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Written By Leanne Redden 

Executive Director, Regional Transportation Authority & WTS Board Director

Never show weakness, never ask for a break, definitely never cry. Be tough, no compromises, no asking for help. Early in my professional career I thought those were the rules that women had to follow to get ahead – essentially, act like a man. But when you’re up all night with a baby in the ICU and expected to work a 9-5 job, a lot of those rules go out the window.

More than a decade ago I was at a crossroads where the needs of my career and the needs of my life were pulling me in opposite directions and threatening to split me in two, or fifty, pieces. I had four-year-old twin boys, one of whom was recovering from major surgery and needed round-the-clock care, plus a busy schedule as Director of Planning at the Regional Transportation Authority (RTA), the public transit agency that oversees finances and planning for the Chicago Transit Authority, Metra Commuter Rail, and Pace Suburban Bus.

During the most difficult moments I thought I would have to quit my job and walk away from a career I had worked for more than 20 years to achieve. But I was lucky enough to have a supportive work environment and negotiate working part-time. I had built a strong team and could rely on them and the leaders above me to have my back. I also had family, mentors, and advocates – including my network from WTS – telling me it was OK to step back and that my career would still be there after the crisis passed. Unfortunately, during the COVID-19 pandemic we have seen many people, mainly women, leave the workforce because they don’t have that support.

That difficult period was not the first time in my career I learned that flexibility makes us all better employees. Having children later in life meant I saw many other women deal with difficult decisions and bosses who required them to be in the office even as technology made it possible to work from anywhere. I told myself that when I became a manager, I wanted to become the boss I always wanted to have – empathetic, flexible, creative.

Over the years I have constantly advocated for policies that give employees the freedom to do their best work. It hasn’t been easy and there has been pushback along the way. As a government agency, the RTA is accountable to the public and we prioritize using taxpayer money wisely, including how staff use their time. But I would argue that employees who feel supported are more efficient and more effective.

When I first started at the RTA, two talented women I managed each had young children at home and were struggling to work full-time. It seemed simple to find a creative solution where they could essentially split one position, but it had never been done before. Pushing for flexibility, allowed us to keep both employees happier and producing better work than before.

Obviously the COVID-19 pandemic changed everything. Workplaces all over the world have pushed the limits and proven what they can do outside a typical office environment. As many employees and employers contemplate the challenges and benefits of going back to physical work in some way, I hope they’ll bring with them the lessons they learned about flexibility and empathy.

We have now seen that so much of our lives cannot be checked at the door or left off a Zoom call. Distancing physically has shown us how much more we need those mentors, advocates, and support systems.

I’ve also learned that our careers are a marathon, not a sprint. It’s hard to remember that in the moment. When you are up in the middle of the night with a crying baby and you know you have an important meeting at 8 a.m., or when you have to step away from an important project to take care of an aging parent – it’s easy to lose sight of the longer perspective. Early in my career I thought I could do it all and have it all too, but I quickly learned that was a myth.

To advance and grow is not always a series of steps up and forward. Sometimes you have to take steps back, or to the side. Five years after I had to step back to care for my family and myself, I was named Executive Director of the RTA, a role I still hold today. My two healthy teenagers are busy with activities, e-learning, and bouncing around the house during quarantine while I work with my team and counterparts on strategies to sustain public transit as an essential service for the Chicago region’s recovery. At mile 2, reaching 26.2 seemed impossible, by mile 22 -- it’s within reach.