What I Wish I Knew Planning Does Not Always Work
Dana Bloom, VP & General Manager of Keep Collective, Stella and Dot

Teaching Guide for Women Inspired Program


In today’s world, highly talented women continue to face challenges that limit their success, career potential and general life satisfaction.  In partnership with the GSB Women's Task Force, the GSB Alumni Relations Office makes these resources available to spark thinking and discussion on important topics of career navigation, leadership through awkward dynamics in the work place, work-life balance, and diversity. 

These resources are designed to challenge you to grapple with the forces driving your own internal compass and gut reactions as you watch, discuss, and share a combination of both the Capstone Perspectives and Video Case Vignettes.

Women Inspired Program Vignettes

This content is designed from real stories and perspectives of diverse women with the simple assumption that career satisfaction and life success are driven by the ability of a woman to make consistent value judgments and decisions that are driven by an inspired perspective of oneself and ones life vision.  The vignettes and cases are structured to spark personal reflection around one's own values and decision-making process, which will lead to transformative learning of practical ways to address challenges.  The video case resources are made available to all alumni and the content is designed to be experienced individually, in a group discussion or with a professional coach.

The collection includes two different types of videos: Capstone Perspectives and Video Case Vignettes.  The Capstone Perspectives feature a woman’s perspective, experience or advice on a particular topic or theme.  The Video Case Vignettes focus on a particular challenge a woman faced, decisions she made, and what she learned from the experience.

Video Case Vignette Format

These case vignettes feature leaders who share their experiences and insights to help you understand the opportunities you have to hone your own thinking and career design.  The case vignettes are broken into 3 clips: the background and challenge; the decision or action taken by the leader and the results of the case with lessons learned.  At the end of each clip, take time to consider or discuss how you might handle the dilemma, whether or not you agree with the action that was taken, or what you might do differently and why.  Take heed of the lessons learned and see what advice you can take from leaders who have gleaned important insights from their experiences.

How to Make the Most from the Video Vignettes

Try to watch a combination of Capstone Perspectives and Video Case Vignettes from different leaders.  In many cases, you will see that leaders may handle the same question or challenge very differently.  Consider which approach or perspective works for you.

As you watch the videos, reference the scrolling notes next to the video, which includes a brief background on the leader, a summary of the vignette, take-aways, and questions to consider.  For every vignette, ask yourself whether or not you agree with the leader.  Try to understand what values or frameworks are driving your reactions.  If you have not yet faced a similar challenge, consider how you might use the challenge to prepare for what may lie ahead.  You may also recall a very different challenge you have faced that brings you to a similar conclusion as the challenge in the video.

As the leader shares her challenge, imagine yourself in her shoes and how you would handle the situation.  Pause the video to consider and/or discuss the challenge, how it is handled, and the lessons learned.  Think about what you might do differently or what was done well.  Use these stories and insights to consider the values and decision making processes that drive your own internal compass.

Take time to reflect on your own situation, goals, values, plans and future.

After you watch the video, ask yourself the simple question:

What will you continue doing? Start doing? Stop doing?

Additional Readings and Resources



Video Vignette: Planning Does Not Always Work

Featuring: Dana Bloom

Background on Leader: Dana Bloom is the Vice President and General Manager of KEEP Collective, a subsidiary of Stella & Dot.  Previously, she worked at Bain & Company where she advised some of the world’s leading fashion and retail companies to turbo-charge their revenue and profit growth. Prior to Bain & Company, Dana served as General Manager for start-up company 1stUp.com, where she launched a broadband internet service. Dana also did a stint as a private equity investor at Bain Capital. Dana graduated from Stanford University and Stanford Graduate School of Business. Having worked in the US, UK and Austria and traveled to over 50 countries, Dana couldn’t be more excited to take Stella & Dot global. Dana currently lives in the Bay Area with her son and husband.

Summary: Dana talks about dynamics and insights she has gained through experience she wish she knew when she was younger.

Takeaway: Know that you cannot perfectly plan your career and life.  There is never a perfect time for motherhood, but if you enjoy what you are doing, you will find a way.

Considerations and Questions:

1-    If you cannot plan, what should you prioritize to be positioned well when you start a family?

2-    How can you be aware of workplace dynamics that will help you when you may need more flexibility?

3-    Rather than planning your life, where should you focus your efforts?