why i quit my dream job

The short answer is… there wasn’t enough joy in my work anymore.

To be clear, it really was a dream job, a once in a lifetime opportunity for which I am eternally grateful. If change wasn’t inevitable, I would never have wanted to leave.

For 11 of my 21 years at Microsoft I worked with an incredible team of people who I loved very much; all geniuses in their own right. Imagine the good fortune of being paid to think about and tell stories of how technology will benefit us in the future. For years I would skip into work grinning from ear to ear. It was a really good thing.

Not all was bliss though; I was a creative type working in an environment where analytical thinkers and doers were valued highly. I never quite fit the corporate tech culture although was fine being a misfit as long as I felt respected.

My boss had the foresight to know the importance of having a diverse team of perspectives, thinking, and experience for our task. We created a balance important in designing lasting concepts for the future. We took our jobs seriously working to do the right thing for the company and humanity. For many years we had the autonomy and freedom to create without prescription. We were successful and happy.

Evolution happens.

For long time I would just dream up concepts, relying on my smart colleagues to tell me if they were viable. Together we developed valuable work. I had a broad but shallow understanding of what technology could enable. Somewhere along the way it became important for me to go deeper into the tech and include a due diligence of research and analysis in order for my work to have a similar value (become more like them). This required a different approach. Enjoying a challenge, I tried to work more analytically. Unfortunately my voice and creativity became lost in translation. Eventually my work became stale and looking around everything we were producing now tasted like institution.

During the 11 years, the evolution of technology forced incredible change in the world and much of the world had caught up to the future. The technology and innovation of the present was amazing and in a sense our competition. All along, our team tried to design for individuals vs. institutions, but this began to feel self-serving as other companies leapt past us with cool personal products on the market.

To complicate things I was in a new life stage. My own personal evolution introduced perimenopause; it was in full swing and not being kind. Not an easy situation to describe or experience especially in a company that was 76% men. My work world was in a downward spiral.

A few things sustained me for a while. My love of meeting with visiting guests and ability to communicate the benefits of future technology to them in a way that resonated. We also hired a brilliant new design manager who had the passion and drive to do the very best work possible. She inspired me and I clung to her sails for as long as I could.

Unfortunately slowly I began to shut down. I became lost and unhappy. I used to love my job, the work, the process, the outcome. That was gone. Alone I could develop a plan and process for moving forward, but too often when it met with resistance I froze and had no language to move us forward. This is a terrible place to be in when leading a big project. We all deserved better.

We were about the future, where it’s not business as usual. I didn’t know how to reflect this practically in our work process to help the team evolve.  My strength was in telling relevant stories about people’s futures.

Situational awareness kicks in. A series of events happened that made my consciousness shift.

I helped my friend die.

Our best friends living next door made the difficult decision to move after living in their home for 30 years.

I recognized my daughter would be entering her last year of high school in the fall. I had spent her entire life working a demanding job at Microsoft and was poised to spend the next 18 months crazy busy.


I was sitting in my office preparing for a meeting I’d be leading. I looked out the window and saw a bus. I thought to myself, I’d rather walk in front of that bus than go into this meeting; seriously.

A dim bulb lit in my head- what insanity is this? I had to figure a way out.  The meeting came and went; ironically it went well although it didn’t matter I was already on a new path. On the bus ride home that night I silently cried to myself. It was over. It was like a veil lifted to expose lack. Lack of doing a good job, lack of creativity, self-respect, joy… I was sick and depressed.

I am not in a position to retire, so I had to look at what might happen if I quit my job. I came to the conclusion that we might have to sell our house. Then I asked myself – when have I ever not had enough? Enough food, shelter, things like this… the answer was- I have always had enough.

On the corner of my office white board were posted my values. They are: Respect, Joy, and Appreciation. The intent was to check in on them regularly and make sure I was making choices based on them. Somewhere along the way I’d traded personal respect for security, joy for $, and appreciation for apathy. All so I could maintain a lifestyle tied to having and maintaining “stuff”.

Being conscious not to make big decisions based on fear, I decided trading my house to realign with my values and find potential happiness would be worth it.

When change happens we either adapt, suffer, or leave to survive.

I am eternally grateful to Microsoft. I hope our paths cross again.


Quitting my job didn’t fix my problems. I became even more depressed.  In hindsight my issues with my working situation were mostly due to my inability to see any joy, not Microsoft. Often the issues we have with others are really issues with ourselves.

