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Thriving in career transitions with Holly Smevog
30th April 2025 • This Daring Adventure • Trista Guertin
00:00:00 00:24:41

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In this episode, I welcome Holly Smevog, a globally certified career counselor from HMS Career Coaching.

Holly shares her journey into career coaching and offers valuable insights and strategies for individuals, particularly mid-career professionals, seeking to navigate career transitions.

We discuss ageism, transferable skills, and crafting a compelling professional narrative. Holly also details her four-step coaching process, the role of assessments, and how to leverage AI tools like ChatGPT in job searches.

Whether you're looking to make a career change, re-enter the workforce, or find more meaning in your professional life, this episode provides practical advice and encouragement.

Key Moments:

00:37 Meet Special Guest Holly Smevog

01:53 Holly's Journey to Career Coaching

04:08 Challenges Faced by Mid-Career Professionals

07:44 Career Coaching Strategies and Tools

15:17 The Emotional and Mental Aspects of Career Transitions

22:53 Final Thoughts and Contact Information

Connect with Holly:

Career Counseling, Coaching & Planning - Portland Maine - HMS CAREER COACHING

Instagram

🎧 Let’s go.

Connect with Trista:

Join my free Triggered to Transformed: Emotional Tools That Actually Work class - May 6th at 7PM EDT. Register here: https://fabulous-originator-6309.kit.com/aa9986bd6a

Interested in 1:1 coaching? Book your discovery call here and let's talk.

Follow me on Instagram: tristavguertin

Visit my website: www.tristaguertin.com

LinkedIn: Trista Guertin | LinkedIn

Ready to end the people-pleasing? Get my Validation Shift mini-course HERE. USE COUPON CODE TAKE5 to receive $5 off the price.

Please like, share and subscribe this podcast episode and we'll see you next time!

Transcripts

Speaker:

Welcome to This Daring Adventure podcast

where we work on bridging the gap between

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where we are and where we want to be in

order to live a bigger and bolder life.

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In this podcast, we will provide

inspiration, tips, and skills

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you need to make your life the

adventure you want it to be.

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Here's your host, mindset,

mentor, and life coach, Tri

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Trista: Hi everybody.

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Welcome back to This Daring Adventure,

and today I have a special guest.

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I have Holly Smevog.

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Welcome Holly.

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Holly is with HMS Career Coaching.

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She is a globally certified career

counselor and job search coach, and

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she is connecting people with their

best career through counseling,

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coaching and consulting services.

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And she has experience in both

public and private sectors, in

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organizations large and small.

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And Holly has helped hundreds of people

find their vocational sweet spot.

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And I should also mention that

Holly is a former client of mine.

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Welcome Holly.

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Thank you so much for being here today.

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Holly: You're welcome.

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It's my pleasure.

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I'm excited.

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Thank you.

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Trista: Yeah, it's so nice to catch up

with you and I really was excited to have

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you on because as I was saying just before

we started, I do have a number of clients

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who come to me who are looking to change

careers in midlife or who have, lost

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their job or want to make a job change.

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But it's a struggle.

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And once we get into our fifties

and we can dive into to all of that,

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but welcome and why don't you tell

us a little bit more about yourself

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and the coaching that you do.

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Holly: Sure.

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I myself had a circuitous path to

this career of career coaching, which

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I discovered about 10 years ago now.

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But I worked in Silicon Valley for

technology companies and have a long

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career in marketing, research, product

development, and then started to get into.

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Educational technology

and working in schools.

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And that led me to career, to

kind of college counseling.

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And there was one class in my counseling

program, which was on career counseling.

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And most people hated that class.

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And I absolutely loved it.

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And I knew right away that was my thing.

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When can I hang my shingle?

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And I realized that I had been the person.

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That friends and family had been

reaching out to since, adulthood.

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What should I do with my career?

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I have this interview coming

up, what should I say?

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Oh, can you take a look at my resume?

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And it was all of these

experiences coming full circle

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to the place I was meant to be.

