Lessons from the 1%
Subscription Model Coming + Billionaires' Career Advice + Sourcing + Remote Job Announcements
Have you ever wondered what differentiates billionaires like Elon Musk, Oprah Winfrey, Warren Buffett, and others from the rest of the world? Beyond their obvious financial success, they’ve mastered principles that guide their career paths—principles that are often counterintuitive, yet incredibly effective.
In this newsletter, we’re getting into career advice straight from some of the most successful folks on the planet. Their tips might just make you rethink how you approach your job, your goals, and even your coffee breaks. But before we get into that, we have an announcement to make.
Change Is Coming!
We’re excited to share that, as we hit the 42nd edition of our newsletter, we’re gearing up for something new and even more impactful! Starting in the new year, we’re introducing a two-tier subscription model for our newsletter:
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- And more surprises to make your career journey smoother than ever!Why the shift? Because we’re committed to delivering even better content, deeper insights, and exclusive updates tailored to help you grow and succeed—content you won’t find anywhere else. Think of the paid edition as having your personal career coach on demand, helping you build momentum, stay accountable, and achieve results.
By subscribing, you’re not just supporting our mission—you’re investing in your own journey to stay informed, inspired, and ahead in your career. We’d love your support as we take this exciting step forward. Stay tuned for more details, and here’s to making 2025 our best year together yet!
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1. Elon Musk's "First Principles" Approach: Rewrite the Rules
Remember when your parents told you to think outside the box? Well, Elon Musk suggests throwing the box into a SpaceX rocket and sending it to Mars. His "first principles" thinking approach has revolutionized multiple industries, from electric cars to space travel. But what does this mean for us mere mortals who aren't planning interplanetary missions?
Musk's approach is about breaking down complex problems to their fundamental truths and rebuilding from there. Instead of accepting "that's how it's always been done" as an answer, he advocates questioning everything. When starting Tesla, he didn't ask, "How can we make better cars?" Instead, he asked, "What makes a car work, and how can we rethink each component?"
This principle applies brilliantly to career development. Instead of following traditional career paths, ask yourself: What fundamental value do I want to create? What are the basic truths about my industry? How can I reconstruct my role from scratch? One PayPal employee took this approach and completely redesigned their fraud detection system, leading to a promotion and a method still used today.
Practical tip: Next time you face a workplace challenge, resist the urge to follow conventional solutions. Break the problem down to its basic elements and build up from there. You might just revolutionize your corner of the world – and yes, that includes finding a better way to organize the office snack drawer.
2. Sara Blakely's "Embrace Embarrassment" Philosophy: Turn Red Faces Into Green Bills
Remember that time you tripped in front of your entire office? Sara Blakely, the Spanx founder, would tell you to own it – and then maybe turn it into a billion-dollar idea. Before creating Spanx, Blakely spent years embracing uncomfortable situations as a fax machine saleswoman (yes, those were real things, kids).
Her career breakthrough came from what most would consider an embarrassing moment – cutting the feet off her pantyhose to create a smooth look under white pants. Instead of hiding her makeshift solution, she developed it into a revolutionary product. "The more I was willing to be embarrassed and fall flat on my face," she says, "the more success I found."
This approach extends beyond product development. In meetings, Blakely often admits when she doesn't understand something, turning potential embarrassment into learning opportunities. She's famous for asking "stupid questions" that often turn out to be the most insightful ones in the room.
Start keeping an "embarrassment journal" (stay with me here). Document moments that make you cringe, then analyze them for opportunities. That presentation where you fumbled? It might reveal a better way to organize information. That awkward client interaction? Perhaps it's highlighting a gap in your company's service approach.
3. Mark Cuban's "Always Be Learning" Mandate: Your Brain is Your Bitcoin
Mark Cuban, the shark with a bite of wisdom, made his billions by staying ahead of the technology curve. His secret? He reads. A lot. Like, "four to five hours a day" a lot. While we might not all have that kind of time (some of us need to actually sleep), his principle of continuous learning is more relevant than ever.
