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Welcome to Milestone Moments, the show where

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we explore the journeys that lead to success.

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I'm Sheila Slick, your host and founder of Five

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Milestones. In every episode, we will bring you

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insights from the minds of entrepreneurs, leaders

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and experts who will share not just their expertise,

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but the milestone moments that have reshaped

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their journeys and led to significant achievements.

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So if you're looking for motivation, you're in

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the right place. Subscribe now and discover the

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milestones that mark the path to success. Welcome

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to another episode. I'm Sheila Slick, your host.

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And today, my special guest is Jake Wysocki.

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Jake has trained hundreds in workshop facilitations

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at Fortune 200 companies, and then he left to

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bring that same methodology to the world of coaching.

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He now runs IntentionCraft, where he builds five

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-star group coaching programs for established

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experts. Welcome to the show, Jake. Thanks for

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having me, Sheila. Great to be here. Well, I

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normally love to start learning about why you

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started Intention Craft. What was that moment,

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that pivotal moment that led you to do what you're

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doing today? Yeah. So for me, the biggest moment

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that really led to that was probably the most

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like salient moment was a conversation with my

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wife. So I've been talking in general terms for

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a few years. I really loved my job. We can get

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into that if it's relevant before I quit. But

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I've been talking about I'll do my own thing

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at some point. And she. Asked me one summer,

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I think it was 2023. We were just, we both were

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from home and I was popped upstairs to chat with

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her about something. She said, so when are you

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going to do that? I said, oh, I don't know. Sometime

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in the next few years, the same standard answer.

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And thankfully she pressed me on it. She said,

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okay, you've been saying that for a few years.

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So are you just going to keep saying that for

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a few years or are you actually going to do something

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about it? I said, well, why aren't, why not now?

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like why not just do that like this year i said

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well i don't know money i love my job i don't

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really want to change she's like okay are those

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real reasons like go check the money thing that's

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not the real reason like we can live off of my

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salary for now and you can figure it out that

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was the that was the case and it ultimately we

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determined there is no reason not to do it now

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so that's when i gave my three months notice

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in october of 2023 and then i left the beginning

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of 2024. So, of course, you left me with a cliffhanger.

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What were you doing? Yeah. So I was working for

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a big fortune turning company, like you mentioned

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at the top, helping train people within my large

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company, not my large company, the company I

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worked for, how to train them on how to do design

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thinking from a primarily like a building organizational

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capability perspective, if you will. And what

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that looked like was our primary offer. I talk

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about it now as an entrepreneur, as an offer,

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but that's not obviously how we thought about

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it in the corporate world. But the primary offer

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that we had was a 12 -hour training that was

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about design thinking basics. And I'll explain

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what design thinking is in a second as well.

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Over one week, so three hours, four days in a

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row, all virtual or usually virtual with 24 people.

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And we delivered. 12 to 16 of those as a team

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throughout the year. We did other things too,

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but that was like the main thing that was kind

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of like our flagship, if you will. And so let

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me talk about design thinking for a second, because

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people may say, I don't know what that even means.

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Design thinking, I describe it as it's a capital

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D designer, like someone who went to school for

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capital D design, but you're using their mindset

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and their toolkit by typically non... capital

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d designers who didn't go to school for design

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so the mindset would be human centric is like

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the simple way to describe that like think about

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who is using the actual product you're making

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the process you're developing that whatever you're

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doing there's humans involved somewhere think

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about them and that's what you should be focusing

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your efforts on not just how do we actually make

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this happen but why are we trying to make it

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happen why do they care things like that And

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then the toolkit is often personified by like

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sticky notes, but it doesn't have to be. It's

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more structured exercises in general. Sticky

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notes are a great way to do that, but it can

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be any kind of structured exercise. And what

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I love about this is it really combines my...

