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A Conversation on Confidence and Calculated Risks

with Financial Inspirer Sara Samuels

Hey goal achievers, Kristin here. Recently, I had a guest on the Elite Achievement Podcast that I first heard speak at a women’s summit for financial advisors. I attended a breakout session a few years ago and listened as Sara Samuels talked about the power of marketing and communication. I remember being blown away by her confidence, poise, and ability to command the attention of a room, and I am so grateful to have the opportunity to learn from her in this episode

Sara is a former practicing attorney turned Wealth Management Advisor who specializes in working with emerging professionals and business owners. Her mission is to reduce economic vulnerability and build enough wealth for her clients to live their very best lives now and in the future through financial inspiration. I welcome Sara and know that we are about to explore taking risks, the importance of advocating for yourself, and how to succeed in a male-dominated career. 

I begin by asking Sara what prompted her to switch careers from being an attorney to becoming a Wealth Management Advisor.

From Attorney to Wealth Management Advisor

“The story starts a little bit before that,” Sara begins. “I’ve come from a family of business owners. My mom ran her own business as a photographer and massage therapist, and my family had a jewelry business. Having seen both the ups and downs of being a child and grandchild of business owners, I kind of wanted to go the other way. So, I went into what I thought would be a ‘stable profession.’ First I was pre-med, and then I ended up becoming an attorney. Both of those were considered ‘stable careers,’ if you will. And that’s actually what made me head to Chicago in the first place. I moved sight unseen for law school. Those who work with attorneys, or have attorneys in their family, or maybe were one themselves, understand that you go in intending to be an advocate. I was a defense litigator, so it wasn’t criminal. But oftentimes, it was adversarial. The farther I went into it, the more I realized that I truly wanted to be an advocate for myself and others. So, once I started working for someone, I was like, ooh, I don’t enjoy that as much. Let me see what this other thing looks like. I also recognized that not everybody who is an employer is actually a good business owner that treats their employees as team members. During this time, for about four years, I was a client at Northwestern Mutual. And my advisor said to me, have you ever thought about doing what I do? At the time, I said, I don’t actually know what you do. But it was a great opportunity for me to at least consider something because advocacy comes in different forms. And after understanding and appreciating what it means, I understood that it’s so much more than relationship building, intention driving, and helping people change and shift their relationship and paradigm around money. It often is about confidence. And that changed the way I thought about things. I took a massive leap of faith and started my practice in July 2008. Great time to start in financial planning, by the way.”

I can imagine that 2008 was a very scary time to start in financial planning and ask Sara how she navigated the uncertain waters during that season. 

She explains that part of it was having a great support system, both in her personal and professional life. “One of the unique things about the financial services world, especially where I’ve been, growing and living and surviving and thriving, is that it’s a community that is more about giving a hand up than giving a handout,” says Sara. “The competitive nature isn’t necessarily about trying to do better than you by taking your clients. It’s more about asking how we can all do better by helping each other be advocates for each other. That was a great foundation. Secondly, I have a lot of grit and a lot of perseverance. I want to be successful in anything I do, but especially where I feel that it’s a great fit. And I think when I started, I wasn’t sure. But as I really began sitting down with people and saw how little financial planning was being done, especially with women, minorities, people of color, and people who maybe have been institutionally but not financially marginalized, I realized how important it is for people like myself to be a mirror, not a window, as our good friend Nicole Stokes would say.”

Sara mentioned earlier that money is often about confidence, and I’m curious what she means by that.

Money: It’s All About Confidence

“Money is integrated into every single thing that we do, and how much we think about ourselves and about our ability to be able to succeed,” Sara begins. “And without a solid foundation, there can be significant anxiety. If you don’t feel you have a place at the table financially, you may not feel like you have a place at the table professionally. I also think that because this isn’t something taught in school, it can feel very foreign, especially with the volatility in the market and volatility in life. Confidence in our financial world means having attractive options, no matter what happens, being able to say that we can take a leap of faith, like myself, because we have enough of a financial runway to do so. In addition, I’ve heard some people talk about how women think that they need to know 99.97% about something before moving forward. Guys meanwhile are like, I know 30% so I’m good. I wanted to shift that – I spent a lot of time with my clients, talking about the fact that behind closed doors, a lot of us don’t actually know much about this stuff. And so, it’s a no-judgment zone in my office. You make no apologies for what you didn’t know coming into this. It’s also a no excuses space. If we do have the desire to make a difference, we have to take personal responsibility. So that confidence comes from knowledge, from ownership, from education, and from integrating it, and removing that emotion and shame that often comes from talking or thinking or being boastful around money. It is not about being boastful. It’s really that determination between confidence and boasting.”

