Reginald D: Welcome to Real Talk with Reginald D. I'm your host, Reginald D.

On today's episode, I have Siena Dean.

Siena is a public speaker,

a career strategist,

talent development expert,

and a purpose driven professional who helps people connect the dots between who they are and what they do and why it matters.

Welcome to the show, Siana.

Siena Dean: Thank you so much for having me. I've been looking forward to this conversation. I hope I can be an asset to your audience.

Reginald D: Absolutely. And thank you so much. So, Sienna, can you tell us a little bit about your childhood and where you grew up?

Siena Dean: Yeah, of course. So I'm originally from upstate New York. I was raised primarily by a single mother, but I was surrounded by powerful women and that really helped shape who I became later in life because I had many examples of what it looked like to succeed.

So I had role models from a young age and a lot of people pouring into me.

And so from a young age, I felt like it was my job to go into others.

Since I was primarily raised, though, by a single mother. In the early days, we lived in low income neighborhoods. And so a lot of the schools that I went to, a lot of my friends did not have the same resources that I had.

And that is what sparked my fire to really want to give back to my communities and figure out how I can do my part to make sure that as many people could have the same amount of resources, if not more than I had when I started.

Reginald D: Yeah, that's awesome. We have something to come. And being raised by a single mom, I know how it is.

I know how it is. It was different, but it was good at the end of the day,

definitely.

Siena Dean: It really helped shape who I am and I owe so much of where I am today to her.

Reginald D: That's it. So, Siena, you talk a lot about purpose.

Purpose is the word people use a lot of.

But what does purpose really mean? And how do you align your career with your purpose?

Siena Dean: Yeah, of course. So I love this question because oftentimes,

although it is a word we use a lot, it's not a word accepted in today's careers. Right. And it's a purpose is something when you don't really have bills to meet,

you don't really have other people to be responsible for. Right. That's when a lot of people feel like I can do whatever I want in my career. And where I would shift that definition is purpose is what allows you to take control of your career.

So it is figuring out what are your end goals,

why are you on this earth, and making sure that you are aligning your skill sets and career opportunities to align with the broader purpose or the reason you are doing the work that you're doing.

So it's looking beyond the job to figure out the why.

Reginald D: Yeah, because I always say with careers, here's the thing about careers.

You have a career,

you're doing this. But if you're anything like me at a career, I moved five times in 10 years,

you know, different cities, different states, just blah, blah, blah, blah. And it's like, okay, is this a job or there's something behind this?

Siena Dean: Absolutely.

And often,

oh, go ahead, go ahead, go ahead.

But what I was going to say is, oftentimes we wait for the job to define if it's a job or career. Right. And so based on pay or access to opportunities, then we say, okay, I see some level of longevity here versus figuring out what do I want from various opportunities and using that to say it's a job if it is temporary,

but it's a career if it aligns to where I'm trying to get to in life.

And that's a distinction that I want people to be able to make for themselves instead of waiting for their job or their system or their employer to assign it to them and saying, oh, I really believe in you.

And you get so gung ho on someone else's belief that you're in a job and you don't even know it.

Reginald D: Yeah. So many people feel successful on paper, but empty inside. Why do you think the two purpose and career often drift apart from each other?

Siena Dean: Yeah. So, you know, a lot of the work that I do with my clients is figuring out their why.

So often we end up one, we start running a race, we just continue to run.

And so even though we reach success,

we don't remember why we started on this path anyway.

And that is where I feel oftentimes that emptiness comes into play because we are living for someone else's expectations. We are just collecting the titles, collecting the checks without checking in with ourselves.

Why?

What is the reason behind you show up to work every single day?

And when they do begin to ask themselves that, it is often for the people that, that they have to provide for. It's, well, my children need me to be able to provide in this way.

Or, you know, this is what allows me to have that life that I've always dreamed of versus thinking about.

