Welcome to Milestone Moments, the show where
we explore the journeys that lead to success.
I'm Sheila Slick, your host and founder of Five
Milestones. In every episode, we will bring you
insights from the minds of entrepreneurs, leaders
and experts who will share not just their expertise,
but the milestone moments that have reshaped
their journeys and led to significant achievements.
So if you're looking for motivation, you're in
the right place. Subscribe now and discover the
milestones that mark the path to success. Welcome
to another episode. I'm Sheila Slick, your host.
And today, my special guest is Jake Wysocki.
Jake has trained hundreds in workshop facilitations
at Fortune 200 companies, and then he left to
bring that same methodology to the world of coaching.
He now runs IntentionCraft, where he builds five
-star group coaching programs for established
experts. Welcome to the show, Jake. Thanks for
having me, Sheila. Great to be here. Well, I
normally love to start learning about why you
started Intention Craft. What was that moment,
that pivotal moment that led you to do what you're
doing today? Yeah. So for me, the biggest moment
that really led to that was probably the most
like salient moment was a conversation with my
wife. So I've been talking in general terms for
a few years. I really loved my job. We can get
into that if it's relevant before I quit. But
I've been talking about I'll do my own thing
at some point. And she. Asked me one summer,
I think it was 2023. We were just, we both were
from home and I was popped upstairs to chat with
her about something. She said, so when are you
going to do that? I said, oh, I don't know. Sometime
in the next few years, the same standard answer.
And thankfully she pressed me on it. She said,
okay, you've been saying that for a few years.
So are you just going to keep saying that for
a few years or are you actually going to do something
about it? I said, well, why aren't, why not now?
like why not just do that like this year i said
well i don't know money i love my job i don't
really want to change she's like okay are those
real reasons like go check the money thing that's
not the real reason like we can live off of my
salary for now and you can figure it out that
was the that was the case and it ultimately we
determined there is no reason not to do it now
so that's when i gave my three months notice
in october of 2023 and then i left the beginning
of 2024. So, of course, you left me with a cliffhanger.
What were you doing? Yeah. So I was working for
a big fortune turning company, like you mentioned
at the top, helping train people within my large
company, not my large company, the company I
worked for, how to train them on how to do design
thinking from a primarily like a building organizational
capability perspective, if you will. And what
that looked like was our primary offer. I talk
about it now as an entrepreneur, as an offer,
but that's not obviously how we thought about
it in the corporate world. But the primary offer
that we had was a 12 -hour training that was
about design thinking basics. And I'll explain
what design thinking is in a second as well.
Over one week, so three hours, four days in a
row, all virtual or usually virtual with 24 people.
And we delivered. 12 to 16 of those as a team
throughout the year. We did other things too,
but that was like the main thing that was kind
of like our flagship, if you will. And so let
me talk about design thinking for a second, because
people may say, I don't know what that even means.
Design thinking, I describe it as it's a capital
D designer, like someone who went to school for
capital D design, but you're using their mindset
and their toolkit by typically non... capital
d designers who didn't go to school for design
so the mindset would be human centric is like
the simple way to describe that like think about
who is using the actual product you're making
the process you're developing that whatever you're
doing there's humans involved somewhere think
about them and that's what you should be focusing
your efforts on not just how do we actually make
this happen but why are we trying to make it
happen why do they care things like that And
then the toolkit is often personified by like
sticky notes, but it doesn't have to be. It's
more structured exercises in general. Sticky
notes are a great way to do that, but it can
be any kind of structured exercise. And what
I love about this is it really combines my...
I'm an engineer by schooling, at least. I have
an engineering degree, though I never was like
a... actual engineer but that process side mixed
with the human side is what I love about design
thinking so that kind of is a little bit of the
background happy to pull any other threads if
you got them and that's what you're doing today
with your coaching programs Yeah. So actually,
I can fill in a few more beats here. The first
thing I wanted to do that I started doing when
I first quit for about the first nine months,
and then I pivoted to what I'm doing now, was
helping millennial parents live regret -free
through workshops that I had designed for my
wife and I to use to figure out things kind of
like, you should quit your job. Now, that decision
didn't come through one of those state of the
unions is what we call them. But bigger picture
thinking is what we use those for three times
a year. We have like a half day that we just
do ourselves. And we talk through. Again, big
picture things. Quadrant two, if you're familiar
with like Stephen Covey thinking, like those
big things that are hard to find time for in
the day to day, but can really make a big impact.
