Episode Transcript
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Jessica Rosario (00:18):
Hello and
welcome to the Maximize Your Day
podcast, a place forentrepreneurs who are building
their business in pursuit offreedom and flexibility to do
the things they love.
I'm your host, jessica Rosario.
I'm a New Yorker turn FloridianWho knows a thing or two on how
to effectively manage your timewhile juggling multiple
priorities.
I'm an ex-corporate leader whowalked away from my 9-5-ish to
(00:41):
launch and grow my business.
In this podcast, i shareinsights on mindset, business
productivity, habits andstrategies to help you take
control of your to-do list andmaximize your day, which will
help you feel more confident andless overwhelmed and getting
more done in less time.
I'm so excited you're here.
Go ahead, listen in.
Welcome back to the show.
(01:07):
I am so excited to share withyou today someone who is near
and dear to my heart and I can'twait for you to hear her story
and what she does, because she'sbeen instrumental in my
business as well.
As you know getting thingsorganized and you guys know this
show is all about maximizingyour day, So I definitely know
(01:28):
you're in for a treat.
I know I say that all the timein every episode, but you really
are in for a treat.
So excited for you to hear fromJenna Paolo.
So go ahead, jenna, andintroduce yourself.
Tell us who you are and who youserve.
Jena Paulo (01:43):
Yes, thank you.
First of all, thank you forhaving me, and I'm Jenna Paolo.
I'm a business operationsconsultant as well as a verify
click-up consultant, andessentially what I do is I help
my clients maximize the way thatthey utilize a project
management tool called ClickUp.
I help them build out the tool.
I consult on the tool, butessentially what I do is I want
(02:06):
my clients to marry theirprocesses with the tool so they
can utilize ClickUp as theircentralized business hub and
have one place to go to managetheir projects, their people,
their processes, all of thethings And mainly, who I serve,
i would say.
I mean, it's kind of varied.
I work with a lot of differentindustries, but I do work with a
lot of coaches.
(02:26):
I work with a lot of digitalmarketing agencies, hr
consultancies, people who aremore service based typically is
who I mostly serve, but my goalreally, no matter who you are,
is to really help you utilizeClickUp to maximize the way that
your business runs and developprocesses that just make sense
(02:48):
for you.
Awesome.
Jessica Rosario (02:49):
Awesome.
I can't wait to hear what thisepisode is going to be about,
because, even though I've beenfollowing you for a while, i
purchased one of your coursesabout I want to say it was about
a year ago and it just reallychanged everything in the back
office of my business, and notonly for my coaching business,
(03:10):
but also I own a commercialcleaning business.
For some of the people in myaudience that knows that I'm a
multi-passionate entrepreneurBut the importance of utilizing
this system in both ends of mybusiness, it was just truly eye
opening.
So I'm super excited to haveyou here Now.
Jenna.
Tell us what inspired you tostart your business.
Jena Paulo (03:31):
Yeah, so I actually
come from a background in
educational operations and I wasmanaging large schools, large
teams, doing trainings, doingall of those things.
And when I kind of made theshift into the online space and
one of my main reasons forreally creating, making the
shift is because I was kind ofoverwork in the nine to five,
(03:54):
right Like I wanted to do my ownthing.
I wanted more flexibility in myschedule, i wanted to just have
more time to do the things thatI loved.
And so, taking my experience ineducational operations and kind
of shifting that and utilizingthat background, that knowledge
in the online space, I was ableto create a business that I love
(04:15):
.
Jessica Rosario (04:17):
Awesome.
Do you think that there was abig challenge when you shifted
from doing schools versus movinginto the online space?
Jena Paulo (04:25):
Yeah, i mean,
there's always going to be a
challenge when you're movingfrom something that you've been
so used to doing, right?
I was doing that for over 12years And now I'm kind of
shifting into this new world,right, that I'm not super
familiar with, not supercomfortable with yet.
So, yeah, there are absolutelyhurdles that I had to kind of
(04:45):
step over, and I would say someof the big things that stood out
was that I really had to.
I was now managing myself,right, instead of being confined
to these hours of work and likewhat I was supposed to be doing
.
