Rashida Bradley (00:00)

You have to get over that hurdle of perfection because you need to let people see you trying.

You’re working through the problem, you’re getting to that level and you're becoming the master.

Kelly Dwyer (00:45)

Today, we're thrilled to welcome Rashida Bradley. Rashida is a leading operational strategist who drives financial and transformational initiatives for Fortune 50 companies. She's currently the lead director at CVS Health, where she oversees financial strategy and operations, helping advance innovation in the pharmacy business. Rashida's unique blend of analytical rigor and heart comes from her background as a former investment banker turned healthcare strategist. A proud New Yorker, she's also a wife, mom of two and a growing enthusiast on the tennis court.

Welcome Rashida.

Rashida Bradley (01:21)

Thank you, thank you, so happy to be here, Kelly.

Kelly Dwyer (01:24)

We're so happy to have you here. Okay, I have a quick question about tennis.

Enthusiast on the tennis court, what is your favorite shot? Is it a forehand? Is it a backhand? Is it down the line? Is it a serve?

Rashida Bradley (01:35)

It's definitely a cross-court backhand. Yes.

Kelly Dwyer (01:38)

Okay, I love that you lit up when you said that you knew exactly what your answer was. That's fabulous.

Rashida Bradley (01:44)

Absolutely.

Kelly Dwyer (01:46)

Well, thank you so much for being with us today. We are excited to hear from you and hear you share your wisdom. So where do you want us to start today?

Rashida Bradley (01:53)

Thank you. I would love to start with the title of your podcast which really inspired me in terms of thinking about all the pivots and turns that I've taken in my career and life to get to the bio that you read today. I’d love to share the story of a career pivot where I decided to apply for grad school and had a surprise along the way. I reached an opportunity, a moment in my career at CVS Health where I wanted to reinvest in myself and take things to the next level as an ambitious career go-getter. I found a great program at Cornell University where they offered a dual degree and an MBA and a master's in healthcare policy and research. I thought that I would really build the perfect network to really advance my ambitions as a healthcare professional. And with that, decided to apply early decision, met all the right folks in terms of faculty, administrative staff, had all the calls and coffee chats that you would to really feel grounded in my decision.

I remember receiving my acceptance email at a friend's house, completely lit up, jumping up and down, shared the moment with the friend and her mother as we were celebrating a milestone of hers. And it was just such a joyous moment, just feeling that I'd made the investment and was going on this track of really growing my career and my investment there at Cornell.

And then I would have to say Kelly, later, I received a positive pregnancy test. And so instantly thought. Wow, life offers you very unique decisions to make in terms of choosing between life and career. I had made the very keen decision to choose both. And so I pursued both my program at Cornell and I had my son during the program. So, you know, with that, I'm sure we'll get into it. There were lots of challenging moments of reflection in terms of was it the right decision? How could life throw this curve ball at me at a time when I thought I was on a specific track?

I think many women, as we encounter these pivotal points in life and when they have to make certain decisions that may be better for one or the other.

Kelly Dwyer (04:24)

Wow, that's some news to get. Here you are thinking, all right, I'm heading for graduate school. I'm going to get a dual degree, come out with my MBA and a Master's. ⁓ shoot, I'm pregnant.

Take us to that moment where you found out, that moment of like emotional collision was there a moment in there where you felt, my God, I can't go to school anymore!

Rashida Bradley (04:50)

Family has always been first and priority for me. I've been in a long-term relationship, married my college sweetheart. So he's definitely been on that career journey along with me. Both were finance majors, both in investment banking. So we have a great rapport and bond in balancing family and life.

And so I felt it would be selfish of me to try to pursue graduate school, but he was definitely one of my biggest advocates in figuring out how could we do this. At the start of the year before, you know, entering school in September, I was thinking about how we're going to do this. And I feel like there's no real plan that you can put in place to anticipate all of the curves that motherhood can throw at you.

And so I started the program in September. I had my son later that year, I know my biostats professor, if she ever hears this podcast, she'll laugh because I asked for an extension on

exam.

