by Robyn Bolton | Sep 9, 2025 | Innovation, Leading Through Uncertainty
Last night, I lied to a room full of MBA students. I showed them the Design Squiggle, and explained that innovation starts with (what feels like) chaos and ends with certainty.
The chaos part? Absolutely true.
The certainty part? A complete lie.
Nothing is ever Certain (including death and taxes)
Last week I wrote about the different between risk and uncertainty. Uncertainty occurs when we cannot predict what will happen when acting or not acting. It can also be broken down into Unknown uncertainty (resolved with more data) and Unknowable uncertainty (which persists despite more data).
But no matter how we slice, dice, and define uncertainty, it never goes away.
It may be higher or lower at different times,
More importantly, it changes focus.
4 Dimensions of Uncertainty
Something new that creates value (i.e. an innovation) is multi-faceted and dynamic. Treating uncertainty as a single “thing” therefore clouds our understanding and ability to find and addresses root causes.
That’s why we need to look at different dimensions of uncertainty.
Thankfully, the ivory tower gives us a starting point.
WHAT: Content uncertainty relates to the outcome or goal of the innovation process. To minimize it, we must address what we want to make, what we want the results to be, and what our goals are for the endeavor.
WHO: Participation uncertainty relates to the people, partners, and relationships active at various points in the process. It requires constant re-assessment of expertise and capabilities required and the people who need to be involved.
HOW: Procedure uncertainty focuses on the process, methods, and tools required to make progress. Again, it requires constant re-assessment of how we progress towards our goals.
WHERE: Time-space uncertainty focuses on the fact that the work may need to occur in different locations and on different timelines, requiring us to figure out when to start and where to work.
It’s tempting to think each of these are resolved in an orderly fashion, by clear decisions made at the start of a project, but when has a decision made on Day 1 ever held to launch day?
Uncertainty in Pharmaceutical Development
Let’s take the case of NatureComp, a mid-sized company pharmaceutical company and the uncertainties they navigated while working to replicate, develop, and commercialize a natural substance to target and treat heart disease.
- What molecule should the biochemists research?
- How should the molecule be produced?
- Who has the expertise and capability to synthetically poduce the selected molecule because NatureComp doesn’t have the experience required internally?
- Where to produce that meets the synthesization criteria and could produce cost-effectively at low volume?
- What target disease specifically should the molecule target so that initial clincial trials can be developed and run?
- Who will finance the initial trials and, hopefully, become a commercialization partner?
- Where would the final commercial entity exist (e.g. stay in NatureComp, move to partner, stand-alone startup) and the molecule produced?
And those are just the highlights.
It’s all a bit squiggly
The knotty, scribbly mess at the start of the Design Squiggle is true. The line at the end is a lie because uncertainty never goes away. Instead, we learn and adapt until it feels manageable.
Next week, you’ll learn how.
by Robyn Bolton | Sep 2, 2025 | Leading Through Uncertainty, Strategy
In September 2011, the English language officially died. That was the month that the Oxford English Dictionary, long regarded as the accepted authority on the English language published an update in which “literally” also meant figuratively. By 2016, every other major dictionary had followed suit.
The justification was simple: “literally” has been used to mean “figuratively” since 1769. Citing examples from Louisa May Alcott’s Little Women, Charles Dickens’ David Copperfield, Charlotte Bronte’s Jane Eyre, and F. Scott Fitzgerald’s The Great Gatsby, they claimed they were simply reflecting the evolution of a living language.
What utter twaddle.
Without a common understanding of a word’s meaning, we create our own definitions which lead to secret expectations, and eventually chaos.
And not just interpersonally. It can affect entire economies.
Maybe the state of the US economy is just a misunderstanding
Uncertainty.
We’re hearing and saying that word a lot lately. Whether it’s in reference to tariffs, interest rates, immigration, or customer spending, it’s hard to go a single day without “uncertainty” popping up somewhere in your life.
But are we really talking about “uncertainty?”
Uncertainty and Risk are not the same.
The notion of risk and uncertainty was first formally introduced into economics in 1921 when Frank Knight, one of the founders of the Chicago school of economics, published his dissertation Risk, Uncertainty and Profit. In the 114 since, economists and academics continued to enhance, refine, and debate his definitions and their implications.
Out here in the real world, most businesspeople use them as synonyms meaning “bad things to be avoided at all costs.”
But they’re not synonyms. They have distinct meanings, different paths to resolution, and dramatically different outcomes.
Risk can be measured and/or calculated.
Uncertainty cannot be measured or calculated
The impact of tariffs, interest rates, changes in visa availability, and customer spending can all be modeled and quantified.
