đź“– The Upside of Uncertainty by Nathan Furr & Susannah Harmon Furr

A Guide to Finding Possibility in the Unknown
This book has become one of my favorite and meaningful book of 2022. I began reading this book as I began my Chemotherapy to fight the cancer in my body. It activated and unlocked possibilities in a season of great uncertainty by helping me move to a “Discovery-driven action” mode of living.
This book is full of tools to help transform the negative (destructive) energy that can come from uncertainty to positive (constructive) energy. It breaks down the tools to four categories: Reframe, Prime, Do, and Sustain.
In Summary, there are four key approached:
- “Reframe uncertainty as essential portal to opportunity and consider all the possibilities you can imagine. Acknowledge self-doubt as a normal part of every hero's journey.”
- “Prime yourself and the uncertainty you face with self-knowledge, research, balancers and supporters, and a collection of real options and potential exit strategies.”
- “Face every uncertainty based on values, cognitive flexibility, and curiosity to reveal the essence waiting to be activated and unlocked. Be prepared to take ten thousand shots, experiment, and use bricolage to bring it to life. Those aren't weaknesses - that's how the brightest possibilities are born.”
- “Sustain yourself and your projects with emotional hygiene, reality checks, and magic.”
"For all of us, uncertainty is arguably the portal to every growth, change, and courageous act we will ever undertake. It attends every invitation to CULTIVATE A MORE MEANINGFUL, INSPIRED, and AUTHENTIC LIFE.”
"When we meet uncertainty from this expanded sense of possibility, DOING becomes AN IMAGINATIVE, GENERATIVE, DISCOVERY-DRIVEN ACTION.
"If it is the challenging nature of life's perils that enable the wider world with hopes and yes, fears, we can all learn to be more eager about uncertainty. All it takes is an earnest longing to find the upside. If you can do that, you will find one.”
There are my top 3 tools from category (Sustain has 3 additional categories)
Reframe Tools (Top 3)
It starts with how you choose to see. It starts with “undergoing a radical shift in perspectives”. Instead of fearing and avoiding the unknown, “you recognize and embrace it as the origin of possibility”. We are learning to transform “evolution responses - where uncertainty is inherently bad” to “transilience responses - where possibility always bring uncertainty.”
- FRAMING - “When you frame uncertainty as possibility, your ability to navigate it increases because you experience shifts from the fear of loss to the anticipation of gain.”
- "Psychologist argue that FEAR OF THE UNKNOWN may be the fundamental fear underpinning all other anxieties."
- "Empirical research suggest we are motivated by fear of loss more than by the potential for gain" - 2x as much
- "Begin by framing yourself as someone who has enough courage to stand at the edge of opportunity".
- Edge of opportunity = lots of uncertainty
- FRONTIERS - “Frontiers can be daunting, but they are where we do our best work. There are myriad accessible frontiers awaiting us that could transform our daily lives.”
- Frontier - "is really any boundary between where we feel comfortable and where we don't."
- Liminal Space - the in-between - where we learn, discovery and grow.
- "Anyone can achieve their fullest potential; who we are might be predetermined, but the path we follow is always of our own choosing. We should never allow our fears or the expectations of others to set the FRONTIERS OF OUR DESTINY." - Martin Heidegger, German Philosopher
- INFINITE GAME - “Infinite players learn to question the boundaries, the rules, and the game itself, reinventing both the games they are playing and themselves.”
- "For finite players, uncertainty is the enemy because it creates unknowns about the ability to win. For infinite players, uncertainty is the realm of opportunity, and they play with the "expectation of being surprised."
- "Infinite players play WITH the roles and bend the rules, NOT TO WIN the game but for the joy of playing."
- The Game of Life - Not winning but the joy of playing.
- "Infinite players CHALLENGE THEIR ROLES."
- "...if we view our roles as temporary, changing, and separate from who we really are, then we are more free to experiment, reinvent, and transform them."
- David Lynch (Filmmaker) - "We think we understand the rules when we become adults but what we really experience is a NARROWING OF THE IMAGINATION."
- CHALLENGE YOUR ROLES, THE RULES, EVEN THE GAMES you are playing, and CREATE A LIFE of CONTINUED PLAY and NEW POSSIBILITIES.
- Additional Reframe Tools
- Adjacent Possible - “Adjacent possibles are the infinite ways in which the future can be reinvented, hovering at the edge of awareness, waiting to be discovered.”
- Reverse Insurance - “An instinctual fear of uncertainty sometimes leads us to forget that we also need uncertainty. Humans need surprise, spontaneity, and change - and those things are inherently uncertain.”
- Stories - “We live by stories, but you need to think about what kind of story you are writing each day and what you would like to be able to pull off the shelf at the end of the year - or at the end of your life.”
