What’s So Hard About Managing Time?

Image of a man holding a clock in his hand

It's simple. "I need to manage my time" is a euphemism for "I am choosing not to spend time on important stuff." Sometimes the "important stuff" is work. Sometimes it's rest or recreation or relationships. But if you're dissatisfied with how you spend your time, your choices are not matching your own assessment of what's best for you.

Everybody is confronted with that disconnect from time to time. It's normal to realize that you need to change your schedule or your routines, because your priorities have shifted.

The challenge is to manage your time with as much foresight as is practical. That way, when 20:20 hindsight hits, you see it as something to learn from, rather than a moment for self-recrimination. To have foresight, you need to:

  1. Know your long-term and short-term priorities
  2. Notice "choice points" — the opportunity or the need to change what you're doing to better achieve your goals
  3. Predict the consequences of each choice, of each action you might take
  4. Judge which action to take based on consequences
  5. Act on your judgment

That may sound like an overwhelming amount of thinking to do. If you try to do it all at once, you'd bog you down. Fortunately, there is great advice out there to help simplify this thinking.

Time management experts can help

Time management experts give you:

  • Steps to figure out your priorities
  • Systems to help you keep track of priorities
  • Structures that help you notice choice points and predict the consequences of your choices

When you have a good time-management system, well-adapted to your situation, you have a structure that makes routine choices easy and productive. With the right system, the amount of day-to-day thinking you need to do is quite small.

For specific advice, see my five-star recommendations in time management or the many tips I have written on applying thinking tactics to time management.

Implementing the advice can be a challenge

Despite the great advice, a lot of people have trouble following through. It's common for people to begin a new system enthusiastically, then drop it. It's hard to change habits. And it's discouraging to fall back into the old pattern.

What most people don't realize is that implementing a time-management system takes on-the-spot, targeted thinking. It's not enough to know about time management. There are two thinking challenges you face when you implement a time system.

Challenge #1: Changing how you spend time brings up conflict

Guaranteed, when you try to change the way you spend your time, you will experience conflicts. Internal conflicts are your own uncertainty about which way is better for you.

Early on, you are probably genuinely uncertain about your own priorities. Later, even when you have a system that makes 95% of your choices easy and routine, life will throw you curve balls.

There will be choices that you don't know how to deal with offhand. Maybe it's a semi-urgent interruption. Maybe it's a surprise opportunity. Maybe you're running out of steam and are not sure what to do. If it's not obvious how to choose, you will be thrown into conflict.

When you are in conflict you will need, not just time-management tools, but thinking tools, that can help you address the conflict quickly and move forward.

You need tools, because conflict is inherently unpleasant. You feel overloaded and uncertain and sometimes fearful of making a bad choice. If you stay in conflict, you will feel increasingly uncomfortable and drained of energy. That's why people avoid conflict.

But avoiding conflict doesn't solve the problem, it delays it or exacerbates it. What you need at that moment is to figure out a good choice, quickly. You don't need some theoretical ideal choice — you need to make a timely, good choice that you are confident will move you toward your goals.

This is exactly what my thinking tactics help you do; 3-5 minutes of targeted thinking can help you resolve the conflict or figure out a good next step.

Making difficult choices during the day is the number one application of my general thinking tactics, because everyone, every day, has to face a bit of conflict. Even if you already know how to tackle those conflicts on your own, my tactics will help you address them faster, with less hair pulling.

Challenge #2: Adapting general ideas to your specific situation takes fresh thinking

No matter what any expert says, there is no one-size-fits-all time management system. Any system needs to be adapted to fit with your schedule, your constraints, your preferences, and your work style.

Perhaps you have tried out a tool, and it didn't work immediately. I say, don't give up on it. If you were convinced that you needed the tool, that it would help you manage time better, then it's worth thinking about how to adapt it to succeed for you.

For example, David Allen recommends keeping one long (100+ item) to-do list. I tried that out, and I was completely overwhelmed and discouraged using it. But I agreed with the goal: to have everything you are committed to do written down in a trusted system. So I worked out my own set of specialized lists, which are highly prioritized and have no more than 20 items on them. To figure out what I needed, I had to:

  • Introspect the frustration to discover exactly why the system wasn't working
  • Invent other approaches and experiment with them
  • Monitor the results and commit to a solution

In other words, I engaged in an intense problem-solving process, where the problem was internal (my own frustration). This kind of reflective thinking incurs a heavy cognitive load. Thinking tactics can make the difference between whether you figure out how to adapt the tool, or never figure it out.

Similarly, when you implement a new routine in one area, it can break routines elsewhere. It takes fresh thinking to figure out how to make the tools work in your situation. Here is a case study in how a change broke a routine, and needed to be adapted to my situation.

These are solvable problems. The thing is — you are the only person who can solve them. They are your unique problems. When the system out of the book isn't working, you are the only person who knows enough about your goals, your constraints, and your preferences to identify a creative variation that will meet all your needs.

That again, is where my thinking tactics come in. You only need to do this intense problem-solving once per problem. But you do need to do it in a timely way! My tactics help you sit down, concentrate, and think it through, despite confusion and conflict. The tactics help you draw on that rich source of information stored in your subconscious databanks, which is the information you need to find the best solution for you.

Tips Applying Thinking Skills to Time Management

Tactics can help you act on your priorities now, stay focused on your priorities across time, and figure out how to make that easier in the future.

Tips that help you act now on your priorities

Tips that help you stay on track

Tips that help you do better in the future

Book Recommendations on Time Management

The following three books get my 5-star recommendation. I only give 5-star recommendations to books that I find so true, clear, and helpful that I have literally gone back and re-read them.

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