And so, being someone who wasreally used to structure and
(05:07):
having this structure kind ofcreated for me, i then had to
create that structure for myself, right, and really start to
build a business.
That one took intoconsideration what I wanted my
life to look like, right, andtwo, how I could serve my
clients in the most effectiveway.
And so, yeah, there werechallenges that definitely came
(05:29):
with that, especially in thebeginning stages, right, and I
would say even with every stageof business, there's new
challenges and new hurdles,right, but I would say just
getting started in the beginningwas one of the bigger hurdles.
Jessica Rosario (05:42):
Yeah,
absolutely, and I'm so glad that
you bring that up, because oneof the struggles that I
experienced when I leftcorporate in 2019 was that I
kind of lost the structure ofwhat my day looked like And in
that moment I was the mostorganized person when I was in
corporate and balancing all thethings.
But leaving that part of me, ikind of lost myself in that and
(06:05):
trying to figure out.
I was working all kinds ofhours.
I didn't have a real structureof a client called me on a
Sunday.
I picked up So, even if it wastaken away from family time.
so I didn't really have thoseboundaries set And I can see how
, for some that are moving intosomething new, it just kind of
knocks you off your feet justtrying to figure out what that
new process is going to looklike.
Jena Paulo (06:26):
Yeah, yeah,
absolutely.
Because you come from having somuch structure to no structure
at all And you have to kind ofbuild what you want that
structure to look like becauseyou don't want it to mirror that
9 to 5, right That you left.
You want it to be a structurethat makes sense for you and the
life you want to live.
Jessica Rosario (06:43):
Yeah, for sure,
For sure.
So what would you say was thepivotal moment for you when you
realized I want to incorporate asystem and be specialized in
this system?
What was that aha moment foryou?
Jena Paulo (06:58):
Yeah, absolutely So.
When I started my business, ididn't go straight into ClickUp.
Right, i didn't even know whatClickUp was when I first started
.
When I first started mybusiness, i was working more on
the back ends of my business,more as like an operations
manager.
Right, managing the back endpieces And quickly realizing
that these clients needed asystem in order to sustain the
(07:18):
business.
Right, because you know, we'vegot Google Docs here at Google
Sheets, we've got notes in thisthing and that thing, and you
know it's kind of spread out allover the place.
And so, quickly realizing thatwe needed some structure in the
business, i went and did someresearch, right, so there's a
slew of project management toolsyou can use.
I dabbled in Trello, i dabbledin Asana, i dabbled in Monday
(07:41):
and Basecamp, i dabbled in allof these other systems, and some
of them would work for a whileAnd then I quickly realized it
has some things I like, but Ineed to do more.
Right, I need more flexibility,i need more functionality here.
And so finally I found ClickUp.
And once I did, i literallynever turned back.
(08:01):
It was like this is the tool.
And once I found the tool, i ofcourse started implementing it
for my clients, building outtheir workspaces and things like
that, and really learned tojust love the system and loved
how I could incorporate myoperational background into
developing systems like this.
And so it quickly evolved fromdoing some buildouts for clients
(08:26):
but also offering otherservices to strictly offering
ClickUp as a service right Inthe form of consulting, in the
form of doing these very largebuildouts and now doing things
like coaching other ClickUpprofessionals right, and so it
kind of evolved.
But that was the pivotal pointof utilizing these other systems
(08:47):
, not really liking them,needing to find a better
solution and then finallyfinding that solution and
ClickUp.
Jessica Rosario (08:53):
Yeah, I
completely agree.
I will tell you, I dabbled withTrello also.
I played with Asana for a hotminute, but Trello was my main
one.
And I think at one point I wasworking with someone, a
freelancer, that used ClickUp,so I kind of like moved over to
that platform temporarily untilI fully transitioned, and I
(09:14):
think when I fully transitionedit was just a hot mess.
So one of the things that ledme to you was looking for
experts in ClickUp, notnecessarily to understand usage
of the platform, because I couldlearn that on their ClickUp
University, right.
But I think it was more so aboutthe use case for our business,
because I knew how to use it.
(09:35):
For my coaching business It wasokay.
I was using it already withcertain things, but when it came
to our brick and mortarbusiness we have a field service
business We wanted it to talkto other systems.
You know we use HubSpot.
