Ex-Googler, Current Beginner: Reflections on Life After Corporate

I’m a bit incredulous that a year has already passed since I left my job as Director of Program Management at Google. It wasn’t a decision that I came to lightly (details on why I left), but I was taking a chance and betting on myself, not just for short-term escape, but to transform my work to truly reflect what matters most to me and apply the knowledge, skills, and experience that I’ve gained over the course of my career to a new purpose. 

From that perspective, I honestly have no regrets. I feel joy and pride at how far I’ve come and excitement about the future. At the same time, moving from a world of high-level authority and status as an “expert” to the humbling and often messy role of self-employed beginner has been a profound identity shift for me.

The Battleground (in my Mind)

I’ll start with the real talk and address the most challenging part of this transition: the mental and emotional rollercoaster.

Fear of Failure and Financial Insecurity 

This life is not for the faint of heart; I am constantly managing and sometimes battling looming fear and anxiety about financial security. Once or twice a week, I have moments of doubt about my choices. 

Most recently, I examined my worst fears more closely and decided not to worry yet, because I am still in the ramp up phase, and I have multiple layers of contingency plans and enough runway to keep my family from becoming destitute for at least a couple more years if both my husband and I completely fail in our businesses. Plus, I’ve rekindled my relationship with my old friends Nordstrom Rack and TJ Maxx.

Lesson Learned: The stoic philosopher Seneca said, “We are more often frightened than hurt; and we suffer more from imagination than in reality.” Fear often lives in the abstract. By scrutinizing my fears and having contingency plans, I am able to move from being paralyzed by anxiety to taking a calculated risk. After all, you can’t control most outcomes, but you can be prepared.

Being a Beginner, Over and Over 

This transition also requires facing the discomfort of learning new skills and having to experience Conscious Incompetence at every turn. It’s a blow to the ego when I can’t perform a task well, and that I’m making mistakes, usually in front of other people (like fumbling through hands-on assists during large yoga classes in the early days of my internship). 

But it also helps to recognize that I am in a normal and necessary stage of the learning process, and this stage, even the negative feelings, gives me fuel to keep learning, to identify where I have opportunities to improve, and to persist in my practice. And when I persevere, I’ve witnessed myself progressing to Conscious Competence and in some cases, the nirvana, Unconscious Competence where the skill is internalized and starts to feel intuitive. And sometimes I’ve had to brush off old skills that have been dormant and gotten dusty, going back to Conscious Competence, where I need to concentrate harder and practice again.

Lesson Learned: High-achievers are used to being polished and competent. Embracing the discomfort and messiness of the beginner stage is hard, but it’s temporary and necessary to eventually be great at something different.

Unclear Path

When I embark on a new journey or challenge, I need a vision of where I’m going in order to see my path forward. That can take a lot of exploration, trial and error, living in uncertainty to understand what the potential destination is, and then the roads that feel right for me. I’ll share more below about how I conduct experiments to test out potential paths and get more clarity on what I want and don’t want. As I’m experimenting, I find some of the yeses and nos are very clear, but sometimes with the things in the middle it’s hard to discern if the resistance I feel is driven by fear (“This is uncomfortable but it’s leading towards something that I still want.”) or a signal that this is not the road for me (“This feels yucky!”). All I can do is keep going until the answer emerges.

The Power of Vision

One of my key observations is that envisioning what I want and writing it down has a powerful, almost magical effect. As I was planning my exit early last year, I laid out a few goals for 2025. I achieved every single one of my goals–or at least my part, since some of them require some waiting, which has also been a useful practice in patience and allowing things to unfold in their time.

Lesson Learned: Your vision acts like a magnet for what you want. I achieved 100% of the goals I committed to writing and very little of the ones that remained vague in my mind. Vision doesn’t just give you clarity about your destination; it acts as a filter for every opportunity that comes your way.

Inspiration

The Winter Olympics served as a timely inspiration to me at a time when my “results” felt small and I was battling fear and anxiety about our financial security. After watching stories of these young Olympians, I noticed a repeating theme where they watched the Olympics with their families as children and were inspired to start learning a new sport. Their passion fueled continued practice and they became more and more skilled. Maybe they needed to be obsessed. They stayed committed until they reached national recognition, and then made it to the Olympics. 

This was a much-needed reminder that I’m still in the relatively early stages of trying to build a post-corporate career portfolio, and it’s a long game. My goal is not to make as much money as possible in the short term, and I appreciate how fortunate I am to be in this position. Some of the timelines I have set for myself to achieve outcomes are arbitrary. I’ve done a ton of networking across a wide variety of communities and professions, gained experiences, developed new skills, and expanded my perspective. In the middle of that, I’ve also gotten a lot done and have expanded my reach through coaching, writing, and teaching yoga. 

I’ve planted a lot of seeds, but I can’t see what is happening below the surface–what will take root and sprout, and what is already dead? In my backyard, we’ve had plants completely disappear above ground after being eaten by moles and then come back a year or two later after plenty of rain and sunshine. Progress can be excruciatingly slow, and is beyond my control.

Discovery and Exploration

One of the best things about venturing out into the world outside of the tech industry and corporate world is being exposed to worlds that I didn’t even know existed before, simply because I now have the time and energy. Here are some things that stand out for me.

I spent several months going down a rabbit hole learning about real estate investments and found the world of alternative investments, passive income beyond traditional stocks, and self-directed IRAs. We also seriously considered buying a franchise business, but that’s hardly passive and we ultimately realized it wasn’t right for us.

