Overcoming Obstacles: 7 Questions for Breaking Through

How to solve problems fast so you don't lose your momentum and excitement.

The good things in life go to those who fight through challenges and keep overcoming obstacles. All day long we face large and small hurdles that can make us want to give up or give in.

Struggle makes things special. No struggle, not special.

The good things in life go to those who fight through challenges and keep going. Click To Tweet

Life is saying to us, “You say you want this? Prove how much. Fight for it. Earn it.” Overcoming obstacles is a big part of earning it. 

There’s always going to be resistance you have to overcome to accomplish anything positive you want to have happen. The more tools you have to overcome these forces, the more likely you are to be able to stay in control and win. 

There’s a lot of satisfaction once you reach your goal, but there is also daily satisfaction you will get as you navigate through these things that pop up and cause others to quit. 

Hurdle on a track to represent overcoming obstacles.

Let’s say you like to play tennis. Of course you like to win the match, but if you really like tennis, you like mastering all of the different shots and being able to handle whatever your opponent sends back over the net at you. 

It’s the same in all sports, board games, and even video games. The challenge is in overcoming the obstacles.

It’s just like video games, once you master a certain level, you advance to another level. The better you get, the higher scores you post.

Learning how to overcome obstacles in life can turn into a lot of fun for you, because it’s not just a matter of kicking annoying things out of your way—it’s a matter of playing the game of life efficiently, enjoying the satisfaction of dodging the bullets that come at you, and continuing to move forward. 

Overcoming obstacles in one area gives you tools for dealing with them in other areas. Because, to repeat the point, ANYTHING you want to do in life will present resistance you have to overcome to make it happen. 

What Most People Do When Things Go Wrong 

New projects are fun and exciting. You start thinking about all the possibilities and how this could really be a great thing. You’re excited about accomplishing your new goal and motivated to get started right away.

Things are going well. You’re plugging away and getting things done. You’re really starting to see some progress. 

And then . . . BAM! You hit a roadblock. All progress comes to a halt. 

What now? 

Woman who look stressed and overwhelmed.

The vast majority of people are overwhelmed when things go wrong and feel like the rug has been pulled out from under them. Their emotions get the best of them, and instantly their enthusiasm for the whole project is gone. Just like that. 

When they started, they were overjoyed. But now they are totally disoriented by a whirlwind of negative thoughts that feed off one another. ‘Everything is ruined. I can’t believe I’ve wasted all this effort. It’s all his/her fault. I can’t believe I thought this was possible. Guess I’m just not good enough. I quit.’

Staying in this irrational frame of mind is detrimental. Dwelling on the negative consequences of a potentially failed project can make you feel even more overwhelmed. Placing blame on yourself or others doesn’t solve the problem. And giving up leads to an empty life of unfulfilled hopes and dreams. 

What can you do instead? 

Toughen up. Get a plan. Get some new ideas. Don’t take the easy way out because it will send you right back to where you started. 

Toughen up. Get a plan. Get some new ideas. Don't take the easy way out because it will send you right back to where you started. Click To Tweet

It’s easier to figure out your next step and keep overcoming obstacles than it is to throw up your hands, quit, and have to start all the way at the bottom again. 

Stay the Course

Some problems are random and only happen once. Others are predictable and recurring. There’s no way to have a plan in advance for all the one-time events that show up on your doorstep, but you can certainly create a plan for handling the recurring problems. Here’s an example. 

Mad walking through airport.

I have a place in Aspen, Colorado. I got it once I decided there’s no reason to be cold in the winter if you can’t go outside and ski, and there’s no reason to bake in the heat and humidity in the summer when you could spend your time in a place with 70-degree temperatures and no humidity. So winters and summers usually find me in Aspen. 

It’s great, but they have a small airport. The problem is the weather and wind can cause frequent flight cancelations in and out. 

It’s happened many times now that I’m all packed up, made my way through security, and arrive at the gate only to find out that my flight has been canceled.

Rather than get upset, waste time talking to the airport staff, and make a big fuss, I immediately head to the car, get on the highway, and call my office. 

There are two other airports within a couple hours driving distance. By the time I make it to where I need to turn, my office calls back, tells me which airport to go to, and sends me a new boarding pass. 

I’m not going to cancel my entire trip just because my flight was canceled and let it ruin my plans. I make an adjustment and stay the course.  

At any point, you could be just one small adjustment away from a major success. 

