From Student Affairs to Soul Work: Annalyn Cruz on Leadership, Risk, and Rewriting the Script

Today I interview Annalyn Cruz, a dream life and embodiment coach and the CEO of Grounded in Wisdom, LLC.

We discuss Annalyn’s career journey from higher education in student affairs to learning and development in the corporate world, and back to higher education. With each transition, we revisit her commitment to empowering others, and the role of strong personal relationships in building trust and self-confidence.

00:00 Introduction
03:09 Interview Begins
05:05 Early Career and College Experience
08:17 Discovering a Career in Higher Education
18:17 Graduate School Experience
20:26 First Job in Higher Education
22:46 Challenges and Growth at San Jose State
26:55 Exploring New Paths: Recruiting, Bartending, and Makeup Artistry
33:25 Returning to Higher Education at UC Berkeley
38:46 Career Progression and New Challenges
39:14 Inherited Team Dynamics and Struggles
41:20 Emotional Vulnerability and Team Shift
47:10 Transition to Semester at Sea
48:28 Pivot to Learning and Development
50:32 Taking a Step Back for Future Growth
58:59 Corporate Experience at EA
01:03:22 Starting a Business and Balancing Roles
01:10:59 Coaching Focus and Final Advice

Transcript

0:06

Welcome to the Push Pull podcast. I'm Varun Rajan, and here we interview professionals about their career transitions, specifically the push and pull factors that inform those transitions. On today's episode, I had the pleasure of reconnecting with Annaly Cruz. I actually used to work for the computer labs and the residence halls back in my undergrad days, And she was actually one of the academic program coordinators. we didn't work together very much, super directly, but when we would have, but we would see each other all the time. And I think she actually interviewed me. Um, so it was super awesome to reconnect after all of these years, Annaly spent the bulk of her career in higher education in student affairs, but also made a pivot later on to learning and development, which she carried over into the corporate world. and now she does have a nine to five back in higher education, but. Her main sense of purpose and fulfillment is her business right now as a dream life and embodiment coach. And I will let her speak to that a little bit more. this was such an amazing conversation. Annaly had an incredibly strong sense for empowering other people. Very early on in her career, She used that affinity for empowering and coaching others as kind of a core principle, and followed that principle, uh, from one job to another. She really focused on making sure that she could. Enable other people to be fulfilled in their work, and take on new leadership roles, all that kind of stuff. and she used that idea of empowering people as a core principle that she followed from one job to another. And she followed that principle, even if it made potentially making a mistake and then pivoting quickly away, uh, once she did make that mistake. One, one example that comes to mind. From our conversation is when she actually went into a recruiting role thinking that she would actually be playing more of a coach type role for the candidates that she was working with. When she found that it was not for her, she realized that she had made an honest mistake based on her values and decided to move on and find something else. something that has come up in a small handful of my conversations, but definitely, uh, was. Prominent in this one is that Annaly prioritizes very strong relationships, friendships, allies, confidants. We didn't call that out necessarily in the conversation explicitly until towards the very end, but that's a big part of it, and I think that's something that really helped her. With her trust and self-confidence in making the big bets on herself and taking those, uh, calibrated risks, uh, because she was able to balance listening to her inner voice as well as the voices of the people that she trusted the most in her life. So, I learned a lot from this conversation, and I'm sure that you will too. The other thing that I will say, just FYI, My fire alarm either ran outta battery or started malfunctioning towards the end, so you may hear some annoying beeps. I tried to get most of them out into editing, but anyway, sorry about that. without any further ado, I'm excited to introduce you to Annaly.

varun_1_04-30-2025_154524 3:15

Okay, we're here with Annalyn Cruz. Thanks so much for joining us, Annalyn.

annalyn-cruz_1_04-30-2025_154525 3:19

Thanks and happy to be here. my name's Annalyn Cruz. I'm a dream life and embodiment coach, and I'm the CEO of grounded in Wisdom, LLC. And I also have a full-time, role as well as an organization consultant and leadership coach. So something that I really am passionate about and care about and, actually moving towards pivoting my business is I mentioned I'm a dream life and embodiment coach, and solo, child-free women of color, go from having a life centered around familial and cultural expectations to really creating a life that, that they really crave. So helping, that particular community really find themselves and find what is in their own alignment of the type of life that they really wanna lead for themselves. And that's based on my own, life journey over the past many years where I was trying to figure out, okay, what is it that I want in my life that is outside of. Expectations, whether it's family, culture, media, under the sun, except for my own voice. So that's really what, I'm moving towards and what I really care about and I'm passionate about.

varun_1_04-30-2025_154524 4:45

I can't wait to discover with you, to together a lot of the motivations that led up to that. I'm sure you have a good grasp on what that is. but I'm curious to know about, just the years leading up to you forming the business and how you arrived at the philosophy that you have, in, in terms of how you serve others today, through that business. so if I were to ask you Annalyn about the beginnings of your career, where would you start?

annalyn-cruz_1_04-30-2025_154525 5:12

I would probably start. In college, like at the university, I was an alum or am an alum of uc, Santa Barbara, go Gauchos. And and while I was there, I did a lot of student leadership roles while on campus. started out in residence hall, student government, worked on orientation staff, worked in the counseling and career services as a stress management peer. worked in res life. And so my career has been, In a bunch of different spaces. One in higher education, working both with students at the university, like how we first met many years ago.

varun_1_04-30-2025_154524 5:54

Yes.

annalyn-cruz_1_04-30-2025_154525 5:54

and helping college students outside of the classroom. Like all of the learning and development that happens within that space, along with, helping the staff members, people who work at a university and developing them and helping, managers and leaders figure out what type of culture are they building within their teams. So that's a lot of the work that I do in my full-time role currently, is to support those who are often in these leadership roles and figuring out how teams can work most effectively together. later on in my career, I really focused on learning and development. So

varun_1_04-30-2025_154524 6:35

yeah.

annalyn-cruz_1_04-30-2025_154525 6:36

Working within the hr, the people experience space, worked for, electronic arts, the video gaming company. So that was my corporate gig that I had for, a few years after I left Higher Education. And, and what I discovered there again, it was always rooted in wanting to help people really discover not only being good at their jobs and being leaders, but. What feels within their own, soul's alignment. And so that's where I get into some of the spiritual practices and some of the, ways in which we think about how am I fulfilled in all parts of my life. And so

varun_1_04-30-2025_154524 7:17

Yeah.

annalyn-cruz_1_04-30-2025_154525 7:17

still really intrigues me about, the human experience and making the most out of the time that we're hearing these in these bodies.

varun_1_04-30-2025_154524 7:27

Yeah. I'm really fascinated by the evolution of your thinking, across the course of your, what sounds like a very mission-driven, mission-oriented career. so you started off in undergrad, talking about being in all sorts of leadership positions, and really focused on coaching and mentorship. What, tell me a little bit more about, what came right after undergrad. You mentioned, and obviously you and I met, when you had a career in higher education. Did you go into higher education right away? what did you think that you would be spending a lot of time in the, like higher ed space when you were an undergrad? What were you thinking, about what were you targeting? What were your motivations while you were an undergrad and, what ended up actually being the result when you went out into, the workforce or got your undergrad degrees?

annalyn-cruz_1_04-30-2025_154525 8:17

Yeah. so what I discovered during my undergrad days was that you could actually have a career working in higher ed. That wasn't faculty, right? It was the positions within. Student affairs or within student services for, like I mentioned, the outside of classroom experience that happens at any college or any university. And so when I discovered that you could actually build a career around that and that the people who helped me as an undergrad were actually folks doing the type of work that I would eventually end up getting my master's degree in and, going to Colorado State for my grad degree or for my master's degree in student affairs and higher education, that's where eventually, three years after my undergrad, where my master's degree took me. But in between those years I did work for university. I worked for uc, San Diego, doing some administrative work, and I really saw that as a pit stop to figure What I was gonna do,

varun_1_04-30-2025_154524 9:24

Yeah.

