Jaime Waydo — Taking Care of Yourself First, Fearlessly Owning Your Desires, Speaking Your Truth and Designing Systems to Support You

In Episode 41, Brett interviews Jaime Waydo, Chief Technology Officer for Cavnue. Previously, Jaime led systems engineering at Waymo, Google’s Self Driving Car program, and collaborated with NASA on the Mars Rover Curiosity.

Jaime came from a mindset passed down generationally that, especially as a woman, it was important to place everyone’s needs — children, spouse, employees — before her own. She quickly realized that this way of being led her to chronically running on empty, which neither benefited her nor her community. She pivoted to putting herself first: speaking her needs vulnerably, organizing systems to support her and designing a schedule that worked for her, transforming her work culture and her home life, while giving her the energy she needed to live life on her terms.

Tune in to this episode to find out how she made it all happen.

“Let’s just look at this like a patient on the table. What are the symptoms? And then, what’s the next step in treatment? And so, solving problems like that and not worrying about whose fault is something, I think is a really good way to keep the shame from cropping up in people and then they can stay much more in the problem-solving mode.”

What we discuss in Episode 40:

1:41   Why it’s okay and important to be selfish.

6:06   How being a chronic people pleaser can result in "chameleon leadership” and create anxiety within a team.

9:23   Generational expectations placed on women to constantly give without having support systems to replenish their own energy.

11:13   The turning point where Jaime realized that prioritizing herself would also allow her to better serve others.

16:00   How Jaime showing up vulnerably allowed her to improve team culture and cohesion during the pandemic.

20:00  Jaime’s techniques for speaking her truth within the context of challenging interpersonal dynamics.

26:26   How Jaime brought more peace and joy into her household by relating authentically with her children.

33:28   Shame as a root emotion behind micromanaging and people-pleasing behavior.

Follow us on Instagram at @artofaccomplishment to learn more about our guests and share your own experiences.

Transcript

Episode intro:

Let’s just look at this like a patient on the table. What are the symptoms? Then, what’s the next step in treatment? And so, solving problems like that and not worrying about whose fault is something is I think just a really good way to keep the shame from cropping up in people, and then they can stay much more in the problem-solving mode.

Welcome to the Art of Accomplishment where we explore how deepening connection with ourselves, and others leads to creating the life we want with enjoyment and ease.

Brett: All right, everybody, welcome back. Today I am speaking with Jaime Waydo. Jaime is the CTO of, fuck. Let me do that one more time.

Jaime: No, keep that in.

Brett: Okay, we are keeping it. Jaime is the CTO of Cavnue. Previously you were at Apple. You were at Waymo. You worked on the Mars Curiosity Rover, and now you are working on autonomous driving.

Jaime: Yeah, I have spent about a decade working in autonomous driving and really trying to realize my passion of making mobility available to everybody no matter if they can drive or not.

Brett: Nice. In our pre-call, just now before I started and completely botched that intro, you were starting to tell me about something that you have learned through your career, through all of these different businesses, and something that really just applies to your life in general. Can you tell us what that is?

Jaime: Yeah, I am struggling with the words a little bit on it. I don’t like the word ‘selfish’, but I am going to use it for a minute because I think it feels right. That is that it is actually okay and important to be selfish, to really go into your self and own your wants, speak your truths, and think about what you need to be successful because that will help everybody else be successful. I think especially as a woman, we are really engrained to think about making sure everybody else is okay, making sure our kids are okay, our spouse is okay, our family members are okay, our employees are okay.

We end up in this cycle of trying to help and make sure everybody else is okay, and we are just empty. What I actually realized about two years ago was at work, and I was like they are paying me because they want me to be successful and maybe I should think pretty hard about what the systems are that I need to be successful and how I set this up in a way that works for me. That’s what I would love to talk about today.

Brett: Great. How did this end up becoming a thing for you? What was your life like? What were the factors that led up to this recognition?

