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Grey’s Anatomy: Derek’s 5 Best Pieces Of Advice (& His 5 Worst)

The death of Grey’s Anatomy male lead character, Derek Shepherd, on season 11 was once thought of as the pitfall to this series’s downfall. But that wasn’t the case, as the show’s ratings kept strong to this day after 17 produced seasons.

10
Best: “If You Don’t Feel The Losses… That’s When You Know You’re Not Cut Out For This Kind Of Work.”

Derek was very empathetic with his patients and he would, oftentimes, respect their wishes/fears promptly even if there was hope to treat these people. He had a compassionate nature and viewers could see that patients would find comfort in Derek’s presence considering how caring he was. Even right before his death, Derek didn’t think twice about rescuing someone else. So when he shared this piece of advice, it pretty much summed up that a medical professional needs to have a calling to help others but also the humanity to grief the loss of human life.

9
Worst: “This Is How A Chief Does Things. Take Note.”

When Derek was Chief, he had moments where he was a jerk to Richard. While his talents as a surgeon were unquestionable, sometimes his arrogance and insufferable ego took the best of him when giving others advice. His words could actually come off as cold-hearted speeches more than pieces of wisdom.
Therefore, when he turned to his former Chief of Surgery and said the quote above, almost everyone agrees that, even though he was right, he was acting snobbish. Moreover, Derek had been the one who used Richard’s battle with alcoholism to take down his position as the chief. Hence, this advice sounds infuriating for most viewers.

8
Best: “Breakthroughs Don’t Happen Because Of The Medicine. Real Breakthroughs Happen Because Someone Is Scared To Death To Stop Trying.”

In yet another conversation with Dr. Webber, during season 7, there was a scene where Dr. Shepherd said this profound quote. Even though it was said in a time where he was feeling depressed after losing a pregnant patient, these words beautifully serve as a piece of advice for any physician who encounters challenges. It suggests that doctors should consistently thrive to find solutions to help heal their patients even if medicine doesn’t have all the answers. Derek went as far as leaving the hospital due to this heartbreaking loss but, eventually, he returned.

7
Worst: “It Wouldn’t Be Love If It Didn’t.”

Derek and Amelia were siblings but it’s no secret that, in his last season, he felt intimidated by his sister’s superior position. But when Amelia shared with him that she was falling in love with Owen Hunt and how afraid she was that it was going to destroy her, Derek replied with the quote above, most likely because of his own feelings for Meredith.

However, these words weren’t really good advice as they feel short of depth and meaning. It seems like a childish view of a love relationship, one where “love” is only a valid feeling if someone is afraid of losing their identity and strength because of that emotional connection to another.

6
Best: “Ask Most Surgeons Why They Became Surgeons And They Usually Tell You The Same Thing. The High, The Thrill Of The Cut. For Me, It Was The Quiet. Peace Isn’t A Permanent State. It Exists In Moments. Gone Before We Knew It Was There.”

Say what you will about some of his choices in life, but Derek had some amazing, profound thoughts about his profession – and the human condition. This quote is a great reminder of how people should search for more peaceful moments in their lives as his view on a surgery’s undisturbed setting was where he used to find his peace. He went on to add: “We can experience it at any time, in a stranger’s act of kindness or a task that requires complete focus. The trick is to know when they’re happening so that we can embrace them, live in them. And finally, let them go.”

5
Worst: “When It Hurts So Much You Can’t Breathe, That’s How You Survive. By Remembering That One Day, Somehow, Impossibly, You Won’t Feel This Way.”

This comment-turned-into-advice was actually a Derek and Izzie Stevens’ split quote. It easily reminds people of the classic saying: “this too shall pass,” even if it is said in a very dramatic way. Had it been said with a simple, wise approach it would have sounded much better. Suggesting that because you are experiencing the severest form of pain is the reason you survive seems a bit off-point. Surely, everyone’s pain is real and when it exists it can feel like a dark feeling that will impact forever. But this is usually not true nor it is “impossibly” going to disappear.

4
Best: “The Human Life Is Made Up Of Choices. Yes Or No. Live Or Die. Hero Or Coward. Fight Or Give In. I’ll Say It Again To Make Sure You Hear Me.”

And Derek continued, saying: “The human life is made up of choices. Live or die. That’s the important choice. And it’s not always in our hands.” This reflection came at the end of a life-threatening episode for him as he got shot by a mourning husband who was looking for vengeance for the loss of his wife – who had died at Seattle Grace Hospital. Derek almost died too but was able to be saved by Meredith and Yang, after choosing to “fight and not give in,” in a shocking event that “was not in his hands,” as he put it. A bit of profound advice on making choices to live more consciously and fight for what/who you want to have/be.

3
Worst: “He’s Happy With The Eyeball Doctor. So Make Sure You Want Him Because You Want Him And Not Because He’s With Someone Else.”

Derek’s friendship with Lexie did not start close but, through Meredith, things developed progressively. However, it was only during season 8 that these two started confiding things to each other – especially because of her on-and-off relationship with his best friend, Mark Sloan. Eventually, Derek grew into the big brother role towards her giving brilliant advice both personally and professionally. However, the quote above was not one of those moments. It just feels shallow and unsubstantial when compared to other suggestions he made in the past.

2
Best: “The Only Skills You Can Count On Are Your Own. Until One Day, You Leave The Classroom And Step Into The O.R. You’re Surrounded By A Team That You Have To Rely On Whether You Trust Them Or Not.”

A world-class surgeon, Derek was power-hungry and one of the most ambitious characters on the show. On one occasion, he performed an unauthorized-high risk surgery and dared to dismiss Richard when the Chief fired him. Nonetheless, some of his advice was really good like the quote above. Any new surgeon stepping into the OR needed to understand that once they were in there, it was not about what they could do anymore. It’s about what a team could deliver together.
1
Worst: “You Don’t Have To Do Everything I Do.”

Fans know that Mark earned the title of Derek’s “best friend,” even if their relationship had been rocky at times. And the audience got used to seeing Mark as a “womanizer.” But as this character grew, so did his plans for his love life. When Lexie Grey showed up, there was a phase where he looked like he was trying to mirror Shepherd’s behaviors towards Meredith. That’s when Derek advised him not to move in with little Grey yet, proceeding with the quote above. Of course, Mark reacted negatively as this was not the best way to put things… But not surprisingly, these words were totally “Derek’s self-centered style”.

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