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January 2, 2024 • 45 mins

Have you ever stood at the crossroads of passion and professionalism, wondering if it's too late to change paths? Brian's story is a beacon of hope for career changers everywhere, as he shares his incredible shift from being an outdoor guide to a software engineering maven. With a candid discussion on the art of scaling impact, Brian's insights on mentorship, and his personal blueprint for knowledge dissemination through blogging and podcasting, this episode is a treasure chest of wisdom for anyone looking to navigate the tech terrain or amplify their own influence.

As we unravel Brian's journey, you'll be inspired by his tenacity in tackling the tech industry head-on, sans a safety net. His proactive stance on moonlighting to gain experience, coupled with his relentless networking, showcases the grit required to transition successfully. Moreover, Brian's ascent to a leadership role as a fractional CTO and his strategies for influencing multiple companies unfold like a masterclass in tech guidance, shedding light on the creation of a dynamic 'playbook' for navigating the rapids of tech leadership.

Wrapping up, Brian doesn't just leave you with stories of challenges conquered; he extends an open invitation to continue the conversation beyond this episode. For those intrigued by the intersection of technology with fields like healthcare, education, and cybersecurity, and anyone dreaming of a leadership role that spans industries, this episode is your gateway to an exciting future. Brian's journey isn't just a chronicle of personal growth, it's a roadmap for any professional hungry for transformation.

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Tim Bourguignon (00:00):
So how do you help yourself to not say yes
right away?

Brian Childress (00:07):
So one of the things I do like to do, if it's
something like a mentorship orsomeone's asking for information
, I, I try and I take anengineering approach and like
how can I solve this in a waythat scales?
And so is it a blog post that Ican write, or a video I can
record, or a you know, a podcast, just like this that I can

(00:29):
record and share with them as away to not only answer their
question but also potentiallyanswer it for someone that
doesn't know they want to askthe question yet.
So that's really been somethingI've tried to focus on more and
more is how can I scale theinformation that you know from
one on one To one to many?

Tim Bourguignon (00:47):
hello and welcome to developers journey,
the podcast bringing you themaking of stories of successful
software Developers to help youon your upcoming journey.
I'm a host team.
Oh yeah, all in this episode Ireceive Brian children's.
Brian is a husband, father,technologist and avid adventurer
.
As a technological advisor witha strong background in software

(01:09):
engineering, cloud computingand cyber security, he is
Experienced in helping CTOs andCEOs make the right technical
decisions for theirorganizations and the rest we're
gonna hear today, brian, a warmwelcome David.

Brian Childress (01:24):
Tim, thanks for having me.
It's great to be here, but mypleasure, my pleasure.

Tim Bourguignon (01:28):
But before we come to your story, I want to
thank the terrific listeners whosupport the show.
Every month you are keeping theDev journey lights up.
If you would like to join thisfine crew and help me spend more
time on Finding phenomenalguests than editing audio tracks
, please go to our website devjourney info and click on the

(01:51):
support me on patreon button.
Even the smallest contributionsare giant steps toward a
sustainable dev journey Journey.
Thank you, and now back totoday's guest, brian.
As you know, the show exists tohelp listeners understand what
your story look like and imaginehow to shape their own future.
So, as as usual in the show,let's go back to your beginnings

(02:13):
.
Where would you place the startof your dev journey?

Brian Childress (02:16):
Let's see.
I remember taking some veryrudimentary programming classes
in high school, but really Ithink for me my programming
journey started in graduateschool.
Honestly, I Was not the kidProgramming on my family's
computer at eight years old.
That just it wasn't me.
So I really didn't get intocomputers until I went back to

(02:39):
to graduate school and fromthere really really found my
passion and have continued togrow and evolve in software
engineering since then.

Tim Bourguignon (02:51):
For the non-us listeners, grad school is the
equivalent of college, issomething like this so post my
bachelor's degree.

Brian Childress (02:59):
So this is working more towards like a
master's or something alongthose lines.

Tim Bourguignon (03:03):
Yep okay, how did?
How did you come to todiscovering or rediscovering a
computer programming at thatpoint in time?

Brian Childress (03:12):
So my undergraduate degree, my
bachelor's degree was insomething kind of so far removed
from software engineering andcomputer science.
It kind of wasn't even funny.
Actually started myprofessional career as an
outdoor guide, so I would takepeople white water rafting and
mountain biking and rockclimbing and that sort of thing
and really, really enjoyed thatwork, but found, you know a

(03:36):
little bit of time into thatthat I wasn't completely
fulfilled.
It wasn't really kind of, youknow, is intellectually
challenging, didn't really kindof do the things that I was
looking for to do, and so I atthat point I went back to
graduate school.
I went back to college To learna geographic information

(03:58):
systems.
I felt like that was a goodkind of blend between the things
that I found interesting and my, my passion for outdoors and
outdoor venture, and that's whatgot me into programming.
At that point we were learningPython, was the primary language
that we use in GIS and was, youknow, building some small data

(04:19):
analysis programs and working invarious systems, and you know
that that was kind of, I wouldsay, the beginning of what's led
me to where I am today.