Hubspot now has an integrationwith ClickUp.
We use Bamboo HR to manage ourworkforce and that has an
integration with Inside ofClickUp.
We needed something that canreally help us, kind of like set
(10:00):
up that back officeinfrastructure, and that's when
I found you.
So I'm sure that you hear a lotfrom clients that they're
stressed out theuser-friendliness of ClickUp.
It's not easy to learn and allthese things, because that was
one of the things that I wastelling myself until I found you
(10:21):
.
So what would you say is thebiggest hurdle that you've
helped your clients overcome tobe able to manage this platform?
Jena Paulo (10:31):
Yeah, definitely.
So.
I mean, many clients likeyourself find that when they
find the tool right, when theyfind ClickUp, they love the idea
as the possibilities right, ofwhat the tool can do and how the
tool will perform.
And so once they get startedinside of the tool and start
actually messing around with it,it kind of becomes a different
(10:52):
story because there is so muchrobust functionality of the tool
right, there are so manyfeatures that we can turn on and
turn off and there isautomation and there is
dashboards and there istemplates and there is all of
these things right, which canstart to become very, very
overwhelming.
And so when I work with myclients, what is really
important is that we kind ofjust set the foundation.
(11:14):
We really have to understand thebusiness before we can marry it
with the tool.
And I kind of talk about that alot, where we are marrying your
business processes with thefunctionalities of the tool,
right, because we don't want tochange your business, we don't
want to change the way that youfunction if it's working well,
right, we want to marry thoseprocesses with the tool.
And so in working with myclients, that's a really big
(11:37):
thing is first understanding howthe business functions, what
your processes look like when itcomes to client experience,
what the processes look likewhen it comes to marketing your
services.
you know what I mean.
So just really diving into whatthe processes look like and
then developing structuralhigher key inside of the system.
And if you know about ClickUpor have heard people talk about
(11:58):
ClickUp, we talk about thehierarchy a lot inside of the
tool And that basically justmeans how you organize yourself
right, your spaces, your folders, your lists, and so really
teaching the fundamentals to myclients is a really big piece of
them then understanding thebroader aspects of the tool and
how to apply those things to thebusiness.
(12:20):
So it's the processes and thenit's really understanding just
the foundational things of thetool.
Jessica Rosario (12:27):
I love that.
So would you say that thetraditional business owner,
whether it's an online space orbrick and mortar, doesn't matter
?
Would you say that everybusiness should have a project
management tool?
It doesn't have to be ClickUpright, But they should have a
project management tool.
Jena Paulo (12:46):
A thousand percent,
yes, they need something to
really keep all of the pieces ofthe business in one place,
right, because things get lost.
You forget things.
You have team members who youwant to communicate with and
you're sending messages in Slackor you're sending it via email.
The communication can get lostvery easily, especially when
you're working with multiplepeople inside of a business.
(13:07):
But even if you're asolopreneur, you need ways of
keeping track of your projects.
You don't want client tasks tofall through the cracks, right?
You don't want to lose leads.
You don't want to not manageyour email campaigns in the
right way, right, whatever thatlooks like for you.
So, absolutely, no matter whatthe tool is, you need a tool.
Jessica Rosario (13:26):
Awesome.
So I'm going to ask you acouple of questions.
I just need you to tell me ifit can be done in ClickUp.
Okay SOPs.
Jena Paulo (13:38):
Oh hell, yeah,
Absolutely Right.
Yes, so you need to create aSOP database inside of your
workspace so that you don't haveto go looking for the document
somewhere else, so that you havean actual documented process
that you can connect to a task,right?
So if you, let's say, you bringin a social media manager to
help you manage your Instagramposts, they know exactly how to
(14:01):
do it from start to finish, withthis SOP that is connected to
their tasks or inside of adatabase in some way inside of
the tool about.
Jessica Rosario (14:09):
You already hit
it, but marketing.
Jena Paulo (14:13):
Yes, absolutely.
You wanna manage the creationprocess there right, from taking
that idea, that post idea fromstart to finish or a real from
start to finish right, and sobeing able to manage those
things, your marketing throughworkflows, tracking, dates,
tracking, assignees, tracking,kind of where it's on the
process.
It absolutely can do that.
