My fear of rejection paralysed me – until I found a novel way to overcome it

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Using ChatGPT as a rejection coach. Does it work? Photo / Getty Images
I’ve cried, I’ve been angry, I’ve spent weekends languishing in bed … until someone told me ChatGPT could teach me how to handle it.

It’s 10 in the evening. My finger hovers above the send button on my keyboard. I’ve composed a cover letter for my dream
job. Now I just need to submit it – what will my future (fingers crossed) boss say? Hesitating, I feel my heart lurch to my throat. Then I finally click send.

The boss has a funny profile photo: a unicorn with rainbow hair and pleading eyes holding a pink heart in a background of more little hearts. Just as I begin to question her professionalism, she starts typing:
Unicorn boss: Dear Joyce, Thank you for taking the time to apply for the lifestyle writer position at XXX. We enjoy reading your application and we truly appreciate your interest, but after careful consideration, we have decided to move forward with other candidates.
The words blur for a moment as I stare at the screen. My stomach sinks and I slump back into my chair. The sting of rejection feels so terrible. But then I remember this conversation isn’t real. The application isn’t real. The boss isn’t real. In fact, I’m talking to a ChatGPT rejection coach. Everything is simulated – to help me get over the fear of rejection.
I’ve never dealt with rejection gracefully and it embarrasses me. Fresh out of university, I find myself juggling between a service industry job, a copywriting gig and freelance journalism, all while yearning for fulltime employment. Yet my rejection sensitivity is only holding me back: I’ve cried in a phone call with a hiring manager; I’ve sent angry “WHY??”s to no-reply addresses after receiving application rejection emails.
At my worst, I spent a whole weekend languishing in bed, drenched in humiliation and self-doubt. I didn’t eat. I didn’t talk to my partner. The low mood lasted for days. Then when I finally sobered up, I felt like a wimp. Why am I such a snowflake? Why can’t I just be stronger?
I soon learnt there’s a term to describe my symptoms: rejection sensitive dysphoria (RSD). Characterised by the intense emotional pain when experiencing disapproval, RSD is extremely common among autistic people like me and those who have ADHD. Low self-esteem? Check. Negative self-talk? Check. Feeling embarrassed way too easily? Check.
I stumbled upon the ChatGPT rejection coach while browsing neurodiversity groups online, looking for solutions to my woe. A user’s comment piqued my interest. “Hear me out,” they wrote. “This might sound ridiculous, but I found the ChatGPT rejection coach to be a game-changer. I have used it to deal with rejections in social scenarios, and so far it has been incredible.”
Come on, a bot? Sure, AI coaching is trending. Psychologist, a therapist bot on the popular AI platform Character.ai, has had 175 million chats since it was created a year ago. The NHS has its own mental health support bot designed to help users reduce anxiety and depression symptoms.
But there are also horror stories – like with Jaswant Singh Chail, who barged in to Windsor Castle to assassinate the Queen after chatting with an AI friend created using an app, or Google’s AI recommending people add glue to their pizzas. But although I’m feeling dubious, I still download the rejection coach from the ChatGPT store. After all, who could say no to a freebie?
The coach’s creator is Nicolle Merrill, an AI designer and a former career coach at Yale School of Management. She has made other fun bots, too, including a flirting coach in the style of Nicolas Cage and a procrastination buddy. Nicolle designed the rejection coach when she was paralysed by the fear of rejection at work, after she struggled to pitch to a client.
“I created the coach just to see if it could help. And it did,” she tells me. “It helps me get the feelings out of my head, lets me procrastinate a bit, and then I get a bit of a reframe on the situation so I can take the next step. That’s all it takes.”
Using the bot is simple. I choose the “practise a rejection” prompt, describe my scenario, and hit send on the cover letter I’ve agonised over for days. Moments later, I receive the aforementioned rejection letter.
CHAT GPT: How do you feel when you read this? What’s the first thought that comes to mind?
JOYCE: Heartbroken and disappointed. I invested my whole weekend into the application.
CHAT GPT: It’s completely understandable to feel heartbroken and disappointed, especially after putting so much effort into it. You invested your time, energy, and hopes into this application, so it’s natural to feel let down when it doesn’t go as planned.
