He surrounded himself with the thing he’d decided not to become.
At 32, a man looked at what building a company actually required — the years of uncertainty, the capital, the chances of failure — and decided the numbers didn’t work. He became a venture capitalist instead. He would be at the table. He would back the people doing what he didn’t. At first it was close enough: the work was real, the proximity was real, and he was genuinely good at it.
Ten years in, the gap has become legible in a specific way. The founders he backs move him in a way the partnership meetings don’t. Their decisions — even the bad ones — produce something in him that reviewing term sheets never does. He believes he made the right choice. He has just started to feel that he is watching through glass.
What he’s feeling is not regret about the path he chose. It is the original want still transmitting.
How the substitution works
A proxy is a want-adjacent target: something that activates the same motivational channel as the authentic want while substituting a more available or more affordable object. The proximity is what makes it work initially — the VC gets the founding decisions, the product discussions, the thing happening up close. The channel fires. The satisfaction is real.
But the original want has a specific target that the proxy doesn’t fully match. The want-to-build and the want-to-back-building activate overlapping but not identical systems, and the original signal continues transmitting at low amplitude. While the proxy is novel, its novelty masks the residual signal. As novelty fades, the gap between what the man is doing and what he wanted to do becomes perceptible — not as a thought but as a felt texture. The watching-through-glass.
The characteristic response is escalation. The VC takes more board seats, seeks founder experience more directly within the VC frame, becomes more prominent. The audiophile who traded building music for consuming it upgrades the equipment again. The escalation looks like deepening commitment, but it is the system trying to close a gap that additional volume of the proxy cannot close. The gap isn’t between “enough” and “more” of the proxy — it’s between the proxy and the thing.
What makes it hard to revise
The substitution was initially reasonable. The man genuinely couldn’t afford to start a company at 32, or genuinely wasn’t suited to it, or found that VC work was something he could be excellent at. None of this was wrong. The problem is that the proxy worked, which is precisely what makes it hard to revise: the proxy has become the organizing structure of his professional identity, his relationships, his expertise, his reputation. The substitution is now load-bearing.
The Gollum effect is a different failure mode: the substitute morphs the original want into something possessive and dark. The proxy failure is quieter. The original want stays clear — that is the problem. It continues to be recognizable as what it is, which is why the gap remains legible even after years of competent proxy work. The man who developed the Gollum attachment to the ring has lost the original want. The man watching through glass hasn’t. He just can’t get to it from here.
The surplus enjoyment sticks to what was foreclosed, not what was substituted. The proxy becomes more obligatory as it becomes less alive, because the life is now organized around it, which is the mechanism by which a reasonable choice at 32 becomes a structural constraint at 42. The token replaced the thing at the moment the substitution was made — and the system runs on the token, efficiently, while the thing it was representing keeps making a claim the token cannot answer.
The proxy becomes a prison precisely because it was good enough to delay the reckoning. A cheap substitute is obviously wrong; a good proxy is wrong in a way that takes years to see clearly. The tell is not whether you’re skilled at the proxy but whether the underlying thing — the music, the building, the founding — still moves you when you encounter it directly, without the proxy role in between. If it does, the proxy is still carrying the original want’s load. The glass is still there.
Threads to Pull
- James Hollis, Finding Meaning in the Second Half of Life — the midlife crisis is often the proxy becoming visible: the life that was a reasonable substitution for a more risky authentic one starts refusing to hold the weight it was assigned. Hollis on the “unlived life” making its claim is the clinical version of the watching-through-glass.
- D.W. Winnicott on transitional objects — the transitional object bridges the self to the world; a proxy is a transitional object that never got released. The thing it was bridging toward is still on the other side.
- carrying-costs — the proxy and the carrying cost are usually the same situation from different angles. The proxy is the substitute that’s been organized around; the carrying cost is what that substitution charges. Together they explain why the reasonable choice at one age feels like a structural trap at another.
- Vocational counseling literature on “golden handcuffs” — high compensation in the proxy role is the mechanism that converts a reasonable early substitution into a structural constraint; the financial cost of leaving grows as the gap between proxy and authentic want grows. The handcuffs are the compounded carrying cost made concrete.