It's Never Too Late to Pivot: Finding Purpose and Creating a Career You Love with Siena Dean | #260

👉 Start Your Second Act Strategy Call with Shannon here.

What if the key to a successful career transition isn't starting over, but connecting the dots of everything you've already done?

In this inspiring episode of the Second Act Success Podcast, Shannon Russell sits down with purpose-driven leader, career strategist, and Senior Alumni Engagement Manager at Management Leadership for Tomorrow, Siena Dean, to talk about finding purpose, building confidence, and creating a career that truly aligns with who you are.

Siena shares how she intentionally designed her career around helping others, why it's never too late to pivot, and how self-reflection can help women create meaningful second act careers. Together, Shannon and Siena discuss career reinvention, confidence, childhood influences, purpose-driven work, and the importance of living life on your own terms.

If you're considering a career change, navigating a midlife career transition, or wondering whether you're on the right path, this conversation will encourage you to trust yourself and start building a life that feels aligned.

In this episode, you'll learn:

•  How to discover your purpose and create a meaningful career 
•  Why it's never too late to make a career transition 
•  How to connect the dots between your past experiences and future goals 
•  The importance of self-reflection and quiet time 
•  How confidence is built from personal power, not perfection 
•  Why women often struggle to define success on their own terms 
•  How to identify what truly brings you joy 
•  Why your second act career doesn't have to make sense to everyone else 
•  Advice for women considering entrepreneurship or career reinvention 
•  How to begin creating a life you're proud of 

Whether you're leaving corporate, exploring second act career ideas, or searching for more purpose and work-life balance, this episode will remind you that your story is still being written.

🔗 Get the full show notes here!

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Transcript

Transcription:

Second Act Success Podcast

Season 1 – It's Never Too Late to Pivot: Finding Purpose and Creating a Career You Love

Episode - #260

Host: Shannon Russell

Guest: Siena Dean

Transcription (*created by Descript and may not be perfectly accurate)

[00:00:00] 

Shannon Russell: Hello and welcome back. I am your host, Shannon Russell. I am about to introduce you to my guest, Sienna Dean.

Sienna is a purpose-driven leader working in the learning and development space who has helped more than five hundred professionals align their purpose with career success. Sienna is known for helping people connect the dots in their careers so their stories make sense.

She is currently serving as the senior alumni engagement manager at Management Leadership for Tomorrow, a national nonprofit transforming the face of leadership by equipping diverse talent to rise to senior business and societal roles. It's time to introduce you to Sienna Dean.

Shannon Russell: Siena, welcome to Second Act Success. I'm really excited. 

Siena Dean: I'm excited for our conversation, and hopefully to give your guests some insights tonight.

Shannon Russell: Our messages on a lot of things are so similar, so this is gonna be really [00:01:00] fun and really insightful for the listeners. But let's take it back. Where did your career begin? 

Siena Dean: In preparation for our call, I was thinking a lot about that. And my career actually began where I feel like a lot of people's middle point tends to be and when they start thinking about this second act, where I realized at a fairly young age I wanted to be extremely intentional and purpose-driven in my career. So I allowed that to drive me from the very beginning, which I feel oftentimes we feel we just have to start, right? And I am grateful I had the opportunity to think about, what do I want my endpoint to be, and that kinda dictated how I began my race.

 I knew I wanted to help people. And I did any and everything that allowed me to help people until I could pinpoint, okay, I wanna help people in this light. So I started [00:02:00] pivoting very early in my career, trying to figure out, where's that sweet spot, but allowing myself to still be driven by f- purpose.

Siena Dean: I was able to save myself a lot of time, where I feel like oftentimes many people, they start and they stay on a race. 

And it's not until they're halfway through or almost at the finish line that they realize it wasn't the race they wanted to begin with which is unfortunate, and that's why I'm so happy I get to help people understand that it's never too late to start anew or veer paths or whatever the case may be.

Because when, you're young and only living for yourself, it's, it was way easier for me to say, "This isn't mission-aligned." "On to the next thing." Now I help other people find that courage to do it in their careers. 

Shannon Russell: So you wanted to help. And how did you end up where you are now?

 That's a great question. So starting out, knew I wanted to help [00:03:00] people. That put me in different spaces like clean energy working with children doing some consulting work on just professional development side. And then eventually in actually doing a consultant stint helping a national a charter school figure out how they would help prepare their alums for the stage after undergrad- Oh

Siena Dean: and map out their careers. It led me to find one of my early mentors that said, "You need to be doing this full time. You are, you're really passionate about it. You're able to help people on scale, and here's an organization that has been doing this a little longer than we have, so they have a lot more resources."