Tim Bourguignon (04:29):
So very much as a tool first for doing
something else, for doing GISanalysis or whatever you do, and
then it evolved into a subjectmatter in itself.

Brian Childress (04:42):
Absolutely.

Tim Bourguignon (04:43):
Yep, it's exactly right.
Do you remember when, when thethis this, this u-turn happened?

Brian Childress (04:51):
I was a ski bum , so I was living in a small
town in Colorado, I Was apainter during the day and that
allowed me to live and ski anddo those sorts of things, and
you know that I had a great time.
Right, I was in my early 20sand, you know, from there went
and did some Outdoor guiding.

(05:13):
I had already been doing it,you know, kind of all throughout
college but found, you know, Iwant something different, right,
I just I want a differentchallenge.
And it was at that point that Idecided, hey, let me look at
Going back to school forsomething To continue to, you
know, grow and expand my skillsand maybe find something that

(05:34):
I'm even more passionate about.
And that's where I kind ofstumbled into GIS as a.
I had no idea what it was whenI even started looking into it.
It just kind of broughttogether a few different
interests of mine and then fromthere I just continued to evolve
and After graduate school, gotout into into the workforce

(05:55):
developing software.

Tim Bourguignon (05:56):
Okay, so you didn't.
Didn't work as the GIS expert,but what would you do as a GIS
graduate?

Brian Childress (06:04):
I did for about four months.
Okay, I worked as a contractorfor the transportation
department and so, basically,for GIS, it's it's, you know,
putting information and Tying itto points on the globe, right.
So it's the same technologythat makes our GPS units work.

(06:25):
And you know Strava and all ofthose types of apps.
It's all based on GIStechnology.
And so, you know, working forthe transportation department, I
it was not nearly as glamorous,right.
I was basically putting togetherand analyzing large amounts of
data that had been collected onour highway systems and bridges
and culverts that run themunderneath roads, and Signs that

(06:49):
are on the side of the roadsand that sort of thing.
And so, you know, it was, it wasgood, you know, to kind of get
out there and practice a lot ofthe things that I had been
learning in school, but itwasn't, you know, it wasn't
exciting, it wasn't the thingthat I was really looking for,
and and in a prior job that Ihad had, you know, one of the so

(07:09):
I worked three jobs to putmyself through Graduate school
and one of those jobs I hadworked with a company who was
doing they were contractors forMedicare and Medicaid and they
had an opportunity to come on asan application developer with
their group.
So they had an internal softwareplatform that they had built

(07:32):
and they offered to bring me onand I jumped at the opportunity.
I thought it was be a great wayto kind of learn and you know,
I I think I kind of missed beinga junior developer and kind of
going through those Climbing theranks.
I kind of skipped right oversome of those steps and was
thrown right into the deep endand you know, I think I've

(07:56):
continued to To to go forwardfrom there.

Tim Bourguignon (08:00):
Is that your way of learning or of Going at
problems with with air quotes,jumping the cold water, going to
the end and and see whathappens?

Brian Childress (08:11):
I Think it is Maybe not intentionally, it just
that seems to be the way ithappens.
But yeah, I kind of just you gofor it and figure some things
out along the way and get someskin to knees and that sort of
thing.
But yeah, I would say it'sprobably been a theme throughout
my career is to kind of takethat approach.

Tim Bourguignon (08:34):
All right, fair enough.
How did you go being I assumeand correct me if I'm wrong kind
of a sole developer during yourstudies, working on your data
analysis and tools, but probablyAt least it was for me without
all the best practices ofsoftware engineering?
I'm really doing coding, Iwould say, but, but not Crafting

(08:57):
software for the long term,with, with the legacy in mind,
etc.
And jumping into this new worldof application development and
discovering all this.
Assume all the.
Do you Discover that beforehand?
How did that transition?

Brian Childress (09:11):
work, not.
Yeah, I very much learned thaton the job, and a lot of that
was just what I thought wasright, because I didn't
necessarily always have a teamthat I could rely on.
I didn't have a great softwarementors that I could lean on
that had years of experience,and could you tell me about all
the ways that this could gowrong?
I can just Follow my gut and,thankfully, made some decent

(09:36):
decisions most of the time.
Yeah, I didn't really.
I didn't have a lot of thatmentorship early on, and so I
saw it out in other ways.
I tried and I think early in mycareer is when I started to.
Not only I was working fulltime as an application developer
, but I started freelancing andmoonlighting and doing

(09:58):
development projects on my own,and I think I tribute a lot of
my success to that hard workDoing freelancing and
moonlighting to learn a lot ofthose things, and it was just
another way that I could makethose mistakes and then I
learned from them.

