Leading with Empathy isn’t Soft. It’s Strategic, Necessary, and Often Exhausting

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I can tell you right now – I’m f*cked.
Too tired to talk to friends.
Too tired to check in on family.
Too tired to even play with my dogs.

Today has been a blur of spreadsheets, last-minute donation emails, and conversations with team members. A day spent listening, supporting, fixing, holding. All of it done with as much compassion, and as big a smile,  as my current capacity allows.

And here’s the truth most leaders don’t say out loud:

Leading with empathy doesn’t mean being endlessly calm, infinitely patient, or having all the answers.
It means caring enough to keep showing up even when your internal battery is flashing red.

At Pineapple, we’ve built everything on the belief that people need to feel seen, heard, and held in order to thrive. And if we’re going to practice what we preach as an organisation (though clearly not as individuals today), that applies just as much to our team as it does to the community we serve.

Every email deserves a little care.
Every meeting deserves presence.
Every person deserves to feel safe being honest, even on the messy days, the tired days, the “barely functioning” days.

Because empathy in leadership isn’t a softness; it’s a strategy.
A sustainable one.

When we lead with empathy, we build resilience, in ourselves, our teams, and our companies. It’s not about wellness perks or feel-good slogans. It’s about creating cultures where compassion drives performance, and care is woven into the foundation of how things get done.

That’s what keeps people connected.
That’s what builds strong teams.
That’s what turns organisations into communities.

And honestly?
That’s what makes Pineapple what it is.

Even on days like today, when my tank is empty and my brain feels like soup, I can feel the strength of the culture we’ve built holding everything steady. Empathy doesn’t just support people, it sustains the mission.

And tomorrow, when I’m a little less tired, I’ll get back to practising it with myself too.

with love,

Leya

AdultTime Renews Sponsorship of Pineapple Support at the Silver Level

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Pineapple Support, the adult industry’s leading mental health nonprofit, is pleased to announce that AdultTimehas renewed its support as a silver-level sponsor. The premium streaming platform joins over seventy adult businesses and organizations in committing funds and resources to the organization.

 

“We are proud to continue our support and commitment to Pineapple Support and the important services they provide to our production community,” says Bree Mills, Adult Time’s Chief Creative Officer.

 

Pineapple Support was founded by Leya Tanit in 2018, after a string of losses in the adult industry from depression and other mental illnesses. The organization, a qualified 501(c)(3) tax-exempt organization in the United States, has connected over 16,000 adult performers to mental health services, including free and low-cost therapy, counseling, and emotional support.

 

“We are grateful to AdultTime for continuing to support our mission,” says Tanit. “Long-term, dedicated sponsors allow us to do the long-term planning and resource development necessary for building an organization the community can depend on. AdultTime’s ongoing commitment reflects a deep understanding of the importance of performer wellbeing.”

 

To learn more about becoming a sponsor of Pineapple Support, please visit https://pineapplesupport.org/sponsorship. Details about additional ways to support, as a company or individual, can be found on the organization’s website https://pineapplesupport.org/.

Why We All Feel Like Imposters (But Rarely Say It Out Loud)

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There’s a phrase most of us carry quietly, tucked somewhere between our ambition and our exhaustion:

“I feel like a fraud.”

Imposter syndrome, or Imposter Phenomenon, is defined as:

A persistent doubt concerning one’s abilities or accomplishments, accompanied by the fear of being exposed as a fraud, despite evidence of ongoing success.

Sound familiar?

That voice — sometimes a whisper, sometimes a roar — that says:
“You’re not good enough… who do you think you are?”

Even after nearly eight years of building something no one had done before, a global nonprofit supporting mental health in one of the most stigmatized industries, I still hear it. I hear it on stages I’ve been flown across the world to speak on. In rooms full of peers discussing topics I’ve lived, researched, and shaped. Even after creating resources that didn’t exist until Pineapple Support built them, and fighting for change when it felt impossible.

And still, that voice creeps in:

“People don’t think you’re capable. Maybe they’re right.”

Brené Brown puts it perfectly:

“Shame is the most powerful, master emotion. It’s the fear that we’re not good enough.”

Imposter syndrome is shame in motion, a tangled knot of fear and self-doubt that tightens in the spaces where we stretch, grow, and lead.

The most ridiculous part? Almost everyone is quietly carrying it, convinced they’re the only one who feels this way.

So why do we feel like imposters?

Psychologists Pauline Clance and Suzanne Imes, who first identified imposter syndrome in the 1970s, found that high-achieving people often attribute their success to luck, timing, or external factors, anything but their own abilities. Up to 70% of people will experience these feelings at some point.

