I Got Rejected 19 Times. Here's How I Stopped It From Breaking Me

What to do when you get the "no," how to ask for feedback, and why you can't keep rejection to yourself

The email arrives. Or the phone rings. Your stomach drops before you even read the subject line or hear the tone.

“We’ve decided to move forward with another candidate.”

Getting rejected sucks. It really, really does.

And it is going to happen.

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The Simple Truth

Let me start with the simple truth.

The number of times that I have been so close that I could taste the offer, where every conversation felt like I was a shoo-in, where I replayed every interview in my head and couldn’t find a single mistake...it’s an insane amount of times.

Remember, over that year-and-a-half period when I was pivoting into retail, I was rejected 19 times after going through the full interview process from start to finish.

We’re not talking about just applying. That number is in the hundreds. I’m talking about multiple rounds, presentations, the whole thing. Nineteen “no’s.”

And out of those 19, for 16 of them, the feedback was the exact same thing, over and over again: “Honestly, you did nothing wrong. The only differentiating piece was the direct industry experience the other candidate had.”

Imagine hearing that. You did everything you could, and it still wasn’t enough.

It sucks.

So the first thing I want you to know is that the frustration you feel is real and it’s valid.

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Ask for Feedback

So, what do you do?

Here’s my advice.

First, when it’s appropriate, ask for feedback. Only do this if you’ve gotten to the final round. That’s when the hiring team has enough data to give you a real assessment.

And I prefer asking the hiring manager directly, not the recruiter, because they have the most specific insights.

If you get a rejection email, you can respond gracefully and ask. Something like this:

“Hi Mary,

I just got the news about the role. While I’m disappointed, I want to thank you and the team for taking the time to speak with me. I genuinely enjoyed learning about your vision.

As you know, I’m driven to break into the retail industry, and I would be incredibly grateful if you could share any specific areas where I could improve to be a stronger candidate in the future. Any feedback you can provide would be a huge help.

Best, Gerome.”

Sometimes they won’t respond, and that’s okay.

But if they do, and they give you tough feedback, do not argue. Don’t say, “But that’s not me!”

Just respond gracefully: “Thank you so much for that specific feedback, I really appreciate it. I’m definitely going to work on that. Best of luck to you and the team. I’ll be rooting for you!”

That’s it. You leave the door open.

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The Phone Call Rejection

Now, if you get a rejection phone call, it’s an even better opportunity.

After you listen, you can say this with enthusiasm:

“Ah, that’s not the call I was hoping for today, but I have to say, I really enjoyed all of my conversations, especially with Mary and Jack. I was so pumped about the idea of helping them with their digital strategy. I understand it’s an extremely competitive market, but I’m still driven to get a role just like this. On that note, could you provide any specific details on where I can improve for next time?”

That positivity makes a huge impression.

And it pays off.

The company I work for today, the role I’m in right now? I interviewed with this exact same team and got rejected a few months prior.

But I made sure not to burn any bridges. I learned, I came back stronger, and I got the job.

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The Mindset

Now, let’s talk about the mindset.

I’m not going to tell you getting rejected is easy. But you need to realize that 99% of the time, a rejection is out of your control.

It is not your fault.

You’ll drive yourself crazy rehashing interviews, thinking, “Why did I wear this shirt? Why did I cough? Why did I say X instead of Y?”

I did that for every rejection in the beginning.

The market today is flooded with incredible talent from great schools and great companies. Sometimes, it just comes down to a coin flip.

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Don’t Keep It to Yourself

And my final, most important tip: do not keep these rejections to yourself.

The more you hold it in, the worse it’s going to be for you mentally.

I learned that I forget about a rejection almost immediately as soon as I talk about it with my partner or a friend.

I’d just say, “Damn, remember that final round I had with Company A? Yeah, just got the rejection. Sucks. I really thought I had it, but they went with someone with direct experience. It is what it is.”

And after that, the next day, I had completely moved on.

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Your Task

Here’s your task for this post. It’s not a writing assignment.

First, I want you to truly internalize that rejection is part of the process, not a judgment of your worth.

Second, identify one person. A partner, a friend, a mentor. Someone you will commit to talking to about your next rejection.

Do not hold it in.

The beginning is going to suck. But the most important thing is to not give up. Ever. Don’t stop.

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In the next post, we’ll talk about the flip side: handling job offers and the basics of negotiation.

I’ll see you there.

Here is the complete career playbook (all 26 posts with real-world interview, resume, and career examples) for anyone who is pivoting roles, industries, about to graduate, stuck in their current path, not sure what to do next, etc.