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Sky Jarrett: Change + Transitions

@transcend.tribe

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📍Diaries of a 40+ Woman Starting Over
Change in real time: living it | studying it | helping people + organizations navigate it

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People keep asking me why Costa Rica

And I could give you my five reasons

But the truth is…

This move was never really about Costa Rica

It’s about me finally admitting to myself that I’d outgrown the life I worked so hard to build

It’s about finding the courage to build a life that feels true

And it’s about doing the hard but necessary

Now, changing countries is the easy part. But becoming the woman who knows she deserves this was the real work

If you’ve ever looked around at the life you worked incredibly hard to build…

…and wondered why it no longer fits…

You’re not ungrateful

You’re not crazy

And you’re certainly not alone

I honestly don’t know where this chapter leads

And I don’t believe transformation happens just because your location changes

But I do believe some places create space for parts of you that have been waiting to come alive

And this is where I feel called to be

At least for now…

So maybe you’re standing in the doorway between who you’ve been and who you’re becoming

And maybe this is your wilderness too

If you are, welcome

I have a feeling we’re walking this road together

🤍🤍🤍🤍🤍
Hi, if you’re new here, I’m Sky. A recovering stress addict building a life she loves…one that feels more true, more real, more me…designed for me, by me.

Join me on the journey 🤍 by @transcend.tribe

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3 months ago

For anyone learning to find their footing somewhere between the old shore and the new

Whether you’re changing careers, moving, leaving a relationship, becoming a parent, rebuilding after loss, starting over, or shifting into a new identity…

Here’s to embracing the wobble❤️ by @transcend.tribe

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22 days ago

Life in 2026…

I stopped trying to control everything and life opened up for me in ways I didn’t plan or expect

Mexico. Jamaica. Puerto Rico. Bahamas. Bali…

Places and spaces, people and experiences helping me relearn what it means to be me again by @transcend.tribe

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7 months ago

My control freak is learning that uncertainty doesn’t always need an answer
Sometimes it needs an anchor

I literally don’t know where I’ll be living next month

And the old instinct of my control freak…ehem…recovering control freak, would be to turn that uncertainty into a project:

research harder
plan more
solve it faster
control every variable I can find

But I’m doing things different this time….first of all, I’ve invited my control freak to kindly have a seat…and then…

Anchor. Agency. Trust.

Come back to what is steady
Put your energy where you actually have influence
And surrender what simply isn’t yours to control

I’m reminded that the goal in uncertain seasons isn’t to remove the uncertainty, it’s learning to stay grounded while the answer is still becoming clear

That’s the muscle I’m building right now

And if you’re in your own season of “I have no idea what happens next,” save this for the day your brain starts demanding answers life hasn’t given you yet by @transcend.tribe

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12 days ago

I started this business believing:

➡️Great achievement requires hard work
➡️Building a successful business was going to be hard, and so it would have to feel hard ➡️And I would have to make sacrifices to make it work

Today, we closed one of THE BIGGEST contracts in my career and I’m VERY excited about it

Not just because of the size of the contract but because of what it represents:

🏆Work I love
🏆With people I love
🏆For clients I genuinely love

And I get to support them through one of the most pivotal moments in their organization’s history

But the part I’m really celebrating:

It all happened with ease

I’m learning that meaningful work doesn’t ALWAYS have to come with great sacrifice

🤩The work gets to be fun
🤩The process gets to feel good
🤩And I get to do it with ease AMEN🙏🏽

Will there be challenges? Absolutely
Will it always be easy? No

But let’s be clear…easy and ease are not the same thing and today’s win proves that we get to do the work with ease

I can do hard things without making everything hard
Hustle is a state of mind I no longer subscribe to

PERIODT💃🏽 by @transcend.tribe

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17 days ago

Is it just me, or were you also taught to think of prosperity as more?

More money
More achievement.
More opportunity
More evidence that we’re “doing well”

Well that’s how I’ve always thought of prosperity…

Until I stood in a yard in Costa Rica surrounded by coconut trees, plantains, sugarcane, guava, fruit I couldn’t even name…

and thought

“Wait. This is wealth too.”

Not instead of money

And don’t get me wrong, I’m not suggesting we trade in our ambition

But abundance is starting to mean something so much bigger to me now

It’s the luxury of time

The luxury of health and mobility. Because these knees, honey. THESE KNEES. 😂 And don’t get me started on the back !

