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.

Dickie Bush 🚢

I used to have one severe addiction:

Planning.

My brain loved the cheap dopamine of gathering:

• Books to read
• Tasks to complete
• And videos to watch

But when it came to taking action, the euphoric rush faded.

What ended my addiction?

This story of two men learning to fish:

The first fisherman heads straight to the marina to buy the best fishing boat money can buy.

He specs out a custom, carbon fiber rod.

And he spends time reading up on everything there is to know about fishing:

• Casting techniques
• Baiting techniques
• Reeling techniques

You name it, he's bought the book on it.

And of course, he's watching the fishing channel every night for hours, learning from the best of the best.

A few months later, he finally feels ready to fish.

The next day, he heads out on the lake in his new boat with his fancy rod and wealth of fishing "experience" built up over the last few months.

But six hours in, nothing. Not even a nibble.

What happened?

Turns out, the second fisherman had already sucked the lake dry.

On day one, the second fisherman grabbed a shitty rod, sliced up a hot dog, and went out to the lake.

• The first day, nothing
• Second day, nothing
• Third day, nothing
• One week, nothing

But on the eighth day? His first nibble.

And every day after, he honed his technique.

He found a baiting technique that worked a bit better. Or a new spot with a few more fish.

And after three weeks of iteration, he found the winning combination.

Before long, he was hauling in hundreds of fish every day. To keep up with his daily haul, he hired a small team to help him. And from there, he opened a restaurant with fat margins to sell his fresh fish.

And after that, he opened a fishing school to teach others his craft.

He did all of this while the first fisherman sat around gathering gear.

Sure, the first fisherman felt productive. He was "learning" after all, right?

But there was one difference: feedback.

Every day the second fisherman had an idea of something that might work better. And he went right to the market to validate his assumption. If it worked, his strategy improved. And if it failed, he learned something new.

The moral of this story?

Get to action as quickly as possible.

When you find yourself gathering gear, grab a shitty rod and start fishing.

Bad way to learn copywriting:

1. Bookmark dozens of posts
2. Read all the books
3. Apply none of them

Instead, just read The Adweek Copywriting Handbook by Joseph Sugarman.

It taught me more about copywriting than dozens of books combined.

And you can steal Sugarman's 7-step process to write high-converting copy (that helped me generate $15,000,000):

—
📌 Copywriting helped me build a 7-figure writing business.

(While working 12-hour days at my Wall Street job)

But I made my first $10,000 on the internet as a ghostwriter.

And right now, becoming a LinkedIn Ghostwriter is the easiest way to land high-paying clients.

Want to know how to land LinkedIn writing clients in 2025?

Here's a free, 5-day email course on how to get started: https://lnkd.in/eCFfC5cX

7 Steps To Write High-Converting Copy (From Joe Sugarman)

At 24, a stranger on the internet paid me $5,000.

The crazy part?

I thought they'd sent it by mistake!

But I'd actually just stumbled across an insanely lucrative business anyone can start:

Ghostwriting.

Everyone should have writing clients who pay $5,000+ for a project.

(This is ultimately how I quit my job on Wall Street so I could travel and work from anywhere in the world.)

But most people are stuck figuring out:

• What service to sell
• Which clients to target
• How to charge premium rates

So, last month, Nicolas Cole 🚢👻 and I put together the Writer Positioning Playbook to help you:

• Escape the freelancer rat race
• Confidently charge high-ticket prices
• Land ideal clients who value your expertise

Inside, you'll find:

• The 1 simple shift to 10x your rates overnight
• A 3-step framework to upgrade your Positioning
• An AI prompt to find 5 high-paying clients for YOUR specific background

Plus, you'll see real examples from a $3M ghostwriting agency.

Want access?

Comment "playbook" and I'll send it across (for free).

And if we're not connected, send me a connection request with the word "playbook" and I'll DM it to you.

How To Land $5,000 Writing Clients

This French teacher had one goal in mind:

To 4x her income.

Why?

