Welcome any unexpected career path twists

With summer vacations winding down in many parts of the world, you might have enjoyed a precisely planned itinerary. Or maybe you embraced a rambling road trip and welcomed unforeseen turns in your route.

While either style of holiday is fine, the same can’t be said for career paths, since it’s often best to “go with the wind” and willingly divert from your plan if unexpected offers come along. Unfortunately, I often meet professional women who resist such career twists that could yield invaluable growth. Maybe they don’t feel ready, or they simply dislike surprises on their carefully mapped path.

For that reason, I was happy to chat with Julie Dillman, of Chubb.

Welcome career ‘left turns’:

Today, when you see Julie confidently steering Chubb’s technology and operational groups, you’d never guess that she reached this point after grudgingly accepting an unexpected job change.

“After spending half my career in underwriting, I was urged to take a senior technology role, based on my experience bridging the business and technology groups in a recent company integration,” recollects Julie. “I responded by saying, ‘But that is not my career – Why would I do this?’ After they persuaded me to accept the role, I went kicking and screaming into that assignment, and since then I’ve never left technology.”

Julie adds that this wasn’t her first time making a big career leap. At university, she studied speech disorders and was unblinkingly focused on helping traumatic head injury victims. Then, before beginning graduate studies in the medical field, she took an entry-level underwriting role for an aviation insurance broker. Something ‘clicked,’ and she never looked back.

“These types of moments in my career are very good lessons because by accepting an unexpected opportunity, I found places to work where I felt very much at home, where I love to work and learn,” observes Julie.

Be prepared to ‘learn as you go’:

“Willingness to learn” is definitely a key to Julie’s success in making bold career shifts. That’s especially true when a new job opportunity required her to lead her company’s data scientists even though she didn’t feel deeply steeped in business analytics at the time.

To do so, Julie states that, “You need to adopt a learning mindset so you can add value and credibly make decisions in that discipline. Learning as you go and leaning on the expertise of others - rather than waiting to master every skill - is critical since you could never be an expert on every topic.”  

This, she adds, means that, “You must be willing to show your own vulnerability and ask enough questions to get the right details. Even today, when I’m dealing with very complex issues, I may slow the conversation down and say to colleagues, ‘Okay, help me break this down and understand what this means so I can make the right decision for the business.’ Most times, people will respect that and support you.”

Perhaps most importantly, Julie implores women to “find and listen to” their career sponsors, including those individuals who encourage them to apply for ‘stretch’ assignments, or those who offer honest advice. “I took that technology job because I realized that one particular career sponsor saw my abilities and potential, even before I saw it myself.”

In another case, Julie benefited from a male sponsor who told her that, “’You have so much potential, but you need to develop some armour, because if you take feedback too personally, it will destroy you.’ This feedback taught me to better balance ‘grit and grace’ in my style.”

Julie points out that ‘grit’ means being ready to ‘learn as you go’ in an unfamiliar role, being strong enough to bounce back from criticisms or failures and, speaking up for yourself: “This doesn’t mean being overly aggressive, but women should ask for a bit more, and advocate for yourself if you see an opportunity.”

Modelling behaviours for others:

These days, Julie models these behaviours for up-and-coming women leaders. “For women of my generation, you could lose your sense of self because you had to play a certain role at work, and maybe conceal the other sides of your life, such as being a mother. As I grew in my career, I became more confident bringing my authentic self to work. Things are better today - but there are still not enough women at the table - so I try to model these behaviours for other women who are looking in.” 

Julie’s modeling includes subtleties like how women should “show up to a meeting”: “I tell women to sit at the middle of a boardroom table, not at the end. As women, we need to take up space, and be seen. So, choose a middle seat, sit up straight and project yourself.”

Julie’s top recommendation is reassuring for any women who cringe at the thought of embracing stretch assignments, learning as you go, and standing out in the boardroom: “First and foremost, I tell women to ‘relax’, since you will have a long career and it’s okay if you make a wrong turn. I know many women prefer to plan and be very thoughtful about each career choice, but these unexpected assignments help us grow and prepare for careers we never imagined for ourselves.” 

At the end of the day, I think Julie’s ‘relax and embrace the unexpected’ philosophy is the making of both an exhilarating summer vacation and an enriching, rewarding career.

More about Julie Dillman: Drawing upon more than 30 years of experience in insurance company operations, Julie is Executive Vice President, Chubb Group, Senior Executive, Operations and Technology, and Digital Transformation Officer for the global insurer, which spans 54 countries and territories as it provides commercial and personal property and casualty insurance, accident and health insurance, reinsurance and life insurance. In this role, Julie helps lead the company’s transformation and provides executive oversight for global operations and technology. Julie joined Chubb in 2016 from Travelers Insurance, where, over her 11-year tenure, she held positions such as Executive Vice President, Operations, eBusiness and Analytics, and was a member of the company’s management committee. She was appointed Senior Vice President, Chubb Group in 2016 and Executive Vice President, Chubb Group in 2022. Julie began her career as an underwriter and held positions of increasing responsibility, including product development leadership and integration leadership roles. Julie was honored in Insurance Business magazine as one of WomenInc.'s 2022 Most Influential Women Executives in Corporate America. She received a Bachelor’s degree from the University of Wisconsin – Eau Claire.