- Uncertainty Manifesto - “A personal uncertainty manifesto or aspirational beliefs in the face of uncertainty can provide resilience when the going gets rough.”
- Regret Minimization - “How do you make decisions when you don't know the outcome? Simple frameworks used by innovators help you to make wise choices.”
- Aplomb (Doubting Self-Doubt) - “Self-doubt accompanies the unknown. What we don't realize is how many people, including our heroes and geniuses, share it. There is a better way.”
Prime Tools (Top 3)
“Priming is about getting ready for what’s next.” Have you cultivated your life to harvest the opportunities that grow from the seeds of opportunities. Seth Godin encourages us to change our strategy from Hunting/Fishing to Farming. Hunting give you a subset because it is divisive. Where as farming gives you growth because it is multiplication. Here are top 3 favorite tools that will help us become better “farmers”.
- FAIT SURE MEASURE - Sometimes we fall into the trap of following someone else's plan for our life. WE FORGET THAT WE CAN, AT ANY TIME, CUSTOMIZE OUR LIVES IN BRIGHT AND BEAUTIFUL WAYS. Your life should be, as the French say, fait sur mesure - made to your measure.
- Fait Sur Measure - the ideal day, the ideal week, the ideal life
- The designed life
- "Don't get the wrong idea: fait-sur-measure lives are not about changing all the time or being unreliable...They took their extremely personal vision, with all its wondrous creativity and oddity, and then PRIMED FOR IT - thoughtfully measured, planned, and lived it into reality in a very dogged, practical, even rigorous way."
- "Research confirms that people who ruminate on the paths not taken underperform at work."
- Regret is emotionally draining and undercuts our performance
- UNCERTAINTY BALANCERS - Even innovators who claim to love risk balance the uncertainty they face by incorporating more-certain things into their lives.
- Uncertainty Balancers - "in the form of habits, routines, rituals, objects, humor and relationships, served to counteract, or balance the unknown they faced."
- "many of those who claimed to love uncertainty had also gone to surprising lengths to create a great deal of certainty in other parts of their lives."
- Relationships may be the most powerful uncertainty balancers.
- DON’T FORCE MACHINERY - The anxiety created by uncertainty can trap us into prematurely settling for suboptimal certainty. SOMETIMES THE BEST PREPARATION IS TO BE PATIENT. We must learn to entertain the unknown long enough to LET A BETTER FUTURE EMERGE.
- Alert and Proactive Patience - Curiosity
- Follow your Curiosity - Elizabeth Gilbert
- "Curiosity is accessible to everyone. Passion can seem intimidatingly out of reach sometimes, a distant tower of flame accessible only to geniuses and to those who are specially touched by God. But curiosity is a milder, quieter, more welcoming, and more democratic entity."
- "Even when we intuit that our decision is right, waiting till the RIGHT MOMENT takes LEADERSHIP AND PRACTICE."
- “Patience is a virtue”
- How do you know whether you should take action or be patient?
- The moment to take action is when "the head and heart came together" - The Hieatts
- Additional Prime Tools
- Personal Real Options - Research on hybrid entrepreneurs reveals that risking it all is often counterproductive. Helping a portfolio of both certain and uncertain projects help reduce anxiety while increasing your chances of success.
- Dumbo Feathers - People, places, and things can be your biggest helps or greatest hinderances. How do you find the "Dumbo feathers" that will help you fly to your dreams and avoid the quest destroyers that will pull you down?
- Know Your Risks - Most people are attracted to some types of risks and are averse to others. Knowing your risk profile helps you fortify where you feel weak and make the most of your affinities.
- Runway and Landing Strips - Runways and landing strips are the money and time to get your ideas off the ground and the networks that give you new opportunities.
- Reimagining Resources - Too often we let constraints limit our imagination, but there are ways to reimagine resources to transform overlooked abundance and use constraints as fuel for creativity.
Do Tools (Top 3)
"When we meet uncertainty from this expanded sense of possibility, DOING becomes AN IMAGINATIVE, GENERATIVE, DISCOVERY-DRIVEN ACTION."
- ACTIVATE AND UNLOCK - Despite the human obsession with managing and reducing risk, some things are better when you stop trying to control them. Look for ways to activate and unlock the essence of the uncertainty you are facing.
- Manage and Control - vs - Activate and Unlock
- "Endogenous uncertainty" - "the idea that new opportunities can actually be created by choosing to increase uncertainty, rather than the more common approach of reducing uncertainty." — Harvard Business School
- "In other words, the possibilities are already latent in the thing you are unlocking "like the seed of a tree, it has the whole of a tree... Relieving and releasing (what is already there) is the work I find far more exciting than doing my smudge and saying, 'that's mine". - Adrien Gardere
- VALUES VERSUS GOALS - How can you set yourself up so you never fail? When you navigate uncertainty based on your values instead of mercurial goals, you free yourself from the anxiety-producing outcomes over which you have no control and lay the groundwork for success, no matter what happens.
