S1E5: Navigating the Beautiful Mess with John Cutler

I'm learning by writing, which is something people need to
think about that I'm exploring these thoughts. I mean, I worry
about that all the time. I think about like, who am I to say
these things? I kind of see myself as like an on second
thought leader, like on second thought. That's my thing. Like,
anyone can do that. For me, the writing thing is like an
exploration and a journey. But it doesn't need to be like that
for everyone. Like they might want to get really deep into a
topic and write about I do think that writing is learning, you
know, writing is learning and exploring a particular idea. And
I think that people feel like this this high bar to do it
when really the bar is being curious about something enough
to throw yourself into it for a bit.
Hi, I'm Karl.
And I'm Danielle.
And this is productly speaking.
We're product managers by trade. And here we explore the world of
product management. It's people and their stories.
We promise to keep it entertaining. And maybe you'll
learn something. Shall we give this a go?
Let's do it.
On today's episode,
let's just get into it. Okay.
We had an icebreaker at work today asking like trying to get
the product managers and the engineering managers like more
friendly with each other because we're all remote and haven't
physically met before. And the icebreaker question was you have
zero time to prepare and you have to give a 20 minute
presentation. What do you choose to talk about? And most people
pick like interesting topics like one guy is struggling with
his house flooding. And so he's like, I would talk about flooding
mechanisms and how to stop it. Somebody else is training for a
marathon. So like I would talk about running shoes. And I'm
like, I would talk about product management. And they were all
laughing and they were like, well, you grocery shop like
surely you could talk about grocery shopping and then it's
not work related. And I'm like, everything comes back to product
management. Okay, look at an egg timer, for example, and think
how could that be an app or something that just works better
for the problem? I'm trying to think. It can't go grocery
shopping without the approach to many things. Yeah, that's the
thing. That's the problem. But that's also the joy.
John Cutler started as a game developer working on a game
called Last Call, a mass market CD-ROM bartending game. He then
went on to produce sales and marketing presentations at
Nickelodeon for MTV, Nickelodeon, Bravo, Comedy
Central, and Major League Baseball. His journey into
product management started at RichFX. And since then, he's
ventured into consulting, writing, and most recently has
held the title of Senior Director, Product Enablement at
Toast. John's blog, The Beautiful Mess has been going
for just over four years and is a highly regarded product
manager resource. I know both myself and Danielle have spent
many hours discussing articles written by John. And so we are
very excited to introduce to productly speaking, Mr. John
Cutler.
Great. Thanks for having me. The intro was good. I was living
in New York as a musician, did this game thing and was very
eclectic in my interests for a long time. What will help most
people get my background is for probably settled into this
series of B2B SaaS companies, and most notably at a company
called Amplitude where I would interact with companies from
around the world and lots of them. And that was probably
really informed my writing, inspired my writing, did some
UX research in their product management, and then this weird
product managerless role in Amplitude and then onto an
internal role at Toast. That's a bit about me, eclectic start in
product and then settled into B2B SaaS with some product
management and UX roles.
Excellent. Game development in a lot of ways is product
management without the title, especially when you're like the
lead over the thing. It says you've got to product manage a
game, at least I think you do. Tell us a little bit about your
experience building Last Call and how that helped you get from
game developer into product management.
I dropped out of school. It always kind of starts with
something funny like that. I mean, I had dropped out of
school, but that wasn't really the thing. I was living in New
York at the time, and I think I probably wanted to get a job.
And I said, how do you get a job as a bartender? And then I
realized you had to go to these weird schools that you could
find little classified ads at the back of the newspaper or
whatever called bartending schools. And so I thought, what
wouldn't it be great if there was this video game, you could
learn how to 10 bar and then you could do it. This was early,
early 2000s. Yeah, even 1999. I mean, this was like you ship
things on CD roms. It's crazy, as naive and as as quaint as
that sounds like you would ship things on these things. So I was
young. And then I was really young. And I just got excited
and enamored with this idea. I remember getting a credit card,
which is a dangerous thing to give someone in their early
20s and marching out to the like, you would get your
computer at sort of a Sears or something like that. So I
remember marching out and getting a compact computer like
this is going to be it, I'm gonna have this video game turned
out to be way, way harder than I thought. And luckily, I met a
couple people who really, really helped along the way. And we get
it started. And we got this thing going a friend who gave me
just a little bit of money, which helped out a lot in doing
this. And yet we sort of evolved this game. Some of the
funnier things about it is that actually there's a star studded
cast of characters in last call, Tina Fey actually did voices
for some of the characters. No way. And it's probably okay to
say this now, because I think she did it under a pseudonym
because it was like a non union gig. I think I shouldn't say
anyway, I think it's something like that. I'm probably wrong.