annalyn-cruz_1_04-30-2025_154525 9:24

I was gonna do with my life. I'm using quotations right now that, I really wanted some time in between undergrad and my master's to figure out what direction do I want to go into,

varun_1_04-30-2025_154524 9:37

Yeah.

annalyn-cruz_1_04-30-2025_154525 9:37

and I really wanted to be thoughtful about that instead of just going straight from undergrad to going back to school again.

varun_1_04-30-2025_154524 9:44

makes sense. So it sounds and let me know if I'm hearing you correctly, what I'm hearing is you had a sense of, you learned for the first time being in undergrad that oh, hey, you could have a career in a academia or higher ed that wasn't faculty based. but at the same time you knew that would require some level of like masters and con continuing your education.

annalyn-cruz_1_04-30-2025_154525 10:04

Yeah.

varun_1_04-30-2025_154524 10:05

but in the meantime, you used to, you still wanted to like, take some time to, to figure that out or know that was actually like the right path for you. is that fair? Which is why you got have, okay.

annalyn-cruz_1_04-30-2025_154525 10:14

totally. That's totally fair. And the other thing I will add was that I was burned out from, being in college. Like I just writing papers all the time as a Asian American studies and a sociology, major. And just needed some time off from academics.

varun_1_04-30-2025_154524 10:34

Totally.

annalyn-cruz_1_04-30-2025_154525 10:35

I knew that wanted to just live life and this was early two thousands, I'm dating myself here, But. This was a long time ago where two of my college friends and I decided to pack up and move to San Diego without any jobs, and we were just like, we'll just get an apartment, we'll get a temp job, which is what I did. I got a temp job at UCSD, which ended up, opening the door for a full-time role somewhere else. So I, I am of the philosophy and practice that I just believe the universe is gonna work itself out for me, and we're gonna, we have this agreement that, will just eventually work itself out, of course, like being planful and all of that stuff. But, I believe in just taking pauses sometimes to figure out what is it that I really want for myself. And I think that still rings true 20 plus years later as, I'm much older and wiser, I hope, or I know that I am, to just figure out, again, that internal check-in. what's important to me now? How do I wanna give back now? what am I still passionate about and how has that kind of shifted? Or who do I wanna focus and serve at this point in my life?

varun_1_04-30-2025_154524 11:54

Yeah. How did you, and were you answering those questions for yourself during this time between undergrad and grad school when you were in San Diego? and what did that look like for you? I know you, you had mentioned the kind of temp job at uc, San Diego. There were some other jobs along the way. Sounds like there were, these were not necessarily things that you considered like serious career moves, but something to fill a space for you to be able to provide that. I don't mean to, I don't mean to minimize, what you were doing or anything like that, but I just want to get a sense of how you viewed that time in your life and what you were trying to, what you were trying to do. And I know it was a while ago,

annalyn-cruz_1_04-30-2025_154525 12:33

yeah.

varun_1_04-30-2025_154524 12:33

feel free to,

annalyn-cruz_1_04-30-2025_154525 12:34

me stretch here. I'm just kidding. Going back in the old memory bank, I think consciously I did know that it was a pit stop, like that

varun_1_04-30-2025_154524 12:43

yeah.

annalyn-cruz_1_04-30-2025_154525 12:44

gonna be something that was a pit stop, a stepping stone for what was next. And my manager was clear on that as well. so did know that between two to three years, between undergrad and getting my master's degree and going back to school in that time, I was gonna be really thoughtful about. What I was gonna do next and what that degree would be in. So I reached out, to some former mentors who I knew were in student affairs at the time, talked to a few different people to hear about what was their experience in doing that program. and I just applied to, I think, maybe two or three different grad programs within that particular,

varun_1_04-30-2025_154524 13:33

Specifically student affairs in higher education and.

annalyn-cruz_1_04-30-2025_154525 13:37

And yeah, I think I only applied to two programs actually in the hopes that I would get into one and if I didn't, then I would be living in San Diego for another year. There could be worse things,

varun_1_04-30-2025_154524 13:49

Yeah.

annalyn-cruz_1_04-30-2025_154525 13:50

just trusted again that I would get into one of'em, which I did

varun_1_04-30-2025_154524 13:54

why specifically higher education? I understand where you got that exposure and understood that there was a potential future here. But I'm curious, were there other paths that were on the table that you were considering potentially whether it was like social work or K 12 or, it seems like, you're a very service oriented, mission oriented kind of person when it comes to your career, why did this end up being the path that you took and were you considering others?

annalyn-cruz_1_04-30-2025_154525 14:23

There was not another path I was considering. just in terms of like you said, K through 12 or social work or waiting for a nonprofit, it, that wasn't on my radar because of the impactful experiences that I had in college changed. My career trajectory, or just the my awareness that this was something that I wanted to move towards because I had such, amazing, like growth oriented experience in college, and that I knew that there were, staff members who helped create that experience for me. I wanted to give back in the same way to other college and university students. Once I quote unquote became a grownup, wanted to do that give back in the same way

varun_1_04-30-2025_154524 15:20

Can.

annalyn-cruz_1_04-30-2025_154525 15:20

because of my college experience,

varun_1_04-30-2025_154524 15:23

And, I swear, we'll move into grad school and everything. but it sounds like there was such a, foundational formative period during your undergrad experience here. And we keep, coming back to that being really the impetus for launching you to, to where you ended up going. can you tell me a little bit more about that time? What was it about the support that you got that really made you feel like, you were on a growth path, like you said? what was the difference between Annalyn coming into, uc as Santa Barbara, as a freshman versus a senior? what was, what was the impact that they had on you?

annalyn-cruz_1_04-30-2025_154525 15:57

I definitely gained more confidence in my own leadership abilities. I came from a high school that I. Any leadership, any student leadership position was based on popularity and who you knew and if you were in a particular crowd, right? if you were in a particular group of people. And so I didn't see a path for me in high school in terms of seeing myself as a leader. I didn't get that opportunity, or I didn't put myself in those types of situations. what was impactful for me in college people encouraging me saying, you can do this. I see the leadership potential in you. I see what you can do and how you help influence people. I see that get stuff done, right? Like you're able to build relationships with people. Like these were the types of things that I was, hearing from mentors. And then when I actually saw myself. it and being able to be successful and making that impact from a peer level, right? From peer to peer. that just shifted how I saw myself, right? And because of those people who held me up, who, I think held up a mirror to me to say, yeah, you're absolutely capable of this. I wanted to be able to do. Same, for other students in the future that I would, help support. So I think looking back on, on those days and that time period of my life where I was lacking confidence, where I didn't know where I was going in terms of my career, I just, again, was an open book and open sponge, I guess of, let me just see what happens. That's how, I've lived my life for a lot of it, of I'm just open to seeing what comes through versus I'm gonna be a doctor, I'm gonna be this right. I'm gonna be an engineer to my parents' chagrin of,

varun_1_04-30-2025_154524 18:03

Right?

annalyn-cruz_1_04-30-2025_154525 18:04

choosing a path like that. but yeah. Does that answer your question?

varun_1_04-30-2025_154524 18:09

Yeah, I think so. it makes a lot of sense. and that's wonderful. let's, fast forward to like where we were chronologically. You go to grad school. Tell me about that experience, what you got out of it. you took a leap of faith on yourself. You were also like wholly dedicated to this particular path. what was that like? Did it meet your expectations?

annalyn-cruz_1_04-30-2025_154525 18:29

I think,

varun_1_04-30-2025_154524 18:30

I.

annalyn-cruz_1_04-30-2025_154525 18:31

looking back on that time, couple things come to mind. One, it was a big transition for me to move outside of California and end up in Colorado. it, I would say it was a little bit of a culture shock at the time. And again, this is in the early two thousands. But it was a bit of a culture shock to leave that sense of home within California and that sense of community that I had at the time in San Diego and then just voluntarily uproot myself,

varun_1_04-30-2025_154524 19:09

Totally.

