Life isn’t short on obstacles—it’s full of them. But sometimes, the best way to get through tough times isn’t by grinding harder; it’s by laughing a little. Humor and wit can lighten even the heaviest burdens, turning challenges into punchlines and struggles into stories worth sharing.
In this post, you’ll find over 80 funny, clever, and sarcastic quotes about overcoming obstacles. Each one has a spark of wisdom and a wink of humor that will leave you smiling, thinking, and maybe even a bit inspired.
Quotes About Overcoming Obstacles
1. Motivation with a Twist
- “People are always blaming their circumstances for what they are. I don’t believe in circumstances… the people who get on in this world are the people who get up and look for the circumstances they want, and if they can’t find them, make them.” ― George Bernard Shaw
- “Always listen to experts. They’ll tell you what can’t be done, and why. Then do it.” ― Robert A. Heinlein
- “The greater the obstacle, the more glory in overcoming it.” ― Molière
- “Well, if it can be thought, it can be done, a problem can be overcome.” ― E.A. Bucchianeri
- “It was so risky and so scary, and yet at the same time, so beautiful… It’s the things you fight for and struggle with before earning that have the greatest worth.” ― Sarah Dessen
- “Never trust someone that claims they care nothing of what society thinks of them. Instead of conquering obstacles, they simply pretend they don’t exist.” ― Tiffany Madison
- “I am more than my scars.” ― Andrew Davidson
- “Those who don’t know how to suffer are the worst off.” ― Deng Ming-Dao
2. Funny Takes on Failure
- “Behind every successful person is a long line of failures who didn’t quit. And several who did.”
- “If at first you don’t succeed, redefine success.”
- “I didn’t fail—I just found 100 creative ways to go in the wrong direction.”
- “Obstacles are like bad dates: you’ll never see them again if you stop giving them attention.”
- “Every failure is just success wearing the wrong outfit.”
- “Don’t call it failure, call it ‘plot development.’”
- “They said, ‘You can’t.’ I said, ‘Watch me trip over trying.’”
- “My obstacles didn’t stop me. They just gave me a better story for when I finally succeed.”
3. Sarcastic Wisdom About Challenges
- “Nothing says ‘I’m growing as a person’ like repeatedly hitting the same wall.”
- “What doesn’t kill you makes you wish it had an easier mode.”
- “Overcoming obstacles builds character—or at least gives you good material for small talk.”
- “Challenges are like relatives: you can’t always avoid them, but you can limit your exposure.”
- “They told me to follow my dreams. So I took a nap.”
- “Every obstacle I’ve overcome has introduced me to a bigger one. Progress?”
- “Sure, obstacles make you stronger. But have we tried not having them?”
- “If life gives you lemons, ask for coffee instead.”
4. Witty Motivation for Tough Times
- “Courage doesn’t always roar. Sometimes it quietly mutters, ‘Let’s just get through this meeting.’”
- “You can’t climb the ladder of success with your hands in your pockets—or your phone in them.”
- “I’ve learned more from my mistakes than my victories. Mainly because I make more of them.”
- “Sometimes the only obstacle in your way is Wi-Fi that won’t connect.”
- “Hardships build character, but can’t we just buy character online now?”
- “The road to success is full of speed bumps. Luckily, I drive a metaphor.”
- “You can’t control the storm, but you can sarcastically comment on the weather.”
- “Overcoming obstacles: the polite term for surviving chaos.”
5. Clever Reflections on Persistence
- “If you’re going through hell, keep going—and maybe grab a souvenir.”
- “Winners never quit, but they do take strategic naps.”
- “The only difference between stumbling and dancing is confidence.”
- “Persistence: doing the same thing again, but with more caffeine.”
- “Success is like Wi-Fi—you keep moving until you find the signal.”
- “Don’t give up. Even the GPS recalculates.”
- “Obstacles are temporary. Regret is permanent (and more annoying).”
- “I’m not stubborn, I’m just dedicated to finishing the wrong idea properly.”
6. Inspirational Yet Ironic Insights
- “You don’t truly know your strength until life forgets to go easy on you.”
- “When one door closes, try the window. Or the back entrance.”
- “Overcoming obstacles teaches patience—mostly with yourself.”
- “Sometimes, your biggest obstacle is convincing yourself it’s worth trying again.”
- “Every challenge you beat adds another story to your highlight reel.”
- “Life’s not about avoiding storms—it’s about pretending you like the rain.”
- “Sometimes, strength looks like taking a nap and trying again tomorrow.”
- “Even when it feels impossible, it’s still worth starting.”
7. Sarcastic Lessons from Life’s Challenges
- “Life keeps throwing curveballs. I’m thinking of signing up for baseball.”
- “They say obstacles are opportunities. I say they’re mislabelled headaches.”
- “If you’re facing an obstacle, congratulations—you’re still in the game.”
- “Everything happens for a reason. Usually bad planning.”
- “Obstacles don’t block the path; they are the path. Unfortunately.”
- “Sometimes life shuts a door so loudly you start checking for fire exits.”
- “Falling is part of flying. Just less graceful.”
- “Who needs comfort zones when you can live in constant chaos?”
8. Philosophical Humor About Adversity
- “Suffering is temporary, but the memes last forever.”
- “Pain builds wisdom—and a very dry sense of humor.”
- “Obstacles are life’s way of saying, ‘Still want this?’”
- “Sometimes the universe tests you just to make sure you’re paying attention.”
- “The obstacle isn’t the enemy—it’s the unpaid intern of destiny.”
- “Growth hurts because it’s stretching your comfort zone into something stylish.”
- “Every hardship hides a lesson. Usually one you’d rather skip.”
- “The mountain’s tall, but the view’s worth the climb—and the sarcasm.”
9. Overcoming Fear and Doubt
- “Courage isn’t the absence of fear—it’s doing it anyway and regretting it later.”
- “Fear is just excitement with bad marketing.”
- “The scariest obstacles are usually the ones in your head.”
- “Doubt kills more dreams than failure, but failure at least gives you a story.”
- “Confidence is pretending you know what you’re doing until it works.”
- “If you wait for the perfect moment, you’ll miss the bus.”
- “Being brave doesn’t mean being fearless—it means acting while terrified.”
- “Fear is temporary. Regret has a longer subscription.”
10. Laughing Through Life’s Struggles
- “If life were easy, we’d all be bored.”
- “Obstacles make you interesting. Smooth sailing makes you sleepy.”
- “When life gets tough, remind yourself: it could always be Monday.”
- “A little struggle builds strength. A lot builds sarcasm.”
- “Every obstacle is a plot twist. Keep reading.”
- “Smile—it confuses your problems.”
- “Some days you conquer the mountain; other days you just roll down it.”
- “The best stories start with ‘So there I was…’ and an obstacle in the way.”
Conclusion
Overcoming obstacles doesn’t have to be all grit and grind. A little humor can turn frustration into perspective and fear into laughter. These quotes show that even when life gets messy, a witty outlook keeps us grounded and smiling.
Which of these lines hit home for you? Share your favorite in the comments, or drop one of your own. And don’t forget to share this collection with someone who needs a reason to laugh through their next challenge.