How to Ditch Your Pain Letter for an Opportunity Letter

Career advice from Liz Ryan tells you that writing a pain letter to accompany your resume will get you an interview 25% of the time. But that’s a 75% failure rate. Ouch!

While 1 out of 4 isn’t bad, you can beat more of your competition by writing an opportunity letter instead.

First, What is a Pain Letter?

Liz’s counsel is to research and develop a hypothesis about a problem your target hiring manager might have. Then, you find the hiring manager and send them a letter explaining how you’ve solved that problem in the past.

Do Pain Letters Work?

As I mentioned above, Liz says they work about 25% of the time. However, I recruited for 28 years, received many pain letters, and round-filed or deleted every one of them.

Here’s Why Your Pain Letter Fails

A few years ago, Josh Goldstein, currently Co-Founder at, found his job search had stalled. He was so frustrated he wrote a blog post asking his readers for help.

In the post, he shared a letter he had sent to a target employer,, where he described his perceptions of their growing pains and ideas about solutions to their problems.

The blog post gained the attention of foursquare’s Head of Talent. Here’s his feedback on what Josh wrote:

“Listing ideas in a cover letter can be dangerous. As an outsider, it’s tough to know the exact vision and strategy of the company. If you are 100% sure you’ve nailed it, then the job is yours.

But if your ideas go slightly in the wrong, wacky direction, it could do more harm, and the company might think you don’t get it.”

So, while a pain letter might pull your resume out of the black hole 25% of the time, it probably won’t warm your reader’s heart.

How would you feel about receiving a letter from an uninformed stranger that suggests you don’t know what you’re doing?


The Opportunity Letter

Rather than risking sounding like a pompous jerk, let prospective employers know you can capitalize on opportunities. That makes an excellent first impression.

What if foursquare’s Head of Talent had received this “not pain” letter?

Sample Opportunity Cover Letter

Dear Jason,

I’m writing to express interest in your Media Partnerships role. I’m about to finish my MBA at UNC’s Kenan-Flagler Business School and want to join a company where I can deliver growth.

By way of example:

I worked for a nonprofit before business school. One day, a sports celebrity mentioned our organization in a national publication. We became aware of his endorsement when checks started arriving at our door in mailbags.

I saw the opportunity to develop a long-term partnership with him and pitched my idea to our COO. Together, we wrote him a thank you letter and had our CEO and Board Chair sign it.

Beyond thanking him, we asked him to consider an ongoing relationship with our organization. We outlined our vision of how that would help the people we both wanted to benefit.

In brief, our outreach turned into a branded program that continues to raise more than $5 million per year for my former employer and its grantees. I managed that relationship and program until I left for business school.

I can imagine some of the growth challenges that foursquare might be facing, but I’m not exactly sure what they are.

Here’s what I do know:

If you set me on a mission, I can develop a set of ideas, work under my manager’s direction to vet them, and execute what we decide. I’ve done it before. I will do it again.

Let’s have coffee or get together on Zoom. I want to meet you so I can learn more about foursquare’s needs and so you can learn more about me.


Josh Goldstein
Attachment: Resume

Checking foursquare’s Boxes

Beyond describing the risks of making assumptions in a pain letter about an employer’s biggest problems, foursquare’s Head of Talent counseled Josh to talk about:

  1. Why he’s the perfect fit for the role.
  2. What he brings to the table.
  3. Why Business Development (the job Josh wanted) is the right home for him.

The sample opportunity letter above gives the reader answers to each question. Plus, it’s factual, not hypothetical.

Who would you rather interview — the person who proves they can see and deliver on opportunities or the one who misses your pain point and annoys you?

Keep It Real

Writing a compelling pain letter is a roll of the dice because you often have to imagine the hiring manager’s problems.

Cover letters and resumes are tough enough. Don’t challenge yourself further to create a pain hypothesis.

Just write about reality and top it off with a straightforward call to action like coffee or a Zoom meeting. You’ll create a more powerful impression.

What Happened to Josh?

The blog post got Josh an interview with foursquare, but not the job.

He joined another start-up and then became a Co-Founder at (not an affiliate). The company lets top talent apply for jobs with promising start-ups in 60 seconds and gives start-ups access to that talent for a monthly fee.

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Featured by: Fast Company
Image: pressmaster
Updated January 2022

© 2015 – 2024, Donna Svei. All rights reserved.

Comments 4

  1. Hi, I’ve been doing my job searches and finding it difficult to find work. I’m well into my 50’s and it seems the younger get hired over the mature and experienced, how can we be “The Chosen One” ?

  2. Hi Susanne,

    I like the AARP (Kerry Hannon), Career Pivot (Marc Miller), and (Susan Joyce) sites for career advice that’s specific to people who are over 50. You’ll also find Phyllis Mufson’s Twitter feed features good 50+ information.

    Best regards,


  3. I am changing careers, out of the restaurant field into an office environment. I’ve have done many job searches and I am still unable find the right job. How can I get my resume to stand out? To get someone to hire me with not a lot of experience?

  4. Hi Dawn,

    I would start by checking to see if you’re hitting enough keywords in the job postings.

    Also, as mentioned above, be sure that you portray your initiative!

    Best wishes!


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