annalyn-cruz_1_04-30-2025_154525 19:10

And but luckily I had a couple of, people who were there already, who I knew at the university and who helped recruit me into the program that I was in. And it just felt right when I went to go visit and interview for the program and all of that good stuff. and. if I could do it all over again, I would, because it was a cohort based program where I got to know the folks, in my program, like really well. we did classes together. We were working in our grad assistantships together, we were socializing together, right? there was all of that kind of happening within those few years. at the same time, I knew I wanted to come back to California. that was just home. And I, again, I saw that experience as a pit stop or as a milestone for what was next for

varun_1_04-30-2025_154524 20:08

Totally. Yeah.

annalyn-cruz_1_04-30-2025_154525 20:11

yeah, so it, it was a really, hard time in life and it was also really fun at the same time. And yeah, I got a lot out of that experience.

varun_1_04-30-2025_154524 20:22

and so what came next after the graduate program wrapped up.

annalyn-cruz_1_04-30-2025_154525 20:26

I moved to the Bay Area and, worked in higher ed. So yeah,

varun_1_04-30-2025_154524 20:31

And was that the, was that, was this similar to the San Diego story where you like decided to move somewhere without having a job lined up? Or did you get the job lined up first?

annalyn-cruz_1_04-30-2025_154525 20:41

had a job lined up. I was the first

varun_1_04-30-2025_154524 20:43

Okay.

annalyn-cruz_1_04-30-2025_154525 20:44

to get. job offer, and

varun_1_04-30-2025_154524 20:47

Wow.

annalyn-cruz_1_04-30-2025_154525 20:48

was excited because it was in the bay and I had, a few of my college friends who moved up here, whether it was, they were from here originally or just ended up here. So that felt really good to actually be back in the state, but have a new adventure for myself. And, yeah. So I did have a job lined up.

varun_1_04-30-2025_154524 21:12

Yeah.

annalyn-cruz_1_04-30-2025_154525 21:13

Yeah.

varun_1_04-30-2025_154524 21:14

tell us about it. what was it like, where was it at? was it, and this is this was, I'm guessing the first of the path that you had set up for yourself, right? Like student affairs at universities.

annalyn-cruz_1_04-30-2025_154525 21:25

totally.

varun_1_04-30-2025_154524 21:25

what you would expected? Really curious to know, like you're arriving right, to, to some degree at what you had been aiming at.

annalyn-cruz_1_04-30-2025_154525 21:32

Yeah. I wanted to do, I wanted to do leadership and work within the diversity and inclusion space. So I got a job at San Jose State, at the cross-cultural center did a lot of, program development. I supervised our interns that worked there at the time. did a lot of, yeah, leadership development and a lot of collaborations with other colleagues across campus. So yeah, I did that for a few years and it was really fulfilling.

varun_1_04-30-2025_154524 22:04

Yeah.

annalyn-cruz_1_04-30-2025_154525 22:04

it was really fulfilling to work, in that space with those particular students at that time of my career. Yeah, I

varun_1_04-30-2025_154524 22:13

what, yeah. te tell me more about the specifics of the, like cross cu, the cultural center. what was the organization like in terms of who was working there? Who were you reporting to? I think like for myself and for a lot of people, that may not work in higher ed. not totally sure what all of those kinds of things look like. So one of the things I'm curious about is who are you interacting with? Who are you accountable to? In what ways did that make your job really fulfilling versus, where might there have been layers of bureaucracy that were really frustrating?

annalyn-cruz_1_04-30-2025_154525 22:45

Yeah. we served the entire campus and yet we were a staff of three full-time staff members. There was the

varun_1_04-30-2025_154524 22:54

Wow.

annalyn-cruz_1_04-30-2025_154525 22:55

myself, I was the assistant director, and then we had our admin coordinator. the rest of the staff were students, who were going and

varun_1_04-30-2025_154524 23:05

Cool.

annalyn-cruz_1_04-30-2025_154525 23:05

And they were undergrads at San Jose State. so we were really focused in on creating community and experiences for, for primarily underrepresented right? Those who identified, as students of color. We also, while we were there, we, also supported our Jewish and Muslim students as well. So I would often help them, programs that were community based, right? So we had diversity advocate interns is what they were called at the time, who would host programs and community gatherings for their, particular communities. Of course, it was open to everybody, but each person had a focus of what they were trying to do. And within that space, I also taught a leadership development class a couple of years, and got to. create the curriculum for that and have maybe 25 undergrad students that signed up to, to do this particular leadership experience. They got,

varun_1_04-30-2025_154524 24:13

Yeah.

annalyn-cruz_1_04-30-2025_154525 24:14

got college credit for that. and I served on a bunch of different, campus committees. And for those that aren't as familiar, I said, there, there's the academic side and then there's a student services or student affairs side of how a university is run. And often was super gung-ho to be a part of the division of student affairs and give back in that way, right? So I think about the pull through or the thread around my career of. Really wanting to make a bigger impact than just being in my current role, right? I wanted to learn about the ins and outs of how the university was being run

varun_1_04-30-2025_154524 24:56

Cool.

annalyn-cruz_1_04-30-2025_154525 24:57

supporting the students in ways that were, again, outside of the classroom. Like how are they becoming better human beings? How are they gonna be, upskilling themselves with their leadership skills? Because guess what, those are the folks who are gonna be in the workplace like in the next four to six years, and are we preparing them for the adulthood that awaits outside of the university?

varun_1_04-30-2025_154524 25:24

this is so cool, because you joined for this specific role and there was a bunch of stuff that you were excited about, as a part of that role, but you were also volunteering to be a, to either observe or be a part of like other different organizations on campus to get a better understanding of how the whole student was being supported, Like eventually at some point you did end up leaving San Jose State, and I'm curious, did you get that experience of trying to learn more about how students were being supported to a point where you felt like it was. Also something that you could contribute to?

annalyn-cruz_1_04-30-2025_154525 25:57

I felt like I had all the growth I and development within myself that I, there was only so much that I could progress in the role that I had, and we were a small, we were a small department and my manager wasn't going anywhere at the time. I made the impact that I wanted to make and couldn't see my career progressing any further in the way it was structured at the time.

varun_1_04-30-2025_154524 26:25

so you're at San Jose State. This is your first job, out of grad school. working in student services in higher education, you're doing a lot of stuff. You're trying to go beyond the scope of your role and learning how to serve the student, but you're finding that your own growth and ability to serve is hampered by the organization around you.

annalyn-cruz_1_04-30-2025_154525 26:45

and so I felt like, why

varun_1_04-30-2025_154524 26:48

it is.

annalyn-cruz_1_04-30-2025_154525 26:49

pursue some curiosities outside of higher ed? What does that look like? Which led me to a role in, in recruiting for a small boutique company.

varun_1_04-30-2025_154524 27:01

and you found out pretty quickly it seems like that it wasn't for you. Is that right?

annalyn-cruz_1_04-30-2025_154525 27:07

Yeah, I quit that job within five months, because

varun_1_04-30-2025_154524 27:10

I.

annalyn-cruz_1_04-30-2025_154525 27:10

I felt like my skills and talents weren't aligned and felt that, I. It wasn't fulfilling work. for me, I wasn't making the impact, the direct impact that I wanted to make with people. I think at the time I probably envisioned it to be more of a coaching role rather than A recruiting role, which that's my bad, I guess not fully understanding or maybe not necessarily knowing all the ins and outs of what recruiting would mean, at least with that company. it wasn't the right fit, and I found myself pretty miserable day in and day out. in the short amount of time I was there. And I remember a conversation I had with my sister and I was just crying to her saying how unhappy I was and I wanted to make a change and I was longing to be back in higher ed. Like I was looking at all these job listings to go back to what I knew. because she knew how, unhappy I was. I remember at the time she said, I. just quit. it's not worth, it's not worth your wellbeing. It's not worth, your health being affected by this. So I will help you out financially in the meantime, like you figure stuff out, so I quit that job and then I actually pursued. Two things that I had a big interest in, which had nothing to do with higher and nothing to do with recruiting, which was, I went to bartending school

varun_1_04-30-2025_154524 28:46

Cool.

