What Rules!? Podcast - Past Episodes
49. What if the Answer Was Yes?

What if you could look into the future and know for certain you’d end up a success? What risks would you then be willing to take, knowing the “hows” of everything you’re working toward?
Join Alisa, Rosa, and Dr. Merary as they look closer at the idea of risk-taking and ponder the question “what if the answer was yes?”
Alisa Manjarrez: (00:00)
… so, I know today is all about risk-taking, and the risk I’m taking right now with my skin care, and I promise to our What Rules!? listeners, this is not an advertisement, but I use this product, it’s called C.E.O. by Sunday Riley. It’s like a vitamin C serum. Have you guys heard of it?
Rosa Santos: (00:18)
No.
Dr. Merary Simeon: (00:19)
No.
Alisa Manjarrez: (00:19)
Okay. I see the blank stares. I should have brought it with me for our YouTube people. It’s this serum that just brightens up your face and you can’t tell I’m wearing makeup and all that. But I ran out last month and I can tell the difference. And so, every morning this week, I’ve just been looking at how dull my face is without my vitamin C serum. But I refuse to buy it myself, because it’s like 100 bucks a bottle. And so, I’m waiting for gift cards to come for my birthday for Sephora, because that’s how I buy it every year. So, I’m out of it.
Rosa Santos: (00:54)
So, you’re not… No, listen, listen, listen, listen, you’re not taking risks. You’re gambling.
Dr. Merary Simeon: (01:02)
There you go.
Alisa Manjarrez: (01:05)
You know what I hate about Rosa? Look, let’s start there. When I say, “Oh, Rosa, your makeup looks so good.” And you’re like, “No, I’m not wearing any.” You don’t need my C.E.O. Sunday Riley Serum.
Rosa Santos: (01:22)
I just need sunshine. Let’s put it that way. I just need sunshine.
Alisa Manjarrez: (01:25)
What’s your skincare secret?
Rosa Santos: (01:27)
Actually, you’re not going to believe this. I don’t know whether to tell you, but it’s a vitamin C serum that I put on every morning.
Alisa Manjarrez: (01:35)
No way.
Dr. Merary Simeon: (01:37)
And I’ve been using Avon, probably, for the longest and I tried other expensive things, and I mean, my face is spotless.
Alisa Manjarrez: (01:46)
Okay. All right.
Dr. Merary Simeon: (01:47)
It’s a lot of water. I do drink a lot of water, for sure. But honestly, moisturizer, Avon, and it’s cheap.
Alisa Manjarrez: (01:53)
You heard it here What Rules!? listeners. Obviously, don’t follow my advice.
Alisa Manjarrez: (02:04)
So, this is the What Rules!? Podcast. We are here helping multicultural women shatter glass ceilings on their way to the C-suite by breaking the rules and outsmarting the game to advance their careers.
Alisa Manjarrez: (02:20)
Today with me, I have Rosa Santos, a leadership expert and HR executive; Dr. Merary Simeon, HR executive, motivational speaker. I’m Alisa Manjarrez, vision producer and executive coach.
Alisa Manjarrez: (02:37)
This month is my one year anniversary of going out on my own, taking a big risk, and starting my company, The Happy Cactus.
Rosa Santos: (02:47)
Woo-hoo!
Dr. Merary Simeon: (02:48)
Yay.
Rosa Santos: (02:48)
Awesome.
Alisa Manjarrez: (02:48)
Thank you.
Dr. Merary Simeon: (02:49)
Yes. Congrats.
Alisa Manjarrez: (02:50)
I started before I was ready, and somehow I’m able to pay the bills. I honestly have no idea, but I have been able to pay the bills for the last year, and I call that a big win, and a risk worth taking.
Rosa Santos: (03:03)
Absolutely.
Dr. Merary Simeon: (03:03)
That’s because you’re amazing.
Alisa Manjarrez: (03:06)
So, I want to share something with you guys. I had a session with my coach. We were kind of reflecting on the last year, and I was like, “I can’t believe I decided it, create a title for myself.” But I was feeling kind of foggy like, “Where am I going with this?” Now that I’m here for a year, I’ve been doing part coaching, part vision production. And he said, “What if we use your vision production process on yourself?”