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So I started the company in about 2017.

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And in 2020 with the

pandemic we got busier.

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So I've been working with five

coaches on my team and a couple resume

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writers, and we help individuals,

largely mid-career professionals,

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men and women who get to a point.

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Where they've built a career

over a few decades and they just

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feel like it's time for a change.

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Some people have been laid off or lost

their jobs, but other people realize

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that they really want more meaning

out of their career, or that they've

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followed a path of happenstance, fallen

into jobs along the way, and they.

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Kind of wake up one day and

think, how did I get here?

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And I really wanna put more intention

into my career at this moment.

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And I get, friends and family often,

or get tired of hearing you ask

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what should I do with my career?

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Or giving their advice.

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And so people turn to a career

coach to really, get clear direction

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and get back on their feet.

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Trista: Okay.

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I think this is so interesting because

yes I'm seeing this with a lot of women.

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So you're working with both

men and women, correct?

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Holly: That's

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Trista: right.

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Do you see any challenges that

maybe women face different than men?

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Holly: I do see much more a typical

pattern with women of, they followed

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careers that allowed them flexibility

for things like motherhood or, whatever

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their role in a partner in a relationship

was or just less of a typical.

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Corporate path, oftentimes.

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And maybe they're thinking, I don't

know, I've had all these different jobs.

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How do my skills transfer

into something else?

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Or women who are facing divorce,

for instance, who haven't needed

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to bring in a certain salary.

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And now they're at a point

where I, their needs and their

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values have really changed.

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And how does a career, match that?

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How can they solve this problem?

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Trista: Okay.

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And then of course, I think you've

heard it, I've heard it several

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times, we're in our mid to late

fifties, who's going to hire us?

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What are our options?

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And what do you tell people

when they come to you and are

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feeling like they're just not

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employable any longer.

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Or that these challenges exist.

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Holly: Yeah, I think ageism is a thing and

that it's also the worst thing is when,

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we limit ourselves by believing that,

they're not, that you're not gonna find

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a job and the best way to combat it is to

come from a strong candidate perspective.

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So to set yourself up well, and I think

that people even with really varied

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careers up until, middle age don't,

they have so many transferable skills

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that come together in powerful ways.

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And so that's how we work with

people to really figure out what's

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their most powerful message.

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And where and what, starting from a place

of reflecting internally, let's look at

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you and figure out all the things that

you're bringing to the table right now.

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And also what you really want in

your life, what you need, your values

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and synthesize that in a way that

really resonates with someone, and

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then look, okay, now that we can,

now that we have a great message,

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we've articulated your professional

identity in a way that excites you.

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Where in the market is

someone looking to hire you?

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Where is there are you valued out

there and coming once you're standing

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firmly in your own feet in terms

of owning what you're bringing?

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Your potential, it's a lot easier to

convince somebody else that you know,

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that you have something to offer.

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And I think that older workers really

do have a lot to offer because there can

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be, the softer skills can make someone

a really strong leader can train and be

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great role models for younger people.

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So I think there really is a value and

a lot of employers are seeing that.

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So I do see good hiring

rates for older people.

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In many places there is a

workforce shortage in many states.

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For instance, the state that I live in,

there's a lot of people retiring and

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not as many younger people moving in.

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So the market for older

workers is pretty strong.

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Trista: Okay.

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So then Do you do certain assessments

or certain quizzes or certain.

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Trainings with your clients to help them

narrow some of their skills and strengths?

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Holly: Yeah.

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Interests?

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Yeah, since we've been doing this

for a while, we do have a four step

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process essentially, and we've even

developed a course, an online course.

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It has 37 modules that kind of guides

people through career transition, and

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there's a workbook along with that

and some assessments built in, but.

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Typically.

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First phase, we do use assessments.

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We use sort of Myers-Briggs personality

plus the strong interest inventory,

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which has a career focused element.

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And we have use Gallup

StrengthsFinder, which is more

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about like your innate strengths.

