Three Big Things I Wish I Knew

Before Leaving My Career To Pursue My Dream

Two years ago today was my final day working at Google. After 12 years as a Googler, I “graduated” to go out into the big wide world and create something new of my very own.

I couldn’t find anyone who did what I was doing: leaving a dream job as a single mom with no financial support to build a business in a new industry. Not knowing what to expect is a huge part of what prevents us from making changes: the uncertainty isn’t worth the risk.

To be honest, I was terrified. For a long time, my fear kept me stuck and stopped me from making the move. But after awhile, my dream became bigger than my fear.

I’ve learned a lot these past two years, and I wouldn’t change a second of it. I am happier and more fulfilled than I’ve ever been in my life. There are a few things I wish I’d been more prepared for, so I hope by sharing them, they can help you.

Everything takes longer than you think. Be patient.

Before leaving, I made a deal with myself I would make a run for my dreams for 6 months, giving it my all. If it didn’t work out, I reasoned, I would go back to corporate knowing I’d at least given it a shot.

I had never owned a business, never tried to work while raising kids without childcare, and was establishing myself in an entirely new industry.

In six months, I was barely figuring out how to stand on my own two feet, much less feeling like I could have run hard at my dreams and given them my all.

If I gave up then, I would have missed out on all the seeds I had been planting which started to take root and grow soon after. Seven months after leaving, I was invited to return to Google as a consultant to lead an authenticity workshop. A year after leaving, my story was featured in Forbes. And, later this week, I'm speaking at Google again (everything comes full circle!).

When we’re experts at something, we forget how steep the learning curve is and how daunting it is to be at the very bottom. Everything takes longer than we think, but that doesn’t mean we’re doing it wrong. It just means we’re learning something entirely new.

Don’t put a timeline on your dreams; they're worth all the time it takes to bring them to life.

Expect shock and detox. Be patient.

When I left, I planned on taking December to relax and have fun doing nothing all day, then get busy building in January.

It was anything but fun and relaxing.

Without a routine or KPIs or work to show for myself, I didn’t know how to move through my day, measure my contributions or show my value. The worst shock of all, though, was without being able to say I worked at Google, I didn’t know who to say I was.

I had no idea how much my identity and self-worth were wrapped up in what I did and where I worked.

Anytime we experience a huge change, we feel lost and anxious without the normalcy we’ve come to expect and find safety in. Thankfully, we do eventually adjust and adapt but we have to have patience and kindness with ourselves in the meantime.

Don’t rush through your detox. You’re letting go of one identity and making room for another; that’s important.

Insecurity skyrockets when you’re out of your comfort zone. Be patient.

I thought I had worked through my perfectionism and Imposter Syndrome insecurities before leaving Google. Wrong. Instead, I was just living inside my comfort zone so they went dormant. Once I left the safety of the well-worn path I’d been on my entire life, all of my insecurities turned up to 11.

Insecurities are born out of our fears which are intended to protect us. When we leave the comfort zone where we feel safe, fear heightens and insecurities turn up. In evolutionary terms, they’re screaming to get back in the cave and away from dangers lurking in the dark. Mine practically had megaphones.

Any time we expand ourselves and go out into the world in a new and different way, it feels like a risk to our survival. Fear does not mean we need to turn around and run back for cover, though.

We can learn how to have fear without letting fear have us.

Don’t see fear as a ‘Stop’ sign; it actually means you’re headed in the right direction. Go slow, but keep going. 

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After graduating from Google, I began saying I was practicing the Art of Undoing, and these last two years have been like a Master’s degree in becoming undone. I have been undoing layers of who I was and who I thought I should be, which were holding me back and slowing me down. By practicing the Art of Undoing, I learned how to let go and be, and especially, to be patient.

I realize now I needed every single hardship I experienced because what we are intended to teach, we must first learn. Whatever universe lessons we go through are preparing us for what is to come and who we are to become.

I now teach The Art of Undoing because I know that the more you undo, the more you become.

Wherever you are in your journey, I hope these lessons are useful. Just know this: no matter what, you are not doing it wrong. You just need to start undoing.

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Your turn: If you've made the leap, what were your biggest lessons? What do you wish you'd known earlier? Your comment might make all the difference to someone else!

2 thoughts on “Three Big Things I Wish I Knew Before Leaving My Career”

  1. Beautiful! I remember when you told me you were leaving and.. I have to say I was a bit timid to share what you’re sharing now. It’s scary enough without authenticating how hard it will be in the course of trying to encourage.

    I’d only add that anyone looking to start a business shouldn’t feel inadequate if they need help or support from others. Be an expert at what they know and surround themselves with others who can help with their weaknesses.

    It’s ok not to know how to do something. It’s not ok to fail doing it because they didn’t seek help.

    Thank you for your continued courage and leadership!

    1. Honestly, even if you told me all the things, I’m not sure I would have listened. I likely would have believed I was the special unicorn who wouldn’t go through it.

      And YES to asking for and accepting help! One of the hardest things for me, and one I have to remind myself to do constantly.

      Thank you!!!

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