10 Books That Helped Me Lose 100 Pounds, Gain Control Over My Mind, and Quit My Job On Wall Street To Build My Own Business

After reading 60 books in 3 years, these are the only ones I'm revisiting

Last week I received this text:

“Could you share a list of the 10 books that most impacted your life?”

Without overthinking it, I rattled off this list and hit reply:

• Efficiency by WallStreetPlayboys

• The Almanack of Naval by Eric Jorgenson

• The War of Art by Stephen Pressfield

• Think and Grow Rich by Napoleon Hill

• Meditations by Marcus Aurelius

• Own The Day, Own Your Life by Aubrey Marcus

• Awareness by Anthony DeMello

• How To Win Friends And Influence People by Dale Carnegie

• Mastery by Robert Greene

• The Goal by Eliyahu Goldratt

After hitting send, I realized I had never before reflected on this question.

So, tucked away in the corner of my new favorite Amsterdam coffee shop, I started to reminisce and reflect on each of these books.

• When did I read them?

• What did they teach me?

• Who would I recommend them to?

• Why did these in particular spring to the top of my mind when given this prompt?

And in today’s Digest, I’m going to share my answers to those questions.

Let’s dive in:

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For the first 21 years of my life, I despised reading.

Summer reading was always a slog. Reading comprehension was always my worst test skill. And I dreaded English class, memorizing facts about books I didn’t care about.

But during those 21 years, I actually didn’t need to read any books.

Why?

Because there was a simple roadmap for me to follow. And it’s the same roadmap practically everyone follows. Take these classes, play these sports, talk to these people, participate in these activities—the list goes on and on.

For the first 21 years, life was set up like a bowling alley with bumpers.

Sure, there was a little bit of wiggle room to the right and left, but the direction was clear. And any time I veered too far to the left and right, there were guardrails set up to bring me back to the middle.

But when I graduated, the real world slapped with me a realization that there was no longer a conventional roadmap to follow.

Out of nowhere, the entire game changed:

• No more bumpers to guide me in the right direction

• No more pins set up ahead of me to give me an objective

For the first time in my life, it was on me to build my own roadmap.

And for guidance on creating that roadmap, I dove into the world of books.

In the beginning, I wasn’t quite sure what I was looking for.

But I figured these books would either:

• Help me find answers to my questions

• Help me find better questions to ask

So during the years of 2018, 2019, and 2020 (ages 22-24) I read roughly 60 books across dozens of different genres:

• Writing

• Self-help

• Business

• Philosophy

• Spirituality

• Productivity

• Relationships

• Science Fiction

• Health & Fitness

I was constantly inhaling information during my free time.

• One chapter every night before bed like clockwork

• Audiobooks during my commute to and from work

• 4-5 hours of reading at local bookstores every Saturday and Sunday morning

And don't get me wrong—this period of aggressive learning and consumption set the foundation for personal progression that would come in the years to follow.

But looking back, I certainly spent too much time in this consumption mode.

My reading started out as productive but slowly morphed into nothing more than procrastination. I fell into the trap of reading for the sake of reading, rather than for a specific reason.

So of the 60 I read, these are the 10 I wish I could go back in time and read first.

And rather than reading the other 50, I would tell myself to reread these 10 (which is exactly what I’m going to do over the coming months and quarters).

Now, let’s get into the list:

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Efficiency by Wall Street Playboys

Of all the books on this list, this one changed my *trajectory* more than any other.

I picked it up in April 2020, alone in my New York City apartment during the peak of COVID. I was 2.5 years into working on Wall Street, staring down the fact that I did not see myself staring at charts and predicting the economy for the rest of my life.

Recently relegated to working from home, I was dead-set on using the extra free time to build skills that would eventually allow me to leave.

From the first page, this book slapped me in the face with harsh truths I desperately needed to hear.

• It opened my eyes to the importance necessity of starting my own business on the side while working a full-time job. 

• It laid out a logical argument that concludes the only path to wealth (or, at least the wealth I was looking to accumulate), came from having uncapped upside in something

• It walked through the importance of optimizing my health so I could work as hard as I possibly could in my 20s

• It introduced me to the idea of “investing” my money rather than spending it—but not just in stocks or crypto

• It broke down the skills needed to succeed in the world of digital business: writing, marketing, and sales. 

And most of all, it showed the importance of starting the journey of business & health optimization as early as possible.

Every day that goes by makes it harder and harder to build these foundations. Life’s responsibilities start to creep in and putting in intense periods of effort becomes impossible.

