Employee to Entrepreneur

Have you ever felt miserably comfortable in your job—secure but uninspired, well-paid but yearning to do something that matters? In Employee to Entrepreneur: How to Earn Your Freedom and Do Work That Matters, Steve Glaveski argues that the path to true fulfillment and freedom lies in transforming your mindset from that of an employee to an entrepreneur. He contends that while technology is radically reshaping the nature of work—automating jobs, disrupting industries, and creating new opportunities—the key isn’t to hide from these waves of change, but to surf them by thinking and acting like an entrepreneur.

Glaveski’s story begins with his own leap from the stability of Macquarie Bank to the risky world of startups. Through failures, pivots, and ultimate success with ventures like Collective Campus and Lemonade Stand, he learned that entrepreneurship is not about chasing unicorns but about building autonomy, experimenting boldly, and finding fulfillment through meaningful work. His experiences frame a practical and psychological roadmap for transitioning from employee mindset to entrepreneurial action.

The Age of Disruption

Glaveski opens with a reality check: technological change is exponential, not linear. Using Moore’s Law—computing power doubles every 18–24 months—he reveals how industries shrink, jobs disappear, and productivity grows without increasing income. The gap between automation and employment is widening, meaning future success demands adaptability. Entrepreneurs, he argues, aren’t victims of disruption—they’re its drivers.

To underline this, Glaveski contrasts old corporate giants like Blockbuster, once employing 60,000 people, with Netflix—a billion-dollar company with one-tenth the workforce. The lesson: companies and individuals must learn to create more impact with fewer resources. You can no longer rely on governments or employers to safeguard your future; you must take ownership of your career and purpose.

From Employee to Entrepreneur

Making the leap involves more than quitting a job—it’s about changing how you think, decide, and act. Employees mitigate risk by planning, analyzing, and waiting for certainty. Entrepreneurs mitigate risk by experimenting, failing fast, and learning forward. Glaveski highlights the shift from talking to doing, from avoiding mistakes to using them as guides toward innovation. He urges readers to embrace what psychologists call a growth mindset—viewing challenges not as threats but as learning opportunities.

This mindset shift means accepting discomfort, uncertainty, and even loneliness. As Nathan Chan of Foundr told him, “None of my friends or family are entrepreneurs… they thought I was an idiot.” But entrepreneurship, Glaveski insists, is a discipline of resilience rather than luck—learning to make friends with failure and pushing forward anyway.

The Framework for Transformation

Glaveski structures his journey through three powerful questions: Why (your purpose), What (your mission, work, or direction), and How (your method and execution). Finding your why means escaping the trap of being miserably comfortable and creating work that aligns with your highest values—freedom, fulfillment, and contribution. Your what connects these values to a concrete venture. And your how is about execution—testing ideas, iterating fast, outsourcing what doesn’t matter, and applying principles like lean startup and 80/20 thinking.

He encourages you to “collect dots” through diverse experiences (learning, travel, podcasts, books) and then “connect them” creatively to find purpose, echoing Steve Jobs’ philosophy that you can only connect dots looking backward. The book’s essence is a call to design your own life, not outsource it to an employer.

Why This Transformation Matters Now

Throughout, Glaveski warns that automation and AI are obliterating structured career paths. Mechanized intelligence is outpacing human adaptability, transforming jobs from law and journalism to accounting and design. Yet instead of despair, he offers optimism: entrepreneurship is the antidote to technological unemployment because it empowers creativity, adaptability, and meaning. He reminds readers that the future doesn’t care about seniority—it rewards those who innovate, experiment, and contribute.

As one reviewer put it, Glaveski’s book is “an antidote to the paralysis by analysis of dying corporations.” It’s not about overnight success—it’s about changing the operating system of your mind. Whether you leave your company or rebuild it from within, learning to think like an entrepreneur will help you thrive in the 21st century workplace.

In Summary

Glaveski’s message is simple but profound: action beats aspiration. The book uses his own failures, learnings, and frameworks to help readers go from comfort to creativity, from employee to entrepreneur, and from idle dreaming to impact. You’ll walk away understanding how to identify your “why,” build around your “what,” and execute your “how” so that your work becomes not just profitable but purposeful. In doing so, you earn not just a living—but your freedom.