Kelly Dwyer (05:48)

my God. I would hope you did.

Rashida Bradley (05:51)

I did, I did. So, I think I had to redefine ambition for myself. I had to learn how to give myself a little more grace in terms of not pursuing perfection, focus on excellence. I knew that I was motivated by, what I wanted to accomplish in my career within the healthcare industry. I was aligned in what I was pursuing. And I think that's important in terms of thinking of achieving the right balance with life and not being overburdened by what may be perceived as an obstacle.

Kelly Dwyer (06:20)

what a story, what a story. This was child number two. So you had a sense of..

Rashida Bradley (06:25)

Yes.

Kelly Dwyer (06:26)

What was coming.

Rashida Bradley (06:28)

Yes.

Kelly Dwyer (06:28)

Now, of course, I hear going from one to two really changes the dynamic a lot but you had a sense at least for what that first year might be like with a newborn, both you and your husband had some experience to draw from in making your decision.

There was this book I read a few years ago. The Feminine Mistake. And I remember the author in that book shared a perspective…

Rashida Bradley (06:46)

Hmm.

Kelly Dwyer (06:51)

A career is really long, 50 years.

Rashida Bradley (06:54)

Yes.

Kelly Dwyer (06:54)

Raising a child, 18 years. And so, you think about your career being that long and you're an ambitious, professional woman whose career is important to her, family obviously is important to you as well. But being able to do both and making space for both just recognizing that, okay, I'm still gonna want a career when my child leaves the house or when my children leave the house. So…

Rashida Bradley (07:18)

Yes.

Kelly Dwyer (07:19)

if that's the case, do we need to do now so that I can be there.

So you made the decision, I’m gonna go to business school, I'm gonna get my degrees and I'm gonna have a baby. I'm doing it.

Rashida Bradley (07:33)

Yes.

Kelly Dwyer (07:34)

And you said your husband was very supportive of that decision. Tell us what kind of pressure that put on the family? Anything else that you needed to consider as well?

Rashida Bradley (07:43)

I think I was definitely in hindsight in denial about a lot of things and probably just an optimist at heart wanting to focus on the achiever in me and what we can achieve, I guess, as a family and my mother-in-law was actually diagnosed with cancer during that time as well.

And so she was working through her diagnosis and treatment plan leading into me applying for grad school and then finding out that I was having my second child that also put a big strain on our family. I'm an only child. My husband is an only child now, but his brother passed from cancer when he was a teen. And so...

that took a big toll on our family and thinking about how we balance and her treatment plan along the way. So I would say I was definitely, I think, in a state of denial, thinking that things would work out for the best.

But it was definitely a very difficult period for us holistically.

Kelly Dwyer (08:47)

so your mother-in-law was going through cancer, you decided to apply to school, then you found out you were pregnant, and you made the decision to continue moving forward with school. So then what was the outcome with your mother-in-law?

Rashida Bradley (09:01)

We actually lost her. The timing is something I haven't really disclosed but given what we're discussing today, we actually lost her the day that I gave birth to my son. And so that was also a very difficult time for us as a family and it was also mixed with this deep grief and pain along with the joy of bringing a new person into our family.

And so that date is very challenging for us as a family, but I think we've been able to manage it in that we celebrate her life on her birthday and all the joy that she brought to our family. had a very unusual relationship. We were very close. As I mentioned, my husband and I were college sweethearts, so she was definitely a second mother figure to me.

And then we celebrate my son's birth on his birthday instead of thinking of the grief and loss on that day as well.

Kelly Dwyer (09:59)

so you celebrate your mother-in-law's birthday on her birthday. You celebrate your son's birthday on his birthday. Aww. Yeah.

Rashida Bradley (10:05)

Yes, just to keep that date for him because we don't want to shadow his celebration with the loss of my mother-in-law to her brain cancer on that date.

Kelly Dwyer (10:16)

Yeah,

yeah. what a tough situation.