Tim Bourguignon (10:16):
That's the deep end of the pool again yeah,
right going from freelanceprojects as the not junior but
still beginner in your career.
That's ballsy.
How did you find those projects?
How did you manage to get inthere with probably not so much

(10:39):
experience to show for?

Brian Childress (10:42):
I don't know charm and charisma.
I mean some of the earlyprojects you know I was finding
on I don't know if you'refamiliar with it, but like
craigslist dot com.
So I mean this is many yearsago.
You know I was creatingwebsites for wedding venues and
insurance companies and thatsort of thing.

(11:03):
It wasn't wasn't necessarilysoftware engineering, right, I
was kind of largely puttingtogether wordpress websites.
But you know I had met somepeople at meet ups really good
friend he and I stillcollaborate today Met a meet up
group just randomly, you knowstill user group, and he and I

(11:23):
have collaborated and worked onthings and so he and I would
Kind of bump through thattogether, you know.
But I just always looked foropportunities to kind of learn
and found a you know a lot ofthe things that I was learning
on my own in those early daysI'm continuing to use today.

(11:44):
So it was really reallybeneficial.
I probably didn't know what Ididn't know at that point.
Maybe that was an advantagebecause I didn't let it hold me
back that I didn't know thosethings.

Tim Bourguignon (11:59):
Yeah, the benefit of being young and still
naive.
You mentioned.
You mentioned meet ups.
See, you discovered meet upreally early on in your career.

Brian Childress (12:12):
I did.
I did, you know.
I was just ravenous because Ididn't.
I wasn't collaborating with alot of people in my day to day
work, especially not from asoftware perspective, and so is
ravenous for more informationand to be around folks that were
doing it.
And it was kind of at that timewhere start ups were a really,
really sexy thing, likeeverybody wanted to be in start

(12:35):
ups, you know, because we werehearing about the explosion of
google's popularity and all theyou know, the free food and the
you know slides and all of thosekinds of cool things that was
coming out around that time, andso there was just a lot of draw
towards it.
I had one of my collegeroommates what is a founder in a

(12:57):
start up and you know, I meanit was like three guys in a
small bedroom apartment in sanfrancisco like developing
software that ended up Growingand growing, like it was just a
very exciting thing, and so Iwanted to find a way to break
into that, and meet ups were away to do that, and at the time
I was living in denver andthere's a huge start up

(13:18):
population there, and so I wasable to attend a meet up every
night if I wanted, to Differentuser groups.
It was just a very popularthing and you know, from that,
made a lot of great connections,learned a lot, you know.
It also kind of pushed me outof my shell.
I'm not naturally, you know,kind of extroverted, or, and so

(13:41):
it really kind of pushed me togo and meet other people and
learn from them and see what Ican share and maybe help them in
some way.

Tim Bourguignon (13:49):
I'm gonna be piggyback on that.
How would you Behave, goinginto a meet up?
First meet up you come in thecity.
You haven't been to that meetup yet and the first time you
show up, how would you be ableto start making connections,
feel at ease, just just feellike somebody who's a who's a

(14:11):
welcome there.

Brian Childress (14:13):
You know it wasn't easy for me.
You know I tend to be kind ofmore reserved, held back, I'll
be the ones kind of sitting inthe back corner of the room kind
of seeing what others are doing, you know.
But I found for me the way thatI kind of broke through some of
that was I would sit like in aspot like up towards the front,

(14:39):
like a couple rows back, kind ofa few seats in, basically in a
spot where Someone was almostforced to sit next to me and
then when we're sitting next toeach other, like most of the
meetups where there was apresentation and then some
networking and we have pizza andbeer afterwards, and so by

(15:01):
having somebody sit next to me,then you know it was just more
of a one on one conversationthat I could kind of break
through that.
You know that anxiety or thatfear and we can start to talk
about things.
And because we were at the sameuser group, it was largely
based around specific technologyor you know a topic that was
really interesting.
I could then use that as myopening.

(15:23):
You know, hey, tim, what wouldyou know interest to about
JavaScript or something alongthose lines?

Tim Bourguignon (15:31):
That's.
That's a good one.
I've heard a couple others andhow to, how to break in there at
one.
One was to sit as well in thefront, but mostly to attract the
eyes of the person speaking.
When you're speaking, you'requite often searching for
somebody who's really attentiveand and then you focus on that
person.
It's your, your persona, forthe audience, and I found it

(15:54):
personally Call me to be thatperson for the, for the speaker,
and then it was easier to talkto the speaker afterwards and
break the ice and you've beenlooking at me for an hour now,
so let's chat and that felteasier, at least to me, and I've
heard that from a couplepersons as well that eat, help
them break that high in that iceand that's great.