Alisa Manjarrez: (03:30)
And I have this five-step process. I do an untangling session where we say your brain is like spaghetti and we untangle one noodle at a time. Then we refine the vision and expand it, and do all these things, and finally create a strategy and get it done.
Alisa Manjarrez: (03:46)
Part of that untangling session, we did that, and it’s asking a lot of questions. And after I got done asking all my questions, it’s just like a big brain dump.
Alisa Manjarrez: (03:56)
I want us to think about this as we think about risk-taking today. He said, “What if the answer was yes? And what if all the hows were known to the level of perfection you desire? What, then, would all of this look like? And what is the possibility you’re creating?”
Alisa Manjarrez: (04:14)
When I think about risk-taking, I think, “What if the answer was yes? What if I knew how it was going to be done? What do I actually want to create?”
Dr. Merary Simeon: (04:23)
That’s deep. I’ll let Rosa go because she knows, she compartmentalizes all these things.
Rosa Santos: (04:29)
What do I think in relation to what we’re talking about? I think that’s a really good way, in fact, or a framework, especially for women when you think about taking risks and what it implies or what it brings upon you, I think that you can follow, right? Because then you can decide whether it is worth going that way or a different way. Again, even just to, for those who are not necessarily there, think like, “I’m not that type” or “I’m very conservative and risk-taking is not for me, I want to take things in a measured way,” I think this helps to maybe going the extra mile, to really jump onto something that you’re not very comfortable with by breaking it down. So, I think you did an awesome job in doing it in a way that can help a lot of people that may not think that they can take risks in order to advance or create value for yourselves.
Rosa Santos: (05:29)
Because one of the things that I would like us to explore today is a little bit of this notion of how risk-taking creates value for yourself. Even though you may think that you’re not a risk-taker or you were not brought up to believe that being a risk-taker is part of your identity and how you go about life, this is going to help you really take those first steps.
Dr. Merary Simeon: (05:53)
Yeah. I like the framework and I love that you called that a framework, Rosa, because it does open you up to the possibility. Face it, we make decisions every day, some small, some have a great impact in our life, but I also do believe that there’s a balance between the risk-taking and playing it safe. Because when we’re making big decisions, we need to accurately perceive what those obstacles are going to be. But I love Alisa’s framework because the answer is yes, right? So, it also leaves you open to those opportunities that you may have not thought of because you automatically go into playing in the safe space.
Rosa Santos: (06:30)
Exactly.
Alisa Manjarrez: (06:31)
Yeah, it’s like our brain wants to make sense of it and we’re like, “Okay, I can think about the impossible, but how?” Like, “How’s it going to look? How’s it going to work?”
Alisa Manjarrez: (06:40)
When you start getting into that how, that’s when that doubt creeps in. If you let it take over, it takes over and now you don’t even want to risk at all, because you’re like, “I don’t know how this is going to work. I’m going to stop.”
Alisa Manjarrez: (06:55)
I read this study called Risk, Resilience, and Reward by FMCG, I believe. No, not FMCG. That’s… I’ve been thinking industry. It was by KPMG. Let me get my acronyms right.
Rosa Santos: (07:14)
One of those consulting firms.
Alisa Manjarrez: (07:19)
KMPG, they interviewed 2,000 women and they said, “Less than half, 43%, were open to taking big risks that are associated with career advancement. But a larger number, 69%, were open to taking small risk to further their careers.”
Alisa Manjarrez: (07:38)
So, it’s interesting, Merary, that you brought up the small risk and the big risks. I think that small just naturally is easier.
Dr. Merary Simeon: (07:47)
I think it also depends your emotional stage that you’re in, right? I know for me, if I’m making a decision and I’m under extreme stress, it’s going to cloud my judgment whether I like it or not. I’ve also found that stress can lead me back to those habitual behaviors, right? “Oh, no. I’m not going to take the risk.” So, it goes two ways, either you go and make risk that cloud your judgment and could put bigger things at risk, or you go back to the deep stress where you’re almost paralyzed and you’re like, “I’m not going to take any risk.”
Dr. Merary Simeon: (08:18)
So, to me, the emotional stage that you’re in when making those decisions is critical. It’s critical to pause, to examine, and really understand the associated risk with the actions that I’m taking.
