Say Yes First, Figure It Out Later (And What I Learned When It Didn't Work Out)

A popular mantra in entrepreneurship is "Say yes first and figure it out later". That was exactly what I did when I pitched my tech consultancy services to a client. What followed was 2 months of anxiety, firefighting, and lots of learning. And PTSD from Meta/WhatsApp. Telegram is goated.

My client runs a transport business serving various retail brands in Singapore. He coordinates transport to ferry 100+ staff between work and their homes every single day. The coordination involved significant manual effort and he wondered if it could be automated. Sounds simple enough.

It wasn't.

The Problem Space

Here's what I walked into: my client served multiple retail stores, each sending him worker schedules in whatever format they preferred. Mostly via WhatsApp. Group chats, one-on-one messages, unstructured text, even photos of schedules on computer screens. He had to manually comb through dozens of chats daily, compile everything into Excel, then organize transport accordingly. Every single day. Monday through Sunday.

The obvious solution? Standardize communication with all clients. That would win 75% of the battle right there. But my client couldn't risk losing customers by forcing them to change their habits. He wanted them comfortable. So my job became: automate the chaos without changing the status quo.

Learning #1: Always Have a Contingency Plan (Especially for Critical Operations)

This was a critical operational need running 24/7. WhatsApp had to be running constantly to collect information. Any integration that touched the WhatsApp number carried risk. And there was no contingency plan if something went wrong.

I hadn't really worked with WhatsApp API before. The anxiety was constant. I could not afford to break their business. There was no room for downtime.

When something inevitably did go wrong, we had no backup plan. It was really bad.

The lesson: when you're touching critical business operations, you need a fallback before you start. Not after things break. Before. Even if the primary solution seems solid, even if you're confident. Especially then.

Learning #2: Some Technical Limitations You Can't Research Your Way Out Of

I tried to use Meta/WhatsApp Coexistence, which would let my client keep his number while using API features. Seemed perfect.

It was extremely buggy.

Sometimes customers wouldn't receive messages we sent. We'd added a whole new layer of technical problems on top of the existing business problems. And here's the thing: you couldn't find information about how buggy Coexistence was online. You only discovered it after onboarding with a Meta business partner and going through multiple customer support chats.

Then came the real killer: WhatsApp APIs don't work on group chats. Only one-on-one. About half of my client's communication happened in group chats. So right there, the value proposition was cut in half.

And because the system was so buggy, images sometimes wouldn't load. My AI couldn't read schedules from images that wouldn't load. Value cut in half again.

I couldn't deliver what I'd promised.

The lesson: I'm not too hard on myself about this one. The Coexistence issue was genuinely something you couldn't understand until you tried it. But it taught me that some technical constraints only reveal themselves in production. You can research all you want. Some things you only learn by doing. And that means you need to price in the risk of discovery.

Learning #3: Some Platforms Are Black Boxes (And That's Scary When It's Someone Else's Business)

Meta is, with good reason, quite a black box. You need to verify your business extensively. Multiple steps to prove you're not a scammer. They can ban your number anytime.

That scared me. Because the most important thing to me was that I could not leave the business in worse shape than before I started working on it.

I explored every possible solution. I even almost onboarded to a Meta business partner, but providing custom webhooks through them would cost so much it would eat up most of my profit margin. The economics didn't work.

The lesson: when you're integrating with platform giants, you're playing in their sandbox with their rules. They can change things, ban you, or just be inexplicably buggy. Factor that platform risk into whether you take the project at all.

Learning #4: Transparency and Effort Build Trust (Even When You Fail)

After realizing it wasn't going to work, I created a comprehensive document for my client explaining what went wrong and what I could have done better. I was ready to refund the entire deposit.

He told me he was actually very happy. I'd gained his trust through the sheer amount of effort and time I'd put into trying to solve his problem. He could see I'd given it everything to make his life better, even though it didn't turn out the way we wanted due to limitations on Meta's end that we genuinely couldn't solve.

He was grateful. He's open to working together again on future problems. He offered to recommend me to others. It was genuine. I could tell he wanted to help me succeed too.

The lesson: do your absolute best for your customers. They can see it. Even when the project fails technically, you can succeed relationally. Build good relationships by showing up fully. Sometimes that matters more than the outcome. And good relationships compound into future opportunities.

So What Does "Say Yes First, Figure It Out Later" Actually Mean?

I still believe in saying yes. But I've learned to say yes with better risk assessment:

• Is this a critical operation? If so, what's the contingency plan?
• Am I integrating with platforms that could be black boxes or have arbitrary restrictions?
• What are the technical limitations I need to verify before promising specific outcomes?
• Can I commit to leaving things no worse than I found them, even if the project fails?

"Figure it out later" doesn't mean "ignore the risks". It means being honest about what you don't know, pricing in the discovery process, and committing to transparency when you hit walls.

The anxiety was real. The PTSD from Meta is real. But the learning was worth it. And my client's trust? That was worth more than the project fee ever could have been.

Next time someone asks me to automate their WhatsApp workflows, though, I'm asking a lot more questions first.

And suggesting Telegram.