Alana Winter spent 25 years building a national video distribution business before realizing she'd built something successful without ever asking herself what she actually valued. In this episode, Alana and Maricella talk about being raised by a serial entrepreneur dad who taught her to control her destiny, the moment the business became a grind and she didn't know who she was without it, and the three-year process of figuring out her own core values, and how she helps leaders do the same in a much shorter time frame. They get into the difference between needs, values, and your why (and why most people confuse all three), what she means by "the how matters less than the what," and her story about the bathroom attendant at the Beacon Theater that made me tear up.

About Alana Winter:

Alana Winter is an executive coach, facilitator, and serial entrepreneur who helps leaders navigate the moments when outward success no longer matches their inner truth.

After building and running businesses for more than 25 years, including a nationwide video distribution company and the internationally covered Stiletto Spy School and MI6 Academy, Alana found herself in the disorienting space that comes after a major chapter ends. That experience led her into a deep exploration of identity, core values, and what it really means to build a life and business from the inside out.

Today, Alana works with founders, CEOs, executive teams, and leadership groups around the world, helping them clarify their values, communicate more honestly, make better decisions, and lead with greater self-awareness. Her work blends psychology, lived entrepreneurial experience, and a highly intuitive ability to see the patterns beneath the surface.

She holds a B.A. in psychology from Wesleyan University and has worked with thousands of leaders through EO, YPO, WPO, Chief, and private executive coaching engagements. Her work has been featured by NPR, The Today Show, The Wall Street Journal, Psychology Today, and other major media outlets.

Show Notes:

(00:00) - Nothing To Do Identity

(00:21) - Show Intro And Premise

(00:52) - Purpose Values Episode Setup

(02:05) - Meet Alana Winter

(04:54) - Childhood Dreams Icebreaker

(06:19) - Raised To Be Entrepreneur

(07:37) - Building Video Distribution

(13:10) - Meaning Fades Business Grind

(16:16) - Betrayal And Embezzlement

(23:09) - Burnout Signs And Body

(25:57) - After the Exit Void

(28:09) - Meaning Over Opportunity

(30:33) - Purpose Work for Kids

(33:34) - Three Year Values Quest

(38:15) - Values Needs Why Framework

(44:20) - Living Values Anywhere

(47:16) - Clarity Becomes a Calling

(50:06) - Advice for the Goo Phase

(52:18) - Podcast Closing

What immediately hit me was like, I'm done.

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I have nothing to do.

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There will be no emails coming in,

there will be no phone calls coming in.

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I have nothing to do.

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And.

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Who am I if I have nothing to do?

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Oh, that feeling.

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Oh, I know that feeling.

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Have you ever felt like the script you're

following doesn't quite fit anymore?

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Then you're in the right place.

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I'm Rera and I started.

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Should I just quit my job after

walking away from a job I.

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To find me, forget the highlight reels.

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Here we talk about the messy middle,

the doubts, the detours, and the chaos

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that come with rethinking who we are.

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Because the truth is it was

never just about quitting a job.

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It was about questioning

everything I thought I knew.

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Hi everyone.

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Thanks for joining me.

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I am a little behind.

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With episodes, so I apologize I couldn't

post this episode last week, but maybe

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that means you'll get two weeks in a row.

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I have a couple that I've been working

on, this being one of them that I think

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will be ready to go pretty soon, but

I'm happy to be here and I'm happy to

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share this conversation today because.

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I've been wanting to post

this one for a while.

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It touches on something that I think

is really close to my heart and also

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something I've been thinking about

a lot, which is purpose and finding

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purpose and our why and our values.

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And I know those words sound like

something we throw around, but

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I do think they really matter.

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I do think that clarifying

those can really help us.

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The path that we're gonna move

forward in a way that feels

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grounded, that feels worthwhile.

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And so you're gonna listen to my

conversation with Elena Winter.

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She's an executive coach, a facilitator,

an entrepreneur, serial entrepreneur.

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Ran a business, started a business,

and ran a business for like 25 years,

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and it became this big national.

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Video distributor, which is

like a type of business that

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I don't get to discuss a lot.

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So that was really cool.

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But Atlanta moved from that world, from

that chapter to the next one in a way that

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had her wondering like, what do I want?

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Who am I?

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These questions of

identity and core values.

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What it really means to build a business.

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That's something that

you care about deeply.

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I mean, she cared about her business,

but it's something that comes from

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a deeper, deeper level of purpose.

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And Alana did the work to

clarify those things for herself.

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And now.

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Helps others, helps particularly

leaders do that work so that they can

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navigate messy middle of change, that

they can manage these identity shifts

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so that they are not tied to that

role or title, but can go much deeper.

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And it was interesting to talk to Alana

about her journey and about how she

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approaches both now, how she approaches

teaching this or helping leaders go

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through this more than teaching them

how she facilitates these discoveries

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and conversations with leaders,

but also how she did it herself.

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And spoiler alert, the person

who helped her figure out her own

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why is probably the person who.

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Knows more about this than a

lot of people in this world.

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He's very much an expert make of that.

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What you'll, or just listen

to the episode and find out.

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It was really great to have this

conversation with Alana, and

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I'll be honest, after it, I kept

thinking about my own why and my

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own values and my own purpose.

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I think I have to do more work

exploring it, and I've done some

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and I wanna continue, and of course

I will share once I get to that

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point, but it really inspired me

and I hope it does the same for you.

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I hope you like it.

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I hope it makes you question some things

as well, and I'll see you next time.

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What did you wanna be

when you were growing up?

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A princess.

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I love it.

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No one has answered that.

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I mean, castle and like who doesn't?

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Beautiful dresses in

a big four poster bed.

