An Accelerator for Women that Educates and Empowers Female Empty-Nesters to Re-start Their Careers  

When Diane Flynn returned to the workforce in 2014 after raising her three children, she discovered substantial changes had taken place in her absence. Despite her education (she attended Stanford for her undergraduate degree and Harvard Business School for her MBA), nothing at either school prepared her for standing desks and flexible work schedules at her new job at GSVlabs, a startup accelerator in Silicon Valley.

One might assume that her previous work experience, first at BCG in Chicago and then at Electronic Arts for ten years, coupled with the hours she served as Advisor to Stanford Children’s Hospital during her work hiatus, would have assured Flynn an effortless transition back into the workforce.

Not so. Various elements of her new job, which she discusses below in detail, were  not necessarily comfortable at first — though that later changed. In fact, even taking the position at GSVlabs in Redwood City, California caught Flynn a bit by surprise.  She explains: “Honestly, I wasn’t looking to return to work full-time. An opportunity arose to help with a turn-around, and I committed to 25 hours/week.  That quickly resulted in full-time work, which I found I was enjoying immensely.  Two of my three kids are out of the house, and I had the time to consider re-engaging in meaningful work outside the home.”

Flynn then turned the experience of her early days at GSVlabs into a program to help women through what can be an uncomfortable, even fear-filled time in their lives. The ReBoot Career Accelerator for Women helps women become “current, connected, and confident to return to work,” Flynn said.

So given that many women feel like “fish out of water” when they go back to work full-time after a hiatus, we asked Flynn to share her experiences, and how they inspired ReBoot.

What were the most difficult aspects of the transition for you?
These were all new components for me: getting up to speed with the latest technologies (which seem to change weekly!), having a growth mindset, working with millennials, adapting to a more fluid and flexible workplace, and working in an open environment with constant interruptions and standing desks.

How did Reboot Accelerator for Women come about?
As I shared my story of returning to work with friends, many of whom were facing an empty nest or going through a major life change, it seemed that there was a large group of women interested in re-engaging in paid work.  The problem is they didn’t know how. They didn’t feel current with technology, connected with the right network, and confident in their skill set.

What are the goals of Reboot Accelerator?
We offer a survey of all the latest technologies you need to know in order to return to work.  We introduce women to office productivity tools, get their LinkedIn profile (and picture) current and persuasive, provide them with accountability partners, help them adopt a growth mindset, and greatly increase their confidence.

What do you think are the biggest challenges that women face when re-entering the workforce or when changing careers?
Lacking confidence is probably the biggest barrier in returning to work!

ReBoot Career Accelerator for Women recognizes that even building a wardrobe to return to work can feel like a big deal when a woman’s closet is filled with yoga pants and jeans, so it addresses that as well. Flynn explained, “We actually have an image consultant speak to our cohorts about creating your professional image. It will differ for every woman, but essentially, the goal is to dress in a current way that’s age-appropriate and professional. The new casual work culture often makes this more challenging, but having key go-to pieces can make it easier.”  They also offer “Club ReBoot” which offers workshops in tech, networking and job skills, so that women can stay connected with the Reboot community and continually refine and expand their skill set.  

Flynn’s favorite part of getting all of this up and running, she said, is “Creative collaboration with people I respect, around issues I care about.” She explained that she never could have done this by herself, adding, “It took a team of six women, all of whom I’ve known over twenty years, to create this program.  They are an amazingly talented and committed group, and without them, ReBoot would never have come about.”  That group ranges in experience and age group from millennial to empty-nester.

Reflecting on Key Influences and Core Work Philosophy 

Flynn’s current role isn’t something she dreamed about from a young age, as she notes: “Even eighteen months ago, I never envisioned being CMO of GSVlabs and building ReBoot.  I have learned to have a growth mindset, to say YES to opportunities that fit with my skills and passions, take small bets each day, and see where the journey leads.” Her experiences as a child, however, did influence her thinking.

When you were a child, what did you want to be when you grew up?
I walked through General Mills with my dad at the age of twelve.  He was the VP of Corporate Planning.  The only female role models I observed were secretaries, so that’s what I told him I aspired to be.  I’ll never forget his response: “Why not be the boss?”  This little voice of inspiration motivated me to ultimately attend Harvard Business School, and gave me the confidence to start ReBoot.  He taught me I can be anything I want to be.

Knowing what you know now, what career advice would you give to your 20-something self?
That’s easy, since I have two daughters in their twenties!  I would say to find your passion, continue to learn and grow, build your skill set, identify your talents and gifts, and put them to work in a way that brings you joy.  Live a life of balance.  Interestingly, that was the word I chose when I applied to Stanford.  The question was “What is one word you’d use to describe yourself?”  I chose “balance,” and I would choose the same word today.  I feel very blessed with a fulfilling life, and I attribute much of it to knowing what priorities are important to me, and making sure each day encompasses these.  My family, friends, faith, and health, along with making a meaningful impact in my life, are all important.  I try to ensure that each day incorporates a bit of each.

Who have been your role models?
Indra Nooyi, who was my mentor at BCG in my early twenties, and who is now the CEO of Pepsi.  I reconnected with her a few months ago because I was impressed by her support of women in leadership, and she has been incredibly responsive with her support of ReBoot.  I’m also fortunate to have Bill Campbell, the “coach of Silicon Valley” as my mentor.  He has really helped me in my role as CMO, and has taught me about the importance of getting the product right before trying to embark on anything else.  

Smart Prioritizing at Work + Family Time = Achieving Balance 

Flynn’s typical work day starts at 6:00 a.m. when she hits the gym while reading the San Jose Mercury-News and the WSJ.  Usually, her son (the last of her children still living at home) and her husband head out together to eat breakfast, allowing Flynn to get to the office early to read emails — her goal being to keep her inbox at zero, which she called, “an aspiration more than a reality.”

To keep herself focused and motivated, she starts each day outlining what she wants accomplish, which ensures that she attacks the important, not the urgent. She has “become better at carving out time for ‘deep work,’ the work that requires focus and strategic thinking.”  For deep work, she schedules time out of the office so she can really reflect on crux issues. Today’s flexibility allows her to manage the workload, be home for most family dinners, and never miss a special moment with her kids.

The thing that causes Flynn the most stress and anxiety?  It’s likely something many other working moms share: “Definitely anything relating to my kids and their happiness, she said, But I have learned to tap into my faith, and not let the ups and downs of my kids impact my personal life as much.  There is only so much you can control, and while I’m always there to love and support them, I must also let them experience their own disappointments and grow from each experience.  Resilience is an important character trait, and it only develops through challenges.”

Workouts, girlfriends, and reading are her favorite go-to activities to stay energized. Flynn added, “For personal refreshing, I enjoy a walk, a glass of wine, a bath, or a good book.  Beating my husband of twenty-eight years in Scrabble is also always immensely rewarding…!”

The one piece of technology she’d be hard pressed to do without? Her iPhone.  She said, “It’s hard to image going through a day without it, though I do put it away during meetings and family dinners.  I really try to focus on the people around me.”

An avid reader, Flynn’s recommendation for women is a book she recently read called Find Me Unafraid by Kennedy Odede and Jessica Posner, which she called “an inspirational book about making a small bet and making a difference in the world.”  

ReBoot and Flynn are making a difference in the world, one woman at a time. ReBoot’s program offerings include a four-day Immersion Accelerator, an eight-week Accelerator, and a Purpose and Passion Workshop. For Flynn, the best compliment she has ever received are the words, “You’ve made a difference in my life.” With the valuable training and encouragement that ReBoot Career Accelerator for Women provides, Flynn is likely to hear those sweet words more frequently.