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I'm an engineer by schooling, at least. I have

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an engineering degree, though I never was like

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a... actual engineer but that process side mixed

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with the human side is what I love about design

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thinking so that kind of is a little bit of the

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background happy to pull any other threads if

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you got them and that's what you're doing today

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with your coaching programs Yeah. So actually,

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I can fill in a few more beats here. The first

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thing I wanted to do that I started doing when

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I first quit for about the first nine months,

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and then I pivoted to what I'm doing now, was

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helping millennial parents live regret -free

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through workshops that I had designed for my

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wife and I to use to figure out things kind of

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like, you should quit your job. Now, that decision

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didn't come through one of those state of the

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unions is what we call them. But bigger picture

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thinking is what we use those for three times

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a year. We have like a half day that we just

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do ourselves. And we talk through. Again, big

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picture things. Quadrant two, if you're familiar

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with like Stephen Covey thinking, like those

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big things that are hard to find time for in

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the day to day, but can really make a big impact.

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And I thought to myself, I love my friends. And

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if anyone's out there listening, I love you guys,

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but they could use just a little more intention

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with their life. And I want to help people do

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that. And so I started on that path, started

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to get a little bit of traction. But the next

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kind of milestone that pivoted me to what I'm

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doing now is I met a few people along the way

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at Craft and Commerce, which is Kit's in -person

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event, which is really great. It's a whole nother

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topic. I could talk about that all day. Really

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love that event. But I met a few people who knew

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my background and they said, Jake, I'm freaking

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out. I have a... I committed to doing some in

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-person coaching for some of my clients and I

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don't know what to do. Can you just help me?

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And so I ended up helping them. I had notes everywhere.

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I was really loving it. And I realized I really

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miss doing this. And that's ultimately the main

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kernel that kind of pivoted me back to what I'm

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doing now. So to kind of put a bow on that, what

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I do now is I, what I do now now is actually

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build group coaching programs for people who

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have a lot of expertise, but don't know how,

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or don't want to spend the time actually structuring

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and developing a program to help people transform

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in some way. And it's all using that design thinking

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methodology and kind of mindset and facilitation

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skills and all those sorts of things. So what

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I'm loving about your story is how you've been

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pivoting. Seems like you experimented and touched

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a pain point that as a millennial parent, you're

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looking for that balance and you're looking to

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live that life regret free. Now you've got me

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thinking. am i living regret free yeah i mean

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it is it is so true and and uh if i can um take

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a detour here for just a second because it is

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a big part of why like so i called my company

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intention craft and it still applies to what

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i do because i've kept coming back to throughout

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my life like let's just be intentional like what

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are we actually trying to do here and that's

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why i like this zooming out time and so like

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the the kid thing is um absolutely true so i

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have at the time of this recording a five -year

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-old and an eight -year -old and if i stop and

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think about it my eight -year -old is already

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basically halfway done with their time that they're

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going to spend with me. And that may be even

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like a little optimistic because I'm assuming

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when they become teenagers, they're going to

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start wanting to spend more and more time with

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their friends and less time with dad, even though

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they're going to want to spend time with me,

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hopefully. Right. I think I'm laying a good foundation,

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but like it really puts in a stark contrast.

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Like what are we actually doing here? everybody.

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Like, what are we, like, what are we doing? And

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so that tied in with one of the decisions. I

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quit my job without doing a side hustle. So I

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made the decision. I didn't want to take extra

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time in the evenings or in the weekend away from

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my kids. And I didn't feel good because I really

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loved my job. Maybe if I was like bitter about

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my job, I might've not cared so much to work

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during like regular work hours, but I didn't

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want to do that. And so that was part of the

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decision. It's like, well, what is like truly

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important? And the regret -free thing, I didn't

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mention this and I'm happy to dig into this if

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you want, but I love any opportunity I can mention

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this. I'd love to mention it. In 2015, after

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my wife and I got married, we actually quit our

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jobs to travel for a year. And the decision factor

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there was literally, we asked ourself the question,

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will we regret not doing this? We were looking

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at doing just like a month off, which at the

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time was also like huge because we were both

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in corporate America and that's like a ton of

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time off. And we said, we have an opportunity.

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Will we regret it? The answer was, yeah, I think

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we'll look back and we'll regret it. So it's

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really hard to kind of project into the future.

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But, you know, you make some assumptions and

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then you figure out what decisions now will hopefully

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lead to living regret free. Brief, brief, brief

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aside from an entrepreneurial perspective, by

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the way. trying to sell something that is about

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living regret -free is really difficult because

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that is such a long timeframe to literally have

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my promise of, I will help you as a millennial

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parent live regret -free. You have to be on your

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deathbed looking back and say, oh yeah, Jake

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did actually help me live regret -free. So that

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was a little bit of a big scope, but the message

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still came through, I think. But anyway, I digress.