annalyn-cruz_1_04-30-2025_154525 28:47

I became a makeup artist. and yeah, I don't know if you knew that about me. That was my job

varun_1_04-30-2025_154524 28:52

No.

annalyn-cruz_1_04-30-2025_154525 28:53

I got to Cal. Yeah. so I wanted to pursue that and just, I took a part-time job and just makeup was always something I was interested in, and it's a way in which I, get my creative kicks, from. And so I decided to do that and I just again, figured out, I could do this in the interim, I could get a part-time bartending job as well. And so I was on that path until got my job at uc, Berkeley.

varun_1_04-30-2025_154524 29:22

I would love to know, even at this point, like this is the second time you maybe take a chance on yourself and you have some support obviously from like your family, whether it's financial, emotional, et cetera. but there was a time in your life beforehand where you were like, all right, we're gonna move to San Diego and just figure it out and take on jobs and blah, blah, blah. But these jobs in different, like before it was like, let's do the kind of temp jobs in higher ed and gear me towards what's next. This one was like. Okay. I know I wanna go back into higher ed, but I also want to, I also want to unshackle myself from just what my career is. I, is that fair to say? And, What would your advice be to someone that has you know, rage quit their job or is just okay, I know I'm gonna go back to work, but I have some time on my hands and I just wanna maybe make some money, but just explore some things.

annalyn-cruz_1_04-30-2025_154525 30:07

yeah. I thought to myself, this might be the only time that I'm in between roles that I could, I. something that's always been a fun passion of mine, in terms of being a makeup artist and what would that be like, what would it be like to be a, at a boutique in Union Square in San Francisco, and I actually really enjoyed it.

varun_1_04-30-2025_154524 30:29

yeah.

annalyn-cruz_1_04-30-2025_154525 30:30

I didn't enjoy some of the drama that was going on in terms of the other employees, but working with, customers and clients and having them feel really good about themselves after we do, makeovers or after, I'm like selling them a product that I personally believed in. I was like, oh, I could do this. This is good. So for me it was a again, Hey, let's follow this curiosity. I think that's always something that I think about in terms of my career is I have a curiosity about it, I owe myself enough to. into it, research it, try it, talk to people who are in the industry, whatever the case may be. and then bartending. Going to bartending school. I just thought that sounds fun. I can meet new people. I, again, I don't have a full-time role right now. I think I would be a great bartender talking to people and socializing and serving them drinks on the side. as I'm talking about this, Varun, it's interesting'cause I'm like, what drew me to both of those experiences or types of jobs? And it's the people, it's like being able to help people or to, I don't know. It's it's what led me to coaching, right? It's like holding space for people so that they somehow, Yeah, are changed, are transformed, right? whether it's through makeup or,

varun_1_04-30-2025_154524 31:54

Yeah.

annalyn-cruz_1_04-30-2025_154525 31:54

or like the good news about a bar could be like, oh, people are socializing. They're connecting. And, I'm providing an experience, that hopefully gets them to have a good time, right? there, there was just something appealing about that. And I met some really fun, cool people who were also in the bartending program. I got a little certificate saying I was officially, a graduate of the San Francisco Bartending School. yeah. and got to serve drinks at, a bar that was near, near that area where the school was. So again, had I not gotten that full-time role, at Cal, I would've continued to. Do makeup and makeup and bartend and see where that would've taken me until I figured out what was next.

varun_1_04-30-2025_154524 32:44

Yeah. You followed your curiosity and you also, had faith that you were gonna land on your feet, it sounds which I think, a lot of people can really learn from that kind of balanced, I think calibrated risk taking and like confidence in self.

annalyn-cruz_1_04-30-2025_154525 32:59

And

varun_1_04-30-2025_154524 32:59

yeah.

annalyn-cruz_1_04-30-2025_154525 33:00

and I don't think I was conscious of it at the time, so it's interesting having this conversation again, many years after where it's like, what did I learn from that experience? And yeah, following my curiosity following, what felt like a creative endeavor, right? It's like not knowing what the outcome would be, but also knowing nothing's permanent,

varun_1_04-30-2025_154524 33:25

yeah. so Cal, where you and I met, tell us about the job that you got there. it seems you had quite a few roles and so I'd love to know like why did you join, what were you hired for? How did your role change and evolve over time? how much of that were you targeting and driving in terms of the change of your career over your time at Cal? versus like when you know somebody needed you for something and that was an opportunity that kind of came to you.

annalyn-cruz_1_04-30-2025_154525 33:53

I got a role, at Cal as an academic program coordinator. I did that for. three years, I wanna say. and for me it was less about the role, it was more about I want to get back to higher ed. and I wanna get back to, working with students again. I really miss that after maybe not doing it for less than a year. I was like, it's calling me back. I had a friend at the time who worked at Cal, she referred me to the job. And honestly, when I first looked at it, I'm like, never really worked in academic services. that's not really I think I'd wanna be doing. and she had convinced me to look more closely at it. And she's there's really great people that work there. you'll have some flexibility and freedom to. To shape the way you want the, your particular academic center to be. You get to develop your student staff. So those were the things that actually appealed to me, was almost like running my own little shop, right? and having, and being able to hire an awesome team of students who could then help run the center with me, I did have amazing colleagues that I interviewed with and I just liked the vibe of the culture and the team. So that's what kept me there, for the next few years because I really wanted to, again, get back to that higher ed environment. It's what I knew, it's what I went to school for, and it just felt right at the time.

varun_1_04-30-2025_154524 35:28

Yeah. Was there anything that, anything that stands out to you about, notable moments or achievements or even cha challenges, that you had during that, when you were academic? program coordinator?

annalyn-cruz_1_04-30-2025_154525 35:40

had to open up a new center actually. so there was,

varun_1_04-30-2025_154524 35:45

I.

annalyn-cruz_1_04-30-2025_154525 35:45

so what that meant was, breaking ground in a new center, looking at blueprints, like choosing what type of equipment along with my colleagues, like how can we create not just a center where students would go and study and get on the computer. But it's for me, I really wanted to create a center that felt very community oriented, that this was a hub which students who lived in those residence halls would actually think it was cool to hang out there and to socialize and that we would. Do stuff beyond, what was currently being offered. So that's the way I always see, any role that I'm in, I think about how can we make this a bit more innovative? How can we make this feel a bit more community focused? How can we make the environment feel like people belong here and that they want to be a part of this culture that we're creating? so for me, I'm really proud of that, of what me and the student team were able to accomplish in the couple years that we were there. was really building a center from ground up.

varun_1_04-30-2025_154524 36:59

That's awesome. what, what came next, within, uc, Berkeley,

annalyn-cruz_1_04-30-2025_154525 37:04

Yeah. I had, I had an interim role, for

varun_1_04-30-2025_154524 37:08

I.

annalyn-cruz_1_04-30-2025_154525 37:08

a year, which is honestly probably one of the hardest. I. Positions in my life because think I wasn't fully prepared for what was about happen. So I, I moved from basically a coordinator role to pretty much a director role with, a whole lot of development and support. I was just I said yes, then because I wanted a leadership role, I wanted to have that experience, and I often felt like I was flailing because it was just, it was a really tough transition, I would

varun_1_04-30-2025_154524 37:49

Yeah. What, how did your responsibilities change? what got you to say yes? I, I, I, it sounds like leadership role, right? yeah. what were you doing as the kind of a PC role? What were you promised would be different, or what were you suggested would be different? What ended up happening?