There are so many beliefs that come up for people when they start talking about money, and we all have different relationships with money. Sometimes there isn’t enough conversation around money, limiting our knowledge and confidence when it comes to understanding finances and growing our finances. Sara mentioned having some financial savings to take a leap of faith, so I want to explore taking a calculated risk. I ask her to elaborate on first, what is a calculated risk and second, her thoughts around taking one.

Calculated Risks: Acting Before You Are Fully Ready

“You mentioned this relationship with money,” says Sara. “That relationship with money never starts with us. It usually starts generations before us, so recognizing that maybe your great feeling about money comes because your grandparents had a great relationship with money and now you’ve had that positive ability. Or, if they always thought that the other shoe would drop, then that will inform your reality, so there is a shift that does have to come. Just like my mom and grandma both tend to be overweight. So, I have to be aware that I am inclined to do the same. I think understanding inclinations and your feelings around money has a lot of impact. To me, the definition of calculated risk is being informed about the potential obstacles and the opportunities in a situation and eventually moving forward. It’s a leap of faith at some point because there is this whole concept of ‘paralysis by analysis.’ And at some point you have to say, is the risk worth it? When I think about regret, most of my regrets have not come from the actions I’ve taken. They’ve come from inaction or things that I didn’t say or wish I had done, not the things that I did. I think that’s because I had the opportunity for reflection and growth from the things I did, not the things I didn’t. So, to me, calculated risk is once you’ve waited, you just got to move forward. That’s what I did moving to Chicago for law school. Hey, no one’s going to blame you for moving for law school, right?”

“But how about leaving a six-figure salary for 100% commission? Plan B, I could have gone back and been a miserable attorney. I already knew how to do that one really well. Think about jumping out of an airplane. You know, I did the research and guess what? It’s much easier to die in a car accident than jumping out of an airplane. And I wanted to feel that exhilarating feeling. There is this really unique kind of juxtaposition of risk. ‘Risks with research’ is probably a good way to think about calculated risk.”

I agree with Sara. Regret for me comes from all the things I wish I would have done or I wish I would have done sooner. And it’s often because I’m overthinking the situation that I didn’t do something. It’s all the what-ifs. I do a really good job of thinking about the obstacles, and all the things that can go wrong, so I don’t have an opportunity to think more about what could actually go right. It’s one of the things that I work on with my coaching clients when they’re in a position to take a risk or they’re feeling fear. I coach them to explore both the best things that could happen and the worst things that could happen. When you’re taking a look at both options, then you can make an informed decision. Sara has done things that have taken a lot of action and calculated risk, so I ask her to share how others can learn to act before they are ready. 

“I would say for me, the biggest hurdles have been when I thought I was ready,” Sara says. “And maybe I wasn’t, but I still move forward. I think there’s a feeling that comes from that, right? At some point, you’re like, I think I’m ready, but you’re never going to know fully. So, you just have to commit. That could be in your personal life, that could be in your professional life, but sometimes we just have to move on. Sometimes in my personal life, I held on to relationships longer. I held on to friendships longer than maybe I should. In my professional life, I am pretty good about moving forward quickly. And so sometimes with confidence, you can have different levels in different areas. You can use that to lean on the areas you’re not as confident about. I’ve had points where I’ve felt really great about where I was personally – in my relationship, my health, everything was firing on all cylinders. But professionally, I didn’t feel it. So, in recognizing that and being able to parse out, well, is this situational? Or is this actually emotional? Or is this truly how I’m feeling about things? Lend one area of confidence that you may have to serve another area. When I look back at the risks I’ve taken, I was never 100% ready. But I was enough. I was maybe 60/40. And again, if you know you have a plan B through Z, you’re there.”

I appreciate how Sara describes confidence because I often think of confidence as one thing. Like if you’re confident, you’re confident in all the areas – personally, professionally, financial health, fitness, etc. But Sara has made a great point about being confident in one area of our lives and growing our confidence in another area of our lives. I’ve always been very impressed with her confidence and ask her to share what she has done to grow it and what others can do to do the same.