Here’s why:

1. Our brains are wired for comparison.
Evolution taught us to constantly assess our place in the group. Social media has turned that into a never-ending highlight reel.

2. New territory triggers doubt.
When we’re learning something new, even if we’re good at it, discomfort gets misinterpreted as incompetence.

3. We internalize early messages.
If we grew up believing we had to be perfect to be worthy, adulthood becomes a minefield of “don’t mess this up.”

4. Success feels unfamiliar.
Dr. Valerie Young explains that if you’ve spent most of your life feeling “not that person,” succeeding can feel like a clerical error, not a win.

5. We glorify overworking.
We equate value with exhaustion. If we slow down, the fear creeps in:
“If I stop, they’ll see I’m not good enough.”

And yet, none of these beliefs reflect the truth of who we are or what we’ve achieved.

So what is success, really?

We measure it by titles, hours worked, milestones hit.
Rarely by impact, fulfillment, or balance.

Imposter syndrome convinces us we must outrun our insecurity, work harder, push further, prove ourselves endlessly, just to earn space we’ve already earned.

But as Stef Sword-Williams writes in Fck Being Humble*:

“We spend so much time second-guessing ourselves that we forget other people are probably doing the same. We’re all winging it; some of us are just louder about it.”

And she’s right.

I am still winging it.
We all are.

Whether you’re an innovator, disruptor, thought leader, or simply someone trying to change your corner of the world, most of the journey is figuring it out as you go.

So why don’t we talk about it?

Because imposter syndrome thrives in silence.
We bottle it up, smile through it, and pray no one notices.

But what if we told the truth?

What if we normalized saying:

“I’ve achieved incredible things… and sometimes I still feel like I have no idea what I’m doing.”

Imagine the shift, the collective exhale,  if more of us said it out loud.
Because not feeling “enough” isn’t a sign we’re failing.
It’s a sign we’re human.

So here’s my rebellion against imposter syndrome:

I’m choosing to acknowledge it.
To speak it.
To own it.

To remind myself, and you, that we belong in the rooms we’ve worked so hard to enter, even when our inner critic tries to convince us otherwise.

Because at the end of the day, we’re all just people trying our best.
And that is more than enough.

with love,

Leya

I thought I had to be perfect to lead

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For most of my career, I carried an unspoken rule:
Leaders have to have it all together.

No cracks.
No doubts.
No messy human moments.

Just competence, confidence, and a perfectly polished exterior.

There are quite a number of leaders I know who project exactly that, the kind of poised, untouchable professionalism that looks effortless. One day, when I grow up, maybe I’ll be just like them.

But today?
I’m choosing to embrace the version of myself I’ve always been:
a little quirky, a little sideways, a little messy, and completely real.

Like many founders (and as I’ve spoken about openly before), I am no stranger to imposter syndrome. I can walk into a room full of brilliant minds, CEOs, therapists, compliance directors, creators, and still feel like the teenager who never quite fit in. Add to that the reality of being a high-masking autistic woman running a mental-health charity in an industry the world doesn’t always treat kindly… and, well, you can imagine the pressure I put on myself.

To those who lead from the front and make it look easy:
I salute you. Truly.

But perfection isn’t the sign of great leadership.
Humanity is.

Everyone is learning.
Everyone is trying.
Everyone is human.

This is something I spoke about recently during a Wellbeing by PS training:
If you want a healthy team, you can’t just tell them it’s okay to ask for help.
you have to show them.

People don’t learn from policies.
They learn from permission.
And they learn permission by witnessing vulnerability.

When I stopped trying to tuck away the “odd” parts of myself, the quirks, the humour, the autistic wiring that makes my brain work at slightly unexpected angles, something surprising happened:

I started forming stronger connections.

At shows, in boardrooms, at conferences (9am with terrible coffee or 9pm with terrible wine), the more I allowed the real me to show up, the more others showed up as themselves too.

Conversations became more honest.
Collaborations became smoother.
Relationships became deeper.

And, to my knowledge, no one has run away yet.

Of course, professionalism still matters.
Boundaries matter.
Consistency matters.

But I’ve learned that professionalism doesn’t require dimming your light, even when that light is quirky, chaotic, or unmistakably “Leya.”

When you let people see who you really are, they respond with who they are.
And strangely enough, that makes everything, leadership, teamwork, community, so much stronger.

Because most people aren’t looking for a flawless leader.

They’re looking for a human one.

with love,

Leya