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September 25, 2025 28 mins

Ever feel overwhelmed by your to-do list? That sensation of drowning in tasks while your most important work gets pushed aside? You're not alone—and there's a solution hiding in plain sight.

In this eye-opening episode, Jesse breaks down a deceptively simple framework for identifying exactly which tasks in your life and business should be automated or outsourced. Using a visual "bucket and drops" system, you'll discover how to categorize your work, break large responsibilities into manageable components, and analyze frequency patterns to make strategic delegation decisions.

What makes this approach different isn't just the practical methodology, but Jesse's candid acknowledgment of the real barrier most professionals face: "The solution for getting comfortable with the idea of outsourcing or automating is reps." He shares personal examples from his own podcast production journey, revealing how he transitioned from doing everything himself to focusing solely on the interviews while delegating all other aspects to his team.

The brilliance of this system lies in its scalability. Whether you're considering hiring your first virtual assistant or looking to reclaim hours each week through strategic automation, this framework provides a clear path forward. Jesse offers specific tactics for getting started, including how to use AI tools to identify automation opportunities and how to begin with lower-risk monthly tasks if you're hesitant about letting go.

Ready to stop doing work that others could handle better? Want to invest more time in developing your unique gifts? This episode delivers the practical roadmap you need to make it happen. Listen now and take the first step toward working smarter, not harder.

Check out the Video for all the details

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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
We are going to be talking about how to figure out
what to automate and what tooutsource.
What I got for you, actually, isa super simple way to like
figure out what those things are, and I'm just going to kind of
flash this bad boy up at youright now.
We're going to dive into myTrello board and we're going to
get into what are the buckets,how many drops, or what are the

(00:24):
drops that are in the bucket,and then how many times do they
happen.
This is how we kind of tease itout and peel apart the big
giant tasks that we have, thatwe do all the time that we could
like outsource or automate sowe could spend more time
investing in ourselves.
I'm Jesse, and the stuff that Ishare here on these live

(00:44):
streams and on the socials isthe tips and tricks that took me
from the field to like actuallyoperating my own business,
which is a little crazy.
And the reason I share thesethings is because I want to help
you spend more time working toleave this industry, this world,
your teams, your communitiesbetter than you found them.

(01:06):
Like I said a little while ago,we're going to drop into the
buckets.
And what do I mean by buckets.
I'm kind of super big overviewwhen I'm talking about buckets.
I want you to think aboutcolors, right?
Or buckets first.
What are the things For me?
I've got a podcast.
I've got work like my growingmy business.
I got personal.
I've got publishing.
I've got work like growing mybusiness.
I've got personal.
I've got publishing.

(01:27):
I call it publishing, which isjust like blogging and writing.
And then I've got other things,but generally that's where I
spend, oh, and thenadministrative right.
So generally that's where Ispend my time.
When you're thinking aboutbuckets, I want you to think
about where are the large chunksof spaces that you spend your
time in?

(01:48):
That is what qualifies as abucket.
And then, when you think aboutdrops in the bucket, within each
of those buckets there's abunch of little things, a bunch
of little steps that fill thebucket right.
And so we want to like teaseout what are the buckets first,
and if you've already done thisphenomenal, let me know in the
comments what are your buckets,and then we're going to tease

(02:11):
that apart.
And then, once we tease thosethings apart and we do some
reflection and that's why thetool is important, because the
daily domination board is themethod or the mechanism that
helps me see all of these thingsand that's the critical point
is being able to see, visually,see and reflect on.
What are all the elements, whatare all the buckets?

(02:32):
Where am I spending all of mytime and breaking it up If we
don't have it like, if it's inour head, it seems like this big
, one, singular thing, and if itstays that way, we will never
be able to like, automate oroutsource the thing.
All right, folks, so let's jumpinto it.
So what are your buckets?
Think about this Like right nowbrainstorm.

(02:54):
It's not a test.
I'm not going to grade this badboy and I ain't going to tell
on you, but drop it in thecomments.
What are the buckets that youspend most of your time in?
And I'm going to kind of starthigh level and say work home,
marriage, right, whatever thosebuckets are.