Growing Confidence Starts Internally

Well,” Sara begins. “I’ll share that it didn’t start immediately. I’m from Southern California. And I know this is a blog, so readers can’t see me. But imagine a 16-year-old in the mid-90s in Southern California – the height of ‘Barbie doll-looking’ girls, right? I’m 16, 200 pounds-ish, brunette, and smart. And my family moved, like 30 times, so I was always the new kid. I was teased pretty relentlessly for good portions of my life. Experiencing that, I started understanding that often, people tease because of their own insecurities. I was really blessed that I had a family that helped me think about confidence and my attributes differently from just attaching it to my physicality. As women, we attach so much of our confidence to our physicality. I’m not saying that I still don’t deal with that. We all have our own issues and body dysmorphia, and other things. But I started placing so much more of that on my capacity and capability, and skill sets as a person, and really started using that to be the trailblazing part of myself. Then hey, guess what? Later on, I lost 70 pounds. And certainly, that has helped from some of the outside, but it truly starts within. I’ve been blessed that I have many people around me and have always sought out people around me who add value and believe in me. Sometimes you need people to believe in you before you believe in yourself. About five years ago, I saw a great article in Vanity Fair about the creator of Ariel investments. She talked about the greatest attribute she had, other people who saw things in her before she saw herself. But then she learned to see them in herself as well. I’ve had other people see things about myself, but at some point, you have to recognize them in yourself and move forward as well. So that’s been a huge part of my confidence.”

“The other part is, the older I’ve gotten, the more I realize that it really doesn’t matter,” Sara continues. “Nobody else is looking at you because they’re also looking at themselves. When I stopped worrying about what other people thought of me and started worrying more about how I thought of myself, it was a really good opportunity. Over the last, say, five years, being now almost 44, I’ve really found more internally emanating confidence, and other people have been able to experience it too because our energy speaks well before we do.” 

I agree with Sara that confidence starts within yourself. If we’re constantly looking externally for confidence, I think we will be disappointed a lot. And our confidence is going to ebb and flow based on other people’s responses or perceptions. Learning to stop worrying about what others think and start worrying about what we think is a powerful shift to help grow confidence. 

“There’s this great meme,” adds Sara. “It’s the one that says ‘happiness’ on one guy’s stomach, and the other guy is like, oh my gosh, where did you find that? And the guy that has it says, I found it inside. I just love that concept, especially in this last year with the ‘zombie apocalypse’ of 2020. It required and forced us to have a lot more introspection about where we find happiness and where we look towards others. Confidence is more about feeling self-worth and feeling worthy and deserving of what we’re given. In what we have and what we strive for, and again, going back to that concept of value and worth, confidence isn’t necessarily treated as a positive attribute in certain sectors of the population. And if you can own that, and say, this isn’t a bad thing that I’m confident, or that I feel good about myself and understand that I have value – it changes the conversation.”

I ask Sara how she thinks confidence has helped her succeed and thrive in a male-dominated career.

Dominating in a Male-Dominated Career

“This is probably my second male-dominated career,” says Sara. “Actually, I was going to become a sports agent. So, I really, truly like to stick in that game I guess, a little bit. For me, confidence has allowed me to always feel like I have a seat at the table. Maybe because I did come from a male-dominated profession, growing up in sports – which tends to be more of that ‘do you,’ ‘be your best self’ heavy work ethic – I was really lucky. I was raised in a fairly matrilineal family, where the women typically worked, held high degrees, and ran our family business. It was already a vision of what was possible. My grandpa was more of a supportive person in our family household versus being the natural breadwinner. So, I know it’s possible. In fact, I knew it was even encouraged in my family to do whatever you possibly could because the road was open for what I could accomplish. I didn’t know that there were impossibilities other than what was between my own two ears. When moving into a male-dominated profession, I never even really thought about it. I thought it’s such a huge opportunity. I was not the Chad and Brad’s of Northwestern Mutual, you know, or any other financial firm for that matter. There are a million ‘dude’ advisors. We can differentiate ourselves but not be different. Differentiating is making sure that you are seen and heard in a unique way. And that is, to me, confidence in a male-dominated area. I want to lean into the fact that there are only a few of us in the room. And I want to make a bigger impact because I want to be seen and heard. So that’s been huge for me and been exciting. Now I see other women and other minorities who are using that as a real way to say, hey, I may not look like your typical advisor but isn’t that exciting and refreshing? The other part about it is, look, every guy is a son of a woman, and often has a wife or a partner, or daughters, and so to be able to show them what is possible for their wives, children, parents, who would have hoped that more of us would do this is huge. Lastly, money often leaves with the widow from our organizations. And so, for me, being able to say, to my older clients, or my female clients, or to have those relationships with their male husbands and say, I’m with you for a lifetime, and hopefully, generationally, this is also about the dollars and bills. I want to hold all of those because of the relationship. This is a return on relationship business. That confidence has allowed me to be a big fish in a small pond, in my opinion, versus one of many fish. I feel like I’m more of the beta fish amongst goldfish in a great way.”

Sara talked about advocating for others and advocating for herself, so I am curious what she would tell women who want to learn to better advocate for themselves.

