WEBVTT - Finding Our Perfect Match

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<v Speaker 1>It's hard to write a good profile because you have

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<v Speaker 1>to really examine these tiny nuances like you don't have

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<v Speaker 1>much space, but that means you have to have a

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<v Speaker 1>really tight message, like who am I from the perspective

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<v Speaker 1>of someone that I would want to like me.

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<v Speaker 2>Welcome back to On the Job Today, we're speaking with

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<v Speaker 2>Grace Lee, a professional dating coach based in New York City.

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<v Speaker 1>My business is called a Good First Date, and we

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<v Speaker 1>started in twenty eighteen, and I work with men and

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<v Speaker 1>women of all ages and situations on every aspect of dating,

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<v Speaker 1>with my primary focus being online dating, how to optimize

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<v Speaker 1>that your dating apps and everything that comes after that.

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<v Speaker 2>Now, before you go thinking we've changed the format over

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<v Speaker 2>here and On the Job, Grace and I are talking

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<v Speaker 2>about much more than just dating on today's episode. Beyond

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<v Speaker 2>learning what it means to be a professional dating coach,

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<v Speaker 2>we'll uncover the surprising similarities between our romantic and professional lives.

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<v Speaker 2>So even if you're happily hitched or dead set on

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<v Speaker 2>staying single, stick around to get some valuable advice from

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<v Speaker 2>this dating pro Being a dating coach was not something

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<v Speaker 2>Grace Lee set out to do.

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<v Speaker 1>I actually started working in corporate banking, and then when

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<v Speaker 1>my daughter turned one, I left the bank completely. I

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<v Speaker 1>opened a boutique in Shanghai, and then I sold children's things.

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<v Speaker 1>It was really that great thing that happens when you

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<v Speaker 1>are obsessed and love something and then suddenly it's your

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<v Speaker 1>job and you get to do it all the time.

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<v Speaker 2>On paper, everything was going well for Grace. She had

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<v Speaker 2>a diploma from a good school, a successful career, a husband, kids,

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<v Speaker 2>all the pillars of a thriving life. But in two thousand,

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<v Speaker 2>in a nine, Grace's life took an unexpected turn with

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<v Speaker 2>a divorce and a move to New York City. And

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<v Speaker 2>that transition period was as challenging as you'd imagine.

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<v Speaker 1>I got married when I was twenty six, and before

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<v Speaker 1>then was pretty much a serial monogamous, so I had

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<v Speaker 1>never really dated. And since I got married kind of young,

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<v Speaker 1>I'd never had that experience of just being single and

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<v Speaker 1>living that single person's life.

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<v Speaker 2>But now there she was, thrust into a big, new

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<v Speaker 2>city and this unfamiliar phase of life.

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<v Speaker 1>I remember the first date I went on after I

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<v Speaker 1>got separated. Couldn't believe how intense it was emotionally. It

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<v Speaker 1>was like the whole, like the whole box of crayons,

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<v Speaker 1>like every single emotion, from being completely obsessed and fixated

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<v Speaker 1>to feeling like totally tragic, like nothing ever good will

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<v Speaker 1>ever happen to me again.

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<v Speaker 2>In time, though, the intensity of those emotions settled down

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<v Speaker 2>and Grace started doing enjoy the process of going on dates.

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<v Speaker 2>They offered her a healthy relief from the shakeup of

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<v Speaker 2>the divorce and then responsibilities of single parenting.

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<v Speaker 1>So when I moved to New York City, I had

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<v Speaker 1>two little kids and mash dot com was just starting

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<v Speaker 1>to get fired up, so I took the opportunity, was

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<v Speaker 1>really curious and leaned heavily on match and just started

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<v Speaker 1>dating a ton.

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<v Speaker 2>Dates were also a great way for Grace to explore

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<v Speaker 2>her new hometown and engage with people she'd never have

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<v Speaker 2>met in the finance world.