After a long road, I found I have a gene mutation that causes depression and now take L-methylfolate which has thankfully taken the depression away. Read about my discovering the root of my depression.

why i quit my dream job

grandma out of the box

Tomorrow our granddaughter Mila comes to visit. I can’t help but think about Mila’s response to grandma out of the box. The last time we were in the same room together was last summer, half her lifetime ago. Since then we Skype weekly, so most of her experience with Grandma has been in the box.

I am reminded of a scene “Life imitating Tech” from a few years ago. My colleague Ethan showed me a picture from when his parents had been visiting. His parents and daughter were “fake” Skyping while in the same room. At his daughters’ request, Ethan made a Skype theater out of cardboard; think Puppet Theater.  His parents sat on the back side of the theater while Ethan and his daughter sat in front as they had a conversation. I imagined Skype had been their primary mode of communication and her most common experience with them. It was how she knew her grandparents. These real people were likely ok but different than the context of their regular relationship, so she may have wanted to put them back in the box.

We are dependent on screens. Technology continues to morph society and what it means to keep connected, as new experiences become ritualized.  The current generation (first world) is also being raised with different rules for time and space than I had growing up. I remember as a young adult, the longing I had for my parents after not seeing them for extended periods of time. This longing was met with an unsettling vivid image as I walked off the plane at age 20 after not seeing them for a year. I was crest fallen to see how old and small they had become. They looked fragile for the first time. My familiar parents became only a memory. I now had to create a new relationship with these changed people. The crazy thing is that the journey I had just taken from one coast to the other took only 6 hours, something my parents weren’t able to experience as children. Each recent generation appears to be redefining personal relationships as technology drives change. Maybe redefining isn’t the right word, although we are clearly experiencing each other in many more formats as time goes on.

Back to Mila… she is so freaking cute I can’t wait to squeeze her (lovingly). I ask myself all kinds of questions about our new relationship. Will she want to touch me? Will she prefer to fake Skype?  Will she want to see me in my red robe, my normal Sunday morning Skype attire? What will Mila think when she sees my robe hanging on the hook? Will she recognize it? Will she wonder if my physical head gets really big like it sometimes does on screen? …

Memory is funny; I started writing this post without remembering I had imagined this scenario 12 years ago. Pre grandma, I led a project at Microsoft that had a vignette of future communications with grandma. My work usually centered on personal experiences, so I would draw from my own imagined future experiences. I would also drag my kids into it. The video below stars my youngest daughter Ruby at age 6 (next month she’ll be 18). Unfortunately this video is very small. At the time disk space was at a premium and we were working with a 640 x 480 resolution …

Now here I am on the other side of the future, and it is to some degree how we imagined it, only way more personal.  I am so looking forward to staying connected with Mila as she grows up and the new ways of connecting that her generation will bring.


grandma out of the box


21 years of Microsoft experience, 11 were spent imagining the future. Together with key stakeholders we created presentations and prototypes that embodied the company’s dreams for future technology and computing.

Prior to leaving the company my primary responsibility had been managing the vision and experience within the Microsoft Home, a world class future envisioning facility housed within the Redmond Executive Briefing Center. At the time of my departure, the Microsoft Home was the most requested and highest rated session offered to business guests.

I am creative with just enough understanding for technology to enable leading technology projects. I am not technical.


Contact flora@floraGo.net



I lead our teams’ effort for the vision portion of Bill Gates last CES keynote. We highlighted the concept of “information anywhere” by creating a phone hardware/software prototype that showcased 2 scenarios: a digital guide for the real world; and accessing our digital history.

Scene 1- Real World Digital Guide

We envisioned how future digital lifestyles would use phones and other evolving devices to overlay the physical world with real-time information through software and services.

Using the Vegas strip as the backdrop and looking through the prototypes camera viewer, Bill observed contextual information and recommendations overlaid onto the world, and presented real-time.

We built a phone prototype (nicknamed “phonosaurus”) that used a combo of software from research and our team. Behind the scenes technologies included: GPS, camera’s and machine visioning ,info in the cloud, contacts, events, preferences, tracking behaviors, the weather, subscriptions, even sourcing 3D model information of the world from things like Photosynth and Virtual Earth.…

In January2008, phones had cameras and GPS which allowed you to know where you were, but not what you were looking at or how it’s related to your life.

Scene 2- Digital History

Here Bill and Robbie Bachdiscuss how all types of content will be accessible and easily shared through any device, anywhere we are. Like a unified library…content available in a single view no matter where it resides (PC, phone, cloud, etc…).

