September 21, 2025 • 28 mins
Harry offers a short reading from a surprising source about an important question: How do you decide when it's time to let go?
Show notes:
- What Would Harry Do? by Juliana Sharaf
- Necessary Endings by Henry Cloud
- The Innovators Dilemma by Clayton M. Christensen
- Kodak
- Harry’s newsletter
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Harry (00:00):
I'm seeing it in every corporate environment that I'm
in (00:03):
leaders and boards that just don't know how to say,"Stop."
They don't know how to say,"Putthe brakes on this." And they
just keep piling on and what'shappening is not what they want.
Narrator (00:24):
You're listening to Traction Heroes.
Digging In to Get Results withHarry Max and Jorge Arango.
Harry (00:35):
Jorge, it is a pleasure to see you again, my friend.
Jorge (00:38):
Hey Harry, always good to see you.
Harry (00:40):
I just feel so grateful to know you're in my life and
that we have these conversationsset up.
It is super fun.
Jorge (00:48):
For sure.
I always think it's a little bitselfish of me.
We're releasing them and I hopethat people are getting value
out of them as well, but even ifthey don't, I'm getting so much
value out of our periodicconversations.
Harry (01:04):
Yeah, I agree.
I don't know that I could put myfinger on any specific change,
but I know that my overallapproach to moving through my
days has shifted a little bit.
I'm a little bit more thoughtfulbecause I feel like I've got new
tools and lenses to try on andreflect on as I move through my
(01:29):
life.
I brought something I wantedtoday.
It's really short and I stumbledon it, but it just, it hit right
at the center of the kinds ofthings that I think we
appreciate talking about mightbe useful for folks.
(01:50):
Can I just dive in or...?
Jorge (01:51):
Let's do it.
Harry (01:53):
All right, here you go.
"When you feel a path you'vechosen has reached its
conclusion, whether that's ajob, a relationship or a hobby
that no longer excites orchallenges you, it can be
tempting to put off ending whatyou've stuck with for so long.
But in doing so, we miss thechance to reinvent ourselves to
(02:16):
live fully as we cycle throughlife's seasons."
Jorge (02:23):
Oh, that is short.
Wow.
That is touching all sorts ofnerves on me.
You and I had a conversationlast year, I think, right before
I wrapped up my previous podcastand we decided to spin up this
one, right?
And it hinged on this subject,this idea that there comes a
(02:46):
time when you have to recognizethat something has run its
course and there is such a thingas inertia.
And I am someone who suffersfrom sticking with things for
too long after they've clearlyrun their course.
And I feel like it's cost meopportunities in my life.
So maybe we can unpack that.
(03:08):
What book is this?
Harry (03:10):
All right.
The title of this book is WhatWould Harry Do?
Lessons For Living Like A Herofrom the Wizarding World of
Harry Potter by Juliana Sharaf.
And I got this book while I wasout and about.
It just made me laugh when Ipicked it up.
And then, I was reading throughit and caught that and it
(03:32):
reminded me, I think, of myeither 2017 or 2018 book of the
year, which was NecessaryEndings by Dr.
Henry Cloud.
And I may have recommended thatto you at some point.
But that's a book about thinkingabout if, whether, and how to
(03:54):
end things.
And it is so critical,especially when it comes to
innovating, when it comes toproject management, when it
comes to prioritization.
Because I think most of usreally struggle with the sunk
(04:16):
cost of the time we've put intosomething or the money that
we've put into something, or theemotional investment we've put
into something.
It's really hard to stop.
Jorge (04:30):
The identity, right?
Because we build identitiesaround our careers.
Harry (04:34):
Yeah.
Jorge (04:36):
It's,"Oh, if I stop doing this and I start doing that,
does that mean I am no longer afill in the blank, job
description or whatever." Yeah,totally, I hear you.
I'm, super, super curious aboutwhat, first of all, when you
said what would Harry do, myfirst thought was like, wait a
(05:00):
second, did Harry write a newbook and I not know about this?
I thought you were the Harryalluded to in the title.
So I'm very curious about whatcontext this comes in the
wizarding world.
Harry (05:14):
Oh, interesting.
It's Don't Be a Phoenix was thechapter, and this was,"When it
comes to reinventing ourselves,muggles can learn a lot from the
mythical birds that are nostrangers to living, dying, and
living again."
Jorge (05:30):
But it said, Don't Be a Phoenix?
Harry (05:33):
Oh, I completely misread that.
It's Be a Phoenix.
Jorge (05:39):
Okay.
Yeah, that makes more sense.
Interesting.
I have fond memories of thefirst three Harry Potter books
because I read them to my kids.
But, we didn't read past thethird one for reasons that we
could go into if you want.
But I think that the Phoenix, ifI'm not mistaken, might be one
(06:02):
of the ones I didn't read.
So I don't remember what contextthat comes in.
But that's really interesting,this mythological image of the
phoenix, it obviously precedesHarry Potter and it's a powerful
one, right?
Like this idea that a way ofbeing ends and it ends
(06:23):
spectacularly, in ashes and thenfrom the ashes, new life arises,
right?
That's the basic image.