Jaime: Just exhausted. I am very high EQ, and so I can look at people and I can usually read them. When you are high EQ and you are working on trying to make everybody okay, it is very emotionally exhausting. I just had nothing left in my cup. I think back, and my oldest is now 11 but when he was nine months old, I was driving to a yoga class. It was the first time I had left the house without the baby, nine months old. I sat in the car in the parking lot just crying because I was like I don’t even know how to find time to take a shower. My husband took the baby, and I could go to this yoga class. I just had nothing in me to even walk into this class and start working out again. That’s when the seed started being planted. How can I be the mom I want to be when it is all about making this nine-month-old human not die today?

Looking back, what I should have done is say hey honey or call my sister, ask for friends, send him to daycare for a few hours, but I just was putting all on myself that I needed to put everything for me into him, which ended up with me being a crying mess in a parking lot and probably not showing up happy and ready to play on the floor when the baby was ready. That’s where it started.

Brett: It sounds like that would be an easy thing to get yourself caught up in because it is your baby. You care about your baby. You want your baby not to die when you look away for 15 minutes. It would be very easy to think that it is also your baby and your responsibility. Your sister didn’t have your baby or friends didn’t have your baby. It’s not their job. To think that you have to take it all on yourself and not even ask makes it so that you are not able to take as good care of the baby because you are not taking care of yourself.

Jaime: Exactly. Thinking very critically about how I take care of me so that I can take care of whatever else it is that is my responsibility whether it is at home or at work. This started manifesting at work. I was coached very early on. I became a people manager when I was at the Google self-driving car program, and I was coached very early on that great managers change their style for every employee. They meet their employee where they are, and then work their style to speak to that person. I was like great, I am going to be so good at this.

I started what I call now chameleon leadership. I would show up with every person differently, but I got this feedback at Apple when I was there. Somebody was like it looks like you are just so inconsistent. People are very uncertain about how they need to show up for you because you are different in every room you are in. I actually think one of the arts about being a leader is that people kind of know and they can channel you so that you don’t have to be in every room and every decision. This thing I was doing that I thought was so good of taking care of everybody else and meeting their needs and not being clear about my wants and what I needed was actually showing up as a thing that made people fearful and uncertain how to interact with me.

Brett: It sounds like there is a nuance to be found there between meeting people where they are and leaving yourself to be where they are with them and not actually being present and not showing up in the relationship in your truth.

Jaime: Yeah, exactly. Joe talks about this a lot as you can hold space for people, but you have to stay in yourself. You have to stay centered in your knowing, your truth, your wants, and I think I was just going completely into the other person and trying to feed them what they needed. It actually wasn’t working for anybody, so I made some pretty big changes.

Brett: How did that relate to what you were describing as you didn’t even want to use the word, but whatever it attaches to as selfish?

Jaime: To me, at first it was just like that’s just selfish. A leader or a parent that comes in and is like no, I am going to go off and play golf today or my meetings are creative meetings in the morning because that’s when I am creative, and they are one-on-ones in the afternoon because that’s when I am ready to just click through those personal conversations. At first, I was like that’s a very selfish thing to do, and then I started looking at leaders that I really respect and how they run their schedules, how they run their days, how they set up the systems and the processes that make them work. I realized that every leader does it differently. I was like that’s interesting.

Then I started looking and I was like oh, they are being paid to be successful. They are setting up systems that make themselves successful. That’s what they are expecting me to do, too. Everybody is sitting around and waiting and going like you are the leader. Why don’t you tell us what you want? It is not actually selfish, but it feels like it in the moment when you are just like this is what I want, this is what I need, and we are going to do it this way.

Brett: What do you think taught you that visceral feeling of shame or whatever it is that comes up when you feel that fear of being selfish, or you feel that taking care of yourself is self-centered or selfish? Where do you think that comes from?

Jaime: I think some of it is in gender, for me at least. Growing up in a small community where the matriarchs of the family were just the superheroes. They are making dinner on the table. They are throwing these amazing birthday parties. They are showing up at all the kids’ events. The kids are all well dressed, and their hair is combed. I just grew up in this community where the observation was the matriarchs are pouring everything into their families, and the success of the family is the success of the matriarch.

I never really peeled back the curtain to understand what goes on at home inside the four walls to see if that’s actually what’s going on. I can say in my own home my mother was exhausted. She worked a full-time job. She took care of four kids. My dad was out of the house a lot with his work, and my mom did everything. I think I just kind of by example absorbed that that was the expectation, and I never saw my mom be like I need a break, or I am going out. Even when she would go hang out with her friends, she would always have a kid or two in tow. She never took that time for herself, so I never saw it modeled.

