October 13, 2025 • 30 mins
Tarra Stubbins shares her journey from dropping out of high school to travel with rock bands as a personal assistant—including wild hotel room requests from Mick Jagger—to founding the Take It Easy Group, where she now provides Chief of Staff and executive support to high-profile clients. She talks about handling unusual demands like putting a toothbrush in a hotel dishwasher, building a strong network, and helping CEOs, athletes, and high-net-worth individuals manage their complex lives. Tarra also discusses her new podcast "Fuck the Fluff," focused on real, no-nonsense advice for women in business.
Links Mentioned:
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- Strategic Planning Checklist
- Chief of Staff Skills Assessment Checklist
- A Day in the Life of a Chief of Staff
- Chief of Staff Toolkit
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Who Am I?
If we haven’t yet before - Hi👋 I’m Emily, Chief of Staff turned Executive Leadership Coach. After a thrilling ride up the corporate ladder, I’m focusing on what I love - working with people to realize their professional and personal goals. Through my videos here on this channel, books, podcast guest spots, and newsletter, I share new ideas and practical and tactical tools to help you be more productive and build the career and life you want.
Time Stamps:
00:35 Tarra's Early Dreams and Career Beginnings
02:12 First Steps into the Rock and Roll World
03:39 Life on Tour with Rock Stars
04:54 Crazy Requests and Problem Solving
06:44 Mental and Physical Preparation for Performers
12:06 Transitioning from Roadie to Entrepreneur
14:58 Building a Personal Concierge Business
16:20 Managing High Net Worth Individuals
18:48 The Importance of Networking
20:27 Take It Easy Group's Services and Clients
28:07 New Podcast and Final Thoughts
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
emily-sander_1_06-11-2025_ (00:25):
Tara Stubbins, welcome to Leveraging
Leadership.
Thank you so much for being onthe show.
tarra_1_06-11-2025_113326 (00:30):
Thank you so much for having me.
I'm so excited to have thisconversation.
emily-sander_1_06-11-2025_08 (00:34):
am too.
I am too.
So I often refer to chiefs ofstaff as like the rock star of
the team.
You kind of bring a whole newdefinition to that.
You were, you are the founder ofTake It Easy group now, but how
you got there is kind ofinteresting.
You were chief of staff toactual rock stars.
So can you please give us alittle snapshot of that
(00:56):
backstory?
tarra_1_06-11-2025_113326 (00:57):
Yeah, so, uh, taking you way back to
when I was really little, Ialways had this dream that I
wanted to be a rock star, butfor some reason, um, I like, you
know, always thought or I wantedto be a star, but for some
reason in my head, I alwaysthought that being a star was
being a rock star.
(01:19):
I had very, and I still havevery little musical talent.
I, you know, love music andappreciate music, but when I
play a musical instrument, itsounds like a dying animal.
So I was like, well, there goesthat dream.
Um, but something inside me toldme not to throw away my entire
(01:39):
dream.
And that's like a little nuggetthat I always love to tell
people is that from all thereally successful people that I
have been able to work with andsurround myself with, if you
listen to their back stories,they always kind of knew where
they were going or had a littleidea, like a little nugget in
them, um, of where they're gonnago.
(02:01):
So.
Please don't throw away yourdream if you're really, you
know, trying to do something andyou think this is never going to
be for me.
That's like a little tiny pieceof advice that I love to share
with everybody.
Um, so yeah, I had this likelittle, uh, of my dream that I
held on to, and I al I wouldforget about it until those days
when you had to make a bigdecision like, am I going this
(02:24):
way or am I going this way inlife?
And, uh, one of those days was,uh, when I was, do I continue
with school or do I jump on arock and roll tour bus?
emily-sander_1_06-11-2025_ (02:35):
Hey.
tarra_1_06-11-2025_113326 (02:35):
And so I decided to drop outta high
school and jump on a rock androll tour bus.
Now I am not, uh, tellingeverybody to do that, to follow
their dreams.
My mother almost killed me.
It was in the days before cellphones.
It wasn't probably a gooddecision, but I did it anyway.
Um.
(02:56):
And I became, I fell in lovewith, you know, just like the
grunt work of being anassistant.
It wasn't even, there was noflashiness to what I was doing.
There was, there was nothing.
It was a very unknown band goingacross Canada.
I.
And so, you know, but it washelping people and helping them
live out their dreams that Ijust gravitated to and loved
(03:20):
every minute of it.
And I was like, this is what Iwanna do.
This is how I wanna be the rockstar.
I wanna help rock stars.
And so I did that to her.
I went back to school and afterschool I jumped on another rock
and roll tour bus and have beenchasing rock stars around ever
since.
emily-sander_1_06-11-2025_08 (03:39):
So you, so when you say chasing
rock stars, like you've traveledlike 300 days out of the year,
like you, you're a roadie.
Like what types of things areyou able to share about that
experience?
tarra_1_06-11-2025_113326 (03:49):
Yeah, so
emily-sander_1_06-11-2025_08 (03:51):
I.
tarra_1_06-11-2025_113326 (03:51):
of the big names that I got to
support were the Rolling Stonesand Mick Jagger, I was his.
personal assistant out on theroad for two world tours.
emily-sander_1_06-11-2025_ (04:04):
Wow.
tarra_1_06-11-2025_113326 (04:04):
that was like 250 to 300 days a year.
Not at home on, you know,planes, buses, in hotel rooms,
um, just.
Chasing him wherever he wasgoing.
Uh, and I had to basically makesure that he was set up both
(04:25):
mentally and also physically ina space and, you know, a mindset
where he could.
Go out and play the best darnshow every single night for all
of us.
Um, and there was crazyexperiences.
Uh, a lot of them I can't share.
Obviously we all know as chiefsof staff, we have, um, you know,
(04:46):
confidentiality agreements, butone that I do share quite a bit,
um.
And there's also a little kindalearning, uh, nugget in there as
well.
But, uh, he would always wanthis hotel rooms painted a very
specific shade of beigeeverywhere we went.
Actually, very similar to thebeige on the wall behind me.
(05:06):
And no, I didn't copy him.
I actually kind of have PDSDabout this color.
So, um, but yeah, I'm justrandomly in this room, but he,
so we would be everywhere.
We were in one time in.
Mumbai in the Taj Mahal Hoteland the Taj Mahal Hotel is.
Very old.
It's thousands of years old, andin the presidential suite where
(05:30):
he was staying, there's goldleaf wallpaper on the walls.
And what we had to do was we hadto take that ancient gold leaf
wallpaper down and
emily-sander_1_06-11-2025_08 (05:39):
Oh
tarra_1_06-11-2025_113326 (05:39):
the
emily-sander_1_06-11-2025_0 (05:40):
no.
tarra_1_06-11-2025_11332 (05:40):
beige.
And then he stayed there forthree days and then we restored
the wallpaper and put it back upand continued on our way to the
next city.
Um, but yeah, crazy things likethat was what I had to do.
I learned, um, very early on.
You never ask rock stars whythey do crazy stuff.
(06:01):
You just don't wanna know.
I got very good at saying yes, Iwill figure it out, even though
I was panicking on the inside.
It was, um, days again beforelike cell phones really, or you
know, I couldn't really Googleor Uber my way out of problems.
