How I left the Corporate World and Embraced the Unknown

Jumping into a forest waterfall in Vietnam during a round-the-world sabbatical in 2001–2002
Jumping into a forest waterfall in Vietnam during a round-the-world sabbatical in 2001–2002
Jumping into a forest waterfall in Vietnam during a round-the-world sabbatical in 2001–2002

In summer 2019, I chose to leave my high status, impactful, and financially lucrative job as a design leader at Facebook. I was on a search for something more meaningful, more fulfilling, and that quest eventually led me to leadership coaching. This is the story of how I designed my life to be successful by my terms.

I loved my job at Facebook. I gained deep satisfaction from supporting the immediate designers on my team as well as providing inspiration, creative North Stars, and engaging collaboration with my partners in engineering, product, and content partnerships. Working on the innovation side of video products, I deeply believed in the mission, that we were seeking to add more meaning in people’s lives by enabling connections with friends & family over a shared love of shows or bonding with strangers over entertainment topics that friends can’t relate to. If you’re looking for some fantastic and free shows, scroll down for recommendations in the appendix.

Yet it wasn’t enough.

Many people think that working for Facebook is a dream job. And it was my dream job when I first joined. I had followed the traditional path of success. My tiger mom helped form my path from valedictorian to a Stanford B.S. degree, and I forged my own way through 20+ years of design jobs in startups, design agencies, and large companies. I was lucky to have this wealth of experience in so many industries and to work with some of the smartest people in the world. I had also worked hard — 50–70 hours each week in corporations for other people for over 20 years. At Facebook, I was able to build completely new video products and create shows filled with diverse voices and new forms of interactivity. Each day I was exhilarated. And at the same time I was tired. I was running at 110%, jumping from crucial meeting to crucial meeting, making important decisions, engaging in fierce conversations to build the best products, and always multi-tasking, being always-on, all the time. The to-do list had to be painfully prioritized because it would never get done. At the same time, I was holding the mental weight of leading a team. I needed to believe, so that I could help hold the inspiration and belief that the work we do matters. My energy was lagging. My time was lagging. And everything was compounded with a daily 3-hour commute. It was never enough. I was never enough. Work was conflicting with my values, with what I held to be most important in life. It felt like I was giving up the best hours of my days in service to something else, to someone else’s vision and purpose.

Something had to change. So I quit.

I left the security of Facebook. The company makes it hard to leave — you are surrounded by ridiculously smart people, you make products that impact 2.3 billion people all around the world, you are cocooned in an idyllic place where growth & learning is emphasized, and the food is seriously delicious. When your work with one team is coming to a close, you are encouraged to find another team within the broad world of Facebook, Instagram, WhatsApp, or Oculus. When I was ready to leave Video after three years, I couldn’t bring the energy/passion/leadership to join another team and be truly excited and inspirational to a new cohort of product designers. So I left Facebook.

Saying “Yes” to leadership coaching.

I have been coaching designers on my team for 10+ years and Facebook gave me the training and skills to coach female technologists throughout the company. After I left Facebook, I took my first coaching workshop through the Co-active Training Institute. I figured that it would help me be a better leader, a better listener and that it would help me in my next design leadership job. That wasn’t the message that the universe had for me. Even though I fought it, kicking and screaming (more to come in a future blog post), four weeks and three workshops later, I decided to take a career swerve and establish my own business as a leadership coach.

After receiving extensive coaching on what I really wanted, this is what I learned:

1. Permission to dream

When I say “Yes” to leadership coaching, I continue to be a designer. My 20+ years in product design had already equipped me in helping product teams dream the future of automotive, of mobile devices, of television, of interactive entertainment. I simply needed help to give myself the permission to dream.

Similar to design, once a dream has been identified, coaching helps provide the operational execution and structures to help a client get from a place of now, where she may be stuck with self-doubt or hesitations, to a new and powerful place of experiencing the dream.

2. Honor My Values

  • Adventure. I grew up moving to a different country every 3–4 years. I adore change, taking risks, and experiencing new things. This has been a core value for me ever since I was a little girl.
  • Challenge. This is closely related to change and experiencing new things. Change is often challenging, bringing you out of a comfort zone. I like hard things. I am competitive and driven. I continually challenge myself to be better.
  • Transparency. I strongly value being direct, honest, and open. Transparency honors the way I see another person and when done with caring intention builds trust and mutual benefit. Feedback is a gift.
  • Family. Being a mom is the hardest and most rewarding job that I had ever done. I carry over this mama bear protectiveness to people within my circle — my design team, my friends, my clients. Family means a sense of shared responsibility, of being autonomous and also better together. I aspire to provide my family with unconditional love and support.
  • Dance in the Moment. Co-active coaching felt like home when I saw Dance in the Moment as a core foundation of the Co-Active Model. As a life long type-A planner, I’m good at doing things — strategizing the future and creating operational structures to meet these goals. Yet simply engaging in a model of planning & to-do lists left me missing a sense of fulfillment and satisfaction. I’m far less skilled at being present, savoring the moment, being funny, being messy, making mistakes and forgiving myself, and surrendering in to the freedom of dancing in the moment. Yet it’s those moments of Being between the Doing that give me contentment.

Truly honing into the values that matter to me made me realize that while my corporate career let me honor Adventure, Challenge, and Transparency; some aspects of Facebook, including the daily 3-hour commute was at the expense of Family. It was also challenging to honor Dance in the Moment while working for high impact tech companies and startups where how fast & well you build products are the main metrics of success. Clarifying my values was a giant step to help me embrace leadership coaching.

3. Measure Energy & Authenticity

How authentic am I? How am I honoring my values?

How much energy or joy am I getting from what I do each day?

I realized that while I was both exhilarated and drained after leading design sprints or leadership workshops, after conducting 1–1 coaching sessions, I was buzzing with energy and resonance from the conversations. My clients were gaining new insights and realizations about their leadership styles and how to claim that leadership for themselves. It felt truly magical and special. And I was being authentically myself — being lovingly challenging and transparent while unconditionally supporting my client.

Damn, it feels good. And I was hooked.

4. Trust the Process

I’ve learned enough through years of designing products that Trust the Process always works. There is a familiar rhythm with going deep into research to understand what people problems you’re solving for. There is a rhythm to sketching out a wide variety of ideas & solutions. To brainstorm widely to get ideas (diverge) and then to select a few (converge) that will be experimented upon. This is a typical design process that the Stanford d.school shares. And I also know that it feels shitty in the middle. It feels hard and unfamiliar and that you’ll never come up with the beautiful conceptual North Star. And I always know and tell my teams that it’s a simple replicable design process. Trust the Process and you will get to the right design.

In coaching, I tell myself the same thing. Try the new tools, try the new imaginings and looking within for different Allies and Leaders and Sabotoers. Play games. Embrace the “woo woo.” It’s about allowing myself to marinate in the fear and discomfort. Fear is part of the process. And fear is the pre-cursor to trying to change and to be brave. Trust the Process.

Thank you for reading to the end and taking this journey with me. Thank you to Leland and Amara for graciously reading drafts of this post.

About

I grew up in seven countries on three continents and am settled in San Francisco as my home base. I spend my time parenting two adventurous girls, obsessively reading, and paddling out for the next wave.

If you’re curious about coaching and how it could unblock your life, learn more about what I do.

Appendix of Links & References

Written by

Leadership coach & champion of difficult people; designer of human experiences; ex-Facebook; surfer, traveller, mom; tuttitaygerly.com

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