Boring or Fancy

This one keeps following me around: do I take the boring work or the fancy work? However I reframe it, it always lands back on motivation, on why I’m actually saying yes to a given thing right now. Early on, the trade-offs tend to come down to three things:

For a long time I chased them in that order. Challenge first, so I could learn fast. Then control, because I wanted a say in the decisions. Then money, because after enough years you stop pretending it doesn’t matter.

These days I’m less idealistic about it. I don’t need every project to be sexy; I’m happy doing boring work if the team is good and the upside is real, and I’ll still take on chaotic frontier work, I just respect the energy it costs more than I used to. My sweet spot is usually boring work with one genuinely hard edge, enough to keep me growing without the whole thing feeling like a fire.

Right now I’ve got both extremes on my plate. At Motif we’re building the first independent wealth advisor, agentic, working only for you. It’s exciting and technically brutal, with a handful of problems that are basically pure R&D, where you solve one hard thing and two new unknowns turn up in its place. In parallel I have a tech leadership mandate at MCO (My Compliance Office), which by startup stereotype is the “boring” one, except the business performs really well, the people execute, and the economics are healthy.

I don’t have a clean conclusion to hand you.

Fancy work drains you fast: stimulating but fragmented, and hard to stay in flow. Boring work has the opposite danger, the slow slide where you coast, do just enough, and quietly stop pushing.

Right now my answer is to run both lanes on purpose:

Not a tidy answer, but running both lanes on purpose is what keeps me from either burning out or coasting.