Rashida Bradley (10:21)

Very tough, very tough.

Kelly Dwyer (10:22)

Our values can help us make decisions when we're clear on our values. I'm curious,

Rashida Bradley (10:28)

Absolutely.

Kelly Dwyer (10:30)

you were in this season of life dealing with family loss, grief, also dealing with a newborn, and you're in a dual degree graduate school program, which

Rashida Bradley (10:37)

Mm-hmm.

Kelly Dwyer (10:41)

alone is a lot, now were you continuing to work at the time?

Rashida Bradley (10:44)

I eventually returned to work maybe about six months after having my son. Yes.

Kelly Dwyer (10:49)

Okay, all right, so then you were also juggling a full-time job.

my Lord. What, ⁓ my Lord, seriously. Wow.

Rashida Bradley (10:52)

Correct, yes.

I'll put it all in the book, Kelly, when I write the book of my life.

Kelly Dwyer (11:03)

When we're clear on our values, they really can help us know what to say yes to and know what to say no to. I'm curious…

Rashida Bradley (11:09)

Yes.

Kelly Dwyer (11:11)

What value, what one or two values, were you really embodying in that period of time?

Rashida Bradley (11:17)

one value that I leaned into focused on community and building support systems. And really value friends, family, and mentors who were there in times of joy, celebration, but also stress and grief. And I think that definitely helped me to focus on my core values of health and wellness in the work that I was doing, why I was motivated to continue to do my dual degrees and really still lean into my family. And I think with that focus, everything else, it just falls to the wayside and just feels like fluff and distraction when you know exactly why you're there and why you're pursuing the things that you're pursuing and the time that you're investing. I definitely give a shout out to my community and the support system that I was able to build along that journey.

Kelly Dwyer (12:15)

Obviously your husband's a part of your community. You said family and friends. Tell us, give us more specifics. If someone is thinking,

Rashida Bradley (12:19)

Yes. ⁓

Kelly Dwyer (12:22)

I really need to focus on building community, how do you build community?

Rashida Bradley (12:28)

Sure, and I think that comes with a certain level of self-awareness and understanding where you have vulnerabilities, weaknesses, and how do you gather support for getting to that next level or going through maybe some difficult stages in life.

I’ll give a perfect example. I'm working through biostatistics and I know I need to study. I know my daughter has all the lessons of the world because my husband wants her to be a well-rounded individual. So, you know, I'm leaning into my mother to help support taking her to violin lessons, taking her to tennis practice. My husband is, number one dad taking care of my newborn. And, I'm able to basically laser focus on the task at hand without feeling that I'm dropping any of the balls that are necessary to balance as a working mother and overall ambitious professional.

I would say that, I always advocate for women empowerment, you know, career balance, but mental health and building community helps to keep those things in line that's why I would say that's one of my values and how I'm able to lean into that support even from a professional and academic lens.

The few folks that I did entrust that level of vulnerability were also very supportive in terms of help stand up the team that I was leading my organization and knowing that I needed to achieve a level of balance in my work and academic life in order to complete my degree as well. As a leader, being transparent and vulnerable in some of those challenging you'll see who steps up who really does support you along that journey through those different phases and leaning into

those things I was able to, I would say, accomplish my goals.

Kelly Dwyer (14:12)

you mentioned having support at work, the importance of being vulnerable with trusted individuals at work, was part of that vulnerability also you making a specific request or was it like, hey, here's my situation. ⁓ Can we talk about how to work through it together or here's my situation and here's my request for you.

Rashida Bradley (14:33)

One mentor mentioned in order for us to be successful, any professional to be successful, we have to be helpable and people need to know how to help us. And so I'll give a perfect example as I was returning to work had gotten out that I'd applied for school and I was obviously looking for career. I was tasked with leading a new team. And so with that, I thought, well, I'm accelerating at work. I'm building out a new team. And my direct leader knew that I was a new mom as well and working through my program. Not directly, it wasn't something we'd discuss on a normal basis, but he knew enough about me as a leader, the things that I was balancing to know where he could step in and help support to invest in my career.

