Trista Taylor, Founder and CEO at Regroup

I walked away from a dream job. Each year, 2 million people apply to work at Google. My spouse always told me, “you’ll never leave, they give you free pancakes.” Yes, the pancakes there are amazing, but what made it really hard to leave were the amazing people, the incredible opportunity to make a difference in the world, and the golden handcuffs. So, why did I do it? And, how?

I started at Google in 2007 when the Seattle office was just 100 people and Google was just 17,400 people (now, it’s over 100K people). It was before Chrome, Android, Hangouts, Cloud, or Alphabet. We carried blackberries. The whole Seattle/Kirkland office went on an annual ski trip. There were bean bags, lava lamps, and free t-shirts galore. It felt like the wild-west and anything was possible. I loved it!

Over the next decade, I had the privilege to help teams work better together—to improve things like team cohesion, strategy, clarity, team culture, and processes. I built a scalable platform called TeamDev, which enabled all teams to gain insight and take action to improve team dynamics along with a global community of 100+ internal volunteers to consult and facilitate customized team interventions. This effort operationalized the team effectiveness research known as Project Aristotle. During this time, I had a ton of meaning, purpose, and autonomy.

It was around 2018 when I started getting an itch to leave—to take my show on the road and apply my experience outside of Google. But, Google was part of my identity and I was scared to go out on my own. So, I stayed. I took on a couple of different internal roles—working in the core g2g team (Google’s peer-to-peer learning network), and finally, something completely different, an HRBP in the Cloud organization. The more I changed roles, the more I found myself drifting from my calling and giving up the autonomy and purpose that made work worth doing. That’s when I really had to ask myself—what am I doing?

So, I did some soul-searching. I reflected on my own strengths and interests and journaled about what I wanted in the next 5 years. I met with a career coach about what it would mean for me to leave Google—the loss of identity and relationships. I attended Venture Out events to meet other founders to see what my life might be like after venturing out and talked with others I respected who had left Google. I realized it was time to strike out on my own.

When I gave my two weeks notice, I felt so strange. I had worked at Google for 11 years! I felt a huge sense of pride and identity with Google. It felt like saying goodbye to family. What was going to be on the other side of those two weeks? If not a Googler, what would my new identity be?

My intention was to build a solo consulting practice to help managers improve team dynamics. However, I didn’t feel motivated to build that business. I would find anything else to do around the house—I spent two weeks with my mother-in-law Mari-Kondo-ing my house. Then, after 6 months, I got an idea to build a scalable platform to help managers improve team effectiveness. This idea kept me up at night and just would not go away.

So, what am I doing now?

I’m the Founder and CEO of Regroup, where we help managers improve team dynamics. Our mission is to make every team a great place to work. We’re piloting our initial offering with teams, right now! Learn more at Regroup.co.

Looking back, I wish I had left earlier. However, it takes time to be ready. I’m so happy with my decision to leave. I’m feeling more motivated and energized by the opportunity to make all teams a great place to work and to build a team and a company to support that mission. Once again, I have meaning, purpose, and autonomy. Sure, I miss the comforts of Google (I’m making my own lunches and I miss the security of my paycheck), but it feels so good to be uncomfortably excited in this new journey.

Some advice for other founders looking to make the leap:

1. Look before you leap, but don’t look for too long. I had no intention of starting a startup. I only started reading Lean Startup and other startup resources a few months ago. While I wish I had read up on all these resources and formed a clear plan before I left Google, sometimes the plan evolves over time and there’s no “right time” to leave. And, if you stay in your internal role too long, all the comforts and handcuffs will make it even more difficult to leave.
2. Be sure your life partner is supportive. I was really fortunate that my life partner was supportive of me leaving my job and believes in the possibility of Regroup. We have two young daughters (ages 5 and 7) and we are living on his salary right now. So for us, it was a joint decision for me to found Regroup, and it would not be possible without his support. If you don’t have a life partner, just make sure you have a personal runway to get the business going.
3. Be clear about your goals. Why do you want to venture out? What need will it fill? What will success mean to you, personally? The clearer you can be about your motivations the better decisions you’ll make and the more you’ll be able to gauge if you’re on the right path to success. Also, make sure you’re super passionate about the problem you’re solving.
4. Be the person in the arena and dare greatly. Thomas Roosevelt has a speech that Brene Brown often quotes: “It’s not the critic who counts…. The credit belongs to the [person] who is actually in the arena, whose face is marred by dust and sweat and blood…if [they] fail, at least [they] fail while daring greatly, so that [their] place shall never be with those cold and timid souls who neither know victory nor defeat.” For me, it was time to dare greatly. Being in the arena is exciting and terrifying. I feel alive. There will be ups and downs, but when you are daring greatly in the arena, you live life without regrets.
5. Connect with others who know more than you do. I’ve never started a company before and I have so much to learn. Every day I’m learning—from other founders, potential customers, former Googlers, investors, and others I get connected with. People want to share their knowledge, insights, learnings, and they want to be helpful. So, learn from others and be generous in return.

If you feel the pull to be in the arena as an entrepreneur, you might be ready to venture out. Deciding this life change can feel scary and overwhelming, but you’re not alone. There are amazing communities of people who’ve walked this road before who are supportive and happy to help.

Curious to learn more about Regroup? Learn how we help teams improve things like psychological safety and clarity at www.regroup.co.