Because Laura B. wanted to fund the work she's most passionate about—teaching her students how to become fluent in French.

So she took the plunge and joined our Premium Ghostwriting Academy.

And as a ghostwriter, she scaled quickly.

She sold:

• 5 Email Courses
• 8 Consulting Packages
• Dozens of Thought Leadership Packs

And now she's using this extra income to build her tutoring business.

Laura's example goes to show that anyone can become a ghostwriter and use this in-demand (and lucrative) service to either:

1. Create a new income stream
2. Or scale their existing income

Because executives, founders, and creators around the world are realizing how much they need a personal brand to scale their businesses.

And the salaries I've seen them pay are wild:

• Content Strategist at OpenAI ($319K - $393K/yr)

• Thought Leadership & Narrative Manager at Google ($211K - $297K/yr)

• Head of CEO Content at PayPal ($137.5K - $236K/yr)

And the best place to start right now is LinkedIn.

Want to start making money as a LinkedIn Ghostwriter?

I put together a free, 5-day email course to help you land high-paying writing clients.

Click "Visit my website" at the top of this post to get instant access.

Helping 9-5 pros build their Corporate Offramp | Land 1st client in a 1-person business you control

You’ve outgrown your 9–5. 
Now what? 

You’ve built a solid career. Maybe even a great one. But lately… 

The Sunday scaries hit a little harder.
You keep wondering, “Is this really it?”

You don’t hate your job. You’ve just outgrown it. And the money is the only part that serves you. 

You’ve done everything right.
But you still feel boxed in by meetings, org charts, and the constant anxiety of “restructuring.”

You know your skills are worth more – but no one’s shown you how to turn them into something of your own.

You're not trying to blow up your life.
You just want to know it’s possible.

That’s what the ‘Corporate Offramp’ is for.

It’s my step-by-step system to help high-performing professionals:
→ Package their skills into a client-ready offer
→ Build a simple audience of people ready to work with them
→ Land their first client in 120 days—without quitting their job

You’ll start earning outside your 9–5 and finally take control of what’s next.

This isn’t about quitting tomorrow.
It’s about progress. Building something – before you need it. 
And when you’re ready to start having control over your time. 

What others are saying:

“What really stands out about Brian is his authenticity. And his responsiveness is in a league of its own. His mix of broad entrepreneurial knowledge, specific expertise in areas like LinkedIn strategy, and straight-talking advice puts him at the top of my list.” 
– Melissa, ex-ed tech exec

“I started building while still in my 9-5, and landed my first client within 3 months (..before being let go by my company!).”
– Cassie, former tech manager

Here’s how to get started:

📥 Grab the Free 5-Day Solo Business Blueprint in my Featured section – and get the exact roadmap to land your first client without quitting your job (or even changing your LinkedIn profile). 

🎯 Want a faster path?
Join me for the Fast Track to Freedom Workshop – where I’ll walk you through:

• What to focus on (hint: not your website)
• Where 90% of your effort should go
• How to build an audience (without posting daily)
• The path to your first paid client – in 120 days

🎟 Save your seat: simplemanguide.com/workshop

Your 9–5 got you started.
Your next move is on your terms.

Brian Gallagher

The real risk isn’t leaving your job.

It’s staying just long enough that the comfort…

Becomes overwhelming.

People frame risk as walking away from stability. But stability’s not real. Just ask the people who thought they were ‘safe’ at Amazon or Microsoft.

The real danger is slower. Quieter.

You start caring a little less. You’re no longer motivated by what you're doing. You move through your days on autopilot.

You get lulled into sleep. Unsure what even makes you feel alive anymore.

You let people steal your time with fake urgency and pointless meetings.
You tell yourself you’ll make a move when things calm down.

But that moment never comes.

I remember when it started happening to me. The pay got better. The hours eased up.

On paper, everything looked fine.

But I didn’t like what the years ahead looked like.

I watched people higher up the ladder still asking permission for the simple things — a doctor’s appointment, a softball game, a random Tuesday.