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So what are the unique, what is your

secret sauce like that you're born with?

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And we have a values assessment

that we've created that helps people

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figure out their priorities today.

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And assessments are very much an

instrument in the coaching conversation.

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Not a scientific pointer, but that's

the first thing we do is really take a

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look at you and if people are feeling.

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Insecure and worried.

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There's also that emotional component of,

mental fitness and mindset that we address

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to let's get you feeling really strong.

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And then, and that whole process naturally

lends into what I was talking about, where

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you get direction then in the market,

what job titles might you be looking for.

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And then in the third phase.

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It's about strategy.

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So coming up with your own

personalized plan to crack the

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job search or the career pivot.

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And that is a place where we're working

on your resume and your LinkedIn and

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the resume is a really interesting

project because the resume today isn't

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really a list of responsibilities.

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It's more of a story of highlights,

like the things that you're

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most proud of from your career.

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You start to again, gain confidence

and think about how you would be

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talking to someone in a networking

conversation and then an interview.

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So it all builds on itself.

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And once we get the resume linked

in LinkedIn, we put a networking

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plan together and an application

plan and roll out from there.

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Trista: So then how long, typically, I

know maybe this isn't a precise science,

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obviously, but how long does it take

for someone who's switching careers to

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identify or to get a new job, and how long

typically do your clients work with you?

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Holly: Interesting questions.

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The average time for a job search,

so if someone's been laid off for

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in instance, is about five months.

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We

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usually help people get

jobs in about three months.

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So getting career coaching

helps people land jobs faster.

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Our standard program is actually

two months because that is what we

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found is the right amount of time

to get you on your feet, get your

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direction, hone your messaging, and.

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Get you, ready to hit the market.

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And then people are going out on

their own doing some application.

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Maybe they're already interviewing and

negotiating a job offer, but typically

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eight weeks is enough to get direction

and get you going on the job search.

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Trista: And then is there any sort

of follow up support when people

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are continuing to interview?

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Maybe I.

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What happens when people

are in the thick of it?

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Holly: We provide mock interviewing, of

course, as part of our coaching package.

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We also have an interactive interview

app that you, that people can access even

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after they're done coaching at us, which

is coaching with us, which is a very

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helpful service that actually evaluate

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your performance in an interview and

sets up custom interviews for you.

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And people will continue

to reach out to us.

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We're, we think of our coaching

as a partnership, so we're

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boots on the ground with you.

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Even if we have a set number of

sessions, we're texting and emailing

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in between, and we have a private

LinkedIn ask a coach group where people

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can write in any time questions and

have a coach answer their question.

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Trista: Do you use chat GPT at all?

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Would that be helpful for people

to prepare or to, prepare, maybe

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prepare questions, prepare answers,

are you tapping into that at all?

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Holly: Definitely.

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Yeah.

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So I try to steer people away from having

AI actually write things that they're

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submitting, but it's fantastic for

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analyzing a job description and

pulling out keywords for that,

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you would want to actually copy.

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It's important to actually copy the

exact keywords from a job description

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onto your resume to make it through

the applicant tracking systems.

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So that's where AI really helps out.

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Also be before an interview, you

can put in the job description and

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request, you know what would be

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30 minutes of interview questions

from this job description.

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That's super helpful.

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When I am steering people

towards cover letters, I usually

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suggest AI in a more custom way.

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Give me the top three categories of skills

they're really looking for in this job.

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And then you can gear your

cover letter using that.

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But I think AI is a really helpful tool.

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Yeah.

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Trista: Yeah, I was trying to

think the other day whether

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there would be some prompts that

I could create for my clients.

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I was playing around like whether,

if people are feeling stuck

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and maybe coming, I don't know.

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I was just thinking like there's got

to be a way that we could help them

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to, do some exploration maybe, or

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Holly: I think there are some yeah.

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First of all, really interesting questions

that people should ask themselves.

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You can probably imagine these,

but when, when was the last time

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in your career where you really

felt like in your flow and happy?

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What were you doing then?