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I do believe that there's something

about what we wanted that shows a

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little bit about our personalities

that we sometimes forget.

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Probably.

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I mean, I still love beautiful

ball gowns, so very playful.

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How about you?

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What did you wanna be when you grew up?

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A writer.

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Mm, A writer.

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I went through faces.

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I think we all do, but that one

was the one that stuck the longest.

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I feel like that's still what

I wanna be when I grow up.

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Yeah.

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Well now I wanna be a

writer when I grow up also.

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But at Three Princess for sure.

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But from Princess to

Entrepreneur is a big jump.

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That's interesting.

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I guess I always saw the princesses

being able to do what she wanted and

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being able to create whatever she wanted.

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So I don't know.

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I think I see, yeah, I can see it.

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Connection.

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I can see it.

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I can see it.

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So tell me a little bit about what

led you, 'cause you did have a

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company for a really long time.

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Alana Winter: So from what we've talked.

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It seems like that was the like

real first big thing, right?

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For you?

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Oh, yeah.

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I grew up in a family of

entrepreneurs on my dad's side.

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Basically, everybody was, my

mom wasn't, but her mom was.

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And so from the time I was little, like

literally from four years old, my father

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would ask me, honey, what kind of business

are you gonna open when you grow up?

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Wow.

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Wow.

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Yeah.

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It was never, what kind

of job are you gonna have?

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That was not a word that I even heard.

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It was, what kind of business

will you open when you grow up?

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It was the only option

that I ever knew existed.

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Wow.

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Mm-hmm.

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I come from a family of entrepreneurs,

but I never had that and I

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never actually thought that I

would become an entrepreneur.

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So sometimes you never

know, but it's interesting.

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That was forever what

you had in your mind.

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It really is.

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'cause I know that it's not the

way that most people are raised.

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Right?

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Right.

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Most people, your parents want safety

for you, and people don't think of

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entrepreneurship as the safe route.

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But the way that my dad explained

to me, my dad always said to me, you

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have to be in control of your destiny.

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Mm-hmm.

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He literally said to me, I was probably

10, he said to me, I don't care if you

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have a hot dog, stand on the corner.

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He said, literally, as long as you

are in control of your destiny,

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that's what it's all about.

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Wow.

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And so you build your company.

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Tell me a little bit about that, because

I know it was what, 25 years that you

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had the company before you sold it.

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And I wanna talk a little bit about

the journey, because I also know there

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were some winding twists and turns.

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Always, as always, tell our guests a

little bit about it, what it was, and.

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When did you start it?

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My main business, I had a few

different ones, but my main business

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was in the video distribution space.

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Mm-hmm.

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Which means that back when you went

to a physical location and you wanted

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to watch a movie and you got physical

medium, a disc or a cassin, and saying

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that because there may be people listening

who never had that experience hunting so.

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Sounds like, wait, you did what?

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And you had these tapes

and you had to rewind them.

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Yeah, so back in those days, I distributed

and I sold to all those stores, you

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know, blockbuster video when it was

first opening and first starting.

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We supplied all of that inventory and

we stocked their stores, and then there

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were videos in convenience stores.

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But what people don't realize

is still to this day, if you

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walk into a public library.

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There's a huge section of DVDs and so

that's still a business supplying those,

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that physical medium to public libraries.

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It's a huge source of traffic to them.

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There are plenty of public

library systems that have a

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million dollar budgets to to buy.

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What led you to that industry?

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It was super random when I was getting

out of school and I had you no idea.

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I started college very young, and

my dad at some point even said to me

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when I turned 17, he's like, well,

I can pay for the rest of college,

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or I could just give you the money

now you could start a business.

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He said, I'll never give you another dime.

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This is your only option.

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But at 17, I knew that.

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I had no idea what I was gonna do, and

I knew enough to know that I didn't

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know how to manage that sum of money.

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So I said, dad, pay for school.

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I'll figure out a way to get money

and start a business on my own later.

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But for now, I wanna stay in school.

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So when I graduated from college and

I went off traveling for a bit and

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I came back and I remember my dad

picked me up at the airport and we're

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driving home and he looks at me, he

is like, so whatcha gonna do now?

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And I was like, what do you mean?

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He's like, well, you figured

out your life, right?

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And I was like, uh, wow.

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No.

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And for the first time my dad looked at

me like, what are you some kind of loser.

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He said, oh my God.

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And he said, okay, listen.

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I opened up a video store.

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It's this pretty recent thing.

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He said, I will give you a job as a clerk.

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I will pay you minimum wage.

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You have a job for one month.

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Mind you, it was over an hour

away that I had to drive each way.

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By the way, also, he said,

you have a job for one month.

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You have one month to

figure your life out.

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Mm.

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I was like, oh, okay, sounds good.

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So the next morning, literally I got in my

car and I drove an over an hour up to the

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boonies to, to work at this video store,

and the month went by, and of course I

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hadn't figured my life out in a month.

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Surprise.

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But on the last day of the month, my

dad called me and he said, okay, I

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just found out the manager is stealing.

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So you still have a job, you've been

promoted to manager of the store.

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So I worked for my dad for.

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Another few months went by and

then my dad's like, okay, I

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wanna open up some more stores.

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And we looked around at the inventory

and at the time to stock a video store,

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it was really expensive to buy a tape.

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They were over a hundred

dollars wholesale.

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He said, but you know what?

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There's some other stores and I bet

they've got inventory that slowed down.

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Let's go drive around and visit some

other stores and see if we can pay them

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cash and buy some inventory from them.

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They'll be happy about it.

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We'll be able to open our

store at a lower cost.

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Store at a fraction of the cost of what

other people were opening stores at.

