Stymied from within (an entrepreneurial experience)

In his interview of Andrew Warner, Jason Cohen provided a nice snapshot of the experience of being a software entrepreneur (taken from the transcription provided on the interview page, emphasis mine):

You hear all these stories of success, and luck also always plays a part. We didn’t talk about that much, but of course it’s true. And great networking helps. If you’re ideas really good, maybe the customers will come easy. Again, you hear all these stories on Mixergy. When people condense the timeline, it’s almost inevitable that it sounds easy and straightforward. And one leads to two and that sort of thing.

But then as a listener, you come back to your own reality where it’s hard. You don’t have a network like Jason Baptiste has. You don’t have an article on Mashable. You don’t have a strong sense of your own philosophy and what you think is true in the world and who you want to be. You don’t know yet, because you haven’t gone and done a whole bunch of things and seen how you feel about it. And there isn’t a big rush of customers at your door.

You’re sitting there in front of the computer, with your inbox and a compiler and an A/B tester. You’re overwhelmed by all this stuff. How do you know – obviously, this is too abstract a question to have a specific answer – but how do I take that next step and go running? How do I just go running? Do I just have to say, “Look, there’s nothing but going and running.” That’s it? It’s as simple as that? It’s hard, but that’s all there is?

…where “running” is being used as a metaphor for getting the job done and achieving what you want to achieve.  What really resonated with me was this perspective of being one guy (or maybe just a couple guys/gals) who is at point A, wants to get to point B, and fundamentally must find his own path when none is visible.

As a solo entrepreneur / business owner, I feel like I face an uncertain, massive void every day, through which I must find my way, avoiding all sorts of pitfalls.  Sometimes, that void is the outer world, filled with challenges of all sorts related to technology, business, customers, and money.  However, that void is usually myself, where far more difficult riddles await: What do I want to achieve? What should I focus on now in order to be successful? How can I break out of unproductive habits and cycles? What do I not know today that would save my ass tomorrow?

Some days are easier than others, with answers coming easily.  It’s especially pleasant to have a run of time where one is simply doing, knocking down technology and business problems like so many piñatas. Other days, it’s impossible to make such obvious progress when it’s not clear what should be done in the first place.  And then there are the really bad days, when overwork or self-doubt breeds loss of focus, procrastination, and prodigious mental bonking: a particularly painful state where the flesh is willing, but the mind is weak.

For weeks now, I’ve been tangling with this dim state of being — probably the longest and deepest period of time I’ve ever spent coping with an inability to focus and execute.  As painful as it’s been, I take some small bit of solace that every other entrepreneur, engineer, artist, and writer seems to have been afflicted with similar problems from time to time. Unfortunately, each time this happens to me, I seem to forget for a time that the best salve is almost always the same: keep trying to build, write, create—and eventually the blocks and cobwebs and limits I place on myself fall away.  One really does just need to “go running”.

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