And it's a glorious arising of anew life.
It's not just new life, it'sthis spectacular bird that comes
out of the ashes.
(06:44):
And that's a great image to havein mind for this.
Harry (06:48):
And it's so funny that when I misread the chapter
title, I think that's theinertia problem, right?
The Don't Be a Phoenix is Ithink the fear of what it would
mean to effectively disintegrateinto ashes.
And when I read Be a Phoenix, Ithink, I don't know why I
(07:11):
misread it, but I can't helpfrom, sometimes a cigar is just
a cigar.
I may be reading into it furtherthan that, but the idea that we
have to embrace the destructionbefore the creation and this
goes right back to Boyd and hisdestruction and creation
(07:34):
discussions as we've talkedabout before.
But the reason I think thiscaught my attention and the
reason Dr.
Henry Cloud's book on necessaryendings was so potent, has
really come into very sharprelief with the work that I'm
doing with one particularleader.
This is a Chief Product Officerwho's about to retire.
(07:59):
And so, I've been brought in tohelp create the conditions for
this leader's departure andtheir ability to hire somebody
new and have them come in and besuccessful.
But the most interesting thingin the process has been learning
about the incredibly...
(08:23):
I don't even know what to callit.
The founder of this company isso creative and so mercurial and
so optimistic, that the companyitself just doesn't have it in
their DNA to stop things.
They just keep adding things.
(08:48):
One would think that's abnormal,but in fact, as I reflect on it,
in every organization that I'vebeen in, and I talk about this
in my book as well, just alittle bit, but the idea that we
would figure out how to stopinvesting in something, whether
it's a direction that we're inin our careers or whether it's a
(09:09):
podcast as in the case of yourInformed Life that led to our
work together here.
And hopefully this will continueon for a long time.
But the idea that people don'tthink about the approach to
pruning and really beingintentional about where to clip
(09:32):
and how to increase thelikelihood that things will grow
in a more fruitful, morepositive, direction, is leading
to a lot of aberrant behavior inthe system.
It's constant piling on and notenough piling off.
And I like to think it's aboutprioritization, but that's not
(09:55):
it.
There's something going on herethat is, we don't yet have the
tools to face the commitmentsthat we've made that need to be
deprecated and need to bereevaluated in the face of new
(10:19):
ongoing opportunities, eithersolving problems or pursuing new
challenges.
Those are all great and andgood, but unless you add more
resources to go with them,unless you figure out how you're
gonna apply those resources, allyou're really doing is adding
noise to the system.
And so many people, especiallyright now and especially in the
(10:44):
face of what's going on with AI,need to be thinking very
carefully about where they'rebeing put to their highest and
best use, and need to do a lotless of the things that are not
really the most valuable, mostuseful applications of their
(11:04):
talents and intellect andspirits, time and energy.
And it is so deeply fundamental.
And maybe it's that we don'tknow how to say"No." I'm not
quite sure, but I think there'ssomething here, and I think we
need to talk about it.
And I guess I would love to hearfrom you, how do you stop doing
(11:29):
things or how do you reevaluatewhere you're placing your energy
and your time and your...
I mean, how do you stop so thatyou can make room for the new?
Jorge (11:41):
The first answer that comes to mind is"poorly." And I
think that's because I've longhad an image of myself as a
tenacious person.
Harry (11:53):
Huh.
Jorge (11:54):
I remember very vividly, when I was much, much younger,
an incident, where, my dad hadobserved me doing something, a
behavior over and over againuntil I actually got what I was
aiming for, and he told me thathe had been watching me and he
had been sitting with acolleague of his while I was
(12:16):
doing this, and he had told thiscolleague,"Look at how tenacious
he is." And that bit of feedbackstayed with me and said,"Yeah, I
am tenacious and I stick withthings." And that's become part
of my identity.
And that...
first of all, I'll say, I thinkthat it's positive to be
tenacious and to be persistentand to stick with things.
(12:38):
But I also think that's a reallyrisky position to be in because
you can stick with things pasttheir expiration date.
At which point, like you weresaying, you're no longer adding
value, right?
The risk is that you findyourself trapped going through
(12:59):
the motions just because it'sbecome comfortable to go through
the motions.
When I discontinued The InformedLife, I had set up a workflow
that allowed me to produceepisodes of the show in a
predictable manner.
I had a schedule, I had a wholepipeline of guests.
(13:19):
I had the whole machine set upright.
And, the easiest thing to do forme was to just keep going with
it.
And what led me to make thatshift was a growing realization
that it had played its course.
(13:40):
The thing that I was working onhad played its course.
I set out to do something, hadachieved that, and it was no
longer a) producing the...
not producing results, becauseit wasn't about producing
results so much as it was aboutfulfilling what it was set out
(14:04):
to do.
Like, it had already done whatit set out to do, and now it was
just like going through themotions.
So it was that realization,coupled with what you brought up
earlier, like this idea that weare clearly in a transitional
period where AI is changingeverything and this requires
focusing attention in differentdirections.
(14:27):
And this is, I think, the mostimportant piece of this.
I think you and I are of the agewhere we might be more
consciously aware of constraintsand limitations.
