In my experience so far, this is a lot less true in the startup world. Unless you're growing exponentially and the name of your company has officially become a verb, success is a lot less clear. Some days there's a ton of enthusiasm around your business, then the next day someone is yelling at you asking you "Is this a joke?" (Yes, that happened). And there's nothing you can point to that definitively says, "Screw them, I'm sure I'm doing well." When you are creating something that didn't exist before, you don't know what the milestones are. And you don't know what trajectory you're "supposed" to be on. By definition. This isn't necessarily a bad thing. In fact, it's exactly what I wanted. I wanted to break free from the traditional pre-determined career trajectory. I wanted to make my way into the unknown so I could try to create, build, make something that mattered.
Of course, that all sounds nice, but what does all that actually look like? Sure, you could say that success is earning X in revenue, or having Y number of students, or raising Z in capital ... but money doesn't equate to making a legitimate difference (though I hope they're not mutually exclusive). So then what does equate to doing something legitimate? What am I really trying to achieve? I'm sick of my own romantic notions of "changing the world" or "building something that matters". And even if I did feel comfortable sticking to those as my "goals"... how would I know if I were on track? Does the fact that I don't know mean that I'm not on track? And so it goes...
But I guess maybe the point is that you have to rise above needing those milestones that superficially assure you that you're doing a good job. I have to stop trying to "achieve", and just live in the moment. I need to stop looking outward and just listen to my own barometer of success i.e. am I happy?
Eh... I'm not there yet. It still sounds a bit like bullshit to me. I'm enjoying this adventure, of course, but part of me still wishes I knew exactly what the next step looked like so that I could know where I stand.