annalyn-cruz_1_04-30-2025_154525 38:08

Great question. so let's see. I really wanted, again, to step up in my own career trajectory, going from like a coordinator to more of a, assistant director level. so that was one thing I'm like, gotta beef up my resume, gotta, gotta keep moving up the ladder. So I thought it

varun_1_04-30-2025_154524 38:27

Sure,

annalyn-cruz_1_04-30-2025_154525 38:28

for that. It gave me a little bit more money. not as much as I think was deserved after looking back on that experience.

varun_1_04-30-2025_154524 38:37

sure.

annalyn-cruz_1_04-30-2025_154525 38:37

so it was more money and I was gonna be able to and hire to professional staff members.

varun_1_04-30-2025_154524 38:46

Cool.

annalyn-cruz_1_04-30-2025_154525 38:46

was exciting in terms of just like career progression and being able to have that

varun_1_04-30-2025_154524 38:52

New skills.

annalyn-cruz_1_04-30-2025_154525 38:53

Yeah, and

varun_1_04-30-2025_154524 38:54

absolutely.

annalyn-cruz_1_04-30-2025_154525 38:55

that's what was also like sold to me, right? oh, you're gonna be able to uplevel your leadership skills, you'll be able to have this huge team, not only of professionals, but of, student staff who were like paraprofessional. they were on it in terms of what they were, able to bring. I would say the difficult part was that. The full-time staff basically all left within six months of each other. Some got different roles on campus. Another person, left the state of California, right? So there was this and change that within the team that I then inherited, right? So

varun_1_04-30-2025_154524 39:39

Uh.

annalyn-cruz_1_04-30-2025_154525 39:39

Inherited all the emotions, all the feelings of change and unhappiness that some of the student staff feeling. So that was something I wasn't quite prepared for at all, how tough that was gonna be. in terms of I think a lot of challenges that I didn't foresee

varun_1_04-30-2025_154524 40:07

did that get better at all over time? What was your sense of, who were you reporting to? what was your sense of performance in that role and like feedback that you were getting?

annalyn-cruz_1_04-30-2025_154525 40:18

Yeah. I, I, I'm just like, I'm going through the memory right here in my mind. Yeah. it, to me, it felt very. Chaotic in what I was experiencing. It was, that whole saying of oh, you're drinking from the fire hose. I felt like I had eight fire hoses

varun_1_04-30-2025_154524 40:37

Yeah.

annalyn-cruz_1_04-30-2025_154525 40:38

at all times. Like it was a high pressure job, a very visible job on campus, we were welcoming all the new students and their families to campus, right? Like that was the role. And, I hadn't worked in that space before. So thinking back on that, it, it truly was change after change and managing, not just being new to role, but new to a leadership position, new to a whole new team, trying trust with these folks who lost trust in the administration. I'm using, quotations again. and so I struggled a lot. And I remember one time I just had it because I, there was, we were preparing for a huge opening the, I was just hearing a lot of complaints about how we were running things, how, our team wa was or wasn't doing X, Y, Z. I just, I remember breaking down one night, breaking down, meaning I started to cry and I was like, y'all, there is so much pressure right now about

varun_1_04-30-2025_154524 41:50

Yeah.

annalyn-cruz_1_04-30-2025_154525 41:51

to deliver in the next, like weak. and I just, and I remember feeling so mortified at the time of oh my God, I cried in front of the team. Oh my God. I probably was like, that's not what I should have done. And you know what's interesting is after I showed my own vulnerability and fear as a

varun_1_04-30-2025_154524 42:14

Huh.

annalyn-cruz_1_04-30-2025_154525 42:16

something shifted within the team. Like they softened knowing that I was struggling myself, because I think what was happening, if I look back now in time and knowing what I know about organizational change, how humans, deal with it and or not deal with it. People were in grief. They were in grief over who they thought their leadership and manager team was gonna be. They had their whole, summer mapped out of what this work would look like. then it was like the. unit, IE the people they were working with left, And for Like they, they all transitioned for different reasons. And then I was like the new guard that came in along with the two people that I hired. So we were all just trying to figure it out and and so when I think about that time, I was really trying to pretend like I had everything together, when really I didn't. And I think, and when I think about the work that I do now in terms of coaching and, providing feedback to managers and leaders about how they are showing up with their teams, I always encourage them to share some of their emotions, to share some of their struggles, right? to be a bit more human and vulnerable in the workplace, because that's actually what's gonna. allow some connection and softness. I think that we put these walls up in the workplace sometimes of, as leaders thinking like we can't show any fear or vulnerability, but that moment taught me that it's okay to do that. It's okay to share that. I don't have everything together, but we're gonna get through this together and here's what I do know, right?

varun_1_04-30-2025_154524 44:09

Yeah.

annalyn-cruz_1_04-30-2025_154525 44:12

but I was just, at the time again, being earlier in my career at that point, I just that I had to have it all together and not show any vulnerability.

varun_1_04-30-2025_154524 44:26

What was your, what, did after that moment, you you say you recall a shift, like in your team and the folks that you maybe thought I. And I'm maybe reading in between the lines here, but like maybe viewed you skeptically after all of the kind of the feelings that they had been going through in terms of like just churn and grief and not really understanding what was going on and viewing you skeptically and then with a bunch of new mandates that were different than what they were expecting to have to do. Then you have this moment where you get vulnerable with them and their attitude towards you changes. But at the same time, you are not in this moment that we're talking about. While you have this job, you don't have the wisdom that you have. Now, looking back on it to say that was actually like a breakthrough moment for me as a leader of this team and the the relationship that we had with each other.

annalyn-cruz_1_04-30-2025_154525 45:17

Yeah.

varun_1_04-30-2025_154524 45:18

at that time did you see that? Like, you, you notice it in retrospect, did you notice it at the time to the point where it was like, what were, what was going through your head at the time? Because it sounds like it was a pretty traumatic moment, like coming in from like breaking down in front of your team kind of thing.

annalyn-cruz_1_04-30-2025_154525 45:33

at first I was really embarrassed and thinking, oh shit, what did I just do? like

varun_1_04-30-2025_154524 45:37

Yeah,

annalyn-cruz_1_04-30-2025_154525 45:38

my body and my emotions took over and it just, Like I couldn't not do that. it just was a, an immediate response to all of the pressure and all of the, expectations from others that I was feeling the weight of it all, and I think I just down. Like

varun_1_04-30-2025_154524 45:57

totally. Yeah.

annalyn-cruz_1_04-30-2025_154525 45:58

it had to be released. What shifted was that I did have a few staff members come up to me, whether it was immediately after or within the week, and they said, thank you for sharing what you did. We had no idea how hard it's been for you.

varun_1_04-30-2025_154524 46:16

Yeah.

annalyn-cruz_1_04-30-2025_154525 46:16

just thought you were handling it and that, and we weren't sure about X, Y, Z. But I, I do remember that, that there was, there were some sentiments that people directly said to me of, I had no idea what you

varun_1_04-30-2025_154524 46:29

Yeah,

annalyn-cruz_1_04-30-2025_154525 46:30

with as a leader. And now I got, it was almost like, I got to see your humanity outside of your role,

varun_1_04-30-2025_154524 46:37

sure. Yeah.

annalyn-cruz_1_04-30-2025_154525 46:39

and then they just became kinder to me. I think. I think they, they had more understanding of the struggle, that I

varun_1_04-30-2025_154524 46:46

Empathy.

annalyn-cruz_1_04-30-2025_154525 46:47

and so there was empathy that happened as a result of me, sharing what was a struggle.

varun_1_04-30-2025_154524 46:57

Yeah. tell me about moving on from that role.

annalyn-cruz_1_04-30-2025_154525 47:02

Yes.

varun_1_04-30-2025_154524 47:03

it was a tough role.

annalyn-cruz_1_04-30-2025_154525 47:04

Yeah.

varun_1_04-30-2025_154524 47:05

tough when you left? Were you looking pretty quickly? What was the transition?