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And then we opened up another one.

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Another one.

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I was helping him with all of this.

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And a year goes by, I am still working

for my dad, managing his store.

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And one day he calls me

and he goes, you're fired.

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And it's like, uh, okay.

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And by the way, he says, you know

how we opened up stores and we

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saved a lot of money in doing that.

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He said, I bet there's a business there.

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I was like, okay.

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And I hung up the phone and it

took me a few minutes to put two

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and two together and figure out

what he was actually saying to me.

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So I called him back five minutes later

and I said, Hey, you know you've got

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some excess inventory in your store.

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Can I take that on consignment and use

that to start a business doing this?

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And he is like, yep.

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So by 3:00 PM that day, I was in business.

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So that's how I got started

and that's what I did for.

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25 years and it expanded from working

with stores all around the country,

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buying their excess inventory, buying

overstock from eventually the studios

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and manufacturers, et cetera, and then

winding up, supplying, as I said, like

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blockbusters, they were starting to bomb

and pops to convenience store chains, to

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public libraries all over the country.

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Maricella Herrera: So

built into distribution.

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Wow.

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I love this story.

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Your dad clearly has had an incredible.

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Impact and impact your trajectory and

how great to have someone that pushes

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you to figure out your life, but in a way

that is helping you take control of it.

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Yeah.

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That was very much a

fly little bird of time.

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Alana Winter: Mm-hmm.

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Mm-hmm.

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You know what's interesting

about all of that?

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Marcella though, I went into

that business, there was an

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incredible market opportunity.

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I was super lucky to just be at that.

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Point to see that market

opportunity and to be in a

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position to take advantage of it.

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And I am very grateful for that.

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And on the other hand, another thing

I'll say about that, it was, while it

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was a fantastic opportunity there and it

provided me entrepreneurship and freedom

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and all that, if you think about meaning,

there wasn't any meaning in it for me.

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There was nothing in there that spoke

to my soul and the way that manifested,

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well, at first, the business was actually

an amazing opportunity, an amazing time.

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Like any business, when there's an amazing

opportunity, other competitors come

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in, opportunities shrink every market

ultimately become super competitive and

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margins reduce down in any marketplace.

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And that's what happened,

of course, in my market.

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And so that means that

business becomes hard.

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And when business becomes hard, if

you are not doing something that you

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are actually passionate about and that

has meaning to you, life becomes hard.

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And eventually that is what happened.

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And life became hard when

the business became a grind.

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And I would try all

different kinds of things.

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I had a warehouse that was

in Garfield, New Jersey, and

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it was right next to Passaic.

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And there were, there was a lot

of under privileged people living

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in the area, and I try to recruit.

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Single moms, young single moms.

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There were a lot of girls

there that were like 18 to 21

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years old, single and had kids.

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And so I was trying to

make my office a social.

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Good kind of place.

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Mm-hmm.

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But all of that came with its

own challenges and struggles

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also, I got a call on a weekend.

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We had a very busy time, and

sometimes we'd work seven days a

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week if we were busy filling orders.

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And I get a call from a warehouse

manager on a weekend that one of the

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girls, her baby daddy is there with a

knife to her throat in the bathroom.

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Wow.

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And there's like, I mean, crazy,

crazy, crazy stuff was happening.

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But anyway.

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And there were days where I just was like,

Ugh, I don't even wanna go to the office.

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I don't wanna go to work.

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I don't wanna, I don't wanna go

in and deal with this myself.

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And so I found ways I put people in

charge, but you still have to run stuff.

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And eventually I had a competitor

who was one of, I did a lot of

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work with my competitors 'cause

we would exchange inventory when

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one of us had something we needed.

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And one of my competitors who knew

that I really was looking for a way

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to get out of the business, came to

me and suggested that we do a merger.

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And he had.

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Excess capacity in his building

and we could move all of my

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operations into his building.

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And he had staff that could run

stuff and I could really take

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a step out of the day-to-day

operations and it sounded great.

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Maricella Herrera: And so we, we

did that and it was great until my

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business partner started embezzling.

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I was waiting for that.

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Yeah.

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What did that.

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I thankfully have never been in a

situation like that, but it just

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feels like it might shake your whole

view of how you built the thing and

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the trust that you put in a person.

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And I dunno, how did you.

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Deal with it, basically.

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Guess, yeah.

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That was the third time that something

like that had happened to me.

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Alana Winter: So I had a bookkeeper

who I trusted deeply, embezzled,

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forged checks in my name, take a

line of credit out of the bank.

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Really?

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She seriously almost

bankrupted my company.

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We did wind up having a court case

and she was prosecuted and she

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did wind up going to jail for it.

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I had.

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An employee who had come in and cleaned

my warehouse out on a weekend, set

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inventory and stolen leads, and gone

and tried to set up a competitive

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business to mine the first time that

it happened with the bookkeeper.

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When I discovered what she was

doing, that felt like a gut punch.

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Like it felt like literally somebody

had physically punched me in the gut,

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and I remember I called her and I

was just screaming at her and I was

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crying, and I was just hysterical.

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Even in that time.

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What I very deeply innately knew was that

I could not generalize that to others.

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So it never, I never let that

impact my trust in people or the

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way that I operate in the world.

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Unfortunate things happen to people all

the time, and that is something that.

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We have to protect ourselves, right?

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I, I heard once this great

saying somebody steals from you.

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Like that's the pain in the moment.

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You keep holding it in your head, you

generalize it, then that means that

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they're stealing from you again and

again and again and again, and that you

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didn't have any choice over the first

one, but you have choice over the second.

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Wow, we have choices to

what we make things mean.

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So that I very consciously

chose to not let that happen.

