06/27/2026
He’d been making music seriously for almost a decade at that point, releasing fairly consistently, building a small but real audience, and yet when I asked where he wanted to be in five years he didn’t have an answer beyond something vague about wanting to be bigger, which when I pushed on it a little turned out to mean almost nothing concrete he could actually work toward.
We spent that whole session just trying to define what bigger meant to him specifically, whether it was income, audience size, touring capacity, critical respect, or some combination he hadn’t separated out before, and what became clear pretty quickly was that he’d never been taught to think about his career in those terms because nobody had ever framed music as something you could actually plan for the same way you’d plan any other kind of long-term work.
Once we had something concrete, a real number for monthly listeners, a real target for sync placements, an actual touring radius he wanted to expand into over time, his day-to-day choices started to look completely different, because suddenly he had a way to measure whether something was moving him forward or just felt productive in the moment.
Most musicians have never been given permission to think about their career with that kind of structure, partly because it can feel unromantic to plan a creative life the way you’d plan anything else, but the artists who actually sustain themselves long term are almost always the ones who eventually did exactly that.
Follow if you’ve never actually written down where you want to be in five years.
