You've got to know when to hold 'em

There are several decisions that are challenging me to decide when its the right time to lay my cards on the table. Because everything I'm doing now is unchartered territory for me, I'm much more reticent than I usually am about showing my cards too early. One of the big decisions is how much money and effort I want to put into preparing for my key customer segment's annual conference. Since I started two weeks ago, I've actually closed more projects than I had originally projected (good news). But they are all with one client (mediocre news). I'm a firm believer in spreading my eggs around multiple baskets, so the conference would be a great opportunity to connect with other prospective clients. It would also push me to finish several demos and other little marketing plans I have in order to showcase them to the widest possible number of prospects. And where my ego kicks in, I really just want to be there showing cool stuff and squelching any possible questions of what happened to me.

BUT, my number one priority is doing a fantastic job with the projects that we have on deck. And we'd probably make a lot more progress talking to my old contacts in one-on-one conversations where I can really highlight our demos and capabilities. Plus, the cost of going to the conference is probably more than I want to spend right now, and there's no sense of doing it half way--only one chance to make a first impression.

So I'm torn: relax a little and focus on the hand I have, or go all in for the big debut. I guess I'm on my own on this one, because as Kenny tells us, the Gambler, he broke even. I'm not looking to break even. I'm looking to win.