Goal setting Yes, there'sactually a goal setting feature
(14:38):
inside of ClickUp And so you'reable to manage your goals in
there utilizing that feature.
But then there's also othercreative ways that you can
utilize the tool to manage yourgoals, your KPIs, all of that
sort of stuff.
Jessica Rosario (14:50):
Awesome,
awesome.
I mean the list can keep goingright.
But when you think about, evenwhen I think about the way I use
my ClickUp on one business andthe other, i mean there's my
marketing, there's myheadquarters, information of how
I manage my business, there'smy speaking engagement, there's
my podcast.
I was so proud of myself when Ireached out to the Jenna Paolo
(15:12):
to let me know hey, do you wantto be on my podcast so you could
test my workflow while you'reat it, and it was so cool to be
able to kind of see the things.
Jena Paulo (15:21):
So that was all.
Jessica Rosario (15:21):
by the way, I
learned all of that through
Jenna, So I thought that wasawesome.
How about personal?
Jena Paulo (15:27):
things?
Yeah, you definitely can, andso I know a lot of people that
I've worked with.
They have a personal spaceinside of their bigger ClickUp
workspace right, just to helpthem manage those day-to-day
things groceries, or to dothings for the kids.
Whatever that looks like inyour personal life.
You can absolutely manage thosethings.
(15:47):
They actually just createdsomething really robust for
myself and my husband.
I'm like you're going toutilize ClickUp.
We're going to manage all ofthe household things inside of
ClickUp, and it's been great.
Jessica Rosario (15:58):
That's awesome.
that's awesome.
I did see a couple of weeks ago, you posted something on your
stories I think it was anInstagram on how you guys
delegate some of your householdtasks, so I thought that was
really neat.
Haven't been able to get Alexthere yet.
Maybe one day, but I haven'tbeen able to get him there yet.
So, jenna, tell me now, on theother side of systems and
(16:20):
operations and all these thingsaside from your brain which I'm
thinking is similar to mine,where I'm always thinking
systems, processes, goals.
I need to plan, i need to knowthings in advance, how do you
keep yourself motivated whenthings don't go your way?
Jena Paulo (16:37):
How do I keep myself
motivated?
That's a really great question.
I think that a lot of it kindof comes from knowing that it's
worked before right, becauseI've gone through waves each
business goes through wavesright, where some months are
really great and then you kindof fall off a little bit and go
(16:57):
back up right.
So keeping yourself motivatedis really important And I think
the best way that I do that,just personally, is knowing that
I have proven strategies thathave worked and that I can
always go back to thosestrategies right, because if I'm
trying something new and maybeI'm offering a new service,
whatever it may be, maybe I'mtrying a new way of marketing
(17:19):
myself utilizing LinkedIn, let'ssay, which I don't do, right,
maybe I wanted to go and trythat.
I know that, although I canventure off and try these new
things, that I have kind of ahome base of what I know works
well for myself and for mybusiness, and so just giving
myself the flexibility to trynew things but also continue to
(17:41):
utilize those proven strategiesif I need to.
Jessica Rosario (17:44):
Love that, love
that.
Can you speak to the importanceof being able to kind of
disconnect yourself from the dayto day to be able to just
maximize your energy?
Jena Paulo (17:58):
Yes, yes, for sure,
because I've been on both sides,
right, i've been on the sidewhere business consumed me and I
Want, first of all, i lovedoing what I do, so I always
wanted to be doing it right andI wanted to be, you know,
utilizing new things and tryingnew things and all of this stuff
.
And so at one point in mybusiness I was basically
(18:19):
consumed with that and I wouldwork really late hours and you
know I would stay up all hoursat the night, wake up early to
record and like do all of thesethings right and That's a quick
way to burn out right, that is aquick, very quick and easy way
to burn out.
And so once I realized like Ineed to like take a step back
right, like let's take a stepback, let's prioritize.
(18:40):
How can I better serve myclients?
How can I better serve myselfwithout having to Like kill
myself by working all of thesehours and trying to do all of
the things right?
and so one of the ways of doingthat was really kind of looking
at My ideal day and my idealschedule and what I wanted that
(19:02):
to look like.
Right, because I want to havetime To spend with my son.