I'll speak for myself.
I'm more consciously aware ofconstraints and limitations than
I was when I was much younger.
(14:49):
When you're a young person, theworld feels like your oyster,
right?
And it's like you can doanything and you can do all of
it.
And as one grows older, in mycase I'll say, as a dad, a
husband, you acquire certainresponsibilities that impinge on
(15:10):
your time.
And you have to be moreselective about what you're
doing.
And all those things, I thinkyou pick up as you age and as
you gain more responsibilities.
I would imagine that yourclient, when you're in that
stage of life, if you areretiring from a role, you've had
(15:35):
some success.
And you've also accrued certainresponsibilities.
And you have to focus your timeand energy.
You have to be more consciousabout how many plates you set up
spinning because you only havecertain amount of time and
(15:58):
capability to keep the platesgoing.
Harry (16:02):
Yeah, it's funny.
I just reflected on aconversation I was having
yesterday with a friend whosaid,"I figured out how to avoid
doing certain things.
There are some things that," hesaid,"I have to finish.
I just have it in my, I think,that tenacious gene, right?
(16:24):
I have it as part of who I thinkof myself, as somebody who has
to finish things.
They start and so things thatare too complicated or I can't
see how I'm gonna finish'em, Ijust don't start'em."
Jorge (16:39):
The flip side of that is that some things can't prove
themselves out until they'vebeen tried for a while.
A podcast is not something thatyou do a couple of episodes of
and then achieve immediatesuccess.
You have to keep doing it for awhile before you know whether
the thing is producing results.
This brings up an idea that Ithink is highly related to this,
(17:03):
and it's almost become a clichein the business world, the
innovator's dilemma, right?
Harry (17:10):
Mm-hmm.
Jorge (17:10):
The idea that if the thing that you are talking about
doing is successful, it becomesreally hard for you to
discontinue it in favor ofsomething else.
And I think that theprototypical example there is
Kodak and the fact that theyinvented digital photography yet
went under because they wereaddicted to the profits
(17:33):
generated by the chemicalphotography stuff.
And, there's so much of that inthe world, right?
And it happens not just tocompanies, it happens to people.
Like, you keep doing the samething over and over again, and
if you achieve any level ofsuccess, it's really hard to
chuck that and start somethingdifferent.
But I think that if you don'tburn your identity down every
(17:55):
once in a while and take a freshcrack at it, you run the risk of
losing relevance and falling outof step with what the world
needs from you at the moment.
Harry (18:10):
I'm sure that's right.
I've spent my whole careeralways wanting to call myself
the thing that I used to do.
I started out as a tech writer,but I was doing information
architecture and I wanted tocall myself a tech writer'cause
we didn't have a name forinformation architecture at the
time.
And then I was an informationarchitect, but I was doing out
(18:30):
of box experience work, but Iwanted to call myself an
information architect,'causethere was, nobody was an OOBE
architect at the time, right?
Out-of-box experience architect.
And that's been going on foryears.
I don't even know what to callmyself anymore.
I'm not really a product leader.
I'm, I do a certain amount ofthat.
I'm not really a straight upexecutive coach.
I call myself a player coach,but even that doesn't make any
(18:51):
sense given the kind of workthat I do, because it's this
blended coaching and consultingkind of work.
And it's in the dynamics of thework that my contribution lives,
and putting a label on it andcalling it something fancy just
so I can feel better aboutmyself isn't the thing to do.
(19:15):
But this idea of figuring outhow to let go of things that are
not serving anymore, I wish Ihad done a lot of deep thinking
and came with a bunch of reallysmart thoughts on a good theory,
and said,"Here's how do it." Butthat's not what happened.
What happened is I read thisthing in What Would Harry Do?
(19:35):
I was like, this once again issuch an important topic, because
I'm seeing it in every corporateenvironment that I'm in: leaders
and boards that just don't knowhow to say,"Stop." They don't
know how to say,"Put the brakeson this." And they just keep
(19:55):
piling on and what's happeningis not what they want.
Jorge (20:00):
Something that came to mind while you were talking
about it is that it might beeasier to do when you're
confronting a situation oftrauma or urgency.
Like we were saying, if you'resuccessful, you have less of an
(20:20):
incentive to change lanes.
Whereas, if something radicalhappens like you lose your
job...
To me, the prototypical exampleof this, and one of my favorite
business stories is when SteveJobs returned to Apple at the
end of the 1990s.
(20:42):
And as I recall, the company waslike ninety days from going
bankrupt.
Like, they literally wererunning outta cash, right?
And one of his first moves wasto pare down their product
portfolio, radically.
And there's a whole story aroundthe four by four matrix, which
we're not going to go into.
But basically, he made this fourby four matrix and he said,"Any
(21:03):
products that don't fit intothis very simple construct are
going to be excised." And it wasa really painful move.
There's a YouTube video of Jobsat a developer conference at the
time defending his decision tocut one of the core technologies
of the Mac at the time.
(21:24):
Very hostile audience, right?
These developers have builtproducts based on these
frameworks and Jobs is sayingthis has no future.
