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Pare down and think in terms of EV

Sebastian,

I read your post "The Million Dollar Question". It was very good. Thank you for sharing it. I can see myself in the friends you mentioned. I have these dreams of ways to increase my income. I have an internet side business that makes about $1500 a month. I know that there are many different ways I can scale it. In my mind I see the way, the things I need to do. But then I sit down to do those things and I freeze. I believe I am frozen by fear. I fear that if I do these things and they don't succeed, I have wasted my time. Or, I sit down and think of all the things I need to do to get to the endpoint and I think "that is a whole lot of work". So I don't do anything. I waste an hour reading HN and playing solitaire. It is really stupid.

Anyway, your post really made me think about it. I think I will write a plan of all the things I need to do to scale in one direction. Then I will break down the plan in small enough steps that can be accomplished in an hour or two. I'll write each step on a Post-It note. When I finish the step, I'll put it on the wall so I (and my wife) can see the progress. What do you think?

I think it's a good idea, and I empathize with where you're at. A few thoughts -

First, I think it can be helpful to start thinking in terms of expected value (EV) - I learned it from playing poker. If you play poker, you're often in a position where you make money on average by doing a good play, but you'll still lose a lot of the time. For instance, if you have an 80% chance of winning a hand and you get a big bet at you - of course you call. But 20% of the time you'll lose. Which sucks, but you've got to just shrug and not get upset because you did the right thing.

Going Crazy In Multiple Projects? Fences. Build Fences.

If you work on multiple, unrelated projects, one of the biggest potential nightmares you'll see as you scale up is work flowing over into other work, blending together, getting mixed up, and otherwise ruining your ability to think without being stressed out. 

The answer? Build fences.

Clearly separate out different types of work.

Obviously, separating out completely different categories and unrelated projects makes sense, and is even necessary as volume increases. I used to have one email address that all my mail went through. It was easy for a while, but eventually work that was imminently crucially important got mixed in with casual whenever emails, got mixed in with bills to pay, and all sorts of things. I broke things into three discrete inboxes, and that helps. If you have too much email volume on things of varying importance, multiple email addresses by topic -- kept separate -- could be an answer.

Then, letting deals blend together is no good. I just recently created a "Deals" folder on my desktop, with subfolders with everything I'm working on. It's a godsend. All my files are in the right places. I used to do this much more ad hoc, and this is so much better. Actually, I created folders for every major campaign I have... and so far, I haven't had a single thing that doesn't belong in one of them.

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