This is why I felt,

you know, I was placed on this earth. And to get there, you do have to ask a lot of big questions of yourself. And we're not accustomed to having those one on one dialogues with, you know, ourselves, to really reflect and think.

Life is so long. So it's easier sometimes to go on autopilot for a few years and say, okay, I'll just, you know,

run this race and then I'll check back in with myself. But then 10, 15 years pass and we made it somewhere, but we do not recognize ourselves in the mirror.

So where I encourage the people I work with is constantly check in with yourself. Figure out if you're still on that path of where you thought your life was going to.

And if it isn't, then it's time to adjust.

Reginald D: You're so right, Sienna. You're so right.

Because I'll be honest with you, I think a few years ago I was looking at myself and all the things I had going on, all the things I've been doing,

great things, successful things. And I asked myself a question one time.

I said,

who are you really?

You know, and the crazy part about it, when I asked myself that question,

I couldn't answer it.

Siena Dean: Yeah.

Reginald D: Because I was so wrapped up in what I was doing.

And what I was doing was basically I was allowing it to identify who I was instead of getting down to the core of who I really am.

Once I got that and figured it out,

then everything started shifting.

My mindset started shifting, my way of doing things started shifting, and my way of achieving things or going after what was for me shifted.

Siena Dean: Yeah. No. So often even thinking when you meet people,

this is such an American culture, you introduce yourself and you lead with what you do because we allow it to define us.

And then you reflect back and, you know, you stumble over the words and they say you need to rehearse your elevator pitch. Well, you wouldn't have to rehearse if you knew the reason behind what you were doing.

And so it really allows. If you struggle with that question, it's an indication that you might be on someone else's path for your life.

Reginald D: Yep, exactly. You talked about nonlinear careers. How can someone trust their path when it doesn't look traditional or predictable?

Siena Dean: Yeah. So,

you know, this is the time for nonlinear careers.

We are in a very difficult job market right now and a lot of people are carrying a lot of anxiety not knowing when, if mass layoffs are going to come, if they're going to be replaced by AI,

whatever the sort. And so this is a time I really want people to embrace the nonlinear and collect skills.

So gone are the days where blanks in your resume. You have to feel that anxiety because it's becoming common,

mass layoffs are happening all the time, and gaps between finding your next opportunity of employment are continuing to expand, unfortunately.

And so it really is figuring out,

how do you connect the dots and what is your story?

And so going back to your question is once you understand your why,

it becomes less about the actual job. It's about the skill sets that you obtained in working towards this larger picture.

So even if you were in various industries, various levels, and you might have had to take a step back, right. To care for a loved one who recently was sick or you took an extended leave, well, what skills did you work on?

And it becomes a lot easier to connect those dots when it plays to that larger story at hand. When you know your North Star,

then you can make sense of what you know might not seem to make sense on paper, because you can say,

although I entered this industry, it taught me this skill that then better prepared me for this space.

And so it really is about being intentional in each career or each job that you're in to figure out which skills will allow you to get back to your purpose.

Reginald D: Yeah, that's more like alignment. You talk about alignment a lot.

So what are the early signs someone is living out of alignment with their purpose?

Even if they're doing well,

they're doing good.

Siena Dean: So some indications. One, as I mentioned, you know when people ask, like,

nice to meet you, who are you? Or whatever the case may be, and you kind of stumble,

and if even when you answer the question, it feels uncomfortable.

So that might be an early indication, like, huh, that didn't feel like who I am. But that's still my answer. Pay attention to that.

Or if by the end of the day or end of the week, you are constantly feeling drained. Right. Oftentimes when growing up, you know, you would hear a job is just a paycheck, and you really find fulfillment in things outside of your job.

Well, we spend way too much time at work for that to be the case.

So, you know, at the end of the day, yes, it is a job. So you will never love every single thing that you do,

but you should love the majority of the things that you do or the majority of the things that you're responsible for. Right. So if you are going weeks or months and you are just constantly feeling depleted, you need to start taking note of what is depleting your energy.