(03:14):
Start thinking in those termswhat are your buckets?
And let's go to the fancyTrello board.
So this is my like.
You don't have to do it thisway, I promise.
I know this is probably going toseem psychotic to a lot of
people out there, but that's theway I roll and so, visually,
you can see the different colorshere.

(03:36):
Those are my different buckets,and so for yellow, it's
administrative.
It's administrative stuff thatI have to do invoices and emails
and schedules.
So that's one bucket.
Then I have the orange bucket,which is relationship building
and industry committees.
Right, that's me being involvedor engaged with other human
beings that aren't necessarilylike a business or a service

(03:59):
that I got to deliver, a productI got to deliver.
It's just maintainingconnection and contributing as
much as I can to the people Icare about.
Then I have this red one, whichis curveball and social
marketing, and if you were hereat the last live stream, we
talked about the curveball, sowe're not going to talk a lot
about it today.
You can go back and watch thereplay.
And then purple, and so I'mgoing to spend a lot of time
talking in the purple buckethere because it's the most

(04:21):
granular.
I think that might paint thepicture that we're talking about
.
So purple is my podcastingbucket.
It's all the little tasks thatare associated with me
scheduling, recording, producing, posting a podcast.
There's a bunch of drops inthere.
Then I got blue for real estate, I got green for publishing, I

(04:41):
got pink for me, self-care andskill building, and I got this
kind of black gray bucket andthat's all things related to my
business.
And so I'm going to ask you guysagain what are your buckets?
Hopefully, or if this ain'tmaking sense, let me know.
First step, step one what arethe buckets?
Where do you spend most of yourtime at?

(05:02):
Get those out of your head,write them down, scribble them.
You don't need crayons to do it, just get them out of your head
, like, think about what arethose buckets, what are the
things, the areas that you spendmost of your time in.
And then, if you're using theTrello board or you can do it on
your calendar I like Trellobecause it's my love language
Then you can assign colors tothe thing.
Right, and the main value forme in assigning colors to it is

(05:26):
so that I can visually see andidentify what bucket am I
playing in.
Again, this is to help us teaseout and filter through the big
giant, monumental things that wedeal with on the regular and
see it in a more granular level,because this is going to set
the foundation for what do weautomate and what do we

(05:50):
outsource.
And why do we want to automateand outsource?
It is so that we can spend moretime developing our gifts and
talents and share our gifts andtalents with the world, because
that's the only way we're goingto make it better the world,
because that's the only waywe're going to make it better.
Let's go to the comments.
Craig says I manage my financesin buckets, so why not organize
my time better?

(06:10):
Also, oh, I love that.

(06:31):
Okay, craig, thank you forthrowing that out there.
What Craig, to the point tolike figuring out what I can
automate and outsource, is moreabout the thinking than it is
the stupid tool that I use.
I use the tool so that I cansee it visually, and it's a
habit that I've had for I don'tknow, probably a decade now,

(06:52):
using the Trello board and themural board and all the things
that I use, anyway.
So, craig, thank you forthrowing that out there.
It's what are the separation,where the boundaries may be,
between the differentcommitments that you have or the
different things that you'reinvolved in.
Write those down, then assignthem a color.
I like colors, again, becauseit's super duper visual.

(07:14):
So, Craig, thank you for that.
My brother and so we talkedabout identifying your buckets.
Now, after you've identifiedthe buckets, I want you to pick
one right now If you didn'twrite them down.
Write them down.
Write down a few, two or threeor four buckets where you spend
most of your time.
Like I said earlier, you cankeep it simple, work home easy.

(07:37):
There's probably a whole lotmore that you do.
Pick one of those buckets andnow what we want to think about
is what are the drops in thebucket?
Right, because what does abucket do?
It collects water, it collectsfluid or whatever, but it gets
filled.
My buckets get filled with abunch of little drops of things,

(07:57):
a bunch of and in terms of likethis, this idea of drops I'm
talking specifically about, likethe steps or the little tasks
associated with that big bucket.
So let's go back to the Trelloboard and so you can see here
the drops in my bucket and we'regoing to look.

