Setting a goal is the easy part. The hard thing is overcoming the obstacles to get you to said goal. The good news is that most people see obstacles, and they quit. Your chances of success are much better when you can continue to overcome obstacles.

Figuring out how to do it is where most people get stuck. Having the will to do it is one thing, but the know-how is a different story. There are 10 different things that you can start working on today to make sure that nothing gets in the way of where you want to go.

“Being challenged in life is inevitable, being defeated is optional.” – Roger Crawford

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Why You Must Overcome Obstacles

You can accomplish nothing without being able to overcome obstacles. You know the phrase coined by Biggie Smalls "Mo Money, Mo Problems." As you acquire more money, people think the problems go away when in reality, they get more frequent. Everyone wants a piece of you when they know you have money. 

Obstacles are challenges that slow down your progress. Anything that prevents you from moving forward and the pace you wanted to can be considered an obstacle. They are designed to frustrate you, and they can come from many different sources like: 

  • Ill-health
  • Weather
  • Enemies
  • Policy changes
  • Mistakes
  • Lack of Resources 
  • and much more

Obstacles represent the opportunity to grow. When you look back in your life and see obstacle after obstacle that you overcome, you know that you have gotten stronger. 

Obstacles force you to think differently, be agile, and, most of all, they force you to be resilient. The definition of resilience is "an ability to recover from or adjust easily to misfortune or change. 

Once you discover that you have resilience, nothing can stop you. It means that nothing folds you. Everything that happens to you is seen as an opportunity instead of a curse. 

10 Ways to Overcome Obstacles

1. Adopt a Stoic Mindset

When you're stoic, it means that you can endure pain without showing emotion or complaining about it. It's a very rare quality for a modern society obsessed with making things as easy as possible. We need our dishwashers, hot water, robotic vacuums, and we have lots of snacks on hand at all times.

When you decide to be stoic, you even begin to do things to test yourself and make your life hard. You have cold showers or cut off the AC to make your life uncomfortable, yet you don't complain. The stoic mindset helps you to get through any obstacle while staying focused on the solution.

2. Approach it in a Radically Different Way

You want to try and look at your problem differently. The definition of insanity is trying the same stuff over and over and being surprised when you get the same result. Instead, try something new and learn from that experience.

When you look at transformational companies like Tesla, or Google, the thing that stands out is how they have done things in a radically different way. They did not jump on the status quo.

3. Acquire New Perspectives

Looking for different ways may be difficult with a limited perspective. The easiest way to get a new perspective is to learn from very different people from you. When you read a book or takes someone's course, it gives you an insight into how they see the world.

The more you learn, the better of an understanding you will have of how others cleared the same obstacles you have. Your problems are not new. There is nothing new under the sun. You need to find the right course, class, or book to consume to adopt the perspective that will work for you.

4. Size Up The Obstacle

Take time to understand the obstacle in an in-depth way. How can you overcome an obstacle that you don't fully understand? People try and do this all of the time to no available.

For example, let's say your obstacle is debt. Understand how you get into debt. What mistakes did you make, and why is debt bad? In what ways is debt making it harder for you to move forward.


Most people spend 2 minutes thinking about the problem and then focus all of their time on the solution. You should spend as much time dissecting the problem, and it will be easier to find a solution.

5. Get Qualified Advice

The keyword here is qualified. You want to get advice from someone who has experience overcoming your exact problem. There are many people who can give you advice and their opinion, but they are not as valuable as someone who has done what you want to do.

Learn from the mistakes and the success of others. It's the fastest and least risky way that you can learn. When you learn through trial and error, it can take a lot of time, and your time is your life.

6. Stay Motivated

Motivation is a personal experience. Whatever works to keep you motivated, you need to stick with that. Remember your why as well. If you're doing this for your family or status, be honest about what is driving you.

When you're honest about what is driving you, its easier to stay focused on that. If you need to watch motivational videos or talk with a particular person, do it. Overcoming obstacles can be difficult and make you want to quit altogether.


7. Be Held Accountable

If you want to create lasting change that can allow you to conquer an obstacle, get held accountable by someone that you respect. The last thing you want to do is let down someone that you respect.

Being held accountable means that there is someone who is checking in with you and your progress. They know where you are and where you want to go, and they will make sure that you got there.

8. Go Above, Under,  Around or Through

To get past an obstacle, you only have so many ways that you can go. 

  • Above - When you surpass it all together
  • Around - Finding a new way to do things 
  • Under - Getting dirty and changing the entire system at its roots
  • Through - Going through is taking it straight on

You have to pick your approach and go full bore. When someone sees the criminal justice system as an obstacle, for example, they often try and go under it and change the system at its roots. 

None of these approaches are better than the others. You have to figure out the way that works best for you and the resources you have. 

9. Don't Exhaust Yourself

Think about Muhammad Ali and the rope-a-dope. His strategy was simple, let people get free body shots on him in the early rounds so that they tire out for the later rounds. 

You have to remember that whatever you're chasing is a marathon and not a sprint. You need to have the energy for later fights as well. You don't have the time or energy to waste punches on every obstacle.

Don't expend all your energy on one obstacle unless you have to. If you have to give it your all, make sure you get adequate rest after or you will burn out in the last round. 

10. Recognize the Small Wins

Throughout everything happening, you have to take time to celebrate the small wins along the way. When you have a significant obstacle in your face, it can feel like you're making no progress. You have to look for improvement.

If you don't look for progress, you won't find any.

Obstacles Never Stop Coming 

No matter how successful you are or how many obstacles you overcame yesterday, they will never stop. When you die, you stop seeing obstacles, but as long as you're breathing, you will have issues.

You will see obstacles come from every direction you can imagine. Some seasons will bring more than others, but it's naive not to expect them to come your way. When you know something is coming, you can re-frame how you see it.


If you see an obstacle as an opportunity instead of a problem, you will see it positively. Instead of it ruining your life or frustrating you, you will see it as a chance to weed out your weak competitors or as a chance to get better.

To Make The Journey Valuable You Must Overcome Obstacles

Think about wanting to become a millionaire. The reason it's valuable is that it's FULL of obstacles. No one is going to hand you a million dollars. There are a lot of things you have to get right before you can even get on the path to becoming a millionaire.

You need to clear out debt, develop multiple streams of income, learn to invest, and preserve money and so many other things. Each obstacle that presents itself makes the end goal that much more valuable.


When you look back on the journey, you have taken until now, and you can be most proud of what you had to overcome. This happens because you know that most people see roadblocks and turn and go the other way. Most people want the rewards of life, but they want them to come easily.

Ian Warner

About the author

I went from a broken leg to a 2012 Olympian. I have spent the last 15 years building positive habits as a track athlete and entrepreneur. I founded Habit Stacker and dedicated my life to helping people to develop winning habits. I have helped over 5,000 people...

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