Entrepreneur Emil Anton writes on his blog that you can use “simulated outcome theory” to determine if you’re on the right path in life.

Here’s how it works: look at how your life is going right now and imagine doing the same thing for the next 10 years.

If you’re happy with the result then keep at it. 

But what if this imagined future sucks? As Anton puts it, you need to make a drastic change to your timeline. “That’s when you drop out or quit your job in order to start living on your own terms.”

You may end up working longer hours, but at least you’ll have the satisfaction of working on your own terms. For Anton, this is one of several risks you must take. Not taking this risk increases your odds of being miserable and living a mediocre life.

After all: “If you don’t build your own dreams, someone else will hire you to build theirs.”

In his book The 48 Laws of Power, author Robert Greene writes that most people think short-term and are ruled by their heart, not their head. 

They’re often locked in the current moment, their future plans are vague, and when they meet obstacles they improvise. Unfortunately, “improvisation will only bring you as far as the next crisis.”

When you see several moves ahead, you won’t be as tempted by emotion or the desire to improvise: “Your clarity will rid you of the anxiety and vagueness that are the primary reasons why so many fail to conclude their actions successfully.”

In an interview on The Knowledge Project podcast, Greene calls this tendency to be locked in the moment “tactical hell.” 

For example, say your company is in a battle with a rival for market share: “If you keep reacting to what your opponent is giving you in this rivalry to get market share, your mind never rises high enough above the battlefield to come up with a reasonable plan that actually is more strategic, and involves things that aren’t just reactions.”

Planning all the way to end is powerful because it forces you to think longer-term.

Greene acknowledges that regardless of how much you plan, the future remains uncertain. But most people suffer less from over-planning and rigidity than from vagueness and a tendency to improvise constantly in the face of circumstances.

As he puts it, “If you are clear- and far-thinking enough, you will understand that the future is uncertain, and that you must be open to adaptation. Only having a clear objective and a far-reaching plan allows you that freedom.”

Decision making expert Gary Klein writes in the Harvard Business Review that projects can fail because people are reluctant to voice their concerns during the planning phase.

Klein recommends conducting a “premortem” at the beginning of a project to discuss those concerns, and to increase a project’s likelihood of success.

The task is to generate plausible reasons for the failure, and to prevent it from happening.

Klein gives the example of a team at a Fortune 50 company that conducted a premortem on a planned billion-dollar environmental sustainability project. 

The project leader began the premortem with the assumption that the project failed. Everyone in the session then took several minutes to write down every possible cause of the failure.

One executive suggested that the project failed because employees lost interest after the CEO retired. Another attributed the failure to a government agency’s policy change, and the negative impact this had on the business case.

An important benefit of a premortem is that it makes team members more sensitive to early signs of risk or trouble once the project has started. 

As Klein puts it, “a premortem may be the best way to circumvent any need for a painful postmortem.”

“Most people die with their music still inside them.”

- Psychiatrist Gordon Livingston in his book And Never Stop Dancing