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And then similarly, like when

you're around people in a

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professional setting, like what's,

what are those interactions like?

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And trying to ask

yourselves those questions.

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But I think that if certain

things about yourself I.

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You can probably use AI to what

are good jobs for someone who,

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prefers to work as an independent

contributor and has, marketing skills.

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I think there are lots

of ways to get ideas.

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I think that's why career coaching

helps though, because you brought up a

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good point is that AI is so huge, the

world of information is so huge and.

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Even before all this technology, people

would come to us and they're like, there's

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just so many ideas running through my head

and I have all the ideas, but I also have

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all the pros and cons of all those ideas

and I just can't make sense of it all.

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And that's what happens when

people dive out into the internet.

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Trista: Okay.

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Do you touch on a career

as a person's identity?

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I've had, I've been asked that a few

times myself and been part of discussions

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where, trying to shift away from that,

and maybe particularly someone's been

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in a position for a number of decades

and that's been their identity.

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And trying to sh obviously if

you're, you've been in one career

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and you're shifting to another,

that could bring up a lot of issues.

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But also just trying to get

away from that, that your career

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doesn't have to be your identity.

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That you're this whole person and

not placing, because I'm seeing,

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people putting so much emphasis or

importance on the career to define

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them and make them who they are.

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So I don't know whether that

comes up at all for you in

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some of the work that you do.

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Holly: It comes up in a

couple different ways.

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I think you're right.

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Sometimes it's helpful

to compartmentalize.

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We get into these patterns and

sometimes the patterns can become

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boring or unsatisfying over time.

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And so it, I see that happening in

people's jobs where they just start

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to feel, more down about their work.

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'cause it's not new and

it's not exciting and.

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They're just not getting

satisfaction from it.

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So some of the things that happen when

I'm talking with people is when we

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look at interests, there's hobby there.

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Some interests can be hobbies, like

things that you do outside of work,

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and in some cases the end result

isn't getting someone a new job.

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But it's how to build those

satisfying activities into your

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life, outside of work hours.

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And another thing that people do

increasingly is have a side hustle.

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So they'll have a job, but they'll, say

I've always been interested in coaching

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or I've al always been interested in.

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Creating toys for kids

or something like that.

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And so they'll start doing it on the

side and they'll feel more fulfilled

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and that will take the pressure off

of work and they'll think, actually,

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I'm not that disappointed with my job.

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Trista: Yes, exactly.

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I think that's really important

because it is a mind shift or a

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mindset shift where yes, the job

is just a circumstance, right?

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And it's not there to make you happy.

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It's not there to fulfill you.

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It's not there to give

you all of these things.

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You want to show up, you want to do

a good job, you want to be valuable.

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And obviously it provides

you with a livelihood.

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But yes, It's not there to give you value.

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It's not there to e even, fulfill

you or to do anything for you

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other than provide that livelihood.

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And I do understand because I

wanted to do rewarding work.

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And now as a coach it's really important.

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But for me there's also been a shift

to challenging myself to keep learning

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and growing, and it doesn't have

to necessarily be career related.

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And as you said, a side hustle

or hobby or whatever it may be.

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It's that opportunity for us to invest

in ourselves or time or energy, our

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resources to keep growing and to see what

our capacity is and what the possibility.

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What possibilities exist for us

out there that can give us energy

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and light us up and give us joy.

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Holly: I think getting back to what

you said at the very beginning about

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people coming to you who are feeling

stuck, I see that a lot and by the

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time they have a conversation with me,

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everything's shrouded in this

things are bad with my career or,

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and it results in a thinking that

they need to make 180 degree shift.

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Everything needs to change.

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And when we pull it apart, shifting one or

two things could make a huge difference.

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Moving to a different department or

even having this conversation with

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your boss or maybe getting a different

job for a different company, but

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still continuing to do what you do.

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Not completely shaking everything up.

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Trista: Because it, it's okay to make

a change, but you really want to be

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conscious of why you're doing that.