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<v Speaker 1>Being a parent, like having little kids, and also I

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<v Speaker 1>was working in banking at the time, so that was

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<v Speaker 1>my circle. And then suddenly with online dating, I could

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<v Speaker 1>match someone from a completely different world, and I loved

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<v Speaker 1>I loved the experience of just sitting down with someone

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<v Speaker 1>and imagining myself in their childhood and what they did.

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<v Speaker 1>It's kind of how also how I discovered different parts

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<v Speaker 1>of the city, and it just really opened my mind

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<v Speaker 1>to life outside of being a banker and having little.

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<v Speaker 2>Kids were once the idea of having to go out

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<v Speaker 2>into the dating world seemed overwhelming and intimidating. Soon Grace

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<v Speaker 2>couldn't wait for her next date.

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<v Speaker 1>I think because I was fresh out of a divorce

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<v Speaker 1>and I didn't have any experience. I really went in

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<v Speaker 1>full force and dated many, many people. You know, I

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<v Speaker 1>was one of these people that might have gone on

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<v Speaker 1>three or four dates a week.

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<v Speaker 2>And being the organized professional type, Grace even made a

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<v Speaker 2>spreadsheet to keep track of her potential suitors. Do you

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<v Speaker 2>remember what some of those columns might have looked like?

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<v Speaker 1>Sure, I mean there were basic ones, you know, age,

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<v Speaker 1>I profession, something about it was fun to talk to them,

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<v Speaker 1>might have been like a personality score, what they did

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<v Speaker 1>for work, how much money they had, what neighborhood they

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<v Speaker 1>lived in. I'm not proud to admit that, but that

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<v Speaker 1>was definitely on the spreadsheet, just like it is in

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<v Speaker 1>a database for any matchmaking service. And there's probably an

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<v Speaker 1>attractiveness rating that fell outside of age and height, just

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<v Speaker 1>if I was attracting them or not.

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<v Speaker 2>And while Grace was doing fine on match dot com,

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<v Speaker 2>She also put her name on one of those professional

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<v Speaker 2>matchmaking databases and shortly thereafter gets invited in to fill

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<v Speaker 2>out a questionnaire.

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<v Speaker 1>They were asking me all kinds of questions and doing

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<v Speaker 1>it in a very serious way, like why are you

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<v Speaker 1>still single? What are you looking for? It was on

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<v Speaker 1>your red flag list? All of these questions that are

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<v Speaker 1>actually so fun to answer, and all of this information

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<v Speaker 1>is there to help them match people well.

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<v Speaker 2>And Grace found this whole process fascinating.

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<v Speaker 1>So I remember during that interview looking at her and

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<v Speaker 1>asking her if this was a real job, because I

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<v Speaker 1>couldn't believe that this was someone's profession. And long story short,

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<v Speaker 1>I was never match with that client, but I ended

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<v Speaker 1>up working as a matchmaker.

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<v Speaker 2>And initially Grace loved matchmaking, especially compared to banking.

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<v Speaker 1>Speaking about the differences between matchmaking and working in Kaindance.

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<v Speaker 1>The Monday morning meeting for matchmaking is hilarious. It's a

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<v Speaker 1>bunch of matchmakers talking about their clients, talking about people

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<v Speaker 1>in the database. Do you think that this person would

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<v Speaker 1>go all with this person? So it was like getting

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<v Speaker 1>paid to gossip, but of course in a very professional,

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<v Speaker 1>purposeful way.

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<v Speaker 2>But while Grace really enjoyed meeting her clients and helping

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<v Speaker 2>them in their romantic journey. She found the particulars of

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<v Speaker 2>matchmaking less than ideal. Well, not to mention, from her

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<v Speaker 2>own dating experience, she knew that the dating apps, which

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<v Speaker 2>were really gaining in popularity at this time, did a

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<v Speaker 2>pretty good job of connecting people. That is, if you

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<v Speaker 2>knew how to make an effective profile.