Actually, I'm not but I think it would be wrong. But but anyway,
she was she did some of the voices she played this really
raunchy nurse in the bar who was coming into the bar after work.
There's a guy named Adam Felber. He's in that show like wait,
wait, don't tell me and he's a host for NPR. So he did other
voices in this particular thing. And these this musician
Tina Fey starlight, who's really popular at the time. So she did
this other Tammy Fey starlight, not Tina Fey starlight. There
was all these people in New York and comedians and other people
we somehow roped into doing voices for this. Unfortunately,
that meant that the game was absolutely not safe for work.
And it got banned, not banned, but the game like the Walmart,
who said they were going to buy it and distribute it, decided
not to. Yeah. And at the time, it felt like well, they sell
guns, but like, why can't they sell this game, it really was
kind of over the top. You had to 10 bar for these 20 customers,
then you would like reach back as the god of wine at the end.
And it was just it was out there. There's like a S&M couple and
the nurse and then there was this hedgehog that came into the
bar and astrophysicist named smooth. So it was just over the
top. But it was a really, really, really fun experience
working with super talented people, animators learning how
to make this game. And it was hard to do and then no one they
couldn't distribute it. So luckily, at the time I
negotiated because they didn't think it was a good idea
negotiated the ability to sell my game myself directly from a
website. And they thought, well, how quaint, no one's gonna buy
that they're gonna just buy it in stores. That turned out to be
a good decision because we're able to recoup some of the
money back from doing that. So that's Yeah, that was this whole
adventure with making stuff with people. It was fun.
Very cool. So then you went on to work at Nickelodeon and that
kind of sounds like a dream job, especially at the time that you
were going to do that again to tell stories. How did that then
further help inform your move into product?
At the time, I was touring in a band and would come back into
New York occasionally. It's funny, I did a string of these
basically presentation gigs. And for sometimes at long periods
of time, like Nickelodeon was one that I did for a couple
years, when they had these large presentations. And so it was
sort of a quasi freelance thing that you come in when they would
do these big presentations. But I also worked in a PowerPoint
sweatshop, essentially an investment bank, we would work
the graveyard shift as musicians, it was mostly like
musicians and actors and other people and you'd go in to like
Morgan Stanley at 10pm at night and then work till six in the
morning. And this was during the dot com boom. But that was
actually before Yeah, around some overlapping time. And that
was pretty fun too, because you got to just get deeply entrenched
in business and reading all these presentations. And you had
to use two point font. Sometimes the goal was not for anyone to
read this stuff. It was actually just shock and awe investment
bank presentations. That was fun. But the Nickelodeon stuff
was so interesting, because I think I underestimate the degree
to which impacted how I view this part of the creative
process. So you're sort of producing and putting together
these big advertising up fronts that they would give and the
product is essentially something that the ad sales team or other
people are going to use to get all the brands really, really
excited for that year and so buy ads and things. And so it really
was kind of a product and and it was really difficult and
there's lots of stakeholders involved and they'd all have all
sorts of things and every year it was a new theme to put
together to do it. So although I would say probably my primary
interest at the time was playing music doing these and they
usually lasted about three to six months at a time for the
different brands at different times. That was really, really
interesting. And you learned a lot at the same time. So yeah, I
was still pretty lost at that point. Like I hadn't like fully
found tech and things and then slowly I started to get these
more sort of tech oriented jobs and PM jobs and things at the
time.
So you've already named Artina Faye. Did you get to meet
Keenan Thompson as part of that?
No, I didn't.
Disappointing.
Karl's been really keen to ask you that question.
No, I didn't.
You've mentioned amplitude and how that's inspired your
writing and gave you kind of that journey into design and PM
your blog, The Beautiful Mess is something that both Karl and I
have been receiving to our inboxes for over a year at this
point. And we spend a lot of time talking about it, as you
mentioned in the intro. How did you get started writing The
Beautiful Mess?
It starts in 2015. Beautiful Mess is actually only about a
third of my writing. I have more articles not in The Beautiful
Mess than in The Beautiful Mess. So I have Cuddle.Fish. It's all
the old posts. And so that started in about 2015. And so
Beautiful Mess was maybe 2019 or 2020. And so I have a good five
years of writing before then. And basically, I figured it out
the other day, I've written a post every 5.2 days since 2015.