Alisa Manjarrez: (08:32)
How do you know when it’s time to slow down? What are the little indicators for you when you’re in that bubble?
Dr. Merary Simeon: (08:38)
That’s the key that I don’t know. Listen, anytime that you make a big decision, it’s stressful. You just have to balance it to make sure that you’re understanding what the consequences can be. And if the answer is yes, these are all the great things. And if the answer is no, these are all the watch outs. But then where do we meet in the middle so that I can really weigh the options objectively?
Rosa Santos: (09:01)
For me, when I get caught up and I think what we need, to your point, Merary, self-examine where we’re at, it’s because naturally, because of gender, cultural norms, how we’ve been brought up, this notion of risk-loving is not necessarily there, right? It’s always being more about playing it safe and then taking risk to create this value for yourself.
Rosa Santos: (09:27)
So, inherently, even these frameworks and the way that we think about taking risks, we… Even in the way that you both are talking about it, is a lot about, “I need to feel comfortable about it.” But the way that we rationalize or compartmentalize, because that’s what I will do, right? The way that I move from one decision to the next, I think it has a lot with the fact that we are women and that we need to feel absolutely 100% every single step of the way, has to tick all of those boxes for me to be able to do that. Whereas, a lot of this research says that even from the way that we raise our kids, men don’t have those issues. They might tick two or three boxes out of 10, and they go, “Okay, that’s fine with me. I’ll go ahead and do it. And then-“
Alisa Manjarrez: (10:11)
“That’s enough.”
Rosa Santos: (10:12)
Right? “And that’s enough.”
Rosa Santos: (10:13)
I was reading a really interesting one by the University of Houston about paternal patterns in society and looking at two different ethnic Chinese groups and how they raise their kids. One was very male dominated. The other one was more matriarchal. And how in the matriarchal society, the girls were… Even in the playground and how they played, and took more leadership roles, and how then in comparison in those two societies, to, again, have more overall value for themselves, it was much higher in the matriarchal than the patriarchal society, had to do with the way that those kids were being raised to take those risks.
Rosa Santos: (10:58)
For me, when I’m looking at this and then looking at then how we break down that mental process, what needs to happen for us to even accelerate and breaking, and maybe disrupting that thinking a little bit so it doesn’t take us that long to, maybe, take the first step… Because my fear now, having done all this and reading, and seeing around is, “Am I waiting too long?” Right?
Dr. Merary Simeon: (11:26)
Mm-hmm (affirmative).
Alisa Manjarrez: (11:27)
Yeah.
Rosa Santos: (11:28)
And by the time I say, “Yeah, I want that,” somebody else came and did it, right? Then it’s like, “Oh, okay. It happened.”
Rosa Santos: (11:35)
I was listening to the radio the other day, around how women and men are taught differently on how to manage their portfolio in the stock market, and how women tend to have more midsize cap stocks and bonds versus men who go for all large cap and really taking big risks. It’s interesting when you look at it that way, how many aspects of your life actually impacts, right?
Dr. Merary Simeon: (12:04)
Yes.
Alisa Manjarrez: (12:04)
But I’ve actually heard when it comes to investing specifically, women are better at financial investments because they naturally take a more long-term view whereas the men are looking for these short winds. It’s almost like the shadow side of looking at the big picture is the waiting. If you’re looking too long at the big picture and if you really see all… It’s funny, I’m interrupting myself because when you were talking, I was-
Rosa Santos: (12:36)
I’m going to interrupt you in a minute. Go, go.
Dr. Merary Simeon: (12:39)
Interrupt yourself. Go ahead.
Alisa Manjarrez: (12:41)
I was thinking about… You know, they say… I mean, this is so generalized, but I was thinking about how young girls are more prone to do better in school because they’re doing all the things. They’re like, “Yes, I’m following all the rules. I’m checking all the boxes. I’m getting my grades. I’m memorizing my stuff.” But when you look at the GPA average for the typical male CEO, they’re C students. The people leading our country are C students. They got there just enough.