And so that I'm forever grateful for. And I think I lean into maybe some of the work that Brene Brown shares, in terms of the importance of vulnerability as a leader, because it makes you relatable and you are more human to the team that you're working to lead. And so I think that's also a very important quality that I lead with.

Kelly Dwyer (15:38)

That's a great point you just made about also being vulnerable to your team, the people you're leading, because it makes you relatable, which

Rashida Bradley (15:45)

Yes.

Kelly Dwyer (15:48)

I wholeheartedly agree with. How do you strike the balance of being vulnerable enough without oversharing?

Rashida Bradley (15:54)

It’s something that I work through. I feel maybe I'm on the younger end as a people leader. in just a team meeting, sharing that I'm a mom and fun things that I do with my kids on the weekends related to their sports or activities, I think builds that connection and also adds a little light on that person is outside of roles and responsibilities. So I think that's important in terms of building trust.

We talk about it often at work, but psychological safety, because it’s very necessary to really build the cohesion on a very diverse team. My team works in office we work hybrid. And so it's important to, I think, make those connections and investments.

Some folks know who you are and can relate. And I think the diversity of my team also lends to it as well, because although I'm a growing tennis enthusiast as we shared, a member of my team who is into nutrition and health. So we relate on that level. And we talk about the different recipes that he works on on the weekends as an aspiring chef.

And then there's another member of my team who is an avid hunter, something that I don't think about as a native New Yorker and talking to him helps open my mind as well to what his weekends may include that don't necessarily connect back to my city life.

So I think it's really important to build those connections and I think it strengthens your team. And then as a leader, you feel that you can invest in that talent and support you in terms of the work that you're leading within an organization.

Kelly Dwyer (17:28)

Yeah, love how you mentioned diversity in the way that you mentioned diversity. It's almost like a diversity of lifestyle. Yeah, yeah,

Rashida Bradley (17:35)

Yes, yes, exactly,

Kelly Dwyer (17:37)

We're here in Colorado, so we have hunters here too.

Rashida Bradley (17:39)

Okay.

Kelly Dwyer (17:43)

I want to circle back real quick to when I asked you the values question and you shared community, you also mentioned your passion and value around health and wellness and the situation that you described. You were in a crucible. my gosh. So much pressure.

Rashida Bradley (17:53)

Yes.

Kelly Dwyer (18:00)

you talked about helping with the mental health piece.

Rashida Bradley (18:03)

Yes.

Kelly Dwyer (18:04)

What about physical health or managing the stress? Is there a go-to practice that you have or that you used in that period of time?

Rashida Bradley (18:12)

Yes, I think mental health is very important. We talked about it often in my program, actually. We had many subject matter experts on the subject who were thinking about how we can accelerate that platform and really help patients more. And even in my own practice I use an app called Headspace. And I really try to regularly meditate to balance a lot of the stress or anxiety that can build up with these high pressure situations, balancing work and life, intense deadlines.

I wasn't great about self-care and now as I've picked up tennis, that has been my physical form of investing in self-care.

Kelly Dwyer (18:56)

So you use Headspace guided meditations or do you just, okay. And do you do five minutes, 10 minutes,

Rashida Bradley (18:57)

Yes. Yes. Guided meditations.

Kelly Dwyer (19:03)

every day?

Rashida Bradley (19:05)

Every day in the mornings,maybe around 6 a.m. because that's before the morning rush with the kids and the lunch boxes and getting to school. And that really does help keep me balanced.

Kelly Dwyer (19:17)

so it helps with the stress management and balance.

Rashida Bradley (19:19)

Yes.

And balance. Yes.

Kelly Dwyer (19:23)

If your son listens to this one day,

Rashida Bradley (19:26)

Mm-hmm.

Kelly Dwyer (19:27)

What do you hope he hears about who his mother is or was in that time?