Steve Glaveski insists that before you can start a business or build any meaningful innovation, you must first collect the dots—diverse experiences, ideas, and insights across many fields—and then connect those dots through creative synthesis. Drawing inspiration from thinkers like Steve Jobs, Clayton Christensen, and Richard Feynman, he shows that purposeful learning and curiosity form the foundation of creative entrepreneurship.

Why Collecting Dots Matters

Most aspiring entrepreneurs say they don’t know their passion or purpose. Glaveski believes it’s not that they lack one, but that they haven’t been exposed to enough experiences to recognize it. He recounts his own eclectic journey—founding a heavy metal nightclub, working in audit and banking, competing in triathlons, learning languages, and traveling through slums and favelas. Each experience became a “dot” he later connected to launch Collective Campus and Lemonade Stand.

He explains that diverse experiences expand your worldview, sharpen intuition, and enable what Annie Duke calls “associational thinking”—the ability to make unique connections between unrelated ideas. This approach mirrors Frans Johansson’s Medici Effect, where creativity flourished when artists and scientists collided in Renaissance Florence.

Connecting Dots with First Principles Thinking

Once you’ve collected the dots, you must connect them using first principles thinking—breaking down complex ideas to their basic truths and reconstructing them from scratch. Glaveski cites Elon Musk’s method of boiling problems down to fundamental physics-level realities, rather than relying on existing “maps of the world.” He uses creative examples, such as combining parts of a skateboard, bicycle, and motorbike to invent a motorized jetski, to illustrate how deconstruction leads to innovation.

Applying first principles helps you question assumptions, avoid linear improvements, and create breakthroughs. Instead of asking “How can I be better than competitors?” ask “What if the entire premise of this industry is wrong?” (This mirrors Peter Thiel’s approach in Zero to One.)

Where to Collect Dots

Glaveski offers practical channels for collecting dots daily:

• Listen to diverse podcasts—your commute can become a classroom (he cites the popularity of Future Squared and Tim Ferriss Show).
• Read broadly—books from philosophy (Marcus Aurelius) to startup science (Eric Ries) help you think multidimensionally.
• Travel—exposure to different cultures expands empathy and perspective, especially by engaging with unfamiliar communities.
• Attend meetups or conferences—but be intentional. He warns most networking events yield few genuine connections unless you prepare and target conversations thoughtfully.

Intentional Learning

Learning becomes valuable only when it’s deliberate. Glaveski advises carving out distraction-free time weekly, using tools like RescueTime to monitor habits. Treat this commitment like training at a gym—seeing results will reinforce discipline. To retain and apply knowledge, he uses Tim Ferriss’s DiSSSCaFE method: simplify learning to its smallest parts, focus on high-leverage 20%, use mnemonics, and teach others. Teaching, he says, is the best form of integration.

Strong Opinions, Loosely Held

To make learning stick, you must stay open-minded. Glaveski urges readers to adopt psychologist Adam Grant’s mantra: “Strong opinions, loosely held.” This means welcoming contradictory evidence as a path to truth, not as a personal attack—an antidote to echo chambers in social media and politics.

Collecting and connecting dots is not about chasing knowledge for its own sake; it’s about synthesizing perspective into purposeful action. As Glaveski writes, “Go wide and deep.” Each new dot—each experience—becomes a resource waiting for connection. You can’t know how it will matter yet, but someday, when the dots align, your purpose will reveal itself.

Glaveski’s mantra, “Without purpose, nothing should be done,” encapsulates the emotional core of Employee to Entrepreneur. He argues that most people languish in careers that are safe but devoid of meaning—what he calls being ‘miserably comfortable.’ Escaping that comfort means uncovering your why, the motivator that drives action even when logic says stop.

Finding Meaning Beyond Money

Through evocative stories from his own consulting days at EY and Macquarie Bank, Glaveski reveals the emptiness of corporate life. After years of writing reports and attending meetings, he asked himself: “What did I actually contribute today?” That moment of painful clarity became the spark for his entrepreneurial journey.