That's how I landed in the role that I have today. And thankfully, one, I had that mission alignment, and that was the point where I realized this is my purpose. My purpose is trying to help people figure out how to make the most of their [00:04:00] career and really live for themselves. And I feel like oftentimes we wait way too long to live for ourselves.

And so once I had that sweet spot where I I get to do this and get paid that's how I landed where I am today. 

Shannon Russell: That's what you wanted to do, and that's what you intentionally set out to do- ... is to serve your purpose in helping others with your career.

And here you are helping others find an aligned career as well.

, A lot of synchronicity

Siena Dean: it really is. And I think, you are able to get there a little bit sooner when you start with that intention. Because, oftentimes when you're going into your second act or ready to pivot and live for yourself, you have to do that work of saying what does that even look like?

And so since I started that at such a early stage in my career, I also was able to play with self-discovery of okay, what really makes Siena tick? And I didn't have all those [00:05:00] years of having to pull back the layers of, like, when was I last happy? I started my career looking for happiness and purpose.

So it was easy, easier I would say to know what it looked like once it landed because I didn't, I wasn't jaded. I wasn't, living the wrong race for too long. I was looking for the right from the beginning. 

Shannon Russell: I don't think I've ever heard anyone say that, Siena. Say, "That was what I set out to do," because you're right.

So often you choose a major, you choose that first job, and you're running, and you're like, what's next on this hamster wheel? Let me keep going." And you don't stop to say, "Do I even like this anymore?"

And so I think for you to be so wise to think like that, you really, you did yourself a huge favor

Siena Dean: Yeah, and honestly, I have to thank my family for that- ... because I caught many of them in their second act right when I was starting to graduate. I [00:06:00] actually was spending the summer with my godmother, and at the time, I was on a completely different track.

I was on the pre-law track, thought I would be a lawyer. I was like, "That's my path." And for the first time, she asked me why. And I didn't have a answer other than, "People told me," this is the path I thought I was going to choose.

And she sat me down, and she's you only have one life, so I want you to live it for yourself- ... and figure out what that looks like." And at the time, I resented her for that because I was like, "I have a major." "I'm graduating. I can't switch." But I'm so grateful now that I was able to do that self-discovery early- 

Because it has completely shifted how far I've gotten in my career. And now I'm able to help people so much earlier than I likely would've been able to just went on that path that everyone chose. It's so important to now the younger, I have younger siblings, the young, my young mentees- i'm always sharing what does [00:07:00] it look like if you could live for yourself? 

Shannon Russell: Yeah. 

Siena Dean: And encouraging more people to have those conversations. 

Shannon Russell: That's beautiful advice. And right now, just to tell everyone what you do, you are a senior alumni engagement manager at a nonprofit called Management Leadership for Tomorrow.

Who exactly comes to this organization and who do you serve? 

Siena Dean: I have the privilege of working on the alumni engagement side. So I get everyone once they have gone through one of our programs. But you can enter our organization at various point, starting in undergrad. 

They help with professional career development.

They help as early as sophomore year in undergrad, helping you land a job, helping you land internships. But where they differentiate from many other programs is we believe in lifelong development. So even after you graduate from one of our programs, we help you at every stage [00:08:00] of career and life.

So if you are, just becoming a parent, we have resources for you. If you are, now you have access to more income than anyone in your family has ever made because we helped you land that job, we help you figure out the finances of that as well. 

We're doing some incredible work, and that's why I'm so happy to be on the alumni engagement side because that's where I get to really that's my playground where- I am working with people from, early career all the way to the executive level in so many different aspects, from wealth management to family building to whatever you could think of, and that's really how life should be- 

Shannon Russell: Yeah

Siena Dean: ran, right? Because so often we try to do it alone or just with our tight-knit circle. But when you can pour into, we have over 10,000 alums at this point. 

Shannon Russell: Wow. 

Siena Dean: When you can pour into a community and say, "Hey, I'm struggling with this. What does that look like?" And you have, a [00:09:00] breadth of knowledge that you receive in return it makes life a little bit easier and a little bit more doable.

Shannon Russell: A lot of universities will be like, "Okay, great. Here's your degree. Now go." Reach out to alumni if you want to, but there's not that base. So what a wonderful organization for you to be able to work at and really see these people evolve in their careers.

So, so Who are the people that you serve?

Siena Dean: Anyone that feels they need that additional support, right? So oftentimes we serve minority groups that can be, people of any diverse background, women, Different ethnic groups so anyone's available for our services, but those are often the groups that say they need that help, right?