Is it, you know, the culture that you're a part of at work? So maybe you are aligned in the work that you're doing, but it's not a good Culture fit that is out of whack for your purpose, alignment.

Or you may say, you know, I thought this job was one thing.

So often we are assigned a career path before we even start our careers, right? So you go to college for something and then you feel stuck.

Well, I got this degree so I have to stay in this space.

But you chose that space before you even knew what it entailed.

So if that is the case and you are dreading your days and you're dreading your months, you know, your years,

then you have to have those conversations with yourself and saying, I might have chose the wrong path. And that is okay because you will find so much more fulfillment and so much more success when you are in alignment than any other career path.

It's so funny. I actually went to school for pre law and for the longest I knew I was going to be a lawyer simply because people told me I would make a good one.

The only examples I had of lawyers were what I saw on tv and it wasn't until I was in college and I was like, this is a lot of reading.

Like I can read for fun, but I do not want to do this on the day to day.

And you know,

but still I stayed on path and thankfully I had people in my life to say,

find your purpose early,

find what brings you joy early because you spend way too much time in your career to be unhappy.

And that was a shell shock for me when I was an undergrad in college. Like I was like, my life is over.

I don't know.

I've been on this path for 17, 18 years. Like what am I going to do now? But I'm so grateful I figured that out early on to align purpose with career because I've had extreme success because I love what I'm doing and I know even if I had the title,

even if I had the pay, I would not have found that happiness.

That you know, I can show up and do the work that I'm doing without receiving a paycheck. And that is why I share this information with so many people. It's because there's a genuine joy in helping others find that alignment.

And I wouldn't have had that if I chose another career.

Reginald D: Wow, that's awesome. So you're talking about purpose. Let's go here. Purpose often requires courage. What fears keep people from choosing alignment over comfort?

Siena Dean: Yeah, I absolutely, I love that question.

So I would say purpose feels unfamiliar because you're living for yourself.

Oftentimes we're taught to live for others.

Right. So if you think back to when you chose your career, what was your greatest influence? Was it really what you enjoyed, or was it someone else telling you that's what you would be good at, or that's what would pay your bills, or you have to think about your family,

Right. And so purpose,

where I feel like a lot of people need that step of courage is because it feels selfish,

it feels uncomfortable to live out, you know, to reach your full potential in something and to do it just for you.

Right?

So I would say,

if you're struggling with finding that courage to think about, you know, what do I really want to do?

Just start simple.

What brings me joy?

How do you add like and not just joy in the sense of,

you know, I love ice cream,

I need to eat more ice cream. But what makes you, like, if you had to do one task over and over again for the rest of your life,

or you had to think about one thing for the rest of your life,

what brings you peace? When you think about that, what's that one thing where you're like, you know, being paid or not? I genuinely enjoy this,

or I genuinely love talking to people about this.

And that will kind of put you on that path. And then thankfully, we do live in the time where technology and answers are at our fingertips. If you don't know what a career in that looks like, just put it into one of these AI systems and say, this is what I enjoy.

What does the top levels of this look like? And then you can start to map out a path that will allow you to gain the skills so that you can get there.

And then in that,

I think another piece of where this fear comes from is when you decide to live for yourself and you figure out that end goal,

you tend to dream bigger than you would if you were on someone else's path.

So that end goal feels so ambitious and so scary because now you're dreaming again, you're imagining again,

and then it becomes scary because there's so many steps to get there and you might feel it's too late. Well, I'm ready, you know, mid in my career, will I ever aspire?

Will I ever be able to reach that goal?

But if you break it down into skills, you might find that you already have half of the skills necessary to reach where you're trying to go to. So if you're feeling discouraged,

really reflect and realize that it is okay to live for yourself. You have one life for a reason.

So take back control of that power and say, I'm going to do this for me. And if your goals now feel too ambitious,

don't look at it at all. The career steps that you need in order to get to that end goal, look at the skills that you need to acquire in order to get there.

