This trip involved two business-class bookings on the same routing, booked separately, funded differently, and decided under different information sets. The result was strong. The execution was not perfect. Both deserve to be shown.

Two business-class seats were needed between London and Nairobi, routing via Cairo, on fixed late-summer dates.

Cash prices for the exact flights were high:

Award availability existed via LifeMiles at:

The starting LifeMiles balance was effectively zero. All miles used were generated specifically for these bookings.

The return flight was the most expensive for cash, and award inventory was limited. The outbound had slightly more flexibility. That created real pressure to lock the return first.

At that moment, the decision framework was straightforward: Capital One points versus the cash price of the ticket.

A 15% Capital One → LifeMiles transfer bonus was live in early August 2025. That allowed:

On that basis alone, the redemption cleared comfortably above 4.5¢ per point. That felt decisive. And it was reasonable.

So the return was booked immediately, funded entirely via Capital One points.

Judged in isolation, this is an excellent redemption.

The outbound was more involved.

Award pricing was attractive, but starting from zero meant the full 110,000 LifeMiles had to be sourced. There was no live transfer bonus from Amex or Citi, and most of the Capital One balance had already been used. Attention turned to buying miles.

A LifeMiles buy-miles promotion was running from 25 July to 14 August 2025, offering up to a 160% bonus.

Two purchase paths existed:

The decision was framed marginally, not emotionally: how much additional cash was required to step up, and what quantity of incremental miles that step created.

Stepping up produced:

Using a conservative floor and treating Amex Membership Rewards as worth at least a 1:1 conversion into LifeMiles (a legitimate framing, even though I would not actually make that transfer), the transaction created a minimum of:

That caps the effective acquisition price at ~1.19¢ per mile.

Once that anchor was established, the rest of the outbound decision became straightforward.

With LifeMiles available at ~1.19¢, any 1:1 transfer from Amex or Citi stopped being a redemption decision and became a sale decision.

The real question was:

I’m not.

There are ways to cash out transferable currencies around 1¢ per point, or marginally higher in specific cases. I’ve never been tempted by those options. I value transferable currencies higher than that, both intrinsically and for the optional upside they retain.

In reality, I would be more likely to be a buyer than a seller of Amex or Citi points at 1.19¢.

So locking them into LifeMiles at that price would not have made sense, regardless of how attractive the flight redemption looked. Amex and Citi transfers were ruled out entirely.

With the purchase framework in place:

Using the 1.19¢ acquisition price established above, the mileage component effectively cost:

Add the surcharges, and the implied all-in cost of the outbound business-class flight was approximately $2,085, versus a $3,872 cash fare.

A clear win.

Here’s the part that doesn’t get cleaned up.

The Capital One transfer happened before the LifeMiles purchase opportunity was identified and fully anchored.

At the time of the transfer, Capital One points were being compared directly to the cash ticket price. With a 4.5¢+ redemption value, that felt unquestionably correct. The assumption was fair, but the analysis was incomplete.

Once LifeMiles were shown to be available at ~1.19¢, the correct pricing anchor for any LifeMiles-funded decision changed. A 1.15× Capital One → LifeMiles transfer is economically equivalent to valuing Capital One miles at:

1.19 × 1.15 ≈ 1.37¢ per point

That reframes the earlier decision.

The real question becomes:

I’m not.

That isn’t a catastrophic outcome, but it’s not something I would have done with full information. That’s where the regret comes from.

Had the LifeMiles purchase framework been fully internalised before the Capital One transfer, a cleaner alternative existed for the return leg:

Buy another ~110,000 LifeMiles outright at ~1.19¢ (roughly $1,300), add $165.96 in surcharges, and fly home for about $1,466 all-in instead of a ~$4,566 cash fare — while preserving the entire Capital One balance.

That option existed. It just wasn’t visible yet.

This wasn’t a “look how perfect this is” episode. It was a good outcome with a visible flaw.

What still worked:

What didn’t:

That’s worth leaving in.

Because this is what real points usage looks like in practice: strong decisions made under incomplete frameworks, followed by better frameworks discovered later.

The result was excellent, but the process was imperfect.

That’s the part people usually edit out