He introduces the “5 Fs” of fulfillment—freedom, financial independence, fulfillment in work, fitness, and family/friends—to evaluate whether your life aligns with your values. If one of these areas falters, change becomes necessary. The first step toward entrepreneurship isn’t filing paperwork—it’s acknowledging what’s missing in your work.

Purpose as a Performance Enhancer

Purpose, like adrenaline, fuels extraordinary effort. Glaveski cites the story of Tom Boyle, who lifted a 1500-kilogram car off a trapped cyclist—a feat of superhuman strength powered by purpose, not muscle. The same force drives entrepreneurs through the exhausting early years when results are invisible.

He aligns his counsel with Maslow’s hierarchy of needs. Once physiological and safety needs are met, true fulfillment comes from self-actualization and self-transcendence—contributing to causes beyond oneself. Viktor Frankl’s Man’s Search for Meaning resonates here: happiness ensues from serving something greater than self-interest.

Exercise: The Five Whys

To unearth your purpose, Glaveski proposes an introspective drill borrowed from Toyota’s problem-solving method: keep asking “Why?” five times. Each layer reveals deeper motivations. For example, “Why do I want to start a business?” might begin with “for independence” and end with “to show my children what’s possible.” He emphasizes objectivity—distinguish genuine reasons from excuses.

From Reflection to Action

Purpose must eventually express itself through action. He recounts receiving an email from “Alex,” an 11-year-old graduate of his Lemonade Stand program who launched an online paddleboard store. Alex’s pride, resourcefulness, and gratitude symbolized what meaningful work should feel like—a reflection of purpose, not obligation.

Glaveski warns against waiting for the perfect moment. “It will never be the right time,” he writes, echoing Jon Acuff’s Do Over. The only time is now. Even small beginnings—a side hustle, volunteering, or part-time passion project—can reveal your why. In doing so, you stop living for Fridays and start living with purpose every day.

Once you’ve defined your why, Glaveski challenges you to embrace your what—the work that brings your purpose to life. It’s about transforming intention into enterprise and translating motivation into measurable impact. Through personal experiences, decision-making frameworks, and philosophical reflections, he shows how to convert inner clarity into outer action.

From Vision to Venture

Glaveski’s story with Hotdesk is a cautionary tale: his startup connected people with unused office spaces, an early ‘Airbnb for offices.’ Despite raising $150,000, he eventually shut it down—realizing he had drifted far from his deeper purpose of empowering people to do meaningful work. Misalignment between why and what kills persistence. Without alignment, effort becomes mechanical. He reframed his purpose and founded Collective Campus, which now helps corporations innovate and individuals rediscover fulfillment through entrepreneurship.

Better Decision-Making

To bridge vision and execution, Glaveski introduces a powerful six-step decision-making framework. From identifying which decisions matter (“Do nothing” is still a decision) to rating options using weighted scoring, he converts intuition into practical judgment. He calls this “data-informed decision making” rather than “data-driven,” blending analytics with human insight. Techniques like planning poker and team rating prevent groupthink and reduce emotional bias.

He also introduces your inner opponent—the Instant Gratification Monkey, borrowed from Tim Urban. This creature pushes you toward short-term pleasures and away from long-term goals. Recognizing this inner saboteur helps you resist distractions and delay gratification, a crucial entrepreneurial skill.

Seeing Opportunity Through New Maps

Old mental maps—corporate hierarchies, fixed salaries, and predictable promotions—no longer describe the real world. Glaveski compares using old maps to sailing with 1500s navigation charts—you’ll drift in circles. Instead, redraw your worldview based on possibility, not stability. Lower barriers to entry mean almost anyone can launch a product today for under $100, using platforms like Shopify or podcasts. This democratization of creation makes entrepreneurship more accessible than ever.

He warns against self-defeatist salary expectations. Many people trade freedom for predictable paychecks, unaware that happiness plateaus at around $75,000 in income. Seeking fulfillment instead of more money lets you take pay cuts for better purpose—the ultimate investment in yourself.

Is Entrepreneurship Always the Answer?

