The swamp is vast, dark, and deep, and passage will cost you dearly. Small bands of travelers with even the most rudimentary instincts for survival will do anything to avoid entry. They recognize it for what it is, redefine their destinations under the shadow of this impenetrable barrier, and either simplify their goals, or turn away toward other ends. Armies with endless resources, supply trains and corps of engineers, can choose to drain the swamp, fly over, or grade and build six lane highways straight through to the other side.

The swamp could be PCI compliance, implementation of a bespoke custom database, or state-by-state navigation of a set of complex regulations. It could be rewriting a major piece of software from scratch, or building something because commercial or OSS versions only had 90% of what you needed.

Small companies don’t have the resources to tackle these kinds of problems, and will either avoid them or get sucked in and die. Big companies can spend the people or money to “just make them happen” – succeed or fail, the expenditure doesn’t pose an existential threat. The danger is when you’re in the middle – big enough to feel that you should be able to hack and slash your way through, but not so big that resources can be assigned without impacting other key initiatives. This is the point at which wishful thinking takes over, and otherwise sane leaders decide that it can be done on the cheap, or alongside other non-negotiably important priorities. This is how teams and companies get lost, stuck in an unending struggle toward an increasingly distant goal – too far in to give up, too far away to succeed.

The corollary to all this is that there’s a lot of money to be made in building a toll road through the swamp – for example, there’s no need for most of us to worry about handling credit cards anymore, because Stripe, Dwolla, Square, Braintree, Paypal, etc. have already solved the online payment problem. You could try to do it on your own, but what looks like a fairly straightforward engineering problem quickly unfolds into a fractal nightmare of regulations, secure code stores, limited access, regular audits, special servers, and so on. Trying to solve this can be a hugely expensive distraction unless you’re huge, or providing the service is your main product. Otherwise, it’s almost always in your best interest to pay the tolls, or avoid the swamp completely.

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