Challenging Sayings and Quotes

Below you will find our collection of inspirational, wise, and humorous old challenging quotes, challenging sayings, and challenging proverbs, collected over the years from a variety of sources.


Life can be challenging and sad... but music is the easy part.     

St. Vincent

If there is no challenging of the sinful heart, there is no gospel preaching.     

Darrin Patrick

The further you get away from yourself, the more challenging it is. Not to be in your comfort zone is great fun.     

Benedict Cumberbatch

Magic lies in challenging what seems impossible.     

Carol Moseley Braun

Keep challenging yourself to think better, do better, and be better.

Robin Sharma

As for what's the most challenging aspect of teaching, it's convincing younger writers of the importance of reading widely and passionately.     

Chang-Rae Lee

The most challenging part of being a boss is that nobody will tell you if your work is suffering.     

Bill Williams

One of the more challenging things in life is not being the guy who does the cheating, but not saying anything about it and going along with it.     

Dale Murphy

Sustaining true friendship is a lot more challenging than we give it credit for.     

Mariella Frostrup

The goal you set must be challenging. At the same time, it should be realistic and attainable, not impossible to reach. It should be challenging enough to make you stretch, but not so far that you break.     

Rick Hansen

The challenging times will bring you closer together in marriage.

Bill Rancic

Challenging the meaning of life is the truest expression of the state of being human.     

Viktor E. Frankl

It's challenging to find an identity as a young person if you don't have the sustenance of love, because you're being shipped around.

Mary J. Blige

The most challenging part of being a dad is self-restraint. So often your instinct is to teach and tell. I am constantly reminding myself to listen to them.     

Michael Chiklis

Writing is challenging work because it's so easy to get consumed with how it's going, what's going to happen to it, who's going to like or not like it. You want to get all of that stuff out of your head and just let the work flow.     

Wayne Dyer

It's hard to balance everything. It's always challenging.     

Vera Wang

Dreams can often become challenging, but challenges are what we live for.     

Travis White

Maturity is about Challenging yourself and Improving! And then taking that experience to help others…

Tsem Tulku

Challenging the integrity of the non-proliferation regime is a matter which can affect international peace and security.     

Mohamed ElBaradei

Love is a complicated emotion because you can learn something or hear something that goes against what you have come to know personally. It can be very challenging to what you believe.

Aja Naomi King

Opportunities to find deeper powers within ourselves come when life seems most challenging.     

Joseph Campbell

Challenging someone is good. You need to do it. Sometimes they don't even realize you're doing it, like when you joke with a goalie, 'What's wrong today? You losing it?     

Sidney Crosby

We don't develop courage by being happy every day. We develop it by surviving difficult times and challenging adversity.     

Barbara De Angelis

The only thing as challenging as getting tangled in the underbrush of relationship is trying to write about it.     

Thomas Moore

Friction and misunderstandings often occur when communicating across generations. It gets even more challenging when working across virtual settings.     

Raymond Arroyo

Dreams have always expanded our understanding of reality by challenging our boundaries of the real, of the possible.

Henry Reed

We are living in very challenging times. Pressured in the workplace and stressed out at home, people are trying to make sense of their lives.      

Les Brown

Digitization is certainly challenging the old ways of doing things, whether that's in publishing or politics. But it's not the end. In many ways, it is just the beginning.     

Heather Brooke