Brian Childress (16:17):
I mean I do the same thing.
Now that I'm doing a conferencespeaking, I do the same exact
thing.
I'll pick out a couple peoplein the room and they're my
anchors.
No one else exists in the room.

Tim Bourguignon (16:31):
That's the secret.
It really really helps, reallyhelps.
And the other one I've heard isto go to someone and ask them
for referral.
Asking them maybe you know whoI could talk to about react.
I'm passionate about react.
Maybe it's not a react meetup,I'm passionate, but react.
You know someone here who Ishould talk to and it's a great

(16:53):
way to to have this person, tohave this person answer you and
help you without cornering heror him into having to talk to
you.
If they, if they don't want totalk to you, they can just say,
well, talk to Bob of their he's,he's knowledgeable about that,
and there you go.
And if they, if it's theirtopic, then they can start
talking to you.
And these two combines ofsitting in the front and using

(17:16):
this, this diversion technique,is really helped me personally
in many conferences.
To come there and know no oneand start talking from the get
go.
That's really really helpful.

Brian Childress (17:27):
Nice, I like that a lot.
I mean, I have to borrow that,yes.

Tim Bourguignon (17:32):
Okay, so you are in that journey, started
your first gigs, or at leastyour first job, doing God knows
how many gigs on the side as afreelancer and learning during
meetups.
Did you sleep at that time?

Brian Childress (17:47):
Not much.
Thankfully, in graduate schoolI was also introduced to coffee,
so I've been a an avid consumer.

Tim Bourguignon (17:57):
sense yeah so how long does a lifestyle work
out?
Do you have to change somethingat some point?

Brian Childress (18:09):
Um, I don't know, I think I'm just, I have a
personality that naturally justI want to have a lot of
different things going on, youknow, and so I found it ebbs and
flows a little bit.
I kind of get to the brink ofburnout or maybe actually burn
out, and then I have to take alittle bit of a break.

(18:31):
But I like, a lot of thingsinterest me and so I try and,
yeah, we explore a lot ofdifferent things.

Tim Bourguignon (18:39):
Do you have to actively Restrain yourself from
from going in one or the otherdirection just because you know
it's gonna be too much?

Brian Childress (18:48):
Now I do, I absolutely do.
Earlier on, I think In thoseearly days you're just looking
for anything, especially aroundtechnology, like which
technologies do I enjoy, whichones do I not?
What problems do I like tosolve, what industries are
interesting?
And now I feel like I've Got abetter idea of those things and

(19:10):
so I try to Restrain myself abit more.
But it's still hard to say nowith somebody comes and says,
hey, can you help out with thisthing or do you mind mentoring
me?
It's, it's really hard to sayno.

Tim Bourguignon (19:24):
How do you Help yourself to not say yes right
away?

Brian Childress (19:30):
I.
So one of the things I do liketo do, if it's something like a
mentorship or someone's askingfor information, I I try and I
take an engineering approachlike how can I solve this In a
way that scales?
And so is it a blog post that Ican write, or a video I can
record, or a you know, a podcast, just like this that I can

(19:52):
Record and share with them as away to not only answer their
question but also potentiallyanswer it for someone that
Doesn't know they want to askthe question yet.
So that's really been somethingI've tried to focus on more and
more is how can I scale theinformation that you know from
one on one to one to many?

Tim Bourguignon (20:11):
Okay, and and so you've been writing blog
posts, publishing videos, etc.
Creating your own content forthat or Partly for that partly
for that, partly for myself.

Brian Childress (20:23):
To you know, my , my blog is taking a bit of a
hit of the past year, to justLife, it's gotten busy.
But I originally started thatfor me.
I wanted a place to be able toreference information and so I
started it there.
And you know I found justhaving a blog, a public Space on

(20:47):
the internet, has been hugelybeneficial.
I mean, it helped me to getjobs and bypass technical
sections of interviews and it'sbeen really, really helpful.

Tim Bourguignon (20:58):
And there's not quite anything like googling
for something and finding one ofyour own blog posts.

Brian Childress (21:04):
I wish I could tell you how many times that's
happened, that I've appeared onthe first page of Google and oh
yeah, I wrote about this a yearago.
I've already figured this out.

Tim Bourguignon (21:15):
And for God, I love it.
Which is awesome just writeabout it.
You immerse yourself enoughinto the subject matter to
really be able to write about itand then forget about it
entirely and really discover itlater.

Brian Childress (21:33):
It's just like high school, right we studied
enough to pass the test, andthen we immediately forgot
everything.
I just have a resource.

Tim Bourguignon (21:42):
You mentioned.
I'm jumping back a bit.
You mentioned you skippedjunior dumb, I'm not sure that
the word, but now it is and youjumped both feet first into a
more senior role.
And how did that evolveafterwards?
Is there some more graduationof senior?
Is your different flavors ofseniority?