For me, it was about taking the realization and realizing that I want a bigger and more joyful life and that it will actually probably lead to more clarity and actually drop the fear level in work and will enable me to show up the way I want to show up.

Brett: Tell me a little bit more about how this started to land in you and how the transformation occurred.

Jaime: This is going to sound weird, but I was on a business trip. We were on the plane, and the flight attendant does their thing where they are like if you are traveling with a small child, put the oxygen mask on yourself before putting it on the small child. I was like I need an oxygen mask for myself first. It was just this deep knowing from within me. Where is my own oxygen mask? I started just thinking about that. I started studying how leaders work.

Joe and I were doing a lot of work at the time about speak your truth, own your truth, and I was working for a leader at the time who is a very dominant leader, someone who walks in the room and just like screams at everybody if it wasn’t exactly the way they wanted it. I was working with Joe, and I am like I don’t know how to deal with this leader. Everything I try to do doesn’t please them. Joe was like why don’t you just show up and do what you want to do and ignore the leader. I was like okay, that’s an interesting experiment.

I walked into a room one day and this leader had been yelling at me for like six months in front of the team, behind the team, one-on-one. It didn’t matter. It wasn’t that he was mad at me. It was just like he was so frustrated if everything wasn’t exactly the way they wanted it. They started yelling, and I said I can tell you are scared. It was just so clear to me that the yelling was actually out of fear of not being successful. I just said I can tell you are really scared, and I said I just want you to know I don’t respond to yelling. I actually become less creative and less able to help you solve the problem. Then I just sat there. I didn’t try to fix him. I didn’t try to make it okay. I just sat there.

He looked at me and then he smiled. He leaned forward, and he was like great, let’s start solving the problem. It was just like this total 180 in our relationship. I was like oh, maybe I should just do what I want. That was a big piece of it. Joe had also come in and worked with my team. He came to me, and he said Jaime, I just want you to know I see a lot of fear and uncertainty in your team. We started unpacking that and thinking about where that came from. I think, again, that was a lot of just they couldn’t channel me and my thought process and my decisions because I was so focused on managing each of them to the way they wanted to be managed that there wasn’t an ability to be like no, she is always like this. She’s just going to say this. Every single meeting they were like is she going to want this today or that. Is this going to be wrong or right? That sucks when you are an employee.

Brett: They are spending a lot of time calculating how you were going to respond, and they don’t have a consistent model for understanding it because you are not showing consistency. You are showing some mirror of how they are to be with them and the way you see them as being. It is not really how you actually want to show up. That decreases trust. People are just unable to trust what they can bring to you and how you are going to respond to it.

Jaime: Exactly. It would actually be far better to be like my boss who is just screaming at me all the time because that’s very consistent. I know exactly what I am going to get. I didn’t want to be that leader, but I did make a bunch of changes kind of all at once. I changed the way I ran my schedule. I like to do my deep thinking, problem solving in the morning. I like all my one-on-ones on one day, whatever they are, just structural kind of things for a day. I had my assistant help me get all of that lined up. I made sure that there was fifty percent white space on my calendar at the beginning of the week so that I had time to work on the problems I wanted to do because that’s just what I need.

I changed the meeting structure, how we communicated as a team, and then I pulled the whole team together. I said look, this is a team, and this is right as we were going into COVID. I was like this is a team that’s kind of newly forming, and we are not cohesive. I just showed up super vulnerably and the way I wanted to show up, not worrying about what they were going to think and just said we have really got some work to do on team culture and team cohesion. We went through a series of workshops over about three months, all virtual because it was COVID. We came out with a series of commitments and how we wanted to work, the principles we had for a team.

I just watched this team go from not being able to set goals or agree to anything, completely fearful, to a virtual team where they were collaborating with each other. They were working to solve problems. They were bringing me decisions and not just squabbling about things anymore. They were setting goals and hitting their goals, and so it was like all I had to do was just show up vulnerably and be like I don’t have confidence that this is a team that can win. We have a lot of work to do, and I need you in it with me. We did a bunch of work together and we came out the other side. It was just such a great transformation that I saw with them, too.