(08:18):
I don't know if y'all can readthat.
Maybe I don't Let me know ify'all can read that, like, if
the um, uh, whatchamacallem, ifthose little the cards are, if
they're clear enough to read,cause maybe I want to keep them
secret.
But anyways, what I want you tolike focus on is the purple
color, right, this range ofpurple.
That bucket is my podcast bucketand so when I first started

(08:39):
doing my podcast the learningsand missteps podcast, that
switch podcast I had no idea howmuch time it was going to take
and how much work was involved.
But I did it weekly.
Well, at the first, at first Idid it like every other month,
and when I do it on thatfrequency it's kind of hard to
see.
I just knew it was a lot ofwork and it was going to take,
you know, three to six hours forme to go from interviewing to

(09:04):
posting the thing right.
Why?
Because I timed it.
But as I got intorepetitiveness, right as I did
it, the more reps I got, theclearer I could see like, oh
wait, this is a separate.
It's all in the same bucket butit's a separate task and it's
things that I needed to scheduleout.
And it was also able.
I was it enabled me to see thatI don't have to do it all in

(09:25):
one shot.
I could like break it up.
And so back to this, back to thetool, back to my buckets.
You can see here there'sprobably more that I can get
into, but that's not the point.
I've got episode art andpublish, so I got to create some
episode art so that I canupload it and publish.

(09:45):
So that is one of the drops inthe bucket I've got do the
interview, right.
What does that mean?
I have to interview amazingpeople, or I get to amazing,
super amazing people, twoamazing, super amazing people.
Then I do a cut in the introand the outro of the thing,
right.
Like I have a little teaser atthe beginning.

(10:07):
Now I'm talking about this inpresent tense.
I don't do most of this stuffanymore.
I used to do all of it and thenit's produced.
So produce for release.
What that meant was to edit thestupid thing, qc check is
listen to it after I've done theediting and it's right before I
publish it.
And then another drop in thebucket was research, podcast,
guests and, like I said, thosecould be broken down even
smaller.
The point is, when I starteddecided that my podcast and this

(10:34):
could be anything that you havein your world.
It could be your workoutroutine, it could be, it could
be your finances.
Like Craig, I think this is abeautiful example.
Craig says financial management, document control, hr,
self-management, curve balls,meetings oh, those are the
labels.
That's what I'm talking about,baby Nice.

(10:55):
So there you go.
You got a template that youcould use from Mr Craig.
Thank you, my friend, that'sfreaking awesome, okay, so so
back to the thing.
I first started by saying I havea podcast bucket and originally
that purple card was justpodcast.
But over time, because I couldsee how often it was happening,
I was like man, maybe I need tobreak this down.

(11:15):
And because I had a bucket forit, I was able to start thinking
about what are the littleelements within that bucket, and
so you could see there's one,two, three, four, five, six
we're not going to countbroadcasting, because that's
actually what I'm doing rightnow is live streaming, right?
So there's six steps in mybucket.

(11:35):
Those are the drops within mybucket.
Now the question then becomesis like so what, jess?
You keep talking about bucketsand drops in the buckets.
I thought this was aboutautomating and outsourcing.
Ding, ding, 100% accurate.
And so, by getting granular,right to like diving into the

(11:58):
weeds of the thing, I was ableto identify.
Because here's the thing,here's a secret.
Nobody tells you, right, we alltalk about automating and
outsourcing and how amazing itcan be, and you know, value your
time or nobody's gonna valueyou and all of this stuff.
I I agree with all of it, bythe way, but it's super hard,

(12:18):
not because of, like,articulating the steps and all
that.
You got freaking chat GPT.
Now that could do that for you.
It's hard because I had torelease control comfort with

(12:41):
inviting someone else into myspace to do the work that I so
earnestly spend hours upon hoursobsessing about, and so I don't
.
The solution for gettingcomfortable with the idea of
outsourcing or automating isreps.
I don't know any other one.
So if you're out there in theomniverse and you have like a
super simple trick that helpsyou really come to terms quickly
about outsourcing stuff orautomating stuff, let us know in

(13:04):
the comments, because I've seenthe people that I've worked
with, folks that I've coached.
That is the biggest hurdle forthem.
It's not necessarily figuringout what or how to outsource,
it's coming to terms andbecoming comfortable with the
idea of somebody else doing thething.
That's super hard, but anyways,that's a little extra bonus

(13:24):
there.
I don't even know where that'scoming from, craig, I'm going to
blame it on you.
When I did my buckets and thedrops of the bucket, I was able
to see okay, I've got a wholebunch of little things in here.
I've got the episode art.
I got the interview to do, Igot the intro and outro, I got
the produced edit, qc, research.
That's a lot.

