• Laura Hay, Leadership |

International Women’s Day is a great opportunity to learn the often-unheard experiences of women. For example, it might surprise male executives to discover that some female colleagues take years to realize – and take action – to build the careers they actually want. While men are typically quick to seek out what they desire, women may feel the need to conform with others’ expectations, before they gain the confidence to ‘steer their own ship.’

That’s an insight from my conversation with Helen Weinstein, General Counsel of DARAG North America, the Atlanta-based insurer/reinsurer. Helen sincerely described how, while building a successful private practice law career, it took nearly a decade before she had the chance to make choices that matched her own priorities.

No doubt many professional women can relate. For example, who hasn’t spent hours mediating peers’ needs, before ensuring your own requirements are met? Or, who hasn’t bent to friendly pressure from a manager regarding a promotion? Or, on a personal note, how many mothers have eaten a cold restaurant dish because they first helped the children select, cut, and consume their meals?

If this sounds familiar, Helen provides real evidence that you can turn the ship – sooner than later – if you “Listen to your gut.” And, she’s continued to honor a self-styled, risk assessment process to keep her chosen career and life on track.

Stop doing what the world tells you

While summing up her journey as, “a typical lawyer’s progression, from legal clerk to large law firm,” Helen says that the main obstacle she faced was pressure to conform with others’ expectations. “Looking back now, I felt that my decisions were driven by, ‘What I was supposed to do?’ versus ‘What did I want?’ My impression was that I had to just keep working and that didn’t leave time to see what I wanted, or take the steps to get there.”

Noting that, “In a service-driven industry, you may rise blindly through the ranks without asking yourself, ‘Do I really want this?’” Helen says that she even ignored the physical red flags, including sleepless nights, and the stress of juggling marriage and an intense career.

Her inflection point came as the result of a recruiter’s call, and a tempting in-house counsel position in financial services. “This was a difficult decision, and a big risk, since it meant walking away from a path I’d been on for a long time. But my gut told me that my current direction was not right for me.”

Helen says that she performed a frank risk assessment of her options: “I told myself that there’s a risk either way – of taking the new job or staying where I was – and I had to decide what was more palatable.”

She also told herself to ignore the ‘external noise’: “There is so much pressure from the outside world that tells you what you should be doing – whether that’s to be a leader or stay at home – you need to figure out what you actually want. Whatever you choose is okay, as long as you make a decision, and not because others are telling you what to do.”

When her career leap paid off – and she attained a challenging, flexible role in the insurance sector – Helen realized the value of regularly re-assessing one’s place and path. “It helped me develop a growth mindset, so that whenever I start to feel too comfortable, I ask myself, ‘What do I want next and where do I want to go?’”

For example, Helen later made another strategic career jump, despite the added challenge of raising a two-year old: “My personal risk assessment told me that, ‘If I stay in my current role, I’m actually taking a bigger risk, because I don’t know if this kind of new opportunity will ever come my way again’.”

Empowering others to choose their path

While today Helen mentors other women to be self-aware, be open to risks, and make their own choices, she adds that employers can do more to empower their people.

“While women face ‘internal struggles,’ including the fear of risk-taking, employers could help, by adopting more flexible people management,” she suggests. “For instance, leaders must ensure they are giving employees the support they need, not the support they think they need. Managers should take a more individual approach with each employee, rather than applying the rules to everyone the same way. I think COVID-19 showed us that flexible work arrangements do work, and we can each overcome our past biases, find ways to have happier employees, and still get the work done.”

Reflecting on the significance of International Women’s Day, Helen observes that, “While there is still so much to do to improve women’s access to opportunities, I feel lucky to live in this time, because we can make our own choices on many levels. You may always feel fear of the risks, but the most important thing is to make your own decision. It hasn’t always been easy, but I’ve learned to really listen to my gut instinct and that is my compass in life.”

More about Helen Weinstein: Based in Atlanta, Georgia, Helen is General Counsel at DARAG North America, the North American division of the international insurance and reinsurance group specializing in legacy business risk assumption and capital relief solutions. Prior to joining DARAG in July 2020, she dedicated five years to Hiscox USA, a leading small business insurer, where she held increasingly senior positions, including Senior Legal Counsel and Vice President. Helen began her legal career as a Law Clerk in Federal District Court, before serving as a Senior Associate at several prominent law firms in the Greater Atlanta Area. She holds a Doctor of Law degree from the University of Georgia School of Law and a Business and Economics degree from the Terry School of Business at the University of Georgia. 

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