Analyzed user's concern about deathbed regrets.
UnderstandExplained local optimization as a short-term strategy.
UnderstandDiscussed limitations of gradient descent for overall life optimization.
PlanThe loop has one saving grace: it doesn't really recur. There's no stable next level — nobody sustains worrying about worrying about worrying about deathbed regrets — so the exit isn't another meta-floor up, it's sideways, out of the frame. And noticing the loop, which you've evidently done, is most of that move.
The sharp part of your observation is that it's empirically on the nose. In the actual deathbed-regret literature (Bronnie Ware's hospice work — methodologically soft, but still), one of the canonical five is "I wish I hadn't worried so much." Worry isn't the prophylactic against the regrets; it's on the list. Regret-minimization run as a continuous background process is just anxiety wearing a philosophy costume.
The frame does have a legitimate use: as a tie-breaker at the handful of genuine forks in a life — take the job, move the country, have the kid. Consulted maybe five times, then closed like a reference book. What's broken is the dashboard mode, and it's broken in a Goodhart way: it spends present attention to manage a hypothetical future feeling, when present attention is the actual substance that feeling will be a verdict on.
Also worth holding: your deathbed self is a stranger. Their values will have drifted somewhere you can't predict, and humans are reliably bad at forecasting their own future feelings anyway — so the anticipated regret you'd be managing is probably miscalibrated to begin with. The defensible move is making decisions your current self endorses with the information you have. A future self can forgive a good process. It's verdict-chasing they'd roll their eyes at.
As the inner loop, yes — it's the right answer to the last turn's problem, since following local gradients on signals you can actually measure (am I learning, do I like my weeks, do I like who I'm becoming) beats backpropagating from a terminal loss you'll evaluate once, sixty years out, with hopeless credit assignment. But as the whole algorithm, no, and the failure modes are exactly the ones from the textbook.
First, you don't have a fixed loss function. The objective is non-stationary and — worse — a function of the trajectory: the person doing the evaluating is reshaped by the steps taken (the deathbed-stranger problem again). You're not descending a landscape so much as co-learning it. Pure gradient descent assumes the one thing life doesn't give you.
Second, local minima, and life's landscape is brutally non-convex. The okay job, the okay relationship, the okay city: gradient ≈ zero everywhere, so you sit there for a decade. Every move that matters — quitting, leaving, starting, the kid — is a deliberate step uphill, a loss spike no gradient-follower would ever take. And note that many basins are adversarially carved: the feed, the fridge, the funnel. Entire industries profit from your convergence.
Third, the measurable gradient is mostly hedonic, which is a Goodhart proxy, and it's noisy as hell — update on every fluctuation and you thrash. So you want momentum (commitments that coast through bad weeks) and an annealing schedule (high temperature in your twenties, cool gradually, never to zero).
Which gives the synthesis: gradient descent within basins, as the daily routine — and occasional basin-hopping between them. And the proposal generator for those rare uphill jumps is precisely where the regret heuristic earns its keep: consulted five times, at the forks, then back on the shelf.