(06:21):
It was.
trying to figure out how am Igoing to get this request or
solve this problem.
Um, so yeah.
And, and they never wanna hear.
No.
So it was, yep.
Okay.
I'll get it.
Sure.
12 hours, no problem.
And then, yeah, panicking on theinside, so it was great problem
solving skills as well.
emily-sander_1_06-11-2025_ (06:42):
Wow.
Oh my gosh.
Okay.
There's a lot to unpack there,but I'm just curious, um, what
does it take to get Mick Jaggeror just like a rock star in
general, like mentally andphysically ready to go on stage
and perform like you have to beon.
Thousands and thousands andmillions of people have paid
good money to come and see you.
So you, you can't be halfwaythere.
(07:02):
So what, can you talk about afew things you've, you've
learned there?
tarra_1_06-11-2025_113326 (07:06):
Yeah, so with people like Mick Jagger
and the Rolling Stones, they'vebeen famous for like 375 years.
So they, they, they just know,it's just kind of what they do.
But if you think about youngerpeople
emily-sander_1_06-11-2025_08 (07:21):
I.
tarra_1_06-11-2025_11332 (07:21):
people who are just getting to like the
top of their game.
There's a lot that goes intotheir, like, as I was saying,
mental readiness as well asphysical readiness.
So we always hear about like thecrazy requests, like the, you
know, beige walls, or there's afamous one where Van Hale and
asked people to pick Brown m andms out of the, um, of their,
(07:44):
they never wanted to see Brown mand msms in their tour bus, but
that was because they wanted tomake sure people actually read
the list and were doingeverything on the list.
So it was like a trick, but.
of them having to stress out,like have my actual requests
that make me feel comfortableand ready to get on stage and
(08:05):
perform, been, you know,succeeded and been checked off
the list.
They don't have to worry aboutthat anymore.
They just see the brown m andmss and they're like, okay, it,
it has or it hasn't.
That was their kind of.
Crazy version of just beingmentally prepared.
Uh, again, I never asked MickJagger why he wanted his rooms
painted beige, but.
(08:26):
I can kind of take, I, I thinksome of it was OCD, some of it
was just a request that kind ofcarried on.
Um, you know, from the earlybeginnings.
Maybe it started as a joke, I'mnot quite sure, but it was
something that he could feelcomfortable in.
We were, you know, in adifferent room almost every
night in different cities, andthat's a lot of.
(08:48):
Just, you know, strange pla andunknown places.
And for anyone who has traveledit is, it takes a couple of
seconds when you get into yourhotel room, even if you're
traveling for work and you'relike, okay, I'm gonna work now.
But I just need to kind ofsettle in and, you know, kind of
feel up the space a little bit.
And that was something that hecould just, you know, walk into
(09:09):
the room and it felt the sameeverywhere he went, no matter
where it was.
And then he could, you know,prepare and do whatever he
wanted.
He loved running on treadmills,um, wherever he was.
So he could do that, but he justdidn't have to think about it.
And that.
Another real key aspect that Ialways like to talk about is
like, if you're really trying tobuild success in your business
(09:31):
or your role, um, getting rid ofthose habits that you always
have to think about and makingthem just something that you
don't even have to think aboutand you just do, and those
habits that actually drive succesuccess, that's where successful
people actually becomesuccessful and famous and the
rock stars because they don'tthink about those habits.
(09:52):
It's just something that theydo.
emily-sander_1_06-11-2025 (09:53):
Yeah, and I think, I mean, a Chief of
Staff's job is to create thatspace for their principals, and
it is like, you know, we're talkabout decision fatigue, where
it's like, take the unnecessarydecisions off of their plate.
They have to make a few.
High quality decisions each day,like you gotta tee'em up for
that.
And I think these, these kindof.
Extra habits, just like havethat built in for them.
(10:14):
So I love that.
And then just, I was on thephysical side of preparing.
I remember watching this littlelike featurette on Lady Gaga for
her Super Bowl performance,which was amazing by the way.
Like that's one of the bestperformances in recent memory in
my opinion.
But she.
Was talking to her team and shehad to have like the, I think it
was like the gimbal thing thatshe was like flying across the,
(10:37):
across the sky on like set up ina certain way.
And she was like, I just want itthis way.
I know it sounds weird, but I'mlike, you're flying across like
open air and you could die.
So if you want that prepped acertain way, you can.
And then I remember she was infull costume.
She got in her full costume andshe would go on one of those
like, I dunno what they'recalled, but those machines where
you move your arms and legs uplike a pole and you're like,
(10:57):
you're climbing.
And she would sing.
Her song while she was doingthat, and I was like, what in
the world?
So there's like a me, like aphysical aspect of being
prepared too.
tarra_1_06-11-2025_11332 (11:08):
Taylor Swift is known for that.
She would run on her treadmilland do her entire Aris
performance four
emily-sander_1_06-11-202 (11:16):
That's crazy.
tarra_1_06-11-2025_113326 (11:16):
it is while running.
But you can think about thephysical stamina that these
artists.
Need to not only emotionallyhold the crowd, but also
physically run around the stageand sing.
And you know, some of them playguitar or an instrument, like
it's both.
It's physical and mental workthat they are doing up
emily-sander_1_06-11-2025 (11:38):
Yeah, totally.
And Lady Gaga dances too.
So anyway, I just remember thatI was like, yeah, there is so
much prep that goes into that.
And I think, you know, certainlyI.
Different in like businessworld, but you still have to
think about the health and thephysical fitness of your
principal because they might notbe going on tour, but they might
be traveling 250 days outta theyear.
They might be giving largepresentations to the media, to
(12:00):
the public, to their staff.
So I think all of that comesinto play.
Um, all right.
So how did you kind oftransition from roadie
lifestyle, uh, chief of staff tothe rock stars to what you're
doing now?
tarra_1_06-11-2025_113326 (12:13):
Yeah, so it was a big kind of aha
moment I had so.
Even back when I first jumped onthat first tour bus and I
realized that I just wanted tohelp people achieve their own
dreams.
Um, that was always in the backof my head.
And this one rock star, I'm notallowed to name who it was, but
he would always ask me, um, to,he had this crazy request that
(12:38):
every time we traveled and gotto a new hotel room, he wanted
his.
Toothbrush to be taken out ofthe suitcase and to be sanitized
in a hotel dishwasher.
So industrial, sanitized histoothbrush.
emily-sander_1_06-11-2025_ (12:53):
Wow.
tarra_1_06-11-2025_113326 (12:53):
Um, and so I always get asked like,
one, did you do it?
And I was like, yeah, actually Idid do it.
I didn't even think of her notdoing it.
And two, like, why didn't youjust buy a new toothbrush?
And I, I don't know, again,didn't ask, but that was.
One of the requests.
So a lot of times we'd be inhotels that we'd stayed in
before and they would recognizeme coming and they'd be like, oh
(13:16):
yeah, here's this crazy ladywith the toothbrush again.
Um, but sometimes we'd be inhotels that were new or in a new
city that we'd never played in.
And so I had to, you know, a lot
emily-sander_1_06-11-2025 (13:27):
It's.
tarra_1_06-11-2025_113326 (13:27):
I would try to prepare, but a lot
of times it's kind of hard tocall ahead and be like, I'm
putting a toothbrush in adishwasher.