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And the second time that it happened,

it hurt not as much as the first time.

345

And it's really interesting the third

time it that it happened with my business

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partner, there was that emotional

reaction and it lasted for a nanosecond.

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Literally.

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It's like it started, the emotions

started to come up and then instantly

349

I recognized and it was like useless.

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What actually has happened

in this situation?

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How much damage has been inflicted?

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What are my options?

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What do I do now?

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What are the actions I can take?

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And that was it.

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And there was truly, with that

one, there was never, I still, I

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harbor no ill will towards him.

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We wound up settling.

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He wound up paying me back

for what he had stolen.

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We wound up selling the

company at one point.

361

He actually.

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Called me and said, listen, here's, I

realize this was really stupid what I did.

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I can't run the company without you.

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Can you come back?

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Can we be partners again?

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I was like, wow, Lulu.

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Lulu.

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But anyway, we wound

up selling the company.

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I said to him, listen, I said.

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If we're gonna sell the company,

you just have to come clean to

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whoever we're gonna sell it to, if

they're going to want to keep you on.

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So we wound up finding another competitor

of ours, and I remember the three of

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us sat down and he told the guy who was

buying the company everything and what had

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happened and what he had done, et cetera.

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And the guy that was buying

the company said, okay, I'm

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gonna, I'm gonna take you on.

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And they worked out a whole.

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Scenario between them.

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I wanted to know part of it, I

wanted to check and I'm done anyway.

380

He called me a year later and

said, I just had to tell you this.

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He said, you know, karma,

what goes around comes around.

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I guess he said, the guy that we sold

the company to has been embezzling

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and hiding profits from me and

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Karma.

385

Karma.

386

Yeah.

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Just, wow.

388

Oh yeah.

389

Again, the way I looked at it,

Mariel, was people make choices.

390

He was in a position, I guess, where

he felt pressure and he felt that

391

this was, he made a bad choice.

392

He made a bad choice.

393

He wound up paying for it,

but it wasn't worth any of my

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emotions to get invested in.

395

Well, honestly, that's so

admirable like that you were able

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to separate it and be kind of.

397

One nanosecond, as you said, and

then move towards what it could be.

398

It made me think of two things that

are kind of woo, but on the one hand

399

it happened three times for you.

400

Maricella Herrera: I dunno if you've

heard this, but I know in Buddhism that

401

we do say that things happen to you over

and over until you like, make it stop

402

until you make the choice, the conscious

choice of this will not happen to me

403

and move forward, which is what you did.

404

It made me think of that.

405

Hmm.

406

On the other hand, would you have sold

the company if that hadn't happened at

407

that moment, like thinking about how

you said there was no meaning for you

408

in the type of work that you were doing.

409

Alana Winter: Like I wonder that

being the catalyst for you to.

410

Move on to do something different.

411

I dunno.

412

I will tell you that many times over

the years, I would decide, I'm done.

413

I'm out of this business.

414

And the day that I would decide I was

out of it, like the phone would ring in,

415

some ridiculous huge deal would come in.

416

So I was like, universe, what

are you trying to tell me here?

417

So, I don't know, had he

not made a bad choice?

418

We had a great position to be

running a company, which frankly

419

could completely still exist today.

420

Yeah.

421

Because I worked really hard to get

the public libraries as clients,

422

and if anybody's listening, if you

can get public libraries as your

423

clients, they're great clients.

424

They're hard to break into,

really hard to break into because

425

they're more systems oriented.

426

Mm-hmm.

427

Like they don't care if they save

25% on their bill, unfortunately,

428

but if they can get more inventory.

429

So I had to learn how to talk to them.

430

And then they really, they're

super resistant to changing

431

suppliers and they pay their bills.

432

So we could have still

had a great company.

433

Yeah.

434

I always wonder about these things.

435

So two questions.

436

I know when we talked back a couple

months, we talked also about like

437

signs of burnout and like how you

start seeing, 'cause you were also.

438

It was like you were saying, it was a

hard business and it was a lot of work.

439

Maricella Herrera: And even if at some

moment you would be like, oh, I'm done.

440

I'm leaving.

441

And then another big thing comes that

also comes with more to the pile.

442

You know what I mean?

443

Mm-hmm.

444

So did you notice, like for

me, I think I noticed how burnt

445

out I was after I stopped.

446

Like looking at, in hindsight,

while I was running, running,

447

running, I didn't see it.

448

Alana Winter: So I wonder if it was

similar for you or if you saw more signs.

449

As it was happening, or what

we can be looking out for too.

450

Yeah.

451

I think that is, people don't see burnout

while it's happening because you can't,

452

you're running too hard to keep everything

in place and kind of, if you stop to

453

look under the hood, it's too, too much.

454

There's no.

455

You keep going until something breaks.

456

Right.

457

And what happens often with people

that breaks is their health.

458

Yeah.

459

And that's really unfortunate.

460

And it would be great for people to.

461

Have something that's built in where

you're paying a little bit more attention

462

to what's happening here, right?

463

What's happening in your heart?

464

What's happening in your mind?

465

What's happening in your body,

and what is that telling you?

466

And then also.

467

Change is really scary because if

you see the signs of burnout, then

468

what do I do with that right then?

469

Then if I leave a situation and

you don't have something lined up,

470

you don't know where you're going.

471

That leap is very scary.

472

So very often it doesn't happen

until you're pushed, you know?

473

I mean, look what you said.

474

Maybe that's true.

475

Maybe that did all happen because

it's finally what pushed me out.

476

I don't know.

477

But it finally did indeed push me

out, and usually that's what it takes.

478

You said about health and then

you, as you were talking about,

479

noticing what's in your mind and

your heart, and in your body.