So The Beautiful Mess was sort of the culmination of just a
writing habit. And it predated amplitude and it probably
actually helped get that job, that prior blog. And I would
write this post like 12 signs are working in a feature
factory. And I was an OG product clickbait content creator
before this space was dominated by other people. Yeah, I was
really active on Twitter there. And I was sharing these images
and drawings and stuff. I used to do that a lot. It's a
writing habit that started earlier. Actually, I was
working at a company in Raleigh at the time called Pendo. And I
was there, sort of we're doing this bi-coastal thing with my
partner Sharon, and I had a lot of time on my hands. So I would
just go to a coffee shop in Raleigh and just sort of start
cranking out these posts. And that's really where I started
coffee shop in Raleigh. It was called Raleigh raw, I think.
Yeah, just bar and they had this coffee that had like
buffalo milk in it or something like that, like buffalo oil, or
no grass fed beef, something. And they put that in the coffee
was very good. Well, it's something like that. Yeah,
something like that. Addition to coffee. I don't know exactly
what it is.
Yeah, it's supposed to like help you get more energy or
something. There's a whole
Oh, it worked. Yeah, that started my writing career yet.
The amplitude stuff definitely deepened the awareness of a
bunch of other companies though, because I was meeting with new
companies all the time. And that gave me a lot of inspiration
as well.
Very cool. So how much do you know about your audience, your
reading audience? Are they all product managers seeking to
learn? Or do you have people from a variety of different
disciplines?
It's a variety of different disciplines. And it's a variety
of different types of people. It's one thing I've learned a
lot in product and writing. It's like any company, like you can
have an overlap of people who want to use sticky notes, like
for example, in Miro, it doesn't mean all of them are using it
for the same thing or the same types of people. I mean, my
stuff tends to be a little bit more introspective. I don't do
actionable. That's not my thing. I'm not actionable in a lot of
the posts. I mean, I think some of them I do. And I'm like, Oh,
I'm going to just I have this framework, although I've
developed a number of interesting frameworks over the
years, or at least help teach them. It's not something I write
about all the time. So I think it tends to be pretty
cross disciplinary with a fair amount of engineering managers
and leaders and design leaders. And it seems like what's in
common with folks is a desire to go like a one or two layers
deeper into the patterns that they see at their work or with
their products. I asked on LinkedIn once what's cutler as
a service? Like what job to be done? Am I doing or like what's
that thing? And then I think a couple people said, you know,
making us think or something. So that that's the the beautiful
mess was definitely about leaning into this idea that it's
this just messy reality that we have to tackle and there's no
clear, simple answers for most things. I think that's the
audience. It's tough, because that could bring in a lot of
diverse people as well.
So how have your interactions with readers shaped your product
career?
It's gonna sound basic, I guess, but like they remind me that
there's other people out there like me. I mean, that was the
thing is I was sort of writing and then I was learning more
and more people would reach out and say, well, that resonated
and then I start talking to them more. It's given me awareness
that there's a large diversity of folks that we're working
with. And one thing I've been thinking a lot about too, that
definitely the writing has helped with is we tend to think
about I don't know if you've ever taken those personality
tests where someone says, you know, are you strategic? Or do
you collaborate? Or do you do these things? And I think one
thing that the writing has helped me with is you can have
people who are collaborative, but who have different views on
work and worldviews and professional views who treat that
very differently. You know, someone from Silicon Valley,
when you say collaborate, is going to view that maybe in a
different way than someone from, you know, Denmark or
something, they're just going to view it in different ways. So
I think if anything, the writing and interacting with
readers has reminded me over and over that you're dealing with a
pretty diverse bunch, not just in terms of work styles, but
you're dealing with a pretty diverse bunch and just in terms
of worldviews and views on how to get things done, that kind of
stuff. So that's where I think I've expanded the most in
interactions with readers.
You mentioned that you started The Beautiful Mess in 2019, but
you've been writing much longer than that. What have your
employers along the way thought of the blog? Has it helped your
career path?
They hate it.
Oh, really? Wow.
I mean, there's always been this tension because, I mean, I tell
this joke a lot, because I think it's just funny is that I think
I remember Spencer from Amplitude was like, why did you
write that? And I had to remind him that his problems were not
unique. You know, that like someone else had that exact
problem. And so you know, it's always been a little tenuous.
