5 books that helped me reinvent and keep going

I had no idea what I was doing in 2018, when I launched my Amazon business, selling card games that help people develop emotional intelligence skills. 

At the time, I had two part-time jobs, was getting a full-time master’s degree at Harvard, and was raising three young kids. I had to squeeze in my side hustle alongside all my other obligations. 

Just as I gained traction, a few years later, bringing in over $1.7M a year in sales, the economy shifted, consumer habits changed, and competition grew. The number of card games on the market surged while consumers tightened their wallets in response to economic uncertainty. I didn’t give up. Instead, I was able to adapt and find even greater success than I anticipated.

Today, I have five income streams (and counting). I’ve learned that the real work in building wealth isn’t just about starting, it’s about staying in the game through ongoing reinvention. 

Markets have cycles. Many side hustles have expiration dates. The mental game of entrepreneurship depends on your ability to stay agile, adaptive and resilient in the face of uncertainty.

These five books didn’t just help me get started. They’ve helped me evolve, recalibrate, and keep going.

If you want to build lasting wealth, you need a framework for making smart, strategic decisions. In this book, academic and entrepreneur Scott Galloway breaks down four key variables for financial security: discipline, stoicism, time and diversification.

This playbook pushed me to ask not just what I can do, but what’s truly worth doing with my limited time and energy. It helped me reevaluate how I weigh risks, spot opportunities, and make trade-offs across my income streams.

Whether you’re working toward your first six figures or scaling your next income stream, this book offers pragmatic action items to help you build better financial habits and make more informed decisions.

One of the hardest parts of starting and running a business is making decisions without all the facts. In “Thinking in Bets,” Annie Duke — a former professional poker player turned decision strategist — teaches readers how to evaluate their choices by thinking in probabilities, not certainties.

This book taught me to separate luck from skill, and outcome from process. Just because a decision didn’t work out, doesn’t mean it was the wrong call. And just because a decision worked, it doesn’t mean it was a smart move. 

That perspective shift gave me the clarity to take bolder risks, grounded in logic, rather than emotion.

Her “thinking in bets” framework encouraged me to ask myself: What are the odds this will work? What’s the downside if it doesn’t? This helped me navigate uncertainty with more confidence and fewer regrets.

This book is a master class in long-term thinking, rational decision-making, and investing. It compiles eleven of the late Charlie Munger’s most influential talks.

Munger, known for his enduring work with his long-time friend Warren Buffett at Berkshire Hathaway, was renowned for his multidisciplinary approach to decision-making. 

I appreciated how this book taught me how to think, not just what to think. I learned to apply the principles of psychology, economics and engineering to make better decisions in business and in life.

One of his signature ideas, “invert, always invert,” taught me to examine problems from the opposite angle. This mindset has helped me to work through complex dilemmas and mental roadblocks. I still revisit this book to sharpen my thinking when the path forward feels uncertain.

Every business moves through phases of ascent, plateau and decline. Author Ryan Holiday shows how unchecked ego can sabotage success at every stage — whether you’re turning a profit, becoming a viral sensation or facing tough setbacks.

Through historical examples and personal anecdotes, Holiday explores how ego clouds our judgment, resists feedback and blinds us to our shortcomings. In my keynote speeches on emotional intelligence, I often emphasize the same idea to leaders and teams I talk to: self-awareness is your edge.

This book helped normalize the highs and lows I’ve experienced as a founder and creator. It also gave me foresight into the potential scenarios I might face in the future. Most of all, it reminded me to be clear-eyed, grounded, and vigilant about not being influenced by an undue sense of self-importance.

How do we know when it’s time to change course? This book explores that exact question, and reminds us to pause and listen to our inner voice over the noise around us.

Transitions in business and life often go hand in hand. They bring discomfort, uncertainty, and the temptation to rush through the hard parts. But “the next day” after a big decision is when we begin to consciously choose what to carry forward and what to leave behind.

This book has provided comfort and clarity, and helped me navigate both personal and professional shifts. It reminds me that starting over is still forward motion, and the way that I handle change can shape everything that comes next.

Dr. Jenny Woo is a Harvard-trained educator, EQ speaker, investor and the founder and CEO of Mind Brain Emotion. She created a series of educational card games and mental health tools to help kids and adults develop human skills in the age of AI. Her award-winning card games, the 52 Essential Coping Skills, 52 Essential Relationship Skills, and 52 Essential Social Dilemmas are used in more than 50 countries. Follow her on LinkedIn, Instagram, and YouTube.

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