To lead is to let go: Why I fired myself as CEO — Tribeless

By letting go of this role, I’ve gained so much in return.

Gwen Yi
10 min readDec 5, 2018

Think about something you know to be irrevocably true:

“A circle is infinite.” “The sky is blue.”

“I am an entrepreneur.”

Now, imagine waking up one day only to realize that it isn’t.

What would you do? How will you come to terms with it?

This is the story of how I’m learning to make peace with who I am — and what that means for my community, my company, and my future.

But first, let’s start at the beginning.

What does it mean to be a leader?

Growing up, I was always the loudest kid in the room.

In a sea of quiet, obedient, filial Asian children, I was that little rebel who just wouldn’t shut up. Screaming, playing, laughing, making a fuss and ordering other kids (and sometimes adults!) about.

As I grew older, the labels started pouring in: “Bossy”. “Pushy”. “Obnoxious”.

The only one that softened the blow was “Leader”.

So, for most of my youth, I thrusted myself into various “leadership” positions — in classrooms, at competitions, and later, in the family.

Yes, that’s how protective I can get of her 😂© Bryan Chong

My parents got a divorce when I was 10.

In the void my father left behind, I stepped up as a parental figure for my baby sister. In my mind, that role left little room for error… or vulnerability.

I grew up pretty quickly after that, but the labels were like splinters, working their way under my skin. I never stopped doubting myself. Second guessing my every move. Making sure everything I did was perfect, so nobody could hold it against me.

What does it mean to be a founder?

Winning my first startup ideation competition to the Nobel Peace Prize Convention in 2013.

When I turned 19, I was exposed to the world of technology startups.

I felt the strangest sense of affinity with startup founders. They were resilient, smart, and kind beyond belief. They took me in as one of their own, seeing my youth as an asset, not a liability. So I wore it like a badge of honor as I hustled my way into conferences, hackathons and startup competitions (all for free), hoping that their magic would rub off on me through sheer proximity.

“Fake it ’til you make it,” they say. But how do you know when you’ve made it?

You don’t. So you just keep on faking it.

Winning MasterCard’s Masters Of Code 2015 in San Francisco, USA.

After about three years of relentless hustling, in which I learned to code, got into an innovative tech-based university, and moved to San Francisco, I had the rug unceremoniously ripped out from under me:

I was living the tech startup dream, and yet, I was severely depressed.

I chalked it up to mean that tech wasn’t the domain for me. So I cut my losses, came home to KL, and marinated in my misery while I figured my life out.

At that point, I was willing to rethink all of my identities — the girl in Minerva, the girl in education technology, the girl in Silicon Valley.

But not once did I question the identity of being a founder.

What does it mean to run a company?

Facilitating a Tribeless Conversation in Yogyakarta, Dec 2017. © Endro Gunawan

Founding Tribeless was a lifeline out of the existential depression I’d felt.

For the first time, I was surrounded with people who shared my deepest belief — that it’s important to create safe spaces for people to listen, share and grow.

It started out as a community. We hosted public conversation events, bringing people from all walks of life together to break bread and share stories. As the community grew, and we gained more experience, we took our insights and created The Empathy Box — cards that facilitate empathic conversation.

When we made the decision to register Tribeless as an official company earlier this year, I thought it would be the same as running a tech startup. Focus on growth, not revenue. Move fast, break things. All that jazz.

Pitching Tribeless at Changemakerxchange PH 2017. © Kathleen Guytingco

So grow, we did. I leveraged the skillsets I’d developed in the past (namely, getting stuff for free), and attended conferences to build partnerships, get case studies, and spark interest. Because we had so little overhead costs, I never felt pressured to start actually generating revenue.

I thought I was doing “market validation”. But really, I was just afraid.

Afraid to charge, afraid to grow, afraid to commit to anything.

I never actually stopped “faking it”. Inside, I was always that insecure 19-year-old, playing at startups; or that frightened 10-year-old, trying to be strong for her little sister.

As the face of Tribeless, it’d become intertwined with my own identity — if it received any criticism, it would feel like a personal attack. I would go to great lengths to manage Tribeless’ image; my first thought before we did anything would always be: “What would other people think of this?”.

That mindset kept me ensnared in a prison of fear. I didn’t dare take risks or make big decisions, for fear of permanently tarnishing Tribeless’, and thus my, reputation. My vision spun like a weathervane; I tried to strategize and make plans, but invariably ended up changing my mind two days later.

I was confused, and lost, and scared… But instead of asking for help, I’d cover it up with a facade of imperious obstinance. I did everything I could to avoid being vulnerable — even to the point of a founder break-up (sorry, Riff).

A weathervane spins to show the direction of the wind

Soon, it was just Shawn and me, partners in work and life, trying to survive.

My antics frustrated Shawn to no end. He’d run businesses before, and had a much better idea how to make this work — but because of our complicated dynamic, he chose to keep the peace and stay silent most of the time.

Until one fateful day in September, when we — I — decided to launch the Box.

What does it mean to launch a product?

The Empathy Box © Tribeless

The decision to sell The Empathy Box came as a shock — to our customers, our community, but most of all, to ourselves.

It all just happened so… impetuously. Spurred into action by a Host’s story, I decided to launch sales for the Box, a decision I’d been delaying for months — in a single afternoon. (You can get the full low-down here.)

I was in fight-or-flight, and for the first time in my life, I chose the former… But I had no idea how to do it right.