But then again, at my latest job at Toast, I think it was
great because I would get messages like, you know, thank
you so much for doing that writing. I know it's outside of
work. I know it's not really related to us, but it resonated
on some level. So it's definitely a balancing act. I
wish there was a way to solve this problem. Like there should
be a product out there to do it. Because I think this
relationship people have with their current employer causes a
lot of people to share overly generic things. And maybe I
fall into this trap where they don't feel like they can talk
about specifics, unless their company happens to be a company
that welcomes people talking about specifics. And what that
means is we have this sort of Instagram version of product
management. I was talking to someone recently, for example,
from Stripe, and they just were laughing. They're like, you
should just see what it's like the inside of this place. I
could have inserted any company with Stripe, Google or Amazon,
you know, just any of these famous companies. And so I think
that one thing that that does is, you know, this tightrope walk
that I have to balance sometimes with my writing is probably
something other people have to balance and how they
communicate about work. But I think ultimately, it means we
don't get as many real world stories. And you have to use
words like companies that or in some companies or often, and I
get it, I understand why people do that. But it also means that
we don't hear as much about what's actually happening in
companies, because people need to balance that in their work.
Yeah, we've noticed that just you're reading some of the big
stories out of product leaders and people that are big in the
space, they'll tell a great story and you come away from it
and you're like, that was really interesting. But at the end of
the day, there's no way the story was the entire story or
that it completely represented reality.
You almost need multiple people to tell the story for that,
which is the main thing.
Having worked in Silicon Valley for a few years and really
seeing how before I moved to California, so many of these
companies, you mentioned them, the Amazons, the Googles, the
Microsofts, they're all called out as leaders in their space
for product management. And then you start working for one of
them. And you think, well, actually, the six pager only
works in a very specific use case or in a very specific way
when you're then a startup being a product manager thinking,
yeah, I can do a six pager and everything's going to be
perfect. And it just isn't.
It's interesting how we process that because I think success
maybe is a function of context across multiple dimensions like
context across aptitude and experience and competencies and
things like that. And then the tools we use of which frameworks
are a tool. They're just one tool in the tool belt, right?
And then across our practices and behaviors and then across our
environment and how it's shaped and then across the beliefs and
norms of a particular company. And all of that then has this
sort of contextual pivot to all those things. So context across
many factors across the stage of the company, where the company's
located, where the employees and all of those two, all things are
intertwined, right? You need competencies to use certain
tools, but tools let you do certain things. And we shape our
environment and our environment shapes us and on and on. It's
something I'm very, very interested in. But I think the
meta discussion there, if you were to call it that is we have
a hard time just teasing that out for anything. You know,
you're in this environment, you're doing it. And it's kind
of hard to distinguish between what a skill is and a tool. And
it's hard to distinguish between sometimes what an environment
does to the people in it and then how people shape it. So I
think that it's just an it's a fascinating topic. I think for a
lot of people, it's pretty tough out there in some ways. It's a
challenging environment. In some sense, people want
certainty and simplicity at the moment. They want someone to say
that's good. That's bad. It is very contextual.
So our experience is that many career ladders for PMs require
that you prove that you have your craft nailed and especially
externally, whether that be podcasts or blogs or showing up
at meetups and giving presentations like you get
internally rewarded with promotions when you're seen to
be doing things externally, we've already talked about how
that can be problematic. But as a subject, how do you feel about
that in terms of career progression? And is that
relevant proof that you're growing your skill?
As someone who's worked with managers to put together a
career ladder for PMs, I think that there's a tendency to fall
into some traps. And one of the traps is basically someone will
say they need to have impact. And then they'll say, well,
what kind of impact? And then the first person will say, well,
they need to impact the people around them. And another person
in the room will say, well, they need to they need to impact the
community. And then the next person will say, well, they've
got to impact the product and we're going to have outcomes. And
then they end up with like a fairly sort of over generalized
model. And it just ends up in a career ladder. And then without
people really giving it any critical thought, they're
returning to that career ladder all the time. And it makes sense.
It's the same thing when people come up with maturity models,
like most maturity models in the world are not well thought
through. They get a couple of people who've done something and
they say, what does terrible look like? And they put that on
the left and number one, and then like, what does amazing
look like? They put that all the right number five, and this was
like, well, let's just extrapolate everything in
between. And let's just come up with a couple dimensions and do
it. My first response when you said that is it just feels like
lazy career job design. Yeah, frankly. And I mean that
because there are amazing PMs who choose not to engage have a
life and engage in their work and do an amazing job. And then
there's people who are outwardly focused in the company, but do
that on the company's dime. Yeah, when they should be
getting some work done. When I see these folks, you know, and
sometimes I've been included in this, you know, kind of on
LinkedIn with some great thought leadership or whatever, I have
to ask and I would ask myself, like, are you getting your job
done? I'm sure people ask that about me in the company. So I
tend to advocate for more nuanced things. Like I think
that if someone, especially if you're at a company that doesn't
sell anything related to the product community, your best
reason to engage in the product community is probably to create
an environment where you can hire people, and then also keep
your own skills up to date. So I think that that I can understand
the rationale behind it, but I'm always a little skeptical with
job ladders that take a very biased view to what success
looks like. But that's just me. I think you've triggered a
thought there of saying on a job description that you have to
have external impact loses the problem that you're trying to
solve for. Are you trying to solve for hiring? Are you trying
to solve for skills gap closing?