Luckily, I found it at age 24 while there was still time to make a change.

But, a quick heads up: this book is not for everyone. Their writing style is rough and to the point. They have controversial opinions on plenty of topics that I don’t necessarily agree with.

And it is *literally* written for dudes like me in their 20s working on Wall Street who want to eventually work for themselves. 

So if I could gift one book to every 20-something corporate worker in the world, it would be this one. But for practically everyone else, it’s irrelevant.

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The Almanack of Naval by Eric Jorgensen

This one is my go-to guide for building wealth & happiness.

Before Eric Jorgenson published this book, all of Naval’s ideas were spread sparsely around different corners of the internet. One-off podcast appearances here. Tweetstorms and off-the-cuff frameworks there. Tons of valuable information wherever you looked, just poorly packaged.

But this book solved that problem by curating and combining Naval’s thoughts and frameworks through thousands of hours of distillation.

For anyone new to the world of digital business, I recommend picking up a copy of this book, reading his How To Get Rich (Without Getting Lucky) Twitter Thread, and listening to the audio version that expands on each idea in the thread. 

The perfect summary of the book comes via the last page, where Naval shares his “life formulas”

Naval’s Life formulas

• Happiness = Health + Wealth + Good Relationships

• Health = Exercise + Diet + Sleep

• Exercise = High-Intensity Resistance Training + Sports + Rest

• Diet = Natural Foods + Intermittent Fasting + Plants

• Sleep = No alarms + 8–9 hours + Circadian rhythms

• Wealth = Income + Wealth * (Return on Investment)

• Income = Accountability + Leverage + Specific Knowledge

• Accountability = Personal Branding + Personal Platform + Taking Risk

• Leverage = Capital + People + Media + Code

• Specific Knowledge = Knowing how to do something society cannot yet easily train other people to do

• Return on Investment = “Buy-and-Hold” + Valuation + Margin of Safety

Hard to go wrong with these as your guide.

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The War of Art by Stephen Pressfield

I picked this one up at the local bookstore in February of 2020, right when I started building my daily writing habit.

After churning through its ~120 pages in one sitting, I realized my last 3 years of “planning to start writing” wreaked of The Resistance.

Now, what is The Resistance?

Pressfield describes it as the powerful, universally experienced force that keeps people from reaching their potential.

For examples of activities that elicit The Resistance, I can pull directly from the book:

1. Pursuit of any calling in writing, painting, music, film, dance, or any creative art

2. Launching of any creative art

3. Launching of any entrepreneurial venture or enterprise

4. Any diet or health regiment

5. Any activity whose aim is tighter abdominals

6. Any course or program design to overcome an unwholesome habit or addiction

7. Education of every kind

8. Any act of political, moral, or ethical courage, including the decision to change for the better some unworthy pattern or thought or conduct in ourselves

9. The undertaking of any enterprise or endeavor whose aim to help other people

In other words, any act that rejects immediate gratification in favor of long-term growth, health, or integrity. Or, expressed another way, any act that derives from our higher nature instead of our lower. Any of these will elicit Resistance.

Acknowledging (and overcoming) the Resistance is something I think about on a daily basis. 

I’m feeling it right now after putting off writing this newsletter for multiple hours this morning. I’ll feel it later when I’m making the choice of what to have for dinner (debating between something healthy and something delicious from a local Dutch pastry shop). And I’ll feel it once again when I get home and face the temptation to doomscroll Instagram Stories rather than plan the next day’s writing session. 

Importantly, this book does not help you defeat The Resistance. In fact, it’s nothing you will ever defeat. Instead, it simply makes you aware of it so you can acknowledge it, accept it, and march boldly into the face of it whenever it greets you.

So if you find yourself held back by procrastination of any kind:

• Putting off your daily tasks

• Putting off the start of that new project

• Putting off having that tough conversation

Pick this one up, read it in one sitting, and take one step closer to becoming The Professional who overcomes it (rather than the Amateur who succumbs to it).

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Think and Grow Rich by Napoleon Hill

This book was the “first” of many things for me on my journey of self-improvement.

• It was the first self-help book I ever read

• It was the first book I ever listened to on Audible 

• It was the first book I ever actively took notes on while reading

• It was the first book I ever reread (and I try to reread it every couple of years) 

• It was the first book in general I had read in ~8 years when I picked it up during my sophomore year of college

• And most importantly, it was the first book that showed me there was a path to taking ownership and improving my situation without anything more than my own attitude and effort

Now, Think and Grow Rich is perhaps the most cliché self-help book out there. 