“I coach a lot of my female clients,” Sara says. “I say you asked for it. I’ll help you grow and protect it, right? We can get over this concept that we don’t deserve it or that we shouldn’t ask for it. Yes, there is, of course, an institutional component of why people of color, women, first-generation immigrants make less, so let’s not discount that. They’re real. However, it is incumbent upon us to also always be our biggest cheerleaders and not feel bad about it. Guys make more half the time because they ask for more because they feel they deserve it. We have had an institutional attitude that says, this is not for us, or we have to sit in the back and take what we get and be so happy for that. And I say, absolutely not. The next generation is about us truly being the best version of our own empowerment through our finances, profession, and sense of self. And that comes from really, truly being our number one. I’m the number one, not because I think that I’m a super rock star, but because I’ve had to, and it’s been valuable. People buy into people who feel pretty awesome about themselves, so eventually, it begets itself. There’s a fine line between boastful and confident. But for most people, it can really take a lot to get there. That also comes through authenticity and being genuine. If you’re authentic and genuine, show that you have a beautiful heart. Show that it’s coming from a place of care and helping and not self-serving. It’s coming from a mission and service standpoint, which is very, very different.”

Mission and service are such important topics, and I ask Sara how she would describe financial inspiration. 

Financial Inspiration: Money as an Opportunity vs. an Obstacle

“I just started banding around,” starts Sara. “Like, asking where do I get inspiration from and what inspires me to move? And again, when I think about traditional financial planning or just finance in general, a lot of it is very fear-based. So, we tell people, if you don’t do this, this is going to happen to you versus if you do this, this is what’s possible. And I really wanted to shift that. I heard Monica Sinha talk about this, that she really wants her clients to feel inspired to live their best lives. So, I leaned into that and was like, me too. I want my clients to feel inspired to live their best lives, using intention and actions and financial planning as the process. Because I think it is such a big thing. So financial inspiration is about changing that relationship with money and using it as a good thing, and not about what it won’t allow us to do, but about giving us all flexibility and attractive options that we desire in our life. The last part is that we all want to be remembered for something. We don’t want to be forgotten. And if I can leave behind that I get to financially inspire communities, whole communities, starting with one person, one family, one business at a time, then even though I don’t have children, I’m going to leave something behind for generations beyond me.”

I’ve noticed a theme in our conversation. Sara thinks of what’s possible and looks at the opportunity versus the obstacle. She often looks at what gives her an advantage in her career versus a disadvantage. So, I would say her mindset is a huge part of what has helped her get to where she is and where she is going to help leave that legacy. I close by asking Sara for a piece of financial advice she would want to share.

First, more on mindset,” says Sara. “That comes so much from my mom. My mom is a two-time stroke and two-time stage four metastatic melanoma survivor. She should have died, literally should have died four times. She sees every single day as an opportunity. And so, it’s such a blessing. Believe me, I can get pessimistic about things. I can look down and have those days where I don’t think anything is looking up. But mindset is everything in all that we do. When you see it as a child who has had parents with health issues or who’ve lost their jobs or seen what’s possible for them, if their mindset is positive, it really just shifts everything. So as far as one financial piece of advice, I think it’s to advocate for yourself in your career and heavily in your finances. If you don’t ask, you’ll never receive, and people like to lowball. So, guess what? No one wants to give out more money than they’re going to offer. But if you don’t ask, you’ll never even know what’s possible, so go high. Aim as high as you think doesn’t sound silly. And if they laugh at you, awesome, because maybe you’ve put them off track a little bit, right? Also, you need to have a strong foundation. And I think that understanding that your financial home starts with having a runway. 25% of all people who make over $100,000 couldn’t handle a $2,000 emergency. Understand your benefits. If you are self-employed, make sure you have your own benefits. If you’re working for an employer, I get that it feels like drinking water through a firehose when they send things every November, but then find a relationship that will help you with that. You need to have ownership over your health benefits and insurance benefits. Give yourself enough time to maybe take some of those calculated risks that you desire. So, the first thing is to advocate for yourself. And the second is to lay a strong foundation.”

I remember a leader who once shared with me, the answer is always no unless you ask. And so many of us hold ourselves back from asking. Whether it’s fear, or we tell ourselves a story, or we don’t have that confidence. But Sara has inspired us to take a calculated risk by looking at the obstacles and the opportunities to grow our confidence. By looking within versus looking without, and to step up and advocate for ourselves so we can live the life that we desire. 

I ask Sara to share the best place to follow her and the work she is doing. She suggests her Instagram and website

With that goal achievers, keep celebrating your weekly wins, learning from your lessons and identifying your priorities. So, you can consistently pursue progress in the direction of your goals.