#1: Why High Achievers Struggle With Disappointment (And What to Do About It)
51 degrees.
10 weeks out from my knee surgery, I am only able to bend my knee 51 degrees when it should be 90.
I thought I'd be playing golf by now—instead, I'm scheduling my second surgery. Due to a buildup of scar tissue, I will need to have arthroscopic lysis of adhesions and closed manipulation.
Translation: general anesthesia, a ⅜ inch incision, remove the excess scar tissue with an arthroscopic cutting device, and then manually bend my knee to 90 degrees. Fun-wow.
My initial reaction was one of shock, anger, sadness, confusion, disappointment, and a profound sense of hopelessness.
Since then, I’ve accepted it, found a new physical therapist, and moved on. But I’m still not happy about it.
When was the last time you got news that made you want to punch a wall?
Initially, after hearing the news of a second surgery, that’s how I felt—angry, sad, devastated, and hopeless. My honest fear was What if my leg never fully heals?
But here's what I’ve learned about handling life's curveballs. Someone really needs to hear this.
Why High Achievers Struggle Most with Disappointment
It can be tough to work through bad news—especially for high achievers who value progress and productivity. We are often hardest on ourselves, and it’s easy to get stuck there if you're always measuring forward rather than backward. One thing we rarely do is allow ourselves time to grieve and process disappointments.
The grief process isn't just for death—it applies to every loss, including business failures, missed promotions, health setbacks, and relationship disappointments.
In the face of my disappointing news, I took 24 hours to mope, grieve, express my anger, and then move to acceptance. With less consequential setbacks, decide how long you need to grieve (sometimes you may not know, but you can always add time if need be), and then move on.
Here's what most leaders miss: Before acceptance comes an acknowledgment of pain and loss. Professor Terry Wardle wisely said, "Life is a series of ungrieved losses. Every loss in life demands an appropriate season of grieving. Loss is meant to be grieved, and when we fail to grieve losses, that loss internalizes."
Without taking time to grieve, you will be tempted to keep going back there because you didn’t properly grieve it in the first place.
But grieving isn’t just a solitary act; it involves other people. Professor Wardle goes on to say,
“Grieving loss begins with finding a safe environment with people who are non-condemning, empathetic, who are confidential, and who finally give you the permission to say what’s inside and say it like it is.”
In my case, that happened with my family, a few close friends, and my counselor.
Who are your safe people when disappointment hits?
The Hidden Cost of Staying Stuck
Staying too long in your grief can also be damaging, leading to bitterness, cynicism, and perpetual disappointment—the leadership killers that destroy confidence, teams, and marriages.
But how do you know when it’s time to move on?
With less consequential things, it’s usually a choice, but the greater the grief, the longer the process, especially when it involves other people.
You'll know you've processed it properly when you can talk about the disappointment without your chest tightening, when you can make decisions about your future without that loss controlling your choices.
No, I’m still not happy about it, but taking time to grieve has helped me accept my second surgery and move on.
Since it can’t be changed, my only choice is to face it head-on and prepare mentally and physically.
Your REST Check
Most high achievers simply push through disappointment and get back to work, but the truth is that unprocessed grief can become internalized bitterness, which will ultimately sabotage your life and leadership.
If you skip the grieving process, you'll carry that disappointment into every relationship, every future decision, every team meeting, every strategic planning session.
But if you give yourself permission to properly grieve, you'll develop emotional resilience. You'll make decisions from wisdom, not fear. You'll become the leader who helps others navigate their setbacks because you've learned to move through your own.
Properly processing your grief determines whether setbacks will make you bitter or better.
This week's Rhythm of REST: When disappointment hits, give yourself a specific timeframe to feel it fully before moving to acceptance. Twenty-four hours for smaller setbacks, longer for major losses. Find your safe people. Process it properly.
What's one disappointment you've been "powering through" that actually needs to be grieved?
Until next time,
Kent
PS - I know I didn’t finish telling you Brandon’s story, but I felt someone needed to hear this. Next time, I’ll share more about Brandon and what Rhythms of
REST actually means.
Whenever you’re ready, there are three ways I can help you…
- Transform those anxiety-filled, rushed mornings into your foundation for daily success with myWin the Morning, Win the Day! Minicourse
- Schedule a Discovery Call to find out if executive coaching is for you - for business owners or executives
- Catalyze your organization - invite me to do akeynote or workshop
Sources
How the Five Stages of Grief Can Help Process a Loss, Very Well Mind
5 Stages of Grief: How to Cope with Loss, West Georgia Wellness Center
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