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Because if you think it's going to

be better over there than it is here,

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you're going to be disappointed,

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'cause you're going to

take your brain with you.

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You're gonna have the same thinking

patterns, the same habits, right?

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So you can go to that new position, you

can go to that new department and it's

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going to be exciting and it's going to

be different and it's going to be fun

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because our brain loves that novelty.

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It loves something new and different, and

then that novelty is going to wear off.

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And you're going to go back to

those same thought patterns that you

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know, you were facing previously.

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And I see this because people think

they need to change their house, they

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need to change their relationship,

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they need to change, their

cities, whatever it is.

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And I see that, with some of my clients,

like they think if they find this career

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or they find this job in the same way.

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Someone thinks if I find this man

or this relationship, this is what's

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going to make me happy and this

is what's going make me fulfilled.

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And I'm like, no, it doesn't

necessarily work out quite like that.

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Holly: Exactly.

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When you know, and it's like

when you're meeting a coaching

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client at the beginning.

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You're trying to get really clear on what

they're looking for with the outcome.

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You're trying to also

get, what's that feeling?

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What is, not just the result, like

the new relationship or the new

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career, but what are you feeling

about it that makes it so different?

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And then what you're making me

think, which is super helpful,

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is what are the thoughts that you

are going to hold at that moment

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that will make you feel that way.

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And if I, that's a really

powerful concept to Exactly, yes.

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Plan and to that extent.

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Trista: Yeah.

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And so I tell people, you can

make that change, but don't do

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it from a place of scarcity.

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Or hurry.

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And that you think it's

gonna fix everything.

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You can change jobs, you can change

relationships because you want to, right?

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Have your reasons like them.

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But just clean up your thinking

beforehand and know why you're making

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that change and really like your reasons.

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And then be prepared.

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It's not gonna be all rainbows

and daisies over there either.

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It's not necessarily

gonna be more exciting.

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It's not going to necessarily

be more fulfilling.

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But just you need to be aware and

clean up your thinking every day

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when I'm working with my clients,

you need to clean up that thinking.

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No matter what.

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And whether that's creating your own

business or looking for a job or you're

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in a relationship with your partner,

husband, whomever it is, you, it's work.

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It's going to be work.

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So you need to just really be

aware of what you're thinking and.

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It's not going to be any better over there

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Holly: than it's now.

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Yes, exactly.

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Yeah.

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I'm writing that down now.

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Clean up your thinking.

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That's how I'm going to spend my day.

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Trista: Yeah.

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Good.

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All right.

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I.

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I have loved having you on.

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It's been so great to learn more about

your work and to catch up with you again.

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Do you have anything you, any advice

or tips or guidance you want to

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leave people with as we wrap up here?

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Holly: I would just say, alongside

what I was what we were talking about

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before was that everybody has skills

that are valuable in the marketplace

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and sometimes it's hard to see them.

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I.

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So if people who are having trouble,

there's lots of, free resources or

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coaching, but everybody has a place

in the market where someone's needing

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to pay you for your skills today.

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Trista: That's good.

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I like that.

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And I will make sure we have all

of your information and links in

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the show notes, but if you want to

tell people how they can find you.

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Holly: Sure.

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Yes.

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My website is probably a great

place, HMS career coaching.com.

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And we're on Instagram too.

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HMS career coaching.

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Okay.

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Thank you so much for having me on.

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This has been such a pleasure.

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Trista: Thank you, Holly.

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I think it's been really

helpful for everybody.

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And

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thank you

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for your

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time.

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Thank you for listening to

This Daring Adventure podcast

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:

with your host Trista Guertin.

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We hope you enjoyed the tips and

conversations on how to get excited

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about life Again, as always, you

can head to tristaguertin.com

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:

for additional resources and to

book a one-on-one coaching session.

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You can also follow Trista on

Instagram at tristavguertin.

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Don't forget to subscribe, rate

and review us on Apple Podcasts.

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:

Thanks again for tuning in

and we'll see you next time.

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