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<v Speaker 1>I realized, like, I can help people get on a

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<v Speaker 1>good first I'm very, very good at getting people on

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<v Speaker 1>a good first date.

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<v Speaker 2>So that's when Grace pivoted from being a professional matchmaker

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<v Speaker 2>to a professional dating coach.

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<v Speaker 1>There's a lot of work that goes into helping clients

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<v Speaker 1>come up with their profile. It's intensely creative personal work.

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<v Speaker 1>So it's really a matter of figuring out how to

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<v Speaker 1>help people make their profile more like them, to be

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<v Speaker 1>a better representation of them, and then also to teach

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<v Speaker 1>them how to swipe and text so that they can

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<v Speaker 1>filter people out and go on the days that they

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<v Speaker 1>want to go on.

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<v Speaker 2>To do this, Grace meets with her clients one on

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<v Speaker 2>one and tries to get to the core of who

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<v Speaker 2>they are.

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<v Speaker 1>I'm always scanning for those things that are going to

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<v Speaker 1>make them stand out because they're in a pile of

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<v Speaker 1>thousands of people and they have a moment to make

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<v Speaker 1>an impression, and then how do you present that. It's tricky.

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<v Speaker 2>And while it might be tricky to boil someone down

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<v Speaker 2>to a limited amount of text and a few pictures,

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<v Speaker 2>when it does happen, Grace will tell you it feels

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<v Speaker 2>better than banking. Ever. Did I love it?

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<v Speaker 1>When we come out on the other end and we

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<v Speaker 1>have it. When we nail the thing, it's like, Oh,

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<v Speaker 1>feels so good, like we got it. Then the person

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<v Speaker 1>forget the date, they're looking at the profile and they're like, Wow,

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<v Speaker 1>I'm actually a pretty interesting person.

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<v Speaker 2>In this way, Grace is helping people take stock of

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<v Speaker 2>their lives to highlight what makes them unique, capturing their personality,

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<v Speaker 2>and celebrating their achievements, and then to present all that

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<v Speaker 2>to the world with the hope of catching someone's attention,

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<v Speaker 2>which sounds pretty similar to sending out resumes and cover letters,

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<v Speaker 2>doesn't it. So when we come back from the break,

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<v Speaker 2>we'll explore the many parallels between online dating and our

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<v Speaker 2>increasingly digital business world, and maybe we'll get Grace Lee

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<v Speaker 2>to help us present our best selves, whether that's to

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<v Speaker 2>a potential partner or our next employer.

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<v Speaker 3>Looking for a job is lonely, endless searching, phone calls

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<v Speaker 3>that go nowhere, applications that vanish into thin air. What

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<v Speaker 3>if you could link with dozens of local companies who

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<v Speaker 3>endless opportunities and no fees ever for job seekers Express

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<v Speaker 3>Employment Professionals expresspros dot com.

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<v Speaker 2>We're back with professional dating coach Grace Lee. Through her

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<v Speaker 2>service A Good First Date, Grace helps people put their

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<v Speaker 2>best foot forward on dating apps and other online dating platforms.

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<v Speaker 2>But it's not just our love lives that have gone digital.

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<v Speaker 2>Job applications are submitted online, meetings happen over zoom, and

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<v Speaker 2>most of our work communication these days runs through email

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<v Speaker 2>or Slack. These shifts have revolutionized how we work, but

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<v Speaker 2>they've also introduced some challenges, because anytime we translate ourselves

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<v Speaker 2>into a digital format, there's a risk that something gets

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<v Speaker 2>lost in translation, and that risk starts with our most

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<v Speaker 2>essential documents.

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<v Speaker 1>I think in a CV it's a little bit less esoteric.

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<v Speaker 1>There is more standard ways of presenting yourself, so it's

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<v Speaker 1>like kind of have to figure out those key things

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<v Speaker 1>about yourself, how do you want to talk about them?

