Ship 30 for 30

Co-captain of Ship 30 for 30 – a cohort-based course that has helped over 3,000 students start writing online by writing every day for 30 days.

Co-Captain of Ship 30 for 30

Premium Ghostwriting Academy

Premium Ghostwriting Academy (PGA) trains freelance writers & ghostwriters on how to become Premium Ghostwriters, land high-ticket ghostwriting clients, start earning $10k per month selling packaged services (like Educational Email Courses), and ultimately build a ghostwriting agency and scale their earnings to $100,000 per month.

Co-Founder

Write With AI

The leading paid newsletter on how to turn ChatGPT and other AI platforms into your own personal Digital Writing Assistant.

Typeshare

Typeshare.co is the leading platform for Digital Writing templates & AI tools

BlackRock

Portfolio Manager for the $2.1 billion Obsidian Fund

Portfolio Manager

I talk about digital writing & personal progress

Here's a quick rundown of how I've spent my last 5 years:

1. Studied math and played football at Princeton. I graduated in 2018 with a degree in financial engineering and played center for the Tigers. In college, I was a 280-pound offensive lineman, so for the last 5 years, I've had to completely rewrite my personal operating system on the health & fitness front. I currently weigh 185 pounds and have learned a lot along the way!

2. Graduated and immediately started working for BlackRock in New York City. I worked as a junior hedge fund trader for 4 years, focusing on global macro markets. This was my dream job and the only corporate job I've ever had. In fact, it's the only job *interview* I've ever had (since I interned there as a junior in college).

3. Realized working for someone else was not going to be the long-term path for me. 12 months into working on Wall Street, I saw someone in their mid-40s ask their boss for permission to go to their son's Little League game. At that moment I realized I wasn't cut out to take directions or instructions from other people for very long.

4. Started to write on my old blog, then on Twitter. Rather than quit immediately, I started to passively explore other opportunities by writing online, starting out on my old blog (which no one knew existed), then transitioning to Twitter in July of 2020.

5. Changed my trajectory with a 30-day writing challenge, which led me to start Ship 30 for 30. In September 2020 I was ready to give up writing entirely. But I gave it one more shot, this time moving from a weekly blog post to a daily Twitter thread. The challenge was a huge success. It took me 9 months to reach 100 followers and 1 month to go from 100 to 2,000. And that personal writing challenge turned into the foundation of Ship 30 for 30, which started as nothing but a Slack accountability group to help people publish consistently.

6. Scaled Ship 30 while working remotely for all of 2021. I built and scaled Ship 30 with Nicolas Cole to over 2,000 students in 2021—all while continuing to work full-time (remotely) for BlackRock. But towards the end of 2021, Ship 30 hit an inflection point and it no longer made financial sense for me to continue working on Wall Street.

7. Left BlackRock in March of 2022 to write and build on my own. After weeks of weighing the pros and cons and trying to project my path forward, I made the decision to leave BlackRock and chart my own path. 15 months into making that decision and I'm confident it's the best one I've ever made.15

Here are Pixar's 22 Rules For Storytelling (a must-read for writers, entrepreneurs, and anyone who wants to tell captivating stories):

Dickie Bush 🚢

22 Rules For Storytelling From Pixar

In 1982, the legendary marketer David Ogilvy sent a memo to his staff titled "How To Write."

Here's a breakdown of the memo (a masterclass in effective writing):

The memo starts with a clear why.

"The better you write, the higher you will go in Ogilvy & Mather. People who think well, write well. Good writing is not a natural gift. You have to learn to write well."

Replace "Ogilvy & Mather" with any company and this holds true.

1/ Read the Roman-Raphelson book on writing. Read it 3 times.

Every company on Earth would be a better place if this book was required reading.

If you are still sending emails with Walls of Text, order this.

2/ Write the way you talk. Naturally.

"Finding your writing voice" is a waste of time.

You already have your voice—the one you use every day.

Here's ow to start using it in your writing:

• Choose a topic

• Record yourself talking about it

Then, transcribe it and start there.

3/ Use short words, short sentences, and short paragraphs.

This one takes practice.

So read everything aloud before you publish it.

When you find yourself getting caught up, it's a sign you need to simplify.