An individual’s history was viewed on a timeline. The timeline was accessed from the phone and then using a gesture, shared to the large screen in the room. The transition was seamless taking into account the new screens capabilities and restructuring the UI accordingly, rendering high res- images and 3D capabilities.

Here’s a low res version of the keynote.


pam and help desk

I will never forget the time when I was sitting in my office and heard Pam’s office door open. The opening of the door brought a quick presence to the moment which drew all attention to Pam.

She walked over to Sven’s office and then back to hers where she picked up the phone to continue a conversation with help desk. Her voice was composed and precise…
“Sven is not in his office. I can only assume he is in the rest room puking up his guts. I have already emptied the contents of my stomach so am able to have this conversation with you. In case I haven’t made myself perfectly clear, this is for Bill Gates, the flight leaves in 2 hours and we need access to the server now in order to copy the files to a portable hard drive.” Pam never missed a beat. Although not audible, I could feel the sweat and panic coming from the other side of the conversation.

Bill was a regular customer and our team had created a demo/prototype for him to present at an event. The server had been down for hours and the help desk team was franticly working to solve the problem. Happily the server came back online in time to get everything copied. This was before remote access had decent speed or reliability.

Pam is a true role model, always calm and clear with her intent; I was lucky to work with her for five years.

pam and help desk

hostess gifts

One of the perks of giving tours of the Microsoft Home was receiving small hostess gifts from visitors. These gifts usually had little monetary value although held significance for the giver; sometimes a cultural icon, an example of art and engineering, or symbol of friendship.

I would re-gift most things. I always got a kick out of passing things onto my colleague Jim. I would stand in front of his office with something like a packaged set of character key rings for the 2010 Olympics, while spewing that plastic crap like this would be the end of us all… when he would leap from his chair and squeal with delight saying how cool they were.

The gifts also made for great contributions to my friends yearly white elephant party. Year after year I would bring a small collection and people would fight over them; a book of stamps, cloisonné necklace, a silk scarf… to add my mark, each re-gifted item was accompanied by a riddle or poem describing the wrapped gift and the original giver. It seemed right to include some of the gifts history.

The gifts I valued the most were ones I developed personal meaning for. Among them are a paperweight, nail kit, and a blue bag. Each now represents a small story. The stories have nothing to do with the givers intention, but relate to my personal meaning for them. That’s the thing about giving gifts once they are given they often take on new meaning.

The glass paperweight was a gift from a Taiwanese development company Farglory. They were building a new city and had come to Microsoft to discuss partnership and technology needs. The glass is faceted and looking through it produces beautiful effects that remind me of perspectives, each prism produces a different view. The paperweight is also inscribed with the following:

Microsoft May our friendship lasted forever”

I kept this as a reminder of the power of communication and how positive intent is often lost in translation. It was clear that they wanted this to be a symbol of friendship. However because the statement was awkward, it amplified the cultural gap of an unshared native language. I identified with this gap as I often struggled with communicating my intent to the world of corporate business software. Preservation of identity and culture is important; I hope that Farglory doesn’t feel they need to be more like us.

Nail Kits
The nail kits represent before and after 90 seconds of exposure to fire. The new kit was a gift from ING, a partner of Microsoft, and frankly I can’t remember the specifics of this particular visit although the gift struck a chord.

A few months prior to ING’s visit we received a call in the middle of the night. My son Sam was on the other end. Sam- “Mom, I’m in a bit of a predicament.” Me- “Son, its 2:38 am what the @&#$ is going on.” Sam-“Our house burned down”.

4 minutes later I was at the scene a few blocks from my house where I found Sam, Jordan, and Bennett on the street in their underwear with firemen attending to the remaining structure. The fire had taken half the house. Only 1 smoke detector was working in the house, it was upstairs outside Jordan’s room and luckily he heard it.
The next day as we picked through the wreckage looking to see what could be salvaged. I found a nail kit in what used to be the bathroom and decided to keep it as a souvenir. The plastic top had melted onto itself creating a strange kind of mummification. The bathroom shared a wall with Sam’s’ room. Sam was sleeping when the fire started and his room was the next to go.

One of the firemen told me it takes 90 seconds to destroy each room once a fire is going. These 2 kits now sit as a pair and a reminder of the impermanence of life, before and after 90 seconds.

The Blue Bag
We often received gifts that were wrapped. The anticipation and promise of each wrapped gift made them fun to open for a while, but being continually disappointed gets boring. When I received the blue bag I decided not to open it. The idea of what could be in the bag was likely much more interesting than the gift itself. For years the bag was attached my office door with a paper clip. When people would ask what was in the bag I could honestly say I have no idea. This made for interesting conversation as well as pushed some people’s buttons.