annalyn-cruz_1_04-30-2025_154525 47:10

the, ended up happening was that I applied to be a resident director for Semester at Sea. that was gonna be a temporary role. It was only for a semester, but it had been, a dream of mine to

varun_1_04-30-2025_154524 47:25

yeah.

annalyn-cruz_1_04-30-2025_154525 47:25

and to work for a semester at sea and travel the world. so it actually gave me, not only did I see part of the world through that experience, and it was amazing, but it also gave me that pause to think about do I actually wanna apply for the role that I left? Now that it's gonna be a full-time role, it was no longer gonna be an interim role.

varun_1_04-30-2025_154524 47:49

Ah.

annalyn-cruz_1_04-30-2025_154525 47:50

they were gonna hold my job that you, and I know me as like the academic program coordinator role. So they were holding that job for me. I think in the hopes they were hoping that I would apply for the director position, With, with new student services was the role at the time. And so I had a lot of, I think, heart to hearts with myself and with my best friend who sailed with me, who I met on the voyage and really thought, is this the path for me moving forward? it wasn't like I, it was very clear to me. And that actually was a pivotal moment because that's what led me to then go into learning and development, which is the latter part of my career that I've continued to do since 2012.

varun_1_04-30-2025_154524 48:42

Was there a role that was open at the time? Was learning and development something that you had been thinking about for a while?

annalyn-cruz_1_04-30-2025_154525 48:47

I had done, it's funny because I had actually done learning and development or l and d in, different aspects of my career within student affairs. It has always been about learning. It has always been about development. Coaching, facilitation, right? Like it wasn't a huge leap. What was different was that this role would have me working directly with staff, unquote the adults versus the college students. so that was actually a big, pivot point for me because as I mentioned, up until that point, I was always working for the most part with college students. and of the reasons why I wanted to move into learning and development for the staff was that saw how much those folks needed help, who were supporting the students, right?

varun_1_04-30-2025_154524 49:46

yeah.

annalyn-cruz_1_04-30-2025_154525 49:47

I'm like, oh, I needed someone like who was in l and d to help me with what I was going through in that last interim role. And so I

varun_1_04-30-2025_154524 49:57

Yeah.

annalyn-cruz_1_04-30-2025_154525 49:57

to think, okay, this'll open up a door for me, beyond maybe working at Cal, right? there's a lot of learning and development or l and d functions in any company, in any organization. Not always, but I thought that this would be, a door opener for another career, pivot.

varun_1_04-30-2025_154524 50:23

Yeah, absolutely.

annalyn-cruz_1_04-30-2025_154525 50:25

Yeah.

varun_1_04-30-2025_154524 50:26

cool. Te tell us about the role. Oh, yeah, go ahead.

annalyn-cruz_1_04-30-2025_154525 50:29

just about to go there. I was like, you know what was

varun_1_04-30-2025_154524 50:31

I.

annalyn-cruz_1_04-30-2025_154525 50:32

too about my decision at the time was that, it was a project analyst role within the l and d, department within student affairs and. I remember thinking to myself, do I take a lower position versus a director position? So organizationally, pay-wise, et cetera. director role was, better on paper, knowing where I wanted to go and what I was curious about, it wasn't in alignment. So I'm like, I will take the lower paying job. I will take the quote unquote lower title in order for me to really explore if this is the right path for me. I'm so glad that I did it a hundred percent.

varun_1_04-30-2025_154524 51:22

I think that's really important. I. Find that it's very difficult to make a decision like that, like personally speaking. And for most people that I talk to, like there is this sense that taking a pay cut or title cut or both at the same time, is a lack of progress or a setback in itself. Whereas I think what I'm hearing from you and what I'm starting to I think I think most people know this literally, right? Like they can, like concept, they understand the concept that those things don't necessarily mean you're taking a step back if it's in service of progress you're making in other areas of your life and career.

annalyn-cruz_1_04-30-2025_154525 52:03

Yep.

varun_1_04-30-2025_154524 52:04

but, I think it's really, that's really awesome that you did this. and it's not like you, at this point in time in your career, you were in higher ed, you are like, several years out of grad school at that point. How did, you look back on it, it was a great idea.

annalyn-cruz_1_04-30-2025_154525 52:19

Yep.

varun_1_04-30-2025_154524 52:20

I can't imagine it was like an easy decision to make from like an ego perspective.'cause we all have egos and

annalyn-cruz_1_04-30-2025_154525 52:28

Oh

varun_1_04-30-2025_154524 52:28

yeah.

annalyn-cruz_1_04-30-2025_154525 52:29

love that you bring that up because it really was, like I said, had to think long and hard about whether this was something I wanted to pursue. Because you're right, the ego in me and also just even what I was hearing from other people, they're like, are you sure you wanna take a step down into taking an analyst role versus a director position? I just said. My heart and my spirit's calling me to something else and this feels like the right path for me. I also knew, who my boss was gonna be, and I knew who my colleague and my teammate was gonna be, and I respected and admired the two of them. Still do to this day so much. And

varun_1_04-30-2025_154524 53:14

Yeah.

annalyn-cruz_1_04-30-2025_154525 53:15

like they were going to help develop and grow me and gimme the support that I may not necessarily have gotten in the other role.

varun_1_04-30-2025_154524 53:24

Yeah. And these were folks that you had worked with before.

annalyn-cruz_1_04-30-2025_154525 53:28

tangentially. Yes.

varun_1_04-30-2025_154524 53:30

Okay, got it. Yeah.

annalyn-cruz_1_04-30-2025_154525 53:31

Yeah. And so that was the other thing too. my, my soon to be boss who ended up becoming my boss at the time said, look, it's an analyst role. I wanna grow this team. I see this happening in the future, but I can't guarantee it. I do see you as having the skillset as one of the organization consultants on the team. we ever grow the team, I like, I wanna develop you and I wanna give you opportunities even though you're an analyst, to still put you in front of the room, to still have you facilitate, to not just have you do our admin and our finances, but this is a strategic move for me and for you moving forward. if you say yes, right? And I just again, trusted. I was like, yes, this is what I'm gonna do and I'm gonna learn on the job and I'm gonna get better at learning what, learning and development is all about and absorb as much as I can. I just trust that the right opportunity will open up. And eventually it did. I became a consultant on, on that team in the last few years. I was working there.

varun_1_04-30-2025_154524 54:44

And what did that mean in terms of becoming a consultant on that team? how did your role change? Were you reporting to the same person that convinced you to come on and help you grow in that role?

annalyn-cruz_1_04-30-2025_154525 54:54

I was reporting to the same person. It meant one higher pay, higher title, of course.

varun_1_04-30-2025_154524 55:00

Great.

annalyn-cruz_1_04-30-2025_154525 55:01

and it also meant that we could hire someone else to do the administrative work, the financial advising, the, website design, all these things that like I could do and I did do them, but that's not my bread and butter. that's not where I excelled. It's like I ended up excelling in, I. A lot of the other things that, like I'm currently doing right now, it's the consulting work, it's the facilitation, it's the program design, it's the, influencing leaders, right? that's what I ended up doing more of and focusing on that versus having to juggle both the administrative and

varun_1_04-30-2025_154524 55:42

So

annalyn-cruz_1_04-30-2025_154525 55:43

consulting

varun_1_04-30-2025_154524 55:43

when you were a project analyst, you were doing more of like just admin stuff versus when you were actually a consultant? like how did that cha you were actually like leading programs, hiring people to take over the admin stuff that you were doing? Talking to leaders, more, and like actually doing trainings.

annalyn-cruz_1_04-30-2025_154525 56:01

I would say I was do, if I had to give a percentage, it was like role was maybe 40 to 50% with the rest, the consulting role. I just wasn't getting. the title for it, right? So

varun_1_04-30-2025_154524 56:16

Right.

annalyn-cruz_1_04-30-2025_154525 56:17

it was strategic in the sense of let me just do what a normal consultant would do on top of the other things that were expected of me in the analyst role.