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<v Speaker 1>And if you can take your ego out of it,

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<v Speaker 1>you can start to think more carefully about how you're

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<v Speaker 1>presenting yourself.

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<v Speaker 2>As you all learned in a previous episode this season,

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<v Speaker 2>a lot of our online job applications are first reviewed

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<v Speaker 2>by AI, so yes, you need to have all the

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<v Speaker 2>pertinent information in there, but eventually, hopefully your CV will

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<v Speaker 2>reach human eyes. And just like with a dating profile,

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<v Speaker 2>you want your CV and cover letter to catch that

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<v Speaker 2>person's attention with clear and gauging messaging.

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<v Speaker 1>So just thinking about, Okay, the other person is sitting

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<v Speaker 1>there with your CV, they have a checklist of things

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<v Speaker 1>that they're trying to tick off to move you to

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<v Speaker 1>the next round. They're not invested in whether or not

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<v Speaker 1>you get.

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<v Speaker 2>The job or not.

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<v Speaker 1>They kind of want you to because they don't want

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<v Speaker 1>to keep doing this thing. They just want to find

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<v Speaker 1>the person already.

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<v Speaker 2>And while it might be tempting to make one resume

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<v Speaker 2>and send it out to every job, Grace recommends customizing

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<v Speaker 2>your messaging to the job you're seeking.

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<v Speaker 1>In that case, it's going to be about highlighting what

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<v Speaker 1>was interesting about your job. So if you're going into

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<v Speaker 1>the hospitality industry, that job that you had over the

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<v Speaker 1>summer serving coffee is actually going to be more relevant

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<v Speaker 1>than your private equity job.

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<v Speaker 2>And this isn't a send it and forget it sort

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<v Speaker 2>of thing either. Just as Grace made a spreadsheet to

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<v Speaker 2>keep track of our dates, as job applicants, we need

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<v Speaker 2>to reflect on the responses our applications get. We need

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<v Speaker 2>to ask ourselves what's working, what isn't, and then fine

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<v Speaker 2>tune our messaging based on that feedback.

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<v Speaker 1>Yeah, it's like I can't believe I didn't get invited

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<v Speaker 1>to any first round interviews for banking. I can't believe it,

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<v Speaker 1>and then just being curious about it, like, oh, I

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<v Speaker 1>wonder why not. Maybe there's a good reason.

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<v Speaker 2>Eventually, though, if you get through those early rounds, you'll

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<v Speaker 2>be asked in for an interview, and Grace says interviews

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<v Speaker 2>bear an uncanny resemblance to a first date, despite the formalities.

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<v Speaker 2>It's just two people trying to get to know one another.

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<v Speaker 1>So for every single thing you have on your CV,

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<v Speaker 1>have a story, and that story should be about how

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<v Speaker 1>what you did makes you qualify for this job, and

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<v Speaker 1>that story should just be interesting and fun, one that

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<v Speaker 1>you enjoy telling, so that you have a good conversation.

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<v Speaker 2>So in the same way you might highlight your love

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<v Speaker 2>of live music on your dating profile. Grace suggests coming

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<v Speaker 2>into the interview with a strategy to move the conversation

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<v Speaker 2>in a purposeful direction.

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<v Speaker 1>Let's say you're going to an interview and you really

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<v Speaker 1>want to learn about AI. That's something that you want

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<v Speaker 1>to do in your career. So you want the conversation

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<v Speaker 1>on the interview to touch AI at some point, and

0:13:10.800 --> 0:13:12.920
<v Speaker 1>you want it to be pretty central, so that you

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<v Speaker 1>can talk about the things that you've done on your

0:13:15.040 --> 0:13:20.040
<v Speaker 1>own and you can analogize how those skills might help

0:13:20.080 --> 0:13:23.080
<v Speaker 1>a company like theirs. Even if the job that they're

0:13:23.240 --> 0:13:26.400
<v Speaker 1>trying to interview you for may not be an exact fit.

