March 31, 2025 • 46 mins
Jason Shafton, founder and CEO of Winston Francois, wrestles with the challenge every entrepreneur-parent knows too well: how to build a thriving business while being fully present for family.
After experiencing a profound personal loss, Jason's perspective on work transformed, yet he still struggles with the "always on" mentality. In this coaching session, we explore how perfectionism and the need to be needed keep notifications perpetually active, preventing true presence anywhere. Discover practical steps toward becoming "dad by default" instead of "working by default."
Enjoyed this episode? Ready to take your leadership and personal growth to the next level? Please visit my website to learn more about coaching with me.
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Episode Transcript
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Speaker 1 (00:00):
Welcome to Slow Down, to Speed Up, where we have real
one-time coaching sessions withstartup founders working
through the challenges ofleadership.
I'm your host and executivecoach, brian Wang.
Today on the show, we're joinedby Jason Shafton, founder and
CEO of a growing marketingagency, who's wrestling with
what might be entrepreneurship'smost universal struggle how to
be fully present for both yourbusiness and your family when
(00:20):
there's only one of you.
What begins as a seeminglystraightforward exploration
about work-life balance takes anunexpected turn when Jason
reveals a profound personal lossthat transformed his
relationship with work.
Two years ago, jason and hiswife lost twins in pregnancy,
which forced him to radicallydelegate his business
responsibilities while hefocused on his family.
Now, with a healthy new babyand a thriving business, he
(00:42):
finds himself caught between twoworlds hearing his infant's
laughter from the next roomwhile trying to grow his company
.
As our session progresses, webegin to uncover the deeper
patterns beneath this tension.
It's not just about timemanagement, but about presence,
perfectionism and the difficultyof saying no.
If this describes you and itprobably does if you're
listening to this, then you'llget a lot out of this episode.
(01:03):
Let's listen in.
Hey, jason, let's listen in.
We spoke a little bit beforethis, and you know we talked
about getting on for a coachingsession.
So yeah, jason, thanks forcoming on.
I'm really excited to have youhere and I'm curious like what
(01:35):
are we getting into today?
Speaker 2 (01:36):
Look, I think for me the most important thing is
finding a way to have a mindfuland healthy approach to my work
alongside a growing and youngfamily that has been through a
lot in the last couple of years.
I shared with you previouslyand we can dig into here how
loss and grief impacted myperspective on entrepreneurship
(01:58):
and growing a business, and Ithink if we can spend our time
together today just digging intothat and how to how to balance
the the tug of wanting to spendmore time with my kids and my
wife while also trying to growand scale a successful
enterprise is is tricky.
It's just really hard.
Speaker 1 (02:19):
Yeah, yeah, I can absolutely relate to that, and
my guess is that you've sort ofbeen wrestling with that
question for a while now and I'mwondering if maybe we can start
by just asking how have youexperienced that tension, just
as you're navigating it?
(02:39):
Describe for me what it feelslike as you're trying it, what,
what, like.
Describe for me what, what itfeels like as you're, as you're
trying to wrestle with it.
Speaker 2 (02:46):
Yeah, I think it's a, it's a sense of profound FOMO,
or or maybe guilt, in that whenI'm fully engaged in my work, I
still have this nagging desireto kind of close the computer
(03:09):
and walk away.
And just you know, I hear my, Ihear my almost 10 month old in
the background playing, you know, with our nanny right now, like
I hear her giggling andlaughing, like, as we're having
this this session, yeah, and Ijust want to go be a part of
that.
Yeah, um, and I think, againstthe backdrop of having a just
terrible loss, uh, almost twoyears ago now, um, and we should
(03:34):
, we should get into that, but Ithink that's the life is is
exceedingly precious and brief,and so I, you know, I want to
find a way to maximize myenjoyment of it while also
facilitating and providing formy family in a meaningful way,
which is those two things are atgreat odds with one another.
Speaker 1 (03:53):
It feels like so the tension you, you feel it kind of
viscerally when you're at workand you can hear your, your kid
in the background and it's likeyou're wanting to be in two
different places at once.
Is that right?
Speaker 2 (04:09):
Yes, and I think that's part of the challenge of
working from home.
I previously had an office so Icould kind of be at arm's
length a little bit and not, youknow, hearing the fun that's
happening in my home.
But I have a home office nowand so I think one it's great.
Like I want to go have lunchwith my wife she also works from
home or want to just pop in onmy my you know, less than one
year old, who just woke up froma nap.
(04:31):
I can and that part's great.
But also, you know, I, I, I dohave to work, I am, I am kind of
building a building, a businessthat requires a lot of my time
and attention and some weeksit's, you know, 60 or 80 hours a
week.
Speaker 1 (04:47):
So I would imagine it's like you take both of those
roles really seriously like tobe a really present, loving
father and husband I'm rollingthose two together and then also
like to be a provider and abusiness owner or someone who's
like tending to that and takingthat very seriously as well.
That's right, yeah, and so thismight be a weird question, but
(05:09):
what makes those two things feellike they can't kind of work?
Speaker 2 (05:14):
together.
I think I've found a good wayof them working together.
For example, my older daughter,who's almost five I take her to
school most mornings and pickher up after school and take her
to extracurriculars.
So I feel like I'm kind ofdoing a pretty good job there,
considering even though I amworking hard.
But I think the reason why Ifeel like the overall there's
(05:39):
overall incompatibility betweenbeing an entrepreneur and having
a family is that you know whenyou're, when you're the boss,
and it's your business and it'syour thing, um, you're always on
, you're just never, there's no,there's no off button.
And the hardest problems arethe ones that always cross your
desk, the ones that nobody elsecan solve, nobody else can deal
(06:00):
with.
So I think that's what Igrapple with most days is like,
you know, I'll get a, a Slackmessage or a text message or an
email that I have to attend toand it has to be attended to
right now, and you know I mightbe spending time with the family
, but I have to.
I have to pause and handle it.
Or, you know, and I thinkthat's where the or is is
important here to your, to yourquestion is like or, uh, and
(06:23):
maybe, maybe the what happens isnot so bad.
But, um, you know, I think, ifit's like, oh, we're going to
lose that client or we're gonnayou know there's going to be
some sort of uh you knowsignificant problem or
downstream impact that
Speaker 1 (06:37):
results in more of my time being eaten by the by the
right yeah, so so you sort ofhave the situation where lots of
things can come across yourdesk there's this fire, this
thing that we got to take careof, and those all have the
potential to pull you away fromum, your you.
(07:00):
When you're being with yourfamily if I'm hearing that right
, that's right, yeah.
And unlike when you're not anentrepreneur, as the founder
owner, I would imagine, tell meif this is right it sort of
feels like you can't switch off.
You talked about always beingon, so there's some party that's
(07:20):
always kind of monitoring forthat as well.
Speaker 2 (07:23):
Yeah, I think so.
I've been an employee and I'vebeen a founder and I think the
difference between the two is,as an employee, it's somebody
else's thing.
You're working for someone, youknow, you.
The expectation is, you knowwhether it's a nine to five and
a big company, or maybe it's astartup, and you're working a
lot harder than that.
But ultimately, like you know,you're not as invested and
(07:47):
therefore not as, and also notthe person that the buck stops
with.
Speaker 1 (07:52):
So you can potentially get you know, get a
little bit of a reprieve rightwhen, whenever you want, to, and
so I'm I'm curious about uh,maybe it's just the example that
you just mentioned or maybeit's a different example, but if
you can describe that momentwhere you're feeling that
(08:15):
tension the most stronglybetween being provider and dad
and husband, and maybe it's thatmost recent example example,
but I'm curious if we can gointo that tension itself.
Speaker 2 (08:28):
I think it stems for me, um, from you know this kind
of formative and perspectivealtering moment.
That happened a couple yearsago.
So my wife and I were pregnant.
She was pregnant, but I say we,we had, uh, twins on the way
and in April of 2022, 2023,excuse me at 20 weeks pregnant,
(08:52):
she went into early labor anddelivered the twins and they
passed away because they weren'table to survive at that
gestational age.
So after that happened, I justkind of rethought what was
actually important and andbasically said you know, I'm
(09:14):
just going to delegate out asmuch of my core responsibility
with this business as possibleand, you know, hire somebody to
manage all of my kind of socialmedia channels and content and
the thought leadership work Iwas doing.
Let's hire somebody to dobusiness development and, you
know, the founder led sales Iwas doing.
I'll have someone else do thatand I'll kind of just give all
(09:36):
of this responsibility to othersand just turn inward and focus
on, focus on my, my wife, who'sjust been through this horrible
experience that we've beenthrough together.
And so I think I got to seewhat that was like and for what
(09:57):
it's worth my business suffered,while I was also emotionally
suffering as someone grievingthe loss of his kids.
So on the other side of it nowalmost two years, I think I
wouldn't do it again that way isto be invested in going through
(10:24):
whatever my family is goingthrough and also invested in my
own thing.
I think you know I just saw aninterview with Brian Chesky the
other day and it was like he waslike being an entrepreneur, at
least for me, is incompatiblewith having a family.
It's like man.
I don't love the sound of that.
I don't think.
I think to your question.
I think it's possible.
(10:44):
I just haven't quite figured itout yet.
Sure.
Speaker 1 (10:49):
So, yeah, it sounds like when you and your wife and
your family were going throughthat a couple of years ago, you
sort of swung this one way.
It's like, hey, I'm going toset as much of this aside as I
can so I can just really be withmy family and set as much of
this aside as I can, so I canjust really be with my family.