Where it's just like- ... my goal is to end up here, but I'm the first in my family to get there, if I end up there, right? Or I don't have access to the resources growing up, and now I'm here at this prestigious university, but I don't know how to navigate this space, [00:10:00] right? So we have the luxury of not belonging to one university or one institution.

 We have corporate partners as well as university partners that we then plug our different fellows and then alumni into. But being able to have that layer removed, we are able to help as many people that are looking for help. 

Shannon Russell: What's the biggest question that you may be asked from people who are, maybe they started a career and it just doesn't feel right, and now they want to make that move?

What is a problem that, you have to deal with on a pretty regular basis? 

Siena Dean: Oftentimes people know they want to pivot but don't know why. 

Shannon Russell: Yeah. 

Siena Dean: And the why is very important, right? Because it allows you to map out your next step. Because oftentimes when people come to me and they just want to change, they're like, "I can't take it anymore."

But then you repeat patterns if you can't pinpoint patterns. And so I really have them start [00:11:00] to pull back those layers, as I had mentioned before, of at what point did you realize this wasn't the place for you? And then from there, we know what you don't want. Then helping them to realize what do they want.

Shannon Russell: Yeah. 

Siena Dean: It's unfortunate because for many of the people I work with, they don't remember the last time they found genuine joy- ... in what they did. 

And so it is often going back to childhood, where it's oh, I really did enjoy, when I wasn't thinking about career and I just did this.

And that's a great place to start, but, humans are ever-evolving, so it doesn't mean we necessarily will find joy in that now. So I always have them test the waters. What is a sandbox you can play in to see do I still find joy and purpose in that? And if you do, then we can map out, like, how you can potentially make a career out of that.

The why, and then where do you actually find that genuine sense of joy and purpose? [00:12:00] 

Shannon Russell: Which are questions that a lot of people don't ask themselves, and I was just thinking back to my own experience of, it's generational, like you said. And I don't remember anyone in my family loving their work.

It was, "Oh, I gotta go to work today." So you don't have that example that you should- Nope ... find a career that will bring you joy and align with your values. But it's possible. And so you're- It is ... really bringing that out in people, and it's probably a lot of work to do that. 

Siena Dean: It is, and that's why, my other passion is supporting early childhood development because it, it's so ingrained, especially I think in our American culture-

You work for a paycheck. And even when I start to have these conversations about purpose, they're like, "That's a luxury. I don't ... I work to pay my bills and find joy outside of work." But we spend majority of our days at work. "You are sacrificing way too much of your life for something you don't enjoy."

And how do we shift that narrative from as [00:13:00] early as childhood of saying your life is worth living the way that you want to live? And how can we take the necessary steps that you also are em- gainfully employed by doing what you love? And I think, we live in such an interesting time where AI, I think, will eventually allow us to do it, and this might be semi controversial to where everyone feels AI is going, and it can definitely go there.

I believe, it could get to the point where it replaces everyone. Yeah. But if we reclaim our power to say, "I'm going to use these tools to figure out where do I find purpose, where can I test the waters, and then use that to t- train myself," you have so many opportunities and live so many various lives during your span of your career because knowledge is now at our fingertips.

And how do we give those same tools to our kids so that they're not just waiting to collect a paycheck? And that [00:14:00] was, from a very small age. I'm like, that's was my path until they said, "It doesn't matter. Even if you don't make a lot of money or you don't, have that cliche career that everyone aspires to have, if you're happy it will be enough."

And that is true. And often when you do find genuine happiness in the work that you do, you make way more than you would 

Shannon Russell: Yeah ... 

Siena Dean: if you weren't because you are willing to put in the extra hours, you are willing to put in the hard work because you genuinely love it.

Shannon Russell: And I, I'm just nodding along yes to everything that you're saying. And I love that you talk a lot about connecting the dots and building a story you're proud of because I talk about that all the time because I do believe there's a correlation between what you started out doing and what it is that you want to build in what I call your second act, and it's just finding a way to, to create that narrative and pull that thread or, as you say, connect those dots.

So I know what it means to [00:15:00] me, but tell me about what it means to you and how you work with your clients to do that. 

Siena Dean: For me, it means figuring out- What's your end goal, right? And in our beginning of our conversation, we talked about at the end of the race, you didn't even realize this was the race you were running.

Oftentimes you find that you don't think five, 10 years down the line. You do it early in your career "Oh, I wanna get to this title by, 30 or 40," or whatever the case may be. But you're not really thinking of if, what does my life look like at 40 or 50 or whatever the case may be.