Rashida Bradley (19:33)

Wow, that's powerful. I would love for him to know that I am a person who is pursuing excellence and not perfection. And I had to become that person. When you're an academic and you're in school, you think, okay, I study, I get the A, it's perfect, put a bow on it. But with life being very messy, you have to accept that everything will not run perfectly or smoothly. I want him to know that that's the essence of who I am and also that I chose him. I wanted to build this life and balance with my ambition. We're for the better for it.

Kelly Dwyer (20:16)

warms my heart. I hope he does hear this one day.

Rashida Bradley (20:20)

I do too, I do too.

Kelly Dwyer (20:22)

You said you had to become that person who pursues excellence and not perfection. How did you make that shift? Because I know there are a lot of people out there trying to make that shift for themselves.

Rashida Bradley (20:34)

it brings me to a book that a mentor suggested to me and I've read it a few times now. It's Drive by Daniel Pink. Do you? I love that book and I felt it really captured so many things that I felt were floating in my

Kelly Dwyer (20:43)

I love that book. Yes. Yes.

Rashida Bradley (20:52)

One thing they talked about in the book is about mastery. And I thought about that, You have to get over that hurdle of perfection because you need to let people see you trying. You’re working through the problem together, you’re getting to that level, and you're becoming the master. But you've never mastered it fully. So I take that approach in the work that I'm doing and in motherhood.

Kelly Dwyer (21:16)

I love that. I might like pull a little bit of that as a mantra for next year. You need to let people see you trying.

Rashida Bradley (21:17)

Thanks.

Yes, yes. Thank you.

Kelly Dwyer (21:25)

That's really brilliant.

Yeah, thank you for sharing that.

In our pre-chat, you had made a comment about there are times where in a room, you're the only one, maybe the only woman or the only person of color or the only woman of color, right? So

Rashida Bradley (21:38)

Mm-hmm.

Yes.

Kelly Dwyer (21:45)

How do you show up there? What do you tell yourself? What's your mindset? What do want people to know about how to do that well?

Rashida Bradley (21:48)

Yes. I have to be honest. Being the only woman or the only woman or person of color or anywhere in that intersection can be very challenging, in a personal or professional. And for me, I've always tried to work through that authenticity and bringing my true like girly, bubbly personality to the forefront and build the human connection initially.

And I found that it was a struggle working in a hybrid environment. Maybe a few folks who are listening may feel the same because all of the calls are focused on work. So it's difficult to actually build the human connection. And you never kind of bridge that gap of not feeling like an outsider or different or, not in the inner circle.

I've definitely had to work through that. And I think, you know, being in certain environments longer has helped me just build my own confidence in that I can add value to that space. I can have fun and not really feel hindered by those things.

And it's also the environment that you're in, right? If it is a negative or a hostile environment, then that's different. But I think getting over your own self talk, building that confidence and self-awareness helps you make the connection. As I mentioned, my team and I have very different lifestyles, but we still have very great conversations when we have our coffee chats.

And that, I think, is really important when you may feel a little bit more like an outsider.

Kelly Dwyer (23:22)

There are a few threads there that I want to pull on. One is coffee chat. So do you have scheduled coffee chats with your team that are not about work? Okay.

Rashida Bradley (23:29)

I do. Yes, I have weekly team chats that are non-work related. it's also dictated by the style of our portfolio. So my team, work on custom strategies. And so there are normally individual contributors and subject matter experts on their category. And so it's difficult to actually find connection points for them to work together across stakeholders. When we come together for a chat it’s usually non-work related and I think that also builds a rapport. They can also share lessons learned on the stakeholders that they engage with internal to the company. We went through that quite often when we were first standing up the team. I think that's really important for leaders who manage teams that are working cross-functionally across the organization. They may feel very specialized and in a complex company like the one that I work in, that's how you and I met over a virtual coffee chat.

Kelly Dwyer (24:28)

that's right. And

these team virtual coffee chats, are they 30 minutes, an hour, 45 minutes? Okay. Yeah, yeah.