Despite his advocacy, Glaveski admits entrepreneurship isn’t for everyone. The goal isn’t to start a company—it’s to live with entrepreneurial mindset: ownership, creativity, and initiative. He outlines eleven alternative paths—from intrapreneurship and freelancing to creative side hustles and career pivots—each offering autonomy without starting from zero.

The rule of thumb: don’t jump blindly. Test before committing. Think like Ray Dalio—consider second-order consequences. In big decisions, choose what moves you closer to purpose, not just comfort. As Dale Carnegie wrote, “Action breeds confidence and courage.” Your what is not your job title—it’s the work through which you express your freedom and purpose.

Entrepreneurship, Glaveski reminds us, isn’t about business plans or investors—it’s a state of mind. The true work begins with mastering psychology: cultivating persistence, managing emotions, and reframing failure. This mindset shapes how entrepreneurs act under pressure and interpret uncertainty, differentiating success stories from burnout.

The Trough of Despair

Sooner or later, every entrepreneur hits what Glaveski calls the “trough of despair”—the emotional pit where progress stalls and self-doubt peaks. He compares this stage to Odysseus’ ten-year journey home in Homer’s The Odyssey: fraught with storms, monsters, and setbacks, yet sustained by purpose. The only cure for despair, he writes, is movement—experimentation, learning, and adaptation. As business philosopher Eric Ries says, startups that learn fastest win.

An Operating System for Success

Glaveski outlines four pillars of entrepreneurial success:

• Growth Mindset: Adopt Carol Dweck’s principle that abilities can be developed through effort. Replace “I can’t” with “Not yet.”
• Stoicism and Self-Control: From Marcus Aurelius to modern cognitive psychology, the lesson remains: control your response, not external events.
• Extreme Ownership: Borrowed from Navy SEAL Jocko Willink—radically accept responsibility instead of excuses.
• Meditation: A modern discipline for clarity and emotional resilience. He lists apps like Headspace and Calm, used by leaders from Ray Dalio to Oprah Winfrey.

He fuses these philosophies into a pragmatic ethos: you may not control circumstances, but you control effort, focus, and interpretation. The world rewards adaptability, not certainty. Entrepreneurs thrive by balancing detached objectivity with passionate purpose.

Recognizing Ego and Bias

Human ego, Glaveski warns, is the enemy of learning. He catalogues seven cognitive biases—from confirmation bias to courtesy bias—that distort decision-making and inhibit innovation. Awareness, not elimination, is the solution. He recommends radical honesty sessions (“brain trusts”) like Pixar’s, where feedback flows without fear. Ego blocks truth; humility unleashes progress. (Comparable to Ray Dalio’s radical transparency at Bridgewater Associates.)

Darkest Before the Dawn

Perhaps most moving is Glaveski’s confession of being fired early in his career—a moment he once labeled failure but later saw as transformation. Reframed through Socratic thought (“Know that you know nothing”), it became fuel for growth. The lesson: setbacks are not signals to stop but opportunities to recalibrate your operating system.

The entrepreneurial mindset isn’t genetic—it’s learned through disciplined thinking and conscious awareness. The more you respond rather than react, act without ego, and treat discomfort as data, the closer you move toward mastery—not just of business, but of life itself.

Inspirational ideas mean little unless you act on them. Glaveski’s message here is blunt: “Inspiration without action is entertainment.” Entrepreneurship demands courage to move despite fear—whether financial, emotional, or social. He offers simple frameworks for starting small and maintaining momentum until fear is replaced by confidence.

Start Now, Not Someday

Most people wait for the ‘perfect time’ to pursue ideas. Glaveski dismantles that myth with practical examples from his own ventures. When launching the Lemonade Stand kids’ program, he didn’t spend thousands on branding. He tested demand with a $100 Facebook ad and sold $500 tickets within two weeks. The principle: test your idea fast, fail small, and learn quickly. (Eric Ries’s Lean Startup echoes this approach.)

Every idea faces three risks—financial, technical, and market. Entrepreneurs win by mitigating them with experiments, not reports. A failed $50 test is better than a failed $50,000 product launch.