And I knew if I didn’t draw a line, I might never draw one. I’d wait for the next bonus. Then the next. Then the next.

And 20 years later, I’d be so deep in it that walking away would feel impossible.

That’s how comfort works.
It feels just good enough that you stop questioning it.

Comfort doesn’t just keep you in the job.
It keeps you from becoming the person who’d ever leave it.

It’s a slow slide toward a life you never chose.

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In my last role, I was a VP in investment banking.

On paper? Looked great. But in real life… 

Yikes.

I’ll admit – the instant status it gave me when I told people what I did made me feel important. 

But I was constantly stressed. 

If I wasn’t at the office, I was dreading the next email ping from a managing director. 

Why? Because I had no visibility as to how my week would look. 

One minute I had a long weekend train trip planned. And an email ping could mean having to cancel everything. 

Honestly, it was chaos. 
But I kept telling myself it was “worth it.” 

Everyone seemed impressed with my title, so I was on the right path. That’s what I thought. 

Eventually I caved and said yes to something different. 

I started a fitness studio concept with a friend (while still at my job). 

Just a few classes a week. Nothing fancy.
But it was ours. We made the calls.

It didn’t make me rich. And unfortunately, it didn’t become my forever thing. 

But besides being the most fun I’ve ever had ‘working’, it did something else for me: 

It broke the cycle.

And once I got a taste of calling my own shots,
I couldn’t go back.

Now I help other people build something of their own too.

Because I’ve experienced both sides: 

Waking up dreading the work day. 
Waking up excited about what I get to build. 

And know I’m certain on which I’ll keep choosing.

I did a breathwork session last week.
Two words kept repeating.
And they stayed with me all week.

Kindness.
Vulnerability.

Two simple words. But they are the difference between forcing connection and creating real connection.

Kindness reminded me that everyone I talk to is carrying something I cannot see.

Clients. Prospects. Friends. Family members.
People on here scrolling through their day.

When I remember that, I show up better. My coaching is better. My conversations are better. My patience is better.

Vulnerability reminded me that the people I trust most are the ones who let me see the full picture.

Not the “everything is amazing” picture.
The human one.

So I am choosing to bring more of that into how I show up here.

And I will start today.

I am going through a breakup.

It has been difficult, but being around family, and keeping my schedule full, helps.
Movement helps. And so does work.

And during that breathwork session, something small set me off, and I realized how much I had been holding.

And yes, for a bit, I pulled back on some things while I got my footing again (work included).

But this experience is giving me something important.

A deeper appreciation for how much our personal lives shape the way we show up in our work.

A deeper understanding of what my clients feel when they are trying to build something while holding the rest of their life together.

And a deeper commitment to lead with kindness and vulnerability in every part of my life. Not just my business.

I want the people who follow my work to feel that they are seen, not judged.

And I want them to know that building a solo business is not separate from real life. It happens inside real life.

Work does not happen in a vacuum. Life does not pause while you build something meaningful. 

Who you are matters just as much (if not more) as what you do.

That breathwork session reminded me of that.

And it marked a change how I plan to show up here moving forward.

My brother’s dog, Norman, always helps too :)

There’s a point where learning stops helping — and starts hiding you. Brad was there too…

He’d been reading, thinking, and planning for months, but none of this got him any closer to his goals. 

Until he decided to stop collecting information and start building momentum.

One small shift – a few simple strategies, some accountability, and the courage to share his ideas publicly – changed everything.

The moment that started it all? He hit publish.

From there, things opened up fast.
Conversations he’d never had before.

And new confidence hammered home the realization that he didn’t have to get it perfect to make progress.

That confidence led to real connections, online and in real life.

Soon, Brad was turning his interest in health and leadership into work that actually paid him.

In fact, he’s earned income from three separate and distinct businesses he’s started. 

And now, if a layoff ever came, he wouldn’t panic. He’d have options. And the proof that he can create his own.

You don’t need more ideas. Or more knowledge. You need a first step.