And then you sort of describedhow like, oh, it's not quite how
you do it.
If you were to do it over again, and so I would imagine that
(11:12):
you're, you're still, you'restill constantly feeling that
tension is kind of swinging backand forth, right, yeah, so
let's say you were referencingit earlier You're working,
you're at work, and then you'refeeling the pull of family,
right, and it's a sweet pull,right, I'm a dad and you're a
(11:37):
dad.
You know what that feels like.
I'm curious what do you notice?
Are the thoughts, feelingshappening, occurring to you
internally?
What's going on there?
Speaker 2 (11:49):
Yeah, I think, to the question.
It is a sweet feeling.
There's just this overflowingkind of feeling of love and
desire.
So the end of that story is avery happy ending.
Four months later my wife gotpregnant again and so we now
have this happy, healthy baby.
She's going to be one almost twoyears to the day after we lost
(12:12):
the twins and every time shesees me I come out of my office
and I walk up to her and she'slike just started swinging her
arms and laughing and just likethere's this abundance of joy
right.
And so you know, nobody at workreacts that way when I'm about
to see them or talk to them.
So I think there's theunconditional love that comes
(12:37):
from family and certainly ourprogeny and our little ones who,
mom and dad at this veryspecial age, are the entire
world.
I think they say babies don'teven realize that they're
different from their mom fornine months.
So I am different to her andit's very exciting when she sees
me and I think you know if I,even when I go pick up my older
(13:00):
daughter from school, you know Iget a similar, maybe a more
muted reaction but, a similarreaction.
Oh, dad is here to to pick me up.
I'm going home, yeah I'm goinghome, guys, bye, yeah, and uh,
and I think it's that that's thefeeling.
It's just like this immense, uh, you know, uh radiating warmth
of, and I think the onlycomparison to it in my
(13:22):
professional life is like afeeling of a profound sense of
accomplishment and like pride indoing something that was really
hard or maybe been thoughtpreviously impossible, and
accomplishing it.
And then you know, I think thenthere's the like, but now what
you know and I and I don't.
Speaker 1 (13:53):
I don keep at the level of feeling in a perfect
world like what's.
How would you describe the sortof feelings that you're you're
actually experiencing betweenboth with work and family?
I'm not sure how to answer thatone.
Speaker 2 (14:13):
Take your time and if you have to guess, that's okay
too.
Speaker 1 (14:19):
Maybe ask it again and I'll try.
Yeah, perfect world.
What do you notice you'refeeling on a regular basis when
it comes to being with yourfamily, and also when it comes
to being at work and even inbetween?
Yeah.
Speaker 2 (14:39):
I think with family it's, you know, it's just like a
lot of joy, and with a new baby, there's just like lots of
firsts and so, just, uh, thisfeeling of excitement and
anticipation of what is shegoing to do next.
Is she going to take the firststep today, is she going to say
a new word today?
(14:59):
Uh, those are, you know,there's like an anticipatory
excitement I would describe asthe family feeling.
And and then with work, I think, once you get to a certain
level of accomplishment, youknow we, we grew this business
to seven figures and that waslike really exciting.
And then, you know, the nextmilestone is eight figures.
(15:20):
We're not there yet and, Ithink, pushing really hard to
get there.
But looking around and deciding,like, is it worth it?
Are the trade-offs worth it?
I think so, but it's hard toget there.
But looking around and decidinglike, is it worth it?
Are the trade-offs worth it?
Uh, I think so, but it's hardto, it's hard to say, and um,
and I think it's, I think workgenerates a lot more whiplash,
frustration, um, kind of highsand lows, whereas, like family
(15:43):
life right now is a lot of highsand and I think that's the big
difference- yeah.
Speaker 1 (15:49):
So I noticed that there's just this like we're
raising this kid and we're likeor taking delight in how they're
developing and what they'rediscovering, and there's this
joy.
And then with work, it'sdifferent.
But there's this joy and thenwith work, it's different, but
there's this.
There's, I hear, uh, ambition,we're gonna take this thing on,
(16:13):
we're gonna, uh, achieve thisgoal, and now we're, maybe we're
considering the next thing.
So there's this climb.
I, I notice, right, and yeah,I'm imagining like there's these
parts of you like there's a,there's like the part Right, and
yeah, I'm imagining likethere's these parts of you.
There's a.
There's like the part of Jasonthat like loves the climb, loves
(16:34):
the, the, the accomplishment,and then there's also this part
of Jason that like loves to justbe the dad, who's like
nurturing and raising and takingdelight in that, and I'm just
sort of imagining this worldwhere there's room for both of
that.
I'm curious what comes up foryou, as I just even describe
(16:57):
that.
Speaker 2 (16:58):
Yeah, I think the challenge is we just all have
the same 24 hours in the day, soit's like what is the thing
that I give up in order to haveboth?
Because I think right nowthere's good days where I have a
lot of family time and there's,you know, days where I have a
(17:18):
lot of work time that don't feelas as good on the family front,
like yesterday.
You said being a dad.
Right?
Yesterday our nanny was out, um, like off work, and so I was.
I was just being a dad, right.
Yesterday our nanny was out,like off work, and so I was just
being a dad most of the day Ididn't really have any meetings
and I just hung out with our kidand I helped her take naps and,
you know, made sure she ate andthat was great.
(17:39):
Like I turned to my wife I saidyou let me know when I can
become a stay-at-home dad,because I enjoyed this a lot.
But I think that's thechallenge, maybe, and the stigma
of like.
You know, even saying thatfeels weird to me.
It's like, oh, can I say that?
Like is somebody going to hearthat and be like, well, he's not
(18:01):
serious about what he's tryingto do professionally if he just
wants to be a stay-at-home dad.
It's like I I think both thingscan be true to your point, to
your question, but it it doesfeel like there's just a limited
, finite amount of time and it'svery hard to try to do all of
it very well you're absolutelyright.
Speaker 1 (18:20):
There is a finite amount of time, right?
Or we all have the same 24hours and so ultimately it's
it's so much of it comes down toour decisions around that and
how we relate to all that.
I'm going to ask maybe astrange question.
And so let's just imagine aworld where you're feeling
(19:00):
really at peace with how you'vedecided to spend your time
between work and family, andjust take a moment to just
imagine that for a moment.
There's no questioning, right?
So just you're in this, in thisspace where there's like, yeah,
like this, this feels right,how I've decided to do this and
and maybe even a bit of pride onhow you've done that.
Let me know if you're there asyou're imagining that.
Okay, great, so what do younotice?
(19:26):
Just looking around the world,looking around the situation,
what do you notice in all that?
Speaker 2 (19:35):
I think it's an expansion of what I'm doing
today, so it's getting both ofmy girls off to school when my
little one goes to preschool inthe fall, picking them both up
at the end of the day, beingpresent with them in the evening
, traveling as little aspossible for work, just being
(20:01):
dad by default, as much as Ipossibly can by default, okay,
as opposed to working by default, which I think is what I do now
.
Speaker 1 (20:12):
Okay, cool, we'll go back to that for a second, but
anything else that you'renoticing, just in this imaginary
space, I think there's spacefor me and the things I like to
do too.
Speaker 2 (20:25):
I think I had hoped we had joined a country club and
I'd hoped I'd get into golfover the last couple years, but
it just hasn't been the time.
So perhaps I can play around agolf once a week as well in that
world, while the kids are atschool.
So I'm not missing family time.
But, uh, that would be, thatwould be really nice okay, great
(20:45):
, so you described like dad bydefault.
Speaker 1 (20:49):
The kids are off to school in their routine.
There you've got golf.
So from your current vantagepoint, when you're looking at
that picture, is there anythinggetting in the way of that?
Do you see anything that's likeoh, this is.
Speaker 2 (21:05):
Yeah, it's anywhere between six and eight hours of
meetings every single day.
Ah, um, you know the needs ofmy team, the needs of my clients
um uh, you know traveling, sohaving to to go and meet with
with clients and team membersand attend events, and you know
(21:27):
work with partners all over thecountry or the world at all,
okay so let's, let's talk aboutthat then.
Speaker 1 (21:33):
So, okay, six to eight hours a day, you know lots
of demands, okay?
So there's a world out therewhere like my dad, by default, I
would imagine that requiresmaybe some reshuffling or
restructuring of what's going onat work.
Does that seem correct?
Speaker 2 (21:47):
yes, absolutely.
I think's a.
I think there's a world inwhich I, you know, I find a
balance of delegation, kind ofsaying no to things, pushing
things on to other members ofthe team and also limiting the
things that I directly do versuscan have someone else do yeah,
Okay.
So there's like a list of anumber of things that you could
do versus can have someone elsedo.
Speaker 1 (22:07):
Yeah, okay, so there's like a list of a number
of things that you could bedoing there.
Do any kind of pop up in termsof like the first, first order
of business or kind of highestleverage thing you could be
doing here.
Speaker 2 (22:20):
I think the one that I just can't give up but just
always bubbles up is, likefounder led sales and business
development.
Development, like it has to beme for now, I think, until we
get to that, that threshold of a, you know, an eight-figure
business, and at that point itcan be.
Speaker 1 (22:36):
It can be someone else maybe so that feels like a
non-negotiable right now thatyeah, I just from experience.
Speaker 2 (22:42):
It feels like I can't , um, I can't, let go of that
and expect the business to grow.
So I think if I can channel allof my time and energy into that
and then basically eliminate asmuch of everything else as I
can, then maybe I cut the amountof time necessary for me to do
what I'm doing in half, maybe.