At any point, you could be just one small adjustment away from a major success. Click To Tweet

7 Questions for Overcoming Obstacles 

A study related to overcoming obstacles, done by the Society for Personality and Social Psychology, showed people are better at solving problems for others than for themselves. When people are able to objectively think about a problem, they are more likely to use logic and come up with a creative solution that actually works. 

To help you think clearly in the face of overwhelming challenges, I’ve created this list of 7 questions for overcoming obstacles to help you break through.

Apply it to any obstacle or problem to figure out at least one thing to do next, and that’s what matters. The way to move from survival to success is one inch at a time.

The way to move from survival to success is one inch at a time. Click To Tweet

Man breaking through wall as a metaphor for overcoming obstacles.

1. Do I have the facts?

I’ve said it many times: use facts for guidance, emotion for fuel. But you need to make sure you actually have the facts if you want to make smart adjustments.

Do you understand the details of the problem or obstacle? Do you know who the players or people involved are? Is there any relevant data you can gather (financials, schedules, website traffic, customer demographics, etc.) that can give you better insight? Do you know what you want to do?

Have you ever heard the advice to “stay in the moment”? This is what it means. Stay focused on what is really happening right now and deal with it right now.

Facts give you a fighting chance, a competitive edge, so make sure you’ve got them.

2. Have I simplified the issue?

Good, effective decision making starts with the ability to take a complex issue and boil it down to its simplest components. When you’re facing an obstacle, that often means getting to the core of why it exists and what it will take to eliminate it.

Try using the “5 Whys” technique that I described in a previous post. 

The simpler you can make a problem, the faster you’ll be able to move past it. 

It’s good to have information or data before you go through the exercise. It will make the answers more apparent.

3. Is this my problem to solve, or somebody else’s?

A lot of people waste a lot of time on problems that aren’t theirs to solve. If you’re facing an obstacle that is keeping you from making progress, you need to do something about it. But the source of that obstacle might be a problem that somebody else has to solve.

If that’s what your facts or analyses reveal, find that person and make sure they know it. You might have to convince them to make it a priority. And if they won’t or can’t, you might have to adjust and come up with a different plan that allows you to bypass the problem entirely.

4. What are my strengths in this situation?

You can leverage any of your personal strengths when trying to solve a problem, but when you’re facing a specific obstacle, you need to think about specific strengths.

More than personal traits, think about resources, relationships, networks—all strengths—that you can put into play to help you solve a problem or move past an obstacle. 

Make a list of the most relevant, and think about how each could help.

If you are still overwhelmed, bring in the cavalry! 

When you’re too proud to ask for help, you handicap yourself. 

When you're too proud to ask for help, you handicap yourself. Click To Tweet

Your supporters are a strength. They can give you the insight and encouragement you need to get over the hump. Call them, find them, get their input and keep moving.

5. Do I know what the people involved think?

Don’t ignore the opinions or assessments of those closest to the situation or those directly involved. They have the most information and the best instincts. 

Ask for their input. Go overboard to get them to open up and tell you the truth about the situation. It will help you see if you have been attacking the issue from the wrong angle.

Even if you don’t agree with their conclusions, you need to know what they are thinking and why.

6. What do people who’ve tackled this obstacle successfully have to say?


If you are still stumped, keep digging. Start online—amazing, talented, successful people are giving away advice for free in their blogs, on YouTube, and everywhere else. 

Read interviews with the best and brightest. Join forums. Read books about the particular challenge you’re facing. Work on gathering a good list of starter options.

Talk to people who are doing well and get some fresh input. Explain what you’ve tried to do and why you think it’s not working. Ask them for their opinion or for any stories of how they’ve overcome similar challenges.

7. What can I do right now to move forward?

Serial winners handle disasters the same way they handle successes: they maintain their focus and keep moving forward.

 The first step in becoming great at something is getting obsessed about getting great at it. No obsession = no greatness. 

Action tests ideas,” is a favorite saying of John Paul Caponigro, a photographer and artist.

What’s the next step in your plan? If it’s not possible, what action can you take to move a little closer to it? If your plan has blown up, what’s the best viable alternate route you can take?

Overcoming obstacles is what propels you towards what you really want in life. When you rise to the challenge and find ways to make timely adjustments, sometimes you find an even better course of action than your original plan.

Winning is simply the process of making a series of adjustments. If you ask these questions and work to get good answers, each setback will be just a bump in the road, not the end of the road.

Whatever it takes, simplify your options, pick the one that pops out to you as the best, and keep moving towards the things you want! That’s what serial winners do.

Did you like this post on overcoming obstacles? Let me know what was useful to you in the comments below.

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