But his point was, if we don'tmake a change now, there simply
will not be a company anymore.
And he was right about that.
But I think it was easier to dobecause they were facing such
(21:48):
extreme circumstances.
It was not Kodak with this nicerevenue stream coming from
selling film and chemicals.
Harry (21:58):
Yeah, I think we need better mechanisms for evaluating
what is at the bottom of ourlist and being not only true to
ourselves, but true to whatwe're trying to accomplish such
(22:18):
that we're not deceivingourselves into thinking that we
can have everything.
Jorge (22:25):
If only someone had written a book about priorities.
Harry (22:31):
I'm glad you brought that up.
But the thing that's making mecrazy right now in my work is
that they're reading the bookand they're still doing the
thing, right?
They're still not drawing thecut line at the bottom, and
that's what's vexing me rightnow.
They're getting the part wherethis is what's most important,
(22:52):
but what they're not getting iswhat is at risk of if they don't
stop with the crazy, with withthe chaos.
So, the book's not enough.
And interestingly, the bookdidn't ship with its final
chapter.
I've been working on it slowly,and that chapter was really
(23:16):
on...
I call it From Thought toAction.
It's really on fromprioritization to execution,
because that transition rightthere is the place that this is
happening.
Understanding what's mostimportant is only half of the
equation, but then figuring outhow to...
(23:38):
whether it's resourceallocation, whether it is driven
by some other set of criteria,figuring out where that cut line
is gonna go and figuring outwhat's gonna have to stop in
order for the world that youwant to have to materialize in a
much more predictable, much moreconsistent way.
(23:59):
We need some better tools andI'm certainly thinking about it,
but I wanted bring it up.
Jorge (24:06):
In our previous conversation, we talked about
framing and mental models, andI'm wondering if that might not
be the missing ingredient.
The idea that,"Oh, you have todig a bit deeper to what are the
mental models that are informingmy worldview at the moment?"
Because if I think of myself asan information you brought up
(24:26):
the label, right?
information architect I've beenattached to that label to
describe what I do for coming onthree decades now and...
Harry (24:38):
You look pretty good still.
Jorge (24:39):
Thank you for that.
But there's this question aboutwhy you're doing that.
are you doing it as a favor forothers to make it easier to
interact with you or are yousold internally on the idea that
is who you are.
I think that those are verydifferent scenarios and they all
rest on a particular mentalmodel.
(25:00):
Like, I'm always going to be aninformation architect in the
sense that I'm always thinkingabout, first of all, the role of
information in our lives, andsecond of all, the understanding
that you can be intentionalabout how you structure
information, and that has animpact on outcomes.
That's always going to be trueabout me, no matter what I call
(25:21):
myself or my work.
Harry (25:22):
Yeah.
Jorge (25:24):
But I don't want to become attached to labels,
particularly as I describemyself to the external world,
because I don't want to fallinto the trap of...
imagine if Jobs had come back toApple and been attached to that
particular API and the myriadother things that they were
doing.
That's not what Apple was about.
(25:45):
They needed to whittle it downto, what is the essence of this
thing and how can we moveforward in a new way, in a new
kind of reconfigured way?
And you're the expert here,obviously, but I suspect that if
you haven't sorted out thesedeeper mental model issues, it's
really hard to prioritizeeffectively.
Harry (26:09):
I think you're onto something here.
I think that's exactly right.
And you mentioned the wordfiguring out what this thing is
about.
That was almost verbatim.
And really understandingsomething's aboutness is, I
think, a result of lookingthrough a frame.
And that, to me, is a very richterritory that we should explore
(26:33):
at some point as a futureconversation.
Jorge (26:36):
It feels like we should put a pin on that and return to
it at some point.
Harry (26:40):
Oh man, this has been a good set of conversations
conversation, the one before it,I so appreciate.
It's left me definitely thinkingabout stuff in a new, in a fresh
way.
Jorge (26:54):
And I'd love to read the unpublished chapter of the book.
Harry (26:58):
It's getting there.
I'm going to send something outfirst on collapsing sliding
windows.
It's a new planning construct.
And I'll send that out to myemail list first and then I'll,
you're on that list.
Jorge (27:15):
Can we talk about that for just a second?
And I realize that we're runninga bit long here, but you do have
a new mailing list.
Is that true?
Harry (27:23):
I have one, but I haven't been using it.
I'm a terrible person.
But people have been writing meand saying,"Hey, do you have an
email list or do you have anewsletter?" And I'm like,"Yeah,
I'll put you on the list." And Ifinally have enough stuff to
start talking to people.
So I wanna let people know aboutour podcast.
I wanna let people know aboutlike this planning construct
I've been working on with LukeHolman.
Jorge (27:44):
Where can folks sign up for your mailing list?
Harry (27:47):
Ah, that's at harrymax.com or they can go to
LinkedIn and send me a note.
But harrymax.com, there's a linkright there.
And love to hear from folks.
Thank you.
Jorge (28:00):
Fabulous, Harry.
As always, brilliant talkingwith you.
Harry (28:05):
Great.
Great talking to you, Jorge.
Narrator (28:09):
Thank you for listening to Traction Heroes
with Harry Max and Jorge Arango.
