Expert Advice: What If I Fail Again?

Question

What if I fail again?

Many have asked this question as entrepreneurs or will at some point in their entrepreneurial journey and we felt that Aliaa Remtilla’s personal story will help address the fear and uncertainty that is often associated with this question.

Answer

What if fear isn’t holding you back – but holding the key?

For me, fear begins in my chest as a quiet heat. Then it spreads to my face. My arms. My toes. It’s a full-body alarm that freezes me and forces me to pay attention.

I felt that fear – vividly – two years into building StoryTiling, a startup I co-founded. We had raised significant funding, we had a promising product and we had clients. But we didn’t have a clear path to a big exit, like our investors were hoping for. And one day, my co-founder asked the question that had been left unspoken for months:

“Should we stop?”

Hearing the question spoken out loud hit me hard. My body responded before my mind could: the heat, the tightening, the sense of everything narrowing in. 

It wasn’t just fear about the future of the company. It was fear about what the decision would say about me – a BIPOC woman who had “made it” on paper. Harvard grad. PhD. Non-profit executive. And now co-founder of a venture-backed startup. I had built a life around ambition and success. Around proving that I could succeed in spaces that weren’t built for me. Which meant that the startup HAD to succeed!

I come from a tight-knit, high-achieving community. I’m a second-generation Canadian Ismaili Muslim. My parents (and grandparents and great-grandparents) were born in Tanzania. My ancestry before them is from the pre-partition Indian subcontinent. In communities like mine, reputation matters. Failure isn’t just personal. It reflects on your family. Your upbringing. Your worth.

So my startup HAD to succeed. And that’s the decision we made. We pivoted, retooled and found ourselves with more traction than ever. Our product gained real momentum. Customers were happy. We knew what triggers to pull to increase our revenue. We had what we’d been chasing all along.

I bet you’re rolling your eyes right now…yet another “success story” that rings untrue. 

It’s not that. Because a year later – after three years of building, iterating, and paying ourselves minimum wage – we were tired. We had traction, yes – but we were out of capacity. The product was strong, but our energy wasn’t. We craved financial stability. The life we’d built for ourselves around the startup no longer fit what we wanted our lives to look like. 

We found ourselves asking the same question again:

“Should we stop?”

The fear was just as present as it had been the first time. But I responded to it differently. I didn’t try to stuff it deep down and will it to desperately GO AWAY! Instead, I got curious. I sat with it.

What am I here to protect? What am I pointing to? What am I not yet ready to admit? The questions didn’t banish the fear; they brought it into the room in a new way. And I began to explore what value fear might have to offer. What if it wasn’t an obstacle to overcome, but information to work with? What if fear could serve as a compass – not always to avoid, but to understand?

That shift changed how I moved through uncertainty. I stopped seeing fear as something to eliminate and started seeing it as something to learn from. And when I finally listened, I realized the fear wasn’t just about failing. It was about what failure would say about who I am.

I’d spent my life achieving – recruited to play field hockey at Harvard, got a PhD, led a multi-national nonprofit, published a book – I’d built a story of relentless forward motion. The idea of shifting direction – without a clear “win” – felt like breaking that story. It felt like fear.

Once I understood that, I was able to work with it. And ask the better question: “What do I actually want?”

And the honest answer was the way we were working on our startup wasn’t sustainable. We weren’t ready to shut down the company – our product was positively impacting people’s lives. But we needed to change how we were supporting it. So, we decided to reduce our time inside the business and bring in someone who could help it grow with more capacity than we had.

That decision opened yet another decision to be made: what next? Consulting would have been the obvious next move – predictable income, clear deliverables, short-term contracts. It would have let me recover financially, while still leaving time to contribute to the startup.

And I almost did it.

But there was something else pulling at me. Coaching. A path I’d been circling around for years – but never fully claimed because it was risky. It meant building another business from scratch – and I knew how hard that was. Would I be able to get clients? Would I be able to sell what I do? Did the world really need one more coach?

And more than anything: What if I failed again?

The fear of compounding failure was real. It would make me “that person” whose early promise faded into a string of quiet flops. The woman who peaked early. Who couldn’t keep it up.

And once again, I needed to switch from worrying about what my life looks like from the outside, to asking the deeper question of what was true for me. And I realized that if I didn’t give coaching a real shot, THAT would be the failure. Not trying at all – choosing safety over truth – was the outcome I feared most.

And maybe that’s what fear was trying to show me all along: not what to avoid, but what mattered enough to risk failing at.

And as I grew my coaching business, I saw this same pattern in so many of my clients. High-achieving professionals, many of them women of color, who are smart, capable, driven – and who have gotten very good at managing fear by pushing it down and ignoring it. Many of us learned early on to compartmentalize emotion in order to survive and succeed. We stayed focused. We got through. We achieved.

And then, often in our 30s or 40s or 50s, the armor starts to crack. The strategies that helped us rise begin to feel brittle. That’s where I meet my clients: in the liminal space. That strange, stretched-out middle where one chapter is closing and the next hasn’t fully arrived. It’s uncomfortable. And it’s also where real change begins.

And the work we do sometimes has to begin by stripping everything back to what truly matters, beneath the noise. Other times it starts with envisioning a different future altogether – one that honors not just what my client is good at, but what they actually want.

Together, we stop waiting for fear to disappear, and start asking what it’s here to teach. And it’s different for everyone. Meena went from feeling directionless and powerless to reclaiming her agency and negotiating a higher salary and a promotion. Caroline, drowning in the responsibilities of motherhood and being a startup founder, learned how to say ‘no’ without guilt so she could prioritize herself. And Anisa listened to a nagging feeling that something was “off” and launched a new business and landed her first three paying clients in just two weeks.

None of them waited for fear to disappear. They listened to it. They learned from it.

I still feel fear all the time: when I share something publicly that matters to me (like this article!), when I launch a new offer, when a client hesitates, when something I pour my heart into doesn’t land. But now I don’t freeze. I don’t run or hide. I breathe. I listen. I learn.

The real work isn’t about erasing fear. It’s about building a life that can hold it. And inviting it in. Because fear, when faced with open curiosity, can point us to the exact thing we’re meant to pay attention to.

Fear sucks. And it’s my best friend. Maybe it could be yours too.