Live-blogging the beta launch of, Day 2. “Planning, in abstract”

[Welcome back to the live-blog. You can find the previous entry here.] 

I’d like to share my detailed plan for the beta launch. But I can’t, because I don’t one. For the most part that’s intentional – I rarely make detailed plans. I always have clear high-level goals, and I do keep a very long to-do list (using Asana). But I’ve found that anything more exhaustive has normally been a waste.

In this post, I’m going to tell you why. And then in tomorrow’s post I’m going to actually work out a detailed plan. These aren’t normal times, after all. I hope you like whiplash.

I’ve always had an erratic relationship with planning. Some of that probably comes from my parents. My mother is a consummate planner – when she travels, she books the tickets five months in advance. My father would probably just buy plane tickets at the airport if that still worked[1]. Growing up, we would pile the family into the car and he’d drive us over the Rocky Mountains toward some vague destination. When he got tired of driving, we’d bounce from motel to motel until he found a vacancy.

When starting a company, it’s very easy to fall into either of those two extremes of planning. I’ve certainly done plenty of both, and neither really works.

Take, for example, the traditional business plan. A while back, I grudgingly wrote a complete one at the request of a potential investor. It took at least two full days of work, and it was full of specific milestones and spending projections and target completion dates. But as Helmuth von Moltke accurately warned, “No battle plan ever survives contact with the enemy.” It only took about a month of actual building before my priorities had shifted enough to make the targets obsolete.

The less predictable the situation is, the more my father’s method appeals. He doesn’t need to predict how tired he’ll be after driving to Steamboat Springs, or how long my sister will tolerate Dinosaur National Monument. He can just show up and leave when we’re ready.

With LinerNotes, a huge part of the challenge has been just mapping the specific shape of the problem and iteratively sifting practical solutions out of a bunch of crazy ideas. Rigorous planning is expensive, and it’s a poor eureka moment that can be planned in advance. If I stay loose and flexible, I can just build one feature at a time, test how users react, and use that data to figure out what to build next. But being reactive also has dangers – last minute travel can be extortionately expensive, and there’s always the risk that the motels in town are 100% sold out (which happened to us more than once.) I decided just a couple of weeks ago to try to go to SXSW and the logistics of finding lodgings in Austin are giving me flashbacks.

I’m still working on finding the right balance. Tomorrow I’ll walk you through my current process. 

[1] I actually did that once, because there was a problem with the space shuttle. True story.

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