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As an avid scuba diver, there is no shortage of places I want to visit on my bucket list.

And when you spend time talking with other divers, you often keep hearing of the same amazing places.

There was one place that I repeatedly heard people absolutely rave about that quickly rose to the top of my list—The Maldives. When people talked about this place, they seemed to enter a trance-like state!

One day, I mentioned to a friend, “I’d love to go to the Maldives someday.”

His response was simple. In fact, it was only one word—“When?”

There were a lot of reasons I had delayed planning this trip in my head. I had heard it was expensive. I didn’t know the language. It was a really long trip just to get there. Was it even safe to travel there?

But his ridiculously simple question propelled my mind onto a completely different trajectory. Suddenly I had left the world of someday and entered into exploration and planning. That day I was no longer day dreaming, I was now in motion.

When would I go?

I began researching online. I bought a travel guide that I read. We set a budget to start saving for the trip. We started looking at their seasonal weather and diving conditions.

A few months later we booked our dive boat, then our flights. And a year later, we spent 10 days on a live-aboard dive boat with 16 people, diving a different island every day.

It is difficult to describe how incredible it was. We dove with enormous whale sharks and manta rays, and barbecued fresh fish by candlelight on a deserted island about the size of a soccer field.

Once we made the commitment to go—many of our other decisions began to pass through the filter of making this trip happen. We began to arrange our calendar and our bank account around it.

That’s what happens when we assign a timeline to something. Once something becomes a real priority, other things suddenly find their ranking in the order of true importance.

I learned an important life lesson that day—A dream needs to have a deadline or it’s just a pipe-dream—just wishful thinking.

The most dangerous words for your dreams

Some of the most dangerous words we can use are someday, soon, or later, because they set our goals at some elusive place in the future that doesn’t exist.

Peter Bregman is a master coach and writer for Harvard Business Review and has some great advice on this topic, “Decide when and where you will do something, and the likelihood that you will follow through increases dramatically.”

And if you’re like me, your to-do list is almost always too long.

Even if you accomplish ten things, you can’t help but feel frustrated by the things you did not get done. This kills the psychological momentum you get from small wins.

And if you read my post on Margin last week, you know that I believe people chronically underestimate the time it takes to do almost anything. We are perpetually overbooked and over-committed.

Most people I know suffer from CTDD—Chronic Time Distortion Disorder.

This is why it is so important to harness the real power of your calendar.

It’s no surprise that out of hundreds of time-management tools, putting something in your calendar with the time you will do it is the single most powerful thing you can do to increase your odds that it will get done.

Time-management guru Stephen Covey repeatedly said, “If something is going to get done, it must occupy a physical space in your calendar.”

As soon as we begin putting things into our calendar, it instantly becomes clear how unrealistic we are with our time. We clearly see that everything won’t fit, and we are forced to choose what is most important.

Great executive coaches are trained to ask at the end of every session with a client who sets an action step—“When will you do it?”

This deceptively simple step gets people into a routine of always assigning a time to their action.

If you lead a team, the simple act of assigning a date to a project is a critical step. It seems so basic, but many leaders skip over it simply hoping that their subordinates will know to do it relatively soon, leaving both the boss and team member frustrated by unclear deadlines and expectations.

Research also suggests that having your team member help choose the deadline will increase their motivation to ensure it gets done by the assigned time.

I love this quote by Emerson…

“Once you make a decision, the universe conspires to make it happen.” –Ralph Waldo Emerson

His words are part magic, part logic. Once we really commit to actually doing something and set a timeline, it can seem like things just start falling into place and we suddenly begin to see more clearly the steps we need to take to get there. Things we could not see before we fully committed.

Turn information into action

Information is useless without acting on it. Here are some ways you can put this into practice right away:

  1. If you have really big goals, take some time to write in a journal and begin to explore a potential timeline for it. You don’t have to commit to anything at this stage, just allow your mind to consider what it would take to get you there and what you may have to sacrifice to do it.
  2. Admit that you can’t fit everything in that you are currently trying to do.
  3. Take the time necessary every single week or day to identify 1-2 of your highest impact activities or projects. Your brain will resist this, but it will pay off big time.
  4. Put those things in a physical space in your daily or weekly calendar. Do this with rigor and discipline.
  5. Learn to let go of the other 25 things on your to-do list. If they are important enough, they will eventually demand your attention, but often we will have a lot of things on our list that we could simply not ever do. Executing on your most important actions becomes much easier when we release the dead weight of low-value activities.

Suggested Resources

  1. Timeboxing HBR
  2. A Better Way to Manage Your To Do List—Peter Bregman


Dr. Parker Houston

Parker Houston

Dr. Parker Houston is a licensed clinical psychologist and board-certified in organizational psychology. He is also certified in personal and executive coaching. Parker's personal mission is to share science-based principles of psychology and timeless spiritual practices, to help people improve the way they lead themselves, their families, and their organizations. *Opinions expressed are the author's own.
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