I hit that point a couple years back, and I had a clearance sale. It doesn't happen overnight, believe me. Selling gear takes time and effort, you can apply the brakes at any time.
I put all five basses up for sale, kept the last one standing. Packing and shipping a bass with insurance is going to run $75 a pop. All of mine were sold here on TB and shipped. My basement looked like a pack and ship store for six months.
Amps were also shipped. Cabinets, I held for pickup. Shipping cabs costs stupid amounts of money.
Pedals, rack gear, basses, amps, cabs, straps, strings, I sold everything until I had one bass, my fEarfuls, a Genz Streamliner, an Acoustic Image ten2, and my looper. I kept the Zoom B3, which is my main practice tool with headphones.
It took over six months. I cleared $10k. It was a lot of work, but I felt great about the whole thing. About ten years worth of stuff went over the side.
Why? Things change, and I had way too much stuff, and I was moving on. Kid leaving for college, tired of the local scene, working more...and I wanted to fund other interests. The urge to simplify.
I don't miss any of it. If something interesting comes up, I still have gear to cover it.
It was interesting to observe how much apprehension the idea of selling out caused, but how freeing the process became. Once I was rolling with a few pedals and the first bass gone, I loved it.
Fwiw, I thought the six string would be the last to go. It was the first.
Since then, I've bought two pedals, and returned one. Gas has disappeared.