Check out the show notes attractionheroes.com and if you
enjoyed the show, please leaveus a rating in Apple's podcasts
app.
Thanks.
I'm seeing it in every corporate environment that I'm
in (00:03):
leaders and boards that just don't know how to say,"Stop."
They don't know how to say,"Putthe brakes on this." And they
just keep piling on and what'shappening is not what they want.
Narrator (00:24):
You're listening to Traction Heroes.
Digging In to Get Results withHarry Max and Jorge Arango.
Harry (00:35):
Jorge, it is a pleasure to see you again, my friend.
Jorge (00:38):
Hey Harry, always good to see you.
Harry (00:40):
I just feel so grateful to know you're in my life and
that we have these conversationsset up.
It is super fun.
Jorge (00:48):
For sure.
I always think it's a little bitselfish of me.
We're releasing them and I hopethat people are getting value
out of them as well, but even ifthey don't, I'm getting so much
value out of our periodicconversations.
Harry (01:04):
Yeah, I agree.
I don't know that I could put myfinger on any specific change,
but I know that my overallapproach to moving through my
days has shifted a little bit.
I'm a little bit more thoughtfulbecause I feel like I've got new
tools and lenses to try on andreflect on as I move through my
(01:29):
life.
I brought something I wantedtoday.
It's really short and I stumbledon it, but it just, it hit right
at the center of the kinds ofthings that I think we
appreciate talking about mightbe useful for folks.
(01:50):
Can I just dive in or...?
Jorge (01:51):
Let's do it.
Harry (01:53):
All right, here you go.
"When you feel a path you'vechosen has reached its
conclusion, whether that's ajob, a relationship or a hobby
that no longer excites orchallenges you, it can be
tempting to put off ending whatyou've stuck with for so long.
But in doing so, we miss thechance to reinvent ourselves to
(02:16):
live fully as we cycle throughlife's seasons."
Jorge (02:23):
Oh, that is short.
Wow.
That is touching all sorts ofnerves on me.
You and I had a conversationlast year, I think, right before
I wrapped up my previous podcastand we decided to spin up this
one, right?
And it hinged on this subject,this idea that there comes a
(02:46):
time when you have to recognizethat something has run its
course and there is such a thingas inertia.
And I am someone who suffersfrom sticking with things for
too long after they've clearlyrun their course.
And I feel like it's cost meopportunities in my life.
So maybe we can unpack that.
(03:08):
What book is this?
Harry (03:10):
All right.
The title of this book is WhatWould Harry Do?
Lessons For Living Like A Herofrom the Wizarding World of
Harry Potter by Juliana Sharaf.
And I got this book while I wasout and about.
It just made me laugh when Ipicked it up.
And then, I was reading throughit and caught that and it
(03:32):
reminded me, I think, of myeither 2017 or 2018 book of the
year, which was NecessaryEndings by Dr.
Henry Cloud.
And I may have recommended thatto you at some point.
But that's a book about thinkingabout if, whether, and how to
(03:54):
end things.
And it is so critical,especially when it comes to
innovating, when it comes toproject management, when it
comes to prioritization.
Because I think most of usreally struggle with the sunk
(04:16):
cost of the time we've put intosomething or the money that
we've put into something, or theemotional investment we've put
into something.
It's really hard to stop.
Jorge (04:30):
The identity, right?
Because we build identitiesaround our careers.
Harry (04:34):
Yeah.
Jorge (04:36):
It's,"Oh, if I stop doing this and I start doing that,
does that mean I am no longer afill in the blank, job
description or whatever." Yeah,totally, I hear you.
I'm, super, super curious aboutwhat, first of all, when you
said what would Harry do, myfirst thought was like, wait a
(05:00):
second, did Harry write a newbook and I not know about this?
I thought you were the Harryalluded to in the title.
So I'm very curious about whatcontext this comes in the
wizarding world.
Harry (05:14):
Oh, interesting.
It's Don't Be a Phoenix was thechapter, and this was,"When it
comes to reinventing ourselves,muggles can learn a lot from the
mythical birds that are nostrangers to living, dying, and
living again."
Jorge (05:30):
But it said, Don't Be a Phoenix?
Harry (05:33):
Oh, I completely misread that.
It's Be a Phoenix.
Jorge (05:39):
Okay.
Yeah, that makes more sense.
Interesting.
I have fond memories of thefirst three Harry Potter books
because I read them to my kids.
But, we didn't read past thethird one for reasons that we
could go into if you want.
But I think that the Phoenix, ifI'm not mistaken, might be one
(06:02):
of the ones I didn't read.
So I don't remember what contextthat comes in.
But that's really interesting,this mythological image of the
phoenix, it obviously precedesHarry Potter and it's a powerful
one, right?
Like this idea that a way ofbeing ends and it ends
(06:23):
spectacularly, in ashes and thenfrom the ashes, new life arises,
right?
That's the basic image.
And it's a glorious arising of anew life.
It's not just new life, it'sthis spectacular bird that comes
out of the ashes.
(06:44):
And that's a great image to havein mind for this.