And I have them do that work, if you can map out your day and it no longer was about the career, simply what were you doing? And then you can work backwards. So for me, once I realized, okay, in the ideal situation where the last things I wanna be doing before I retire and just- 

Shannon Russell: Yeah

Siena Dean: Stop working in general, this is what my day looks like, [00:16:00] then you are way more flexible on how you get there because you know where at least where you're going. Where's the end journey? So that is why when sometimes my career or other people's career doesn't make sense to the naked eye, they're able to still connect the dots to say, "This is still how w- the skillsets I gained still allowed me to get here."

Yeah. And it's less about the job or the career. It's about those, building those muscles that will allow you to get to that end point, and that's where I have them focus. 

I think that's so smart. I love everything that you just said because it is. It doesn't have to fit perfect, but you're saying, "Oh, no, the skills I used in this role can really help me, excel in this new one."

Yeah. "So let me talk about that when I'm talking to people, when I'm at my job interviews and all of that." It's it's all about the messaging when it comes to that too. 

And taking ownership of your story, right? Yeah. Because oftentimes we're like, "Oh if it doesn't make sense, I'll just [00:17:00] cut out that piece."

But that's a chunk of your life that you gained something from. 

So how do you incorporate that back into your story? 

Shannon Russell: Yeah. 

Siena Dean: You're showing that you have been living with this intentionality, even if you didn't know it. 

Shannon Russell: I'd love to know about your confidence formula. 

Siena Dean: I've had the luxury of being surrounded by a lot of powerful women in my life, and I'm so grateful for that. So it allowed me to build my confidence I think a lot earlier than a lot of women have the luxury of doing. Where oftentimes my peers were told to stay silent to be seen, not heard.

All the cliche things unfortunately women are told. And I had the opposite script. I had a mom that if I wasn't carrying myself with the self-esteem that she knew I had, she's "Walk back through that door." And I was like six. And I was like what does this mean?" But it really shaped how I saw myself and took ownership of it, right?

[00:18:00] Where I feel confidence comes from allowing us to define ourselves versus allowing society to define us. And once you have that power, you realize it is power. So I can pick and choose what s- parts of myself I show up as. It, let it be, professional, mother, speaker, but when I know I have that control and power and all of that comes from me, you show up differently because you're not waiting for anyone to give you that permission.

That's how I operate in confidence. But when I work with my clients, especially women, I have them figure out- What allows them to feel most genuinely powerful? When you say confidence, it can feel a little foreign. But we can reference a point of power.

, Many people know what power looks like. There's no right or wrong answer in this space. Because oftentimes for a lot of the women I work for, it has nothing to do with work. 

They're like, "It's when [00:19:00] I just got my hair done." "And my shoes fit just how I want."

And but those are the little moments, and then we can pull back and say, "Okay, here's what your unique formula looks like." "And how do you force that formula into spaces that it doesn't show up in?" And if it is when you get your hair done, do you have time to get your hair done before a big meeting, or those shoes, or those, whatever the case may be.

And then, oftentimes I'm working with people for a significant amount of time because this is a free resource for them. Yeah. They come back whenever they have questions. But then you can build off of that. Whereas to just say, "Did your hair exactly look perfect?" May- maybe it didn't, but you still have that confidence. Okay, what else do you think led there? And then we can figure out, when they realize it's not about those little things, it's simply how they decide to operate in their power. Yeah. And then we can, continue to build from there. But that's how I find, and that's how I try to help [00:20:00] others.

Shannon Russell: I love that. And that's something, too, that you can ingrain in children at a young age. You were talking- ... about the early childhood piece. And you are a mom, and I'm a mom. So how are you using a lot of this with your- ... own children to teach them about confidence and about wanting to create a career that isn't necessarily about the paycheck?

Siena Dean: Yeah. So I have the luxury of having a boy and girl, and I was like, "Oh, this is the perfect use case." 

Shannon Russell: Yeah. 

Siena Dean: I get to try different things but it also allows me to figure out, okay- all operate differently, and so let me not pretend that there's a one fix. And I know that with my clients and the people I work with, but sometimes parenting you try to keep it as uniform as possible because- you don't want any kids to feel different, but, they are. They 

Shannon Russell: are. 

Siena Dean: And so where I try with my children is to just be authentic because I [00:21:00] think, as a child, even though I had a lot of these lessons instilled in me at a early age, which I was grateful for, I still had all these adults on a pedestal.

And when you do that, this idea of adulting feels so foreign and so complicated. And so I'm just honest with them. I explain things and I'm still working on what's the best delivery sometimes for my kids so they absorb it and it doesn't then, put my burdens onto them, 'cause that's never my intention.