Speaker 1 (23:02):
Okay, so let's play it out.
So let's say we're describing aworld where, all right,
founder-led sales still squarelyon your plate, but you've
delegated pretty much everythingelse out.
So you've got a team around youthat you trust and they're
taking care of all that.
And once you're in that space,let's go back to this idea of
(23:24):
Jason is dad by default and allthat.
How is that looking?
Is it?
Does it seem more feasible?
Speaker 2 (23:30):
I think it does.
I think there are maybe notedge cases, but frequent
occurrences where there's not athere's not an immediate um
opportunity for me to be dad bydefault, when I you know when
the thing is I need to go meetwith a prospective client and
it's across the country and Ihave to get on a plane and I'm
(23:52):
not going to be there to takethe kids to school or pick them
up or put them to bed or bethere for dinner, like that.
I think that is the trade offand I think that is not
something that can change if Iwant to continue to do what I'm
doing professionally.
Speaker 1 (24:09):
Okay, so there's like that feels hard, but sorry, say
that again.
Speaker 2 (24:14):
It feels hard, that feels, you know, like a tough, a
tough choice to make, but butthe right one for the longterm
ability to like provide for myfamily.
Speaker 1 (24:25):
Yeah, that's actually making me really curious about
the long-term for you.
Like what, yeah, what?
I'm curious what that long-termvision is for you and your
family.
Speaker 2 (24:35):
Yeah, I think, a world where I have grown the
company to a point where I havea team around me that can
operate the majority of thebusiness and I can sit on it in
a way that allows me to spend,you know, single digit hours per
week engaged in the businessand the rest of my time focused
on being a, being a dad andbeing a part of my family and
(24:58):
caring for my myself and and myclosest closest friends and
family.
And I, you know I think that'sattainable in the next maybe
three to five years.
But these little and I, youknow I think that's attainable
in the next maybe three to fiveyears but these little little
years like the, the small singledigit numbers for the for the
two kids, are there.
You know everybody says they goby really fast and so it feels
(25:19):
hard to to kind of miss anything.
Speaker 1 (25:23):
Yeah, yeah, totally.
So you've got this like threeto five year plan and, uh, you
know, god willing, you get thereand it's like cool, like now
you're, you're, you have thislike time freedom right on your
calendar.
But, yeah, this thing aroundlike missing, missing anything
you know with your kids at thisage but even you know things,
(25:44):
big and small, can, um, you canfeel like a lot that you're
missing.
They feel like a big cost.
That's right, yeah, okay.
So this is going to maybe be astrange question, okay, so
there's going to be momentswhere you do end up missing
(26:06):
things, whether you've made thechoice to do that or maybe not.
My question then is like, in inthose moments where you're not
able to be fully as present asyou would like, how do you want
to relate to that situation?
Does that, does that question,make sense?
Speaker 2 (26:29):
yeah I, you know, I think it makes sense.
I think it feels like I have togive myself permission to do
that and and be, rather thanallow it to make me feel, you
know, deep FOMO and guilt and,you know, wish that I was there.
(26:51):
Flip it perhaps on the otherside and say, look like I'm
doing this for a really goodreason, the reason that I'm not
there, and this is a, this is a,this is a means to an ends,
this is an important.
This is so important that I ammaking this choice versus, you
know, whenever it's not thatimportant, maybe I don't, I
don't make that choice.
Hold on one second.
(27:16):
One of my dogs just came inthere.
Yeah, yeah, yeah, hey, what?
Are you doing?
Get out of here.
Okay, all right, all right, letme just lay down, sorry, lay
down, no, we're not going to dothat.
You've got a guest, it's likeyou're going to pet me.
(27:38):
This is a perfect example oflike you know he wants his
attention too.
Yeah.
Speaker 1 (27:48):
Sounds like there's a lot of people in your life who
want your attention.
Speaker 2 (27:50):
Yes, it's not a bad place to be.
You know, I am, I am, I amloved, I feel the love even the.
Even the small animals want myattention yeah yeah so.
Speaker 1 (28:04):
So the question that's bubbling up for me is, no
matter what you choose, whetherit's to be with the family or
to be at work how do youapproach all that from love?
Speaker 2 (28:25):
Yeah, I think there's a am proud of myself.
I am capable of being a dad anddefault dad as much as possible
.
And also, you know, work dad,who's who's got other stuff he
has to do too.
And you know, I think, uh,there's been moments, now that
my, my daughter's almost five,where she'll turn to me and say,
dad, you know, stop working,come do this thing or get off
(28:47):
the phone.
We were at.
We were at Disneyland and I wason a work call and she said Dad
, get off the phone.
Speaker 1 (28:55):
And then, what did you?
Speaker 2 (28:56):
do.
I think I finished the call andthen I got off the phone, but
you know it was important enoughto take while I was at
Disneyland.
Yeah, in fairness.
My wife works for Disney and weget to go a lot Sure, not like
you know, the once every twoyears.
Yeah, for my daughter it's likegoing to the playground down
the street.
I understand the significanceof Disney.
Speaker 1 (29:20):
Yeah, and so yeah, okay.
So in that moment where yourdaughter was pulling at you, you
had to finish the finish thecall like what does it look like
for you to relate to all thatfrom love, including self-love?
Speaker 2 (29:43):
yeah, I think it's just you know saying to her very
sweetly, like, hey, honey, I'llbe there in a second.
I, you know, love you and justgive me, give me a minute.
Um.
And then, uh, you know beingextremely focused with the time
I am working, to say like, allright, let's be clear about what
we need to accomplish in theremaining moments of this
conversation so that I can wrapit up and also, just, you know
(30:06):
as much as it feels reallyshitty to have my daughter be,
like, get off off the phone, dad, stop working, acknowledge that
, like hey.
I, you know.
I'm I unlike her.
I do have a job and have towork.
Yeah.
And I, you know, I look, I longfor the, for the days when I
when I don't.
But we're not there yet.
Speaker 1 (30:36):
Well, what I heard in in what you described just and
just now was, like, you know,turning toward your daughter,
like acknowledging that she'sasking and and letting her know
that you will be with her.
You know, like, at this timeand I also heard this like
intentionality it's like, hey,I'm gonna, I hear you, I'm gonna
be with you.
Let me finish this you had thisintentionality of of even
getting on the call and thenfinishing the call, and you
mentioned focus and I hear thatalso as presence.
(30:56):
So, in all the things thatyou're doing, can you just be
present with whether it's being,you know, being with your
daughter or your family, or orbeing on that work call?
Right, there's, there's thiselement around, whatever it is
that you've chosen to do that,can you be fully present in that
moment?
Yeah, how does that land foryou?
Speaker 2 (31:16):
Yeah, I think that's right and I think that you know
that also comes up with my wiferight Like you're working too
much, you're on your phone toomuch.
You know pay attention to me toyour kids, be be here be here
with us.
Speaker 1 (31:31):
So how much of this question around, like how do I
balance this, is a question ofpresence.
Speaker 2 (31:39):
I think most of it yeah, it goes back to my comment
about always being on.
Right, like just always.
The notifications are always on.
The phone is almost never on.
Speaker 1 (31:53):
Do not disturb unless I'm sleeping yeah yeah, there's
one thing I know about kidsapplies to spouses too but uh,
that's what they're wanting isjust that full presence, yeah.
Speaker 2 (32:10):
Yeah, and it's hard.
I think we live in, we live inthis attention economy now where
?
You know, every single thing inyour life is vying for your
attention, in little you know,millisecond increments, and it's
, it's a constant barrage ofstimuli, whether in the real
world or in the digital world.
That you know.
Yeah, we have to learn how tomanage and turn off and we
(32:33):
wonder why, you know, kids aredistracted or glued to their
devices.
Speaker 1 (32:38):
Yeah, it can be in some sense an act of courage to
opt out of that, even in certaintime windows.
Speaker 2 (32:45):
Yeah, yeah, agreed, and I think that's the idea here
and that, and I do, you know, Ido block my calendar at the
beginning, the end of the day,yeah, to do those kind of school
pickup and drop off and yeah,um.
Speaker 1 (32:58):
so I think it's just getting getting better at doing
that more what do you thinkwould be required um of you to
say, be 20% more present withyour family compared to you know
where you are now, and I don'teven mean like changing your
calendar all that much, I justmean the quality of presence.
Speaker 2 (33:21):
Yeah, I, I think.
I think it would just be when Iam with them you know setting
the devices aside, right, andthat would end up being probably
more than 20% if I just didthat small act, because then it
becomes more difficult for me tobe pulled away, because all of
my distractions, you know, myteam is fully remote, so
everything that happens isbasically digital interruption.
Speaker 1 (33:49):
How does that thought land with you like setting the
phone aside when you're withyour family?
Speaker 2 (33:54):
Yeah, I mean I attempt to do that.
Sometimes I don't do it enough.
I think the challenge is thatthere are moments where doing
that is potentially disruptiveto ongoing opportunities that I
may miss because of timeliness.
I think when those are in play,that's not really an option,
(34:18):
but when there isn't somethinglike that, that's highly timely,
there's no reason not to justset the phone aside and take the
watch off.
Speaker 1 (34:28):
What makes it not an option?
Speaker 2 (34:33):
side and take the watch off.
What makes it not an option,like if I'm negotiating a deal
with a new client or doingsomething that requires me to be
waiting for paying attention tomy email or to my messages?