Active and intentional networking has led to collaboration, leads, referrals, friendships, and a lot of new ideas from hearing other people’s stories. Plus, I’ve enjoyed meeting and chatting with people from all over the world.

There are a lot of people out and about during the day. I’m intrigued by how full the 9 am yoga classes are. TJ Maxx always seems to be busy. I know that some people have flexible work schedules, and some are not working for a variety of reasons. But I never feel lonely or lack people to connect with during the day.

I’ve noticed many others are leaving their longtime jobs for a career break or to pursue something different. Some of this is due to layoffs and voluntary exit programs, but there are a growing number of people like me who have just decided they’re ready for something else. Some of it may be due to age (Hello, fellow GenX-ers!); I’m at a place in life where I don’t feel the need to hustle in the same way anymore. I’m comfortable with who I am and don’t care what other people think about me nearly as much as I used to.

Lesson Learned: Connecting with others and being in new spaces has supported my learning and helped me to feel less alone. Growth and change don't just happen from the inside out; we also change from the outside in as we converse with others and gain perspectives and exposure to new contexts, communities, systems, structures, and collective energy.

A New Definition of Success and Confidence

I love what I do and I’m good at it. Right now, that’s executive and leadership coaching and teaching and giving hands-on assists in yoga classes. I can say this without worrying that I’m bragging: it’s not because I’m smart and talented. My abilities are the result of the years I’ve spent building and honing my skills and craft. I’ve put in hundreds of hours, continuing to show up day after day despite feeling uncomfortable and incompetent time and time again.

There is so much for me to be proud of. I am transforming myself. I have the invaluable perspective that comes from having lived through repeating cycles over several years. I’ve seen things; I’ve suffered losses and unexpected changes.

I have a new sense of identity that gives me the confidence to stick with doing things my way, even if it takes longer. I have a very different definition of success than I might have before, and I don’t define myself by how much money I make or other quantitative measures.

Grieving the Past and Finding Gratitude

And yet, even with all of this pride and transformation, I realized that I still needed to mourn the loss of my past life. I had unresolved emotions that emerged at the beginning of this year. With the loss of Google income, we’re not going on big vacations (last year was an exception with things already planned, deliberate choice not to make major changes). I had strange feelings come up when I heard about other people’s trips, but it wasn’t jealousy or envy. 

Through journaling and reflection, I came to recognize the feeling as a normal part of a grieving process. Even if I left because I wanted to and knew it was the right choice–not unlike when I ended my first marriage–it felt like a part of me was ripped away. And with time, I got used to it, and life had something much better in store for me, which I didn’t expect or even let myself want, and it came fast. I know the same is true for my current situation. This insight allowed me to appreciate that I already have enough and feel a deep sense of gratitude for my life experiences, friends, family, and good fortune.

My Experiments

I like to approach personal and professional growth with a version of the scientific method that I learned in 7th grade science class that centers on running low-stakes experiments in order to try out new skills and behaviors. The goal is to start doing and experiencing so that you can learn what works and what doesn’t, what feels right and what feels off. It’s a great way to practice growth mindset - what you get from experimenting is data and information to inform how to best move forward. 

A lot of times we want to do all of the analysis upfront and feel a sense of control to be able to get the outcome we want, but what often happens is that we become paralyzed by fear of failure and nothing actually changes. When you take an experimental approach, you are simply trying something out without making a commitment or decision. You may have some initial observations and a hypothesis, but you still have the option to stop an experience or take it in a different direction as you learn more.

I already discussed my approach of planting seeds; experimentation is like throwing a handful of seeds across a vast area to see what takes root. This helped me to learn what soil is fertile, where I enjoy nurturing and watering, and also that I could let go of ideas that feel like dead ends, at least for now (worth noting that if you have a viable seed, some can take longer to sprout than others).

What took root for me:

• Joining the Board of Directors of the Asian Women Coaching Collective and am learning about running a nonprofit org and the BoD experience

• Coaching my private clients and contracting with a few online coaching platforms with clients across a wide range of job functions, industries, and career phases; logging enough coaching hours to exceed my 500-hour goal by the end of last year

• Joining the International Coaching Federation (ICF), meeting other coaches and learning through San Francisco Bay Area Chapter events and the global Converge conference

• Applying for my Professional Certified Coach (PCC) credential with the International Coaching Federation (and patiently waiting for my exam results in April)

• Getting our finances in order and making some alternative investments (senior living, debt funds, mineral rights, and land banking)

• Substitute teaching yoga classes, learning hands-on assists, and now teaching two weekly classes at a local studio

• Starting a Health and Wellness Coaching Certification program

• Reducing discretionary spending, ditching the meal kits to cook dinner from scratch, drinking less alcohol, and losing some of the pesky perimenopause weight

• Reading at least one book every couple of weeks

Things I’m still unsure about:

• Exploring my creative side through learning to play the harmonium and dabbling in visual art

• Developing workshops and group coaching programs, some with collaborators, and getting a certificate in the Art & Science of Course Creation 

Dead ends (at least for now)

• Voice lessons and Community Choir

• Franchising

• Python crash course and applying for Code in Place TA position

Lesson Learned: Treating the results of your experiments like data instead of a measurement of your worth is freeing. When you hit a dead-end, the failure is simply a useful data point that helps you narrow your focus toward the paths that actually work for you.

As I said earlier, there have been (and still are) several areas where my vision just wasn’t there yet, or it was still murky, and I don’t have concrete results or a sense of being done because there is no definition of what done should look like. But I’ve learned to be okay with my life not being 100% solved. Solving wasn’t the point, and I am having fun!