(13:45):
And then it was a simplequestion that I asked myself Of
all of these things in thisbucket, which are the ones that
no one else can do, that only Ican do?
And this isn't new knowledge,right?
This is a fundamental thingwhen we're thinking about
scaling and growing our business, or outsourcing work, et cetera

(14:09):
.
And guess what?
The only thing on that list ofall of those drops that no one
else can do was the interview.
Now, I'm sure you're probablylike well, anybody could do an
interview.
Yeah, you're right, but I wantmy face in the podcast too,
right, so I wanted to physicallybe there.
But the scheduling of it, theresearch of the guest, the

(14:30):
production, the editing, theepisode art, the cutting in of
the intros and outros, I don'thave to do that, and there's
plenty of people out there inthe world that have the skillset
and love doing that.
And so that's where I startedLike, like for real, for real.
Ms Kayla, if you're watching,you're amazing.
Love, all the help and reliefthat you bring to my life.

(14:53):
I got me a personal assistantand I knew that I needed to get
his personal assistant.
If y'all know me out there, I'mnot the easiest to get a hold
of and my response time isn'talways the greatest, and that
was just.
That was why it's like, okay, Ineed to deliver a better
service, so I need an assistantso we can like close that gap.
I evaluated like, okay, whatare the things that I can give
that are like low risk, thathappened on a high frequency, so

(15:16):
that we can get good at it, andthen we can build on that.
And it was the podcast.
And so now the only thing I dowell, I still do the scheduling.
I'm working on that I'm workingon, but so I do the scheduling
and I do the interview.
Everything else is done byRenee at Duran styles, uh,
editing, and miss Kayla, who whodoes all the other finishing
touches and makes it amazing andmakes the images and puts the

(15:39):
things out there.
But I never would have gotten tothat point if I didn't
understand my buckets and Ididn't understand the drops in
the bucket.
And so, quick review we'regoing to talk with the first two
main points and then we'regoing to get into the third
point.
But the first two main pointsis what are your buckets?
Think about that, write it downor drop it in the comments.
What are the buckets?

(16:00):
Where do you spend most of yourtime?
Family, friends, working out,church?
We all have different thingsthat we're committed to, the
little projects that you have.
Do you work on vehicles?
Are you building a hot rod?
Whatever those are, thosequalify as big buckets.
And, in thinking, within thosebig buckets, start breaking them

(16:21):
down, because that's where thedrops in the buckets are and
those are the things that dropsin the bucket, the steps that
are associated with those big,bigger things that you're doing.
That's where the ideas or thethings to automate and outsource
are going to come from.
I'm going to give you anotherreal quick example.

(16:41):
I don't really like going tothe groceries because I don't
like standing in line and I getrude and it's just.
It's just not.
It's not a fun experience forme and it's a bit somewhere
between two and three hoursevery week for me to do that,
and you know, in particular,about my produce.
But I had to let go of that andso I outsourced it, because
those two to three hours, sure,I'm paying, you know, a few
extra bucks for it, but thosetwo to three hours I can invest

(17:05):
in other things, relaxing.
I could give some moreattention to all the people out
there in the omniverse all themake it happeners come up with
new ideas, whatever it is, butmost of all, it helps me
conserve my energy.
So maybe, if you want to likeearly start, get the things, the
tasks, the chores right.
This might be an easy key foryou.

