Pain Letter

Your Cover Letter — Write an Opportunity Letter, Not a Pain 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. That’s a 75% failure rate. Ouch!

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

Here’s Why Your Pain Letter Fails

First, let’s talk about why pain letters fail 75% of the time.

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

Josh shared the letter he had sent to He wanted a Business Development role. In the letter, he gave his solutions to his perception of foursquare’s growing pains.

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 won’t get you an interview if you come off as a know-it-all who doesn’t get it.

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 risk sounding like a pompous jerk, instead let prospective employers know you can capitalize on opportunities. That makes a good first impression.

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

Sample Opportunity Cover Letter

Dear Jason,

I’m writing to express my 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 my energy, creativity, and proven ability to develop relationships can deliver growth.

By way of example:

I worked for a nonprofit before I started business school. One day, a sports celebrity mentioned our organization in a huge 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 the Chairman of our Board 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.

Long story short, our outreach evolved into a branded program that continues to raise over five million dollars each year for my former employer and its grantees. I managed that relationship and the program until I left for business school.

I can imagine some of the growth challenges that foursquare might be facing, but I’m not sure exactly 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 on what we decide. I’ve done it before. I will do it again.

Let’s have coffee or get together on Skype. I want to meet you so I can learn more about foursquare’s needs, and 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 is the right home for him.

The sample opportunity letter above, and its story about the writer’s business development success, shows the reader (rather than telling) the answers to each of those questions. It’s factual, not hypothetical.

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

Keep It Real

It’s a roll of the dice to write a compelling pain letter because you often have to imagine the hiring manager’s pain. 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 an easy call to action like coffee or a Skype meeting. You’ll create a more powerful impression.

What Happened to Josh?

Josh reports that his blog post got him an interview with foursquare, but not the job.

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

Featured by: Fast Company and SmartBrief on Your Career.
Image Courtesy of Kelly Brito
Updated May 2019

© 2015 – 2019, Donna Svei. All rights reserved.

Comments 3

  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?

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