Yeah. And I think I mean, that's like so many things in
product. Look, how funny is it? Product managers talk all the
time about iteration and learning and research and blah
and blah and empathy and this and that and all these things.
And then they don't turn any of that to their internal, you
know what I mean? It's just, yeah, let's go deep down the
rabbit hole around this. And then how are we going to do
career ladder, blah, blah, blah, blah, blah, like they don't ask
what's the job to be done? What's the why before doing it? So
it's just designers to I mean, it's all like, it's we're all
hypocrites in that level.
So when you started to work on establishing yourself in the
product industry, you know, through your writing and
through your thought leadership on places like LinkedIn, etc.
Did you come up against any resistance in the community?
No, I mean, sometimes you have just resistance based on people
just not liking I mean, there's some people who just want
actionable things. And that's the only resistance. The
resistance is the market, I guess. Because some people
don't want that stuff. Frankly, that's also a fair amount of
privilege involved with that. And it's also starting really
early in this. I can't imagine right now in this sort of
narrative soup that's going on and all these content creators
and all these canvases and everyone like plugging into AI
anything and writing all this stuff, what would someone who
had a genuine message do to cut through all that noise? And so
I don't worry as much for me. It's what I do. And I have a
really good head start for doing it. But even then, like
LinkedIn algorithm is terrible. I mean, this thing is just like
it's almost doom scrolling like LinkedIn is the new doom
scrolling. It's either people have lost their job, or they're
pitching some stupid framework or whatever. And I think that
there's work to be done there to get genuine voices. I think
also the pandemic at a certain point, it overdosed us on talks
and and content coming in from the community. There are a lot
of vendors in that space of which I was with one and
everyone was getting a lot of talks going. And then it's sort
of the tail end of the pandemic. Well, I still think it's going
in some ways some places, but I think people have been become
overloaded. But what I mean from that is I think someone trying
to start doing what they're doing now and share this stuff
in authentic wouldn't have anywhere near the easy time that
I had with it when it was fairly greenfield that people were
doing this on various platforms. So
yeah, that's just the typical challenge of trying to join an
already crowded market and trying to stand out when you've
got people that already have their preferred vendor of
content that they're going to.
Well, that is it. And there's just a lot of money to be made
with clickbait. There's a lot of money to be made with being
divisive. And there's a lot of money made to sell people in
security. Yeah, with a lot of this. And that makes it very,
very I mean, I'm sure it's always been like that, but it's
very crowded market. So it's supply and demand here. Remember
to select I do think that if there weren't those things,
people would find more authentic content and doing this, but
there's a lot of incentives to have not very helpful content
out there on many levels. So I think that that contributes as
well.
Yeah, that's an interesting point. And yeah, LinkedIn has
definitely become a doom scroll of just seeing how many people
have gotten laid off, you know, companies left and right are
laying people off as they're recovering from basically
pandemic over hiring, and just also, you know, wanting to get
the books as clean as possible, especially if you're publicly
traded to get as much of an advantage as they can there.
It's also become a lot of people telling you who you should be
and who you shouldn't be and telling that things are dead or
not dead. I mean, imagine in these times, people are saying
these people don't need to exist. And then they also use
language like I hate to break it to you, or this is going to be
hard to hear. Who are these people that have the sorry to
get like I'm passionate about this, but like who wakes up in
the morning and says, I'm going to tell 100,000 people some
hard news and expect that to be okay. But some people are like
that. You know, like, you know what I mean? Like that doesn't
show a lot of empathy to people's situations. And so
there's a lot of that too, which I don't like.
No, but in a lot of cases, that same person has the solution
that they're ready to sell you a few days later. Well, yeah,
sometime or right there in that post. That's the environment
we're in. And it's, it's unfortunate. But I also think
there's opportunities for genuine interactions with
people. And I really I think that that's great. Yeah, no,
that is you put your mind to it. And so you've recently
written a piece called self gaslighting and the doubt loop
in which you talk about imposter syndrome without once mentioning
that phrase. So congratulations on figuring out how to do that.
Because that's a pretty cool writer's trick. But you state in
that article, at a certain point, you start to doubt your
overall ability, maybe I deserve this situation, maybe anywhere
that would hire me is like this, we stop asking whether having a
different manager might help us be more successful, or if
working at another company or on another team could be a better
fit, we stop asking if we were genuinely fulfilled, we accept
things as they are, because we believe we're the problem, or
are incapable of dealing with the problem. Before you know it,
your options are limited, and your career narrative becomes a
self reinforcing loop of stagnation and self doubt, you
can get to the point where nothing feels real, and you're
self gaslighting. That's a really powerful observation.