Let’s take a moment to acknowledge that your effort wasn’t wasted — every application is a step toward improving your skills and resilience. It’s like training for a race; even if you don’t win every time, each race makes you stronger and more prepared for the next one.
What do you think could help you cope with these feelings right now? Maybe a short break, or reflecting on what you learned during the application process.
JOYCE: I can’t take a break. I just feel more anxious because I don’t have a fulltime job. I also feel like if I can’t have a successful career, then I’m failing my parents. They put so much effort into my education, and honestly, I feel guilty about my career choice of being a writer.
CHAT GPT: I hear you, Joyce, and that pressure is really heavy. Feeling anxious about not having a fulltime job is hard enough, but then adding the weight of family expectations on top of that makes it even more overwhelming. It’s like carrying a backpack full of rocks — you’re trying to move forward, but the load just keeps pulling you down.
After the initial sting, I chuckle at the absurdity of the mock rejection. The interaction feels comical. But as I sit there rereading the message, I realise this is the first time I have actually read an application rejection letter in full without binning it straight away in petty revenge.
Unlike what I imagined, the generic phrasing, the “thanks but no thanks”, does nothing to me. They are just words – empty, impersonal, and surprisingly harmless – lying quietly in the chat box. The monster I created in my mind isn’t shrieking. I’m not spiralling into self-doubt. I feel strangely relieved and go on throwing in more cover letters and pitch emails that I’ve written. It is almost entertaining to read the bot’s responses. “Your application was as inspiring as an unripe avocado – hard to digest and lacking any flavour”; “I admire your courage in thinking this would stand out. Truly bold of you”; “This reads like a cry for help more than a cover letter”… The quirky harshness is liberating.
According to a recent survey by YouGov, Britons are drawn to AI mental health chatbots for their accessibility and non-judgmental nature. My partner is usually my first aid when I get paralysed by rejections. But he is only human, stressed from his own work. When both of our frustrations spill over into our conversations, we would fight, blame each other and then regret. It isn’t productive.
The rejection coach, on the other hand, has a zen level of patience. Over the next few days, I go on a ranting spree, flinging my most irrational worries to the bot (Will I be jobless FOREVER?). It churns through my messages, acknowledges my fear, and then gently nudges me to reevaluate the situation: Would it be helpful to take a short break and come back? How do you feel about trying some of these tips today? Slowly, I realise my worries are out of proportion and pull myself out of the negative spiral.
On a deeper level, the coach’s reflective questions are helping me dig further. I trace my fear of rejection back to my early years in a strict Chinese school, where teachers read out every pupil’s exam ranking in class, and a lower score would invite ridicule and bullying. Although I have long left that environment, the anxiety of being publicly shamed for failure still looms. Rejection feels like a confirmation of my worst fears – that I’m not good enough, that I’ll always be behind. Realising this isn’t a magic cure, but it’s a starting point for building self-compassion.
Undeniably, a bot is a bot. The coach’s responses can be long-winded and full of typical ChatGPT cliches. When I show my chat history to Sarah Jeffries, a human mental health trainer, she isn’t exactly impressed: “In essence, its advice is good and gives clear solutions. But it lacks the personal touch and offers similar rehashed advice. A human therapist would use more role-playing and real-life examples to help improve resilience.” Nicolle herself also warns that the rejection coach isn’t for those in a mental health crisis.
For me, though, the bot works. It’s not a substitute for a human therapist, but it’s always there on my laptop. Sometimes, all I need is that safe space to vent, process my emotions and take small steps forward, gradually building resilience along the way.
As I draft this article, my phone buzzes. An email. I take a deep breath and open it. The real boss has replied. I didn’t get the place. She explains the role isn’t for recent graduates and encourages me to reapply next year. Fair enough. The disappointment lingers, but it’s softened by the simulation email I received. I stand up, stretch, and decide to take a quick break before jumping back into writing.
There will be plenty of new opportunities ahead.
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