Rosa Santos: (13:09)
But that was going to be my interruption, Alisa, because I think even in the way that you described it, I am actually challenging whether that is a good thing or a bad thing, right? Because then when you go for the short gains… I’m not saying that everybody should change their portfolios right now, this is not that conversation at all.
Rosa Santos: (13:26)
But in the way that we… I mean, I guess those tags that are put in general about men and women, and how we go about life, in this case, taking risks or making decisions, is just such a static and a stagnant way of looking at the dynamism of how we need to think about ourselves and what’s important for us. What you just said, Alisa, in regards to the longer term view and whatnot, if you take that and you apply it to a work environment-
Alisa Manjarrez: (13:57)
You’re going to lose.
Rosa Santos: (13:58)
… you’re going to lose. You lost the game.
Dr. Merary Simeon: (14:00)
Yes.
Rosa Santos: (14:01)
You lost it. You think that you’re doing all the right things, what everybody’s been telling you. And especially, let’s put this into perspective of the multicultural and women of color or what that means for us here, you cannot be looking at the longer game because you may not be there.
Rosa Santos: (14:18)
I think in this case, I’m totally generalizing, the shorter gains augment and catapult, right? And being able to have a little bit more, and I’m doing air quote, “money,” whatever money is, to then put it towards that longer game, right? So it’s a little bit of disrupting how we’re thinking about this idea of taking risks.
Dr. Merary Simeon: (14:43)
Yeah, no, I agree. I mean, I love taking risks, but I go back to taking calculated risks.
Alisa Manjarrez: (14:47)
But isn’t that what we’re trying not to do? Isn’t that where we go wrong.
Dr. Merary Simeon: (14:52)
Yeah. Just because the men do it, it’s cool for them, but at the end of the day, I got to do what works for me. And I do agree with you 100%, in the work environment, if you really look at the long term, you are absolutely going to lose. You’re going to see a lot of people pass you by and you’re going to have to take those risks and apply for that role and use, now I say Alisa’s framework of “What if the answer is yes? And what if it’s positive at the end?”
Dr. Merary Simeon: (15:17)
But I believe a lot of the risks that I’ve taken, I’ve calculated. I look at what’s the worst thing that can happen and what’s the best thing that can happen. And am I my willing and can I deal, and can my family deal with those risks?
Dr. Merary Simeon: (15:29)
Because at the end of the day, once you have a family… Well, for me, it’s no longer just about me. It’s about my team. And I always talk about my team is how do I make my team better? And I need to make sure that those calculated risks that I’m taking protect my team at all costs, because if I take myself out of the game, we’re going to lose the game.
Rosa Santos: (15:48)
Yeah. Let me read to you guys what I read in one of the McKinsey’s studies, and this is a quote from Kathleen Murphy, who’s a president of Personal Investment at Fidelity.
Rosa Santos: (15:59)
And she said, “In general, men seem to have more confidence in their ability to get to the next level, to take the next risk. Women, too often, are more conservative in their approach. If you are conservative about your career over and over again, over the course of 20 or 30 years, the cumulative effect is that you aren’t going to advance nearly as much as the person who takes risks.”
Alisa Manjarrez: (16:27)
Yeah. I read that the older you are, the less risk-averse you are in your career, because you’ve seen it happen. You see all the mistakes people make along the way. And so, it’s like fear sets in, because you’re like, “I’m not going to do that,” where the young, naive people are like, “I’ll take a risk.” But they can progress faster. So, there’s got to be some kind of balance.
Alisa Manjarrez: (16:48)
If I were to create a toolkit on risk-taking, definitely, Merary, what you’re saying, list your pros and cons.
Dr. Merary Simeon: (16:53)
That’s right. Yeah, and by all means, I’m not saying, “Hey, all the cons may be horrible,” but it’s how do you move one step forward each time, towards making that dream or that reality, or whatever it is come true. And that’s why I talk about calculated risk. And it may be that you have a plan B, “Hey, you know what? I’m going for this. And I’m…”
Dr. Merary Simeon: (17:13)
And like I said, I don’t care, honestly, me personally, if men take the risk. I do what’s best for me at the end of the day. Am I going to stay a little bit behind? Hey, if it means to do what’s right for me and I could live better, fine. But I also do agree that I have to take more risk, right? But to me, it’s just a little bit more balance, then maybe might be for somebody else.