But I think we have to start realizing the things that we wish were different when we were adults and when we were kids, how do we then share those lessons early on and not wait until they are going through the exact same thing? 

And in that, how do I live authentically and honestly with my kids to let them know "Hey, you may have to face this, and here are some options that you might have.

And knowing that you can come to me whenever, and I will be here [00:22:00] to help you work through those things." 

Shannon Russell: What a good mom to have. I love that. Yeah. Them and all of their friends are gonna come to you when it's time to apply for college and look for that first job. Siena, I don't wanna keep you much longer, but what kind of advice do you have about pivoting, about finding your true purpose and passion in life for our listeners?

Siena Dean: For pivoting, I would say it's never too late. Just do it. I've listened to some of your episodes and I completely agree with you. It is ... Just rip that Band-Aid because your life is so short. I actually was just speaking with one of my girlfriends about this. And she was just, she wasn't ready to make that leap.

And I'm like, "Okay, but what does three months give you? What does one year give you that you can't do right now?" Doesn't mean you, drop everything or quit everything. But how do you start walking towards that goal? And so I would say anyone that's looking to make a pivot, plan it out, map it out, [00:23:00] take those small steps that will allow you to eventually get there.

Because momentum, . it's like a snowball. Once you start, it will continue to build traction. So just start. And then on the other side in terms of just advice in general, I would say, on purpose, it really, it comes with self-reflection. And I think more and more we're getting away from that, unfortunately.

So often we're living in the now, After work, we're not really present with ourselves. We're jumping into other things. We're on social media, things of that nature. And so I would just start with quiet moments with yourself. Don't put anything on the agenda, just sit in silence.

My family does this amazing thing where, at least several times a week, we just sit in silence. And you won't realize how foreign it feels. The radio isn't on, the TV isn't on. Nothing. And it's about g- being comfortable with yourself. And once you start feeling that comfort in [00:24:00] silence, then you can start to put things on the agenda and say, "Okay, I'm feeling uncomfortable in these spaces."

"What would my comfort looks like?" Or, "How can I start to pinpoint what exactly made me uncomfortable?" And the more you get to know yourself and what you do enjoy, then it will start to give you a path to finding lifelong purpose. 

Shannon Russell: That's beautiful. Beautiful way to wrap things up. What a conversation.

So much good stuff. And I do want to ask you, what's next for you? What is your next act? 

Siena Dean: Yeah, so great question. I am in the process of becoming a mom again, one sober. So I've been really intentional with that, figuring out, there's something beautiful in parenting and how it shifts what's important for you.

And this has been my most significant shift, where it's just like I knew, where my end goals were. But once I became a mom, it really, it helps you align [00:25:00] to what's really important. And more and more, childhood development has become what's heavy on my heart, so I'm taking those steps, right? I'm walking towards to see what that looks like.

And right now I'm, mentoring a lot more younger people, but I'm also in the process of figuring out if that was my full-time career, what would that look like? And so that is this next act that I'm moving towards, where I always thought it would just stay on the adult side. But more and more I'm like, let's heal, or before the damage is even done, what lessons can we learn and .

how can we better prepare that next generation? So that is where I'm moving towards. 

Shannon Russell: That's a beautiful mission. That is fantastic, and so needed. It's we forget about that early education piece when it comes to thinking the bigger picture and- yeah ... so I love that. I'm excited to keep in touch and find out what you're doing once you're on the other side of this new motherhood journey.

Siena Dean: [00:26:00] Thank you. 

Shannon Russell: How can everyone connect with you? Where's the best place to find you? 

Siena Dean: I would love to connect on LinkedIn. It's my name, Siena, my last name, Dean. And yeah, I would love to connect. Please reach out. I am, like I said, a connector, so if I can't be of support, I probably know someone that can.

And I'm all about doing this life thing together, so I would love to, to connect.

Shannon Russell: Thank you for being here. I'll link to everything in the show notes. it's such a pleasure, Siena, to get to talk to you and learn all about the amazing work you're putting out into the world, so thank you.

Siena Dean: Yeah, this was awesome. I'm so happy that I was able to join, and thank you for your questions and taking the time to have this conversation with me.

Speaker 2: Thank you for joining me for another episode of the Second Act Success podcast. If this episode has you thinking about starting a business or growing the one that you already have, I offer free Second Act strategy calls. This is where we map out what makes sense for your business and your life. You can book [00:27:00] yours now at secondactsuccess.co/strategy or grab the link in the show notes below.

As always, thank you for being here. Until next time, I'm your host, Shannon Russell, wishing you the best day ahead as you plan your second act. I'll see you on the next episode.