(17:26):
Get the chores that you do on aregular basis, that's easy
Laundry, housekeeping, lawn work, maintenance on the vehicle,
grocery shopping, like getcreative with this.
All of those things are thingsthat you can outsource or you
can automate right, depending onhow you look at things.
Now, if you're out there andyou're like, okay, I've hit it,

(17:54):
I feel like I hit a ceiling.
I've been progressing, I'vebeen making things happen, I've
been getting things done, but Ifeel like lost or I feel maybe a
little empty.
Or, like Scarface said, is this?
It Is this what I've beenworking for?
I got you the Self First TimeMastery Workshop is coming up
and in that workshop, we'regoing to deep dive into all of

(18:16):
these things.
What we're talking about on thiscall right now is just one, one
element from the dailydomination practice, which is,
you know, managing yourexecution on a daily basis.
We ain't even touching on thestrategically selfish scheduling
or guilt free future planning,and so if you're looking for an
edge to like, get more time backand just feel fulfilled

(18:39):
whenever you do everything oranything that you want to do,
you got to sign up for that badboy.
So drop self first in thecomments.
If you're interested, I'll giveyou the link.
If not, that's all right.
Come back for the next freelive stream, all right.
So now that we've talked aboutwhat are your buckets and what
are the drops in the bucket andyou really, really want to get a

(19:02):
return on your investment, whatyou want to do is evaluate, and
this requires some reflection.
All of this is going to requiresome work, y'all.
I know some of you probablythink like oh, my God, I got to
create all these cards and I gotto do colors.
It's like, yes, yes, itrequires work.
Or just keep doing what you'redoing.
If you're completely fulfilled,satisfied and operating to your

(19:24):
optimal potential, keep doingwhat you're doing.
If you're completely fulfilled,satisfied and operating to your
optimal potential, keep doingwhat you're doing, because
there's other ways to do it.
This is just the way.
I know how to do it.
But if you want a differentexperience on this world and you
want to contribute to a greaterdegree, my recommendation is
you try some of this.
We did the buckets, we gave themcolors, we broke down the drops
in the bucket, all the littlesteps associated with those

(19:46):
things, and so now we have aframework or a template to use
whenever we're scheduling ourwork and scheduling our task or
going into the daily dominationboard and doing the thing.
So here, let me do this Right.
So we got daily domination.
That's what we're doing today.
Do this right.
So we got daily domination.

(20:06):
That's what we're doing today.
The trick to figuring out andidentifying, pinpointing the
thing that'll bring you thegreatest value, is all about
reflection, which takes us backto why coloring the thing is
super, super helpful.
We're going to go to the donecolumn and once a week I do this
.
I should do it more often, butwhatever, it's what I do.
And now I've got all thesecolors we already talked about.

(20:26):
Purple has something to do withmy podcast, right?
Blue has something to do withmy training.
Black gray color is associatedwith my business.
This orange stuff is, you know,relationships, people, industry
committees, et cetera, and so Ican come through here and I can
just at a glance look at allthe things that I have going on
and I can see how frequentlythey're happening.

(20:49):
Oh, I'm not even sharing thedamn thing here we go my bad.
So I can go through the Trelloboard here and I can see at like
this is current as of right now, and I can look at all the
colors and see where am Ispending most of my time.
Now there's some stuff here likethis social marketing.
That's like me posting andcreating posts and commenting

(21:09):
and all of that.
That's coming up quite a bitand I know how much time it
takes.
If you're on here, you know howmuch time it takes, and so for
me that might be a signal that Icould do something about it or
that I should maybe consideroutsourcing it.
I won't, because y'all know Ilove all the attention that I
could do something about it orthat I should maybe consider
outsourcing it.
I won't, because y'all know Ilove all the attention that I
get from you guys and theinteraction.

(21:29):
But the point being is, when wetrack it right, create the tide.
We have a bucket.
We know what the drops in thebucket, put them in the done
column and count right Like forreal.
It's that easy.
Count the number of times thosedrops in the bucket happen.

(21:50):
How frequently do they happen?
My recommendation, I, are thebuckets where you spend your
time and then what are the dropsin those buckets, what are all
the little steps, the littletasks associated there, and you
might need to go more and moregranular.