And I thought to myself, I love my friends. And
if anyone's out there listening, I love you guys,
but they could use just a little more intention
with their life. And I want to help people do
that. And so I started on that path, started
to get a little bit of traction. But the next
kind of milestone that pivoted me to what I'm
doing now is I met a few people along the way
at Craft and Commerce, which is Kit's in -person
event, which is really great. It's a whole nother
topic. I could talk about that all day. Really
love that event. But I met a few people who knew
my background and they said, Jake, I'm freaking
out. I have a... I committed to doing some in
-person coaching for some of my clients and I
don't know what to do. Can you just help me?
And so I ended up helping them. I had notes everywhere.
I was really loving it. And I realized I really
miss doing this. And that's ultimately the main
kernel that kind of pivoted me back to what I'm
doing now. So to kind of put a bow on that, what
I do now is I, what I do now now is actually
build group coaching programs for people who
have a lot of expertise, but don't know how,
or don't want to spend the time actually structuring
and developing a program to help people transform
in some way. And it's all using that design thinking
methodology and kind of mindset and facilitation
skills and all those sorts of things. So what
I'm loving about your story is how you've been
pivoting. Seems like you experimented and touched
a pain point that as a millennial parent, you're
looking for that balance and you're looking to
live that life regret free. Now you've got me
thinking. am i living regret free yeah i mean
it is it is so true and and uh if i can um take
a detour here for just a second because it is
a big part of why like so i called my company
intention craft and it still applies to what
i do because i've kept coming back to throughout
my life like let's just be intentional like what
are we actually trying to do here and that's
why i like this zooming out time and so like
the the kid thing is um absolutely true so i
have at the time of this recording a five -year
-old and an eight -year -old and if i stop and
think about it my eight -year -old is already
basically halfway done with their time that they're
going to spend with me. And that may be even
like a little optimistic because I'm assuming
when they become teenagers, they're going to
start wanting to spend more and more time with
their friends and less time with dad, even though
they're going to want to spend time with me,
hopefully. Right. I think I'm laying a good foundation,
but like it really puts in a stark contrast.
Like what are we actually doing here? everybody.
Like, what are we, like, what are we doing? And
so that tied in with one of the decisions. I
quit my job without doing a side hustle. So I
made the decision. I didn't want to take extra
time in the evenings or in the weekend away from
my kids. And I didn't feel good because I really
loved my job. Maybe if I was like bitter about
my job, I might've not cared so much to work
during like regular work hours, but I didn't
want to do that. And so that was part of the
decision. It's like, well, what is like truly
important? And the regret -free thing, I didn't
mention this and I'm happy to dig into this if
you want, but I love any opportunity I can mention
this. I'd love to mention it. In 2015, after
my wife and I got married, we actually quit our
jobs to travel for a year. And the decision factor
there was literally, we asked ourself the question,
will we regret not doing this? We were looking
at doing just like a month off, which at the
time was also like huge because we were both
in corporate America and that's like a ton of
time off. And we said, we have an opportunity.
Will we regret it? The answer was, yeah, I think
we'll look back and we'll regret it. So it's
really hard to kind of project into the future.
But, you know, you make some assumptions and
then you figure out what decisions now will hopefully
lead to living regret free. Brief, brief, brief
aside from an entrepreneurial perspective, by
the way. trying to sell something that is about
living regret -free is really difficult because
that is such a long timeframe to literally have
my promise of, I will help you as a millennial
parent live regret -free. You have to be on your
deathbed looking back and say, oh yeah, Jake
did actually help me live regret -free. So that
was a little bit of a big scope, but the message
still came through, I think. But anyway, I digress.
Can I jump on something you just mentioned that
actually will help us pivot? I'm happy to follow
you wherever, but you were mentioning intention
craft and you said perfection. And this is a
big thing. I actually did some work on, I guess,
what would be called like my premise, if you
will. I was working with another guy I met along
the way on my journey. I came as I'm working
through my thoughts on perfection. This is something
I see with a lot of people who try to build programs.
