Stout Insights: Harness The Magic Of Midlife Mojo To Fast Track Your Future

Stout Insights: Harness The Magic Of Midlife Mojo To Fast Track Your Future

Deep dives from leaders in the know.

Women “Of A Certain Age” Are Taking Charge & Powering Change

Kick-start your next chapter with #StoutTakeaways from the SXSW NextLife panel of forward-thinking female entrepreneurs leaning in to shatter myths about midlife.


Jeannie Ralston, Ricki Fairley, Tammy Shaklee and Lyndie Benson talk out ideas preparing for the SXSW NextLife panel.

Is This The Real Life?

In Jeanne Ray’s 2013 novel, Calling Invisible Women, a rare drug interaction causes the protagonist, Clover, to become invisible. What she discovers is something many women of a certain age suspect deep down — those around her had long ago stopped seeing her. It took several weeks for anyone to realize that while they could hear her voice, smell her perfume and recognize her clothing — they couldn’t actually see her. This gradual loss of visibility and self is no fantasy for many women hitting midlife in the real world.

There are two great times in your life to build a business: in your 20s when you have nothing to lose, and in your 50s when you have nothing to prove.
– Jeannie Ralston, Founder & Editor of NextTribe

Flipping Fade The Bird

Like Clover, who eventually found her moxie and took on the drug company, this powerhouse panel of forward-thinking women who took the stage at SXSW this past March refused to accept becoming invisible. They leaned in, and embraced one of the best benefits of making it to midlife — you simply run out of f***s to give. Thus emboldened, Jeannie Ralston, Ricki Fairley, Tammy Shaklee and Lyndie Benson took everything that led to being fifty — and propelled that experience into creating successful businesses.

These #Stout entrepreneurs packed a punch at SXSW with honest, detailed accounts of their bold, brave and determined journeys to reinvention.

No Imposters Here

Not that it was easy for any of them. With refreshingly painful honesty, they detailed struggles with imposter syndrome, fear — of failure, of running out of money, or what people might think — and the inevitable mistakes that come with making bold moves. At SXSW, they each shared three top tips to help other women looking to take charge of their own futures and redefine what midlife can be.

No is never the answer. It’s always ‘how’.
– Ricki Fairley, Founder of Dove Marketing

Female Entrepreneurs Step Up

More and more women like Ralston, Shaklee, Fairley and Benson are stepping up, and the future of older female entrepreneurs looks powerfully bright. 2019 has been a record year for VC investment in female-founded businesses, and the 55-64 year old age group holds the highest rate of entrepreneurship in the US.

On the fence about jumping in? Shaklee’s final suggestion was as positive and direct as she is: “Just go for it. Don’t over-research — just hang your shingle, start your biz, and you’ll work out the kinks.” Whether you’re at midlife or at another potential pivot point, check out our takeaways below for more on how to take charge and write your own future!


Stout Insights
  Top Tips For How To Work Midlife Mojo  

Jeannie Ralston

Jeannie Ralston, Founder/Editor, NextTribe
(1)  Nurture and revisit your network
(2)  Don’t stop yourself with self-doubt
(3)  Make sure you have a cheerleading/support group


Tammy Shaklee

Tammy Shaklee, Founder of H4M Gay & Lesbian Matchmaking
(1) Take time to write a business plan
(2) Get educated in what you don’t know
(3) Hire out your weaknesses

Ricki Fairley

Ricki Fairley

Ricki Fairley, Founder/President, DOVE Marketing
(1)  Figure out the 3 words you want people to say about you
(2)  Don’t burn bridges
(3)  Growth can come from upheaval


Lyndie Benson

Lyndie Benson, CEO/Founder, Bleusalt clothing
(1) Know your value
(2) Know your purpose
(3) Expect and be willing to keep overcoming challenges

Want more?

Watch the full SXSW session here. And for help turning your fifty-something lack of f***s to give into the power to write your own future — check out these great articles on entrepreneurship from Stout Magazine.