Alisa Manjarrez: (17:36)
What would be the edgier version for you, personally, for a risk-taking?
Dr. Merary Simeon: (17:42)
The edgier version would probably be somebody that, “It’s all about me. And if it works, it works. And if my team goes down, it goes down.” But that’s not who I am.
Alisa Manjarrez: (17:51)
I wonder if that mentality is what gets us all trapped, because I feel like women want to take care of everybody and your family is number one, right?
Dr. Merary Simeon: (18:04)
Yes.
Alisa Manjarrez: (18:04)
Your family is number one, your friends, all that is number one. And men don’t think like that.
Rosa Santos: (18:11)
Exactly. Right?
Alisa Manjarrez: (18:12)
Yes.
Rosa Santos: (18:12)
I think that’s spot on. And I think it’s getting out of a sense or feeling of guilt, right? Because sometimes we do have that and that comes into play. Like to your point, you can get trapped up on the fact that, “Okay, I won’t do this because if I do it, there’s a possibility that the impact… There’s a 50-50 percent that the impact will be negative. And I don’t want to do anything that may impact, not me personally, but others.”
Alisa Manjarrez: (18:41)
Does it have to be where if I’m taking a bigger risk, I’m looking out for myself, for number one? Is that the story? Is that the right story, because if I’m taking a risk, I have my family, whatever is at stake for me, is me taking a little bit more of a risk having a “I’m number one” mentality or is that just what I believe the story is?
Dr. Merary Simeon: (19:07)
I think you’re right. I think you could be the story. I go back to my husband leaving what he wanted to do to support my career. That was a huge risk but we took it. See, my mentality is my team and I’ve always been like that. So, we took it together. We knew the risk that came with that and we were willing to deal with those risks and those pros and cons that come with it. In anything that I do, we make the decision together. Now, I feel, also, that I also have the responsibility to, as part of a team, be able to bring forward what’s right. That ultimately is going to be best for all of us.
Dr. Merary Simeon: (19:49)
But I do agree with you. I think sometimes it could be, “Is it all about me?” And maybe that’s not the right story for somebody else. It just depends, right? Where you at emotionally, where you at from in a stress perspective, and what are some of the things that you’re facing outside of that one decision. Because remember, you’re talking about risk taking for one thing, but it’s not just one thing that impacts us. There is tons of things around us that impact our life. And until you’re looking at that full picture, I don’t feel I can make a decision based on one action. I have to look at the full picture.
Dr. Merary Simeon: (20:26)
Rosa said it earlier, but I know there’s a lot of research that talks about every time a woman makes money, she invests back in her community, right? She’s always thinking of others and bringing others with her. And at the end of the day, it’s how do we advance that and take that risk to help us be more financially stable so that we can continue to bring more with us. So, there has to be a balance, and what works for one may not work for the other. But I absolutely agree that we do need to do something to accelerate some of those risks.
Rosa Santos: (20:58)
Yeah, and I think there’s something… Especially when it comes to career progression, right? And when it comes to career progression for women of color and multicultural women, I think we should be providing on the one hand more overall sponsorship, right? Because it doesn’t matter that you go in and you said, “I’ll go take risks.” We know how that works, right? In some businesses and organizations, et cetera, sometimes it’s not all about taking that risk on your own. You have to have someone who’s going to be there alongside you to say, “You know, if this fails, I’m going to be there to help you up and to bring you up.” Right?
Rosa Santos: (21:43)
And I think the one thing that we can do to change that trend and have more of these women, especially, to put themselves forward, to apply for that job, to raise their hands and whatnot, is creating more room and more space for a sponsorship for those women and overall support to let them know, to have someone there who’s then going to say, “Okay, you didn’t get it this time, but I’m here to help you on the journey and the next time, but don’t give up.” Because at the other side, you might encourage this idea of risk-loving, right? But then if the risk doesn’t pay out, then you can have the opposite effects, especially as it pertains to growing and moving forwards, and growing in your career, and professionally, you really need to have that network of support that you can go back to and say, “Hey, this didn’t work out, but I am not going to give up.” And you’re going to have what I call the cheerleading squad, who’s going to say, “It’s fine. You did it. Just the fact that you did it is already an achievement.”