And it was a mess — not just because we didn’t sell as many as we hoped we would, but because of everything that came after.

Marketing the product. Designing the manual. Planning, filming and editing two 40-minute Udemy courses in two days. Packing all 200 Boxes by hand. Shipping them out with hand-made boxes and hand-written notes. Not to mention all the admin, legal, finance and logistics that goes into that.

All in a 10-day timeline. Yikes! I feel exhausted just writing about it.

And I didn’t even do most of the heavy lifting.

Shawn cutting hundreds of Empathy Box cards by hand! © Tribeless

While I was freaking the F out, Shawn stayed calm and pulled us through. He systematically worked his way down the list of to-do’s, ensuring we stayed on track and fulfilled all our promises. Thanks to him, we successfully shipped 120 Empathy Boxes to 22 countries — and kept our sanity. 💛

When the campaign came to a close, and I was reflecting on the marathon I’d unwittingly made us run, the reality of our situation dawned on me:

I had no idea how to run our company. But Shawn did.

He’s smart. He’s resourceful. And he’s resilient as hell, willing to deal with all the stress, uncertainty and failure that comes with the job description.

I’m good at a completely different subset of skills — writing, facilitating, building relationships, designing experiences…

All great things. But they had nothing to do with running a company.

Passionately pitching Tribeless at The Collective UK © Miholyn Soon

I’d fallen into the trap of dichotomous thinking — I thought that just because I started Tribeless as a community, that I could run it as a company. That as the founder, I also had to be the CEO. That to have the impact I wanted, I had to eschew traditional 9–5 jobs and run my own company.

Turns out, I could still have my own company; I just didn’t have to be the one running it. But admitting that meant letting go of the identity I’d coveted for the past six years:

I wasn’t some brilliant, business-minded startup CEO, and my baby was actually better off in someone else’s hands.

And I wasn’t sure if I was ready to do that.

What does it mean to let go?

It took me a whole month of processing before I was ready to do it.

I realized that by learning to let go of this role, I was letting go of so much else — the emotional baggage I’d attached to Tribeless, the societal expectations I’d internalized, and most importantly, the idea that I’m some perfect, wise, irreproachable person.

I’m not perfect. But I’m learning that to be a leader, I don’t have to be.

Leadership isn’t about pretending you have it all together, or telling others what to do. It’s about humility, and vulnerability, and trust, and being willing to put yourself last — even if that means (temporarily) removing yourself from the equation.

So, over vanilla lattes and a cathartic cry, I did the impossible:

I let go.

Shawn prepping for a facilitator training at A SPACE TO __ © Tribeless

As of November 1st, 2018, Shawn is the de facto decision-maker and CEO of Tribeless PLT.

And me? I’m more myself than I’ve ever been. 🙃

I write more. I read fiction. I go on adventures in my own city. I make cards on people’s birthdays. I stopped actively using social media.

I’ll continue to be actively involved in the company, but running the business is now Shawn’s responsibility.

I can finally allow myself to just be… me. And I honestly couldn’t be happier.

By speaking openly and truthfully about my journey, I hope to inspire you to be as honest with yourself. Did this strike a chord? Do you have truths that you thought were unquestionably, irrevocably true? It’s worth a ponder.

For me, I am learning to be more honest everyday. To fear judgment less, and to seek beauty more. To exorcize my past, step by step, word by word, so I can one day walk fearlessly into my future.

It is terrifying. But I also can’t remember ever feeling so alive.

Shawn and I on our work trip to Hong Kong, March 2018 © Tribeless

So what’s next for Tribeless?

2018 was a year of incredible growth, change and experimentation, but under Shawn’s leadership, 2019 will be the year of refinement — of daring to double down on our purpose, and saying no to anything that doesn’t align with it.

Our biggest takeaway from the Empathy Box launch is that we need to shift our focus to education — giving folks the skills and knowledge they need to facilitate these empathic conversations, instead of just the tools.

It’s a scary thing to commit to. But we also know it’s an important step to take.

One of our first times working together: TechInAsia’s KL Chapter, May 2017 © Ariff Ariffin Hew

It has taken us so long to get to this point — exactly two years, in fact, since we first met. Every epiphany, every triumph, every blazing argument and crucial conversation has only served to make us stronger, wiser, and infinitely more human. I am so grateful for the people who have stuck it out through it all — our Tribeless Hosts, our Empathy Box buyers, our clients, our attendees, amd our friends and families.

Thank you for never giving up on us. Now, let’s go change the world. 💛

Gwen Yi is the founder and ex-CEO (😉) of Tribeless (, an experiential empathy education company. If this resonated with you, I’d love to hear from you.

Sending you warmth and hugs in advance. x

Author’s Note (23/10/19):

Thank you for your emails, messages and love! There’s some confusion I’d like to clear up — I did not leave Tribeless. I am still very much involved in its day-to-day operations :) Stepping down as CEO was a transfer of decision-making power; it was not a removal of myself from the company. In fact, I probably am more involved now than ever! Please don’t hesitate to reach out to me about anything Tribeless-related.

Author’s Note (1/12/20):

Aaaaahhhhhh I’m so excited to share that I did an interview with Vulcan Post almost two years after I made the decision to step down as CEO, and it brings tears to my eyes to look back on this decision and see how much we’ve grown since then. If you’re interested in watching it, here is the full interview!



Gwen Yi

writer, facilitator, founder | i tell honest stories of my experiences with @tribelessco