How to Overcome Obstacles to Self-Discipline

This article is an excerpt from the Shortform book guide to "Discipline Equals Freedom" by Jocko Willink. Shortform has the world's best summaries and analyses of books you should be reading.

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Do you know how to overcome obstacles in life? What obstacles are getting in your way?

Even if you think you’re the most disciplined person alive, there will still be moments that will break you. In Discipline Without Freedom, Jocko Willink advises on overcoming obstacles that risk knocking you down.

Here are the different ways you can overcome difficult obstacles in life.

Overcoming Obstacles to Discipline

Even after you establish your underlying drive, set long-term goals, and begin to pursue these with incremental progress, your discipline can falter. We’re all human and nobody is perfect. Some days might bring overwhelming challenges or obstacles that are out of your control.

However, if you let obstacles stop you, you’ll disrupt your progress toward health, happiness, and long-term goals. Willink describes several strategies to learn how to overcome obstacles of procrastination, fear of failure, and factors that are out of your control.

Power Through Procrastination

Procrastination is problematic for several reasons. Willink points out that when you procrastinate, you stress yourself out. Delaying what you know needs to be done causes anxiety and dread. In a competitive context, delaying your progress can also allow your competition to get the upper hand. Worst of all, the things you procrastinate on now might be put off forever. Hesitation only inspires more hesitation in a self-defeating loop. Don’t get caught in the loop.

The fix, according to Willink: Don’t hesitate, take action. For example, get up when your alarm goes off. Throw your covers off and move to your feet before you can even think about slapping the snooze button. Starting your day with strict discipline will help you stay on that path for the rest of your day. For instance, because you got up when you were supposed to, you have plenty of time to get your workout in before work. 

On the other hand, if you fall off the path early, it’s easier to spiral and justify abandoning the rest of your goals. For example, If you hit the snooze button once or twice, you might not have time to exercise before work. So, you skip the workout. Since you don’t have to worry about eating too much before your workout, you might as well have an extra breakfast burrito…or two. Can you see the slippery slope?

Willink says you can set yourself up for success by removing things that cause distractions or unproductive contemplation. For example, silence your phone and remove it from your desk when you’re sitting down to work in the office or at home. 

Overcome Your Fear of Failure

Willink explains that another obstacle or excuse for not pursuing your goals is fear of failure. Maybe you fear applying for your dream job because you’re afraid you’ll botch the interview. Or perhaps you’ve been reluctant to ask the person you like out on a date for fear of rejection. These excuses, though they may be reasonable, can prevent you from applying discipline to become the best candidate for your dream job or a supportive, stable partner for the person you desire to be with.

Willink claims that fearing failure can stop you from acting at all. His solution: fear stagnation more than failure. Imagine in days, weeks, or years from now, being no closer to your goal or the best version of yourself, Willink says. Let the fear of all of this wasted time and potential spur you into action.

Decide to Succeed

The next obstacle to self-discipline is feeling inadequate because of genetic or environmental challenges. Willink asserts that, through discipline, you can adapt and overcome predispositions to live the life you decide for yourself. Maybe you don’t think you’re tall enough or you don’t come from the right kind of background for a certain goal. However, having these predispositions doesn’t mean you can’t succeed. Willink says he has seen people from many walks of life succeed in the military and business—he argues they succeeded because they decided to. The decision to succeed manifests as many decisions along the way, like deciding who you hang out with and deciding to work and study hard. 

Besides Willink’s anecdotal evidence, consider stories of people overcoming predispositions to achieve success. For example, Dustin Pedroia is a former MLB baseball player who was considered too short at 5 feet 9 inches to succeed in professional baseball. Despite his physical limitations, he worked hard and went on to earn the American League’s most valuable player award, as well as multiple World Series championships with the Boston Red Sox.

A Note on Self-Sabotage

Even if you agree with Willink’s point that success is a choice, maybe you fear success and intentionally sabotage your progress to avoid it. Willink says that if you intentionally fail because you think you’re afraid of success, you’re actually doing this because you fear the work it takes to succeed. Therefore, Willink claims self-sabotage is laziness.

Broaden Your Perspective on Challenging Situations

The final obstacle Willink discusses is uncontrollable circumstances. Sometimes life tests your discipline with challenges and setbacks. Maybe you’re let go from your job, become very sick, or lose a loved one. Willink suggests that putting your situation into historical context, accepting what you can’t control, and embracing challenges as opportunities can help you overcome difficult times.

The first thing Willink suggests doing during a challenging time is considering historical examples of what people have endured. By suggesting this strategy, Willink doesn’t mean to belittle your stress. Rather, imagining examples of human perseverance through terrible conditions is intended to inspire you to withstand your situation with more confidence and grit. In his own life, Willink draws inspiration from examples of soldiers who persevered through difficult conditions and got their jobs done.

Thought Exercises for Strength and Gratitude

Although Willink’s examples of imagining warriors’ suffering are useful, It might be more helpful to consider examples that relate more specifically to your difficult situation. If you’re a new mother struggling to keep up with the exhausting demands of a child, imagining the trials that new mothers endured migrating across the Oregon Trail might inspire strength and help you feel less alone in your suffering.

Consider using this similar thought exercise recommended by a neuroscientist: When you’re feeling stressed out and unlucky about a situation you’re experiencing, try to imagine a few terrible things that haven’t happened to you. For example, think about how you’re not starving or how you haven’t lost your home and loved ones to a natural disaster. Then realize these things are likely happening to people somewhere in the world at this moment. Imagine that—if you were experiencing these terrible things—you’d wish to be back in the situation you’re in. This should help you feel gratitude and endure stress better.

Next, accept what you can’t control and embrace it as an opportunity. When you’re faced with a challenge or setback that’s out of your control, Willink suggests viewing it as an opportunity to develop a new plan and improve in some way. For example, if an injury or illness prevents you from performing your regular workout routine, use your rest time as an opportunity to catch up on your reading list.

Besides difficult situations in the present, Willink notes that we often struggle to accept moments from our past. Accepting the past will free your mind of unproductive, stressful thoughts and help you focus on the present. You can’t change what’s already happened, so learn from your regrets and move on. 

(Shortform note: Stoics believe that every situation has a positive side—it’s just a matter of perspective. In The Obstacle Is the Way, Ryan Holiday explains that viewing challenging situations as opportunities for good also helps you overcome them. For example, if your car is rear-ended in traffic while you’re driving with your family, embrace this as an opportunity to handle the situation with grace and appreciate your family’s health. This will make the situation easier for you to cope with and allow you to support everyone involved more effectively than if you panic or get angry.)

How to Overcome Obstacles to Self-Discipline

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Like what you just read? Read the rest of the world's best book summary and analysis of Jocko Willink's "Discipline Equals Freedom" at Shortform.

Here's what you'll find in our full Discipline Equals Freedom summary:

  • Lessons and the philosophy of discipline from a Navy SEAL
  • The importance of daily habits like waking up early and putting off breaks
  • How self-sabotage actually stems from laziness

Katie Doll

Somehow, Katie was able to pull off her childhood dream of creating a career around books after graduating with a degree in English and a concentration in Creative Writing. Her preferred genre of books has changed drastically over the years, from fantasy/dystopian young-adult to moving novels and non-fiction books on the human experience. Katie especially enjoys reading and writing about all things television, good and bad.

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