So it’s NOT uncertainty that’s “paralyzing” employers. It’s risk!
Not so fast my friend.
Not all Uncertainties are the same
According to Knight, Uncertainty drives profit because it connects “with the exercise of judgment or the formation of those opinions as to the future course of events, which…actually guide most of our conduct.”
So while we can model, calculate, and measure tariffs, interest rates, and other market dynamics, the probability of each outcome is unknown. Thus, our response requires judgment.
Sometimes.
Because not all uncertainties are the same.
The Unknown (also known as “uncertainty based on ignorance”) exists when there is a “lack of information which would be necessary to make decisions with certain outcomes.”
The Unknowable (“uncertainty based on ambiguity”) exists when “an ongoing stream [of information] supports several different meanings at the same time.”
Put simply, if getting more data makes the answer obvious, we’re facing the Unknown and waiting, learning, or modeling different outcomes can move us closer to resolution. If more data isn’t helpful because it will continue to point to different, equally plausible, solutions, you’re facing the Unknowable.
So what (and why did you drag us through your literally/figuratively rant)?
If you want to get unstuck – whether it’s a project, a proposal, a team, or an entire business, you first need to be clear about what you’re facing.
If it’s a Risk, model it, measure it, make a decision, move forward.
If it’s an uncertainty, what kind is it?
If it’s Unknown, decide when to decide, ask questions, gather data, then, when the time comes, decide and move forward
If it’s Unknowable, decide how to decide then put your big kid pants on, have the honest and tough conversations, negotiate, make a decision, and move on.
I mean that literally.
by Robyn Bolton | Aug 4, 2025 | Leadership, Leading Through Uncertainty, Stories & Examples, Strategy
The best business advice can destroy your business. Especially when you follow it perfectly.
Just ask Johnny Cash.
After bursting onto the scene in the mid-1950s with “Folsom Prison Blues”, Cash enjoyed twenty years of tremendous success. By the 1970s, his authentic, minimalist approach had fallen out of favor.
Eager to sell records, he pivoted to songs backed by lush string arrangements, then to “country pop” to attract mainstream audiences and feed the relentless appetite of 900 radio stations programming country pop full-time.
By late 1992, Johnny Cash’s career was roadkill. Country radio had stopped playing his records, and Columbia Records, his home for 25 years, had shown him the door. At 60, he was marooned in faded casinos, playing to crowds preferring slot machines to songs.
Then he took the stage at Madison Square Garden for Bob Dylan’s 30th anniversary concert.
In the audience sat Rick Rubin, co-founder of Def Jam Recordings and uber producer behind Public Enemy, Run-DMC, and Slayer, amongst others. He watched in awe as Cash performed, seeing not a relic but raw power diluted by smart decisions.
The Stare-Down that Saved a Career
Four months later, Rubin attended Cash’s concert at The Rhythm Café in Santa Anna, California. According to Cash’s son, “When they sat down at the table, they said: ‘Hello.’ But then my dad and Rick just sat there and stared at each other for about two minutes without saying anything, as if they were sizing each other up.”
Eventually, Cash broke the silence, “What’re you gonna do with me that nobody else has done to sell records for me?”
What happened next resurrected his career.
Rubin didn’t promise record sales. He promised something more valuable: creative control and a return to Cash’s roots.
Ten years later, Cash had a Grammy, his first gold record in thirty years, and CMA Single of the Year for his cover of Nine Inch Nails’ “Hurt,” and millions in record sales.
When Smart Decisions Become Fatal
Executives do exactly what Cash did. You respond to market signals. You pivot your offering when customer preferences shift and invest in emerging technologies.
All logical. All defensible to your board. All potentially fatal.
Because you risk losing what made you unique and valuable. Just as Cash lost his minimalist authenticity and became a casualty of his effort to stay relevant, your business risks losing sight of its purpose and unique value proposition.
Three Beliefs at the Core of a Comeback
So how do you avoid Cash’s initial mistake while replicating his comeback? The difference lies in three beliefs that determine whether you’ll have the creative courage to double down on what makes you valuable instead of diluting it.
- Creative confidence: The belief we can think and act creatively in this moment.
- Perceived value of creativity: Our perceived value of thinking and acting in new ways.
- Creative risk-taking: The willingness to take the risks necessary for active change.
Cash wanted to sell records, and he:
- Believed that he was capable of creativity and change.
- Saw the financial and reputational value of change
- Was willing to partner with a producer who refused to guarantee record sales but promised creative control and a return to his roots.