Small Steps Create Momentum

To fight procrastination, set micro-goals—your “crappy 200 words a day.” Small wins compound into habits and progress. Action itself generates motivation; it’s not the other way around. This concept aligns with Dale Carnegie’s dictum: “Action breeds confidence and courage.”

He also addresses fear of losing financial security. Drawing from his property investments before leaving Macquarie Bank, he shows how strategic planning can create buffers. You don’t need to quit cold turkey—build safety nets to buy time for learning and testing before scaling.

Execution Over Ideas

Ideas are cheap; execution is rare. He reminds readers that action separates wannapreneurs from entrepreneurs. New Year’s resolutions fail because they lack structure. Identifying blockers and enablers—then aligning habits to goals—creates real change. Instead of thinking, “I don’t have time,” recognize that time follows priority.

Ultimately, taking action is about reframing fear. Write down worst-case scenarios, like his colleague Shay did before leaving consulting. Usually, the worst amounts to starting over—a manageable outcome compared to decades of stagnation. The question isn’t “What if I fail?” but “What if I never try?”

Execution without validation is waste. Glaveski merges design thinking and lean startup methods to help entrepreneurs test ideas before investing heavily. His process teaches you to replace assumptions with data and enthusiasm with evidence—so you build what customers actually need, not what you hope they want.

10x Better, Not Just Different

The modern market punishes mediocrity. Customers rarely abandon old habits for minor improvements. Drawing on Seth Godin’s Purple Cow and Clayton Christensen’s Jobs to Be Done theory, Glaveski insists new products must be either half as cheap or ten times better. Incremental tweaks won’t inspire action—remarkable simplicity will.

Design Thinking Framework

He walks readers through the first stages of design thinking: collect insights by engaging, observing, and immersing; define problems through “How Might We” questions; and ideate through divergent brainstorming. Judgment is deferred in early stages—quantity trumps quality. Crazy ideas often incubate breakthroughs.

Once the problem is clear, he transitions to prototyping—mocking up rough versions of solutions to gather real feedback. Entrepreneurs can prototype in a day using ads, landing pages, videos, or paper sketches. Dropbox famously gained 60,000 sign-ups overnight from its explainer video. Glaveski shows that learning fast beats building perfect.

Lean Canvas and Make-or-Break Assumptions

Glaveski replaces traditional 50-page business plans with Ash Maurya’s Lean Canvas. This one-page tool outlines key building blocks—problem, solution, segments, pricing—and isolates “make-or-break assumptions.” Rather than assuming your idea works, test its riskiest assumption first. Prioritize what’s high-impact, uncertain, and testable today using quick experiments.

He then teaches prioritization using Learning-on-Investment (LOI), the ratio between insights gained and time or money spent. High-LOI experiments move you forward fastest. Small tests turn ambiguity into clarity.

Marketing Channels and Metrics

Testing doesn’t end with prototypes—it extends to marketing. Use lean marketing sprints to see which channels work. For instance, compare Facebook ads, content marketing, or SEO. Measure success using pirate metrics (acquisition, activation, conversion, retention, referral). Focus on actionable data, not vanity stats like likes or impressions.

To illustrate, Glaveski recounts Mary, a corporate innovator testing a health app idea with $1000 in seed funding. Her ad campaign revealed that blue-collar workers were most responsive—a pivot that saved months of misaligned development. It’s a vivid example of his core message: measure, learn, adapt fast.

Learning speed equals survival. Just as fighter pilots in the OODA loop (Observe, Orient, Decide, Act) thrive by adapting faster than opponents, entrepreneurs who iterate quickly stay ahead of markets. The faster you replace assumptions with evidence, the closer you move to product-market fit—and sustainable success.

Glaveski believes productivity is the entrepreneur’s greatest leverage. His company Collective Campus, though small, outperforms giants by mastering focus, automation, and flow. Chapter 10 distills his toolkit for multiplying output tenfold through intentional time management, delegation, and mental discipline.

The Power of Flow

Citing psychologist Mihaly Csikszentmihalyi and Steven Kotler’s Flow Genome Project, Glaveski explains that flow is “energized focus”—a physiological state blending alpha and theta brain waves. Executives in flow are 500% more productive. To achieve it, eliminate distractions, match challenges to skill levels, and pursue tasks that stretch you slightly beyond comfort.