(22:11):
That's entirely up to you.
My recommendation is go asgranular as is reasonable.
Log them, we track them and wereflect on weekly how many times
like, what, which color is intaking up the most space, and

(22:32):
then we start evaluating.
If you're like nervous and youyou know I don't know what to
outsource, or I don't know I'm alittle nervous about, you know,
automating that it's a littlerisky.
Cool If that's kind of yourenergy at.
That's a little risky.
Cool If that's kind of yourenergy.
My recommendation is findthings that happen like monthly,
whatever that is, I have noidea, I don't know your life,

(22:52):
but things that happen on amonthly basis, that is a
frequency, right.
That is something that happensmultiple times and you can
consider it.
Okay, let me dive into thatthing that happens once a month
and peel it apart just a littlebit more and then figure out is
it something that I can automate, is it something that I can
outsource?
Or, like Jennifer Lacey says,outsourcing for her was

(23:17):
delegating.
I struggled with that until Istarted identifying those
specific tasks and so if you gotkids, you can totally delegate
some of this stuff right Nowit's going to take some more to
make you know, build thosehabits or whatever, but the idea
is, if it happens on a regularfrequency, that is absolutely a

(23:37):
candidate for outsourcing orautomating.
Right, if you're nervous aboutit and you want to get your feet
wet and kind of test the waters, first look at things that
happen on a monthly basis.
Now, if you're like me, likeman, I, I, I gotta sleep, I
gotta eat and you've got a bunchof things like that, you can

(23:57):
totally keep, get off your, yourplate, which I know all of you
are make it happeners, otherwiseyou wouldn't be here listening
to me to gab and jab about allof this stuff.
Look at things that happenweekly, things that happen on a
regular basis on a weekly oreven daily.
Dive into those, because withinthose tasks, whatever it is,

(24:18):
there are steps that canabsolutely be automated or
outsourced, absolutely beautomated or outsourced.
And when I say automated, I'mgoing to like for real, for real
, this is going to sound superdumb and a lot of people are
going to say, oh my God, jesse'sone of those people now.
Like, yes, I am, I can get onchat, gpt, and I will feed it

(24:42):
Like here's the thing that I'mdealing with, that I do it this
many times.
Here are all the steps, right,I will just feed it as much
information and then I will sayhow can I automate this?
And it'll give me an answerthat's usually kind of wonky and
then I just keep going back andforth with it Well, what if
this?
But I really want it to looklike this and it'll give me an

(25:03):
answer or at least give me someoptions.
Uh, in terms of how to automateit, that now, if you're in
trello or some of these othertools email, I mean, there's all
kinds of automation tools outthere for like anything.
So research it.
And I just found thatresearching via, via the, the ai

(25:23):
, is way, way faster, becauseit'll give me stuff and I'll say
, okay, no, those aren't reallywhat I was looking for.
This is actually what I meantthis is more precise, okay, and
it'll give me more.
And I'll say, okay, this one'sreally good.
Is there more like this?
Is there a free option?
Is it like all of that?
And I just keep bugging thehell out of it until I feel good
and then I test out the thing.

(25:44):
So, summary if you haven'tidentified your buckets, get
them out of your head and givethem colors.
What are the big buckets whereyou spend the most of your time?
Or maybe another way to thinkabout it is the things that take
your time.
List those out, give a sign ofcolor to them or not.
You know, I know how valuablethe colors are to me, but maybe

(26:05):
not to you and then think abouteach bucket, one at a time.
What are the drops in thosebuckets?
What are all the little steps,the little tasks, the little
duties associated or that arefilling up that bucket?
The reason you do that is sobecause now you can find the
repetitive tasks to outsourceand automate, and when it comes
to outsourcing, there are tonsof opportunities.

(26:27):
If you've ever had the kind ofwild thought of like maybe I
should get a virtual assistant,freaking, do it Like.
Do it now, because you're goingto need to figure out how to do
that.
I know because I'm still tryingto figure it out.
If you're looking for anyservices there, my sister,
samantha, absolutely offersthose services.

(26:48):
Remember, be kind to yourself,be cool, and we'll talk at you
next time.
Well, I got some music now forthe.
What do you think about that?
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