How to Attack Obstacles Head-On

“What Stands in the Way Becomes The Way” 

-Marcus Aurelius 

The Obstacle is The Way, Ryan Holiday’s best-selling book based on principles steeped in Ancient Greek stoicism, argues that when we face impediments, it is best to view them as opportunities. By attacking our obstacles head-on, rather than trying to find a way to subvert or go around them, we take the shortest path to achieving our goals, and we often find ourselves becoming more creative and resourceful.

But attacking our goals head-on, especially when they feel large and unfamiliar, can be an intimidating task that sometimes feels impossible. We may not know where to start, become overwhelmed, and wind up defeating ourselves before we have even begun. How can we avoid this? How do we proceed when we feel we’re hit with an impossibly large obstacle? 

While there’s no exact science, we need to keep in mind that most enemies have been conquered before and can therefore be conquered again, which brings us to our first commandment: Perseverance

1. The Power of Perseverance

Building grit is not necessarily an easy feat, but this trait is directly related to attacking your obstacles when you feel overwhelmed. Those of us who don’t get discouraged due to past failures and instead keep going even when there seems to be no hope are the people who will eventually succeed. Simply keeping this in mind can be enough to power through for many people, but there are also tricks to building this trait that we can employ, which we have detailed in the article linked to above. 

Tips for building grit and persevering through tough times include starting with small commitments that are easy to follow through on, remembering past times you have triumphed in a similar situation, and building a level of calmness and clarity through mindful practices like meditation. These tactics can help you build confidence, help you see things more clearly, and keep the big picture in mind, allowing you to soldier through when you may otherwise feel like quitting. 

2. Look to Examples From The Past 

There are multiple ways that looking to the past can help you march toward the future. First, remember your own past and times you have conquered obstacles that at one point seemed impossible. As we grow and our perspective changes, we all have experiences that we can look back on and realize how much we have grown. 

Remember in college when finals week felt like it was going to kill you? When you were assigned a 10-page paper and literally didn’t know if you could hack it? How much would you love to go back to finals week now? That was a breeze compared to how busy most of our lives have become since then. I would crush a finals week right now without losing a wink of sleep. 

Contemplating how that obstacle that once felt so big turned out, in retrospect, not to be that big, can help us realize that things may feel bigger than they are sometimes. As long as we remember that, we know that we can keep conquering bigger obstacles. Now it just becomes a game to see how mighty we can really become. 

It’s also useful to consider the paths others have taken. Read the stories of people who have battled some of the same things we have, there may be insights in their story that we can apply to our own lives. At the very least, we can derive a lot of inspiration from such stories. 

3. Try to Fail As Many Way as Possible 

If you don’t know how to succeed, then challenge yourself to fail as many ways as possible. Set out to fail more times than anyone else ever has at achieving your goal. Do things even if you know they will fail, then move on to the next method. Often, something will shake loose or an idea will be sparked, illuminating a better plan of attack. 

When you set out to fail, failure itself becomes success. If it’s your goal, if it’s seen as a research mission, then there’s nothing to fear. Whether it’s finagling your first freelance job, landing that Google interview, or learning to speak Japanese, actively seeking some failure can lead to long-term success. So fail, my friends, set out to fail as often as possible, and eventually, you will start failing to do so. 

4. Take a Breather and Find a Different Perspective 

Attacking our goals head-on does not mean that we have to constantly be attacking without relent. In fact, research shows that this is probably a terrible idea. You have a certain number of work hours in you per day, and accepting that will help you get the most out of them. Burnout is real, and once the fatigue sets in, you’re simply not going to bring your A game. This might be ok for some tasks, but if you’re trying to conquer an impossible obstacle, it may just be that heading home early, eating some vegetables, and getting a full 8 hours of sleep is your best plan of action. Too many entrepreneurs forget or simply don’t know this maxim. 

Carve out time every day to not think about anything work-related. Go eat a little more ice cream than you should with a friend, take your dog for an extra-long walk when they’re not expecting it, or do whatever else you need to in order to recharge your batteries. Extensive research has shown that many of the most creative ideas occur right after you have given up on trying to grind them out. Entire books have been written during a 2-week vacation after the author was stuck with writer’s block for the prior 2 years. 

Accept it. It’s almost 2020, self-care is real, and if you want to conquer your goals then you better start to take it seriously. 

At the end of the day, attacking your goals head-on is a way of thinking. It’s a way of training your mind, committing to a path, and pushing forward. Many of the most esteemed people in our society subscribe to this mantra, and it has a proven track record of delivering results. Stick with it. Learn to persevere and practice it every chance you get, even in the small moments. Remember your past successes and learn from the examples of those that came before you. Challenge yourself to fail until something finally clicks. 

And at the end of the day, every day, relax. You’re not a machine, and if you don’t know how to enjoy your life, then what’s the point in conquering goals to begin with? 

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