Harry (06:48):
And it's so funny that when I misread the chapter
title, I think that's theinertia problem, right?
The Don't Be a Phoenix is Ithink the fear of what it would
mean to effectively disintegrateinto ashes.
And when I read Be a Phoenix, Ithink, I don't know why I
(07:11):
misread it, but I can't helpfrom, sometimes a cigar is just
a cigar.
I may be reading into it furtherthan that, but the idea that we
have to embrace the destructionbefore the creation and this
goes right back to Boyd and hisdestruction and creation
(07:34):
discussions as we've talkedabout before.
But the reason I think thiscaught my attention and the
reason Dr.
Henry Cloud's book on necessaryendings was so potent, has
really come into very sharprelief with the work that I'm
doing with one particularleader.
This is a Chief Product Officerwho's about to retire.
(07:59):
And so, I've been brought in tohelp create the conditions for
this leader's departure andtheir ability to hire somebody
new and have them come in and besuccessful.
But the most interesting thingin the process has been learning
about the incredibly...
(08:23):
I don't even know what to callit.
The founder of this company isso creative and so mercurial and
so optimistic, that the companyitself just doesn't have it in
their DNA to stop things.
They just keep adding things.
(08:48):
One would think that's abnormal,but in fact, as I reflect on it,
in every organization that I'vebeen in, and I talk about this
in my book as well, just alittle bit, but the idea that we
would figure out how to stopinvesting in something, whether
it's a direction that we're inin our careers or whether it's a
(09:09):
podcast as in the case of yourInformed Life that led to our
work together here.
And hopefully this will continueon for a long time.
But the idea that people don'tthink about the approach to
pruning and really beingintentional about where to clip
(09:32):
and how to increase thelikelihood that things will grow
in a more fruitful, morepositive, direction, is leading
to a lot of aberrant behavior inthe system.
It's constant piling on and notenough piling off.
And I like to think it's aboutprioritization, but that's not
(09:55):
it.
There's something going on herethat is, we don't yet have the
tools to face the commitmentsthat we've made that need to be
deprecated and need to bereevaluated in the face of new
(10:19):
ongoing opportunities, eithersolving problems or pursuing new
challenges.
Those are all great and andgood, but unless you add more
resources to go with them,unless you figure out how you're
gonna apply those resources, allyou're really doing is adding
noise to the system.
And so many people, especiallyright now and especially in the
(10:44):
face of what's going on with AI,need to be thinking very
carefully about where they'rebeing put to their highest and
best use, and need to do a lotless of the things that are not
really the most valuable, mostuseful applications of their
(11:04):
talents and intellect andspirits, time and energy.
And it is so deeply fundamental.
And maybe it's that we don'tknow how to say"No." I'm not
quite sure, but I think there'ssomething here, and I think we
need to talk about it.
And I guess I would love to hearfrom you, how do you stop doing
(11:29):
things or how do you reevaluatewhere you're placing your energy
and your time and your...
I mean, how do you stop so thatyou can make room for the new?
Jorge (11:41):
The first answer that comes to mind is"poorly." And I
think that's because I've longhad an image of myself as a
tenacious person.
Harry (11:53):
Huh.
Jorge (11:54):
I remember very vividly, when I was much, much younger,
an incident, where, my dad hadobserved me doing something, a
behavior over and over againuntil I actually got what I was
aiming for, and he told me thathe had been watching me and he
had been sitting with acolleague of his while I was
(12:16):
doing this, and he had told thiscolleague,"Look at how tenacious
he is." And that bit of feedbackstayed with me and said,"Yeah, I
am tenacious and I stick withthings." And that's become part
of my identity.
And that...
first of all, I'll say, I thinkthat it's positive to be
tenacious and to be persistentand to stick with things.
(12:38):
But I also think that's a reallyrisky position to be in because
you can stick with things pasttheir expiration date.
At which point, like you weresaying, you're no longer adding
value, right?
The risk is that you findyourself trapped going through
(12:59):
the motions just because it'sbecome comfortable to go through
the motions.
When I discontinued The InformedLife, I had set up a workflow
that allowed me to produceepisodes of the show in a
predictable manner.
I had a schedule, I had a wholepipeline of guests.
(13:19):
I had the whole machine set upright.
And, the easiest thing to do forme was to just keep going with
it.
And what led me to make thatshift was a growing realization
that it had played its course.
(13:40):
The thing that I was working onhad played its course.
I set out to do something, hadachieved that, and it was no
longer a) producing the...
not producing results, becauseit wasn't about producing
results so much as it was aboutfulfilling what it was set out
(14:04):
to do.
Like, it had already done whatit set out to do, and now it was
just like going through themotions.
So it was that realization,coupled with what you brought up
earlier, like this idea that weare clearly in a transitional
period where AI is changingeverything and this requires
focusing attention in differentdirections.
(14:27):
And this is, I think, the mostimportant piece of this.
I think you and I are of the agewhere we might be more
consciously aware of constraintsand limitations.
I'll speak for myself.
I'm more consciously aware ofconstraints and limitations than
I was when I was much younger.
(14:49):
When you're a young person, theworld feels like your oyster,
right?