And the thing about purpose,

even when we're neglecting it, it still shows up in our life.

And so a lot of the people I work with,

when they realize what they are meant to do, they're like, wow, I've actually been secretly pulling myself in that direction for the last 10 years and I didn't even realize.

And so when that happens and they realize, like, I have half of the skills necessary in order to get there,

this isn't so scary because I've already been on that path. I just didn't know what to call it.

So that would be my advice.

Reginald D: So you work with professionals navigating transitions.

Siena Dean: Yes.

Reginald D: How do you rebuild confidence when someone feels lost or behind?

Siena Dean: Yeah.

So confidence is a journey.

And what I have them start with is taking small steps.

So if they feel lost or behind in their career,

I would say map out all the things you feel behind in and then what is one thing that you can cross off your list? So, for example,

if you are independent contributor and you really want to start to manage teams, okay,

what is one thing you can do to start managing people in your life? It doesn't necessarily have to be,

you know, in your position.

Also,

in a lot of organizations, there's ergs, there's way to volunteer outside of your organization in your communities.

So I have them write out the list because oftentimes when you feel lost or behind,

you're not as far behind as you actually think you are.

So naming all the pieces where you feel behind will really help you figure out, okay, what are my next steps? And then where can we cross off things off your list?

And it's about slowly building that confidence where if you've never had leadership experience,

it feels so foreign to you and you're so afraid.

But I'm like, you know, just volunteer for your erg group that you believe in.

And then a few weeks from there, they realize, okay, this wasn't so bad. Okay, cool,

volunteer for a project. There's always stretch projects within organization.

How did that feel? And then as they begin to cross things off their list,

they are reclaiming their confidence and then realizing,

okay, I'm not behind for the race that I actually want to win,

because what I have them make sure they're doing is if you are behind,

make sure it's because you Feel behind, and it's not because you're comparing yourself to someone else.

So if that is the case, once they start building the skill sets, it helps them realize, like, hey, I'm not as far behind as I thought compared to my peers.

But at the end of the day, you shouldn't have been comparing yourself to your peers anyway. So if you're feeling that way, I do have them check in and say,

is it because you feel this way or is it because you see on social media everyone is here, or you feel like in your friend group everyone is here? If that's the case, that's a completely different conversation that we have to work on some internal confidence.

But if it is because you feel that way,

then we can take tactical steps in order to help you build that confidence over time.

Reginald D: So let me ask you this, Ianna. How do people discern whether it's time to pivot, pause, or push through a difficult season?

Siena Dean: Great question.

So the way I have them look at this is in two different buckets.

One is, how many people are you responsible for?

If you are the primary provider in your household,

then you have to look at it a lot differently, because I am still about accountability.

Right.

And you don't want to blow up your entire life if it blows up five other people's lives.

But if you are only responsible for yourself,

then figure out is pushing through that difficult moment, will it bring you closer to your overall goal?

So is there a skill that you need to work on that even though it's difficult, at the end of the day you'll be able to obtain that skill?

Do you need to learn how to navigate challenge?

Challenges feel unfamiliar to people.

And so anything that feels too difficult, they're like, okay, time to abort. Do you need to build that skill?

Then I would suggest that they work through it,

but if they don't, and they were like, you know, I'm comfortable with challenge, but really this problem does not align to where I'm trying to get to.

Then it is okay to pivot. I tell myself all the time not every problem is meant for me. Right. And people will constantly put their problems on your plate. And.

And I'm like, actually, I'm full, You know, so that is perfectly fine to say, hey,

I appreciate you feeling that I have the skills necessary to help us solve this problem,

but I'm actually going to focus in this space.

And so if that's the case,

feel confident stepping away from that problem, pivoting. And if the organization or their job itself is the problem,

you know, it is also okay to pivot to something else, but if that is the situation,

I would have them test the waters.

