I lost a 12k deal this week

Sunday musings: While I am upset, it has become clear to me about the kind of work I refuse to do.

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Sometimes the lesson arrives dressed as a mistake, and it takes a few quiet days to see what was actually being protected.

This week started with momentum because a potential client moved quickly toward a signed agreement, and after weeks of conversations, revisions, and alignment, a five-figure deal finally felt real in my body and not just on paper.

I let my guard down for a moment, shared a small screenshot of our email exchange before a contract or NDA was in place, and that single action caused the entire deal to collapse.

At first, the only emotion I could feel was self-blame because $12,000 matters when you run a one-person business, and every win carries weight and relief.

I kept asking myself why I would do something so out of character, especially since I usually move slowly, quietly, and with discipline in client work.

As I sat with it longer, another memory surfaced from a previous client who drained my energy through constant micromanagement, contract policing, and decision reversals driven by unofficial advisors who never trusted my expertise.

That experience taught me how expensive the wrong client can be, not in money, but in mental load, resentment, and the slow erosion of confidence.

When I replayed my recent conversations with this new client, the signs were obvious: she openly described herself as difficult, flagged heavy restrictions, adjusted payment structures midstream, and subtly positioned herself to control trust.

My wife even asked me if this client felt similar to the one that nearly broke me before, and I had no honest answer because I already knew.

I ignored my gut because I wanted the deal, and the universe stepped in with a hard stop that felt cruel in the moment but merciful in hindsight. Losing the deal hurt, but staying would have hurt longer.

To ground myself, I ran the transcript of our final call through Claude and asked a simple question about pattern recognition, and the answer came back clear and unemotional. This was the same dynamic repeating itself, just with a different face and a larger number attached.

That moment reframed everything because not every lead is meant to become a client, and not every opportunity is aligned just because it pays well. When someone hires you for done-for-you work but does not trust your judgment, the relationship is already broken before it begins.

Parallel to that loss, I spent this week doing something deeply uncomfortable by stepping into pre-needs planning work and handing out flyers on the ground, facing rejection from strangers in an industry that still relies heavily on outdated outreach.

Giving out four flyers out of a 100 in 90 minutes was humbling, clarifying, and strangely grounding.

It also showed me how much room there is to approach end-of-life planning differently, especially in Singapore, where funerals, niches, and planning costs are high, emotional, and rarely discussed openly. I see space to speak to younger people through story, visibility, and honesty, not fear or pressure.

That is why I started a new content series called “Doing Hard Things” on social media, where I document rejection and real conversations rather than polished sales.

It is also why I am exploring collaborations with financial advisors and creators who already speak to younger audiences, because trust travels faster through shared values than cold outreach ever will.

I did not hit five figures this month, and that stings, but I also did not sign myself into months of stress and emotional fatigue. This work is a marathon, not a sprint, and sometimes staying in the race means letting a deal walk away.

I am ending this week tired, relieved, and clearer than before, and that clarity feels like progress even when the numbers say otherwise.

See you next Sunday.