Brett: It sounds like when you went through this process of just reimagining the way you show up. How do I show up the way I want to? How do I show up to work the way that makes me successful? Not only did you succeed in restructuring the work environment for yourself but it also permissioned it for others who work for you and also modeled it for your manager at that time. That sounds like a really vulnerable thing to say to somebody who is yelling at you and who is a superior to you in the organization to say I see that you are scared.

Jaime: Right, but it was just so clear to me. It was like oh, this is what my kid does when he is scared. I bet we all do that. It is like it came out of me. The filter was gone. The filter of how he is going to respond to this. Maybe you don’t do it, but you start playing chess in your head about if I say this, then they are going to do that or they are going to feel that. That chess game starts happening.

Brett: The 4D chess.

Jaime: I hate it. It was like the first time in a long time that I just shut the chess game off and was like I am not going to do that. I am just going to go with the first thing that came in my head. The first thing that came in my head is he is scared. I see you are scared. Then the second thing that came in my head was we have a problem to solve, but I can’t do it with you yelling at me. I said that. Yeah, the 4D chess, that’s kryptonite for me. I hate it. I am bad at it. I am bad at chess.

Brett: I want to speak to some of the fear that would hold us back, the fear and the shame that would hold us back from taking these steps. I am imagining an extreme edge case here where you are with your child. You have been with your child all day. You need space. You need something, and nobody is there to provide it for you. Maybe you are hard on yourself for not having asked, so no one is around. Your first impulse is just to get up and walk out and go for a walk and leave them alone. What would make it that you wouldn’t do that?

Jaime: When it is a nine-month-old baby, you shouldn’t do that probably.

Brett: Exactly. My question here is there are times where your impulse. You were just telling me a number of stories where you trusted that impulse, and you just did it. Wow, things transformed and changed around you. I think the thing that holds us back from trusting our impulse is we believe if we actually follow that impulse, everything is going to fall apart. We are going to be attacked. Our baby is going to die, put its finger in a light socket.

Tell me a little about how that has shifted for you, how your fear of the consequences of taking care of yourself and getting what you need, and how it has shifted the way you go about it to maybe dispel the notion you would start acting in ways that are damaging to your child or to yourself.

Jaime: I started with a lot of playing the 4D chess ahead of the thing. I guarantee you I am going to be in a meeting, and I am going to get yelled at. Probably this person is going to yell at me tomorrow. I started playing the 4D chess, and it was like, if I say this, what’s the worst thing that can happen and go through that exercise. The Stoics do this all the time. They say to imagine your death and then imagine past your death. What happens the hour after you die? What happens the day after you die? What happens the week, the month, the year, the decade? You become just totally okay with death as part of this process that the Stoics lay out.

I started doing that with scenarios that I was worried about and saying if I said screw you, you can’t yell at me, what’s the worst thing that can happen? If I got up and walked out, what’s the worst thing that could happen? If I sat there and started crying, what’s the worst thing that could happen? Just try a whole bunch of different things and feel what feels right and resonates in me. Am I okay with those consequences? In all cases, by the way, it works. The worst thing that can happen is you get fired. Okay, I have three recruiters calling me right now, whatever it is. I am probably okay with getting fired.

For me, it was thinking through that a lot and realizing the consequences weren’t as big and scary as I thought they could be and really imagining and experiencing them, sitting in that, really imagining and feeling yourself getting fired. Then what happens the day after you got fired? What happens the week after you got fired and the month after you got fired? I got to a point where I was okay with it, and then I felt very free at work because the worst thing that could ever happen is I got fired. That would be okay.

At home, I started doing similar things where it was like what’s the worst thing that can happen if I leave. Now my kids are eight and 11. If I leave and go for a walk for half an hour, what’s the worst thing that could happen? They could get in a fight. Okay. I think through all of those things. Sometimes I set up preventative measures where it is like I need some me time. I am going to go for a walk, and I will be back. Here is an activity for you, and here’s an activity for you. Now I am out. Sometimes it is like I am going to go for a walk, and we are all going to the park. You can play at the park while I walk around the playground. I try different things like that to realize what I need and how I set it up in a way where people are safe and that’s it.