4/ Never use jargon words like "reconceptualizes, demassification, attitudinally, judgementally."

When you see someone using jargon, they're hiding their lack of understanding.

An easy solution: pretend you are writing to an 8th grader.

5/ Never write more than two pages on any subject.

99% of books should be blog posts.

And 99% of blog posts should be tweets.

I would preface this by saying: never *publish* more than two pages on any subject.

If it can't fit in two pages, it should be simpler.

6/ Check your quotations.

This one is simple enough. Misquotes are unforced errors.

7/ Never send a letter or memo on the day you write it. Read it aloud the next morning, then edit it.

This is the number one piece of writing advice I give people.

If you are publishing something important, always, always, give it room to breathe.

And always read it aloud.

8/ If it is something important, get a colleague to improve it.

This pairs nicely with point number 7. If it's something really important, write it, give it a day, edit it, then send it to a colleague.

9/ Before you send your letter or memo, make sure it is crystal clear what you want the recipient to do.

Put yourself in the reader's shoes and identify exactly the next step they should take after reading.

Then, articulate those steps for them.

10/ If you want ACTION, don't write. Go tell the guy what you want.

Last and most importantly, writing is never a replacement for a targeted conversation.

Most messages should be conversations, especially ones that require action.

Boom that's it!
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📌 Want to start writing online?

Here's a free 13,000-word Ultimate Guide with everything you need to get started:

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5 small habits that accelerated my career:

(These helped me escape my 9 to 5 to build a 7-figure digital writing business)

1. Remembering the name of every person I met.

I used to think I was horrible with names—but I was just being lazy.

So I started writing down the name of every person I met in a simple note on my phone. First impressions are powerful, but the follow-up impression of remembering someone’s name (especially when they don’t expect you to) is even more powerful.

2. Taking and publishing notes on all content I consumed.

I spent years reading books and listening to podcasts without taking notes.

This felt productive, but it was actually a waste. Once I started taking notes, distilling what I learned, and sharing those ideas with others, my personal growth accelerated.

3. Working for 3 hours every morning on 1 task, outlined the night before.

At this point it’s cliché, but you can change your life in 6 months with just 3 hours of deliberate, focused effort every single morning. And it took me years to realize this—but now, it’s the only sacred work block I focus on completing each day.

4. Putting my phone on airplane mode for the first 4 hours of the day.

The only reliable hack I've found for completing those focused morning work blocks is to ruthlessly eliminate distractions. And that means keeping my phone away from me.

5. Keeping a list of high-quality questions to ask my mentors.

Lastly, the only "shortcut" in life is avoiding mistakes and learning from people ahead of you.

And so over time, I collected good questions that helped me learn tactical lessons from the people that I looked up to, rather than just asking to "pick their brain."

That's it!

These tiny habits are simple but powerful.

If you enjoyed this, then follow me Dickie Bush 🚢 for more posts on building digital businesses and personal progress.

Then leave me a comment—which habit will you be starting with?

The most powerful reflection you can do:

The Monthly Review.

Most people go their *entire* life without reflecting.

And before they know it, years have gone by and it's too late to change.

So don't let this happen—grab a pen, crack open a notebook, and answer these 5 questions:

The goal of The Monthly Review:

Block 60 minutes to slowly process the month.

It's easy to get caught up in the day to day & lose sight of the bigger picture.

And after trying 1000+ reflection questions, I chose each question for a specific reason.

Let's start with the first:

1. What were my biggest wins & milestones?

These are things that you will look back on with pride & fond memories at the end of the year.

• Health wins
• Business wins
• New relationships
• Goals accomplished
• Fun memories & events

Recapping wins & milestones kicks the review off on a positive note.

So often, our focus is on the negative. But this questions helps us celebrate all the things going well! And it also creates a "ledger" of wins from the year.

From there, you ask a more important question:

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2. What were my biggest realizations?

I used to call this my "biggest losses."

But I reframed this—because something is either a win, or it teaches you about the world.

And by constantly collecting these realizations, you are always learning.

Most of my realizations are about my:

• Health
• Beliefs
• Business
• Lack of skills
• Relationships

By constantly iterating and distilling these lessons, you will level up month after month after month.