At the end of a contract, a designer who was leaving asked if she could look inside the bag if she promised not to tell me its contents. Her expression was flat when she let me know she had looked. It was a telling look justifying my decision to keep the gift secret.

I have had the blue bag now for eight years and have never looked inside. Someday I will burn it as an offering for honoring the unknown.

Long live hostess gifts and re-gifting.

hostess gifts

onto the future

I sent my colleagues the following.

dear friends…

August 1st will be my last day at Microsoft, thanks for being a part of the journey.

Leaps of faith

At 17 I ran away from a prep school in PA to NYC. I landed on the doorstep of my best friend; luckily she was home. While I had no particular plan after my arrival I knew there were a million fantastic possibilities. It was 1976 and I was not disappointed.

Skip forward 35 years…

After 21 years at Microsoft I find myself taking another leap of faith, moving on with no particular plan and another million fantastic possibilities.

Lasting impressions

Wow. Vietnamese president Triết shook my hand on the first presidential visit to the US since the Vietnam War. President Hu Jintao bowed to me, twice. Nancy Pelosi thanked me. And there was the time I tried to get BillG to wear a propeller beany hat on stage.

You have also left a lasting impression.

You have shaped and rocked my world. Wow.

Mama Microsoft

While I still have the floor, I ask that you continue to do good work and consider the moral imperative in everything you do. Make choices that benefit humanity.

And for crying out loud, don’t postpone pleasure!

I am eternally grateful.

oxo- flora

p.s. – If you want more stories… buy me a cocktail (or make my next mortgage payment)


onto the future

inno day 2007

Here with Manuel Pinho, Portugal's Minister of Economy and Innovation, and other Microsoft folks. I'm the one pointing.
Here with Manuel Pinho, Portugal’s Minister of Economy and Innovation, and other Microsoft folks. I’m the one pointing.

Thinking about the past…Innovation Day 2007- Living and building Europe’s digital future

Microsoft’s Innovation Day in 2007 was set in Brussels.  The event demonstrated leadership and innovation to the EU public sector and the media. The focus was on consumer safety and privacy including child safety, fraud, and game addiction. I presented 3 team vision demos and had conversations with key leaders around these topics. Scenarios presented were:

Sharing Personal Info safely
A demonstration of an experience hiring a babysitter that showed how a method of reciprocation allowed participants to safely share personal information while protecting their privacy.

Keeping our Children on Track
A prototype tablet designed for a child that had parental controls and content management built in. Scenarios showed touched on: safe communications, homework, and a game for which children performed chores in order to earn credits for technology play.

Browsing based on preferences and more
Through an online entertainment guide, we displayed content populated by a combination of filters including your preferences, tracking your history and organizations you may subscribe to. The content included: recommendations from the school based on the current curriculum, trips taken and planned, shows based on actors we’ve watched…

It was a fun trip, although spending 3 days in Europe is never enough…

inno day 2007

proud moment

4/18/2006 we had the honor of hosting President Hu Jintao at Microsoft. The experience was amazing, especially to work with the Chinese national employees. They worked tirelessly to make the visit perfect. They genuinely cared to give their president the very best experience. Their sense of patriotism was celebratory and refreshing. I still feel high when I think of the event.

President Hu Jintao with his wife Liu Yongqing. I'm back in the shadows.
President Hu Jintao with his wife Liu Yongqing. I’m back in the shadows.

We designed a 9 minute tour that introduced the Microsoft Home. We personalized the space including vision prototypes displaying photos of places he had lived throughout his life. He was appreciative of the gesture. The tour was presented by Tim Chen, head of our Chinese efforts at the time. At one point I presented a clothing scenario in the teenagers’ closet as Tim translated. The President bowed to me, twice.

It was my job to make sure the Home visit went smoothly. I purchased a stop watch for our rehearsals to make sure we hit our marks. It’s now attached to my bulletin board as a memento. The tour ended up taking 14 minutes, the president was very interested. During the visit one of his body guards, a woman, (provided by the CIA?) ran defense keeping the press at bay. She bounced back and forth with her arms out stretched creating a barrier all the while manically chewing gum. I wanted to giggle.

Microsoft was the first place President Hu Jintao came to on his US visit.


Speaking of Presidential first visits, in the summer of 2007 we had Vietnamese President Nguyen Minh Triết on the first presidential visit to the US since the Vietnam War in 1975. Wow. While it was an honor to also be a part of that visit, it didn’t have the same elevated effect.

proud moment