So often we find where we are, it's not working and we completely abandon ship and we're like, I quit, I only have to provide for myself. It's fine, I'll figure out the next thing.

They find the next thing and they are equally unhappy.

So what I would say is take a deep breath, learn how to deprioritize things at the job that is stressful, that aren't important to provide extra mental space to figure out where else you can invest your skills.

So if you have a job that you hate, that you find extremely problematic,

streamline where you can so to give yourself some extra free time. And then you invest that time in whatever you think would come next.

So if you are,

I don't know,

in banking, you want to jump into marketing,

Find if there's opportunities within your organization currently to start practicing those skill sets. See if there's a project you can lead or be a part of the marketing for. See if there's opportunities outside of your job in your community and wherever you volunteer.

If there's opportunities, start to practice those skills or doing that job you think you're meant to do instead before you fully commit and give it, you know, be realistic with yourself at least two weeks to a month to really invest energy into it before you say, okay,

actually,

you know, I am supposed to be doing this and then figure out how to make it a full time transition versus just assuming it's the best next step. And then you end up right where you were the last time.

Reginald D: Yes, exactly. And then what I hear and what I like about what you're saying, if I put it all together,

no, it's more like steps.

And I always tell people it's steps to everything you do. And then it's also moments. It's how you handle the moment. You worry about the whole thing,

but you got to handle each moment right to get what you're trying to do.

What advice would you give to someone who feels pressured to figure it all out right now?

Siena Dean: I would say, where does that pressure come from?

Is it necessary? Oftentimes it is not right. We often feel like time is fleeting, but when you think about it, you have years,

if not decades left.

So I would really have them reflect and realize where's that pressure coming from? If it's from them and it's not necessary, remove it, break it into steps, take your time.

Because when you stress and execute too Quickly, before you have the necessary skills,

it can dissolve just as quickly in the few cases that it is necessary.

You know, I would say break down that goal. Maybe you aren't reaching your fullest potential, but you're getting halfway.

What is something more realistic you can do instead of, you know, flying to the moon, Maybe you just build a spaceship or whatever the case is. So if it is necessary to solve everything at once,

I would have them really think long about what they're trying to solve and see if it's possible to only get halfway for the time being and if that will solve their problem.

Reginald D: Right. So, Sienna, looking back on your own journey, what did purpose require you to let go of before you could step into it?

Siena Dean: I would say ego.

Purpose will break you before it builds you.

And you have to take a lot of ambitious steps early on without the proof to back it up. Right. So going back to graduating undergrad,

and I knew I wanted to help people,

but I had no idea what that looked like. And so I had to be comfortable forcing myself into various different spaces. I worked in Clean Energy. I worked in early childhood education.

You know, I did a lot of consulting work, and a lot of those spaces felt extremely foreign to me. I was just like, oh, my gosh, I hate this. I just want something I'm good at.

But you have to continue to like. You have to get comfortable being uncomfortable when you're trying to find your purpose. And when I did realize what I was meant to do, it was just as uncomfortable because I realized that I was going to transform professional development.

And early childhood education at the time felt like two opposite ends of the spectrum. And so I had no idea how to couple those things together.

So I had to put it pen to paper and realize what did that dream role look like?

And at the time, I thought it didn't exist. And I was like, this is a problem because, you know, I am fresh out of undergrad and I can't just go work for myself at this time.

And so it caused me to have a lot of uncomfortable conversations with people to figure out, okay, how could I map out a path that would eventually get me here?

And once I figured out that path, I ended up actually writing a business proposal to one of the largest charter schools in the nation to prove to them that they could invest in education and professional development.

And again,

I'm might have been 22, 23 at the time.

And I would pitch it to anyone that would listen to. Eventually,

I was speaking to the director of all of Alumni Engagement for this Charter school.

And I remember she was like, I have five minutes, but if you're ever in California,

I'll hear you out. And I was in New York, and I was like, I'll be there next week. No idea how I was going to get there,

but this was the first time where I felt that alignment. I was like, this is what I'm supposed to be doing.