From here, you go from looking backward to looking at the present:

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3. What areas am I most satisfied? Least satisfied?

Split the page in 2 columns and brain dump bullet points of everything that comes to mind.

The goal here is to identify in the present moment what's working and what's not working.

From there, you ask another question:

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4. Based on these areas, what am I going to do more of? Less of?

This is the 80/20 rule in action.

20% of your:

• Habits
• Beliefs
• Friends
• Actions

Are leading to 80% of both your positive *and* negative results.

Now you should have 2 lists:

• Things to *double down* on that are bringing you the positive results
• Things to *stop doing entirely* that are bringing you the negative results

Put those lists somewhere you can see them every morning (for me, that's on my bathroom mirror).

Now, it's time to think about the future:

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5. What am I thinking about for the month ahead?

This is a quick list of things you're:

• Excited about
• Thinking about
• Uncertain about

This turns into a letter to your future self you can read at the end of the month.

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And just like that, the review is complete!

The beauty of this process is you can constantly capture these things throughout the month.

• Wins & milestones
• Realizations & decisions
• Things going well & things to improve

Then, at the end of the year, you collect these monthly reviews and distill the entire year.

$5,000 hit my PayPal account.

“This has to be a typo...” I thought to myself.

So I messaged him.

“Hey, did you mean to send $5,000?”

His response:

“Yeah, is that enough?”

And just like that, Ghostwriting completely changed my life trajectory.

Here’s the story:
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📌 Ghostwriting is how I made my first $5,000 online.

It helped me imagine a life beyond my 9 to 5—which ultimately led me to escape the Wall Street rat race.

To get started, here's a 5-day crash course:

https://lnkd.in/eWcBhjKu

How I Made My First $5,000 On The Internet

Why do most people make *zero* progress for years on end?

Because schools teach us to be “well-rounded”.

But successful people obsess over the *one* thing they do better than 99% of people and build their life around it.  

Here are 10 obsessions that have shaped my life so far:

1. The Tampa Bay Rays. The first sports team I ever fell in love with. At 5 years old, I spent hours memorizing the stats & names of every player (despite them being a horrendous team).

2. Pokemon Fire Red. The first hand-held video game I played, racking up days of gameplay to complete my Pokedex.

3. Yu-Gi-Oh. From Pokemon came Yu-Gi-Oh. I obsessed over the TV show and cherished the opening of trading card packs.

4. Runescape. From Yu-Gi-Oh came Runescape, which to this day taught me more about life & business than any other game.

5. Speedcubing. In 5th grade, after watching The Pursuit of Happiness, I became obsessed with the Rubik’s Cube, carrying it with me everywhere & participating in local tournaments.

6. Call of Duty 4. This was the apex of my video game career, playing on the professional Call of Duty 4 circuit in 7th grade.

7. Football. Luckily, my obsessions shifted from video games to sports in high school, which helped me earn a spot at Princeton where I played center for 4 years.

8. Computer Science. Despite loving football in college, my true obsession at this time was learning to code. I took every class I could & spent my nights & weekends building iOS apps.

9. Macroeconomics. Upon graduation, I worked as a hedge fund trader at BlackRock where I immersed myself in the world of bonds, currencies, macroeconomics, and monetary policy.

10. Digital Writing & Ghostwriting. I despised writing in college. But in the real world, I realized it’s the most potent skill you can have. Sharing your ideas, learning quickly, accelerating your personal growth, and finding new (& lucrative) opportunities—everything starts with writing.

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The single greatest thing my parents did for me was let me follow my obsessions wholeheartedly.

16 hours of Runescape every day for an entire summer? Yup, no questions asked.

Will be 100% how I raise my kids one day—fostering obsession as a character trait.

Why?

Because the real world rewards obsession.

Being a “jack of all trades” is great if you want a W2 job (and a slim chance of building wealth).

For years, I struggled with a gratitude practice.

"What am I grateful for?" 

Was always a tough question for me to answer.

Why?

Because gratitude is "relative."    

So I hacked my gratitude practice by asking these 3 dead-simple questions (and saw my gratitude skyrocket as a result):

1. What do I have today that my 10-year-old self would beg to have? 

Right away, I'm overwhelmed with answers. Think about how many cool things you're doing today that your younger self would dream to have. Those are things to be grateful for!

