The Aspiration-Driven Life: Part 6 — Overcoming Obstacles9 min read

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Whatever the goal you are pursuing, in any area of your life, one thing is certain: you will be tested. You will meet obstacles at every step of the way. If you have the right tools and mindset you’ll be able to overcome them and fulfill your aspiration; if not, you will eventually give up.

By finding and embracing your aspirations, developing the key practices of awareness, and taking consistent action, you have already created a buffer against most challenges. Yet some of them will still come, unavoidably.

In this article of the series, I’ll give you an overview of the main obstacles to living the aspiration-driven life, and how to overcome each of them. This is an elaborate map of dozens of concepts and techniques in the Mindful Self-Discipline framework.

Please remember: you don’t need to learn them all. Instead, focus only on the ones related to your biggest obstacles in this phase of your life.

Low Motivation

Motivation is a feeling. It is the desire or fuel to take action. When your motivation is high, everything else feels easier—it’s like the wind is on your back! When your motivation is low, everything feels like a drag, and you need to exert extra willpower just to keep on track.

There are two strategies to overcome this obstacle. The first one is to cultivate motivation regularly. You do so by:

  • making sure you have the right goals to begin with
  • reflecting on how important your goals are for you
  • hanging out with people who are passionate about the same things
  • consuming inspirational material
  • cultivating self-belief or self-confidence
  • removing friction from your path

You can also go through chapters 6 to 9 of Mindful Self-Discipline, along with the Black and White exercise in the free workbook, to help you cultivate motivation.

The second strategy is to rely on commitment. This will shield you from the oscillations of motivation, and allow you to move forward regardless of how you feel. The best way to do this is to create a Never Zero commitment (see practice #3 in the previous article).


This happens when you simply forget to do your habit or to take action on your goal—either because you got distracted with other things, or because your commitment is very weak. You fix this by:


This happens when you know what you need to do, but choose not to do it, consciously or unconsciously.

We procrastinate because we are trying to avoid pain—be it physical, mental, or emotional. Therefore, there are only three ways to overcome procrastination:

  • Decreasing the pain of action: break down your task into Baby Steps, so that each step is so easy and clear that it taking action doesn’t involve pain anymore. (learn more)
  • Increasing the pain of inaction: become acutely aware of how procrastinating on this task is harming your long-term goals, hurting your self-esteem, and leading to a future that you will not enjoy. (learn more)
  • Embracing the pain: using either sheer willpower or the ROAR Method taught in the book, empower yourself to move forward despite the pain. You become larger than the pain, so then you don’t need to run away from it, feel afraid, or avoid taking action.

For a guided practice to help you overcome procrastination in the moment, try the Dissolve Procrastination and Shift Your Focus meditations in the MSD app.


Distraction happens when we prioritize pleasure over purpose, and instant gratification over our long-term goals. We do that because we have an opportunity to experience a quick and easy reward, here and now. A shiny object shows up and grabs our attention. The presence of such competing stimuli makes it difficult for us to stay focused and motivated in pursuing our long-term goals.

To become better at saying no to distractions, we need to first develop full awareness about what distractions are doing to our goals and mental health. I suggest you read chapter 22 of the book for that purpose, or check out the summary here.

The gist of it is this: distractions are not only wasting your time, but they are training you to have low motivation, poor focus, and low energy. They make you numb to your aspirations, desensitize you to further pleasure, and can lead to addiction, apathy, boredom, and a sense of meaninglessness.

Once you become fully aware of this, you can turn things around by adopting the principle of first purpose, then pleasure. You put this principle into practice by:

  • creating pockets of time in your day when you are focused by default, with no triggers for distractions, and ideally offline—such as your morning routine and Power Hours.
  • shifting away from distractions as they are happening via the Procrastinate Distraction and Shift Your Focus techniques
  • resetting your dopamine levels by following a Monk Week once per quarter, or at least once per year

In the free workbook, you will find detailed guidelines on a Monk Week and also a cheat sheet for the mindful use of technology.


Temptation happens when there is a pull to do something that you know goes against your values and better knowledge. Forcefully resisting the urge via sheer willpower rarely works. Here are some more effective techniques:

  • ROAR Method: this mindfulness intervention will help you recognize, observe, accept, and release the urge, without needing to follow it. You can learn more about it in this summary, or try the guided meditation in the app.
  • Negative Reappraisal: this ancient technique trains you to have an aversion toward the tempting object or activity. It is used by Stoics, Buddhists, Yogis, and also proved by modern science. You can read the summary here, or try the guided meditation in the app.
  • The Not Now Technique: this technique helps you to pause, take a step back, and “wait out” for the impulse wave to collapse. I’ve explained it in this short video.
  • Replacement Habit: the bad habit you are trying to break is a coping mechanism against emotional distress or boredom. That is the cue for the habit, and why it feels so tempting. See if you can replace the bad habit with a more positive coping mechanism—such as doing a minute of conscious breathing when anxious, instead of smoking. See this short video on the topic.