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Can I jump on something you just mentioned that

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actually will help us pivot? I'm happy to follow

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you wherever, but you were mentioning intention

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craft and you said perfection. And this is a

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big thing. I actually did some work on, I guess,

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what would be called like my premise, if you

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will. I was working with another guy I met along

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the way on my journey. I came as I'm working

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through my thoughts on perfection. This is something

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I see with a lot of people who try to build programs.

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They are worried that it's not good enough and

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they try to build everything and they're trying

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to make everything perfect. Like, please don't

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do that. We can talk tactics and some of my recommendations

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there. We can go deeper on that. But what I realized

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in talking through this was my view is perfection

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is, I think a lot of people know this or will

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certainly agree with this, but perfection should

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never be the goal. But I think excellence. is

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the goal and those two things are different because

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perfection implies that there is a point that

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you can stop and you're saying this is like i've

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reached the pinnacle or whatever and i don't

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believe that in general with most things i'm

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sure there's a few exceptions that maybe prove

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the rule But excellence, I like the framing of

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excellence because it's not about getting it

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right. It's about caring enough to keep making

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it better. And that's how I've been thinking

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about it and trying to teach people. You don't

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have to start perfect, just like you were talking

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about, but it'll continue to get better and better

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and better and it will be excellent. And that's

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what you need. You don't need perfection. You

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need excellence. So anyway, that's like one of

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my recent soapboxes that I've had on my mind

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lately. So you named your company Intention Craft.

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What's the meaning behind your name? Yeah. So

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I'll share a little bit. There's a book and also

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a TV show called His Dark Materials, or it's

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a series of books, actually. The Golden Compass

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is probably the most known of those. And there's

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an HBO show that we were watching at the time

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when we were talking about this idea. And I love

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this concept of being intentional. And there's

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a physical machine called an intention craft.

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You think and it will take you there, basically.

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And we're like, oh, that's interesting. Intention,

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like that obviously stuck out like a lightning

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rod. Because intention's always been important.

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And craft in that sense was more about like the

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craft, like the vehicle, the craft. But I love

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this concept of craft because it implies that

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it's also something you're building that you

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can, there can be, like craft to me evokes like

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woodworking and things like that, where yes,

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there is art, but there's also technique and

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there's better ways to do it. There's established

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ways to make your woodworking. a certain way

00:11:55.759 --> 00:11:57.740
and there's certain like patterns you can follow

00:11:57.740 --> 00:12:00.639
and there's an artistry to it but intention of

00:12:00.639 --> 00:12:02.220
just being intentional in general thinking about

00:12:02.220 --> 00:12:03.799
where you want to go before you try to go there

00:12:03.799 --> 00:12:05.799
even if you don't end up exactly where you want

00:12:05.799 --> 00:12:07.580
to go intention has been really important then

00:12:07.580 --> 00:12:09.980
the craft piece is it's not all art there is

00:12:09.980 --> 00:12:12.200
technique but there's also a mix of art and technique

00:12:12.200 --> 00:12:14.120
so that's kind of why that resonated with me

00:12:14.120 --> 00:12:16.580
besides the lightning bolt of the idea specifically

00:12:16.580 --> 00:12:18.940
from that show i mentioned so there you go there's

00:12:18.940 --> 00:12:23.350
my story What one key piece of advice would you

00:12:23.350 --> 00:12:26.230
give to someone that's listening to this episode

00:12:26.230 --> 00:12:30.110
today that perhaps is in that situation that

00:12:30.110 --> 00:12:33.990
you were, comfortable, complacent, and whether

00:12:33.990 --> 00:12:36.789
or not they leave their job, they had that vision

00:12:36.789 --> 00:12:41.269
or that desire to try something new and be intentional

00:12:41.269 --> 00:12:46.669
about it? I love that. Okay, so for me, the biggest