So it was a almost a spur of themoment type thing.
we were in Shanghai and I wastrying to put this toothbrush in
the dishwasher, and I was likein the back with the staff and I
(13:49):
didn't speak their language,they didn't speak English, and I
was just, you know, trying tomake gestures with this
toothbrush to put it in thedishwasher.
And they were looking at me likeI had three heads.
Again, back in the day beforethere was like Google Translator
or anything, um, and I didn'treally have a translator with me
and.
emily-sander_1_06-11-2025_08 (14:08):
If you have a strange lady coming,
bringing a toothbrush in thedishwasher hotel, that's the.
tarra_1_06-11-2025_113326 (14:14):
Yeah, what is happening?
I don't blame them.
and I just remember standingthere with toothbrush in hand
thinking, there's gotta be moreto life than this.
And I realized that I, I reallyloved helping people and I
wanted to help people.
And, you know, tasks, likeputting toothbrushes in
dishwashers, I didn't reallycare about that, but I really
(14:35):
wanted to be able to help.
One more than one crazy rockstarat a time.
And I thought, well, why don't Ijust come off the road and just,
I don't know what I'm gonna do,but you know, there's gotta be a
way for me to just help morethan one person achieve their
goals.
Me running around the worldafter one person isn't, you
(14:56):
know, expanding this process.
So in 2007, I came off the roadwith just this dream.
I had no idea what I was doing.
I had no business background.
I, yeah, no idea.
Um, and my network, of coursewas like a lot of high profile,
high net worth individuals.
I started managing their homesand I started basically doing
(15:17):
what I was doing.
on the road, but just for themlocally in, in Toronto.
Um, and that grew into abusiness after that.
So it, uh, still running a kindof personal concierge, personal
lifestyle management company,um, across Canada and the us.
But as I was doing that, I alsorealized that there was, there
(15:38):
was more people we could help aswell.
Not just running their homes,but running like their calendars
and their.
Full.
I always say like managing themas a person and not necessarily
just personal or just business.
It's like them as a whole.
And I realized that that's whatwe were basically doing, running
their household.
(15:59):
'cause their business wouldalways fall into it as well.
Um, so then moved the businessfor Take it Easy, more into that
Chief of staff, fractional chiefof staff, fractional executive
assistant space.
emily-sander_1_06-11-2025_ (16:10):
Wow.
Okay.
I love your tenacity where it'slike, I have no background in
this, but I'm gonna jump in andfigure it out.
And then you do, that's, that'strademark chief of staff.
Love it.
Um.
So when you talk about like highnet worth individuals and
running their entire household,like all aspects of their life,
I mean, I can imagine what thatwould be like for me, but I
(16:30):
think you're talking about like,I like to buy that island, or I
wanna go like get thatrestaurant or whatever.
Like what types of things doesthat entail?
tarra_1_06-11-2025_113326 (16:39):
we talked about this before and I
have a funny story about onevery high net worth individual,
um, in Toronto, probably one ofthe most famous Canadian
musicians, and there was a.
Store, uh, a restaurant like amom and pop Jamaican Patty
restaurant closing.
It was kind of famous and it wasall over the news that it was
(17:01):
closing.
They were retiring.
Um, and, you know, people ofToronto didn't want this
restaurant to close.
And so this, my client was like,oh, uh, I need you.
He calls me up and he is like,can you just go buy this
restaurant on my Amex?
And I was like.
emily-sander_1_06-11-2025_08 (17:19):
As you do, you know.
tarra_1_06-11-2025_113326 (17:21):
I was like, no, no, I can't.
What goes in his mind is, butthere's an unlimited spend on
it.
And I'm like, yep, nope, that's,that's not the problem.
But you know, of course I willfigure it out and we will buy
this restaurant.
There's just a couple moreprocesses than handing over an
Amex.
Card.
Um, so yeah, so managing theirlives is managing just all those
(17:46):
crazy ideas that come into theirhead.
Um, also their staff.
So they have a lot of, you know,cleaners on staff and people,
gardeners, um, valets drivers,depending on how large their
properties are.
A lot of them have multipleproperties, so when they decide
to, you know, go off to.
(18:08):
Wherever their second or thirdhome is, making sure that it's
stocked, that the staff is readyto go for their arrival, if
they're having guests that youknow, the guests are comfortable
and they're ready.
So just making sure again, thatthey are ready and prepared
physically and mentally as well.
emily-sander_1_06-11-2025_ (18:26):
Wow.
And so like how do you, um, howdo you personally build trust
with these folks?
Or you have, you just alreadyknown them so they trust you.
And then a secondary questionis, I.
Like, how do you build out theirteam, like the, the lawn people
and the cleaners, and I'mimagining personal trainers and
personal chefs and all thesepeople around them.
How do you make them feelcomfortable with, with those
(18:47):
staff members as well?
tarra_1_06-11-2025_113326 (18:48):
so I am a huge believer and you are
only as successful as yournetwork and from back in the day
when I was having to go get allthese crazy requests like.
Oh, I wanna have a party and Iwanna have a live goat in the
hotel room.
For some reason, rock stars likegoats and parties.
I don't know why.
Um, but you know, like it waslike, okay, who can I call?
(19:11):
Who's the, you know, farmer inthis city that I need to call?
Um, so, you know, I would neverbe able to have gotten anywhere
without the connections and therelationships that I built that
I could lean on when I was inthe city, or I could lean on for
their connections.
Obviously, know, you can't just,it can't go one way.
(19:32):
So we would always give themlike free concert tickets or
whatever they want.
Signatures backstage passes,whatever they wanted.
Um, but yeah, so I learned veryearly on that the.
I could only get so far bymyself, and that's what I took
into when I opened my business.
And again, had zero businessbackground at all.
But I, and I was like, I don'tknow how to go out and get a
(19:54):
client.
Maybe I should just call thisperson.
And then I realized, oh, myclients are actually here
through my network anyway.
So I know it's kind of a copout,um, conversation, especially for
people who are like, I don'thave a network yet, which is
totally fair.
Um, but I, I truly believe thatif you want to get to a certain
place in your business or yourcareer, you should start
(20:17):
building your network.
If you don't have it now, youshould start, um, building it to
a point where it is, you canlean on it for whatever you
need.
emily-sander_1_06-11-2025 (20:27):
Yeah.
So, um, can you talk a littlebit more about who take it?
Easy group helps.
So you mentioned high net worthindividuals is, are these like
entertainment folks?
Are these in the sports world?
Any high net worth?
What, what does that look like?
tarra_1_06-11-2025_113326 (20:38):
Yeah, so really any high net worth,
ultra net worth individual whohas multiple businesses.
Um, a lot of people come to usfrom, and I don't just mean
multiple businesses, but I meanlike multiple things on the go.
So businesses, philanthropy, youknow, a family office.
Like just they need that chiefof staff running their entire
(21:00):
life and not just necessarilytheir business or their charity
arm or whatever it is.
Um, so those types of people,and again, just because that's
kind of my network that I havealways been around, we have a
lot of former athletes that cometo us.
I think because they reallyunderstand the power of an
assistant and it's not aconversation of, you know, you
(21:24):
need a conversation, but it'slike how strategic of an
assistant you actually need,which is really interesting to
me.
