by David Jester

“Without a plan, you’re planning to fail.” – Collective Wisdom

That’s what they used to say in many of the schools that I taught in during my teaching career. In one school, this idea was taken to the extreme. As teachers, we were required to put our daily objectives, not only on our whiteboards, but outside the front door of our classroom. This was so that when people from the district office stopped by to check our progress, it would be clear what we were trying to achieve for that day and where our current lessons fit into the larger plan. 

To that end, the district gave me a binder on my first day (I started after the previous teacher jumped ship in September!) that had every single day for the year mapped out. It included activities for each day, the amount of time each one should take, exact words to say in transition from one activity to the next—all to ensure our students would succeed, period. This was the district’s solution to shrinking the achievement gap between students in our school, and those across town. 

The school’s motto was “Making Dreams a Reality…” and the dedicated teachers of that community were committed to that goal, come hell or high water. We got there early. We stayed late. We had fun, but we worked very hard. The vast majority of our students came from highly impoverished homes. Their families were doing all they could to get their children into the building. Once they were there, it was up to us. And those detailed plans, though I would abhor such a mandate later in my teaching career, gave me a path to follow for which I will be forever grateful. 

Once I got the hang of it, I could deviate from the script; laugh and joke with the kids more. But, the symphony was still there in the background supporting any solo I ventured. If improvisation led me astray, I could count on the plan to bring me back to earth. 

I find myself now in quite a different world. When I think of our clients, the stakes aren’t as high. They have been fortunate. Many have had long careers enabling them to save to ensure their well-being continues into retirement. In truth, saving will do most of the heavy lifting when it comes to preparing financially for retirement. That said, the wisdom holds. 

Our planning process has more to do with the middle school’s motto—the one about dreams. When we build a financial plan for someone, it is a dynamic exercise that serves as a guide throughout the lifetimes of our clients. It provides guide rails to keep them on track and provides probabilities of outcomes that ground their vision in something more concrete. Going in with their eyes open to the possibilities allows them to focus on what’s possible—and perhaps expand their original vision to include more than they had imagined. Much of what we do is to help people blend the statistical probabilities with the concrete realities of their financial lives –allowing them, in many cases, to make their dreams a reality. 

As a reminder, spend wisely & invest in good. Until next time, 
David Jester, CSRIC is a financial advisor with the Jester Group at Baird. He can be reached for questions or comments at
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