Smart About Money: The Art of Making Complicated Decisions Perfectly

The first thing to realize when it comes to making complicated decisions perfectly is that there is no “perfectly.” Complicated decisions usually have at least one significant obstacle and often it’s more like “one thing after another.”

Complicated decisions frequently involve time, money, deadline pressure and emotion – that’s what makes them complicated. Even something that was supposed to be a good step forward or fun can end up being quite frustrating in the process of making it happen.

And complicated decisions often seem unique or “once in a lifetime,” making them difficult to prepare for or learn from.

Your goal? To be ready to keep moving in a positive direction even when you’re starting to wonder if you made a mistake or starting to be sorry you ever went down this road in the first place. It means not getting down on yourself, being willing to pull the plug if necessary and definitely having a Plan B.

There is wisdom in the old folk saying, “If it ain’t broke, don’t fix it.” What that doesn’t take into account, though, is the occasional need to upgrade something that isn’t broken but isn’t up to modern standards either. Upgrading is one way of getting into complicated decision territory where sometimes things just don’t work out.

For example, a colleague and I were talking about a local business that decided to upgrade their internet connections.

They were very clear about wanting several parts of their “legacy” technology to interact with the upgraded connections. The internet service provider assured this company that everything would work fine and they’d save money too.

You can probably see where this is going. Both systems worked but they didn’t work well together. At all. After giving it a fair trial, the company ended up going back to the “legacy” technology that was marginally more costly but completely reliable, which mattered more.

Was this company wrong to try to upgrade? Not at all. They did their due diligence and thought they knew what they were getting into. They were right to give it a shot and smart to be willing to decide that enough was enough when it became clear that the hoped-for result was probably never going to happen.

In other situations, it can take focused patience, time and a bit of luck to get something accomplished.

A customer told me about applying online for what looked like a very good opportunity. “I thought it would take 15 minutes,” he said. “It was presented as being that easy.”

In reality, it took him the better part of 3 weeks working off and on to get together the paperwork he needed and to figure out the online application system (which was not intuitive!).

The worst part of it? “There was no one to talk to,” he told me. “No one to call to see if I was doing it right.”

Finally this gentleman did find a phone number for the company. He spoke to a very helpful tech who walked him through the parts where he was stuck. His application went through and it all worked out just as he’d hoped.

He was lucky to run into that person. Finding someone you trust who you can talk to briefly or work with throughout the process usually makes a huge difference, especially if you feel confident that person is honest to the point of being willing to tell you things you may not want to hear.

Even with that help, often the best way to handle complicated decisions is to decide to pace yourself, take breaks and keep tackling the very next step, trusting things will resolve in a good way. Aiming for progress – not perfection – often gives you the best chance of actually having things work out perfectly.

Nick Maffeo is the President & CEO of Canton Co-operative Bank in Canton. “Smart About Money” is a regular column he writes for the Canton Citizen. Have a financial question you’d like to ask? Email to


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