Cuban started as a bartender who taught himself programming by reading software manuals. Yes, software manuals – the literary equivalent of watching paint dry. But this dedication to learning led him to build and sell multiple tech companies. He famously says, "The best investment you can make is in yourself, and the best return comes from lifelong learning."
Here's the kicker: Cuban doesn't just advocate for formal education. He believes in learning about everything – from AI to zoology – because you never know what combination of knowledge might give you an edge. He once credited his success to combining his understanding of technology with insights from psychology books he read in college.
Dedicate 25 minutes daily to learning something new outside your field. Read about quantum physics during lunch, study ancient philosophy during your commute, or learn about beekeeping while waiting for your coffee to brew. You never know – the solution to your next business challenge might come from understanding how bees organize their hives.
4. Richard Branson's "Say Yes First, Figure It Out Later" Strategy: Calculated Chaos Theory
Sir Richard Branson, the man who turned "screw it, let's do it" into a business philosophy, has built an empire on saying yes to opportunities he wasn't quite ready for. When he started Virgin Atlantic, he knew nothing about running an airline. His solution? He figured it out along the way, surrounded himself with experts, and turned his inexperience into an advantage by questioning industry norms.
This doesn't mean being reckless – it means being resourceful. Branson's approach is about recognizing opportunities and then marshaling the resources to meet them. He calls it "calculated chaos" – taking controlled risks while building safety nets.
True story: When Branson was asked to save a wedding by providing a charter flight to the Caribbean (the original flight was canceled), he had no planes. Instead of saying no, he called around, chartered a plane, and filled it with other stranded passengers to cover costs. Virgin Atlantic was born from this single "yes."
Create a "stretch goal" every quarter that seems slightly out of reach. Then, work backward to figure out how to achieve it. Maybe it's leading a project you're not quite qualified for, or pitching a client that seems out of your league. The key is to say yes first, then leverage your resources and network to deliver.
5. Mary Barra's "Do the Hard Work First" Principle: No Shortcuts to the Corner Office
General Manager's CEO Mary Barra started on the factory floor as an intern and worked her way up to become the first female CEO of a major automotive company. Her career philosophy? "Do the work nobody else wants to do." While others might seek glamorous roles, Barra actively sought out the challenging, unglamorous assignments that taught her the business from the ground up.
This approach isn't about martyrdom – it's about building a foundation so solid that success becomes inevitable. Barra took on quality control issues, managed difficult labor relations, and tackled failing divisions. Each challenging assignment added to her toolbox and reputation as someone who could handle tough situations.
The brilliance of this strategy is its compound effect. While others avoid difficult tasks, those who tackle them head-on build rare and valuable skills. Barra notes that every "impossible" project she completed made the next one easier and opened doors to bigger opportunities.
Make a list of the three most challenging projects in your organization that nobody wants to touch. Volunteer for one. Yes, it will be hard. Yes, it might keep you up at night. But it's these projects that accelerate careers faster than any "safe" assignment ever could.
6. Oprah Winfrey's "Authentic Purpose" Doctrine: Find Your Truth (And Your Ratings Will Follow)
Before Oprah became OPRAH, she was fired from her job as a news anchor for being "too emotional." Instead of changing to fit the mold, she doubled down on her authentic style and revolutionized daytime television. Her career advice? "Your work must become a calling. It has to be something that feeds your spirit."
This isn't just feel-good advice – it's a practical career strategy. When you align your work with your authentic self, decision-making becomes clearer, resilience increases, and opportunities seem to multiply. Winfrey attributes her success not to working harder than others (though she certainly did), but to understanding and staying true to her core purpose.
She tells a story about early in her career when she was trying to copy other successful talk show hosts. Her ratings were good, but she felt unfulfilled. It was only when she started focusing on using her platform to help people improve their lives that her show became a cultural phenomenon.
Write down three times you felt most alive at work. What were you doing? What values were you expressing? Use these insights to guide your next career move. And no, "that time I won the office chair racing competition" doesn't count (unless you're planning a career in professional office furniture athletics).