If you’re ready, send me a note and I’ll share what that could look like for you.

The most motivated I’ve ever felt in my work didn’t come after a big win or a big paycheck.

It came on an ordinary morning in New York, with a plan, a coffee, and a blank page.

I remember the first time that feeling hit me.

I’d just gathered feedback on my first product – a simple ebook on slimming down in 30 days. I knew what to fix. The best days were still ahead.

I’d wake up, head to Gregory’s Coffee on 31st and 6th, order a cold brew (jet fuel!), and get creating.

It was the first thing I sold completely on my own. No extra work to deliver.

And when that first email pinged – a stranger had bought my book while I was sitting on my couch reading – I’ll never forget it.

It wasn’t about the size of the sale. It was about the shift it created.

I found the thing that I’d wake up early to build. And I had the plan to do it. 

Finding that bridge is a massive turning point. 

That’s when the work becomes exciting.
That’s when building something of your own becomes the most motivating thing you’ve ever done.

That’s when you stop being an employee in your own career. 

And start being the CEO of it.

At some point, you stop saying you’ll figure it out later – and realize you’ve been circling the same thought for years:

I want to start my own thing, but I don’t know where to begin.

And then the questions start to pile up: 

What would I even do?
How do I start without risking what I’ve built?
What if I fail and regret it?

So, you wait. I see it all the time.

People reach out, we talk about what their next move could look like, and then they disappear. A year later, sometimes more, they come back – same job, same questions, same stuck feeling.

Sure, they saved money by waiting. But they lost something more valuable. 

Time.

Until one day, they look up and realize a decade has gone by in a job they knew stopped fitting years ago.

I get it. I was there too. 

At first, there’s doubt.

You scroll through other people’s posts, quietly wondering if you could ever do what they’re doing. You change jobs, hoping a new title will make it feel different. It doesn’t.

Then comes curiosity.

You start exploring what your skills are really worth. You tinker with ideas. Maybe you even earn a little money on the side. Enough to prove it’s possible.

After that, something subtle changes.

You stop asking if you’re capable and start noticing opportunities everywhere.

People ask for your help. You begin to realize your job isn’t your identity anymore. It’s just your funding.

Eventually, confidence replaces doubt.

Your one-person business starts bringing in real income. You feel in control again.

And one morning, you sit down at your laptop and think, this is my life now.

That’s when you understand: you had it in you all along. 

You just needed a plan.

If you’re somewhere between doubt and confidence, the live workshop starts in a few hours – a free working session to map your first steps toward your off-ramp.

Join us here → https://lnkd.in/dbBue_6h

I had an eye-opening call with someone last week. 

It made me realize what a job interview really is… 

It’s an audition for your own career. 

The person on the call said: 
“I’m done. I never want to go through another interview again.”

They’re tired of pretending and of being told no by people who never really saw them.

The anxiety. The prep. The “hope you get lucky.”

The rounds of interviews where you give your best self, only to get ghosted, rejected, or land in a role nothing like what you were promised.

You’re totally auditioning. And I remember that feeling well.

Always second-guessing and doubting myself. 
Wondering if one wrong answer or one bored hiring manager was going to cost me the life I was hoping for.

That’s why twenty years without a job interview feels like a milestone.

It’s not just freedom from a boss, but freedom from depending on someone else – for them to reply, to notice, to choose you.

You start moving on your own terms again.

Building your own business gives you a different kind of safety. The kind that comes when you stop waiting to be chosen.

That moment when you realize you’re done interviewing is quiet, but it changes everything.

If you’re there now, I’ve put something together that might help:

Free workshop tomorrow → https://lnkd.in/dbBue_6h

And just maybe – you’ve already had your last job interview.

“It’s been four months and I still feel stuck.”
Someone told me this the other day.
Here’s what many underestimate when starting out: 

Just how easy it is to waste time trying to figure everything out on your own. 

And when building while still employed, it’s not helpful to see 15 different paths. All promising places to start, but unsure as to which is most viable. Which leads to revenue fastest. Which has the least speed bumps. 