Um, and they have a lot ofpersonal assistance, but the
personal assistants are amazing.
It's.
It's my background.
I'm not putting down personalassistance at all, but they just
don't necessarily have thatbusiness, um, mindset as well.
So they need someone who canhelp with the business and the
(21:46):
personal assistance are great tohelp with, you know, manage
their lives on that side.
so yeah, a lot of formerathletes and then just a lot of
just high growth founders,people who are building really
cool things.
You don't have to be acelebrity, you don't have to be
ultra high net worth or high networth, but if you have a really,
really cool idea and you havethat passion and drive behind
(22:09):
you, that you understand thatyou need that strategic support,
we're a good partner for you.
emily-sander_1_06-11-2025_ (22:15):
Love it.
Yeah.
And I love the fact that itsounds like when you're
successful, you just have anunderstanding.
You need this strategic supportlike you, like you will not be
able to do what you can dowithout it.
And I think, like I have so manyconversations about like, what
is the chief of staff?
What, why is the chief of staff,do you really need a chief?
I'm like, if you wanna.
(22:37):
Take it to the next level.
If you wanna be top of yourfield, then yes.
If you don't, then like, sure,go ahead and don't have one.
Um, so I love that, like you're,what I'm hearing is these people
just know that and they're justlike, okay, what, who am I gonna
get?
How strategic are they gonna be?
And I'm curious too, if theyalready have like a team of
personal assistance, do you comein and work with that existing
(22:57):
team?
Uh, do you bring in like yourown staff?
How does that typically work?
tarra_1_06-11-2025_113326 (23:01):
It depends.
Um, I am not here to takeanybody out of a job at all.
So, um, absolutely happy to workwith, um, who, whoever their
team is, even if they have chiefof staff.
We've come in and helped people,uh, on a contract basis.
And when the chief of staff, aswe all know,'cause I know you
have mostly chief of stafflistening, we, our jobs, our day
(23:23):
to day are packed.
And then somebody tells us, oh,there's this massive project now
we have to do, or a new launch,or we're opening up in a new
country or a city.
And you're like, how the heck amI gonna get that off my plate or
fit that into my schedule?
Um, so we've come in and helped,uh, on a contract basis just be
(23:43):
that second right hand person,um, to really be able to help
bring those projects to life andget them across the finish line.
emily-sander_1_06-11-2025_0 (23:52):
And if you, if they want someone to
like, design their team ordesign their support system,
I'm, I'm like thinking of anexample, like I have a charity
and I have like a real estatebusiness and I have multiple
homes, like you say, okay, letme get some.
One, to kind of be the managerof the, the, the house, the home
situation, and then let me findsomeone to spearhead the
(24:12):
philanthropy, the charity piece,blah, blah, blah.
And then you kind of orchestratethe whole thing.
Is that how it works or is thatdifferent?
tarra_1_06-11-2025_113326 (24:18):
Yeah, sometimes, again, it depends on
the situation, so sometimes theyjust need, like, they need
multiple people in eachorganization because they have
tons of projects going on.
Sometimes they just need onevery strategic person at the
head of everything.
Who can delegate out to usuallyteams that are already in place,
(24:39):
um, for, you know, philanthropicefforts and a business launch
and whatever that they're doing.
So again, it depends on thesituation, but.
I know we've talked about it andI'm sure you'll have lots of
conversations about thedefinition of a chief of staff
and they, you know, it can beanything these days really.
Um, and for us and what we do,it's a lot of that strategic
(25:03):
project management support andteam alignment with
administrative help as well,just because that's my
background.
Um, but that's kind of how wefall into helping manage all
those different arms.
emily-sander_1_06-11-2025 (25:17):
Yeah.
And are you.
I mean, are you personallybecoming chief of staff to all
these folks and then popping outto another engagement?
Or do you have like a team ofpeople that you place?
How does that work?
tarra_1_06-11-2025_113326 (25:28):
So if I was doing it all, um, I would
not be here.
I'd be dead probably.
There's definitely not enoughhours in the day for that.
Um, yes, I have a team ofwonderful full-time, so they're
full-time with me with Take ItEasy.
Chief of Staff and ExecutiveAssistants.
Um, that we then contract outor, uh, partner out with
(25:52):
multiple clients depending onthe engagement and the level of
engagement.
Uh, so it's our responsibilityat take it easy to find them,
the clients, and it's theirresponsibility to kind of live
up to the, take it easyexpectations of how they, uh,
partner and work with theclients.
emily-sander_1_06-11-2025_ (26:10):
Wow.
Okay.
Okay.
So if someone's listening, whattype of, what type of folks or
background or just like traitsand like character assets would
you need?
I.
tarra_1_06-11-2025_113326 (26:19):
Yes.
So, um, being able to understandthe lifestyles of, uh, you know,
high net worth individuals andultra high net worth individuals
is really important becausethey're, they're.
is just the way they think andoperate is very different than,
say, a founder, um, who has alot of big goals.
(26:40):
So understanding that, um,having experience in the startup
space as well as corporate isreally helpful because it, um.
It just helps you work acrossboth the functions that we
usually get clients in and thestartup space.
I find that you can run a lotfaster and just understand that
(27:02):
chaos is always a thing.
Um, so that's really helpful.
The, we do a lot of testingaround proactive and strategic
thinking, so if you're aproactive strategic thinker, we
would love, actually I'm hiringright now, so if anyone is
listening.
Please, uh, go to my LinkedIn.
We can put a note to the bottomand, uh, send me your resume.
(27:25):
Um, but yeah, proactive thinkersare really important as well.
Um, and yeah, anyone who justlikes to work with a, we're very
collaborative on the Take ItEasy team.
Um, we love to have fun.
We went on our team trip thisyear to Coachella.
Um, very important to have thatmusic background.
Um, so yeah, we, we are like afun collaborative, not very
(27:48):
corporate team, um, but thenbeing able to kind of like put
on that face for the clients aswell.
emily-sander_1_06-11 (27:55):
Beautiful.
And we will have that LinkedInlink in the show notes.
And then is there a website oranything you wanna point people
to to learn more?
tarra_1_06-11-2025_113326 (28:02):
Yeah, take it easy.
group.com is where you can findeverything.
emily-sander_1_06-11 (28:07):
Beautiful.
And what is your new podcastabout?
tarra_1_06-11-2025_113326 (28:09):
Oh, can I swear on this podcast?
emily-sander_1_06-11-2025_ (28:12):
can.
tarra_1_06-11-2025_113326 (28:13):
Okay, so the podcast is called Fuck
the Fluff, and it is um, well alittle backstory again'cause I
like backstories.
Um, but I was getting kind offrustrated with the fluffy
advice that is always kind ofput out on podcasts.
(28:34):
And as you can hear in what I'vebeen trying to talk about and
share stories is I like to giveactual.
Takeaways and as I call themnuggets, um, for people to be
able to go, oh yeah, I'm havingthat problem, or I can see that,
how I can get that out of it.
Whereas a lot of times peopleespecially like, you know,
pretty famous people or peoplewho do those like podcast
(28:56):
circuits, you'll hear, oh yeah,I went from living on the street
to being a billionaire.
And you're like, well, that'sgreat.
Like how did you,
emily-sander_1_06-11-2025 (29:04):
Yeah.
tarra_1_06-11-2025_113326 (29:04):
the steps?
