baohaus, Eddie writes books, did a TV show, and now directed a movie. Outside of Momofuku, David did the very great Lucky Peach, he’s getting that Netflix bread, the podcast, and I don’t know what else. They don’t have portfolios; they have bodies of work. If you don’t know… you won’t know.

The freedom to make these choices on how to spend your time, the currency of life, could bring anxiety and tension. But that’s the cost of choice. It’s never a bad decision to think twice about stupid, easy, money. Your bank account might be poorer for it, but your life could be richer.

Doing Something Interesting Is the Best Way to Promote Yourself

I’ve advised a lot of companies, leaders, and friends on how to promote their work through writing. But as I was thinking about it, combing through Eddie Huang’s The Pop Chef archives and having seen one too many aphorisms on Twitter, I thank God for granting me this moment of clarity:

If you’re not a writer, writing about your work is the best way to promote yourself.

If you’re a writer, doing interesting things is the best way to promote yourself.

When the product you’re promoting is your own writing, the solution isn’t to write more. It’s to make your writing better. And the best, fastest, way to do that is to write about something interesting that you did. And one way to do THAT, is to ingest a ton of interesting stuff and refine your perspective.

I say that about writing, but it applies to who makes outside or full-time income in the “content creation” business.

That being said, it’s hard to doing interesting things during COVID-19. It’s not like I can get my George Plimpton on and go immersive, that’s never been my cup of tea anyway. Staying sane counts; it’s not interesting, but it is healthy. Pusha T told me, wealth don’t buy health. (Yeah!). For me, and every other writer out there, the job is to:

  • Read and share interesting, obscure, books
  • Listen to or launch interesting conversations
  • Explore interesting things on the internet

And to keep at it, everyday. It’s painful to try to come up with some new mind-blowing concept every day, but some of the keys:

Respond. Go read the best magazines in the world, that few people are reading, and pick the articles that resonate most with you and who you are. If you’re on a mission, signal boost things. Talk about why something is smart/stupid, somebody is right/wrong, and why you believe/don’t believe in something.

Remix. If you’re not writing about COVID-19 right now, then you’re doing something right, but you better be damn sure it’s a good story. Everybody’s trying to stay alive and sane, and boring stories have a harder time of surviving. Meme it up if you have to.

Document. Every time I get an idea, it gives me a burst of anxiety. I wish I was kidding, but I feel an impulse to write everything down. Before bed, before the shower, after the shower, during a HIIT workout video, whatever. I’ll remix Bezos, these are the acorns that will grow into a tree of a good idea.

Have fun. Fun is usually interesting, but it’s got to be original. I played the Super Nintendo pack on Switch this weekend, but is it worth a blog post? [Chris Tucker voice] Hell, no! Shouts to Pharrell, the Mr. Magoo of music.

Ghostwrite. If you don’t know how to say something in an interesting way, remember how your favourite writers write. I don’t go so far as to type the words out myself, but I know some people do just to feel what greatness feels like. Reading is enough for me.

Write in serials. Don’t be working on some masterpiece with no due date. If you are, make a version of it that you can ship today. (This article is an example of that.)

The Rise of Personal Infrastructure

The company person is dead; long live the entrepreneur. There are plenty of people who have written extensively about reasons this change is happening; the gig economy, neoliberalism, the winner-take-all system being just a few of many factors. I’ll leave it to the experts to talk about macroscopic changes. 

One very clear factor is, each individual will need greater support. This support can show up in many forms, including friends and family, but I think one thing each person is in control of can make a drastic impact: personal infrastructure. Examples of personal infrastructure:

  • A note-taking system to support your thinking, capture your experiences, and enable you to mine mental gold.
  • Relationships. This might include mastermind communities (e.g., Slack groups, email threads, webinars) where people learn from each other. Or just expanding your network, with requests for introductions. Managing these relationships with personal CRMs like Superphone and Clay. (This is what entrepreneur and recording artist Ryan Leslie means when he talks about making 30 phone calls per day.)
  • Equipment including hardware like 3D printers, or software like Norbert. This requires learning new tools and a basic understanding of UX/UI, as well as keeping up with the tools that come out and free alternatives.
  • Your own automations and apps, which can be built with code, or with no code (like Zapier, IFTTT). I call these small machines. The greater your understanding of building products, the stronger and more useful these small machines can be.

Your personal infrastructure should be as free as possible; that is to say, you should be able to control it and make most of the rules, and you should minimize its costs. That way, there’s no reason it can’t stay with you regardless of your income and very basic mobile phone or laptop. (3D printers can be portable.)

Most of us spend our time in our work; we’re laboring and toiling away to get our tasks done, either for ourselves, for our clients, or for our employers. But every hour we spend in our personal infrastructure will enable us to do things more efficiently or effectively; if we write, then our infrastructure enables us to put ideas together faster. If we need support, we can reach out to people. If we need to print an iPhone dongle, we can use a 3D printer. 

With each hour we spend working on our work — working on our personal infrastructure, we’re potentially saving dozens, hundreds, or thousands of hours on future labor. 

Ideally, some of this time and energy we rescue from our personal infrastructures — as well as the solutions we devise — can be re-allocated to producing value for other people, supporting them with their own personal infrastructures. Sometimes, this will be an exchange of value; for example, maybe people will pay you money for your product, or for your perspective on something. 

Rescuing time and energy means regaining control of it, and freedom. That’s ultimately the purpose of personal infrastructure, to expand your capabilities so that you are free to pursue your greater calling (obviously within the boundaries of the law, in case you had to ask).