I want to have time to spendwith my husband and do fun
things and, again, i didn'tleave a nine to five to work
those types of hours.
I wanted flexibility in my dayright, where if I wanted to go
to the park at nine in themorning, i could go to park at
nine in the morning, right.
And so really the first step forme was kind of looking at my
(19:25):
schedule on my ideal day, likewhat did I want that to look
like?
how many calls did I want totake every day?
where there days I didn't wantto take calls, right?
So kind of looking at that andthen kind of puzzle, piecing it
together, right, and reallycreating the ideal day, the
ideal week, the ideal month.
What does that look like andwhat do I need to do?
What action do I need to takein order to hit my goals right?
(19:48):
what are the actual things thatThat are gonna make me money
that I need to prioritize overthings that might not bring in
any money right Or serve myclients in any way?
so that was kind of how Iapproached it.
Jessica Rosario (20:03):
Awesome,
awesome and and you are.
You seem to be somewhat of anature girl, right, so so you
like the outdoors, so is theresomething specifically that you
love to do when you're, whenpeople can't find you, behind a
click of dashboard?
Jena Paulo (20:19):
Yeah, for sure.
We're always out camping and inthe wilderness like not.
We're not really likeCampground kind of people or
people that take our off-roadingJeep and off-road into the
mountains and Literally have noservice.
So that's what.
That's where you'd find me.
Jessica Rosario (20:36):
Yeah, that's
kind of terrifying.
Jena Paulo (20:37):
You won't find me
there but that's awesome,
awesome, i love that.
Jessica Rosario (20:42):
So now I want
to spotlight a little bit about
you and how you can support Yourclients.
So for the woman that's juststarting out and obviously
there's some guys out there Soif there's a guy listening to
the podcast, kudos to you.
But but say there's someone outthere that's starting a
business and They don't you knowproject management or this type
(21:04):
of platform.
It didn't even cross their mind.
Is this something that you canrecommend from the startup?
Jena Paulo (21:13):
What I would first
recommend if you're starting to
look for a project managementtool for you that works
specifically for you.
You want to be able to go intothe tool and utilize it just
functionally, just very basic.
Be able to create a task, set adue date, assign it to yourself
(21:34):
.
You want to be able to do thoseeasy, functional things.
When you're thinking aboututilizing any kind of tool, the
easier and most simple it is thebetter, because you're more
likely to use it.
If you start to dabble and clickup and find that click up has
the simple functionalities thatyou can follow and you're
(21:56):
comfortable with that, click upis going to be the one that's
going to grow with your business.
You want something that's goingto grow.
If you go into Trello but youplan on being a million dollar
company in 10 years, that's notthe tool for you.
Really thinking about long-termwhen you're thinking about a
project management system, butbeing able to just utilize it in
(22:18):
its most foundational way sothat you get comfortable.
You don't want to dive in andstart trying to utilize all of
these more advanced features.
You want you to ease in slowly.
Jessica Rosario (22:33):
I love that.
Personally, i wish I would havestarted from day one, but also
knowing where I was mindset-wisefrom day one probably would not
have been the right time.
I love that you're sharing that, jenna.
how do you help businessesidentify areas of inefficiency
rather and areas of opportunityin their operations?
Jena Paulo (22:56):
Yeah, typically what
that looks like is we hop onto
a call and I really dive intoyour business, whether you're
already utilizing a projectmanagement tool or not.
I want to see the inside ofyour business and I want to pick
your brain.
I want to pull things out ofyour brain that maybe you didn't
even think were important ordidn't even know you had a
process for.
(23:17):
This is really high-levelauditing and consulting for
creating a plan, because I needto first understand how your
business works, what yourbusiness is, in order to give
you suggestions on how to buildout a tool that's going to
support you.
That's always the best.
First step is really doing anaudit type consultation.
(23:40):
We can understand the businessand then give you the action
items on how you can start toapply a tool like ClickUp.
Jessica Rosario (23:49):
Awesome.
How can someone work with you?
What are your current offerings?
Jena Paulo (23:55):
Yeah, i have a
handful of offerings.
One is a consulting hour.
You can purchase consultinghours just one off, or in bulk
Again.