That you actually took and thenyou hear a lot, oh, I manifested
it.
Um, and it's like, no, like youactually had to do something to
get there, or else we'd have alot more billionaire, uh, you
know, entrepreneurs in our, inour world.
Um, so I just really wanted toshare.
I.
The like non fluffy advice ofactually how to build success.
(29:27):
Um, I love talking to femalefounders, female entrepreneurs,
female business owners who havebeen through really shitty times
as we all have in running ourbusinesses, and can share that,
that non fluffy advice on howthey got through to the other
side.
emily-sander_1_06-11-202 (29:46):
That's awesome.
Okay.
We'll have any of thatinformation in the show notes as
well.
But um, Tara, thank you so muchfor being on the show.
Thank you for sharing somereally fun stories and really
appreciate you and what you'redoing
Tara Stubbins, welcome to Leveraging
Leadership.
Thank you so much for being onthe show.
tarra_1_06-11-2025_113326 (00:30):
Thank you so much for having me.
I'm so excited to have thisconversation.
emily-sander_1_06-11-2025_08 (00:34):
am too.
I am too.
So I often refer to chiefs ofstaff as like the rock star of
the team.
You kind of bring a whole newdefinition to that.
You were, you are the founder ofTake It Easy group now, but how
you got there is kind ofinteresting.
You were chief of staff toactual rock stars.
So can you please give us alittle snapshot of that
(00:56):
backstory?
tarra_1_06-11-2025_113326 (00:57):
Yeah, so, uh, taking you way back to
when I was really little, Ialways had this dream that I
wanted to be a rock star, butfor some reason, um, I like, you
know, always thought or I wantedto be a star, but for some
reason in my head, I alwaysthought that being a star was
being a rock star.
(01:19):
I had very, and I still havevery little musical talent.
I, you know, love music andappreciate music, but when I
play a musical instrument, itsounds like a dying animal.
So I was like, well, there goesthat dream.
Um, but something inside me toldme not to throw away my entire
(01:39):
dream.
And that's like a little nuggetthat I always love to tell
people is that from all thereally successful people that I
have been able to work with andsurround myself with, if you
listen to their back stories,they always kind of knew where
they were going or had a littleidea, like a little nugget in
them, um, of where they're gonnago.
(02:01):
So.
Please don't throw away yourdream if you're really, you
know, trying to do something andyou think this is never going to
be for me.
That's like a little tiny pieceof advice that I love to share
with everybody.
Um, so yeah, I had this likelittle, uh, of my dream that I
held on to, and I al I wouldforget about it until those days
when you had to make a bigdecision like, am I going this
(02:24):
way or am I going this way inlife?
And, uh, one of those days was,uh, when I was, do I continue
with school or do I jump on arock and roll tour bus?
emily-sander_1_06-11-2025_ (02:35):
Hey.
tarra_1_06-11-2025_113326 (02:35):
And so I decided to drop outta high
school and jump on a rock androll tour bus.
Now I am not, uh, tellingeverybody to do that, to follow
their dreams.
My mother almost killed me.
It was in the days before cellphones.
It wasn't probably a gooddecision, but I did it anyway.
Um.
(02:56):
And I became, I fell in lovewith, you know, just like the
grunt work of being anassistant.
It wasn't even, there was noflashiness to what I was doing.
There was, there was nothing.
It was a very unknown band goingacross Canada.
I.
And so, you know, but it washelping people and helping them
live out their dreams that Ijust gravitated to and loved
(03:20):
every minute of it.
And I was like, this is what Iwanna do.
This is how I wanna be the rockstar.
I wanna help rock stars.
And so I did that to her.
I went back to school and afterschool I jumped on another rock
and roll tour bus and have beenchasing rock stars around ever
since.
emily-sander_1_06-11-2025_08 (03:39):
So you, so when you say chasing
rock stars, like you've traveledlike 300 days out of the year,
like you, you're a roadie.
Like what types of things areyou able to share about that
experience?
tarra_1_06-11-2025_113326 (03:49):
Yeah, so
emily-sander_1_06-11-2025_08 (03:51):
I.
tarra_1_06-11-2025_113326 (03:51):
of the big names that I got to
support were the Rolling Stonesand Mick Jagger, I was his.
personal assistant out on theroad for two world tours.
emily-sander_1_06-11-2025_ (04:04):
Wow.
tarra_1_06-11-2025_113326 (04:04):
that was like 250 to 300 days a year.
Not at home on, you know,planes, buses, in hotel rooms,
um, just.
Chasing him wherever he wasgoing.
Uh, and I had to basically makesure that he was set up both
(04:25):
mentally and also physically ina space and, you know, a mindset
where he could.
Go out and play the best darnshow every single night for all
of us.
Um, and there was crazyexperiences.
Uh, a lot of them I can't share.
Obviously we all know as chiefsof staff, we have, um, you know,
(04:46):
confidentiality agreements, butone that I do share quite a bit,
um.
And there's also a little kindalearning, uh, nugget in there as
well.
But, uh, he would always wanthis hotel rooms painted a very
specific shade of beigeeverywhere we went.
Actually, very similar to thebeige on the wall behind me.
(05:06):
And no, I didn't copy him.
I actually kind of have PDSDabout this color.
So, um, but yeah, I'm justrandomly in this room, but he,
so we would be everywhere.
We were in one time in.
Mumbai in the Taj Mahal Hoteland the Taj Mahal Hotel is.
Very old.
It's thousands of years old, andin the presidential suite where
(05:30):
he was staying, there's goldleaf wallpaper on the walls.
And what we had to do was we hadto take that ancient gold leaf
wallpaper down and
emily-sander_1_06-11-2025_08 (05:39):
Oh
tarra_1_06-11-2025_113326 (05:39):
the
emily-sander_1_06-11-2025_0 (05:40):
no.
tarra_1_06-11-2025_11332 (05:40):
beige.
And then he stayed there forthree days and then we restored
the wallpaper and put it back upand continued on our way to the
next city.
Um, but yeah, crazy things likethat was what I had to do.
I learned, um, very early on.
You never ask rock stars whythey do crazy stuff.
(06:01):
You just don't wanna know.
I got very good at saying yes, Iwill figure it out, even though
I was panicking on the inside.
It was, um, days again beforelike cell phones really, or you
know, I couldn't really Googleor Uber my way out of problems.
(06:21):
It was.
trying to figure out how am Igoing to get this request or
solve this problem.
Um, so yeah.
And, and they never wanna hear.
No.
So it was, yep.
Okay.
I'll get it.
Sure.
12 hours, no problem.
And then, yeah, panicking on theinside, so it was great problem
solving skills as well.
emily-sander_1_06-11-2025_ (06:42):
Wow.
Oh my gosh.
Okay.
There's a lot to unpack there,but I'm just curious, um, what
does it take to get Mick Jaggeror just like a rock star in
general, like mentally andphysically ready to go on stage
and perform like you have to beon.
Thousands and thousands andmillions of people have paid
good money to come and see you.
So you, you can't be halfwaythere.
(07:02):
So what, can you talk about afew things you've, you've
learned there?
tarra_1_06-11-2025_113326 (07:06):
Yeah, so with people like Mick Jagger
and the Rolling Stones, they'vebeen famous for like 375 years.