Brett: It sounds like a major difference in what you had just been describing about playing the 4D chess in advance, which is a lot like rehearsing a conversation versus the Stoic practice of seeing through your death, which ultimately everything seems to land in that. If I lose my job, then I won’t be able to take care of myself. I will die alone and miserable and I will be disrespected and everything. It all seems to finally end in that, but we are often just not willing to vision that far into our future and actually test the hypothesis in our simulation.

I think the major distinction here is that often people rehearse a conversation so that they can play the chess game and avoid the consequence they are trying not to get, being yelled at, rather than just seeing all the possible moves on the table that they could play and then all the counter moves they could play to all the possible moves played back at them and then accepting the entire thing. Then showing up and being like, I am just going to be me because that’s what feels better in my system now and in the long term, and I also trust that’s going to lead to better outcomes for me and everybody around me. That might even include that I am fired and then I go to a different job where I am not being yelled at.

Jaime: Or I get a week off in the summer to hang out with my kids or a month while I look for a job.

Brett: Or your kids learn to resolve conflict with mom not around. I am also curious now to whatever extent of helicopter parenting. I think all parents have some level of it. Am I over parenting? Am I under parenting? How has that shifted as you have gone through this transformation of taking care of your needs and putting on your own oxygen mask and seeing through the negative consequences you don’t want?

Jaime: A thing I have done is I have tried to empower my kids now. There is a checklist on the fridge. These are the things you need to get done today, and they are responsible for getting it done and then at about six o’clock after we have had dinner. I am like is your checklist done. If it is done, then great, you can have free time and do what you want. If no, you know you need to get that stuff done. That’s just an example of where I have totally pulled out because I don’t want to micromanage. I even told them that. I said I don’t want to micromanage. I find it really stressful. I don’t want to get in an article with you about if you need to have a shower for the second time this entire week or not. You need to be clean. It is just on the checklist. You follow the checklist.

That’s brought me more space so that I don’t have to be like mad and in these negotiations. I hate negotiating with my children, but at the same time it has also given them empowerment. They can decide what order they do it in, what time they are going to do it as long as it is done by six o’clock. Otherwise, they don’t get free time. That’s just brought a lot more joy and peace into the household.

It has also made me much more connected to them and then more connected to me because the interactions we have aren’t about negotiating if you should bathe for the second time this week, but they are much more about great job in school today. I was looking at your homework. I am so impressed with how well you did on your math test. We are connecting on things that feel much more meaningful and less on things that are just the minutiae of being in a family together and getting chores done.

Brett: It sounds like from what you were saying earlier, there is a similar letting go of micromanagement in your team at work. You recognize that those who hired you want you to be doing what you need to be successful and meet the goals and metrics and be an active and empowered part of how you work. That trickles down to those on your team.

Jaime: That’s right. Even now we are hiring a bunch of people. We are an early-stage startup. I interview everybody that’s coming on the team, but very rarely do I veto. I have done it twice in all of the people we have interviewed because I am much more here to empower you as the hiring manager to make your own decisions, and I am just going to give you perspective on here are some things I think are going to be important as they onboard, here are some challenges you may have with them as you are managing them, whatever the insights are that I see.

But they will sit there and at first it was very odd for them, I think, because they would look at me and be like should we hire this person or not. You interviewed them. You are the boss. I am like I am not the hiring manager. I am not deciding. Here is what I see. Just really pushing that empowerment to my team is really important to me.

Brett: Where do you see your next edge? One of the things we talk about a lot is that this process of self-discovery is a corkscrew. You swing around one time, and you find all these ways you have been holding yourself back and limiting yourself. Then, through deeper awareness, you transform, and you change the way you show up in the world. You swing back around the corkscrew, and it is the same thing again but on some fractal, more subtle layer or level. I am curious. For you, what is the version of this that’s most alive for you as an edge today?