0:13:27.120 --> 0:13:29.720
<v Speaker 1>Now they've seen you and they said, oh, this person

0:13:30.080 --> 0:13:33.000
<v Speaker 1>is really interesting and they've brought all this experience in AI.

0:13:33.160 --> 0:13:36.079
<v Speaker 1>So even if my department isn't looking for it, maybe

0:13:36.080 --> 0:13:37.800
<v Speaker 1>this is a candidate that would be good for this

0:13:38.080 --> 0:13:38.880
<v Speaker 1>other department.

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<v Speaker 2>And we should also remember that the interview is a

0:13:42.400 --> 0:13:43.280
<v Speaker 2>two way street.

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<v Speaker 1>You can show them that you're interested in a lot

0:13:46.360 --> 0:13:49.880
<v Speaker 1>of ways by being attentive by being interested in their story,

0:13:50.320 --> 0:13:53.480
<v Speaker 1>by sharing things about yourself that you want them to know,

0:13:54.360 --> 0:13:56.880
<v Speaker 1>and then you have to let them meet you half

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<v Speaker 1>way too. I would try to touch on a lot

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<v Speaker 1>of different topic until I found the one that I

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<v Speaker 1>thought they were comfortable with. Then they can bring themselves

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<v Speaker 1>out and that's when you can test real compatibility.

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<v Speaker 2>That same advice still applies after you get the job,

0:14:12.520 --> 0:14:15.160
<v Speaker 2>or even if you've had the same job for decades,

0:14:15.640 --> 0:14:17.600
<v Speaker 2>because at the end of the day, no matter what

0:14:17.640 --> 0:14:20.240
<v Speaker 2>we do for work or how long we've been doing it,

0:14:20.760 --> 0:14:26.640
<v Speaker 2>our professional lives revolve around interpersonal relationships. As Warren Buffett said,

0:14:26.800 --> 0:14:30.960
<v Speaker 2>partnership is not a legal contract between two equal individuals.

0:14:31.360 --> 0:14:35.240
<v Speaker 2>It's an emotional alliance between two people who are committed

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<v Speaker 2>to each other's success.

0:14:37.320 --> 0:14:41.720
<v Speaker 1>The number one thing you need in any situation, job, romance,

0:14:41.840 --> 0:14:45.840
<v Speaker 1>friendships is mutual interest. And when we don't have that,

0:14:45.880 --> 0:14:47.320
<v Speaker 1>things like point fall apart.

0:14:48.280 --> 0:14:52.080
<v Speaker 2>And speaking of falling apart, since we're talking about relationships

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<v Speaker 2>of all sorts here, it'd be wrong not to acknowledge

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<v Speaker 2>that sometimes they break down, that our passions wane, or

0:14:59.120 --> 0:15:02.480
<v Speaker 2>a job just run its course. That isn't to say

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<v Speaker 2>we should all be quick to jump ship and run

0:15:05.080 --> 0:15:09.720
<v Speaker 2>to the next new thing. Lasting rewarding relationships take work

0:15:09.880 --> 0:15:14.360
<v Speaker 2>and commitment, but if that time comes grace. Lee has

0:15:14.440 --> 0:15:18.880
<v Speaker 2>learned from personal experience that sometimes starting a new is

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<v Speaker 2>just what we need.

0:15:20.920 --> 0:15:24.960
<v Speaker 1>I love getting to know my clients, and I love

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<v Speaker 1>watching them have these breakthrough moments where they come to

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<v Speaker 1>me and they're so worried about something, and those moments

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<v Speaker 1>where I can just reassure them that they're doing fine. Yeah.

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<v Speaker 1>I want people to feel good about their lives and

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<v Speaker 1>optimistic about what could happen, and confident that they're doing

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<v Speaker 1>everything they can to find the person they want to

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<v Speaker 1>be with.

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<v Speaker 2>For on the job, I'm Avery Thompson