The Problem with the Middle
One year ago, I was talking with clients about their estate planning. They were way overdue to get their documents updated—about 20 years overdue! Like many people, they had good intentions. They stated this was a priority. They were motived to get it done. And they committed to having everything complete by the end of 2025.
Last spring, they met with their new attorney. They had the initial conversations. Their homework was to think about beneficiaries, guardians for the kids, and final wishes. The tough stuff. But they were prepared and we had talked through most of these choices before they met with their lawyer, so they felt ready.
And then… life happened. The summer got busy. Summer turned into fall. The holidays arrived. Their urgency simply faded.
Now it’s February and they have an anniversary trip to Italy coming up in one month. Suddenly, their estate plan feels urgent again. Understandably, they’re scrambling to get everything in order before they leave the country. I can hear the panic in their voices as we talk through the details again.
This is a perfect example of what I call the problem with the middle.
Think about how we tackle big goals. At the beginning, motivation is high. We feel proactive just getting started. As the self-imposed deadline approaches, urgency kicks in because the deadline is staring us in the face.
But what happens in the middle? Between goal setting and goal completion? The middle is where things quietly drift.
Sometimes when we set a goal with a long time horizon, there’s simply too much time in front of us to feel any sense of urgency. No immediate consequence. No pressure to keep moving. So even important goals — especially emotional ones — get pushed aside.
The same pattern shows up in health goals. Think about someone who wants to “get in shape” for a big event like a wedding. Early on, motivation is high. But without structure in the middle — small milestones, realistic habits — progress slows. Then as the big day approaches, panic sets in. Cue the crash diet, the extreme routine, the unsustainable sprint. The couple may look picture-perfect in their wedding photos, but those last-minute diet tactics don’t last. And every time they see their wedding photos, there’s a quiet reminder that the last-minute scramble wasn’t sustainable. It just leads to future disapointment.
The issue in both of these cases isn’t effort or intention. It’s time. Specifically, too much unstructured time in the middle, that time between setting a goal and ultimately achieving that goal.
One of the most effective ways to avoid the problem with the middle is to intentionally shorten the middle by creating smaller, nearer-term milestones. Not to add stress — but to maintain momentum.
A few ways to do this:
Break big goals into smaller, specific steps with specific dates attached.
Set pre-imposed deadlines well before the real ones.
Decide what weekly progress should look like.
Focus on consistency over intensity.
Acknowledge and celebrate small wins along the way. Do not underestimate this step!
When you create intentional structure in the middle, there’s less drifting and less panic. Just steady movement forward.
Coming back to my estate planning clients: imagine if the goal hadn’t been “get it done by Q4,” but instead a series of shorter commitments — book that first meeting by March, have decisions made by June, get the first draft done by August, and have final documents signed and executed by October. No scramble. No stress. Just steady forward motion. And completion— as planned.
The beginning of a goal feels exciting. The end gets our attention. But real success lives in how we manage the potential problem in the middle.
This Week’s Cool Ideas & Resources
Increase Your Chances of Following Through
This is a meaningful book for anyone who starts strong but struggles with the middle. In John Acuff’s book Finish: Give Yourself the Gift of Done, he focuses on why perfectionism and unrealistic expectations derail progress — and how small, consistent actions are what actually get goals across the finish line. It’s practical, encouraging, and very relatable. Great for work goals, health goals, and life goals (like estate planning!)
Divide By Ten
I wrote this blog years ago and just brought it back for 2026. I teach the Divide By Ten lesson to clients and friends—and I follow it myself every year. Instead of setting goals for 2026 and dividing them up by 12 months, divide by 10 months. Create some urgency. This is a great way to tighten up the middle. Here’s how and why: Divide By Ten
The Ultimate in Mapping Out Your Year
For someone who wants to map out all of 2026 now, and be proactive about everything you’re trying to accomplish in the next 11 months, you may want to invest in The Big A$$ Calendar. I bought mine in Q4 and had a great time mapping out all my personal and professional priorities for the year. I love the giant year-at-a-glance visual and the motivation it gives me to stick to my plans.
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