What Martha Stewart can teach us about reinvention and career pivots.
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I’m grateful to be back and share what’s next.
I’ve been through somewhat of my own pivot and reinvention this year, one that has also led me to a fascination in the inevitable period every entrepreneur faces in their journey: the season of change, reviewing and rebuilding.
So, to kick off this new season of The Ask newsletter it was only apt to discuss a veteran in career pivots and reinvention: Martha Stewart.
Her name has recently returned to the public eye in force following Netflix’s honest documentary on her life and career, Martha.
Martha Stewart: A case study in personal reinvention and career pivots
If you’ve ever wondered what’s required to reinvent yourself —not just a simple rebrand, but a bold, unapologetic pivot that asks the world to take a fresh eyed look at you… Martha Stewart can tell you a thing or two about that.
A self-proclaimed perfectionist, Martha built her brand around an image of meticulous perfection. But she faced her greatest test when allegations of securities fraud led to her public imprisonment, upturning an image she had spent literal decades cultivating.
Whether you believe her proclaimed innocence or not, one thing is clear: the absolute worst possible outcome for a woman like Martha happened in that moment of sentencing.
And then after she returned from prison, against all odds, she made a comeback.
If a woman previously upheld as the nation’s sweetheart can do that for her career, you my friend can make a change in your business or personal brand.
Reinvention is both an art and a necessity in a world of change.
For seasoned entrepreneurs facing their next pivot, here’s some lessons Martha’s journey can inspire in your on reinvention and career shifting.
Be guided by your future, not your past
Coming back from the fall of public grace was not Martha’s first rodeo with reinvention. Her entire life arc is shaped by following a curiosity for new horizons; always choosing herself as ready for the next opportunity.
Martha’s determination and commitment to spotting opportunities created a string of shifts in her professional life: from schoolgirl to professional model, university student to wife and mother, to landing a job as one of Wall Street’s first stockbrokers. She spotted a renovation opportunity for their home in Westport, where she began her empire building, one garden landscape and catering project after the other.
Homemaking projects might have began at home, but Martha soon spotted the gap in the market for her unique taste — at big events, then for magazines, books, television…. brick by brick building a billion dollar media empire.
The lesson? Allow your authentic curiosity, dreams and passion to guide you and to open doors you may not previously have imagined opening for you. Martha rested on the power authenticity, uniqueness and hard work and stayed true to her own vision.
Master branding (and rebranding) yourself
Martha’s brand has been through it all, from being considered the image of perfection, her face on the cover of brand deals and media. She was the original influence and built her fortune on the art of branding.
Her business empire — running a publicly traded company tied to her name —therefore relied on a positive public sentiment. So when she was accused of financial fraud, this all came crashing down.
It was only later at the Comedy Central roast of Justin Bieber that her public image rose like a phoenix out of the ashes — thanks to her witty comebacks and cultural references about her fellow A list celebrities, Martha was back, with a bite. Her PR team surely got a raise for this one.
It was only *because* of her time in prison and experiences falling out of favour that this new version of Martha could emerge at this time.
She once said, “When you’re through changing, you’re through.” That’s worth remembering.
The lesson? Know that you are always evolving. A pivot doesn’t mean leaving your old self behind —it means shaping it in a way that’s true to the new version of you, the one who has this new imagination, information and vision for what’s possible for you next.
If you’ve hit a roadblock, or experienced a setback, know that so often these moments are often the opening for something bigger.
Ignore the naysayers
From the beginning, Martha was unyielding in her vision. Her media empire she envisioned as a “solar system” with herself at the centre—a bold claim so many would shy firmly away from.
Critics called her a perfectionist, a control freak. The audacity of a woman to have such bold ambition deterred many.
But Martha didn’t bend. She created an empire around her own determination…. never waiting on permission or the green light of others.
Self-empowerment and Uniqueness are two of the cornerstones of The Ask values and philosophy so I cannot help admire the extent to which Martha owned these values — albeit ruffling some feathers and multiple missteps along the way I realise!
The lesson? Clarity around your values and faith in a brighter future will always ground you through your next pivot. When you have an unwavering conviction in what you’re building, and why, criticism feels less daunting. And remember: a pivot is so rarely an escape from your original vision. Its often the courageous next bold move for your vision.
For those at a crossroads, Martha’s story is proof that a pivot, when done right, can be one of the most powerful moves of your career.
So, like her or love her, her cannot take away the spirit of Martha Stewart.
Trust the process of your reinvention, missteps, failures and all. Embrace your intuition and inner curiosities, try, experiment with ideas and projects you feel called towards and keep standing tall in your vision, whatever shape it takes next.
And if you’d like support with your own pivot or your next bold move, here’s some ways we can connect:
For Londoner’s join me at this in person even in collab with Pivot Club, from Women On Our Way - grab tickets and hope to see you there on 3rd December
Download a 3700 word guide I’ve written for you on trusting your gut that something might be off in your business, and figuring out the next right step
Check out my 1-1 programme High Expectations for seasoned entrepreneurs ready for their next phase in business.
What a fantastic read!! We could all learn a lot from Martha S for sure! Your advice at the end is spot on. For me, I’m definitely at a pivot point with so many possible directions. Sometimes it’s hard to see the wood for the trees. But standing in your power, being clear on your values and trusting that those around you will support you as you test, iterate and evolve is such great advice! Being bold too💪 Do you think the same advice you share applies to running a community?