The Tyranny (And Freedom) of Deadlines

Welcome to 2024, a new year offering fresh possibilities along with a new set of deadlines.

Income tax returns are at the top of my list, followed by letters to investors, final approval of yearly budgets, and cash planning for large expenses to come.

As many of you already know from prior blogs, I’m a procrastinator. I often wait until a deadline approaches to take any action. And then I plan backwards (perhaps like many of you). To successfully plan backwards I use the following steps:

1. I identify the goal and the deadline. (For example, filing an income tax return on March 15.)
2. I calculate the length of time I will need to complete the goal (prepare the tax return).
3. I figure out what specific information I need to complete the task. (Financial data in this case.)
4. I determine where to find that information.
5. I begin to accumulate and organize the data, allowing enough time to meet my deadline.
6. I verify the data to make sure it is accurate. (For example, on spreadsheets, I make sure the totals are added accurately.)
7. Once I have collected and organized all of the data, it is easy to aggregate all of the information into the final task (i.e. completing the tax return.)
8. I then perform one final overall check to be sure the results are reasonable. (For example, if I were planning to drive from my office to Santa Barbara, a distance of 76 miles, I would not expect the segments of my journey to add up to 95 miles unless I took several detours.)

So, working backward, if it will take me one week to gather all the necessary data and then prepare the return, I had better plan to start at least a week in advance.  Years ago, I completed the preparation of my income tax return at 9:00 pm on the day it was due.  I then drove to the local post office where dozens of IRS agents were standing on the street to accept the returns from hundreds of “just in time” drivers like me.

But the very best feature of any deadline is the freedom to relax once I have met it. I hope my checklist makes it easier for you to do that.

Until next (week, month, year).

Alan