So they, they, they just know,it's just kind of what they do.
But if you think about youngerpeople
emily-sander_1_06-11-2025_08 (07:21):
I.
tarra_1_06-11-2025_11332 (07:21):
people who are just getting to like the
top of their game.
There's a lot that goes intotheir, like, as I was saying,
mental readiness as well asphysical readiness.
So we always hear about like thecrazy requests, like the, you
know, beige walls, or there's afamous one where Van Hale and
asked people to pick Brown m andms out of the, um, of their,
(07:44):
they never wanted to see Brown mand msms in their tour bus, but
that was because they wanted tomake sure people actually read
the list and were doingeverything on the list.
So it was like a trick, but.
of them having to stress out,like have my actual requests
that make me feel comfortableand ready to get on stage and
(08:05):
perform, been, you know,succeeded and been checked off
the list.
They don't have to worry aboutthat anymore.
They just see the brown m andmss and they're like, okay, it,
it has or it hasn't.
That was their kind of.
Crazy version of just beingmentally prepared.
Uh, again, I never asked MickJagger why he wanted his rooms
painted beige, but.
(08:26):
I can kind of take, I, I thinksome of it was OCD, some of it
was just a request that kind ofcarried on.
Um, you know, from the earlybeginnings.
Maybe it started as a joke, I'mnot quite sure, but it was
something that he could feelcomfortable in.
We were, you know, in adifferent room almost every
night in different cities, andthat's a lot of.
(08:48):
Just, you know, strange pla andunknown places.
And for anyone who has traveledit is, it takes a couple of
seconds when you get into yourhotel room, even if you're
traveling for work and you'relike, okay, I'm gonna work now.
But I just need to kind ofsettle in and, you know, kind of
feel up the space a little bit.
And that was something that hecould just, you know, walk into
(09:09):
the room and it felt the sameeverywhere he went, no matter
where it was.
And then he could, you know,prepare and do whatever he
wanted.
He loved running on treadmills,um, wherever he was.
So he could do that, but he justdidn't have to think about it.
And that.
Another real key aspect that Ialways like to talk about is
like, if you're really trying tobuild success in your business
(09:31):
or your role, um, getting rid ofthose habits that you always
have to think about and makingthem just something that you
don't even have to think aboutand you just do, and those
habits that actually drive succesuccess, that's where successful
people actually becomesuccessful and famous and the
rock stars because they don'tthink about those habits.
(09:52):
It's just something that theydo.
emily-sander_1_06-11-2025 (09:53):
Yeah, and I think, I mean, a Chief of
Staff's job is to create thatspace for their principals, and
it is like, you know, we're talkabout decision fatigue, where
it's like, take the unnecessarydecisions off of their plate.
They have to make a few.
High quality decisions each day,like you gotta tee'em up for
that.
And I think these, these kindof.
Extra habits, just like havethat built in for them.
(10:14):
So I love that.
And then just, I was on thephysical side of preparing.
I remember watching this littlelike featurette on Lady Gaga for
her Super Bowl performance,which was amazing by the way.
Like that's one of the bestperformances in recent memory in
my opinion.
But she.
Was talking to her team and shehad to have like the, I think it
was like the gimbal thing thatshe was like flying across the,
(10:37):
across the sky on like set up ina certain way.
And she was like, I just want itthis way.
I know it sounds weird, but I'mlike, you're flying across like
open air and you could die.
So if you want that prepped acertain way, you can.
And then I remember she was infull costume.
She got in her full costume andshe would go on one of those
like, I dunno what they'recalled, but those machines where
you move your arms and legs uplike a pole and you're like,
(10:57):
you're climbing.
And she would sing.
Her song while she was doingthat, and I was like, what in
the world?
So there's like a me, like aphysical aspect of being
prepared too.
tarra_1_06-11-2025_11332 (11:08):
Taylor Swift is known for that.
She would run on her treadmilland do her entire Aris
performance four
emily-sander_1_06-11-202 (11:16):
That's crazy.
tarra_1_06-11-2025_113326 (11:16):
it is while running.
But you can think about thephysical stamina that these
artists.
Need to not only emotionallyhold the crowd, but also
physically run around the stageand sing.
And you know, some of them playguitar or an instrument, like
it's both.
It's physical and mental workthat they are doing up
emily-sander_1_06-11-2025 (11:38):
Yeah, totally.
And Lady Gaga dances too.
So anyway, I just remember thatI was like, yeah, there is so
much prep that goes into that.
And I think, you know, certainlyI.
Different in like businessworld, but you still have to
think about the health and thephysical fitness of your
principal because they might notbe going on tour, but they might
be traveling 250 days outta theyear.
They might be giving largepresentations to the media, to
(12:00):
the public, to their staff.
So I think all of that comesinto play.
Um, all right.
So how did you kind oftransition from roadie
lifestyle, uh, chief of staff tothe rock stars to what you're
doing now?
tarra_1_06-11-2025_113326 (12:13):
Yeah, so it was a big kind of aha
moment I had so.
Even back when I first jumped onthat first tour bus and I
realized that I just wanted tohelp people achieve their own
dreams.
Um, that was always in the backof my head.
And this one rock star, I'm notallowed to name who it was, but
he would always ask me, um, to,he had this crazy request that
(12:38):
every time we traveled and gotto a new hotel room, he wanted
his.
Toothbrush to be taken out ofthe suitcase and to be sanitized
in a hotel dishwasher.
So industrial, sanitized histoothbrush.
emily-sander_1_06-11-2025_ (12:53):
Wow.
tarra_1_06-11-2025_113326 (12:53):
Um, and so I always get asked like,
one, did you do it?
And I was like, yeah, actually Idid do it.
I didn't even think of her notdoing it.
And two, like, why didn't youjust buy a new toothbrush?
And I, I don't know, again,didn't ask, but that was.
One of the requests.
So a lot of times we'd be inhotels that we'd stayed in
before and they would recognizeme coming and they'd be like, oh
(13:16):
yeah, here's this crazy ladywith the toothbrush again.
Um, but sometimes we'd be inhotels that were new or in a new
city that we'd never played in.
And so I had to, you know, a lot
emily-sander_1_06-11-2025 (13:27):
It's.
tarra_1_06-11-2025_113326 (13:27):
I would try to prepare, but a lot
of times it's kind of hard tocall ahead and be like, I'm
putting a toothbrush in adishwasher.
So it was a almost a spur of themoment type thing.
we were in Shanghai and I wastrying to put this toothbrush in
the dishwasher, and I was likein the back with the staff and I
(13:49):
didn't speak their language,they didn't speak English, and I
was just, you know, trying tomake gestures with this
toothbrush to put it in thedishwasher.
And they were looking at me likeI had three heads.
Again, back in the day beforethere was like Google Translator
or anything, um, and I didn'treally have a translator with me
and.
emily-sander_1_06-11-2025_08 (14:08):
If you have a strange lady coming,
bringing a toothbrush in thedishwasher hotel, that's the.
tarra_1_06-11-2025_113326 (14:14):
Yeah, what is happening?
I don't blame them.
and I just remember standingthere with toothbrush in hand
thinking, there's gotta be moreto life than this.
And I realized that I, I reallyloved helping people and I
wanted to help people.