(22:02):
What kind of thoughts does thattrigger?

Brian Childress (22:09):
I think for me, yeah, there were various areas
of senior that I focused on, soit became less about creating
something that worked and morefocused on creating something
that's maintainable, that I cancollaborate with a larger team
on.
That continues to kind of focuson solving a business problem.

(22:31):
So it still wasn't as likeheavy technology focused, it was
just more how do we solve thisproblem, do it in a more
maintainable way, because youknow a lot of the things that I
was doing earlier on it wasn'tas important, it wasn't, they
weren't as long lived projectsand that sort of thing.
But as I continued to progressin my career, I found that that

(22:53):
was actually important, and sothen I became the person that
really, really focused on youknow, quality and craftsmanship
in the software and took a lotof pride in that, and so you
know now Working with a numberof different clients, that's
something that I really reallyfocus on, because I found it

(23:14):
hugely valuable for me, for theteams that I worked on and now,
you know, for my clients as theycontinue to grow and scale.
It's something that I stilllike to focus on.

Tim Bourguignon (23:25):
How do you approach selling is not the
right word, but but convincingsomebody?
They have a software which isworking and now is the time to
start focusing on more quality,more craftsmanship, more
sustainability and more effortfor the long term.
How to approach this discussionwith them?

Brian Childress (23:47):
So I think it's important to know our audience
and who are we talking to, andso I always like to understand
what are the things that drivethat particular person.
If it's the business owner,they may not care about the code
quality as long as it works.
So I can talk about, well, whathappens if it doesn't work, or
what happens when we need toexpand it to onboard a new

(24:09):
customer that's going to bringadditional Revit, new into the
business, and if we don't focuson the quality and the
craftsmanship and themaintainability now it's going
to be very difficult for us tobring in that new customer,
which is then either going todelay them coming on board or
potentially we could lose themas a customer altogether.

(24:32):
And so really kind of focusingon what is that particular
person interested in and thentying in the technology and
software from there.

Tim Bourguignon (24:42):
Hmm, yeah, that's a very, very important
advice Really knowing youraudience and tailoring your
arguments for that.
Obviously, if you start talkingwith them about principles,
solid principles, etc.
It's not going to connect.
No, they usually are.
So in the in the Bible I readat the beginning, you kind of

(25:08):
hinted as now you would be doingsome kind of consulting job.
Is this how you would describeit?

Brian Childress (25:15):
Yeah, yeah.
So you know I'm doing the kindof freelancing in the
moonlighting for a number ofyears, so I mean call it
consulting, and so now I'm fulltime, fractional, cto and
technical advisor.
So I consult with a number ofdifferent startups and small
media and businesses that aredeveloping custom software,

(25:36):
typically in the B2B space, andhelping them to.
You know, I like to say that Ihelp get turn around struggling
software projects and help themto scale, and so that's that's
what I do.

Tim Bourguignon (25:50):
Okay, so fractional CTO would be kind of
a sidekick offer CTO learningthe ropes, or how would you
describe the fractional CTO?

Brian Childress (25:59):
So the way I operate is you know, I bring
years of you know, expertise andyou know lessons learned and
mistakes made to organizationsthat may not need or may not be
able to afford a full time CTOand oftentimes, they don't need
a full time CTO.
A lot of organizations areprobably just looking for a

(26:21):
really strong lead developer andthey call them the CTO, and so
what I'm doing is helping themto.
You know, I bring a strongbackground in software
architecture and scalability, sowe'll focus there if that's
what they're looking for.
Bring in a lot of just softwareengineering, best practices,
right Code reviews anddeployment strategies and that

(26:42):
sort of thing.
Bring a lot of that in bigfocus on security as well
application security and youknow how can we grow the team in
a way that's effective All ofthose types of things I help my
clients out with.
So it's it's a bit of a mix.
You know, different fractionalCTO is kind of focus in
different areas, but those arethe areas that I tend to focus

(27:04):
on most.

Tim Bourguignon (27:05):
OK, so I hear really laying down the
foundation, whispering the rightwords, putting things in motion
so that it evolves in the rightdirection from the get go, and
then it will evolve without you.
You'll probably be somewhereelse, as I imagine your gigs
probably short term or a fewmonths, but not much more than
this.
Am I right there?

Brian Childress (27:26):
Typically, yeah , I kind of aim for three to six
months.
In most organizations it may belonger.
We just might taper off howmuch time I'm committing to that
particular engagement.
Yeah ultimately, my goal is towork myself out of a job right,
put those systems in place toempower the right people,
potentially bring on board fulltime the people in the right

(27:48):
role and then kind of workmyself out of it.
You know, that's tends to bethe best and the most exciting
approach for me.