2. What do I have today that my 85-year-old self would beg to have? 

Same idea here, but in reverse. Think of all the things you have right now that you're going to lose over time. Write those down and start to cherish them.

3. What do I have today that my current self, when sick or injured, would beg to have? 

And lastly, every time I'm sick or injured, I regret not soaking in how good I felt in the past. So now, I'll sometimes pretend I'm in that state, which forces me to celebrate my health and wellbeing (which I so often take for granted).

Aaaand that's it!

If you struggle to stick with a gratitude practice, give these small reframes a try. They'll give you a new lens to use every day.

If you liked this, then follow me Dickie Bush 🚢 for more posts on personal progress. 

Then leave me a comment to let me know if this was useful ✊
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In it, I share no-fluff frameworks for making personal progress: dickiesdigest.com

Here's how to use James Clear's Four Laws of Behavior Change to build a daily writing habit you can stick to:
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📌 Want to start writing online?

Here's a free 13,000-word Ultimate Guide with everything you need to get started:

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4 Dead-Simple Steps To Build A Daily Writing Habit

The simple 3-step framework I use to break out of any "writing rut":

For the last 3 weeks, I’ve been blocked by:

• Overthinking
• Perfectionism
• Procrastination

To get writing again, I use the “One Take Timmy” method— here’s how it works:

Step 1: Pull up a different writing “notepad"

For me, I do all of my writing in Apple Notes. 

So I switch to something like:

• Discord
• iMessage
• WhatsApp

The goal here is to write in a different “environment” than the one that has me stuck.

Step 2: Pick one person who might find value in my idea

At any time, I have a backlog of 50+ ideas.

And I spend too much time trying to decide which one would be most valuable to the most number of people.

The result?

I end up writing none of them.

To prevent this, I pick an idea and then find one person who would find it useful.

• If it’s about writing, I find a writer in my contacts
• If it’s about business, I find someone who runs a similar business
• If it’s about personal growth, I find someone younger who looks up to me

The goal here is to write something directly to one target reader.

Step 3: Write “hey name,” then brain dump exactly what I want to say

I write the person’s name so it feels like I’m sending them a direct message.

Then, I brain dump everything that’s on my mind about the idea.

• No editing
• No overthinking
• No hitting backspace

And most of the time I write it on my phone.

Then I press send.

At worst, I have an in-depth outline I can sharpen up to publish the next day.

But oftentimes, I’ll just remove the “hey name” and publish it directly (which is what I’m doing right now!)

And just like that, I’ve broken out of my rut.

This method works for 3 reasons:

Reason 1: It completely takes the pressure off of writing “for an audience.”

Most people suffer from writer’s block because they’re worried about what a group of people might say.

So they overthink every word and spend weeks over-editing trying to make it “perfect.”

But when you’re writing for one person, especially a friend, that feeling melts away.

And since you picked someone who you know would find it valuable, your level of conviction to write it goes up.

Reason 2: It unlocks your natural writing voice.

The best content doesn’t look like content—it looks like a message in a group chat.

Simple words, easy to read, no fluff.

Which is why I use simple messaging apps to write that first draft.

I come off conversational which makes it easy to read.

Reason 3: It leads you to the next piece based on the person’s follow-up message.

Sending that messy brain dump to a target reader always leads to helpful responses.

• “Could you say more on this part?”
• “What about if I’m struggling with ABC?”
• “Could you show me an example of XYZ?”

Now, I’ve got a handful of content ideas to work on, sourced directly from a target reader.

And just like that, my writing flywheel starts to spin.

If you enjoyed this, be sure to follow me Dickie Bush 🚢 for more posts like this.

7 core beliefs I read every morning that shape the way I see the world:

Now, before I share the list, I use these beliefs to develop ONE core character trait:

OPTIMISM

This is:

• The way I want to feel
• The way I want people to describe me
• And the energy I want my readers to feel after consuming something I’ve written

Every belief is written in a way that forces me to be excited about the future & empowered to confront it.

With this in mind, I read my list first thing every morning.

Why?

Because my brain is an “evidence seeker.”