And really, that resonated a lot with me. It's one I think that
we find ourselves wrestling with often in product management to
the people that find themselves in that situation, what would
you recommend? And it kind of goes back to what we're talking
about the whole doom scroll of LinkedIn, because that can get
you into that spot, too.
Yeah, that's a heavy topic area. As cliché as it sounds,
awareness in trying to catch that stuff early is probably
important. And this does tie into what we were talking about
in the sense that there's a lot of, especially here in the
United States, and people writing from in the United
States, or within Silicon Valley, or in tech in the
United States, there, it's almost like there's, I don't
know, there's just this like leadership industrial complex,
there's almost this insistence that it's this almost toxic
stoicism, it's weird, like, bite your lip, don't complain,
it's just you, you can self improve your way out of it all
the time, at least for me, once I've started noticing that, and
noticing the effect it would have on me, and the effect that
it has on other people, that there's always a way you can
blame yourself for something. And it's funny, because a lot of
this dominant narrative is stop blaming other people. But I
think that the problem is way tilted in the other direction. I
think that people are often blaming themselves for these
situations or blaming these things. So I think that
awareness that you could be doing is the first thing, I
think that the second thing is building a support network that
maybe isn't just people at your work, or people in your team,
you know, building people who can give you a perspective, it
really helps in that, because you find people in these
situations at work saying, Oh, I could be a better communicator,
I can better manage up or whatever. And then you talk to
a friend, and they're like, that is just certifiably toxic. And
so you need a friend to remind you of those particular things.
And I think the third thing, of course, I would have a third
thing, because you're supposed to speak in threes all the time.
It's like the Holy Trinity, is I think that there is a level of
discovering what you really care about. And I think that often
in people's careers, and especially in this space, it's
so bombarded with people telling you what you should care about,
and telling you what amazing should look like and telling you
all these things that I think sometimes we forget, like what
our place of happiness is, you know, like, what joy do we find
in this particular thing? And why are we doing it? And
especially when you're really into product, it can sort of
overwhelm your life, you know, you finish work, and you're just
like, well, I guess I could catch up on some of this cool
stuff. And it tends to put so much of yourself identity is
linked into a sort of more broad professional bucket than
discovering what you like about it. It's okay to have fun
doing this. It's okay to have fun. It doesn't need to be this
big, you know, Shakespearean drama all the time about it's
hard, and you won't like this and high agency and blah, blah,
blah, blah, blah. It doesn't need to be like that if you
don't want it to be like that. And so I think that that's
important for people to remember.
I do think it's, it's easy to lose yourself in the drama
sometimes. And whether that's social media driven drama,
whether that's workplace drama, I really appreciate the call
out of having a support network or somebody that you can trust
that sits outside of those bubbles to check you, you think
can be super important for the people that don't have that and
maybe want to be that for themselves. I mean, I love the
call out, you've said that your blog is more about being
introspective, you're almost checking yourself by writing and
getting these thoughts out of your head to check yourself. How
do you find new topics every week and the confidence to get
out of your own way and be the subject matter expert that can
talk on these things week after week?
Oh,
it's hard. I mean, I'm learning by writing, which is something
people need to think about that I'm exploring these thoughts. I
mean, I worry about that all the time. I think about like, Who
am I to say these things? I kind of see myself as like an on
second thought leader, like on second thought, that's my thing.
Anyone can do that. For me, the writing thing is like an
exploration in a journey. But it doesn't need to be like that for
everyone. Like they might want to get really deep into a topic
and write about I do think that writing is learning, you know,
writing is learning and exploring a particular idea. And
I think that people feel like this this high bar to do it when
really the bar is being curious about something enough to throw
yourself into it for a bit. And that I guess, has been how I've
surmounted. See, now you got me thinking about I'm going to be
nervous about the next time I write, write what you know,
write what you've experienced, be authentic to your thoughts,
caveat the stuff you've written. That's how kind of I do it. If
I don't know a lot about something or it's new to me, I'm
pretty open about that. Those are the things that come to
mind when you're doing it. And if possible, figure out how to
share real stories. Like if you can get to that point where it's
like, this is how we solved a problem. And this is what we
did. And you can arrange that it can be amazing. And in fact, I
would say that that's something any company could do to even
improve how they work. If you can get over the hurdle with the
legal team about how to share things that you're working, it a
forces you to think about it, be it helps with recruiting
amazingly, people love companies that are willing to write about
how they work in in ways that are authentic, not just so
obviously massaged around what they're doing. And I think that
from that perspective, the writing also helps you as a
team, it's one thing to do a retro and say, oh, you know, we
don't communicate. And let's just ignore that for the next two
weeks. Writing and packaging your learnings can be really
helpful. So maybe you can even find a community of folks
internally who want to write even if it's an internal blog,
that could be a good way to start kind of getting the engine
going with a group of people. Maybe it's a little easier to
cross that hurdle than releasing stuff to the public for everyone.