480

Maricella Herrera: I've noticed more

and more how the embodiment of all

481

of these emotions, like I see it now

more, I've become more attuned, I

482

guess, to when something's not okay.

483

Because I feel the, you know, the knot

in your stomach or the pressure in

484

your chest, and I think you're right.

485

When we're running, running,

running, that's not something

486

we can have the space to see.

487

Mm-hmm.

488

The space to see it and it's too,

then we wouldn't know what to do.

489

Yeah.

490

How was.

491

That period for you after

having sold the company?

492

Wow.

493

So I so clearly remember the day because

in leading up to selling something,

494

there's a million emails and et cetera,

going back and forth and details

495

to work out and the lawyers, and I

remember the day that I got a call

496

from my lawyer saying, okay, it's done.

497

Alana Winter: Everything's signed,

escrow's released, we're done.

498

And I stood there and I was in Italy.

499

I was with one of my friends

and I was on the side of the

500

road when the call came in.

501

I was like, oh, okay, great.

502

And I hung up and what immediately

hit me was like, I'm done.

503

I have nothing to do.

504

There will be no emails coming in,

there will be no phone calls coming in.

505

I have nothing to do.

506

And.

507

Who am I if I have nothing to do?

508

Oh, that feeling.

509

Oh, I know that feeling.

510

It was so unexpected to me because

I always felt like I was part of an

511

entrepreneur's group and everybody

would introduce themselves right

512

away first thing with what they

did, and I would never do that.

513

Like I always thought, oh, I'm not,

my business is one part of me and

514

I do this and I travel and I have

all these different interests.

515

Suddenly in that moment I

realized it shocked me what a

516

huge part of my identity work was.

517

And my friend that I

was with looked at me.

518

She's like, this is amazing.

519

What do you wanna do now?

520

And I was like, I dunno.

521

Get an ice cream.

522

And for a while I.

523

I wouldn't go out to like business

stuff like part of this organization.

524

I said I didn't wanna go to meetings

because if people would ask me

525

what I was doing and I didn't have

an answer, I was like, uh, wow.

526

Yeah.

527

So it was very much a period of

feeling lost wandering in the desert.

528

It's funny, I had a bottle of

wine at dinner last night with

529

some friends and it was this.

530

The wine is called eight Years in the

Desert, and it was from a wine maker

531

because when he sold his company, he

couldn't, he had a non-compete for eight

532

years and this was his first wine and

he called it eight years in the desert.

533

So very apropos.

534

Yeah, it was, I was lost.

535

I was lost in wandering and I knew that.

536

I needed to, in order to

figure out what I did next.

537

I looked back at the journey that I'd been

on and I looked at the times when business

538

was hard and it felt like a grind.

539

And I, when I didn't wanna

wake up and I was like, I never

540

wanna feel that way again.

541

I never wanna go through that again.

542

And so building a business just because

it was a good opportunity, if it

543

didn't mean something to me, I knew the

price that I would pay if I did that.

544

I didn't know that when I started

my business, but I knew it now.

545

So what could I build next?

546

That truly meant something to me, and

I realized I had never thought about

547

what really meant something to me.

548

What were my values?

549

What did I wanna do in the world?

550

What impact did I wanna make, make?

551

I had never thought about that, and now

it was time yesterday I talked to someone

552

who told me he was going through a.

553

Period of time, a long time

ago where kind of dark.

554

And then his therapist

asked him, what do you want?

555

And he realized, no one had ever

asked him that, like he and no

556

one else had ever asked him.

557

But just, I think we do that.

558

We don't wanna see that.

559

Sometimes we just wanna do, see

the opportunities, see the, this

560

more external things maybe in

a way than the internal ones.

561

I do wanna go down the route to

understand how you did that, because

562

I know you've done a lot of work

and help people with that now.

563

Maricella Herrera: But first I also

wanna ask, 'cause this came to mind,

564

and I think we talked about it when

we talked the other day, it's also the

565

different in your period of life, right?

566

Meaning versus opportunity when

you're starting out, when you're

567

building your business, when you're,

I don't know, in your twenties or

568

earlier in life versus when you're.

569

Alana Winter: In a more mature,

gotten to know yourself more?

570

I don't know.

571

I think there's an aspect of it.

572

I joke that I turned 40 and

quit my job the same year,

573

and that's not no coincidence.

574

Like it's, there's something I

believe that changes in us as

575

we start in the way we make the

decisions as we are getting older.

576

Yes.

577

But I think that's contextual

and I think that's because

578

of the way that we're raised.

579

Oh, interesting.

580

I don't think it has to

be that way as an example.

581

I had a client that I had done a lot

of work with, and as you said, now I

582

help people, we'll talk about that.

583

But the work that I had done with

him, he said to me, he's, and he had

584

three, has three kids, and at the time

his kids were, I think seven, one was

585

about 11 and one was 13, and he said,

I wish my kids could do this work.

586

At this stage to set

themselves up for life.

587

He said, could you come and do a

retreat with my family and work

588

with my kids to help them understand

what their core values are and

589

what their vision for life is?

590

I love that.

591

And you know what?

592

It's actually so much easier with kids.

593

I mean, you have to translate it.

594

You spend a lot of time before I

did that, studying child development

595

and how to frame it for them.

596

But once you frame it correctly for

them, it's so much easier for kids

597

to answer that than it is for adults.

598

'cause adults, we have all

these shoulds piled up.

599

Mm-hmm.

600

And kids don't.

601

Kids know what's important to them.

602

So I worked with these kids and they

like wrote out their core values, their

603

manifesto for life, their vision for what

impact they wanted to have in the world.