Speaker 1 (34:42):
And in that situation it feels like, oh, even in,
like the evening, I have to makesure to respond.
Speaker 2 (34:48):
Yes, sometimes, I think, you know, not all the
time but certainly there's beenenough of those instances where,
like my ability to kind ofquickly respond and engage is
the difference maker, I think,between getting and losing an
opportunity.
Speaker 1 (35:04):
Okay, so like the, that, like speed of response or
responsiveness really feels likean important asset here.
Speaker 2 (35:11):
Yeah, I think if you look at some of the most
successful people too, they havelike wildly in, like just
insane response times on thingslike email.
Right, like you know I thinkthere's there's a you know you
can email Mark Cuban and he'llreply to you within minutes.
If he does reply, right, likeyou know, this guy's a
billionaire, he doesn't have todo that.
Um, so there's something tolike being very fast acting and
(35:36):
willing to kind of jump and andand and, kind of uh, snatch up
an opportunity, a deal, whateverit is.
So I try to operate that wayprofessionally, but then I think
that's at the expense ofpersonal relationships.
So then, like, how do I, how doI play the play, that same
dynamic out personally, sure,yeah, okay.
Speaker 1 (35:57):
So let's say there's yeah, deals, live or could be
live, right, you're trying toget that across the finish line.
If we set that aside for amoment you know we talked about
a little bit this more like thedefault case where you're
putting the phone away.
I'm curious for you, like what,what's the hard part about
(36:19):
doing that?
Speaker 2 (36:21):
Well, I think, interestingly, there's like the
FOMO on the other side.
It's like what am I missing?
What?
Who has reached out?
Who needs something from me?
So I think there's also likesome of my own shit in this
which is like needing to beneeded, and so there's a
curiosity of like, all right,well, if I set this down right
(36:44):
now and somebody needs help withsomething or there's something
that someone's working on andonly I can help them, happens,
ah, okay, so let's just playwith that for a second.
Speaker 1 (36:54):
Then, um, so yeah, scenario is like oh, someone's
gonna need me.
Yeah, you're surrounded bypeople in your company, I'm sure
needing you all the time, solike this probably isn't hard,
so all right.
So there you are.
You set your phone aside.
You have a pretty goodexpectation that someone's going
to need you, and yet you'rechoosing to put that phone aside
(37:16):
anyways.
What is it that you have tofeel in that moment by putting
the phone aside?
Speaker 2 (37:26):
Yeah, I think I have to feel the pull of the priority
is is the family.
I have to feel the you know, areminder that my, that the joy
of this family time and seeingmy you know tiny baby take her
(37:47):
first steps is more importantthan whatever thing.
Speaker 1 (37:50):
Someone needs from me .
So there's this prioritizationthing.
It's like, no, my family ismore important than the others
that are kind of DMing me orwhatever it is.
Yep, yeah.
And so in that act of sayingyes to my family, no to whatever
my teammates are asking of meor whatever you know, there's
(38:11):
like the side of like, oh yeah,like this is more important with
my family.
I'm curious do you notice anyother feeling that that's
present for you, like aroundsaying the no to work colleagues
?
Speaker 2 (38:22):
yeah, I think there's also just like, uh, I'm very
much a yes, yes man and like sayprobably yes to too many things
.
So I think part of going backto your earlier question of like
how do I get 20 of that back,or 20 more of the time that I
really want, is just saying noto more things.
It all, it all kind of is tiedtogether right, like just being
(38:43):
able to more effectively manageand prioritize my time such that
the stuff that actuallydeserves it um gets it.
I think there's a underlyinglike just level of ocd and
perfectionism inside of me thathas helped me get to where I am,
but also yeah, you know,results in me obsessively
(39:04):
clearing my inbox to zero andhaving no you know unreads
across all my variouscommunication apps, and it's
like you know.
then I see my wife's email hastens of thousands of unread
emails and she doesn't care andshe's like yeah it doesn't
matter.
Speaker 1 (39:19):
Yeah, I totally get that, and so one way to look at
this is I have this habit ofsaying yes to people.
I don't like to say no topeople.
Largely, what's going on thereis there's some feeling that I
(39:42):
really don't want to feel, bysaying the no, like I'm
rejecting this person or I'mgonna lose control down I think
yeah yeah.
Is that the thing?
It's like?
Speaker 2 (39:54):
oh, if I say no to this person, that now I have to
let them down yeah, I think so,and I think, um, it comes back
to the original feeling wetalked about at the beginning of
the conversation.
It's like, uh, the guilt of,you know, not doing something.
In this case, it's in reverse,like, well, I'm abdicating a
(40:14):
professional responsibility, athing that I said I would do, or
that I should be doing, orwhatever.
And there's pressure I'mputting on myself to do all of
it.
Yeah.
Speaker 1 (40:28):
Yeah, when you're pressuring yourself to do all of
it, it's easy to feel likeyou're failing.
Yes, constantly, yeah, and sowhat would it take for you to
feel like you didn't have to doall of those things?
What would it take for you tofeel like you didn't have to do
(40:50):
all of those things.
Speaker 2 (40:50):
I don't know.
Lobotomy, probably.
I think that's just how I'mwired.
I don't know how to let go.
I think, feeling like thepeople around me were capable
enough to do all of it withoutme, um and that, and also being
okay with it happening at adifferent speed or level of
(41:13):
quality that I would do it.
Speaker 1 (41:17):
Yeah, and what's the set of steps you have to follow
to start getting getting there?
Speaker 2 (41:26):
Uh, up-leveling my team, whether through, you know,
hiring or training or both, oryou know, more radical
delegation of various tasks andnot delegating the things that
are core to the success andgrowth of the business that I
have to take responsibility for,but delegating the like very
(41:47):
small operational, back office,administrative, logistical stuff
that I still do.
Speaker 1 (41:54):
You know, when you're ceo founder of a small business
like, yeah, this is yeah, andso that that sort of project of
of delegating up levelingtraining, how much progress are
you making on that these days?
Speaker 2 (42:11):
I mean big progress, I would say.
Actually, I recently kind ofelevated my number two to chief
operating officer and she isbuilding out those systems and
process and working with me toprotect my time, we're trying to
kind of develop swim laneswhere she owns ops and I own
(42:31):
business development and there'skind of clear delineation of
what that means.
And then we were building outthis kind of virtual assistant
team.
She is building it out in thePhilippines where we have, you
know, basically round the clockcoverage so that things can
happen even while we're sleepingand progress is made.
And I think that's, you know,that's all moving in that
(42:53):
direction.
I think there's just stuff that, like I said, I won't be able
to fully delegate in the nearterm, but in the medium to long
term.
Speaker 1 (43:01):
I hope I can.
Yeah.
Well, that's great.
It sounds like you're startingto build some momentum there.
Speaker 2 (43:06):
Trying to.
It's hard.
You know, a lot of times whenyou're, when you're building a
business as you know, it's likeone step forward two steps back.
Speaker 1 (43:13):
So, yeah, yeah, yeah, that tends to be the case.
Well, jason, um, as we start toclose out here, uh, I want to
just zoom out and ask you um,yeah, like, what are you, what
are you finding you're learningthrough the conversation today?
Speaker 2 (43:30):
I think the number one thing I've learned is that a
lot of the answers to thesehard questions I already know
them.
They're just hard to accept,right, like being more present
and taking the steps to free upmy time and enable me to be more
present, are all things that,like I know what I need to do.
There's a reluctance, maybe ina resistance, to doing it, and
(43:56):
there's a safety and comfort indoing things the way I've always
done that.
Speaker 1 (43:59):
But I think growth is pushing ourselves through those
particularly hard and seeminglylike impossible barriers of of
our own design and and uh, youknow, I think you, I think you
highlighted a bunch of thingsthat I can just like, or you
helped me get to a bunch ofthings that I can just start
doing- Well, I, uh, I wanted tosay thank you for you know,
(44:24):
being willing to surface some ofthose, uh, resistances and and
yeah, those are absolutely theplaces to look and I would
encourage you to spend some timewith them because that's, as
you know, that's where thegrowth is, as we start to find
where the resistances are andstart to lean in a bit.
Speaker 2 (44:46):
I'm going to do it and I'm going to report back and
share my progress with you andhopefully this is the start of
many big changes and big movesthere you go All right, jason.
Speaker 1 (44:59):
Thank you so much.
It was a pleasure to spend timewith you.
Thanks for making the time,brian.
The always-on mentality isincredibly common among founders
and high achievers.
We wear our constantavailability like a badge of
honor, believing that immediateresponsiveness is the key to
success.
In reality, this perpetualstate of distraction prevents us
from being fully present in anyarea of our lives, whether with
our families or even with ourmost important work.
(45:21):
As a father myself, I deeplyrelate to Jason's struggle.
I know firsthand how difficultit can be to silence the mental
chatter about work.
When I'm with my kids, it's aconstant back and forth between
anxiety about your business andguilt that you're not being the
dad you want to be.
With Jason, we saw how hisperfectionism and need to be
needed were keeping hisnotifications constantly active,
(45:42):
preventing him from being fullypresent anywhere.
And yet he knows that in orderto become dad by default, he
needs to give himself permissionto feel uncomfortable when
saying no to work demands.
The most powerful thing herewas Jason's realization that
many of the answers he wasseeking weren't mysteries at all
.
They were truths he alreadyknew but found difficult to
(46:02):
accept and implement.
I found this in my own life too, the solutions are clear.
We'd just rather find reasonsthey aren't.
