A Thinking Labber wrote:

“Contrary to your advice to have one emotionally-challenging initiative, I have 4-5 major challenging initiatives at work and 3-4 in my personal life, none of which I feel I can realistically defer without significant consequences.”

This is an objective problem. It is quite common. He is likely overwhelmed. If so, my advice to him will involve his understanding his emotions. It all sounds rather warm and fluffy.

How do you apply such advice when you are in such a difficult state? You don’t have enough time or crow space to address the issues you already know about, much less squeeze in time for a warm and fluffy introspection tactic.

Distinguish challenging projects from emotionally-challenging projects

First, let me clarify. When I recommend that you have only one emotionally-challenging initiative, I don’t mean just one challenging project per se. I have at least five challenging projects underway.

But at any given time, just one is my top priority for emotional development.

For that one project, I am all-in emotionally to solve problems that have stumped me so far. This could be a specific project. For example, this spring I am all-in to complete an editable draft of a book, something that has eluded me to date. Alternately, I may be all-in emotionally to make some major personal shift. For example, last fall I was all-in to make writing an entirely value-oriented experience.

Being all-in emotionally means that I am committed to work through all of the old baggage that is going to be triggered when I have difficulties and setbacks. The project has high enough priority that I will build in overhead time to introspect thorny emotional issues. This is what I mean by an initiative.

This is what you can’t do for more than one project at a time. If you attempt it, you fail on everything because you bog down, introspecting so many emotional issues that you can’t get your head together to work on the projects.

Making one project an initiative doesn’t require that you drop all of your other challenging projects. You just need to make sure that they will be manageable. You need to ensure that they can be worked on in parallel without raising such emotionally-challenging issues that you can’t handle them with everything else going on.

Proactively reduce other projects to the essentials

What do you do to make the other projects manageable? The same thing you need to do in the first place if you are tackling many challenging projects at once: essentialize like a maniac so you can divide your time among them appropriately.

By essentialize, I mean ruthlessly separate the most valuable, most relevant, most important aspects of the project from its lesser parts. A commonsense way to do this is to apply the 80:20 Rule.

You probably have done this kind of essentialization when you were operating under severe deadline pressure. You literally could not think about everything, so you stripped down each item on your agenda until you could handle everything that was left.

If you’re going to juggle eight challenging projects, you need to do this proactively, on every project, once a day. You need to put on your creative thinking cap to figure out what is the best use of your time today on each project. Then you need to prioritize your limited time — picking winners and losers for today.

When you bite the bullet to do this thinking up front, you reduce your stress. You see clearly what you can do given your current limitations and commitments. You deal with the issues in advance so they don’t interrupt your attempt to actually do work.

But the process is not fun. That’s why most people do it only under intense deadline pressure.

Expect it to be like a polar bear plunge

To pare down several important projects to their essentials, you’ll need to face your present limitations of time, energy, money, intelligence, skill, etc. Not fun.

You’ll need to drop or defer your favorite bells and whistles. Not fun.

On at least some of the projects, you’ll need to reduce your expectations for the present. Not fun.

Moreover, as you see the objective difficulty of doing all that you are committed to do, self-criticism will pop into your mind. It will trigger frustration, guilt, and self-doubt. The antithesis of fun.

This is the emotional equivalent of a polar bear plunge.

For those who are unfamiliar with the term, a polar bear plunge is a full-body immersion in a lake or ocean during the winter. Some people do it for a good cause such as Camp Sunshine. Some people do it regularly. They will tell you it’s refreshing…after they are warm and dry.

A polar bear plunge is a shock to the body. Your doctor may recommend against it.

But for those committed to their gargantuan workloads, I recommend the emotional version of this plunge every day.

So make it short and have a warm, fluffy towel at hand

If you have eight challenging projects going, you need to take stock and prioritize every day. That’s because the situation will change a little every day. A task will turn out to be harder than predicted. You’ll get new information. New opportunities will arise. If you don’t factor this information into your plans proactively, you will make those challenging projects harder.

But you will need to streamline the process. In fact, I recommend you use the 80:20 rule in your daily prioritization. Allot only 15 minutes for it. Read through and/or update a one-page list of projects and tasks. Face the cold shock of conflicts between your priorities. Accept any uncertainty you have about how to proceed. Use that self-awareness to decide what’s going to get your time today.

Then give yourself a quick shot of self-empathy to settle your emotions and reinforce your rational conclusion. Use the OFNR Quick Reference sheet (free as part of Thinking Directions Starter Kit) to help you do this quickly.

Think of this as drying off with a warm, fluffy towel. You need to get your mind back to operation after the cold shock. You need to remind yourself you are a good person, committed to acting on your rational judgment, including the judgment that you don’t have a lot of time for prioritizing and introspecting. You need to see the top value you are after today.

This is not an optional step. If you just look at your list and see the conflicts without dealing with the emotions they generate, you risk one of two defaults. Some people habitually clamp down on the feelings, raise the pressure level, and try to proceed with tunnel vision. This prevents them from using their full intelligence and creativity and makes it much more likely they’ll do something really stupid. Other people will wallow in the conflict and be thrown off for the rest of the day.

You need to introspect the emotions that are triggered in order to clarify your top priorities and to come up with a creative approach for tackling your self-imposed challenges in a timely way. The self-awareness of your emotions — the introspection — is critical to this step.

When people first hear about the introspective tactics I teach, they sometimes think they are warm and fluffy. No, it’s the clarity that you get on the other side that is warm and fluffy.

When you are stretched thin, choosing to raise the conflicts and introspect your feelings is coldly strategic. It’s a test. If you can’t get your mind into gear quickly, you know you need a second plunge into conflict in order to cut back on your priorities. You prove you can handle the situation emotionally by not shying away from the feelings caused by that plunge.

When you literally jump into cold water, it is obvious what you need coming out. Something warm and fluffy to wrap around your shivering body. When you jump into the emotional deep end, you do not know in advance what exactly you need. You know you need certainty to act, but what’s the conclusion you can be certain about? You need to introspect to figure that out.

That’s why no matter how busy you are, you need pro-active self-awareness every day. If you’ve got so many challenging projects you don’t see how to find the time, I recommend you take a defined plunge into and out of intense conflict over your priorities in 15 minutes a day. Your success on your challenging projects is what’s at stake.