Tim Bourguignon (27:58):
How do you manage to get in and right away
start thinking about your exit?
I would go full, all in and say, ok, now I'm there, and two
years later I would wake up andsay, oh gosh, where did time go.
How do you handle this?
Phasing in, phasing out andright away probably searching
for next gig and phasing adifferent gig at the same time?

(28:18):
How do you handle all this?

Brian Childress (28:21):
So it goes kind of can I give the classic, it
depends.
We've got a bunch of developers.
So I tend to kind of ramp upquickly.
We'll do, potentially, adiscovery month where we figure
out OK, what are the realproblems here that we want to

(28:42):
solve?
Is it scalability, is it teamcollaboration, is it, you know,
we pick the wrong technologiesand we need to do a big
refactoring.
So we'll figure out what'sgoing on, kind of put together a
strategy, put together, youknow, what resources do we need,
what team members do we need,and then I'll tend to oversee

(29:05):
that process as it goes through.
You know, we'll kind of adjustas needed and then ultimately
taper off.
And so once the project ismoving along well, the right
team members are in place, thenI'll taper off into more, like
of you know, kind of an advisoryor a retainer type of role when
I'm still available to the team, but not necessarily as hands

(29:28):
on day to day.
But I mean it's nice because Ican kind of come in and shake
things up and really focus onwhat's best for the business,
what's best for the project.
You know, I don't have the sametype of limitations.

(29:48):
I think around like trying tobe friends with everybody, right
?
I don't want to, you know,alienate anyone, but you know I
am coming in there to solve aproblem, I am coming in there to
help the organization.
So, with that focus, it allowsme to, you know, make some
decisions that I might not makeif I were coming in as a full

(30:11):
time person.

Tim Bourguignon (30:13):
Yeah, makes sense, makes sense.
You mentioned the tagline oh,at least I know it's your
tagline on LinkedIn Helpingstruggling projects.
Do you think it's because ofthis tagline, because of this
focus that you've been giving toyour career, that companies
which are struggling at a pointin time go out and reach out to

(30:34):
you?
Or is it all those companiestry to make it on their own and
at some point realize somethingis not working right and at some
point then reach out to findsomebody with knowledge Call it
a fractional CTO or any othername and then find someone to
steer the ship back into theright direction?

Brian Childress (30:55):
Yeah, I don't know that it's the tagline
necessarily that draws them in,but I have, from a lot of my
LinkedIn content has drawn folksin to my world.
So, you know, I've had thepleasure of working on a number
of different projects that werestruggling Because they, you
know, the architecture, thetechnologies that they had

(31:17):
chosen were too complex, theteam wasn't delivering on time.
They, you know, may have hadother challenges.
They might have hired adevelopment agency or a
freelancer who just kind ofwalked away with all the code.
There's a number of differentthings that have kind of
happened but, yeah, a lot of thecontent that I put out on
platforms like LinkedIn kind ofspeaks to the challenges that I

(31:40):
see, unfortunately, day to day,and its organizations that you
know may not have a strongtechnical focus and so they
relinquish a lot of control overto the development team or even
an outside agency or an outsidefreelancer and they just lose
control and ultimately, you know, a lot of the times when I come

(32:02):
in, it's, you know it's the.
I've got a lot of work to do.
I rent things around sometimes.

Tim Bourguignon (32:11):
I hear you.
I'm sure I want you to swear,but then know, if you could, if
you, if you imagine going to aproject that wouldn't be
struggling right now, would yoube attacking the this problem
that's called the problem withthe same, the same way, doing
this discovery months, trying tofind where the problems are?

(32:33):
Would you go at it differentlyif it wasn't obviously
struggling from the get go?

Brian Childress (32:39):
I think I would go at it a little bit
differently.
Typically when I come into astruggling project we've spent a
lot of money, we're over budget, we're over time, the team is
frustrated, they're working alot of long hours I think we can
make some very drastic, quickdecisions to kind of turn us
around.
But if that's not the case, Ilove to come into projects where

(33:01):
I just get to sit and hang outand talk with the developers
one-on-one, maybe provide somementorship to them and just see
where things are.
What is that normal process forthe team and look for areas that
I can add some efficienciesthat I can continue to maybe
push some of the developerstowards opportunities of growth,

(33:23):
if that's what they're lookingfor.
So if I don't have to, I loveto be able to sit back and just
see how things operate andreally just make sure that I
focus on showing that I reallyappreciate all the work that has
been done up until this point.

(33:44):
Because if those developershadn't put in all those hours
and the blood, sweat and tearsto develop the platform to what
it is today, I wouldn't have ajob.
They wouldn't be bringing me inNow.
I might be coming in to fix andtweak things, but it's because
of all their hard work that Ihave the opportunity to come in.
So I always want to be gratefulfor that and really show the

(34:05):
developers that I'm there tohelp support them.