And it's like you can doanything and you can do all of
it.
And as one grows older, in mycase I'll say, as a dad, a
husband, you acquire certainresponsibilities that impinge on
(15:10):
your time.
And you have to be moreselective about what you're
doing.
And all those things, I thinkyou pick up as you age and as
you gain more responsibilities.
I would imagine that yourclient, when you're in that
stage of life, if you areretiring from a role, you've had
(15:35):
some success.
And you've also accrued certainresponsibilities.
And you have to focus your timeand energy.
You have to be more consciousabout how many plates you set up
spinning because you only havecertain amount of time and
(15:58):
capability to keep the platesgoing.
Harry (16:02):
Yeah, it's funny.
I just reflected on aconversation I was having
yesterday with a friend whosaid,"I figured out how to avoid
doing certain things.
There are some things that," hesaid,"I have to finish.
I just have it in my, I think,that tenacious gene, right?
(16:24):
I have it as part of who I thinkof myself, as somebody who has
to finish things.
They start and so things thatare too complicated or I can't
see how I'm gonna finish'em, Ijust don't start'em."
Jorge (16:39):
The flip side of that is that some things can't prove
themselves out until they'vebeen tried for a while.
A podcast is not something thatyou do a couple of episodes of
and then achieve immediatesuccess.
You have to keep doing it for awhile before you know whether
the thing is producing results.
This brings up an idea that Ithink is highly related to this,
(17:03):
and it's almost become a clichein the business world, the
innovator's dilemma, right?
Harry (17:10):
Mm-hmm.
Jorge (17:10):
The idea that if the thing that you are talking about
doing is successful, it becomesreally hard for you to
discontinue it in favor ofsomething else.
And I think that theprototypical example there is
Kodak and the fact that theyinvented digital photography yet
went under because they wereaddicted to the profits
(17:33):
generated by the chemicalphotography stuff.
And, there's so much of that inthe world, right?
And it happens not just tocompanies, it happens to people.
Like, you keep doing the samething over and over again, and
if you achieve any level ofsuccess, it's really hard to
chuck that and start somethingdifferent.
But I think that if you don'tburn your identity down every
(17:55):
once in a while and take a freshcrack at it, you run the risk of
losing relevance and falling outof step with what the world
needs from you at the moment.
Harry (18:10):
I'm sure that's right.
I've spent my whole careeralways wanting to call myself
the thing that I used to do.
I started out as a tech writer,but I was doing information
architecture and I wanted tocall myself a tech writer'cause
we didn't have a name forinformation architecture at the
time.
And then I was an informationarchitect, but I was doing out
(18:30):
of box experience work, but Iwanted to call myself an
information architect,'causethere was, nobody was an OOBE
architect at the time, right?
Out-of-box experience architect.
And that's been going on foryears.
I don't even know what to callmyself anymore.
I'm not really a product leader.
I'm, I do a certain amount ofthat.
I'm not really a straight upexecutive coach.
I call myself a player coach,but even that doesn't make any
(18:51):
sense given the kind of workthat I do, because it's this
blended coaching and consultingkind of work.
And it's in the dynamics of thework that my contribution lives,
and putting a label on it andcalling it something fancy just
so I can feel better aboutmyself isn't the thing to do.
(19:15):
But this idea of figuring outhow to let go of things that are
not serving anymore, I wish Ihad done a lot of deep thinking
and came with a bunch of reallysmart thoughts on a good theory,
and said,"Here's how do it." Butthat's not what happened.
What happened is I read thisthing in What Would Harry Do?
(19:35):
I was like, this once again issuch an important topic, because
I'm seeing it in every corporateenvironment that I'm in: leaders
and boards that just don't knowhow to say,"Stop." They don't
know how to say,"Put the brakeson this." And they just keep
(19:55):
piling on and what's happeningis not what they want.
Jorge (20:00):
Something that came to mind while you were talking
about it is that it might beeasier to do when you're
confronting a situation oftrauma or urgency.
Like we were saying, if you'resuccessful, you have less of an
(20:20):
incentive to change lanes.
Whereas, if something radicalhappens like you lose your
job...
To me, the prototypical exampleof this, and one of my favorite
business stories is when SteveJobs returned to Apple at the
end of the 1990s.
(20:42):
And as I recall, the company waslike ninety days from going
bankrupt.
Like, they literally wererunning outta cash, right?
And one of his first moves wasto pare down their product
portfolio, radically.
And there's a whole story aroundthe four by four matrix, which
we're not going to go into.
But basically, he made this fourby four matrix and he said,"Any
(21:03):
products that don't fit intothis very simple construct are
going to be excised." And it wasa really painful move.
There's a YouTube video of Jobsat a developer conference at the
time defending his decision tocut one of the core technologies
of the Mac at the time.
(21:24):
Very hostile audience, right?
These developers have builtproducts based on these
frameworks and Jobs is sayingthis has no future.
But his point was, if we don'tmake a change now, there simply
will not be a company anymore.
And he was right about that.
But I think it was easier to dobecause they were facing such
(21:48):
extreme circumstances.
