Strategy #2: Calculated Defiance: How to Play by the Small Rules So You Can Break the Big Ones
Don't Leap Without a Parachute: Why Strategic Conformity Wins the Side Hustle Game
Digging in with Joan Fernandez” is a bi-weekly newsletter with ideas for you on shattering limits to reaching your true potential, told through bits from the life of Jo van Gogh (the woman that would not allow Van Gogh to die twice). Please sign up here.
In the last newsletter, I announced that I am writing Book #2: a non-fiction book about the twelve marketing strategies I discovered while researching my biographical novel, Saving Vincent: A Novel of Jo van Gogh. You can read Strategy #1 from the last issue here.
Are you more of an “ask for forgiveness” rule-breaker?
Or more of a “get permission first” rule-abiding kind of person?
“It depends,” you might respond.
Exactly.
When we think of entrepreneurs who change the world, we often picture the lone wolf—a reckless rebel running wild outside the pack, completely detached from society, howling at the moon, and burning down the status quo. But lasting brilliance doesn't require you to starve in the wilderness.
That’s the essence of Calculated Defiance, the second entrepreneurial strategy I gleaned from studying Jo van Gogh’s work in building a world-class legacy for Vincent van Gogh after his death. It’s the art of playing by the small rules so you have the room to break the big ones.
It’s not about being a rogue outsider for the sake of it; it's about strategically choosing your own territory.
Jo van Gogh’s Quiet Rebel Era
For a heartbroken Jo, this pivotal moment came while in the depths of grief at her husband’s passing in 1891. Suddenly widowed at the age of 28 with a 1-year-old baby. In Paris—far from her childhood Dutch home—with no income, it was a foregone conclusion that she would return to her father’s house in Amsterdam.
Instead, she took a 180-degree turn. She refused her father’s instructions; and chose to move back to the Netherlands to open a boarding house, a socially acceptable occupation for a widow at that time.
Choosing her own roof over her father’s roof was the first of many selective rules Jo would break. This is the heart of Calculated Defiance: it isn't about being reckless, but rather choosing precisely which rules to follow and which to bend.
She stayed within the “acceptable” lane of running a boarding house to secure a steady cash flow and a home for her son—a disobedient choice wrapped in just enough propriety to keep her critics at arm’s length.
It’s here that she also had her inheritance of paintings and drawings shipped and stored in the attic of her boarding house. Keeping the collection together was her first smart move, but it also attracted the first of many attacks. Her family and husband’s friends gave her intense pressure to either liquidate it or hand it over.
But because she had secured her independence (and Dutch law protected her property rights as a widow), she owned the assets completely. When the art world ultimately realized the value of the collection, they would have to come to her. She held all the cards.
For today’s entrepreneur, the idea of calculated, selective defiance of the status quo destroys the myth that you have to leap off a cliff without a parachute. It shows that securing your baseline—whether that’s keeping a day job while building a side hustle, or offering a standard, predictable service to fund your truly innovative project—can be a smart way to protect your long-term vision.
Case Study: How Brownie Wise Built a Living Room Empire
Here’s an example of another entrepreneur who demonstrated the mindset of Calculated Defiance.
In the 1950s, women were heavily restricted by post-war domestic expectations. The pioneering businesswoman Brownie Wise used those exact restrictions as her staging ground.
The Safety of Convention: Wise operated entirely within the acceptable social boundary of the 1950s: suburban housewives hosting living-room gatherings. To the outside world, it looked like harmless neighborhood socializing.
The Strategic Defiance: Tupperware was failing on hardware store shelves because people didn’t understand how the airtight seal worked. Wise defied the entire traditional retail distribution model. She pulled the product out of stores and engineered the “Tupperware Party,” doing in-home demonstrations of the product. She built a massive, independent, matriarchal sales network that has since given millions of women and men their own income and autonomy.
The Leverage: Wise made Tupperware so wildly successful that the company’s founder, Earl Tupper, named her Vice President of Marketing in which she ran the entire marketing empire. She took a plastic bowl and turned it into a cultural and financial phenomenon from a living room couch. Ultimately, her home party model inspired hundreds of others and serves the basis for the “side hustle” direct sales businesses that exist today.
Notice how the lesson from both Jo van Gogh and Brownie Wise isn’t simply to “go off and be independent.” Instead, Calculated Defiance uses the safety of convention to fund the risk of autonomy.
Strategy #2:
Defiance buys your independence. Strategy turns it into leverage.
Jo showed you don’t have to be a reckless rebel to change the world. Independence didn’t draw the crowd—but it gave her the absolute authority to execute the brilliant marketing strategies that did.
Next up are her first strategies toward getting started, or market penetration, but in the meantime. . .
Ready to break a rule?
I am!
Book News and Notes
(Captions are left to right)
I gave my talk, “Jo van Gogh-Bonger: The Woman Who Would Not Let Van Gogh Die Twice,” to a terrific 100-person audience in Wanamaker Hall at my treasured alma mater Principia College.
Great night: Signing books at the Principia Summer Session craft bazaar while meeting up with new and old friends.
#BestGardenParty Ever: I hung out with my 1-year-old granddaughter Rebel (and 3-yo brother Bodie who is SO FAST he’s a blur in this photo) in KC last weekend.
Delighted that Saving Vincent has been awarded Finalist (in Historical Fiction) in the 2026 International Book Awards.
Don’t Miss these SUMMER READING RECS!
From Our Desks to Yours: 5 Extraordinary Historical Novels We Love
If your bookshelf is already filled with sweeping tales of resilience, hidden legacy, and female autonomy, my sister authors and I have a treat for you. We’ve mapped our books directly to some of the most beloved historical bestsellers on the market today so you can find your next perfect read. . .plus have created a giveaway to give you a chance to win them all!
Daughter of the King (by Kerry Chaput) is like The Book of Longings by Sue Monk Kidd for its powerful exploration of a woman fighting for spiritual autonomy against rigid religious tyranny, forcing a brave departure from everything she knows to protect her truth.
Saving Vincent (by yours truly) is like The Personal Librarian by Marie Benedict and Victoria Christopher Murray because it centers on a woman’s hidden strategy in a male-dominated world, revealing how her brilliance shaped a global legacy we now take for granted.
Under Two Flags (by Janis Daly) is like The Alice Network by Kate Quinn, dropping a fierce, artistically minded young woman into the crucible of WWI and capturing the immense courage required to survive behind enemy lines.
The Irish Girl (by Ashley Sweeney) is like Brooklyn by Colm Tóibín for its intimate look at the heartache and isolation of a solo female immigrant, contrasting a deep longing for home with the gritty reality of carving out a new life in America.
Solitary Walker (by N.J. (Nancy) Mastro) is like Hamnet by Maggie O’Farrell because of its exquisite emotional depth, exploring the resilience and inner world of a brilliant woman whose independent spirit is often eclipsed by a famous historical legacy.
ENTER NOW - GIVEAWAY ENDS JUNE 30
ENTER NOW FOR SUMMER READS!
This giveaway ends on June 29!
Great post, Joan! Di interesting about the Tupperware story. I still have some of my mom’s and it still works so well! Congratulations on all your success!
Great advice - and I love that you spoke so successfully at your alma mater. I think that means "nurturing mother," and that's what your marketing suggestions will be for many, I'm sure...