00:12:46.669 --> 00:12:48.769
thing that probably comes to my mind is like

00:12:48.769 --> 00:12:53.149
a... core tenet of design thinking and it applies

00:12:53.149 --> 00:12:55.509
to lots of things. And it's, if you are curious

00:12:55.509 --> 00:12:58.309
about something, find some way to go test that

00:12:58.309 --> 00:13:02.649
idea. Now, I tested my idea when I left just

00:13:02.649 --> 00:13:04.690
to draw a line because my wife and I had been

00:13:04.690 --> 00:13:07.889
doing these state unions ourself and I knew it

00:13:07.889 --> 00:13:10.889
worked for us. That was the test for me. But

00:13:10.889 --> 00:13:12.950
whatever it is for you, think about how can I

00:13:12.950 --> 00:13:15.149
go try that? And there's a book I read recently

00:13:15.149 --> 00:13:18.519
from Jim Collins, who's most famous for... good

00:13:18.519 --> 00:13:20.480
to great. But there's another one of his books

00:13:20.480 --> 00:13:22.960
called Great by Choice. I believe that's the

00:13:22.960 --> 00:13:26.360
one. And he talks about firing bullets before

00:13:26.360 --> 00:13:28.940
cannonballs. And the metaphor here, which I think

00:13:28.940 --> 00:13:31.700
will be really useful, is imagine you're on an

00:13:31.700 --> 00:13:34.539
old -timey ship or whatever on the sea, like

00:13:34.539 --> 00:13:37.580
a wooden ship, and you have only so much gunpowder

00:13:37.580 --> 00:13:41.000
to fire a cannonball and a little bit of extra,

00:13:41.080 --> 00:13:43.440
but you can't fire multiple cannonballs. So you're

00:13:43.440 --> 00:13:45.019
going to have to be really lucky to hit that

00:13:45.019 --> 00:13:47.419
ship you're trying to sink. with a cannonball

00:13:47.419 --> 00:13:49.840
the better way to do it is to fire a few bullets

00:13:49.840 --> 00:13:51.820
to see if you hit that if you're on the right

00:13:51.820 --> 00:13:53.879
trajectory and then then you can aim and then

00:13:53.879 --> 00:13:55.740
you're much more likely to actually be successful

00:13:55.740 --> 00:13:57.639
at whatever you're trying to accomplish so the

00:13:57.639 --> 00:14:01.139
metaphor here is the the bullets are low risk

00:14:01.139 --> 00:14:04.840
uh low effort and there might have been a third

00:14:04.840 --> 00:14:06.759
thing but those are the two big ones for me is

00:14:06.759 --> 00:14:08.720
like how can i try this in a way that doesn't

00:14:08.720 --> 00:14:11.240
take a ton of time starts to get me some some

00:14:11.240 --> 00:14:14.600
idea of am i on track before you go all in so

00:14:15.049 --> 00:14:16.210
And that will give you a lot of information.

00:14:16.350 --> 00:14:18.549
Do I like this? Does anybody care about this?

00:14:18.850 --> 00:14:20.669
Things like that. We could talk tactics, tactics,

00:14:20.730 --> 00:14:23.250
like entrepreneurial stuff, but that's kind of

00:14:23.250 --> 00:14:26.269
the core concept. So that's what I'll share on

00:14:26.269 --> 00:14:29.110
that front. So where can we connect with you

00:14:29.110 --> 00:14:32.789
online? Yeah, definitely. So if you're interested

00:14:32.789 --> 00:14:34.830
in seeing more about what I do or getting a start

00:14:34.830 --> 00:14:37.779
on what that. core of a program or a workshop

00:14:37.779 --> 00:14:40.940
might be, you can actually go to workshopy .com

00:14:40.940 --> 00:14:44.179
and you can get a workbook and you can actually

00:14:44.179 --> 00:14:45.720
schedule time with me if you want to talk through

00:14:45.720 --> 00:14:47.659
any kind of group experience you want to design.

00:14:47.759 --> 00:14:49.440
I'm happy to help give you my advice. That's

00:14:49.440 --> 00:14:52.919
workshopy .com. Well, thank you so much for joining

00:14:52.919 --> 00:14:55.279
me today, Jake. Thanks for having me, Sheila.

00:14:55.840 --> 00:14:58.559
And thank you all for tuning in to another episode.

00:14:58.740 --> 00:14:59.700
Until next time.