Rashida Bradley (24:33)

they're 30 minutes, I don't want them to feel like too long and stretched. I go through different

like a round robin topics of the week that are impacting their area of the business and the portfolio that they manage. But then we kind of open it up to like different topics that are going on in the news or a sporting event that's happening in their local area and kind of go from there.

Kelly Dwyer (24:57)

Okay, so it has a little structure to it. There's a little bit of what’s the latest in your area of work and then hey, who's got a topic that they wanna talk about or bring to the group and then the group has an open discussion about it, sounds like.

Rashida Bradley (25:09)

Yes, and I actually did the round robin as an icebreaker because I'm actually an introverted person. My husband would disagree, but I am. He's like, what are you talking about? I'm like, yes, I am. So, you know, I find sometimes it's hard for me to break the ice or be the first person to speak.

Kelly Dwyer (25:18)

Ha

Rashida Bradley (25:29)

And so I feel like with the round robin, you're already speaking on a topic that you're the expert in, so no one will question you. And then it kind of opens the floor to share other things along the way.

Kelly Dwyer (25:35)

Yes, yes!

Rashida Bradley (25:42)

thank you.

Kelly Dwyer (25:40)

good strategery there. I like that. ⁓ Okay, going back to one of the other threads that I wanted to pull on when you're the only one of something in the room, It sounds like you have a ⁓ real commitment to two things. One is showing up authentically. So not contorting yourself to show up in a way that you think the other people in the room are expecting you to show up that doesn't feel natural to you.

And then the second thing was a commitment to trying to find the human connection, making the human connection with the people in the room.

Rashida Bradley (26:17)

I'd like to add to your comment about authenticity. And I that's really important, especially if you think about the culture or environment that you're interacting in and kind of thinking how do you thread the needle there in terms of like understanding the culture of the organization that you're a part of maybe from a company perspective. And then how do you add value by bringing your authentic perspective to the room and having the confidence to do so. That was definitely a growth path for me as well as when I started in the healthcare industry thinking, oh, I had this confidence in financial services. I felt like I could lend that strength to a corporate finance role and then quickly humbled as I discovered the intricacy and complexity of the healthcare industry bringing that I had and being able to add that value to the room, that newly understanding the culture of the organization I had came with time.

Kelly Dwyer (27:20)

All right, Rashida, this has been a wonderful conversation with you, if you would be so kind as to share with us, if there is someone listening who is standing in their own yes and moment, their own moment of, I could go, I could focus on this or I could focus on this, but I kind of want to focus on this. And maybe there's this other thing that I also want to focus on. Or that they have to focus on, the next doable thing that you would recommend that they take?

Rashida Bradley (27:49)

about it from the mindset of constantly becoming and always charting your course. You're never at your destination, you're continuing on this journey with all the twists and turns ahead of you, who would look at your career on paper and say, well, you've checked a lot of boxes, you've completed your master's program, you're at a Fortune 10 company, what could be next?

Most recently was introduced to a group of women who are sitting on corporate boards and they're in the C-suite. And I thought, could that be next for me? And kind of re-imagining what that next chapter could look like along my career and the steps that I would need to to get there.

And so I'm excited about that, about driving forward and not knowing what to exactly expect and that my journey won't look the same as someone else's. And then I have my support system behind me and all of my crazy ambitions.

That's my word of advice. Just continue to chart your own course and know that you're never going to reach that destination if you keep reimagining what's possible.

Kelly Dwyer (29:00)

Thank you, that's great advice.

We’re never done becoming.

Rashida Bradley (29:03)

No, exactly, exactly.

Kelly Dwyer (29:06)

So Rashida, if someone wants to connect with you after this episode, where can they find you?

Rashida Bradley (29:12)

They can find me on LinkedIn. Rashida Malcom Bradley. I’d love to connect. Thank you so much. Thank you for having me.

Kelly Dwyer (29:18)

Thank you for saying yes. And we'll put the link in the show notes.