4 Female Entrepreneurs Share Their Biggest Career Learnings

Success isn’t always straight-forward

You’d be hard-pressed to find a CEO or company founder who hasn’t made a mistake (or three…) on their trajectory to the top. The road to success is often littered with learnings, and many entrepreneurs cite the errors they’ve made in the past as the most formative lessons of their careers.  

Here, we round up five female bosses who have overcome adversity and gone on to create some of today’s most successful businesses.

Reshma Saujani, Founder, Girls Who Code

After realising her innate need to be “perfect” all the time was holding her back, Reshma Saujani forged a new career path as the CEO of Girls Who Code, a global business encouraging women and girls to enter the tech industry by teaching them to code.

“The desire to be perfect held me back,” Saujanin says of her early career. “Playing it safe meant that my passion – organising and fighting for women and girls – was my side hustle for way too long.”

These days, instead of being perfect, she encourages women to be brave.

“Once we realise our mistakes won’t kill us, and that perfection is getting us nowhere, there’s nothing that can stop us.” Amen!

Sam White, CEO, Stella Insurance

Stella Insurance founder, Sam White is no stranger to adversity. As the daughter of a dysfunctional alcoholic, she made a conscious decision at a young age to create a different kind of life for herself. 

“It manifested a deep desire to prove that I was as good as anyone else,” says White, who launched her first business at the tender age of 24. “My motto became: ‘You think I’m lesser in some way? Prepare to be surprised.’”

White is now the owner of a portfolio of businesses in the UK including Action 365, Pukka Insure and Freedom Brokers, and recently launched Stella, a car insurance brand catering to Australian women. 

“When it came to work, I quickly realised that the conventional path wouldn’t suit me,” White says of her success. “I rebuffed conformity and set up my first insurance company, acutely aware that it was traditionally considered a male-dominated, almost-sterile industry. The irony wasn’t lost on me.”

Sam White
Sam White, CEO, Stella Insurance

Arianna Huffington, CEO, Thrive Global

When Arianna Huffington famously collapsed from exhaustion in 2007, shattering her cheekbone in the process, the entrepreneur seized the experience as a wakeup call that ultimately changed her life. In the years since, she has set up an organisation called Thrive Global, which aims to end the burnout epidemic.

“(That fall) put me on a course in which I changed how I work and how I live,” Huffington explains. “It put me on a course of writing two books, Thrive and The Sleep Revolution. And, not long after that, it led to me leaving a very successful company I co-founded and ran for 11 years to launch another one, Thrive Global.”

While Huffington admits collapsing “in a bloody mess” might seem like an odd thing to celebrate, it was also the catalyst for a decade of growth.

“In fact, one of my goals with Thrive Global is to provide a softer wake-up call, to provide the catalyst for other people to get on a different course that can bring just as many positive changes to their lives without hitting the wall – or the floor!” says Huffington.

Jen Atkins, Founder of OUAI

Celeb hairstylist and OUAI haircare founder Jen Atkins has built her business around making women feel good, but she admits her biggest mistake was not hiring more of them in the first place.

“I never used to have female assistants,” Atkins told Business of Fashion. “I insisted on having boys because I was afraid that women were going to be too emotional, fragile. And you can’t be fragile. Hairstyling has always kind of been a boy’s game.”

Atkins says her first female assistant hire made her realise this logic was flawed, saying the experience highlighted what great multi-taskers women are.

“We got ten times the amount of work done than with the boys!” she says. “That’s something I regret not doing earlier — trusting that women could carry heavy luggage, keep up with the travel schedule and not lose their minds. In my industry, it was hard for me at first to get a job. I only had Sally Hershberger and Odile Gilbert to look up to. I was a part of the problem myself for not putting faith in girls. So I regret not doing that earlier.”

Any advice provided is general advice and does not take your personal circumstances into consideration. Please read the Stella product disclosure statement (PDS) available at for the terms, conditions, and exclusions before purchasing this insurance. Stella Underwriting (ABN 72 633 811 319) is an AuthorisedRepresentative (AR 001282046) of Allstate Insurance Pty Ltd (ABN 82 073 267 053, AFSL 239010) which is acting (under its own AFSL) on behalf of the product issuer, QBE Insurance (Australia) Limited (ABN 78003 191 035, AFSL 239545).

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