604

They created visual representations of it.

605

It was.

606

So heart filling to see.

607

So no, those kids are

gonna start out that way.

608

I love that.

609

I know someone who used to, I teach at

a college in Brooklyn and one person

610

who I know used to do a class there

used to teach a seminar on finding

611

your purpose, but they stopped it

and I wish they would've continued.

612

Maricella Herrera: To do that.

613

I don't know.

614

I feel like there's something, what you're

saying is so important, and I see it in

615

my students, like 17, 18-year-old students

who, what I teach, which is designed

616

thinking, is it I, they're already

starting to make, to bring the shoulds

617

and in my class we do a lot of creativity.

618

So it's about just being

more open to uncertainty.

619

I think something like

this is so valuable.

620

Like I wish I had that when I was younger.

621

Me too.

622

Yeah, yeah, yeah.

623

I'm a huge fan of book learning and

I loved school and all the, I love

624

learning all the things we do in school,

but why don't we have this in school?

625

Like starting at grade school,

honestly, and it just thinking today

626

about technology and that article,

millions of views about how AI is.

627

Alana Winter: Than we think

and it's been a whole thing.

628

These are the things that we're

gonna need, like even more, right?

629

Some of the skills that we are teaching

need to completely change into something

630

that's more fundamental, so to speak.

631

Yeah, absolutely.

632

Okay.

633

Now tell me how you went

through that process of finding.

634

I wanna say finding yourself a little bit,

like finding what it was that was gonna

635

move you again to do something great.

636

Yeah.

637

Three year process.

638

It's never short.

639

Well, you know, I had no guidance, so I

was trying to figure it out all by myself.

640

I was at a conference and I

walked into a workshop on your

641

core values and life purpose and.

642

I was like, okay, cool.

643

Maybe this will help me.

644

And one of the first things they

did was they gave us a sheet of

645

paper and it had hundreds of values

on it, and the instructions were,

646

okay, you've got three minutes.

647

Go through this list and circle,

circle the values and figure out

648

what your top three values are.

649

I've done that.

650

Yes, I've seen that.

651

Yes.

652

I'm sorry.

653

That's a ridiculous approach.

654

It just really, it really is.

655

And I understand a lot of people use

that approach, but it's ridiculous.

656

And I realized as I was doing

it, I realized two things.

657

One, this is really important.

658

Two, this is a terrible approach

to it because as I looked at that

659

sheet, I remember I circled 35.

660

Core values, and I knew even some of

the ones that I was circling were things

661

that like, ah, I know this sounds good.

662

Mm-hmm This is something I

should value, but I didn't have

663

any way of differentiating.

664

And so when the instructor came over

and he looked at me, he is like,

665

uh, you can't have 35 core values.

666

You gotta get it down to like six.

667

And I was like, how?

668

And he looked at me, he goes, I dunno.

669

Very helpful.

670

Thanks.

671

So I sat through the rest of that

workshop, but I, but it really.

672

It landed with me.

673

So I got home and I got big sheets

of flip chart paper, and I wrote

674

those 35 words out there, and

I had these all over my walls.

675

And I would sit and I would stare at

them and I would go, okay, well what

676

are, how do I group them together?

677

Like what are some of the

things that are similar?

678

Mm-hmm.

679

And so I kept doing that and sort

of trying to put them into baskets.

680

And then I'd start asking myself, what is

something that leads to something else?

681

What is something that I want

because it gets me something else.

682

So I had all this and I'm doing this.

683

I've got sticky notes.

684

I'm moving all over the place.

685

Simon Sinek is a friend of mine.

686

Simon came over and.

687

As a favor, I'd gotten, I got

Simon, his first paid speaking

688

gig, so Simon did me a favor and he

came over to spend a day with me.

689

Talk about someone to

help you find, right?

690

Yeah.

691

Yeah.

692

So we're like, okay, great.

693

Cool.

694

I'll find my personal why.

695

So, you know, we're, we're

chatting all day and at the end

696

of the day, Simon goes, okay.

697

Got it.

698

Your personal why is fun

learning and sharing, learning

699

and fun with others and like.

700

That sounds, sounds like me.

701

For sure.

702

That's super cool.

703

I was like, so what do I do with that?

704

And he goes, oh, that's

above my pay grade.

705

It's like, great, okay.

706

I've got my why.

707

And I figured that and I knew,

okay, that's different from values.

708

Yeah, I was gonna point that out

because I think, and you said two

709

things that caught my attention.

710

One is finding what do you want

that brings you to something else.

711

And I was gonna ask if you meant like

values, what that meant, but now.

712

They do sound fun, I think could be

a value, but they, and learning too.

713

But they're a why and

values are not necessarily.

714

Exactly the same.

715

Exactly.

716

Right.

717

Right.

718

The why, that had to be how I showed up.

719

That had to be manifesting.

720

But to give you an to, to clarify

actually what I said about how

721

one things lead to another.

722

So for instance, I had one

bucket that had travel.

723

And it had learning and it had growth

and a bunch of other things in there.

724

And I would look at all of those things

and I knew for me, and again, people

725

will have different buckets because

words mean different things to people.

726

Mm-hmm.

727

So for me, those things, I knew

those things were related and I'd

728

be like, okay, well what do I,

what is it about travel that I get?

729

What is it about learning that I get.

730

I wound up refining all of those things

to one core value of wisdom because all

731

of those things for me led to wisdom.

732

That makes sense.

733

So that's, that was part of the process.

734

So I kept doing that and

refining those things down.

735

My three core values are connection.

736

Wisdom and grace, and so connection,

friends fall into that, family, falls

737

into that community, falls into that.

