Planning Out Your Life May Be Causing You to Fail

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Quick Takes:

  • Planning is essential for the success of your goals
  • However, planning can make you dwell on the past or the future
  • The present moment is where you find your happiness
  • But, if planning is essential, and it takes you out of the present, how can we reconcile and find success?

Planning often results in failure, and not in the way you think. Planning results in failure in that traditional planning devalues the present moment by pulling you into the future or dragging you into the past.

Why does the present moment matter? It sounds like an ephemeral buzzword that business gurus and meditation experts try to pedal, and not something that should go into the planning of your future goals. Well, in a sense, it’s true, “present moment” has become a 21st-century catch phrase. But that doesn’t make it any less important.

Devaluing the present moment devalues your life. Reducing your focus on the “now” reduces your overall happiness and contentment. You might not believe me, but think about it: all the thoughts and ideas that cause negative emotions like stress, anxiety, and fear, are thoughts about your future. All the thoughts and ideas that cause negative emotions like shame, guilt, and anger, are thoughts that dwell on the past.

As Eckhart Tolle reminds us, there are no negative emotions in the present moment. There’s nothing wrong with the now. Everything that can go wrong or has gone wrong occurs in the future or past narrative of your mind. Everything in the present just is, there’s no better way to describe it. The more you keep your mind focused on the now, and the less you let it wander, the happier you’ll be, supported by Dan Gilbert’s study on happiness.

The issue, though, is that when you plan, you naturally pull yourself out of the present and focus intently on the future. Then, when and if you fail at your plan, you judge yourself negatively by the results of your past. This causes a failure of planning where the attainment of your goal is supposed to make you happier, yet the planned pursuit of the goal, in effect, devalues your happiness.

But if you’re like me you know that plans and goals are extremely important. But so too is a love of the present moment. So, how can we plan for the future and remain anchored in the now? Well, by planning, of course!


All goals require a plan. There’s no way around it, and in this stage, it’s ok to dwell on the future and past. You’ll need to in order to understand what your ideal life looks like and the goals required to get there. you see, living in the present doesn’t mean ignoring the past or future. It means using the past and future as tools to enhance the present. So whatever your end-vision is, focus on it firmly, and then work your way back, from that future moment to today.

What quarterly, monthly, weekly, and daily steps are needed to get there? Build out a timeline, both visually and physically, that has all these necessary achievements listed out. Small or large it doesn’t matter; the mini wins will snowball into the bigger ones.

Now that you’ve looked at your plan from end-goal to the present moment, look at it again from today to your end-goal, and then back again. Will your daily effort result in weekly goals, and will those weekly goals result in monthly achievements, and will those monthly milestones result in quarterly wins and eventually your ultimate goal? If so, you have yourself a good plan…on paper.


Once the plan is good enough, it’s time to execute on it. Remember, it’s not going to be a perfect plan, but it’s going to be an actionable one. A good plan executed today is better than a great plan executed tomorrow.

And the beauty is that since you’ve already envisioned what your ideal life looks like and built a set of larger goals around that vision, and then broken your plan down into actionable daily goals, the execution of your plan doesn’t pull you out of the present moment. Rather than worrying about a far off goal, you can focus on the daily effort needed to get there. You can enjoy the moment because you know it’s getting you one step closer to your ideal life.

The downside of lofty aspirations is that your current life never measures up to your future vision. But, if you have a granular plan that takes you from grand life design to daily incremental progress, it helps you keep contentment in the moment while driving hard for the future.


And then, as most plans do, it’ll probably fail. Or, if not, you’ll definitely get knocked off your path, by one life-changing event or another. Lo, what then? Well, since the execution of your plan is needed to test the assumptions you made during your paper planning phase, having to adjust and change course is actually all part of the plan.

All assumptions seem valid when you’re planning in your head, and all life goals seem systematically easy to achieve. Sure, you say, I’ll just do X, then Y will happen, and then I’ll receive Z. Sorry, but probably not going to happen.

Instead, your initial action X will probably throw you for a loop and yield you K, which will shoot you off in the direction of L, and afterwards you’ll have a second to regroup before you react to L and hopefully cause something to happen that will put you back on the trajectory for Z. Confusing, huh?

English alphabet aside, it’s the flexibility of your plan that will help keep you on course when something unexpected happens. And in this way, it’s also not imprudent to use the past and future as tools for the present. Check your course by looking into the future. Check your assumptions by the experiences and data you’ve collected from your past actions. What’s working? What isn’t?

Adjust your plan accordingly. From macro to micro, make sure that each daily step is still pushing you towards your ideal life. Now, timelines and plans always seem to take longer than expected, and don’t perceive a lengthy journey as a reason to quit or fail. But also be honest with yourself. Nothing is worth doing if it isn’t getting you somewhere you want to go, and joy comes from the daily progression towards your goal.


And then? Shut the hell up, sorry. Adjust your plan on the fly, revamp your daily actions if needed, and then re-focus on those daily actions. Be happy, knowing that your day-to-day effort is getting you closer and closer to your ideal life.

And in a sense, isn’t that the ideal life anyway, to pursue something you love?

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