When I prime it with a belief, I will go out of my way to find evidence to reinforce it.

The problem?

This works against most people—myself included.

This was me at 22 years old:

• 280 pounds
• Tens of thousands in debt
• Drinking 40 beers a week

I’d then spend all day with a pessimistic attitude, playing victim, thinking the world was conspiring against me.

However, that all turned around when I started to overwrite my old beliefs with this new list:

1. Everything in this world is 100% rigged in your favor
2. Every circumstance is an opportunity for progress
3. Every outcome in your life is 100% your responsibility
4. Everything you want you must initiate yourself
5. Every person you come across has something to teach you
6. Everything is "learnable" if you can find the ideal scene
7. Every investment you make can have positive returns if you choose so

Slowly but surely, I went from a pessimist to an optimist.

From a reactive victim to a proactive world-builder.

And if you’re looking to do the same, I hope you find this list useful ✊
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In it, I share no-fluff frameworks for making personal progress: dickiesdigest.com

This dead-simple system will help you say 1 idea in 1,000 unique ways (so you never stare at a blank page again).

It's called the 4A Framework—here's how it works:
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📌 Want to start writing online?

Here's a free 13,000-word Ultimate Guide with everything you need to get started:

https://lnkd.in/eG9hqjJT

Say 1 Idea In 1,000 Different Ways (The 4A Framework)

Beginner writers have 2 choices:

1. Curate other experts
2. Say something ultra-specific

Why only 2?

Credibility.

If you've never published anything, readers will not trust you to give "general advice."

But by curating other experts, you aren't claiming to be "credible" at all.

You're borrowing credibility.

Let's say you write about productivity advice.

Most beginner writers would start with general productivity tips:

• Time Blocking
• The Eisenhower Matrix
• The Pomodoro Technique

But in the beginning, readers have *zero* reason to trust you.

So here's what to do instead: 

First, curate the productivity routines & frameworks of the world's most productive people. 

Look at the subtle difference in these two posts: 

• "How To Use The Eisenhower Matrix."
• "How These 10 Billionaires Use The Eisenhower Matrix."

If you have zero followers and this was your only post, no one would read the first one. 

But a lot of people would read the second one. 

And if you do the curation well, you get credibility points for distilling something better than anyone else.

That's how to build credibility through curation.

Now, let's build credibility through specificity.

Here are another two posts:

• "How To Use The Eisenhower Matrix."
• "How Middle-Market SaaS Product Managers Can Use The Eisenhower Matrix To Streamline Their Day."

Anyone can read the second headline and know whether it's for them or not. 

With the first headline, you're writing for everybody (which is writing for nobody).

But with the second headline, you're writing to one *specific* person (middle-market Saas PMs) to unlock a *specific* benefit (streamlining their day).

(Hint - you *are* a middle-market SaaS PM that has used the Eisenhower Matrix to streamline your day - that's why you're credible).

And so, for the 0.1% of people who are just like you, this will resonate with them.

With these two techniques, you're building a barbell of credibility and attracting:

• A general audience interested in productivity advice (you're their trusted curation source)
• A niche audience of SaaS PMs (who trust you because you're like them)

Now, over time, you can branch out. 

Since you're curating other experts, you're learning quickly.

So you can remix their frameworks to Name and Claim some of your own.

And with your niche audience, you can branch out into other topics they are interested in.

This is the *exact* path I took when I first started as a writer.

I knew nothing about writing, copywriting, or storytelling when I started. 

So what did I do? 

I followed this exact playbook for people who wanted to start writing but didn't know where to start (who were just like me).

And now, I've built an audience who sees me as a somewhat credible source. 

This means I can branch out and start to explore creating my own frameworks.

Boom! That's it.

For more writing tips, check out the 13,000-word Ultimate Guide To Start Writing Online—link at the top of this post.

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Journaling is the single most powerful habit for personal growth.

And over the past 5 years, I've journaled every single morning.

After testing 1,000 questions, I always return to these 5 prompts:
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5 Proven Journaling Prompts To Boost Personal Growth

10 problems that make you think you're a terrible writer (and how to fix them):
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📌 Want to start writing online?