738

Relationships of every form

fall into that wisdom, learning,

739

travel, growth, adventure.

740

All of those things fall into wisdom

for me, grace, kindness, empathy,

741

all of those things and many

others all fall into that for me.

742

So what I realized after I did

that was, okay, anything that I

743

do, I separate values from needs.

744

Needs are what I need to receive.

745

Values are what I uniquely am

here to manifest in the world.

746

My gift to the world.

747

So anything that I choose to do,

any project that I choose to do

748

has to go through that filter of my

values, that it has to manifest and

749

magnify those things in the world.

750

It has to spread connection, wisdom,

spread connection, et cetera.

751

And I do it incorporating fun and

my, all my learning that I love to

752

do, and sharing that with others.

753

That's how I do it.

754

How?

755

Interesting that the why is

the how, again words, right?

756

Mm-hmm.

757

Yeah.

758

But to just help me clarify something

about myself right now with this small

759

conversation that I never thought about.

760

'cause I do think it's very

common that we mix those two up.

761

Mm.

762

And I do think, as I'm hearing

you, how important those two

763

filters being separate are, Hmm.

764

Maricella Herrera: Note to self.

765

I need to get a little clearer on that.

766

Beautiful.

767

But it took you three years to get

through this process of really, I think

768

one is A, is finding that, but also

two is really adapt, adopting it, so to

769

speak, like really showing up with it.

770

I think that.

771

The process that I went through, there's,

look, there are tons of processes that

772

are out there that are quick hacks.

773

Alana Winter: Figure out your

life's purpose in 15 minutes.

774

I see ads for this kind

of stuff all the time.

775

That sounds to me a lot like

the list of values though.

776

Yeah, totally.

777

And when people do that, they're

not tapping into their true

778

core how many times individuals

and work with companies times.

779

I'll have a conversation with the

CEO, ask about the core values of the

780

company and they'll say, oh, yeah,

yeah, yeah, we did that work already.

781

I'm like, great.

782

What are they?

783

And they'll say, usually

they'll say, oh, integrity.

784

Uh, and, um, uh, uh, and I know

there are a couple of others.

785

I don't remember that

there're on a piece of paper.

786

I, you know, the thing is, if

you tap into true core values,

787

you'll never forget them.

788

They won't, you'll never have to

go look for that piece of paper.

789

It's, it like lands on you deeply in

your body and that's your North Star.

790

Like it's not hard to figure

out from there if you actually

791

get it right, it's there.

792

Do you have any advice on how.

793

People can even just start

through that process.

794

Yeah, yeah, yeah.

795

The values based leadership

is a real core of what I do.

796

Values based and self-awareness.

797

And of course the two are tied together

because you have to be self-aware

798

to know what your values are.

799

But look, I would suggest if

somebody's trying to work through

800

on their own, start with that.

801

If you have nothing else, start with

that list, but just really be aware

802

of what am I picking that's on there

because it sounds good, because it's

803

a should versus what's true to me.

804

Make that list and then ask

yourself questions like,

805

well, what are the shoulds?

806

What did I learn from my parents from the.

807

Social setting that I grew up in,

what were the influences on me and

808

what did those influences put in?

809

That should be my values.

810

And then sit with that list and sit with

how much of that actually is true to me.

811

Ask yourself the question, what makes

me happy when I see it in the world?

812

What do I believe deeply in my heart?

813

Makes the world a better place.

814

What do I believe deeply in my heart

causes pain in the world, right?

815

Sometimes even doing that,

like setting what those are,

816

like the anti values, right?

817

Sometimes that gives you clarity.

818

Look at how you spend your time, right?

819

With your time and your money, that

whatever actually you have that are

820

all stuff we have to do, but your free

time, your free resources, whatever they

821

are, how do you spend those resources?

822

Ask people that are close to you if

you, without knowing anything at all,

823

if you were to say, what do you think?

824

What do you think I

value most in the world?

825

What would you say?

826

Maricella Herrera: What about any advice?

827

Because we're talking about

values and I you, there's three

828

buckets that you said, right?

829

Needs and values, which are different.

830

Needs, what you need, values, what you

put out in the world, and then the why.

831

How do you.

832

Make that happen, or

like how do you show up?

833

Any advice on how to

think of that third one?

834

I feel like needs are of the three,

maybe the easiest, but I'm not sure.

835

Yeah, and, and a lot of times

people conflate needs and values.

836

Mm-hmm.

837

So figuring that out, I really like that

distinction by the way that you make Yeah.

838

Between those two in terms of the.

839

How you, because like even, even

knowing what my core values are,

840

there's no job description for that.

841

Alana Winter: Yeah.

842

But in terms of the how matters a lot less

than the what and the why because once

843

you know what, you are there to magnify.

844

It doesn't matter how you do it.

845

I share with people a story

and it's, I get choked up.

846

I have told this story

probably hundreds of times.

847

I still get choked up every time

I, aw, so I remember there's a, the

848

Beacon Theater in New York City.

849

I used to go see a lot

of live shows there.

850

And down the steps.

851

There was the ladies' room and there

was a woman who was the washroom

852

attendant, and she just stood there

and she gave people a hand how?

853

As they washed their hands.

854

If you stood outside.

855

Of the bathroom.

856

You watch women walk in.

857

You watched women walk out.

858

It was like a different woman walked

out than walked in because the woman

859

that walked out all had a smile in

the spring in their step because that

860

bathroom attendant, every time she

handed someone a paper, I'll cry.

861

It's crazy, I'll cry.

862

Every time she handed someone a paper

towel, she made a point of giving a

863

personalized compliment to that woman.

864

It was not, oh, you look beautiful, right?

865

It was.