- "The problem starts with the beautiful but dangerous idea that anyone can achieve anything."
- "If you really believe in a world where you believe you can do anything, and you only have done a bit, my goodness, how crushed you will feel. The possibilities for humiliation are so much greater now... Leading a good life isn't enough; you need to be extraordinary,.. This is the kind of torture we have imposed on ourselves."
- "How have we made a life where the statistical odds... the 99% surety that you will lead an ordinary life.. has come to seem like a humiliation and the wrong sort of life? This is setting yourself up for disaster." - Alain de Botton - Philosopher
- He argues that focusing on goals only creates an illusion of control - while also increasing anxiety and the likelihood that we make trade-offs about the things we care most about. - David Heinemeier Hansson - creator of Ruby on Rails and Basecamp
- "We felt discouraged by seeing teenagers trapped by the dogma of passion - the stressful idea that if they could find the one thing they cared about and sacrificed everything to it, they would be the next Steve Jobs. We could see the ANXIETY it created and the FALLACY it imposed. We were searching for people doing work in earnest ways (wholehearted, authentic, diligent, passionate and mindful).
- "Although we may live in a world that sings the praises of a winner-take-all mindset, the heroes in our stories, and in our lives, don't take it all for themselves. THAT'S WHAT VILLAINS DO. Instead, heroes create opportunities not just for themselves but for others as well."
- LEARNING IN FOG - Navigating uncertainty can feel like trying to find your way through a dense fog. Using the right learning strategies helps blow away the fog and guide you to new opportunities.
- "But as you start to get more successful, you are in the front. There are no more lights in front, and you have no clue what to do."
- How do you navigate the fog? - Adopt a set of learning techniques - Fast Cycles, Simple Rules, Switching Approaches - “to learn as quickly as possible so that you don’t spend all your time hesitating on a hilltop or bumbling blindly through the gloom.”
- Fast Cycles - Incubate and test (don’t overthink)
- Simple Rules - "They found that more successful entrepreneurs used past experience to develop rules about what to focus on and how to do it”.
- Switching Approaches - "Recognize there are different learning strategies and that you may need to change yours to match the problem you face."
- Additional Do Tools
- 10,000 Shots - The notion of unqualified genius is fiction. Fields like acting, photography, and entrepreneurship show us that before we can succeed, we must try, try, try again.
- Cognitive Flexibility - Successful innovators don't persists at all costs. Instead, they adapt their worldview as they go, adopting an "attitude of wisdom" that allows them to become cognitively flexible and ready for changing circumstances.
- Bricolage Innovators don't wait for the perfect circumstance to take action. Instead they use whatever they have at hand to get started, which, in a twist of fate, often helps them discover yet more possibilities.
- Small Steps - We don't have to do everything at once to succeed. Most victories are the culmination of a slow climb up the mountain, one step and one experiment at a time.
- Pivot - When dealing with uncertainty, it is inevitable that you will need to change direction. Give yourself permission to adapt.
Sustain Tools (Top 3)
Sustain tools help to cultivate a healthy eco-system to “nourish and comfort you through the downsides of uncertainty”. With opportunities comes “powerful obstacles to navigating uncertainty well” like regret, anxiety, grief, self-doubt, embarrassment.
"Sustain is about not giving up on our dreams, our values, or ourselves."
- SUSTAIN TOOLS (3 Categories)
- EMOTIONAL HYGIENE: Consistent and skillful care of our emotional selves. Practice being your own doula who assists you in delivering the possibilities you are striving for.
- RIDING THE WAVES - Emotions come in waves, in highs and lows. Know that cycle is natural - everyone feels it. If you're at a low point, better times are coming!
- "Creatives, artists, and designers talk about the thrill of starting a new project, followed by the dark forest with cycles of inspiration and doubt, of grueling work and flow, until they emerge victorious near the completion of the project.
- "Mentors, life coaches, therapists, partners, and friends can all act as these special assistants, helping TO GUIDE YOU to your best outcomes."
- Additional Sustain Tools - Emotional Hygiene Tools
- Hope is Active - Hope isn't something that happens. it is an active choice to believe our dreams into being, even if we feel they are on shaky ground.
- Connection and Community - We are sustained by enriching communities. Surround yourself with others who understand your situation or can build your optimism. Connect with people you can learn from.
- Comforts - Our senses bypass the thinking brain and bring immediate comfort. Use them to create a HAVEN at home or at work and to ground you when you are distressed.
- REALITY CHECK: Using the reasoning mind to unpack the real situation. Practice being your own wise counselor, finding solutions or options that are realistic and valuing the lessons you can learn.