So what do I see most people do? 

Dabble. Start researching. Build a website. 
Try one thing, then second-guess themselves and switch. 

And four months go by. Then six. Then a year. 

And somewhere quietly in the background, they’re thinking:
“I thought I’d be further along by now.”

Time spent stuck doesn’t just slow you down.
It starts to convince you maybe you weren’t meant for this.

You can figure it out alone. Lots of people do. 
But it usually takes them 18–24 months of guessing, circling, rebuilding, and trying to reverse-engineer the right sequence.

Or…

You get help. You get a map. You talk to someone who’s already walked the road.
And you collapse that timeline down to a fraction of what it would’ve been.

Some of my clients have signed their first client in less time than most people spend thinking about how to start.

Most people don’t fail.
They just run out of time and energy they didn’t know they were burning.

So if you’re four months in and still stuck, nothing’s wrong with you.

You’re most likely trying to navigate a process in the dark that someone could’ve lit up in a single conversation.

The question is no longer:

Can you do it alone?

It’s:

How much is the extra 12–18 months worth to you?

Here’s how I started my first business.

(Hint: it did not go as planned.)

• Spent 6 months writing a business plan
• Paid $6,000 for a logo and brand kit
• Built a full website
• Lined up investors
• Took meetings with anyone who would give advice

And here’s how it went: 

Our branding was off. 
The main part of our class wasn’t engaging. 
We were guessing the entire time.

We didn’t learn this through planning. 
We learned it the moment we actually taught the class.

Direction came from doing the work.
Not preparing to do it.

After making every early mistake, here’s how I get clients started now:

1/ They get clear on their Big 3
The person, the problem, the outcome. 

2/ They clean up their online presence
Simple and easy to understand. 

3/ They grow an audience of relevant people
Not big. Relevant.

4/ They start real conversations
No pitching. Just being human.

Here’s what happens when you start like this:
• Anton had inbound conversations within two weeks.
• Marie signed her first client in under three months.
• Brad generated income from three different offers he created himself.

The confidence came after the action.
Not before.

It’s not that you can’t do it. It’s that it’s unclear what to do first.

Once you know the right sequence, the whole thing gets simpler.

We’ll walk through that sequence together in my live workshop on Tuesday. 

Join us here:

Open article: Workshop by simplemanguide.com

The hard part isn’t choosing.
It’s what happens before that: 

The limbo.

You go back and forth, trying to anticipate what you’ll lose with each option. You imagine every scenario, weigh every angle, and start thinking in circles.

Eventually, the pressure of not deciding becomes heavier than the decision itself.

And in the middle of all that, it’s easy to lose sight of what you might gain – not just from the path you choose, but from the clear vision and calm that comes after you choose it.

Once the decision is made, things get lighter. You can focus again. You’re no longer trying to live in two futures at once. You can stop running through pros and cons and finally begin shaping a plan around the direction you picked.

Starting a business is like this for a lot of people.

They think about it for months. Sometimes years. They wait for perfect timing, or a sign. They watch others do it but tell themselves they’re not quite ready.

What could be a season of momentum turns into a season of idleness. Moving – but not really going anywhere. 

Either way, you’re expending energy.

One way, you’re using it to your advantage.
The other – it just drains you. While nothing changes in your life.

And the longer you wait, the heavier it gets.

If you’ve been struggling to figure out the right next steps, and feel like you’ve just been swirling around in uncertainty… 

I’m hosting a free, live workshop this Tuesday to help lay out the roadmap for you. 

It’s for the ones who feel the pull to build something real – but also value the stability they’ve worked hard for.

We’ll cover:
• How to craft your elevator pitch
• Who to help, and how to reach them
• What to do first to land your first client

Join us here: https://lnkd.in/dbBue_6h

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The Battle

Dickie Bush 🚢

Brian Gallagher

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The Battle

Dickie Bush 🚢

Brian Gallagher

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Dickie Bush 🚢's LinkedIn Performance

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