This is where I would come intoyour system, audit your system,
do that kind of stuff.
But if you've already beenutilizing ClickUp, let's say,
and you're wanting to continueto improve it, you utilize a
(24:15):
session for that type of thingas well.
Then I also do larger buildouts.
Let's say that you're theperson who knows you need a
project management tool, butjust either don't have the time
or don't have the capacity orthe knowledge to build it out
yourself and you want an expertdoing that for you.
That's always an option as well.
(24:35):
This is more like a partnership.
We're really partneringtogether to create a system that
works for you.
It's very customized.
Then, if you are a ClickUpprofessional, i also offer
coaching and mentorship programsfor those types of
entrepreneurs as well.
Then I have a course, which youare a part of, level up with
ClickUp, which teaches you howto build it from start to finish
(24:58):
.
Jessica Rosario (24:59):
I love this
course.
I mean it was so good and youcan tell that you have a
background in education Becauseit was so good that I don't
think there's any reason whyanybody would take this course
and say I just didn't get it, ijust didn't know how to use it.
Because you're so patient andyou're so thorough in your
explanations and even in thevisuals, and being able to build
(25:20):
it exactly the way you have it,it was just an incredible
process.
I really loved it.
I still refer to it.
Jena Paulo (25:26):
I love hearing that
Great.
I love that With ClickUp 3.0coming out, there will be some
updates to level up eventually.
I just got access to 3.0, whichis very exciting.
I love that.
Jessica Rosario (25:40):
You know that's
funny.
It didn't even cross my mind,but, yes, i love that.
That's so exciting, awesome.
Yeah, they did a massive updateand I'm hearing great things
about it, so definitely forthose that are listening and
that are looking for a platformthat can grow with them.
Zero regrets We will neverleave ClickUp.
I mean ClickUp better.
Never leave us either, right.
Jena Paulo (26:01):
Yeah, I don't think
they plan to.
Jessica Rosario (26:03):
That's a great
platform And it's just really
helped us in scaling ourbusiness, growing our business
and just keeping thingsorganized.
I think the most importantthing has been team
communication, too to be able tocommunicate with our team and
see where certain tasks are andwhat's pending and whatnot.
So that's been really great.
So, jenna, how can people findyou.
Jena Paulo (26:22):
Yeah, so if you are
interested in learning more
about ClickUp, you can join meinside of my Facebook group.
It's called ClickUp forEntrepreneurs And I offer tons
and tons of tips and tricksinside of that group, as well as
free trainings and inside looksand all of that fun stuff
inside of the group.
So I'll pass that Facebookgroup link along to you And then
(26:44):
also you can find me onInstagram at the Jenna Apollo.
Jessica Rosario (26:49):
Awesome,
awesome.
I love that.
For those of you that aredriving, those links will be
listed on the show notes, Sofeel free to check them out
there and feel free to connectwith her directly Now.
Jenna, as we wrap up ourepisode here today, tell me how
do you maximize your day?
Jena Paulo (27:08):
Yeah, love that.
So I maximize my day by doing afew things.
First, i utilize ClickUp toprioritize my tasks, and the
second thing I do is I ensurethat my day is structured the
way that it's going to be mostproductive for me.
So I would say that I'm notsuper, super productive early in
(27:30):
the morning I'm more of a nightperson or later in the
afternoon.
So all of my priorities andtasks that might be more
difficult or more challenging, iutilize the time where I'm most
focused to accomplish thosethings.
So the morning's not for me,but later in the day is, and so
that's kind of how I prioritizeand maximize my day.
Jessica Rosario (27:52):
Awesome,
awesome.
I love that.
Well, you guys, there you haveit.
I mean, we had the Jenna Apolloon our show.
I'm so excited to be able toair this episode And if it
impacts or helps one person,then we've done our job on who
we've been called on the surf toserve.
So excited to be able to sharethis time with you and get to
(28:12):
know a little bit more about youAnd just look forward to
continue watching your growthand continue to work with you as
we move forward.
Jena Paulo (28:21):
Yes, thank you, and
thank you so much for having me.
Jessica Rosario (28:24):
As always.
thank you so much for listeningin.
Don't forget to subscribe tothe show to be notified the
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(28:45):
be a guest on my show.
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