They are worried that it's not good enough and
they try to build everything and they're trying
to make everything perfect. Like, please don't
do that. We can talk tactics and some of my recommendations
there. We can go deeper on that. But what I realized
in talking through this was my view is perfection
is, I think a lot of people know this or will
certainly agree with this, but perfection should
never be the goal. But I think excellence. is
the goal and those two things are different because
perfection implies that there is a point that
you can stop and you're saying this is like i've
reached the pinnacle or whatever and i don't
believe that in general with most things i'm
sure there's a few exceptions that maybe prove
the rule But excellence, I like the framing of
excellence because it's not about getting it
right. It's about caring enough to keep making
it better. And that's how I've been thinking
about it and trying to teach people. You don't
have to start perfect, just like you were talking
about, but it'll continue to get better and better
and better and it will be excellent. And that's
what you need. You don't need perfection. You
need excellence. So anyway, that's like one of
my recent soapboxes that I've had on my mind
lately. So you named your company Intention Craft.
What's the meaning behind your name? Yeah. So
I'll share a little bit. There's a book and also
a TV show called His Dark Materials, or it's
a series of books, actually. The Golden Compass
is probably the most known of those. And there's
an HBO show that we were watching at the time
when we were talking about this idea. And I love
this concept of being intentional. And there's
a physical machine called an intention craft.
You think and it will take you there, basically.
And we're like, oh, that's interesting. Intention,
like that obviously stuck out like a lightning
rod. Because intention's always been important.
And craft in that sense was more about like the
craft, like the vehicle, the craft. But I love
this concept of craft because it implies that
it's also something you're building that you
can, there can be, like craft to me evokes like
woodworking and things like that, where yes,
there is art, but there's also technique and
there's better ways to do it. There's established
ways to make your woodworking. a certain way
and there's certain like patterns you can follow
and there's an artistry to it but intention of
just being intentional in general thinking about
where you want to go before you try to go there
even if you don't end up exactly where you want
to go intention has been really important then
the craft piece is it's not all art there is
technique but there's also a mix of art and technique
so that's kind of why that resonated with me
besides the lightning bolt of the idea specifically
from that show i mentioned so there you go there's
my story What one key piece of advice would you
give to someone that's listening to this episode
today that perhaps is in that situation that
you were, comfortable, complacent, and whether
or not they leave their job, they had that vision
or that desire to try something new and be intentional
about it? I love that. Okay, so for me, the biggest
thing that probably comes to my mind is like
a... core tenet of design thinking and it applies
to lots of things. And it's, if you are curious
about something, find some way to go test that
idea. Now, I tested my idea when I left just
to draw a line because my wife and I had been
doing these state unions ourself and I knew it
worked for us. That was the test for me. But
whatever it is for you, think about how can I
go try that? And there's a book I read recently
from Jim Collins, who's most famous for... good
to great. But there's another one of his books
called Great by Choice. I believe that's the
one. And he talks about firing bullets before
cannonballs. And the metaphor here, which I think
will be really useful, is imagine you're on an
old -timey ship or whatever on the sea, like
a wooden ship, and you have only so much gunpowder
to fire a cannonball and a little bit of extra,
but you can't fire multiple cannonballs. So you're
going to have to be really lucky to hit that
ship you're trying to sink. with a cannonball
the better way to do it is to fire a few bullets
to see if you hit that if you're on the right
trajectory and then then you can aim and then
you're much more likely to actually be successful
at whatever you're trying to accomplish so the
metaphor here is the the bullets are low risk
uh low effort and there might have been a third
thing but those are the two big ones for me is
like how can i try this in a way that doesn't
take a ton of time starts to get me some some
idea of am i on track before you go all in so
And that will give you a lot of information.
Do I like this? Does anybody care about this?
Things like that. We could talk tactics, tactics,
like entrepreneurial stuff, but that's kind of
the core concept. So that's what I'll share on
that front. So where can we connect with you
online? Yeah, definitely. So if you're interested
in seeing more about what I do or getting a start
on what that. core of a program or a workshop
might be, you can actually go to workshopy .com
and you can get a workbook and you can actually
schedule time with me if you want to talk through
any kind of group experience you want to design.
I'm happy to help give you my advice. That's
workshopy .com. Well, thank you so much for joining
me today, Jake. Thanks for having me, Sheila.
And thank you all for tuning in to another episode.
Until next time.