Whether you're building acompany, raising a family or
doing both simultaneously,presence is the ultimate
currency, and sometimes thebravest thing we can do is turn
off notifications, embrace thediscomfort of not being needed
for a while and be fully wherewe are.
(46:23):
If you found something valuablein this session, please share
it with another founder whomight be struggling with similar
challenges.
Thank you for listening and seeyou next time.
Welcome to Slow Down, to Speed Up, where we have real
one-time coaching sessions withstartup founders working
through the challenges ofleadership.
I'm your host and executivecoach, brian Wang.
Today on the show, we're joinedby Jason Shafton, founder and
CEO of a growing marketingagency, who's wrestling with
what might be entrepreneurship'smost universal struggle how to
be fully present for both yourbusiness and your family when
(00:20):
there's only one of you.
What begins as a seeminglystraightforward exploration
about work-life balance takes anunexpected turn when Jason
reveals a profound personal lossthat transformed his
relationship with work.
Two years ago, jason and hiswife lost twins in pregnancy,
which forced him to radicallydelegate his business
responsibilities while hefocused on his family.
Now, with a healthy new babyand a thriving business, he
(00:42):
finds himself caught between twoworlds hearing his infant's
laughter from the next roomwhile trying to grow his company
.
As our session progresses, webegin to uncover the deeper
patterns beneath this tension.
It's not just about timemanagement, but about presence,
perfectionism and the difficultyof saying no.
If this describes you and itprobably does if you're
listening to this, then you'llget a lot out of this episode.
(01:03):
Let's listen in.
Hey, jason, let's listen in.
We spoke a little bit beforethis, and you know we talked
about getting on for a coachingsession.
So yeah, jason, thanks forcoming on.
I'm really excited to have youhere and I'm curious like what
(01:35):
are we getting into today?
Speaker 2 (01:36):
Look, I think for me the most important thing is
finding a way to have a mindfuland healthy approach to my work
alongside a growing and youngfamily that has been through a
lot in the last couple of years.
I shared with you previouslyand we can dig into here how
loss and grief impacted myperspective on entrepreneurship
(01:58):
and growing a business, and Ithink if we can spend our time
together today just digging intothat and how to how to balance
the the tug of wanting to spendmore time with my kids and my
wife while also trying to growand scale a successful
enterprise is is tricky.
It's just really hard.
Speaker 1 (02:19):
Yeah, yeah, I can absolutely relate to that, and
my guess is that you've sort ofbeen wrestling with that
question for a while now and I'mwondering if maybe we can start
by just asking how have youexperienced that tension, just
as you're navigating it?
(02:39):
Describe for me what it feelslike as you're trying it, what,
what, like.
Describe for me what, what itfeels like as you're, as you're
trying to wrestle with it.
Speaker 2 (02:46):
Yeah, I think it's a, it's a sense of profound FOMO,
or or maybe guilt, in that whenI'm fully engaged in my work, I
still have this nagging desireto kind of close the computer
(03:09):
and walk away.
And just you know, I hear my, Ihear my almost 10 month old in
the background playing, you know, with our nanny right now, like
I hear her giggling andlaughing, like, as we're having
this this session, yeah, and Ijust want to go be a part of
that.
Yeah, um, and I think, againstthe backdrop of having a just
terrible loss, uh, almost twoyears ago now, um, and we should
(03:34):
, we should get into that, but Ithink that's the life is is
exceedingly precious and brief,and so I, you know, I want to
find a way to maximize myenjoyment of it while also
facilitating and providing formy family in a meaningful way,
which is those two things are atgreat odds with one another.
Speaker 1 (03:53):
It feels like so the tension you, you feel it kind of
viscerally when you're at workand you can hear your, your kid
in the background and it's likeyou're wanting to be in two
different places at once.
Is that right?
Speaker 2 (04:09):
Yes, and I think that's part of the challenge of
working from home.
I previously had an office so Icould kind of be at arm's
length a little bit and not, youknow, hearing the fun that's
happening in my home.
But I have a home office nowand so I think one it's great.
Like I want to go have lunchwith my wife she also works from
home or want to just pop in onmy my you know, less than one
year old, who just woke up froma nap.
(04:31):
I can and that part's great.
But also, you know, I, I, I dohave to work, I am, I am kind of
building a building, a businessthat requires a lot of my time
and attention and some weeksit's, you know, 60 or 80 hours a
week.
Speaker 1 (04:47):
So I would imagine it's like you take both of those
roles really seriously like tobe a really present, loving
father and husband I'm rollingthose two together and then also
like to be a provider and abusiness owner or someone who's
like tending to that and takingthat very seriously as well.
That's right, yeah, and so thismight be a weird question, but
(05:09):
what makes those two things feellike they can't kind of work?
Speaker 2 (05:14):
together.
I think I've found a good wayof them working together.
For example, my older daughter,who's almost five I take her to
school most mornings and pickher up after school and take her
to extracurriculars.
So I feel like I'm kind ofdoing a pretty good job there,
considering even though I amworking hard.
But I think the reason why Ifeel like the overall there's
(05:39):
overall incompatibility betweenbeing an entrepreneur and having
a family is that you know whenyou're, when you're the boss,
and it's your business and it'syour thing, um, you're always on
, you're just never, there's no,there's no off button.
And the hardest problems arethe ones that always cross your
desk, the ones that nobody elsecan solve, nobody else can deal
(06:00):
with.
So I think that's what Igrapple with most days is like,
you know, I'll get a, a Slackmessage or a text message or an
email that I have to attend toand it has to be attended to
right now, and you know I mightbe spending time with the family
, but I have to.
I have to pause and handle it.
Or, you know, and I thinkthat's where the or is is
important here to your, to yourquestion is like or, uh, and
(06:23):
maybe, maybe the what happens isnot so bad.
But, um, you know, I think, ifit's like, oh, we're going to
lose that client or we're gonnayou know there's going to be
some sort of uh you knowsignificant problem or
downstream impact that
Speaker 1 (06:37):
results in more of my time being eaten by the by the
right yeah, so so you sort ofhave the situation where lots of
things can come across yourdesk there's this fire, this
thing that we got to take careof, and those all have the
potential to pull you away fromum, your you.
(07:00):
When you're being with yourfamily if I'm hearing that right
, that's right, yeah.
And unlike when you're not anentrepreneur, as the founder
owner, I would imagine, tell meif this is right it sort of
feels like you can't switch off.
You talked about always beingon, so there's some party that's
(07:20):
always kind of monitoring forthat as well.
Speaker 2 (07:23):
Yeah, I think so.
I've been an employee and I'vebeen a founder and I think the
difference between the two is,as an employee, it's somebody
else's thing.
You're working for someone, youknow, you.
The expectation is, you knowwhether it's a nine to five and
a big company, or maybe it's astartup, and you're working a
lot harder than that.
But ultimately, like you know,you're not as invested and
(07:47):
therefore not as, and also notthe person that the buck stops
with.
Speaker 1 (07:52):
So you can potentially get you know, get a
little bit of a reprieve rightwhen, whenever you want, to, and
so I'm I'm curious about uh,maybe it's just the example that
you just mentioned or maybeit's a different example, but if
you can describe that momentwhere you're feeling that
(08:15):
tension the most stronglybetween being provider and dad
and husband, and maybe it's thatmost recent example example,
but I'm curious if we can gointo that tension itself.
Speaker 2 (08:28):
I think it stems for me, um, from you know this kind
of formative and perspectivealtering moment.
That happened a couple yearsago.
So my wife and I were pregnant.
She was pregnant, but I say we,we had, uh, twins on the way
and in April of 2022, 2023,excuse me at 20 weeks pregnant,
(08:52):
she went into early labor anddelivered the twins and they
passed away because they weren'table to survive at that
gestational age.
So after that happened, I justkind of rethought what was
actually important and andbasically said you know, I'm
(09:14):
just going to delegate out asmuch of my core responsibility
with this business as possibleand, you know, hire somebody to
manage all of my kind of socialmedia channels and content and
the thought leadership work Iwas doing.
Let's hire somebody to dobusiness development and, you
know, the founder led sales Iwas doing.
I'll have someone else do thatand I'll kind of just give all
(09:36):
of this responsibility to othersand just turn inward and focus
on, focus on my, my wife, who'sjust been through this horrible
experience that we've beenthrough together.
And so I think I got to seewhat that was like and for what
(09:57):
it's worth my business suffered,while I was also emotionally
suffering as someone grievingthe loss of his kids.
So on the other side of it nowalmost two years, I think I
wouldn't do it again that way isto be invested in going through
(10:24):
whatever my family is goingthrough and also invested in my
own thing.
I think you know I just saw aninterview with Brian Chesky the
other day and it was like he waslike being an entrepreneur, at
least for me, is incompatiblewith having a family.
It's like man.
I don't love the sound of that.
I don't think.
I think to your question.
I think it's possible.
(10:44):
I just haven't quite figured itout yet.
Sure.
Speaker 1 (10:49):
So, yeah, it sounds like when you and your wife and
your family were going throughthat a couple of years ago, you
sort of swung this one way.
It's like, hey, I'm going toset as much of this aside as I
can so I can just really be withmy family and set as much of
this aside as I can, so I canjust really be with my family.
And then you sort of describedhow like, oh, it's not quite how
you do it.
If you were to do it over again, and so I would imagine that
(11:12):
you're, you're still, you'restill constantly feeling that
tension is kind of swinging backand forth, right, yeah, so
let's say you were referencingit earlier You're working,
you're at work, and then you'refeeling the pull of family,
right, and it's a sweet pull,right, I'm a dad and you're a
(11:37):
dad.