And, you know, tasks, likeputting toothbrushes in
dishwashers, I didn't reallycare about that, but I really
(14:35):
wanted to be able to help.
One more than one crazy rockstarat a time.
And I thought, well, why don't Ijust come off the road and just,
I don't know what I'm gonna do,but you know, there's gotta be a
way for me to just help morethan one person achieve their
goals.
Me running around the worldafter one person isn't, you
(14:56):
know, expanding this process.
So in 2007, I came off the roadwith just this dream.
I had no idea what I was doing.
I had no business background.
I, yeah, no idea.
Um, and my network, of coursewas like a lot of high profile,
high net worth individuals.
I started managing their homesand I started basically doing
(15:17):
what I was doing.
on the road, but just for themlocally in, in Toronto.
Um, and that grew into abusiness after that.
So it, uh, still running a kindof personal concierge, personal
lifestyle management company,um, across Canada and the us.
But as I was doing that, I alsorealized that there was, there
(15:38):
was more people we could help aswell.
Not just running their homes,but running like their calendars
and their.
Full.
I always say like managing themas a person and not necessarily
just personal or just business.
It's like them as a whole.
And I realized that that's whatwe were basically doing, running
their household.
(15:59):
'cause their business wouldalways fall into it as well.
Um, so then moved the businessfor Take it Easy, more into that
Chief of staff, fractional chiefof staff, fractional executive
assistant space.
emily-sander_1_06-11-2025_ (16:10):
Wow.
Okay.
I love your tenacity where it'slike, I have no background in
this, but I'm gonna jump in andfigure it out.
And then you do, that's, that'strademark chief of staff.
Love it.
Um.
So when you talk about like highnet worth individuals and
running their entire household,like all aspects of their life,
I mean, I can imagine what thatwould be like for me, but I
(16:30):
think you're talking about like,I like to buy that island, or I
wanna go like get thatrestaurant or whatever.
Like what types of things doesthat entail?
tarra_1_06-11-2025_113326 (16:39):
we talked about this before and I
have a funny story about onevery high net worth individual,
um, in Toronto, probably one ofthe most famous Canadian
musicians, and there was a.
Store, uh, a restaurant like amom and pop Jamaican Patty
restaurant closing.
It was kind of famous and it wasall over the news that it was
(17:01):
closing.
They were retiring.
Um, and, you know, people ofToronto didn't want this
restaurant to close.
And so this, my client was like,oh, uh, I need you.
He calls me up and he is like,can you just go buy this
restaurant on my Amex?
And I was like.
emily-sander_1_06-11-2025_08 (17:19):
As you do, you know.
tarra_1_06-11-2025_113326 (17:21):
I was like, no, no, I can't.
What goes in his mind is, butthere's an unlimited spend on
it.
And I'm like, yep, nope, that's,that's not the problem.
But you know, of course I willfigure it out and we will buy
this restaurant.
There's just a couple moreprocesses than handing over an
Amex.
Card.
Um, so yeah, so managing theirlives is managing just all those
(17:46):
crazy ideas that come into theirhead.
Um, also their staff.
So they have a lot of, you know,cleaners on staff and people,
gardeners, um, valets drivers,depending on how large their
properties are.
A lot of them have multipleproperties, so when they decide
to, you know, go off to.
(18:08):
Wherever their second or thirdhome is, making sure that it's
stocked, that the staff is readyto go for their arrival, if
they're having guests that youknow, the guests are comfortable
and they're ready.
So just making sure again, thatthey are ready and prepared
physically and mentally as well.
emily-sander_1_06-11-2025_ (18:26):
Wow.
And so like how do you, um, howdo you personally build trust
with these folks?
Or you have, you just alreadyknown them so they trust you.
And then a secondary questionis, I.
Like, how do you build out theirteam, like the, the lawn people
and the cleaners, and I'mimagining personal trainers and
personal chefs and all thesepeople around them.
How do you make them feelcomfortable with, with those
(18:47):
staff members as well?
tarra_1_06-11-2025_113326 (18:48):
so I am a huge believer and you are
only as successful as yournetwork and from back in the day
when I was having to go get allthese crazy requests like.
Oh, I wanna have a party and Iwanna have a live goat in the
hotel room.
For some reason, rock stars likegoats and parties.
I don't know why.
Um, but you know, like it waslike, okay, who can I call?
(19:11):
Who's the, you know, farmer inthis city that I need to call?
Um, so, you know, I would neverbe able to have gotten anywhere
without the connections and therelationships that I built that
I could lean on when I was inthe city, or I could lean on for
their connections.
Obviously, know, you can't just,it can't go one way.
(19:32):
So we would always give themlike free concert tickets or
whatever they want.
Signatures backstage passes,whatever they wanted.
Um, but yeah, so I learned veryearly on that the.
I could only get so far bymyself, and that's what I took
into when I opened my business.
And again, had zero businessbackground at all.
But I, and I was like, I don'tknow how to go out and get a
(19:54):
client.
Maybe I should just call thisperson.
And then I realized, oh, myclients are actually here
through my network anyway.
So I know it's kind of a copout,um, conversation, especially for
people who are like, I don'thave a network yet, which is
totally fair.
Um, but I, I truly believe thatif you want to get to a certain
place in your business or yourcareer, you should start
(20:17):
building your network.
If you don't have it now, youshould start, um, building it to
a point where it is, you canlean on it for whatever you
need.
emily-sander_1_06-11-2025 (20:27):
Yeah.
So, um, can you talk a littlebit more about who take it?
Easy group helps.
So you mentioned high net worthindividuals is, are these like
entertainment folks?
Are these in the sports world?
Any high net worth?
What, what does that look like?
tarra_1_06-11-2025_113326 (20:38):
Yeah, so really any high net worth,
ultra net worth individual whohas multiple businesses.
Um, a lot of people come to usfrom, and I don't just mean
multiple businesses, but I meanlike multiple things on the go.
So businesses, philanthropy, youknow, a family office.
Like just they need that chiefof staff running their entire
(21:00):
life and not just necessarilytheir business or their charity
arm or whatever it is.
Um, so those types of people,and again, just because that's
kind of my network that I havealways been around, we have a
lot of former athletes that cometo us.
I think because they reallyunderstand the power of an
assistant and it's not aconversation of, you know, you
(21:24):
need a conversation, but it'slike how strategic of an
assistant you actually need,which is really interesting to
me.
Um, and they have a lot ofpersonal assistance, but the
personal assistants are amazing.
It's.
It's my background.
I'm not putting down personalassistance at all, but they just
don't necessarily have thatbusiness, um, mindset as well.
So they need someone who canhelp with the business and the
(21:46):
personal assistance are great tohelp with, you know, manage
their lives on that side.
so yeah, a lot of formerathletes and then just a lot of
just high growth founders,people who are building really
cool things.
You don't have to be acelebrity, you don't have to be
ultra high net worth or high networth, but if you have a really,
really cool idea and you havethat passion and drive behind
(22:09):
you, that you understand thatyou need that strategic support,
we're a good partner for you.
emily-sander_1_06-11-2025_ (22:15):
Love it.
Yeah.
And I love the fact that itsounds like when you're
successful, you just have anunderstanding.
You need this strategic supportlike you, like you will not be
able to do what you can dowithout it.