Alisa Manjarrez: (22:52)
If we were to put one of our guiding principles up, we always say, “Don’t do it alone.” But in this case, it’s, “Don’t risk alone.” Because when you can build that parachute, I would much rather skydive with a parachute than without.
Alisa Manjarrez: (23:08)
And if we’re talking about how women want to be prepared, what might hold me back is, “Oh, everything has to be in place” or “I have to know.” But maybe my way of preparation isn’t that. Maybe I can move faster if my way of preparation is looking at the people around me and saying, “Who’s going to catch me if I fall on an emotional level, financial level, all these things?”
Alisa Manjarrez: (23:30)
I know a woman who just quit her job and moved in with her sister, and her sister’s like, “I got you.” That’s fine. It’s not forever. But she had a place to live and that was important.
Dr. Merary Simeon: (23:42)
I love that. Who’s going to catch you? Right? Who’s going to be there to support you? That’s part of that risk-taking in assessment. It’s like, “Hey, this is the worst thing that can happen but hey, here’s how I can address this.” Right? “I do have a place to live or I have somebody that’s going to listen to me and support me, mentally.”
Rosa Santos: (24:03)
Yeah. All right. Are we set?
Alisa Manjarrez: (24:06)
We got to end it.
Rosa Santos: (24:07)
Oh, we have to end it?
Alisa Manjarrez: (24:11)
Rosa is like, “Mic drop. Done.”
Alisa Manjarrez: (24:16)
What do we want our listeners to walk away with? Merary said, “Look at all the factors at play. Look at the big picture.” We said, “Have a support system. Be open to possibilities. Don’t be afraid of moving faster than might feel comfortable.”
Rosa Santos: (24:32)
I would say, what else can you do for others? Who are you encouraging along the way?
Dr. Merary Simeon: (24:37)
Who are you enabling?
Rosa Santos: (24:38)
Yeah, because risk-taking can be a very lonely journey and process, right? It’s like, “Oh, I don’t want to take any… I don’t want to tell anybody that it’s taking me a long time to apply for that job.” Or have that courageous conversation around the fact that you need to be paid more or what is next for you, right? And you tend to do this all on your own. Look around and see who might be going through that mental process or internal process and just offer your help so they can, actually, maybe even rehearse on how to go out into that conversation.
Dr. Merary Simeon: (25:11)
Leverage your network to see how you can help somebody be successful and take that risk. I think a lot of the times, to your point, we think we have to do it alone or the people around us. But if Alisa was taking a risk and I knew about it, I will engage my network to see how we can help her be successful.
Alisa Manjarrez: (25:28)
That’s real life. That has really happened with the both of you. You have helped me in my entrepreneurial journey.
Dr. Merary Simeon: (25:37)
But those are the things we got to think about. And I love that you brought that up, thank you, Rosa, because we do need to think what are we doing to help others be successful?
Rosa Santos: (25:47)
Absolutely.
Dr. Merary Simeon: (25:47)
We all need to play a role.
Rosa Santos: (25:49)
Exactly. And it’s about validating, right? It’s about validating that what you’re about to do is the right thing to do in that moment in time. And it’s okay to take the risk. Because as my mother used to say to me when I was a little kid, “You will always have the ‘no.’ If you don’t try, you will not know.” The answer “no,” it’s already there. So, the only upside is a game. Just go for it. Go for it.
Alisa Manjarrez: (26:25)
Want to know how breaking the rules can help you level up your career game? Search What Rules!? Podcast on any social media platform and join our members-only group on LinkedIn, where we discuss rule breaking strategies for multicultural women.
Alisa Manjarrez: (26:39)
What Rules!? is a production of Color Forward. The show is produced by me, Alisa Manjarrez, with editing and fabulous sound design by Mathr de Leon. Visit colorforward.com for more stories, events, and of course, all the episodes of What Rules!?.
Alisa Manjarrez: (26:57)
Now, that’s an ending.
Dr. Merary Simeon: (26:59)
That’s it. I love it.
Alisa Manjarrez: (27:01)
All right. There you have it. There you have it.
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