Jaime: That’s a great question. Right now the thing I work on a lot is I can’t save people. I have this tendency to be like you are empowered. You do you. But then when they are about to fail, I am like let me help you, let me catch you. Now the thing I am working on is like no, maybe they are not going to fail, and I am wrong. Maybe the failure is the learning that they need or maybe them being weak in that role is actually what’s going to strengthen the team by having the team see it and come around. There is a lot more of me pulling back. I am working on it. I am not perfect at it right now, but it is very top of mind. Me pulling back and being like I see where this is going, I think it is going to be a problem, but I need to let the person who is responsible and empowered, I need to really mean that and let them go and forget their own path.

I’ve done it right a few times and wrong a few times lately. When it is done right, what I see is the team is stronger.

Brett: Something I have learned on this same kind of path, being a classic savior myself, is that when I am on the path, I am often vacillating between over controlling and trying to save them from the inevitable failure I see them walking into, whether or not I am actually correct about that, or I am just hands off. I am like okay, they are going to learn on their own. I miss opportunities to give them really clear, something that I see that might be difficult for them to hear and be able to deliver it lovingly and without fear and without talking down to them. That’s an edge. Again, it is a fractal that you just continue to deepen into the subtlety.

Jaime: You keep it hitting that bump. You can take it too far the other day, which is like you do you, good luck, and that’s not helpful either. It is finding, like you said, that sweet spot. That’s the thing I am working on now.

Brett: You can get to that point where you are so hands off where you are like why is my team continuing to fail. I am letting them be empowered and do their thing.

Jaime: They are empowered. It is up to them. No, it’s not. You are the leader. I always say the wins are yours, the failures are ours.

Brett: There is another phrase I really enjoy, which is: What if it is not your fault, it is your responsibility. As a leader, when I start to think of something that might be my fault, whether it is me or somebody I am leading and a decision that I could have been a part of and steered or brought reflection to, if I am afraid of fault on some level, then that creates a threat on my system. Then I come from fear, which leads me to either over control or avoid. But if it is just responsibility, my own self responsibility, like not outwardly, imposed responsibility that I should do something. I am responsible for the outcomes in my life, and if I am running a business and I see things going on, if I want that to be addressed, it is my responsibility to speak up. But it is not my fault if something goes wrong, fault meaning I don’t have to shame myself for it. I don’t have to love myself any less because I allowed something to occur that I could have spoken to and didn’t.

Jaime: I think that’s right. I think most of the time for me when things go sideways, it starts with shame. The voice in the head turns on and goes you should have done blah. Then the shame starts, and then at that point, you are not only trying to manage the situation, you are managing yourself. You are not in connection with anything. I find that you have really got to get back in connection with yourself.

I always try to tell the team. The phrase I like is let’s just look at this like a patient on the table. What are the symptoms? Then, what’s the next step in treatment? Solving problems like that and not worrying about whose fault is something I think is just a really good way to keep the shame from cropping up in people. Then they can stay much more in the problem-solving mode.

Brett: I could imagine an ER doc being the person who had crashed into somebody, rushing to the hospital with them and then being the person to work on them, carrying the whole what have I done with them. How effective is that going to be? That person just needs to go through their process and then somebody else who is not as directly attached to the situation. Maybe there is a case where somebody would actually be able to do the best possible job because they feel a deep responsibility to themselves to show up to that situation and be fully present with it, but to the extent they are hard on themselves about what happened, it wouldn’t be very effective.

Jaime: That’s right. I think we show up better, we solve problems better, we get to better solutions when the shame is off, and we are just focused on here’s the thing. I’ve got to get this thing done. I am responsible for getting this thing done. I think our businesses are better, our families are better, and our personal lives are better for it.

Brett: It sounds like not only for yourself but for your family and for those around you and those who work with you, which flies in the face of this impression that we are taught that it is selfish.

Jaime: Exactly. I think it is not selfish. I think it is being in connection with yourself, for sure, and owning what it is you want and speaking your truth. But I think it is setting up the conditions for success in whatever it is that you are doing in that moment. When you do that, you are actually much better to be around. The things you are delivering are much better. I don’t know. Maybe selfish is okay, working title.

Brett: I love it. Thank you so much, Jaime. I really enjoyed this.

Jaime: Thank you. It is so good to see you.

Brett: You, too. Take care.

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