You know what that feels like.
I'm curious what do you notice?
Are the thoughts, feelingshappening, occurring to you
internally?
What's going on there?
Speaker 2 (11:49):
Yeah, I think, to the question.
It is a sweet feeling.
There's just this overflowingkind of feeling of love and
desire.
So the end of that story is avery happy ending.
Four months later my wife gotpregnant again and so we now
have this happy, healthy baby.
She's going to be one almost twoyears to the day after we lost
(12:12):
the twins and every time shesees me I come out of my office
and I walk up to her and she'slike just started swinging her
arms and laughing and just likethere's this abundance of joy
right.
And so you know, nobody at workreacts that way when I'm about
to see them or talk to them.
So I think there's theunconditional love that comes
(12:37):
from family and certainly ourprogeny and our little ones who,
mom and dad at this veryspecial age, are the entire
world.
I think they say babies don'teven realize that they're
different from their mom fornine months.
So I am different to her andit's very exciting when she sees
me and I think you know if I,even when I go pick up my older
(13:00):
daughter from school, you know Iget a similar, maybe a more
muted reaction but, a similarreaction.
Oh, dad is here to to pick me up.
I'm going home, yeah I'm goinghome, guys, bye, yeah, and uh,
and I think it's that that's thefeeling.
It's just like this immense, uh, you know, uh radiating warmth
of, and I think the onlycomparison to it in my
(13:22):
professional life is like afeeling of a profound sense of
accomplishment and like pride indoing something that was really
hard or maybe been thoughtpreviously impossible, and
accomplishing it.
And then you know, I think thenthere's the like, but now what
you know and I and I don't.
Speaker 1 (13:53):
I don keep at the level of feeling in a perfect
world like what's.
How would you describe the sortof feelings that you're you're
actually experiencing betweenboth with work and family?
I'm not sure how to answer thatone.
Speaker 2 (14:13):
Take your time and if you have to guess, that's okay
too.
Speaker 1 (14:19):
Maybe ask it again and I'll try.
Yeah, perfect world.
What do you notice you'refeeling on a regular basis when
it comes to being with yourfamily, and also when it comes
to being at work and even inbetween?
Yeah.
Speaker 2 (14:39):
I think with family it's, you know, it's just like a
lot of joy, and with a new baby, there's just like lots of
firsts and so, just, uh, thisfeeling of excitement and
anticipation of what is shegoing to do next.
Is she going to take the firststep today, is she going to say
a new word today?
(14:59):
Uh, those are, you know,there's like an anticipatory
excitement I would describe asthe family feeling.
And and then with work, I think, once you get to a certain
level of accomplishment, youknow we, we grew this business
to seven figures and that waslike really exciting.
And then, you know, the nextmilestone is eight figures.
(15:20):
We're not there yet and, Ithink, pushing really hard to
get there.
But looking around and deciding,like, is it worth it?
Are the trade-offs worth it?
I think so, but it's hard toget there.
But looking around and decidinglike, is it worth it?
Are the trade-offs worth it?
Uh, I think so, but it's hardto, it's hard to say, and um,
and I think it's, I think workgenerates a lot more whiplash,
frustration, um, kind of highsand lows, whereas, like family
(15:43):
life right now is a lot of highsand and I think that's the big
difference- yeah.
Speaker 1 (15:49):
So I noticed that there's just this like we're
raising this kid and we're likeor taking delight in how they're
developing and what they'rediscovering, and there's this
joy.
And then with work, it'sdifferent.
But there's this joy and thenwith work, it's different, but
there's this.
There's, I hear, uh, ambition,we're gonna take this thing on,
(16:13):
we're gonna, uh, achieve thisgoal, and now we're, maybe we're
considering the next thing.
So there's this climb.
I, I notice, right, and yeah,I'm imagining like there's these
parts of you like there's a,there's like the part Right, and
yeah, I'm imagining likethere's these parts of you.
There's a.
There's like the part of Jasonthat like loves the climb, loves
(16:34):
the, the, the accomplishment,and then there's also this part
of Jason that like loves to justbe the dad, who's like
nurturing and raising and takingdelight in that, and I'm just
sort of imagining this worldwhere there's room for both of
that.
I'm curious what comes up foryou, as I just even describe
(16:57):
that.
Speaker 2 (16:58):
Yeah, I think the challenge is we just all have
the same 24 hours in the day, soit's like what is the thing
that I give up in order to haveboth?
Because I think right nowthere's good days where I have a
lot of family time and there's,you know, days where I have a
(17:18):
lot of work time that don't feelas as good on the family front,
like yesterday.
You said being a dad.
Right?
Yesterday our nanny was out, um, like off work, and so I was.
I was just being a dad, right.
Yesterday our nanny was out,like off work, and so I was just
being a dad most of the day Ididn't really have any meetings
and I just hung out with our kidand I helped her take naps and,
you know, made sure she ate andthat was great.
(17:39):
Like I turned to my wife I saidyou let me know when I can
become a stay-at-home dad,because I enjoyed this a lot.
But I think that's thechallenge, maybe, and the stigma
of like.
You know, even saying thatfeels weird to me.
It's like, oh, can I say that?
Like is somebody going to hearthat and be like, well, he's not
(18:01):
serious about what he's tryingto do professionally if he just
wants to be a stay-at-home dad.
It's like I I think both thingscan be true to your point, to
your question, but it it doesfeel like there's just a limited
, finite amount of time and it'svery hard to try to do all of
it very well you're absolutelyright.
Speaker 1 (18:20):
There is a finite amount of time, right?
Or we all have the same 24hours and so ultimately it's
it's so much of it comes down toour decisions around that and
how we relate to all that.
I'm going to ask maybe astrange question.
And so let's just imagine aworld where you're feeling
(19:00):
really at peace with how you'vedecided to spend your time
between work and family, andjust take a moment to just
imagine that for a moment.
There's no questioning, right?
So just you're in this, in thisspace where there's like, yeah,
like this, this feels right,how I've decided to do this and
and maybe even a bit of pride onhow you've done that.
Let me know if you're there asyou're imagining that.
Okay, great, so what do younotice?
(19:26):
Just looking around the world,looking around the situation,
what do you notice in all that?
Speaker 2 (19:35):
I think it's an expansion of what I'm doing
today, so it's getting both ofmy girls off to school when my
little one goes to preschool inthe fall, picking them both up
at the end of the day, beingpresent with them in the evening
, traveling as little aspossible for work, just being
(20:01):
dad by default, as much as Ipossibly can by default, okay,
as opposed to working by default, which I think is what I do now
.
Speaker 1 (20:12):
Okay, cool, we'll go back to that for a second, but
anything else that you'renoticing, just in this imaginary
space, I think there's spacefor me and the things I like to
do too.
Speaker 2 (20:25):
I think I had hoped we had joined a country club and
I'd hoped I'd get into golfover the last couple years, but
it just hasn't been the time.
So perhaps I can play around agolf once a week as well in that
world, while the kids are atschool.
So I'm not missing family time.
But, uh, that would be, thatwould be really nice okay, great
(20:45):
, so you described like dad bydefault.
Speaker 1 (20:49):
The kids are off to school in their routine.
There you've got golf.
So from your current vantagepoint, when you're looking at
that picture, is there anythinggetting in the way of that?
Do you see anything that's likeoh, this is.
Speaker 2 (21:05):
Yeah, it's anywhere between six and eight hours of
meetings every single day.
Ah, um, you know the needs ofmy team, the needs of my clients
um uh, you know traveling, sohaving to to go and meet with
with clients and team membersand attend events, and you know
(21:27):
work with partners all over thecountry or the world at all,
okay so let's, let's talk aboutthat then.
Speaker 1 (21:33):
So, okay, six to eight hours a day, you know lots
of demands, okay?
So there's a world out therewhere like my dad, by default, I
would imagine that requiresmaybe some reshuffling or
restructuring of what's going onat work.
Does that seem correct?
Speaker 2 (21:47):
yes, absolutely.
I think's a.
I think there's a world inwhich I, you know, I find a
balance of delegation, kind ofsaying no to things, pushing
things on to other members ofthe team and also limiting the
things that I directly do versuscan have someone else do yeah,
Okay.
So there's like a list of anumber of things that you could
do versus can have someone elsedo.
Speaker 1 (22:07):
Yeah, okay, so there's like a list of a number
of things that you could bedoing there.
Do any kind of pop up in termsof like the first, first order
of business or kind of highestleverage thing you could be
doing here.
Speaker 2 (22:20):
I think the one that I just can't give up but just
always bubbles up is, likefounder led sales and business
development.
Development, like it has to beme for now, I think, until we
get to that, that threshold of a, you know, an eight-figure
business, and at that point itcan be.
Speaker 1 (22:36):
It can be someone else maybe so that feels like a
non-negotiable right now thatyeah, I just from experience.
Speaker 2 (22:42):
It feels like I can't , um, I can't, let go of that
and expect the business to grow.
So I think if I can channel allof my time and energy into that
and then basically eliminate asmuch of everything else as I
can, then maybe I cut the amountof time necessary for me to do
what I'm doing in half, maybe.
Speaker 1 (23:02):
Okay, so let's play it out.
So let's say we're describing aworld where, all right,
founder-led sales still squarelyon your plate, but you've
delegated pretty much everythingelse out.
So you've got a team around youthat you trust and they're
taking care of all that.