Tim Bourguignon (34:08):
Amen to that.
It's always a hard balance tostrike between coming in and
seeing things and saying, hey,maybe we should change this, and
you know you're going to hurtsome feelings because that's the
way they were successful so far.
And so you're going to pushplaces where it usually is
painful, but at the same timelistening in and really

(34:30):
understanding from how it iscalled second degree observation
, understanding why are thingsthis way, why it was done this
way and why it evolved into thissituation.
To just really understand howit came to being there and not
just remove something that isabsolutely crucial for the
organization.
It sounds silly.
You just remove it and theorganization crumbles.

(34:52):
So really trying to find thisbalance is always hard.
And how does it work on thethree to six months timeline
when you first want to observe?
Do you have enough time?

Brian Childress (35:04):
So we can observe in a lot of different
areas, and so I tend to reallypoke in a lot of different
places.
I'll not only scheduleconversations with the kind of
the key folks.
I'll schedule conversationswith members across the team.
I'll poke around and slack,I'll look at the conversations

(35:26):
that are happening and all thepublic channels and any private
channels that I've been added toJust see what that conversation
is.
I'll look at pull requests andthe comments that are added
there how is code added anddeployed and I'll look at
documentation and how are wecollaborating on that.
And so there's a lot ofdifferent areas that I can kind

(35:49):
of observe without it being aone-on-one conversation with
someone, and so I'll look forthose areas.
I'll look for trends and fromthere I've been in enough
organizations and on enoughteams and projects that there's
at least a few differentsolutions I might be able to
propose to the team as anopportunity to improve, I see.

Tim Bourguignon (36:16):
You've mentioned burnout or kind of
burnout before.
This is going in, going out,jumping on a new project that's
probably linked with a lot ofstress, or at least long hours
to really find the north, findnorth, understand what's
happening, the topology of thecompany, etc.

(36:39):
And then, by the time you'reconfident with all this, well,
it's time to start with yourcompany.
Do you think you have staminato do this for a long time?
Do you see yourself doing thisfor years and years, and years?

Brian Childress (36:54):
I think so.
I've certainly evolved myapproach over time.
I've got a much more robustplaybook that I follow now.
That allows me to kind of getto some of that information a
little bit more readily.
But I think some of my nextphases are actually going to be
to grow the group that I workwith and collaborate with

(37:18):
closely, so potentially bringingon other architects and
technical advisors and otherfractional CTOs to be able to
help me to scale and take someof that day-to-day work off of
my plate so I can be a bit morestrategic with some of the work,
but not I still want to be ableto help as many organizations

(37:40):
as I can to deliver greatsoftware at the end of the day.

Tim Bourguignon (37:44):
But when you mentioned playbook, it sounds
like taking up a silly projectof writing a book about all this
, which would end up with evenlonger hours.

Brian Childress (37:56):
It's conversations like these, and so
anytime that I find that I makea suggestion or come up with an
idea, I'll dump it into theplaybook and just kind of
continually add to it over time,and so it's more of a what
would I already be doingnormally.
Let me put that into one place.
Instead of a concerted effortto write a book, it's more just

(38:19):
kind of collecting from all mynotebooks and all my
conversations, pulling all thattogether.

Tim Bourguignon (38:26):
Is this publicly available?
Is this your blog or is thisstill notes for yourself.

Brian Childress (38:32):
It's a mix, so some things I'm happy to share
any of it.
None of it's secretive, but Idon't have it in a pretty format
that is probably digestible bymost, but yeah, anything like
there's.
How do I do due diligence on atechnical project?
How do I do an architecturereview?
A lot of those things I'veabsolutely shared with other

(38:53):
fractional CTOs or technicaladvisors in the industry.
I'm happy to share any of thatif it's helpful in any sense.

Tim Bourguignon (39:04):
If we can link some to the show notes to give a
taste of what we've beentalking about.
I think that would be great forthe audience.

Brian Childress (39:12):
Absolutely yeah , happy to share.

Tim Bourguignon (39:14):
Awesome.
Do you see yourself doing thisfor years and years and years?
So you said yes, kind of.
But I heard I heard helpingmore companies.
Is this scalable, being in thetrenches and doing some
strategic work, etc.
Will you work change basically?

Brian Childress (39:35):
That's what I'm trying to figure out now.
If I'm honest to him, what doesthat scaling look like?
Having a playbook, having a setof repeatable processes,
certainly helps, I think,helping to scale it.
I need folks to collaboratewith colleagues that have years
and years of industry experienceand have been in those trenches

(39:58):
before and have really thatlevel of experience and made
some of those similar mistakesto be able to collaborate with.
I think that's something as anindustry, we're struggling a
little bit with because we don'thave a ton of people at that
experience level that are stillpractitioners in the industry.
I'm always looking foropportunities to collaborate

(40:21):
with folks in that way.