You said that you write one article, we've averaged one
article every 5.2 days. And at this stage, it's it's a habit.
How long did it take you to build that habit? Or did it just
come supernaturally to you?
I don't know, maybe 10 times. I don't know what it was like in
the beginning. I mean, I think I just did a lot in the beginning.
So then it just sort of started to work out like that. I
definitely feel it, you know, if it's been about four or five
days, I start with like, Oh, I better try to get this post.
Sometimes I write two of them in a week, you know, and then I
buy myself a little bit of time. I did do these funny things
that anyone can do initially to get over some of the hurdles of
writing. So there is a product called flow state, I think it's
called flow state or flow app. And you can find it on the
Apple Store. I don't think it's been updated for years, but it
was great. So basically, you start writing. And if you stop
writing, everything disappears, you have about three seconds of
stopping writing, it would disappear. Wow. And so I would
start out by doing that for like a minute. And then I worked up
to three minutes, and then five minutes. And then I got to the
point where I could do it for 60 minutes, like a flow state. And
so 60 minutes of writing at that speed, you know, is like 6000. I
mean, it's a lot of words, it's lots and lots of words, it's
sort of books full of words. And so that was practice. But it
actually taught me an amazing lesson about writing, which
everyone talks about, but putting in practice is a lot
harder, which is, you know, I think someone said recently on
Substack, write from your heart and edit with your mind, there
is that idea, I don't know who said that original quote, but I
saw them share it, maybe they wrote it, it was just a very
interesting way to put it that that app, you know, kind of
disconnecting your mind and writing from your heart about
what you were exploring can be really good practice for doing
that. And so I think that once you know, you do that for a
while, you build the confidence that there's a post in there
somewhere, you just got to you just got to start typing. It's
in there.
That quote feels like the safe for work version of I think it's
Hemingway, who said, write drunk, edit sober.
Oh, there you go. Yeah.
You've got four years of content on the beautiful mess. You've
got many more years on cuddle that fish. What haven't you
talked about yet that you're excited to get into next?
I want to do a deep dive on the finance product overlap, because
I think that that's one of the biggest catalysts to get this
whole thing going. And we don't talk about it enough, which is
basically like at the end of the day, your company strategy is
your budget. It's not the it's not really the strategy, but the
main implicit beliefs get manifest often as a budget. And
so you see teams, for example, come up with amazing strategy.
And then, you know, if you're in an early stage startup, you know,
exactly what I'm talking about. And then, you know, some
investor or board member happens to meet one of the founders over
coffee one day, and gives them an idea. And then suddenly, it's
this thing, and they've spent money on it, and they've invested
some money, and they've kind of locked in money for something.
And then you have to do it, no matter what, what the strategy
is, you know, it's sort of what you've budgeted and what you've
done. So I think that that's like a very interesting overlap.
It could I think it explains why also a lot of these companies
want desperately to be more product focused, but can't just
get the machinery going. I might do a deep dive on that, where
maybe I interview, you know, 50 people or something, and then
kind of write a better series on that, because I think that
that's something important. I like a change of pace, you know,
like talking about dollars and cents would be really interesting
at the moment.
So how do you continue to find these new topics? I mean, where
do you get your inspiration?
Oh, geez, I mean, there's never ending topics. I mean, these
things, I think I remember an amplitude once we tried to map
out all the various topics that could exist. And it was, you
know, thousands and thousands of I think I wrote one time, you
know, 200 titles that we could just write right now that hadn't
been written, it was just a very diverse topic area. And I have
these also these just massive mural boards of ideas, and I
just can go to them. If ever I'm weak on an idea, I just go
to the big mural boards that I write, and I'm just like, well,
let's go down into topic land. All these are topics that I'm,
you know, I happen to be sharing my screen now at the moment, no
one can see that who's watching. But I'm just showing topics
after topics after topics after topics, topics after topics
after topics. At this rate, I can't write all of them. I'll
definitely retire or be sitting, I don't know, as a grandparent,
assuming my son who's six self motivates in certain
directions. But you might not, you know, world might be burning
by that point. So
I think that's a great segue into our final question, which
I'll let Danielle ask.