And once you're in that space,let's go back to this idea of
(23:24):
Jason is dad by default and allthat.
How is that looking?
Is it?
Does it seem more feasible?
Speaker 2 (23:30):
I think it does.
I think there are maybe notedge cases, but frequent
occurrences where there's not athere's not an immediate um
opportunity for me to be dad bydefault, when I you know when
the thing is I need to go meetwith a prospective client and
it's across the country and Ihave to get on a plane and I'm
(23:52):
not going to be there to takethe kids to school or pick them
up or put them to bed or bethere for dinner, like that.
I think that is the trade offand I think that is not
something that can change if Iwant to continue to do what I'm
doing professionally.
Speaker 1 (24:09):
Okay, so there's like that feels hard, but sorry, say
that again.
Speaker 2 (24:14):
It feels hard, that feels, you know, like a tough, a
tough choice to make, but butthe right one for the longterm
ability to like provide for myfamily.
Speaker 1 (24:25):
Yeah, that's actually making me really curious about
the long-term for you.
Like what, yeah, what?
I'm curious what that long-termvision is for you and your
family.
Speaker 2 (24:35):
Yeah, I think, a world where I have grown the
company to a point where I havea team around me that can
operate the majority of thebusiness and I can sit on it in
a way that allows me to spend,you know, single digit hours per
week engaged in the businessand the rest of my time focused
on being a, being a dad andbeing a part of my family and
(24:58):
caring for my myself and and myclosest closest friends and
family.
And I, you know I think that'sattainable in the next maybe
three to five years.
But these little and I, youknow I think that's attainable
in the next maybe three to fiveyears but these little little
years like the, the small singledigit numbers for the for the
two kids, are there.
You know everybody says they goby really fast and so it feels
(25:19):
hard to to kind of miss anything.
Speaker 1 (25:23):
Yeah, yeah, totally.
So you've got this like threeto five year plan and, uh, you
know, god willing, you get thereand it's like cool, like now
you're, you're, you have thislike time freedom right on your
calendar.
But, yeah, this thing aroundlike missing, missing anything
you know with your kids at thisage but even you know things,
(25:44):
big and small, can, um, you canfeel like a lot that you're
missing.
They feel like a big cost.
That's right, yeah, okay.
So this is going to maybe be astrange question, okay, so
there's going to be momentswhere you do end up missing
(26:06):
things, whether you've made thechoice to do that or maybe not.
My question then is like, in inthose moments where you're not
able to be fully as present asyou would like, how do you want
to relate to that situation?
Does that, does that question,make sense?
Speaker 2 (26:29):
yeah I, you know, I think it makes sense.
I think it feels like I have togive myself permission to do
that and and be, rather thanallow it to make me feel, you
know, deep FOMO and guilt and,you know, wish that I was there.
(26:51):
Flip it perhaps on the otherside and say, look like I'm
doing this for a really goodreason, the reason that I'm not
there, and this is a, this is a,this is a means to an ends,
this is an important.
This is so important that I ammaking this choice versus, you
know, whenever it's not thatimportant, maybe I don't, I
don't make that choice.
Hold on one second.
(27:16):
One of my dogs just came inthere.
Yeah, yeah, yeah, hey, what?
Are you doing?
Get out of here.
Okay, all right, all right, letme just lay down, sorry, lay
down, no, we're not going to dothat.
You've got a guest, it's likeyou're going to pet me.
(27:38):
This is a perfect example oflike you know he wants his
attention too.
Yeah.
Speaker 1 (27:48):
Sounds like there's a lot of people in your life who
want your attention.
Speaker 2 (27:50):
Yes, it's not a bad place to be.
You know, I am, I am, I amloved, I feel the love even the.
Even the small animals want myattention yeah yeah so.
Speaker 1 (28:04):
So the question that's bubbling up for me is, no
matter what you choose, whetherit's to be with the family or
to be at work how do youapproach all that from love?
Speaker 2 (28:25):
Yeah, I think there's a am proud of myself.
I am capable of being a dad anddefault dad as much as possible
.
And also, you know, work dad,who's who's got other stuff he
has to do too.
And you know, I think, uh,there's been moments, now that
my, my daughter's almost five,where she'll turn to me and say,
dad, you know, stop working,come do this thing or get off
(28:47):
the phone.
We were at.
We were at Disneyland and I wason a work call and she said Dad
, get off the phone.
Speaker 1 (28:55):
And then, what did you?
Speaker 2 (28:56):
do.
I think I finished the call andthen I got off the phone, but
you know it was important enoughto take while I was at
Disneyland.
Yeah, in fairness.
My wife works for Disney and weget to go a lot Sure, not like
you know, the once every twoyears.
Yeah, for my daughter it's likegoing to the playground down
the street.
I understand the significanceof Disney.
Speaker 1 (29:20):
Yeah, and so yeah, okay.
So in that moment where yourdaughter was pulling at you, you
had to finish the finish thecall like what does it look like
for you to relate to all thatfrom love, including self-love?
Speaker 2 (29:43):
yeah, I think it's just you know saying to her very
sweetly, like, hey, honey, I'llbe there in a second.
I, you know, love you and justgive me, give me a minute.
Um.
And then, uh, you know beingextremely focused with the time
I am working, to say like, allright, let's be clear about what
we need to accomplish in theremaining moments of this
conversation so that I can wrapit up and also, just, you know
(30:06):
as much as it feels reallyshitty to have my daughter be,
like, get off off the phone, dad, stop working, acknowledge that
, like hey.
I, you know.
I'm I unlike her.
I do have a job and have towork.
Yeah.
And I, you know, I look, I longfor the, for the days when I
when I don't.
But we're not there yet.
Speaker 1 (30:36):
Well, what I heard in in what you described just and
just now was, like, you know,turning toward your daughter,
like acknowledging that she'sasking and and letting her know
that you will be with her.
You know, like, at this timeand I also heard this like
intentionality it's like, hey,I'm gonna, I hear you, I'm gonna
be with you.
Let me finish this you had thisintentionality of of even
getting on the call and thenfinishing the call, and you
mentioned focus and I hear thatalso as presence.
(30:56):
So, in all the things thatyou're doing, can you just be
present with whether it's being,you know, being with your
daughter or your family, or orbeing on that work call?
Right, there's, there's thiselement around, whatever it is
that you've chosen to do that,can you be fully present in that
moment?
Yeah, how does that land foryou?
Speaker 2 (31:16):
Yeah, I think that's right and I think that you know
that also comes up with my wiferight Like you're working too
much, you're on your phone toomuch.
You know pay attention to me toyour kids, be be here be here
with us.
Speaker 1 (31:31):
So how much of this question around, like how do I
balance this, is a question ofpresence.
Speaker 2 (31:39):
I think most of it yeah, it goes back to my comment
about always being on.
Right, like just always.
The notifications are always on.
The phone is almost never on.
Speaker 1 (31:53):
Do not disturb unless I'm sleeping yeah yeah, there's
one thing I know about kidsapplies to spouses too but uh,
that's what they're wanting isjust that full presence, yeah.
Speaker 2 (32:10):
Yeah, and it's hard.
I think we live in, we live inthis attention economy now where
?
You know, every single thing inyour life is vying for your
attention, in little you know,millisecond increments, and it's
, it's a constant barrage ofstimuli, whether in the real
world or in the digital world.
That you know.
Yeah, we have to learn how tomanage and turn off and we
(32:33):
wonder why, you know, kids aredistracted or glued to their
devices.
Speaker 1 (32:38):
Yeah, it can be in some sense an act of courage to
opt out of that, even in certaintime windows.
Speaker 2 (32:45):
Yeah, yeah, agreed, and I think that's the idea here
and that, and I do, you know, Ido block my calendar at the
beginning, the end of the day,yeah, to do those kind of school
pickup and drop off and yeah,um.
Speaker 1 (32:58):
so I think it's just getting getting better at doing
that more what do you thinkwould be required um of you to
say, be 20% more present withyour family compared to you know
where you are now, and I don'teven mean like changing your
calendar all that much, I justmean the quality of presence.
Speaker 2 (33:21):
Yeah, I, I think.
I think it would just be when Iam with them you know setting
the devices aside, right, andthat would end up being probably
more than 20% if I just didthat small act, because then it
becomes more difficult for me tobe pulled away, because all of
my distractions, you know, myteam is fully remote, so
everything that happens isbasically digital interruption.
Speaker 1 (33:49):
How does that thought land with you like setting the
phone aside when you're withyour family?
Speaker 2 (33:54):
Yeah, I mean I attempt to do that.
Sometimes I don't do it enough.
I think the challenge is thatthere are moments where doing
that is potentially disruptiveto ongoing opportunities that I
may miss because of timeliness.
I think when those are in play,that's not really an option,
(34:18):
but when there isn't somethinglike that, that's highly timely,
there's no reason not to justset the phone aside and take the
watch off.
Speaker 1 (34:28):
What makes it not an option?
Speaker 2 (34:33):
side and take the watch off.
What makes it not an option,like if I'm negotiating a deal
with a new client or doingsomething that requires me to be
waiting for paying attention tomy email or to my messages?
Speaker 1 (34:42):
And in that situation it feels like, oh, even in,
like the evening, I have to makesure to respond.
Speaker 2 (34:48):
Yes, sometimes, I think, you know, not all the
time but certainly there's beenenough of those instances where,
like my ability to kind ofquickly respond and engage is
the difference maker, I think,between getting and losing an
opportunity.