7. Jeff Bezos's "Regret Minimization Framework": Playing Chess with Father Time
When Bezos left his cushy Wall Street job to sell books online (what could go wrong?), he used what he calls the "regret minimization framework." He projected himself to age 80 and asked which decision he would regret more: trying and failing, or never trying at all.
This framework is particularly powerful because it helps cut through short-term fears and focuses on long-term fulfillment. It's not just about making bold moves – it's about making decisions you can live with for the rest of your life.
The fascinating part is how this framework can apply to smaller career decisions too. Should you speak up in that meeting with senior leadership? Take on that risky project? Learn that new skill? Ask yourself: "At 80, will I regret not taking this chance?"
8. Ray Dalio's "Radical Truth" Protocol: Embrace the Uncomfortable Mirror
Bridgewater Associates founder Ray Dalio built the world's largest hedge fund on a foundation of "radical transparency." In practice, this means creating an environment where everyone – from intern to CEO – is expected to give and receive direct feedback. Sounds terrifying? That's the point.
Dalio argues that most people never reach their potential because they're surrounded by people who either won't or can't tell them the truth about their performance. His solution? Create systems that force honesty. At Bridgewater, every meeting is recorded, and employees rate each other's performance in real-time through an app.
While you might not want to go full Bridgewater in your workplace (instant feedback apps might be a bit much for your weekly team huddle), the principle is invaluable. Actively seeking out honest feedback, even when it hurts, is the fastest way to identify and correct career-limiting behaviors.
9. Zhang Yiming's "User-First" Perspective: See the Future by Understanding the Present
The founder of ByteDance (TikTok's parent company) built his empire on a simple principle: deeply understanding user behavior. While others were trying to guess what people wanted, Zhang was obsessively studying how people actually used technology.
This principle extends far beyond app development. In any career, your "users" might be your colleagues, clients, or stakeholders. Understanding their genuine needs – not just their stated requirements – is what sets exceptional performers apart.
Zhang's approach to career development is fascinating because it's both strategic and humble. He advocates for spending time in the trenches, actually using your product or service, and regularly stepping into your users' shoes. At ByteDance, he would spend hours using competing apps, reading user comments, and testing new features himself.
Spend one day a month doing the job of your end users. If you're in software development, use your software for real tasks. If you're in sales, try being a customer of your own product. The insights gained from this exercise can be career-changing.
10. Warren Buffett's "Circle of Competence" Strategy: Know Your Lane (Then Own It)
The Oracle of Omaha has a simple but powerful career philosophy: understand what you're good at, then go all in. Buffett famously stays within his "circle of competence," focusing on investments he understands and avoiding those he doesn't – no matter how attractive they might seem.
This isn't about limiting yourself; it's about being strategic with your energy and resources. Buffett suggests that success comes not from having a massive circle of competence, but from knowing where your circle's boundaries lie and operating powerfully within them.
The genius of this approach is that it encourages depth over breadth. Instead of trying to be good at everything, focus on becoming exceptional in your areas of natural strength. Buffett never tried to become a tech guru or a real estate mogul – he stuck to what he understood and became the best in the world at it.
Create a "Circle of Competence" map. Draw three (3) circles:
Inner circle: Things you do exceptionally well
Middle circle: Things you're competent at
Outer circle: Things you should delegate or avoid Focus your career development on expanding your inner circle rather than trying to eliminate your outer circle entirely.
"Success is not final, failure is not fatal: it is the courage to continue that counts." - Winston Churchill (who wasn't a billionaire, but definitely knew a thing or two about persistence)
We’re Sourcing for an Enterprise Application Integration Engineer!
A Florida-based company is seeking an Enterprise Application Integration (EA) Engineer for a hybrid role (3 days on-site per week). The focus is on migrating legacy systems, implementing modern data integration solutions, and collaborating with cross-functional teams.
Highlights:
Based in Tallahassee, Florida
7+ years of Informatica Cloud Data Integration experience
Strong SQL skills (DB2, SQL Server, Snowflake)
Expertise in ETL/ELT pipelines and cloud data solutions
If interested, send your resume to hello@udeserveitconsulting.com!
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