Triggers include clear goals, real-time feedback, and high stakes. Meditation, binaural beats, and even listening to repetitive music can induce the state. Flow converts work into play—a concept Kotler calls “the highest version of yourself.”

Killing Distractions

Glaveski’s biggest productivity killer: his smartphone. He used the Moment app to track screen time, discovering he was spending over two hours daily. By leaving his phone outside the bedroom, turning off notifications, and setting a 30-minute screen goal, he reclaimed weeks of life each year. The lesson: tools should serve you—not enslave you.

Delegation and Automation

Entrepreneurs should focus on $1000/hour tasks and outsource $10/hour work. Virtual assistants (VAs), he explains, can handle repetitive tasks—from admin and research to social media and design—at a fraction of the cost. He encourages detailed documentation (“never assume”) and treating assistants as team members through recognition and bonuses.

Automation tools like Zapier and Integromat link apps to perform routine actions automatically—sending emails, updating databases, sharing posts. These small efficiencies compound into time freedom, supporting what Dwight Eisenhower called “focusing on the important, not the urgent.”

Time Management via Agile

Glaveski applies agile principles—stand-ups, Kanban boards, sprints—to personal productivity. Teams meet briefly, report priorities, and remove obstacles daily. He advises three core techniques:

• 80/20 Principle: Focus on high-value activities—the few tasks that drive most results.
• Parkinson’s Law: Work contracts to fill available time; set shorter deadlines to boost focus.
• 13-Week Years: Replace annual goals with quarterly objectives to induce ‘finishing kicks.’

His pragmatic philosophy parallels Cal Newport’s Deep Work: success demands carving out uninterrupted time for complex tasks. The result isn’t burnout—it’s mastery. Productivity, Glaveski concludes, isn’t doing more—it’s doing what matters faster and freeing yourself to live fully.

Entrepreneurship is physically and mentally demanding; without energy, every great idea dies in exhaustion. In his final chapter, Glaveski turns from business tactics to human performance, showing that the foundation for freedom is health, mindfulness, and balance.

Physical Mastery

Exercise is the entrepreneur’s hidden productivity hack. Regular workouts release serotonin, sharpen focus, and improve emotional resilience. Borrowing from trainers like Ben Greenfield, Glaveski recommends morning routines—burpees and cold showers—to build grit. These micro-disciplines teach you to do hard things first, priming confidence for the day.

He also urges movement: stand while working, walk during calls, and use the Pomodoro technique to break sedentary patterns. Even brief activity can slash risks of heart disease and diabetes, proving health feeds success.

Fuel and Focus

Glaveski treats food as fuel, not comfort. He endorses low-GI carbs, good fats, lean proteins, and intermittent fasting—practices that boost clarity and longevity. Supplements like omega-3s and magnesium aid performance, while avoiding sugar-laden smoothies preserves focus. Eating intentionally embodies stoic discipline—control the body to command the mind.

Mind Over Matter

Mindfulness completes the triad. Drawing from Eckhart Tolle and Robert Emmons, he teaches gratitude journaling as a daily reset. Recording three things you’re grateful for rewires perception toward abundance and calm. This mental hydration complements physical exercise—both train endurance and presence.

He warns against mental overstimulation—the same struggle seen earlier with smartphone addiction. Entrepreneurs must guard their cognitive space through stillness, sleep, and disconnection. Measuring your wellbeing (steps, calories, mood) turns health into a feedback system, echoing Peter Drucker’s principle: “What gets measured gets managed.”

Relationships and Freedom

True freedom isn’t isolation—it’s choosing meaningful relationships. Glaveski quotes Epicurus: happiness stems from friendship, freedom, food, and thought. He ties this philosophy to modern entrepreneurship—autonomy without alienation, productivity without neglect. As investor Steve Blank reminds him, “He doesn’t want his epitaph to say ‘He never missed a meeting,’ but ‘He was a great father.’”

In the end, powering up means living purposefully, not endlessly hustling. Entrepreneurship becomes not a job but a way of being—healthy, mindful, grateful, and free to create work that truly matters.