varun_1_04-30-2025_154524 56:29

Gotcha.

annalyn-cruz_1_04-30-2025_154525 56:30

and so yeah, that's what ended up happening. And then we were

varun_1_04-30-2025_154524 56:33

Yeah.

annalyn-cruz_1_04-30-2025_154525 56:33

find an amazing person who took over the analyst role and was with our team the rest of the time that I was there.

varun_1_04-30-2025_154524 56:41

That's wonderful. te tell me about how your time wrapped up at uc, Berkeley, and, let's talk about what came next. what were, what was telling you your season and at Cal was coming to a close and what were you looking to do? You

annalyn-cruz_1_04-30-2025_154525 56:53

It was twofold. I, and I think it one. At the time, the campus was really struggling financially, so there were some layoffs that were happening us being within l and d, we saw the writing on the wall. We knew that was, something that was gonna happen. And we knew also that within l and d that's sometimes the roles that end up going away, right? so that was one thing. The other factor was, again, I was getting curious about what would life be like outside of higher ed doing this work now

varun_1_04-30-2025_154524 57:29

Yep.

annalyn-cruz_1_04-30-2025_154525 57:29

learning and development in a corporate space. So I had a former colleague who used to work at Cal, who ended up, at ea and she referred me to the role. And, one thing led to another and I ended up getting that job, in the midst of. my role within l and d at Cal being eliminated.

varun_1_04-30-2025_154524 57:53

Okay. All right.

annalyn-cruz_1_04-30-2025_154525 57:55

two factors. One, there was again that curiosity of could I do this in a corporate space? what would that be like?

varun_1_04-30-2025_154524 58:03

of the reason you were excited about going into learning and development, right? to open up more avenues for you, not necessarily corporate or someplace like ea, but it's like, Hey,

annalyn-cruz_1_04-30-2025_154525 58:11

Absolutely.

varun_1_04-30-2025_154524 58:11

a place where I can actually be of service and like helping people like go through like a transformation and have an actual result in their lives that can be applied beyond the higher ed space, in a way that student affairs, couldn't. Very cool. Yeah.

annalyn-cruz_1_04-30-2025_154525 58:27

and thinking back on that time, I'm so grateful for the l and d role I had at Cal because that opened up a door, right? that opened up a door to other corporate spaces that were like, oh, you've done this, you've just done it. Within higher ed, being in student services. Like sometimes people don't always see the connection, even though there totally is. But

varun_1_04-30-2025_154524 58:51

Yeah.

annalyn-cruz_1_04-30-2025_154525 58:52

jump for me to make

varun_1_04-30-2025_154524 58:54

It's like the name of the department exists in corporate, so like, that like helps, right? Yeah. I mean, you know, tell us about your time at ea. You were there for several years. what did you like about it? What did you dislike?

annalyn-cruz_1_04-30-2025_154525 59:05

I was there for five years. that was a huge learning curve for me that first year. as you can imagine, it was a much faster pace than, than being in higher ed. And I worked for a global company, right? So not only was I supporting those at headquarters, but I was supporting folks in Sweden, folks in Shanghai, right? Like we had studios. All over the world and, and the projects that I was working on. Funny enough, my first project was working, totally revamping our onboarding program across the globe.

varun_1_04-30-2025_154524 59:45

Okay.

annalyn-cruz_1_04-30-2025_154525 59:46

being onboarded myself. So it was a, oh wow, okay. I'm here and I'm doing this. And I, I ended up being thrown in the deep end of the pool there because, at the time the colleague that was working on it, had some medical issues, had to take some time off.

varun_1_04-30-2025_154524 1:00:05

Um,

annalyn-cruz_1_04-30-2025_154525 1:00:05

the lead of this, this program that I was still onboarding myself to, and then suddenly taking a bigger leadership in, in that. And so when I look back on that time and that first year, I was super stressed out because I had a lot of my own inner critic and my gremlins as I like to call them, my

varun_1_04-30-2025_154524 1:00:28

Uhhuh.

annalyn-cruz_1_04-30-2025_154525 1:00:29

were in full effect of,

varun_1_04-30-2025_154524 1:00:32

Okay.

annalyn-cruz_1_04-30-2025_154525 1:00:32

am I cut out for corporate? Do I know what I'm doing? Oh my gosh, what if they made a mistake? Like had so much running through the back of my head. and at that point in my career, I didn't wanna say when I was or if I didn't know an answer. I'm like, you can't say that You don't know an answer. so my manager and I at the time, we had a lot of heart to hearts and getting to know each other in a very stressful environment of, okay, I know that you're brand new. We also have, this design work that we need to do and implement and get out there in the world. it was just, it felt very high pressure, for me in that first year. but I learned a lot, like I learned a ton and I was glad that I made the move. And also after a few years I kept dreaming. And again, getting curious about what would this be like if I did this on my own?

varun_1_04-30-2025_154524 1:01:36

was the manager that you mentioned, it sounds like you guys got pretty close. was that, I would love to know more about that relationship, especially as you were it sounds like you were drinking out of more fire hoses, with your first time in the job.

annalyn-cruz_1_04-30-2025_154525 1:01:49

Yeah.

varun_1_04-30-2025_154524 1:01:51

and was that the person that you reported to the whole time? I'm curious about the kind of all of the stakeholders involved, how your. how your experience of the role and the role itself maybe changed over your five years there, and how that led you to the moment where you were thinking about, what comes next, before you started your own business.

annalyn-cruz_1_04-30-2025_154525 1:02:09

yeah. we ended up having a really great relationship in the five years that I was there. And her, she would say the same thing. We both have said we struggled that first year together.'cause we were

varun_1_04-30-2025_154524 1:02:20

Yeah,

annalyn-cruz_1_04-30-2025_154525 1:02:20

out each other's personalities. we were trying to figure out like. What type

varun_1_04-30-2025_154524 1:02:25

I,

annalyn-cruz_1_04-30-2025_154525 1:02:25

support I needed, what type of support I needed from her and for me to actually verbalize that,

varun_1_04-30-2025_154524 1:02:32

Yeah.

annalyn-cruz_1_04-30-2025_154525 1:02:32

and so I think that was a big growth edge for me was how do I advocate for myself? How do I share when I am struggling with something or when I need additional healing? something that, that I like a Filipino, Asian American woman, we didn't really talk about that stuff in my family, right? Like

varun_1_04-30-2025_154524 1:02:56

Yeah.

annalyn-cruz_1_04-30-2025_154525 1:02:56

something that I learned, growing up. So I really found my voice, we ended up like having a really great relationship over time, but we had to work to get there. I

varun_2_04-30-2025_172550 1:03:10

at some point you end up wrapping up your time at ea. tell me about what that was like, what you were feeling about at the time, about why you wanted to move

annalyn-cruz_2_04-30-2025_172551 1:03:18

Yeah.

varun_2_04-30-2025_172550 1:03:19

and what you were drawn to doing next.

annalyn-cruz_2_04-30-2025_172551 1:03:22

I was really wanting to work for myself actually. something that I felt within myself after a few years of working there, maybe like year three or so, is that I started again getting curious. What would it be like if I actually. did this type of work, but within my own business and in a way that felt more true for me in a way that I could serve those who I really wanted to, focus in on. And and it was a hard, it was a really hard decision because, Actually, right as I gave my notice to my manager at the time, she said, oh, I was just talking about how we can continue to develop you and move you into a bigger role, right? and to move you into more of a leadership role. And I gotta be honest, when I heard that, I thought, shit, am I making a. Stake, right? I've worked for a great company, I have a cool boss. I love my team. And so it wasn't, while I knew within myself, it was a clear You're doing this, it's the right thing for you. It was, I love the people that I worked with. I felt like I was doing valuable work. And yet it, it's like a relationship. Like sometimes it's just not enough, right? there's just something else that's calling you forth or something that, you may not know what's out there in the environment.'cause again, I was just building a business and didn't know what the, what the end was gonna look like or what it was even gonna be about. I don't come from a family of entrepreneurs. so it, it was a quote unquote risky move, but again, I just felt like I can come back to a job where I get a W2, like I could do that again, and just trusted that if this dream is popping up for me, it's almost like I have a responsibility to myself to pursue it.