Speaker 1 (35:04):
Okay, so like the, that, like speed of response or
responsiveness really feels likean important asset here.
Speaker 2 (35:11):
Yeah, I think if you look at some of the most
successful people too, they havelike wildly in, like just
insane response times on thingslike email.
Right, like you know I thinkthere's there's a you know you
can email Mark Cuban and he'llreply to you within minutes.
If he does reply, right, likeyou know, this guy's a
billionaire, he doesn't have todo that.
Um, so there's something tolike being very fast acting and
(35:36):
willing to kind of jump and andand and, kind of uh, snatch up
an opportunity, a deal, whateverit is.
So I try to operate that wayprofessionally, but then I think
that's at the expense ofpersonal relationships.
So then, like, how do I, how doI play the play, that same
dynamic out personally, sure,yeah, okay.
Speaker 1 (35:57):
So let's say there's yeah, deals, live or could be
live, right, you're trying toget that across the finish line.
If we set that aside for amoment you know we talked about
a little bit this more like thedefault case where you're
putting the phone away.
I'm curious for you, like what,what's the hard part about
(36:19):
doing that?
Speaker 2 (36:21):
Well, I think, interestingly, there's like the
FOMO on the other side.
It's like what am I missing?
What?
Who has reached out?
Who needs something from me?
So I think there's also likesome of my own shit in this
which is like needing to beneeded, and so there's a
curiosity of like, all right,well, if I set this down right
(36:44):
now and somebody needs help withsomething or there's something
that someone's working on andonly I can help them, happens,
ah, okay, so let's just playwith that for a second.
Speaker 1 (36:54):
Then, um, so yeah, scenario is like oh, someone's
gonna need me.
Yeah, you're surrounded bypeople in your company, I'm sure
needing you all the time, solike this probably isn't hard,
so all right.
So there you are.
You set your phone aside.
You have a pretty goodexpectation that someone's going
to need you, and yet you'rechoosing to put that phone aside
(37:16):
anyways.
What is it that you have tofeel in that moment by putting
the phone aside?
Speaker 2 (37:26):
Yeah, I think I have to feel the pull of the priority
is is the family.
I have to feel the you know, areminder that my, that the joy
of this family time and seeingmy you know tiny baby take her
(37:47):
first steps is more importantthan whatever thing.
Speaker 1 (37:50):
Someone needs from me .
So there's this prioritizationthing.
It's like, no, my family ismore important than the others
that are kind of DMing me orwhatever it is.
Yep, yeah.
And so in that act of sayingyes to my family, no to whatever
my teammates are asking of meor whatever you know, there's
(38:11):
like the side of like, oh yeah,like this is more important with
my family.
I'm curious do you notice anyother feeling that that's
present for you, like aroundsaying the no to work colleagues
?
Speaker 2 (38:22):
yeah, I think there's also just like, uh, I'm very
much a yes, yes man and like sayprobably yes to too many things
.
So I think part of going backto your earlier question of like
how do I get 20 of that back,or 20 more of the time that I
really want, is just saying noto more things.
It all, it all kind of is tiedtogether right, like just being
(38:43):
able to more effectively manageand prioritize my time such that
the stuff that actuallydeserves it um gets it.
I think there's a underlyinglike just level of ocd and
perfectionism inside of me thathas helped me get to where I am,
but also yeah, you know,results in me obsessively
(39:04):
clearing my inbox to zero andhaving no you know unreads
across all my variouscommunication apps, and it's
like you know.
then I see my wife's email hastens of thousands of unread
emails and she doesn't care andshe's like yeah it doesn't
matter.
Speaker 1 (39:19):
Yeah, I totally get that, and so one way to look at
this is I have this habit ofsaying yes to people.
I don't like to say no topeople.
Largely, what's going on thereis there's some feeling that I
(39:42):
really don't want to feel, bysaying the no, like I'm
rejecting this person or I'mgonna lose control down I think
yeah yeah.
Is that the thing?
It's like?
Speaker 2 (39:54):
oh, if I say no to this person, that now I have to
let them down yeah, I think so,and I think, um, it comes back
to the original feeling wetalked about at the beginning of
the conversation.
It's like, uh, the guilt of,you know, not doing something.
In this case, it's in reverse,like, well, I'm abdicating a
(40:14):
professional responsibility, athing that I said I would do, or
that I should be doing, orwhatever.
And there's pressure I'mputting on myself to do all of
it.
Yeah.
Speaker 1 (40:28):
Yeah, when you're pressuring yourself to do all of
it, it's easy to feel likeyou're failing.
Yes, constantly, yeah, and sowhat would it take for you to
feel like you didn't have to doall of those things?
What would it take for you tofeel like you didn't have to do
(40:50):
all of those things.
Speaker 2 (40:50):
I don't know.
Lobotomy, probably.
I think that's just how I'mwired.
I don't know how to let go.
I think, feeling like thepeople around me were capable
enough to do all of it withoutme, um and that, and also being
okay with it happening at adifferent speed or level of
(41:13):
quality that I would do it.
Speaker 1 (41:17):
Yeah, and what's the set of steps you have to follow
to start getting getting there?
Speaker 2 (41:26):
Uh, up-leveling my team, whether through, you know,
hiring or training or both, oryou know, more radical
delegation of various tasks andnot delegating the things that
are core to the success andgrowth of the business that I
have to take responsibility for,but delegating the like very
(41:47):
small operational, back office,administrative, logistical stuff
that I still do.
Speaker 1 (41:54):
You know, when you're ceo founder of a small business
like, yeah, this is yeah, andso that that sort of project of
of delegating up levelingtraining, how much progress are
you making on that these days?
Speaker 2 (42:11):
I mean big progress, I would say.
Actually, I recently kind ofelevated my number two to chief
operating officer and she isbuilding out those systems and
process and working with me toprotect my time, we're trying to
kind of develop swim laneswhere she owns ops and I own
(42:31):
business development and there'skind of clear delineation of
what that means.
And then we were building outthis kind of virtual assistant
team.
She is building it out in thePhilippines where we have, you
know, basically round the clockcoverage so that things can
happen even while we're sleepingand progress is made.
And I think that's, you know,that's all moving in that
(42:53):
direction.
I think there's just stuff that, like I said, I won't be able
to fully delegate in the nearterm, but in the medium to long
term.
Speaker 1 (43:01):
I hope I can.
Yeah.
Well, that's great.
It sounds like you're startingto build some momentum there.
Speaker 2 (43:06):
Trying to.
It's hard.
You know, a lot of times whenyou're, when you're building a
business as you know, it's likeone step forward two steps back.
Speaker 1 (43:13):
So, yeah, yeah, yeah, that tends to be the case.
Well, jason, um, as we start toclose out here, uh, I want to
just zoom out and ask you um,yeah, like, what are you, what
are you finding you're learningthrough the conversation today?
Speaker 2 (43:30):
I think the number one thing I've learned is that a
lot of the answers to thesehard questions I already know
them.
They're just hard to accept,right, like being more present
and taking the steps to free upmy time and enable me to be more
present, are all things that,like I know what I need to do.
There's a reluctance, maybe ina resistance, to doing it, and
(43:56):
there's a safety and comfort indoing things the way I've always
done that.
Speaker 1 (43:59):
But I think growth is pushing ourselves through those
particularly hard and seeminglylike impossible barriers of of
our own design and and uh, youknow, I think you, I think you
highlighted a bunch of thingsthat I can just like, or you
helped me get to a bunch ofthings that I can just start
doing- Well, I, uh, I wanted tosay thank you for you know,
(44:24):
being willing to surface some ofthose, uh, resistances and and
yeah, those are absolutely theplaces to look and I would
encourage you to spend some timewith them because that's, as
you know, that's where thegrowth is, as we start to find
where the resistances are andstart to lean in a bit.
Speaker 2 (44:46):
I'm going to do it and I'm going to report back and
share my progress with you andhopefully this is the start of
many big changes and big movesthere you go All right, jason.
Speaker 1 (44:59):
Thank you so much.
It was a pleasure to spend timewith you.
Thanks for making the time,brian.
The always-on mentality isincredibly common among founders
and high achievers.
We wear our constantavailability like a badge of
honor, believing that immediateresponsiveness is the key to
success.
In reality, this perpetualstate of distraction prevents us
from being fully present in anyarea of our lives, whether with
our families or even with ourmost important work.
(45:21):
As a father myself, I deeplyrelate to Jason's struggle.
I know firsthand how difficultit can be to silence the mental
chatter about work.
When I'm with my kids, it's aconstant back and forth between
anxiety about your business andguilt that you're not being the
dad you want to be.
With Jason, we saw how hisperfectionism and need to be
needed were keeping hisnotifications constantly active,
(45:42):
preventing him from being fullypresent anywhere.
And yet he knows that in orderto become dad by default, he
needs to give himself permissionto feel uncomfortable when
saying no to work demands.
The most powerful thing herewas Jason's realization that
many of the answers he wasseeking weren't mysteries at all
.
They were truths he alreadyknew but found difficult to
(46:02):
accept and implement.
I found this in my own life too, the solutions are clear.
We'd just rather find reasonsthey aren't.
Whether you're building acompany, raising a family or
doing both simultaneously,presence is the ultimate
currency, and sometimes thebravest thing we can do is turn
off notifications, embrace thediscomfort of not being needed
for a while and be fully wherewe are.
(46:23):
If you found something valuablein this session, please share
it with another founder whomight be struggling with similar
challenges.
Thank you for listening and seeyou next time.
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