- LEARNED OPTIMISM - Decatastrophize setbacks by seeing them as temporary, isolated to circumstances, and not entirely your fault. Celebrate your victories and dispute the negative beliefs to find more energy to try again.
- "optimism and pessimism are actually learned explanatory styles that we develop over time, not inherent orientations that are a fixed part of our personality… people who develop a more optimistic, explanatory style resisted "learned helplessness" - that is, when we no longer try to change an adverse situation because we believe we are powerless - and found ways to change their situation for the better." - Martin Seligman - Pioneer of Positive Psychology
- Optimist tended to view problems as temporary, limited to specific situations, and having several causes for what happened (so they could avoid blaming themselves)
- Pessimist "view problems as permanent, impacting every aspect of their lives, so they blame themselves exclusively for what went wrong… As a result, pessimist tend to sink into rumination and negative self-talk, increasing the feeling of dejection and passivity."
- Additional Sustain - Reality Check Tools
- Embrace Being Human - Surrender to the reality that humans have instinctual fear - it has helped our species survive. Then move into a more meaningful attitude toward anxiety and uncertainty.
- Frustration Management - It's OK to let yourself feel frustrated by a setback for a period of time but then use reframing techniques to defang the setback. After all, setbacks are an inevitable part of uncertainty and possibility.
- Sorting Knowns and Unknowns - Identifying what you know and what you don't know can decrease your anxiety and provide some knowns to fill in the gaps. You might be able to use analogies to make sense of the unknowns to give you some firmer footing.
- Alternatives and Probabilities - Too often we think in binary terms, obsessing about success versus failure. In reality, life has many more possible outcomes than we can imagine. Seeing the broader set of options and thinking in terms of probabilities can help decrease your stress about the unknown.
- Creative Competition - Don't lose sight of the benefit of competition; It gets you doing your best work. What can your learn from competitors? How can they inspire you? Creative collaboration is even better, and it's a way out of the competition dilemma.
- Worst-Case Scenario - Obsessing about the worst-case scenarios can be disabling. Sometimes unpacking the worst-case scenarios and walking it through to its final implications can reveal that the "monster under the bed" isn't quite as terrible as we feared.
- The Optimization Myth - There isn't one best way to do anything. Don't get obsessed with what you imagine the optimal outcome to be. You might miss out on the way it was really meant to happen.
- MAGIC: The leaps of insights, connection, and serendipity that change and inspire us. We don't control the magic, but we can make more room for it. Paying attention like an artist increases our chances for serendipity and inspiration.
- "The Artists (poet, painter, film director, chef) - who PAYS ATTENTION, learns to be TRANSFIGURED by the ordinary materials of life, and then from that place CREATES BEAUTY, MEANING, or even REVELATIONS OF FLAVOR that thrill and inspire us."
- HELPING OTHERS - Empathy, compassion, and service all reward the giver and the receiver. When people are kind during times of struggle or stress, they experience less distress and more hope themselves.
- "Helping others can also relieve the anxiety you feel, replacing SELF-DOUBTING STANCE with one of LEADERSHIP."
- "The beauty of the organization, aside from side-stepping the adult-save-the-kid mentality, is that by mentoring other girls in STEM, the girls doing the mentoring experience reduced self-consciousness, self-absorption, and anxiety about their future. BY FOCUSING THEIR ENERGY ON HELPING OTHERS, THEY SUSTAIN THEMSELVES." - Ricardo de Santos - Founder of Scientella - STEM school
- "The question I have found myself asking again and again is, What can we do in our lives, through the decisions we make, choices we make, about how to tip the scales in the world away from fear and toward love? How can we do that through how we treat other people, through what we say, through the issues we choose to speak up on in the public square, through the jobs we take and the purpose we seek to fulfill?" - Dr. Vivek Murthy - Former US Surgeon General
- Additional Sustain - Magic Tools
- Memento Mori - From the Latin, "Remember, you must die," this practice is an ancient form of meditation on the certainty that your time is limited, which can help us infuse these days you have with more vibrant living and joy.
- Picaresque - Few people live the life they planned. Go along for the ride of your life. Don't take thinks too seriously or personally. Cultivate your garden and discover the magic that is already there.
- As If - Living as if something was already true is a technique philosophers and political activist use to invoke action and change. Living as if possibilities exist can increase the chances that they will come to be and help us endure while we wait for them.
- Techs You Live By - If technology is "any phenomenon put to use," what technologies are you using and why? Being intentional about adding philosophy, art, poetry, music, and such "high techs" creates more room for magic.
Reflection & Response: Envisioning Process
- Envision: The Desired Future - Reframe Tools
- Embrace: The Current Reality - Reality Check (Sustain)
- Evaluate: The Path Forward - Do tools
- Enroll: The Beautiful Future - Magic (Sustain)
- Establish: The Beautiful Life - Fait Sur Measure (Prime)