866

That dress is so complimentary,

it makes your eyes sparkle, or

867

you have the warmest smile, right?

868

Shani gave these women a

personalized compliment that made

869

them feel so good about themselves.

870

That woman was living her values.

871

She did not as a little girl dream

of being a bathroom attendant.

872

But where she stood, she chose to

make a difference in the world.

873

So the how you do it when you

know what you're here to magnify.

874

The how is less important.

875

Oh, I like that it's.

876

I think I've seen her actually,

that describes very well

877

what you're trying to say.

878

Like what you're saying about the how

which, and I think we sometimes get

879

really, or I, I should say, me get

really focused on that, okay, these

880

are the things that I believe is what

I'm here I wanna put out in the world,

881

or I wanna make an impact in a way.

882

Maricella Herrera: But always that how.

883

The lenses with which I've been

conditioned, I would say, to

884

look at them is still very rigid.

885

And what you're saying really

is, it doesn't have to be, it's

886

just about bringing it out when

whatever it is that you're doing.

887

Mm-hmm.

888

So how did finding these things,

how did that change the trajectory

889

of what you were saying?

890

Alana Winter: You didn't wanna show

up to these meetings because you,

891

the how, what are, what do you do?

892

Question, which I felt that very much.

893

Like how did this clarity

change how you were showing up?

894

I think it, it has this impact of.

895

It, it just makes you

feel very grounded, right?

896

It like lands.

897

When you do this work, it lands

so deeply on you that, you know,

898

I went from feeling, I said

lost in the desert to feeling.

899

Grounded and feeling on solid ground.

900

And what's interesting is that

position that I was in, people then

901

started asking me, I think people just

started noticing and people started

902

asking me about what I'd been doing.

903

And that's eventually how I

started doing the kind of coaching

904

and facilitation work that I do.

905

I was lucky, I was part of a, an

entrepreneur's organization and I

906

started doing some facilitation.

907

For that organization and started

traveling the world and getting to work

908

with leaders all over the world who

then started to ask me to coach them

909

individually to work with their leadership

teams, as I mentioned, in some instances,

910

to work with their families, and it was

it's work that I absolutely love doing and

911

feel so honored every time somebody trusts

me to be able to guide them on this.

912

And also I get to see the impact, right?

913

I get to see the impact of people

who then step into who they truly

914

are, and it changes everything.

915

It changes their leadership when, if it's

the CEO of a company who steps into this.

916

The whole company changes.

917

I've literally had employees in a

company call me and say, thank you.

918

I know you worked with our CEO, because

all of a sudden their values become

919

manifest throughout the organization

and the way the organization operates

920

completely changes as people get aligned.

921

And sometimes there may be people

who are not aligned, they will fall

922

off and everybody else is aligned.

923

All of the friction drops away and.

924

Companies bloom, individuals bloom,

and then this is, I think this

925

is how we have a ripple impact.

926

Mm-hmm.

927

On the world.

928

I love that seems like

meaning met opportunity.

929

Mm-hmm.

930

Mm-hmm.

931

I think actually also when meaning

manifests, opportunity opens up.

932

Ooh, that's even better.

933

Yeah, that's even better.

934

I guess you start seeing.

935

The opportunities that maybe

you wouldn't have once.

936

You're so grounded in that part.

937

Yeah.

938

Yeah.

939

And opportunities maybe

are just attracted, right?

940

Mm-hmm.

941

When there's a strong grounding,

opportunities come in.

942

Yeah.

943

Well, we're almost outta time, so

I'm gonna ask you my last question.

944

If you could go back and

talk to Alana, back when you

945

were wandering in the desert.

946

You were feeling like that,

what would you tell yourself?

947

Reassurance that there is a way,

for sure, reassurance that there

948

is a way everybody finds their way.

949

Nobody stays in the desert forever.

950

It feels like it at the time.

951

It feels like, oh my God, I

am never getting out of this.

952

But take a breath and yeah, take a breath

and enjoy that space for whatever it is.

953

It's a powerful space to be in.

954

That space in between is a very,

very powerful space to be in.

955

It feels like the world is falling

apart and perhaps it's an overused

956

cliche, but it is so true, right?

957

It's that caterpillar that crawls into

the shell and completely dissolves into

958

goo, and you're in that stage where you

are goo and it will, you will reform.

959

And come out as the butterfly.

960

It's so hard.

961

I've been thinking a lot about this.

962

I actually wrote a, an article recently

about it, but sometimes I feel, for

963

me, this is my own experience that I've

gotten stuck in the go face, so to speak.

964

That there's a point where for some

reason you might get, the way I framed

965

it for myself is like, I've gotten.

966

Maricella Herrera: I left my

identity of what I had at work.

967

But now I've sort of latched onto

this identity of being in this

968

liminal space versus moving on

to what I should really be doing.

969

Well, I dunno, look in this liminal

space, what you're doing right now,

970

for example, in creating this podcast.

971

Is you are acting as a goo guide.

972

Alana Winter: I love that.

973

Yeah, I appreciate that.

974

Thank you so much.

975

Thank you for taking the time.

976

Yeah, thank you.

977

It is totally a delight.

978

Maricella Herrera: That's it for today.

979

Thanks for listening.

980

If you like this episode, hit follow or

subscribe so you don't miss the next one.

981

And if it made you think, feel

something or yell, same out loud.

982

Leave a quick rating or review.

983

It really helps.

984

If you didn't like it, just

pretend this never happened.

985

You can also subscribe on

Substack for updates and extras.

986

I'd love to hear from you.

987

Come say hi on Instagram at

Quit my jobb pod, or email me

988

at Quit my job pod@gmail.com.

989

See you next time.