Life is not a walk in a park on Sunday afternoon. Each of us faces all kinds of obstacles in both personal and professional life. And while not all barriers can be crossed–sometimes we have to accept them and move on, it’s your attitude to overcoming obstacles that interests the interviewers.

Are you ready to make sacrifices when trying to achieve something in life? Can you step out of your comfort zone when situation demands it? Do you give up easily, or do you never give up? And when you finally overcame the obstacle on your way, didn’t ten other obstacles appear in front of you?

Your answer to this question tells a lot about your personality. Hence it makes sense to ask it in almost any job interview. Before we look at 7 sample answers to this question, I also want to list a couple of alternative wordings of this question you may encounter while trying to get any great job:

  • Think of a time you overcame a challenge or obstacle. Describe the experience in two to three sentences. (A typical question on many job application forms in the US.)
  • Can you tell us about a time when you achieved something for yourself or for others by overcoming significant odds? (Popular in some big corporations in the US.)
  • Tell us about a time when you wanted something so badly you were unstoppable in pursuing it? (A less common wording, but I have seen it a couple of times both in the interviews and on job applications).

Anyway, regardless of the chosen wording, they are always looking for the same things in your answer. Let’s have a look at some great sample answers.


7 sample answers to “Think of a time you overcame a challenge or obstacle. Describe the experience in two to three sentences” interview question

  1. I was super introverted as a child, which was a result of some traumatic experiences I had in my early childhood. It had a profound impact on both my relationships and professional career. I would just sit and listen in the meeting, often answering questions with silence, my eyes downcast. But I eventually found a courage to work with a psychologist, and to undergo a therapy. As I result I overcame my mental block, started to trust people again, and even started a relationship. It wasn’t an easy process, but I did not give up, and here I am, living quite a normal life now, and interviewing for a great job with you.
  2. My biggest obstacle was to get to vet school. I didn’t have best grades, because when I was younger I didn’t understand the importance they’d have on my future studies and career, and I wasn’t responsible enough to excel in school. I failed to get to a vet school two years in a row. Many people would give up and try something else, but I decided to follow my dream, though I knew I had to overcome significant odds. While not studying I tried to get experience from veterinary practices and zoos, because I believed it would help me in my application. This eventually turned out to be true. I got to vet school, earned my degree, and now I apply for a job with you.
  3. I do not like the word obstacle. In my opinion, most limitations and obstacles are self-imposed. One can reach as much as they imagine. It’s just about having ambition and dreaming big, regardless of what the others are saying. Sure, everyone is not born into a good family, having resources to study and to pursue their dreams. But even if you are lucky, just as I was, you still have to overcome your laziness, step out of your comfort zone, and stick with one thing long enough to succeed. That’s what I’ve been trying to do up to this point.
  4. My health was my biggest obstacle. I had bowel issues all my adolescent life, and also problems with food allergy and intolerance, and some related health issues. But I was brave enough to try different diets, though I faced an opposition form my family and also the doctors weren’t supportive of such drastic changes. Eventually I found out that vegan diet, based primarily on cooked vegetables and legumes, works best for me. I got rid of almost all health issues, and can finally function normally in my daily life. I can tell you it was super hard to switch to this diet, since I was addicted to sugar, coffee, and other things, but I wanted a better health so badly that I was unstoppable in pursuing it, and ready to overcome any obstacles on my way.

* May also interest you: 30 most common behavioral interview questions.

  1. I remember a good situation from my last job. We tried to develop an innovative mobile app, with a goal to help with screening for certain common diseases. But the project was very innovative, I didn’t have full support from the management, and they didn’t allocate sufficient budget for the project. Well, I could have just given up and moved on. But I didn’t do that. I pleaded with them, presented more and more arguments, because I knew that if we succeeded, we could have built the next big thing. Eventually I managed to convince the managers, and they extended the budget. We eventually didn’t succeed with our goal–the app wasn’t accurate enough to break into mainstream use. But I am still glad that I tried, and overcame an obstacle.
  2. To be honest, I haven’t overcome any huge obstacles yet in my life. I am lucky enough to be healthy, and to somehow thrive in most things I do. I know that some obstacles will come, later on, both in my personal and professional life. And I hope to be ready to face them. My goals and ambitions should drive me forward, and help me overcome the obstacles on my way. My life has been easy up to this point, but I know that things can turn around pretty quickly. I believe to be ready for such a turnaround.
  3. I carried the biggest obstacles within. My complexes and my prejudice helped me to open up to the world, to have some impact, and most importantly to live freely and happily. Just recently I learned the most important skill in life–if we can call it a skill–to live in a present moment. Giving my full attention to the activity I am doing–be it teaching, cooking, playing, anything, I am not anymore imprisoned by those thoughts … what other think about me, whether I am a success or a failure, etc. Now I understand that such questions aren’t important at all. Overcoming this obstacle was the most important thing in my life.


Open up about your problems and make a connection

It takes some courage to talk about your personal or childhood problems in an interview. Some traumas you experienced, demons you battled with, mental blocks you had to overcome.

If you have such courage, however, it can be a very powerful interview answer. First of all, each hiring manager will appreciate your honesty. Seeing how open you are while talking about your life, they won’t doubt the credibility of your other answers.

What’s more, they will certainly remember what you said. And it is important that they remember you once the interviews end, and they are deciding about the best candidate, or who moves into the next interview round.

* Special Tip: This isn’t the only difficult question you will face while interviewing for any decent job. You will face questions about prioritization, dealing with pressure, dealing with ambiguity, and other situations that can happen in the workplace. If you want to make sure that you stand out with your answers and outclass your competitors, have a look at our Interview Success Package. Up to 10 premium answers to 31 tricky scenario based questions (+ more) will make your life much easier in the interviews. Thank you for checking it out!

Employers like the never give up attitude

Maybe you failed in ten other interviews, but you are still here, trying your luck again. Or you did not get to the school of your choice. Instead of opting for a simple job and quick buck, you worked on your preparation, gained some valuable experience and tried again. You failed, but you failed better. Again it did not discourage you. Never giving up and wanting it badly, you eventually succeeded.

Working life is not easy. You will face conflicts, deadlines, sometimes seemingly unrealistic goals. Once you have the “never give up” attitude, however, you will continue even when others already quit. And that’s exactly what the employers love to hear.

* Do not forget to check also: How to dress for an interview? 5 things to consider when choosing clothes to wear.

Do not restrain from philosophical answers

One thing that is really missing in young generation, at least in my opinion, is creative thinking. Leading interviews, we hear the same answers each and every time, maybe with a slight adjustment here and there….

But what if you said that you did not believe in obstacles, that all limitations were self imposed? Or when instead of obstacles you faced in work or school you talk about obstacles you carry within? Or you may even say that you were lucky enough to face no big obstacles–with your place of birth, good upbringing, and love all around.

Interviewers do not expect such answers, but they are a clear indication that you can think outside of the box, and do not stick to the same way of thinking and doing as most people. And that’s not a bad impression to leave in the interviews, especially when you compete with many other people for a lone vacancy, and try to stand out from the pack. Keep it on your mind when thinking about your answer to this tricky question.

Ready to answer this one? I hope so! Check also 7 sample answers to other tricky interview questions:

Matthew Chulaw
Latest posts by Matthew Chulaw (see all)