But there’s a reason things become cliché—because they are genuinely helpful. 

Do I agree with everything in this book? Not really. 

Are some parts a little bit “woo woo” (like excessive visualization and desire)? Certainly. 

But as an introduction to the world of self-improvement, this book is the best place to start.

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Meditations by Marcus Aurelius

I picked up this ~2000-year-old Stoic text in April of 2019, almost one year into working at BlackRock in New York City.

During my daily subway commute to and from work, I was working my way through older episodes of the Tim Ferriss Show. And in one of his early 2015 conversations with Derek Sivers, both of them mentioned this book (and Stoic philosophy in general) as something that permanently changed their life. This was the first I had heard of Stoicism, so I immediately picked up a copy and dove in. 

Over the 11 weeks that followed, I highlighted and underlined damn near every sentence in this book. 

Just a few pages in, the Stoic fundamentals “clicked” with me right away.

• Having an internal locus of control

• Pursuing nothing but the essentials

• Being disciplined and intentional with my actions

• Recognizing every emotion comes from the story I was telling myself

After this I went on to read William Irvine’s The Guide To The Good Life and Seneca’s Letters From A Stoic, giving me a well-rounded perspective on Stoicism. Each of these is on my list to reread at some point over the next few years.

I highly recommend this one as an introduction to philosophy and for anyone interested in creating their personal “operating system.”

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Own The Day, Own Your Life by Aubrey Marcus

This was the first “biohacking” book I picked up on my health and fitness journey. 

At the time I was around 240 pounds—which was 40 pounds down from my peak weight when I stopped playing football. I had started to gain a little bit of momentum toward optimizing my health, but now I wanted more. After hearing Aubrey Marcus talk on this episode of the Tim Ferriss show, I picked up his book and dove down the rabbit hole.

To this day, no book has had a bigger impact on my health & fitness than this one.

It’s relatively short (~180 pages) and without any fluff—nothing but actionable tips you can instantly slot into your daily routine. 

Sleep, diet, meditation, naps, training, flexibility, hydration, supplementation, caffeination—you name it, this book covers it.

And what I like most about the book is its structure, sequencing through an entire “day in the life” from the second your eyes open to the second your eyes close.

I can trace most of the elements of my morning routine, deep work routine, and evening routine back to the principles this book lays out.

So if you’re looking to take the first (or next) step in your health & fitness “optimization” journey, give this one a try.

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Awareness by Anthony De Mello

One of Tim Ferriss’ favorite questions to ask his guests:

“What book have you gifted more than any other?” 

So when Tim answered his own question with this book, I figured it was worth reading. Especially if he’s gifted it enough to have an entire bookshelf in his house filled with copies of it so he can easily give it to friends and families who visit.

Right away, I recognized this book was different than any other I had read up until that point.

This book taught me two fundamental skills:

1. Self-reflection: It helped me understand how to “detach” from the “I” who observes experience and the “me” who actually experiences it.

2. Processing of negative emotions. It helped me understand the root of all negative emotions comes from the false stories and pereceptions we have about our experiences

Paired with the Stoic texts, these books gave me a “philosophical foundation” that has helped me navigate the world ever since.

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How To Win Friends And Influence People by Dale Carnegie

No other book simplifies the psychology of social interactions better than this one.

And yes, this one is a bit cliché like Think and Grow Rich. But it’s cliché for the same reason—the concepts are universally accepted as helpful and productive. 

In flipping through my notes, I came across my bullet-point summary of the book which I need to revisit more often:

• People want 3 things: to feel important, to believe their way of operating is correct, and to feel their actions and ideas are their own

• To make others feel important, greet them with enthusiasm, help them talk about their interests, desires, and problems, and show them genuine appreciation

• To change someone’s behavior, you need to empathetically see things from their point of view and gracefully show them another way is in their best interest

• To win the agreement of another person to your way of thinking, you first must prevent any kind of defensiveness and align their self-identity with this new way of thinking

Not much more to say about this one other than it’s a fun read that will instantly improve the way you interact & speak with others.

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Mastery by Robert Greene

I still remember picking this book up at the local Amazon Bookstore in New York City’s Union Square. 

It was mid-September, 2019—and I felt stuck.

When I graduated in 2018, I accepted what at the time was my dream job—working as a hedge fund trader at BlackRock.