Here's a free 13,000-word Ultimate Guide with everything you need to get started:

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Beat The 10 Problems Holding You Back As A Writer

Use this dead-simple 3-part framework to rapidly learn anything:
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The Simple 3-Part Framework To Rapidly Learn Anything

“Put those clippers down, I need 5 minutes.”

I popped out of the barber chair, grabbed my phone, and scrambled outside.

That’s when I saw my name sitting at the top of Tim Ferriss' newsletter sent to 3 million people.

And that shoutout completely changed my life trajectory:

How I Got A Shoutout From Tim Ferriss In 5-Bullet Friday

The 7 staples of my current ideal day (that I would have only dreamed of living when I was stuck in my full-time job 5 years ago):

1/ Up at 5 AM for 3 hours of focused work 

I crave the morning silence to get deep work done. 1 task, 3 hours, outlined the night before, every day like clockwork.

2/ Morning cardio without my phone 

After my morning work, I do some kind of movement/cardio (running, walking, or yoga) without my phone. This lets me finish processing the work I did earlier that morning.

3/ 4 hours of work with my team

After a high-quality breakfast, I strap in for some collaborative work with my team (meetings, calls, coaching, etc.). The highest leverage thing I can do is align my team on the right things.

4/ 2 hours of direct sunlight

Born and raised in Florida, I thrive on warmth, sunlight, and vitamin D. I make it a point to be outside for at least 2 hours in the sun daily.

5/ Heavy lift in the afternoon 

By the time 4 PM rolls around, I'm mentally cooked but physically fresh (and fueled). So I like to do my lifts in the afternoon to round out the day.

6/ High-quality fresh dinner

Post lift, I love to cook my own dinner with the dead-simple basics. Steak, potatoes, spinach, organic fruit, and spring water. Can't beat it.

7/ End-of-day mobility & reflection

Lastly, I end the day with a walk, some stretching, light reading, or audiobooks, and then complete my end-of-day check-in form before getting to bed around 9 PM, ready to do it all again.

Aaaand that's it!

Living my dream life right now, a life I couldn't even imagine 5 years ago. 

Will you add anything to your daily schedule? Let me know in the replies ✊

Want to start writing but can't overcome the blank page?

Use these 21 templates for the next 21 days (to make writing every day for the first 3 weeks of May effortless):

Before we start, a quick breakdown.

Everything you write falls into 4 buckets:

• Actionable (here's how)
• Analytical (here's what)
• Aspirational (yes, you can)
• Anthropological (here's why)

Every 1 of these 21 ideas falls into 1 of these buckets.

Let's dive in:

These are Actionable:

1. Share 1 underrated tip for solving a certain problem.

2. Share 1 framework that helps you get something done in less time or with less stress.

3. Share the 1 piece of advice to you would give to a beginner in your field.

4. Share 1 software tool that helps you the most (that most people know nothing about).

5. Share 1 helpful website (that you think is rarely used).

6. Share a step-by-step guide for accomplishing 1 specific task.

7. Share the 1 book that most helped you in learning about your topic.

8. Share the 1 podcast you listen to religiously – and what others will learn from it.

9. Share the 1 Twitter thread you've bookmarked and reread multiple times – and what you learned from it.

10. Share the 1 blog post that once you read, permanently changed the way you see the world.

Now, let's dig into Aspirational:

11. Share 1 mistake you made as a beginner – and what you learned from it.

12. Share the single most valuable thing you learned from a mentor.

13. Share your personal story – where you used to be, where you are now, and how you got here.

14. Share 1 piece of advice to your 5-years-ago self.

15. Share 1 common trait of the people you look up to.

16. Share 1 quote you live by – where you found it, and how it impacts you.

17. Share your personal playbook – how you achieved some result and the steps you took to get there.

Finally, onto Anthropological:

18. Share 1 thing you believe that everyone else doesn’t – and why you’re correct

19. Share 1 life-changing realization you made in your 20s that accelerated your success

20. Share 1 bad habit you broke in the last 12 months - and why it was holding you back

21. Share 1 common trait people who fail in your industry have—and how the reader can avoid it

Boom!

Now you have content ideas for the whole of May.
-
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Here's a free 13,000-word Ultimate Guide with everything you need to get started:

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