Your Answers Determine Your Outcome
Like Cash, what you, your team, and your organization believe determines how you respond to change:
- Do I/we believe we can creatively solve this specific challenge we’re facing right now?
- Is finding a genuinely new approach to this situation worth the effort versus sticking with proven methods?
- Am I/we willing to accept the risks of pursuing a creative solution to our current challenge?”
Where there are “no’s,” there is resistance, even refusal, to change. Acknowledge it. Address it. Do the hard work of turning the No into a Yes because it’s the only way change will happen.
The Comeback Question
Cash proved that authentic change—not frantic pivoting—resurrects careers and disrupts industries. His partnership with Rubin succeeded because he answered “yes” to all three creative beliefs when it mattered most. Where are your “no’s” blocking your comeback?
by Robyn Bolton | Jul 23, 2025 | Leadership, Leading Through Uncertainty, Stories & Examples
What does a lightning strike in a Spanish forest have to do with your next leadership meeting? More than you think.
On June 14, 2014, lightning struck a forest on Spain’s northeast coast, only 60 miles from Barcelona. Within hours, flames 16 to 33 feet high raced out of control toward populated areas, threatening 27,000 acres of forest, an area larger than the city of Boston.
Everything – data, instincts, decades of firefighting doctrine – prioritized saving the entire forest and protecting the coastal towns.
Instead, the fire commanders chose to deliberately let 2,057 acres, roughly the size of Manhattan’s Central Park, burn.
The result? They saved the other 25,000 acres (an area the size of San Francisco), protected the coastal communities, and created a natural firebreak that would protect the region for decades. By accepting some losses, they prevented catastrophic ones.
The Fear Trap That’s Strangling Your Business
The Tivissa fire’s triumph happened because firefighters found the courage to escape what researchers call the “fear trap” – the tendency to focus exclusively on defending against known, measurable risks.
Despite research proving that defending against predictable, measurable risks through defensive strategies consistently fails in uncertain and dynamic scenarios, firefighter “best practices” continue to advocate this approach.
Sound familiar? It should. Most executives today are trapped in exactly this pattern.
We’re in the fire right now. Financial markets are yo-yoing, AI threatens to disrupt everything, and consumer behaviors are shifting.
Most executives are falling into the Fear Trap by doubling down on protecting their existing business and pouring resources into defending against predictable risks. Yet the real threats, the ones you can’t measure or model, continue to pound the business.
While you’re protecting last quarter’s wins, tomorrow’s disruption is spreading unchecked.
Four Principles for Creative Decision-Making Under Fire
The decision to cede certain areas wasn’t hasty but based on four principles enabling leaders in any situation to successfully navigate uncertainty.
PRINCIPLE 1: A Predictable Situation is a Safe Situation. Stop trying to control the uncontrollable. Standard procedures work in predictable situations but fail in unprecedented challenges.
Put it in Practice: Instead of creating endless contingency plans, build flexibility and agility into operations and decision-making.
PRINCIPLE 2: Build Credibility Through Realistic Expectations. Reducing uncertainty requires realism about what can be achieved. Fire commanders mapped out precisely which areas around Tivissa would burn and which would be saved, then communicated these hard truths and the considered trade-offs to officials and communities before implementing their strategy, building trust and preventing panic as the selected areas burned.
Put it in practice: Stop promising to protect everything and set realistic expectations about what you can control. Then communicate priorities, expectations, and trade-offs frequently, transparently, and clearly with all key stakeholders.
PRINCIPLE 3: Include the future in your definition of success: Traditional firefighting protects immediate assets at risk. The Tivissa firefighters expanded this to include future resilience, recognizing that saving everything today could jeopardize the region tomorrow.
Put it in practice: Be transparent about how you define the Common Good in your organization, then reinforce it by making hard choices about where to compete and where to retreat. The goal isn’t to avoid all losses – it’s to maximize overall organizational health.
PRINCIPLE 4: Use uncertainty to build for tomorrow: Firefighters didn’t just accept that 2,057 acres would burn – they strategically chose which acres to let burn to create maximum future advantage, protecting the region for generations.
Put it in practice: Evaluate every response to uncertainty on whether it better positions you for future challenges. Leverage the disruption to build capabilities, market positions, and organizational structures that strengthen you for future uncertainty.
Your Next Move
When the wind shifted and the fire exploded, firefighters had to choose between defending everything (and likely losing it all) or accepting strategic losses to ensure overall wins.
You’re facing the same choice right now.
Like the firefighters, your breakthrough might come not from fighting harder against uncertainty, but from learning to work with it strategically.
What are you willing to let burn to save what matters most?