It was not Kodak with this nicerevenue stream coming from
selling film and chemicals.
Harry (21:58):
Yeah, I think we need better mechanisms for evaluating
what is at the bottom of ourlist and being not only true to
ourselves, but true to whatwe're trying to accomplish such
(22:18):
that we're not deceivingourselves into thinking that we
can have everything.
Jorge (22:25):
If only someone had written a book about priorities.
Harry (22:31):
I'm glad you brought that up.
But the thing that's making mecrazy right now in my work is
that they're reading the bookand they're still doing the
thing, right?
They're still not drawing thecut line at the bottom, and
that's what's vexing me rightnow.
They're getting the part wherethis is what's most important,
(22:52):
but what they're not getting iswhat is at risk of if they don't
stop with the crazy, with withthe chaos.
So, the book's not enough.
And interestingly, the bookdidn't ship with its final
chapter.
I've been working on it slowly,and that chapter was really
(23:16):
on...
I call it From Thought toAction.
It's really on fromprioritization to execution,
because that transition rightthere is the place that this is
happening.
Understanding what's mostimportant is only half of the
equation, but then figuring outhow to...
(23:38):
whether it's resourceallocation, whether it is driven
by some other set of criteria,figuring out where that cut line
is gonna go and figuring outwhat's gonna have to stop in
order for the world that youwant to have to materialize in a
much more predictable, much moreconsistent way.
(23:59):
We need some better tools andI'm certainly thinking about it,
but I wanted bring it up.
Jorge (24:06):
In our previous conversation, we talked about
framing and mental models, andI'm wondering if that might not
be the missing ingredient.
The idea that,"Oh, you have todig a bit deeper to what are the
mental models that are informingmy worldview at the moment?"
Because if I think of myself asan information you brought up
(24:26):
the label, right?
information architect I've beenattached to that label to
describe what I do for coming onthree decades now and...
Harry (24:38):
You look pretty good still.
Jorge (24:39):
Thank you for that.
But there's this question aboutwhy you're doing that.
are you doing it as a favor forothers to make it easier to
interact with you or are yousold internally on the idea that
is who you are.
I think that those are verydifferent scenarios and they all
rest on a particular mentalmodel.
(25:00):
Like, I'm always going to be aninformation architect in the
sense that I'm always thinkingabout, first of all, the role of
information in our lives, andsecond of all, the understanding
that you can be intentionalabout how you structure
information, and that has animpact on outcomes.
That's always going to be trueabout me, no matter what I call
(25:21):
myself or my work.
Harry (25:22):
Yeah.
Jorge (25:24):
But I don't want to become attached to labels,
particularly as I describemyself to the external world,
because I don't want to fallinto the trap of...
imagine if Jobs had come back toApple and been attached to that
particular API and the myriadother things that they were
doing.
That's not what Apple was about.
(25:45):
They needed to whittle it downto, what is the essence of this
thing and how can we moveforward in a new way, in a new
kind of reconfigured way?
And you're the expert here,obviously, but I suspect that if
you haven't sorted out thesedeeper mental model issues, it's
really hard to prioritizeeffectively.
Harry (26:09):
I think you're onto something here.
I think that's exactly right.
And you mentioned the wordfiguring out what this thing is
about.
That was almost verbatim.
And really understandingsomething's aboutness is, I
think, a result of lookingthrough a frame.
And that, to me, is a very richterritory that we should explore
(26:33):
at some point as a futureconversation.
Jorge (26:36):
It feels like we should put a pin on that and return to
it at some point.
Harry (26:40):
Oh man, this has been a good set of conversations
conversation, the one before it,I so appreciate.
It's left me definitely thinkingabout stuff in a new, in a fresh
way.
Jorge (26:54):
And I'd love to read the unpublished chapter of the book.
Harry (26:58):
It's getting there.
I'm going to send something outfirst on collapsing sliding
windows.
It's a new planning construct.
And I'll send that out to myemail list first and then I'll,
you're on that list.
Jorge (27:15):
Can we talk about that for just a second?
And I realize that we're runninga bit long here, but you do have
a new mailing list.
Is that true?
Harry (27:23):
I have one, but I haven't been using it.
I'm a terrible person.
But people have been writing meand saying,"Hey, do you have an
email list or do you have anewsletter?" And I'm like,"Yeah,
I'll put you on the list." And Ifinally have enough stuff to
start talking to people.
So I wanna let people know aboutour podcast.
I wanna let people know aboutlike this planning construct
I've been working on with LukeHolman.
Jorge (27:44):
Where can folks sign up for your mailing list?
Harry (27:47):
Ah, that's at harrymax.com or they can go to
LinkedIn and send me a note.
But harrymax.com, there's a linkright there.
And love to hear from folks.
Thank you.
Jorge (28:00):
Fabulous, Harry.
As always, brilliant talkingwith you.
Harry (28:05):
Great.
Great talking to you, Jorge.
Narrator (28:09):
Thank you for listening to Traction Heroes
with Harry Max and Jorge Arango.
Check out the show notes attractionheroes.com and if you
enjoyed the show, please leaveus a rating in Apple's podcasts
app.
Thanks.
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