varun_2_04-30-2025_172550 1:05:29

tell me about the journey of, starting your business and, how it's been so far. I know you're, you've also have a, you've got a nine to five on the side.

annalyn-cruz_2_04-30-2025_172551 1:05:37

Yeah. so starting it, I didn't completely know what I was doing, but I found a couple of coaches, that I. Helped me along the way that told me, what it meant to start an LLC in California and what it, things to, to be mindful of as one begins their entrepreneurship journey. And now, and I got lucky, or I don't know if it's lucky, let me say this. I think I've built enough, Professional and personal relationships in my life to pull from, that network of people who believe in me, right? And who know have experienced my work. Whether it was at Cal or in at UCSB or in other spaces that I've been in. So that first year, a lot of my business was based on the relationships and the referrals that I ended up getting right. From people who have just known me from the past. And that was really great. I got a couple of other, Other sort of contract roles based on LinkedIn and, reconnecting with people And yeah, as you shared, I'm back at working, full-time and holding my business, currently, and Part of what I've had to learn is how to juggle both. So after I stop this interview with you, like my mind is, okay, I gotta go back and continue to design this new program that's gonna be launched within my business. which is not a small undertaking, right? it's like something I'm doing on top of having that W2 and having a role that, That I do get to go do good work in, right? Like I do get to, have a lot of, I think, good relationships with my manager and with the clients that I serve. And yet again, I still have this push pull. I would say the pool is to continue my business and to continue to run it in a way that. feels really fulfilling to me. it's purposeful work. It's what I'm meant to do in this lifetime. So for me, really focusing on women of color, who are solo, who are child-free, and building something, building a program that I wish I would've had at 25. Put it to you that way,

varun_2_04-30-2025_172550 1:08:01

I'm always curious about. How you see your sense of identity and like sense of purpose, tied to your vocation or your work? I find that I struggle to invest in things like what I'm doing now or like the career coaching or something like that.'cause I do feel like a, like I personally feel very called to that kind of like people oriented, social oriented, kind of work, right? To, to some degree. Like I wanna help people with their own transformations one way or another. but I also like to have a little bit of stability until it feels stifling. And at the same time, when I end up in that situation where I have a job, it I'm not a big, I'm not a big quiet quitter or like half aser. I very much end up Making whatever. I do a big part of who I am and then it ends up taking over. How do you find balance when you have a full-time job as well as something that is like your kind of like core mission that you've built up into a business?

annalyn-cruz_2_04-30-2025_172551 1:08:57

It's not always easy, but I think that I have practices in place now where, for example, I'm carving out my mornings and like end of day to work on my business. and if it ends up being that, I work even later, like last night, I was working on my business from five to seven 30. Originally I was allotting like five to six 30, but I was enjoying what I was doing. And it's for me, it's knowing that I'm building towards a bigger dream. And so that allows me to continue to work on it. and I would say to your point of, oh, it ends up taking over my life. Work can, I've gone through burnout before, like that happened a few years ago. and I told myself, I am not my job. it's a part of who I am. I have interests outside of my job. I do a lot of my own development, whether it's within like energy or spiritual work, whether it's through, learning some new tools, new assessments that get me to be a better coach and facilitator and. When I'm with friends, I'm like, let's not talk about work. I just, I'm more boundaried around when it takes space in my life, if that makes sense. And as a coach, I'm always so curious like. Yeah. what was it like to be with your family for the first time after doing this one amazing leadership development retreat that you did? I'm not so interested in someone's day to day work like, and the minutiae to, it's get me to that deeper level of. Why you do what you do and tell me about this painting that you just did. I'm just curious about stuff outside of the work that, that we do day in and day out and Yeah, I guess I'm just like more boundaried around that nowadays.

varun_2_04-30-2025_172550 1:10:59

I think we see the story of how your career has brought you to this point. but I'd love to know a little bit more about your practice and how it might look different for each person. And what are the kind of like common threads that are shared across them.

annalyn-cruz_2_04-30-2025_172551 1:11:12

some of my individual coaching clients end up just being women of color who are in the mid to senior level, or they might be transitioning to retirement. So they often reach out to me when they're like, I have this big dream, or I'm going through a big transition. I'm moving into a leadership role, or I want to be a keynote speaker. Or, I'm trying to find more fulfillment in my life. these are some common themes of what people often, search for when they're looking for a coach when I'm looking for a coach as well, yes. I'm looking for certain skill sets and I'm also looking for someone who can. Who I could also identify with, right? Who may have similar, backgrounds and experiences and can take me through a transformation myself. That's what I'm hoping that I'm doing for my clients in terms of, I. That inner work that often prevents us from really living the most like full and fulfilled lives that we can. And for me, I'm really trying to focus in on, a population that isn't often talked about. I think there are a lot of coaches out there who support moms, for example, which is phenomenal. And for those of us who aren't in that camp, I think we have different needs and wants and desires. and I'm curious about what it's like to, to have a more focused program. For those of us who are living lives similar to me, because I do have that lived experience. I do know what it's like, to live in a world where your life experiences may not fit with the majorities. So you know who better than to serve those folks than people like me, because I, again, if I had a coach who, was offering what I'm about to put out there in the world, I'd be like, yes, that sounds like something that I need, that I want, that I wanna be in community with other women who are struggling with the same things I am or who have bigger dreams that. that don't necessarily equate to, to motherhood, right? Like, that's what I'm hoping, for the near future is that I am that person for those child-free solo women of color who are really looking to find a new path for themselves.

varun_2_04-30-2025_172550 1:13:45

any final words of advice that, you would give to anybody looking to make a change in their career or maybe find themselves at a crossroads?

annalyn-cruz_2_04-30-2025_172551 1:13:52

follow the curiosity, right? You owe it to yourself to follow the curiosity that's blooming within yourself. you don't know what path it's gonna lead you to. and the other thing I would say is to really trust within yourself and to trust within your intuition to know that not everything is gonna be perfectly carved out for you. and having that faith within yourself that. Things will unfold magically the way that it's supposed to and getting the help that you need, whether it's through coaching, therapy, supportive friends and family who will be your hype crew and tell you, you absolutely got this. people in your corner who are cheering you on, who are, telling you that you are absolutely capable of what's next. these are some of the ingredients and the recipe that I think we all need when it comes to making big transitions in our lives.

varun_2_04-30-2025_172550 1:14:51

it was a pleasure getting to reconnect and obviously. So glad that we met however many years ago when I was a student and you were able to, be someone that provided that guidance to me when I was younger.

annalyn-cruz_2_04-30-2025_172551 1:15:02

Yeah.

varun_2_04-30-2025_172550 1:15:02

to share with, my audience on my podcast, so this is really nice.

annalyn-cruz_2_04-30-2025_172551 1:15:07

Thank you so much for inviting me. It was fun. Thanks.

1:15:17

Really hope you enjoyed that conversation. There was so much that I got from that discussion and looking back on it. One of the things I appreciate so much about her is that she was willing to take risks and trust herself and have faith that it was gonna work out at the end, but at the same time be able to make sure that those risks are calibrated. She took what resonated with her the most and turned that into calibrated risks for new opportunities. Sometimes she would jump somewhere with no job lined up. Sometimes she would be willing to actually take a step down or step back in the organization that she was working with. She did this at uc, Berkeley, uh, because she knew that taking that step back would allow her to get on the long-term track that she actually wanted to be on. She would not have had these successful. Corporate career in learning and development, were she not willing to put her ego aside and take a step back and do that? So thank you so much for joining me again on the Push Pull podcast and I will see you at the next one.