Tim Bourguignon (40:24):
There you put the word I was trying to find
and ask my question veryclumsily being a practitioner.
What I fear for you when I hearthis is that you're going to
graduate into some kind ofmanagement slash, strategic
position and not be apractitioner anymore.
I fear it because I have afeeling that you need this

(40:47):
practitioner stance from 14minutes discussion together.
If I'm putting you in the wrongbox, sorry about that.
I fear you would be missing itat some point.

Brian Childress (41:00):
You're absolutely right.
So, selfishly, I hang on to acouple projects where I'm still
hands-on coding, where I stillhave the opportunity to bring in
some new technologies, some newpatterns.
I think I will always maintainthat I may not do as much
hands-on keyboard coding as Ihave, but I'll always hold on to

(41:22):
a few projects there, and partof the way that I've tried to
design my business andultimately the life around it is
to have time to be able to goand explore some of those new
areas and really just have funwith it.
I think that's a thing thatreally keeps a lot of us
technologists in the industry isthere's so much new things that

(41:42):
we can play with and experienceand explore.
I certainly want to be able tocontinue to do that for a long,
long time.

Tim Bourguignon (41:50):
Oh yeah, I mean to that.
If somebody was wondering, hey,this fractional CTO thing kind
of sounds like fun They've beenmore or less as a senior
software developer somewheredoing a lot of things inside a
company but saying, hey, this ishelping other companies put out

(42:11):
the right foundation at theright time, that sounds like fun
.
What would be your advice tostart getting into this
direction?

Brian Childress (42:18):
Yeah, I like to say that technology is the
easiest part of what we do.
In many ways, it is astechnologists.
I can Google my way to asolution.
On the technology side, I thinkthe skill that we have the
opportunity to continue todevelop is around.

(42:40):
How do we collaborate withother humans?
How do we collaborate andcommunicate across time zones?
Like you and I are todayPutting yourself in a much more
of a leadership position andreally focusing on not only the
people, the collaboration, butalso the business as well.

(43:01):
I think as technologists, we'realways excited about
implementing new technologiesand new patterns, but at the end
of the day, we need to makesure that it serves the business
, because the business needs tomake money in order to pay our
fancy developer salaries.
I would encourage anyone that'sconsidering something like this
to really start to focus on theleadership and the business

(43:24):
acumen.
We're solid technologists.
We can continue to learn andevolve there.
That's a small portion of whatwe really need to be focused on
to be successful.

Tim Bourguignon (43:37):
Absolutely.
Thank you for highlighting this, Brian.
It's been a blast.
Thanks for coming to your story, starting in GIS and diverging
entirely and ending upwhispering in the ears of CEOs
and CEOs worldwide.
Where would be the best placeto continue the discussion with

(43:58):
you?

Brian Childress (43:59):
I would say right now I'm most active on
LinkedIn.
I encourage everyone to reachout, connect with me, send me a
message on there.
I'm happy to connect andschedule a call if it makes
sense.
That's going to be the bestplace to connect.

Tim Bourguignon (44:12):
Do you have anything on your plate that you
want to highlight before we callit a day?

Brian Childress (44:17):
I've got a lot of really interesting projects
going on right now A couple inthe healthcare space that are AI
focused, a couple in education,in finance, cybersecurity.
I'm really, really excitedabout what this next year holds.
I think there's going to be alot of really fun projects and

(44:39):
opportunities.

Tim Bourguignon (44:41):
Can we read about it on LinkedIn or on your
homepage when you write about it?

Brian Childress (44:45):
Yeah, absolutely, I'll definitely be
sharing.
I'm learning every day.
Typically, what I share onLinkedIn is something I learned
the day before.

Tim Bourguignon (44:56):
That's the best source of ideas.
It's just falling flat on yourface and saying, oh, I have to
write about that.

Brian Childress (45:04):
Absolutely right.

Tim Bourguignon (45:06):
Brian, thank you so much.
I will add some links to theshow notes with LinkedIn, your
own page and maybe a couple ofpages of the playbook you've
been gathering along.
If you want to connect withBrian, don't hesitate.
Go to LinkedIn and reach out.
Brian, thank you so much.

Brian Childress (45:21):
Tim, thank you.

Tim Bourguignon (45:23):
That's been another episode of DevGhost
Journey.
I will see you there next week.
Bye-bye.
Thanks a lot for tuning in.
I hope you have enjoyed thisweek's episode.
If you like the show, pleaseshare, rate and review.
It helps more listenersdiscover those stories.
You can find the links to allthe platforms the show appears

(45:44):
on on our website devjourneyinfo.
Subscribe.
Talk to you soon.
Bye-bye.
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