And I think, like I have so manyconversations about like, what
is the chief of staff?
What, why is the chief of staff,do you really need a chief?
I'm like, if you wanna.
(22:37):
Take it to the next level.
If you wanna be top of yourfield, then yes.
If you don't, then like, sure,go ahead and don't have one.
Um, so I love that, like you're,what I'm hearing is these people
just know that and they're justlike, okay, what, who am I gonna
get?
How strategic are they gonna be?
And I'm curious too, if theyalready have like a team of
personal assistance, do you comein and work with that existing
(22:57):
team?
Uh, do you bring in like yourown staff?
How does that typically work?
tarra_1_06-11-2025_113326 (23:01):
It depends.
Um, I am not here to takeanybody out of a job at all.
So, um, absolutely happy to workwith, um, who, whoever their
team is, even if they have chiefof staff.
We've come in and helped people,uh, on a contract basis.
And when the chief of staff, aswe all know,'cause I know you
have mostly chief of stafflistening, we, our jobs, our day
(23:23):
to day are packed.
And then somebody tells us, oh,there's this massive project now
we have to do, or a new launch,or we're opening up in a new
country or a city.
And you're like, how the heck amI gonna get that off my plate or
fit that into my schedule?
Um, so we've come in and helped,uh, on a contract basis just be
(23:43):
that second right hand person,um, to really be able to help
bring those projects to life andget them across the finish line.
emily-sander_1_06-11-2025_0 (23:52):
And if you, if they want someone to
like, design their team ordesign their support system,
I'm, I'm like thinking of anexample, like I have a charity
and I have like a real estatebusiness and I have multiple
homes, like you say, okay, letme get some.
One, to kind of be the managerof the, the, the house, the home
situation, and then let me findsomeone to spearhead the
(24:12):
philanthropy, the charity piece,blah, blah, blah.
And then you kind of orchestratethe whole thing.
Is that how it works or is thatdifferent?
tarra_1_06-11-2025_113326 (24:18):
Yeah, sometimes, again, it depends on
the situation, so sometimes theyjust need, like, they need
multiple people in eachorganization because they have
tons of projects going on.
Sometimes they just need onevery strategic person at the
head of everything.
Who can delegate out to usuallyteams that are already in place,
(24:39):
um, for, you know, philanthropicefforts and a business launch
and whatever that they're doing.
So again, it depends on thesituation, but.
I know we've talked about it andI'm sure you'll have lots of
conversations about thedefinition of a chief of staff
and they, you know, it can beanything these days really.
Um, and for us and what we do,it's a lot of that strategic
(25:03):
project management support andteam alignment with
administrative help as well,just because that's my
background.
Um, but that's kind of how wefall into helping manage all
those different arms.
emily-sander_1_06-11-2025 (25:17):
Yeah.
And are you.
I mean, are you personallybecoming chief of staff to all
these folks and then popping outto another engagement?
Or do you have like a team ofpeople that you place?
How does that work?
tarra_1_06-11-2025_113326 (25:28):
So if I was doing it all, um, I would
not be here.
I'd be dead probably.
There's definitely not enoughhours in the day for that.
Um, yes, I have a team ofwonderful full-time, so they're
full-time with me with Take ItEasy.
Chief of Staff and ExecutiveAssistants.
Um, that we then contract outor, uh, partner out with
(25:52):
multiple clients depending onthe engagement and the level of
engagement.
Uh, so it's our responsibilityat take it easy to find them,
the clients, and it's theirresponsibility to kind of live
up to the, take it easyexpectations of how they, uh,
partner and work with theclients.
emily-sander_1_06-11-2025_ (26:10):
Wow.
Okay.
Okay.
So if someone's listening, whattype of, what type of folks or
background or just like traitsand like character assets would
you need?
I.
tarra_1_06-11-2025_113326 (26:19):
Yes.
So, um, being able to understandthe lifestyles of, uh, you know,
high net worth individuals andultra high net worth individuals
is really important becausethey're, they're.
is just the way they think andoperate is very different than,
say, a founder, um, who has alot of big goals.
(26:40):
So understanding that, um,having experience in the startup
space as well as corporate isreally helpful because it, um.
It just helps you work acrossboth the functions that we
usually get clients in and thestartup space.
I find that you can run a lotfaster and just understand that
(27:02):
chaos is always a thing.
Um, so that's really helpful.
The, we do a lot of testingaround proactive and strategic
thinking, so if you're aproactive strategic thinker, we
would love, actually I'm hiringright now, so if anyone is
listening.
Please, uh, go to my LinkedIn.
We can put a note to the bottomand, uh, send me your resume.
(27:25):
Um, but yeah, proactive thinkersare really important as well.
Um, and yeah, anyone who justlikes to work with a, we're very
collaborative on the Take ItEasy team.
Um, we love to have fun.
We went on our team trip thisyear to Coachella.
Um, very important to have thatmusic background.
Um, so yeah, we, we are like afun collaborative, not very
(27:48):
corporate team, um, but thenbeing able to kind of like put
on that face for the clients aswell.
emily-sander_1_06-11 (27:55):
Beautiful.
And we will have that LinkedInlink in the show notes.
And then is there a website oranything you wanna point people
to to learn more?
tarra_1_06-11-2025_113326 (28:02):
Yeah, take it easy.
group.com is where you can findeverything.
emily-sander_1_06-11 (28:07):
Beautiful.
And what is your new podcastabout?
tarra_1_06-11-2025_113326 (28:09):
Oh, can I swear on this podcast?
emily-sander_1_06-11-2025_ (28:12):
can.
tarra_1_06-11-2025_113326 (28:13):
Okay, so the podcast is called Fuck
the Fluff, and it is um, well alittle backstory again'cause I
like backstories.
Um, but I was getting kind offrustrated with the fluffy
advice that is always kind ofput out on podcasts.
(28:34):
And as you can hear in what I'vebeen trying to talk about and
share stories is I like to giveactual.
Takeaways and as I call themnuggets, um, for people to be
able to go, oh yeah, I'm havingthat problem, or I can see that,
how I can get that out of it.
Whereas a lot of times peopleespecially like, you know,
pretty famous people or peoplewho do those like podcast
(28:56):
circuits, you'll hear, oh yeah,I went from living on the street
to being a billionaire.
And you're like, well, that'sgreat.
Like how did you,
emily-sander_1_06-11-2025 (29:04):
Yeah.
tarra_1_06-11-2025_113326 (29:04):
the steps?
That you actually took and thenyou hear a lot, oh, I manifested
it.
Um, and it's like, no, like youactually had to do something to
get there, or else we'd have alot more billionaire, uh, you
know, entrepreneurs in our, inour world.
Um, so I just really wanted toshare.
I.
The like non fluffy advice ofactually how to build success.
(29:27):
Um, I love talking to femalefounders, female entrepreneurs,
female business owners who havebeen through really shitty times
as we all have in running ourbusinesses, and can share that,
that non fluffy advice on howthey got through to the other
side.
emily-sander_1_06-11-202 (29:46):
That's awesome.
Okay.
We'll have any of thatinformation in the show notes as
well.
But um, Tara, thank you so muchfor being on the show.
Thank you for sharing somereally fun stories and really
appreciate you and what you'redoing
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