It’s having people you love nearby

Food growing in your yard

Enough space in your life to actually enjoy the life you worked so hard to create

And so maybe prosperity isn’t just about having more

Maybe it’s needing less in order to feel like you have enough

I think we’ve been measuring prosperity wrong and I’m learning to measure it differently these days ❤️ taken in Somewhere in Costa Rica by @transcend.tribe

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2 months ago

With all my love ❤️ by @transcend.tribe

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3 months ago

I’m stepping away from social media for the next two weeks, maybe more

This is gonna be long cause I have a lot to say about this! Here goes…

Life has been GOOD lately

Really good

But am I spending more time documenting life than actually living it? 🤔

There’s ton of research on the benefits of a Digital Detox (more below)

But on a personal note, my nomadic sabbatical is about to ramp ALL THE WAY UP

And before I step into what’s next, I want to be really present with what’s ending

Because this journey isn’t just about travel

It’s really about an identity shift

It’s a chance to reintroduce myself to myself

❔Who am I outside of the high-performing CEO I’ve taken so much pride in becoming?

❔Who am I outside of being in a relationship?

❔Who am I when I’m not taking care of everybody else?

❔Who are we when we’re not distracted by our phones?

I don’t know but we’re about to find out!

If you’re in the messy middle of a transition, here’s something I’m learning

Before rushing into the next chapter, spend some time honoring the version of you you’re getting ready to let go of

Not everything needs to be solved immediately

Some things just need to be witnessed

Here’s the scoop on my DIGITAL DETOX:

My average daily screen time is 8 hours and 54 minutes😳

Almost nine hours a day 🙈

That’s a lot of life happening through a screen

For someone whose work centers around helping ambitious people become more intentional with their energy, attention, and nervous systems, it feels important to practice what I teach

Studies show:
🏆 Increased joy
🏆 Increased quality of life experiences
🏆 Improved connection
🏆 Improved mental health (2 weeks of a digital detox has improved symptoms of depressions MORE than antidepressants)

If you’ve been feeling the pull to unplug too, Justin Michael Williams is leading a collective digital detox challenge. Check out his page if you’d like to join us.

When I come back, I have a feeling I’ll return with less noise, more clarity, and a deeper relationship with the woman I’m becoming

See you on the other side.
❤️
Sky

#WomanUnderConstruction
#D by @transcend.tribe

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4 months ago

Do you get suspicious when things are finally going well?

Like you’re waiting for the other shoe to drop?

Looking for what’s wrong, for what you might be missing, just bracing for impact?

Preparing for a problem that hasn’t arrived yet but you just know is coming?

Recently, I had two separate coaching conversations with two different CEO’s

Different clients
Different industries
Different lives

And yet both of them said almost the exact same thing:

“This is going so well that it feels like something’s wrong.”

“What am I missing?”

It struck me because I’ve asked myself the same damn question

Why is it so hard for us to trust things when they’re working out for us?

Brené Brown writes that joy is one of the most vulnerable emotions we experience

Not grief
Not fear

Joy… go figure 😏

Because the moment we allow ourselves to fully feel it, we become aware of how much we could lose

So instead of enjoying the moment, we start scanning for threats

For a long time, I thought that was wisdom

Careful vigilance. And to be fair, that vigilance serves us well

It helps us get through hard seasons
It helps us overcome challenges
It helps us carry the weight of the unknown

But I’m also learning that just because that voice helped us get here doesn’t mean it should have the final word

Because sometimes life just gets to be good

Sometimes the prayer gets answered
Sometimes the relationship is healthy
Sometimes the business idea actually works
Sometimes the hard work actually pays off with ease

And if we’re not careful, hypervigilance can rob us of the very thing we’ve been working so hard to create

Stay aware. Be discerning.

But don’t let fear be the loudest voice in that head of yours

Say it with me:

I’m allowed to trust this season
I’m allowed to relax into grace
I’m allowed for things to just work out for me

Love you, Diaries of a Woman Under Construction™ by @transcend.tribe

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4 months ago

Some seasons require new versions of us.

And I’m learning how to outgrow the version of me that was super dope…but also built out of survival.

The version of me that built a 7-figure business from scratch but was so addicted to stress,
I worked during every vacation
and called it the Relaxed Hustle.

The version who worked 7 days a week.

Who spent Friday nights “in workflow”
hustling late into the night.

Whose worth was defined by being needed.

Whose nervous system only recognized pressure as productivity.

I love her but it’s also time for her to go…
I’m learning to outgrow her with compassion

She got me here, but she cannot lead me
into the life I want now

Here’s what I’m learning… the hardest part of reinvention is not becoming someone new…

it’s grieving the version of you
that carried you this far. The version of you you’ve come to know and trust

Sometimes new beginnings require necessary endings.

Diaries of a Woman
under construction by @transcend.tribe

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5 months ago

Being single in your 40s, navigating grief, and rethinking what womanhood means to you is a strange little cocktail, isn’t it? by @transcend.tribe

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5 months ago

Dear nervous system…

Pressure is no longer the only fuel we perform under.

Joy.
Music.
Aliveness.

That’s the new flex.

Same ambition…
different vibe.
——-
Drop a song that instantly shifts your mood 👇🏽
I’m building a new “Work Vibes” playlist 🎶 by @transcend.tribe

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5 months ago