But 12 months in, I was unsure if this was the path I wanted to take forever. 

I enjoyed the work I was doing—studying markets, economics, and monetary policy—but something didn’t feel right.

• I struggled to get excited working for someone else

• I felt like my learning had slowed down, especially skills I could apply outside of the world of finance

• I recognized it might be ~15 more years of this before I had any real shot at building wealth or having autonomy

• I did not like the idea of living in New York City for the rest of my life

As I navigated this time of uncertainty, I heard Nat Eliason talk about this book on the Made You Think podcast. He mentioned it was the single most impactful book on navigating a career pivot, so I immediately picked up a copy and dove in.

This quote from the first chapter breaks down exactly what the book talks about better than I could:

“The structure of Mastery is simple. There are six chapters, moving sequentially through the process.

• Chapter 1 is the starting point—discovering your calling, your Life’s Task.

• Chapters 2, 3, and 4 discuss different elements of the Apprenticeship Phase (learning skills, working with mentors, acquiring social intelligence).

• Chapter 5 is devoted to the Creative-Active Phase,

• And hapter 6 to the ultimate goal—Mastery.

Each chapter begins with the story of an iconic historical figure who exemplifies the chapter’s overall concept.

The section that follows, Keys to Mastery, gives you a detailed analysis of the phase involved, concrete ideas on how to apply this knowledge to your circumstances, and the mind-set that is necessary to fully exploit these ideas.

Following the Keys is a section detailing the strategies of Masters—contemporary and historical—who have used various methods to advance them through the process.

These strategies are designed to give you an even greater sense of the practical application of the ideas in the book, and to inspire you to follow in the footsteps of these Masters, showing how their power is eminently attainable.”

After spending a few weekends reading it, I better understood the importance of learning skills early in my working career. And since I felt my skill acquisition “slowing down” in my finance job, I knew I needed to pivot.

That realization further sent me down the rabbit hole of digital business and starting a side hustle, which was the fastest “vehicle” to help me acquire new skills (while continuing to work full-time).

And a few years into this journey, I can confirm the path laid out in the book is correct. Today I’m revisiting it to recall the frameworks for the “Creative-Active” phase which I can feel myself transitioning into after years of learning from those ahead of me.

So—if you’re at a point of career transition, uncertainty, or just want a helpful framework for identifying your strengths and navigating your professional growth, I highly recommend this one.

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The Goal by Eliyahu Goldratt

This book introduced the single “concept” that most accelerated my personal & professional growth: the theory of constraints.

The theory of constraints is simple: at any time, there is only things keeping a system from growing. This is known as the “bottleneck.”

To grasp the concept of the “bottleneck,” imagine you have a delicious pancake in front of you, and you want to pour syrup all over it from a bottle. The syrup moves slowly out of the bottle because of the small opening at the top, known as the "bottleneck." No matter how much syrup is in the bottle, it can only come out as fast as that tiny opening will allow.

Now if your goal was to make syrup come out faster, it wouldn’t make sense to add more syrup to the bottle, or to shake it, or squeeze it harder. Instead, you should figure out how to take the top off so the tiny opening was no longer the limiting factor.

Time spent on anything other than removing that bottleneck would be wasted.

And this is exactly what most people do in their lives and businesses. They spend way too much time working on the wrong things, rather than the one most important thing that is limiting their growth.

This concept has been so impactful on my life that I plan on making it the lens through which I view the world.

• I want to turn this newsletter into one that purely talks about “bottleneck thinking” applied to personal progress

• I want to write a business newsletter that applies “bottleneck thinking” to growing and scaling digital businesses

So stay tuned for a deeper dive into this concept and how I’ve applied to just about every area of my life (and how you can do the same in yours).

In the meantime, pick up a copy of this book. And better yet, listen to the audiobook (it’s incredibly well-produced and fun to listen to).

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Boom, that’s it.

I hope you found this list as helpful as I did in putting it together.

Revisiting these notes and the part of my life was long overdue. I see this as an exercise anyone can do, viewed through the lens of writing a recommendation to your younger self about what books to spend more time reading.

Up next for me to is spend time rereading each of these over the coming years to see how my perception and interpretation of them has changed. My guess is I’ll discard some things, pick up new ones, and emerge with a fresh list of frameworks to reflect on and experiments to try.

If you have any questions about these books or anything else, leave a comment or hit reply to let me know—I read and respond to every single one of them

Have a tremendous weekend,

Dickie