Yeah, it's a perfect segue. And then you also mentioned earlier,
where is your place of happiness? So the final question is just
to get to know our guests a little more, if you could wake
up any place tomorrow, where would you choose to go with the
day or spend the day?
Wow. Remember, Danielle said something before we started that
she didn't experiment with her work. And they all asked a
somewhat similar question. She said, talk about product
management. But she said that I'm going to try to think of a
non work example. I mean, pardon me, my first instinct was like,
Oh, my God, I'd be doing this amazing workshop with a great
group of people. Maybe that is my gut answer. Maybe that's I
found my my happy path or like my I don't know my red thread. I
would do nothing. I just want to maybe right now I'm inclined to
just wake up on a beach and do nothing for a day. That would be
good that like nothing in particular just just a day,
especially not having to think about product. Yeah, I would
find a way to not think about product. Maybe there's, you
know, some some cavity or something would do the trick.
Well, thank you. Yeah, thank you. Thank you for coming on the
show. This has been awesome. Yeah, absolutely. Yeah, that
Wow, that one places.
Wow, what a session. That really was amazing. Karl, what are your
takeaways?
I completely agree with you. That was an exciting
conversation. I'm really, really glad that we got to have that
time to talk to John. That was really quite good. Some of the
things that I liked everything that he said, and I don't want
to spend all this time basically re saying everything that you
just listened to. But of the kind of key points to bring out,
he talked a lot about his background, you know, we asked
him a lot of questions about his background, because product
management is one of those things that's I think it's best
performed. And I think that John's experience kind of shows
this as well that is best performed when it's backed by
context, and a multitude of little experiences and just the
tinkering and things that make up life, you know, all those
things that kind of well round a person, then they get to a point
where they can do product management as opposed to, you
know, say somebody that's fresh out of school and doesn't have
all that experience may not know all the situations as well as
somebody who does. He also made the point that there's finding
out that there's other people like him, like through his
writing, finding that out. But there's a large diversity of
folks that we work with, you know, people like him in a lot
of different disciplines, his readers aren't all product
managers, you know, that come from all over the place, but
resonating with things that he writes. He also talked about how
success is made up of, you know, context across multiple
dimensions, whether that's the norms, environments, tools, the
stage of a company, etc. And just that you cannot look at
only one metric of success, you have to really look across all
these different dimensions to really figure out do you have
success or not. And then also one thing that I really like
about John is just, you know, he is a prolific writer, but
that's how he learns, you know, this is how John learns. And
that's why his writing is so introspective and not
actionable. And he's definitely gotten feedback, hey, we'd like
actionable content, but that's not what he does. His writing
is there for him for learning. So Danielle, what did you take
away from this?
Yeah, I think same as you, I don't want to repeat the whole
episode. Every time we chat to folks, I make notes as we write
so that I have these bullets at the end for the wrap up. And I
basically just transcribed the whole episode as we were
talking through it. So kind of picking my top ones are really
difficult. I loved the phrase that the Instagram version of
product management and because whenever we talk externally
about what we do as product managers, we do kind of gloss
over some of the difficult bits, whether that's because legally
you can't talk about the projects that you're working on
or you just choose not to or because you choose to put the
best version of yourself on the internet. It's so believable on
Instagram and it then it's a conversation we're surrounded by
especially women in social media is that you know, Instagram
versus reality and I just forget that there's LinkedIn versus
reality as well. And that detail is sometimes lost. I loved his
comment about when you're writing a blog or when you're
you're kind of going through these things that the bar is
being curious enough to throw yourself into it like you have
to be curious enough in a subject to truly throw yourself
into it, submersed yourself in it, understand it and then to
be curious to write about it to publish that and share that with
other people. I really enjoyed just that phrase. I think it
takes some of the pressure off like as long as you're curious
about a subject, you don't have to be the subject matter expert
you just have to be curious enough to learn loved that and
then I also because I feel this so truly that so much of being
in product requires and just demands that your self identity
gets wrapped up in being a product person that you can
forget to have fun like it's okay to have fun with being a
product person you it doesn't define who you are, you know, if
you put a feature out there and it flops like, okay, great. Did
you have fun? Did you learn? Let's move and it's it's easy to
get caught up in the drama sometimes. So those are my
takeaways. Let us know what your takeaways were. What comments
really made you think and what new thoughts did you have
listening to this podcast?
Drop us a line at hello at productlyspeaking.com or join
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I don't think you can call it nattering.
I guess actually we did stay on topic and it's not technically
nattering.
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