Finally, there is something to be said about making changes in your environment—or perhaps completely changing environment—so that you are not faced with temptation triggers all the time. This can be greatly helpful, especially in the beginning, but it’s not a permanent solution to the problem.


Excuses are actually not a real obstacle, but a way of masking the real obstacle and telling ourselves that it’s not a problem. The real challenge might be fear, self-doubt, procrastination, laziness—and we are just using excuses to rationalize our behavior.

You can overcome excuses by using the same techniques that we use to overcome low motivation: by cultivating your inner fire and making a Never Zero commitment (see section above). Besides that, I suggest going through the Challenge Your Excuses exercise, where you list the negative self-talk holding you back, and make a plan of how to counter each of them.

Other helpful elements are accountability, taking Baby Steps, and the Not Now Technique.


This is one of the most common and challenging obstacles to living your aspirations. Doubt can take very subtle forms and be difficult to spot, let alone to challenge. It is the virus of the mind, multiplying itself into hundreds of thoughts that weaken your resolve, make you depressed, and leave you confused.

There are three types of doubt: doubting the goal (“Is this possible? Is this good?”), doubting the process (“Will this approach work?”) and doubting yourself (“Can I do this? Do I have what it takes?”). These three doubts need to be replaced by the three convictions: “This is possible. This is going to work. I can do this!”

The challenge of doubt is often connected with traumatic experiences in our past, and so the path to fully overcoming it may require some deep emotional healing and mindset shifts—perhaps even reshaping your identity. Alongside this process, though, you can make use of the following tools so that you are not paralyzed, and can continue to take positive action:

  • The Not Now Technique: this allows you to trick your brain into giving you some space, right now, so that you can focus on what matters without being disturbed by doubts. It’s the “snooze button” in your mind. (learn more)
  • Shift Your Self-Talk: this is a process of using affirmations to counter the ingrained assumptions behind your doubts (see the guided meditation in the app).
  • POWER Visualization: this exercise trains you to take action despite doubt. You can combine it with the Baby Steps approach, to make the process easier. (learn more)
  • Shift Your Perspective: this helps you release unrealistic expectations that lead you to doubt yourself, such as perfectionism, false hope syndrome, and unfair comparisons.
Anxiety & Fear

Sometimes, embracing your aspirations or taking action on your goals can bring a sense of anxiety in you. It can stir up various fears. This is not necessarily a sign of lack of courage or motivation—it could be that there is a part in you that simply is not on board with that journey, and is trying to sabotage it.

If that is the case, the way forward is to meet that part in yourself, dialogue with it, and see if you can help it outgrow those fears. Or at least see if it is willing to give you some space to move forward regardless of the fears.

This process can be lengthy, and at times feel like you are opening a Pandora’s box. But if your goal is real self-transformation, this cannot be skipped. If you can, get support from a good therapist or coach for this process, as it can be a bumpy ride.

Another approach to overcoming fear or anxiety is to empower yourself by taking action and cultivating an identity of self-confidence. This involves feeling the fear and doing it anyway. Here are the key techniques to support this:

  • ROAR Method: this mindfulness intervention allows you to deconstruct the fear and down-regulate it to a point that it no longer holds you back.
  • POWER Visualization: use this technique to program your mind to face your fears successfully, moving forward resolutely, and achieving positive results.
  • Exposure Therapy: deliberately meet your fears by taking baby steps forward, and thus teach yourself that what you were afraid of is not that scary after all.
  • Enhancing Motivation: use the tools shared in the first section of this article to enhance your commitment to your aspirations, so that your fears and anxieties seem insignificant in comparison.

At times you will face failure. Things won’t work. Progress might be slow. Your expectations are not being met. Your best efforts are not rewarded. And the easiest thing to do here is to start doubting yourself and want to give up.

Having the right mindset and emotional tools to navigate these key moments can make the difference between continuing on the journey—wiser and stronger—or abandoning it altogether, feeling dejected and hopeless.

When you are facing failure, remember your aspiration, and why you started this journey. Reconnect to why this is important for you—how you will experience many rewards if you fulfill this aspiration, and face tremendous pain if you don’t. Fan your inner fire in this manner, and re-commit to your vision.

Then process the negative emotions that come with failure, by using either the ROAR Method or the ALFA Method. These will help you go through this experience in a more constructive way, and shorten the time you need to recover and start over.

If fear of failure is a recurring challenge for you, then you can take the 10-day Overcoming Fear of Failure course that is part of the MSD app.

👉🏻 Next Steps

There is a lot of content to digest in this page—so please don’t get overwhelmed. This is a big summary of all techniques to deal with these major challenges.

Your next step is to determine which of these nine obstacles is the biggest one for you, and then choose one or two techniques to try for that purpose. Once you have become proficient at them, then you can move on to other ones. Like this, step by step, you master the skills needed to live the aspiration-driven life.


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