And, you know, thankfully, I was able to find my way there, But I had never,

like, I hadn't even started my career. So the idea of pitching to this person that was responsible for hundreds of thousands of alums at this time was extremely intimidating.

But when I thought about it through the lens of my larger purpose is intimidating. And so I needed to build those skills that would allow me to have the confidence necessary to reach my goals.

Then I'm like, this has to be small because I'm going much further.

And that is what gave me the confidence to have that conversation. And they actually brought me on as the youngest consultant ever for their organization to help them map out how they could invest in their alums post undergrad at the time.

So.

Reginald D: Wow.

Siena Dean: Wow.

Reginald D: That's amazing.

I mean, I was telling somebody other day that was going through something. I was like, they was looking at the world like, the world is so big,

and it's so competitive and intimidating.

And I was like, no. I said, actually, the world is small.

Siena Dean: Yeah.

Reginald D: You know, I said, you just got to get bigger, you know, within you.

Siena Dean: Absolutely.

Reginald D: That's it. And go for what you, you know, what you desire. You just got to get big. It's. It's small. You'd be all right.

Siena Dean: Absolutely.

My biggest tool that I use whenever I'm feeling intimidated,

and that still creeps in because we're only human.

I realize you're just talking to another person.

We're all people.

Oftentimes when you have that fear,

it's because you're only seeing their title or you're only seeing what they're accomplished. But when you realize in preparing for talks sometimes, or introducing myself to people in the organization that I'm part of, or, you know, I also work with a lot of senior executives,

and I would have that anxiety at first, and then I realized, if you met them at the grocery store, would you be intimidated? If you met them at Pilates, would you be intimidated?

So, you know, it helps you change your frame of mind and the way you look at that person and, you know, you still maintain the respect and all of those things, but you're able to have a conversation and connect on a way deeper level than you ever would have if you only looked at their title or only looked at what they accomplished.

And where, you know, I found a lot of success is talking to people as people.

So I would also advise thinking about anyone, any space that you feel uncomfortable in and realizing,

you know, there's just other people surrounding you.

Reginald D: Got it. So, Siena, I have what I call quick fire questions.

Siena Dean: Oh, exciting.

Reginald D: There's no right or wrong answer. Okay, the first one. One word that best describes living on purpose.

Siena Dean: Alignment.

Reginald D: Okay. Purpose or paycheck, what should lead first?

Siena Dean: I don't think that's easy. The question again, please.

Reginald D: Purpose or paycheck, what should lead first?

Siena Dean: Purpose.

Reginald D: Got it. What's more dangerous? Fear of failure or fear of starting over?

Siena Dean: Fear of failure.

Reginald D: A habit that keeps people disconnected from

Siena Dean: purpose, waiting too long.

Reginald D: Got it. Finish this sentence. Purpose begins when you stop. Wow.

Siena Dean: Living for other people.

Reginald D: Wow. That's it. That's it.

Siena Dean: I like that.

Reginald D: That's it.

So, Siena, lastly, let me ask you this. How can my followers connect with you and sign up for your program and all the other stuff you got going on?

Siena Dean: Yeah, so my website is actually currently in development, but currently you can follow me on LinkedIn, connect with me on LinkedIn,

and that's where I share all of my UPD updates on my upcoming speaking engagements,

which is Siena Dean, my name@LinkedIn.

Reginald D: There you have it. Siena Dean. Siena, thank you so much. I really enjoyed it. Man, you are, wow. You're amazing.

Siena Dean: Thank you. I've enjoyed this conversation as well. Thank you for having me.

Reginald D: Absolutely. Absolutely.

Thank you for listening to Real Talk. Reginald Dee.

If you enjoy listening to Real Talk, Regina D, Please rate and review on Apple Podcasts. See you next time.

Siena Dean: Bye, everyone.