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Hey There!

Welcome to Issue #185 of Jobseeking is Hard!

Today's issue is brought to you by Wispr Flow! If you're a free subscriber and value our content, it costs $0 to support us by clicking the ad and checking out the service. Show our sponsor some love for supporting Jobseeking is Hard! Thanks!

Happy Wednesday!

One of the more frustrating parts of modern hiring is that a lot of highly capable people struggle precisely because they’ve done too much. They’ve built broad careers, operated across multiple functions, solved different kinds of business problems, and developed experience that doesn’t fit neatly into one category. Then they sit down to write a resume and try to communicate all of it equally.

That’s usually where the problems start.

This week, I want to talk about why smart, accomplished professionals often write weak resumes, why broad experience becomes harder to position during tighter hiring markets, and why the hiring process tends to reward clarity more than complexity.

I’ll also walk through how direction and narrative clarity completely changed one Comprehensive Resume Review client’s job search. After restructuring the resume and simplifying the positioning, the client told me they’d scheduled more interviews in the previous week than they had in the last year, and later mentioned they’d never gotten a job so quickly.

And one quick reminder since graduation season is here! The limited-time New Grad Bundle is still available, and honestly, it’s probably one of the best gifts you can give the new grad in your life right now.

A lot of entry-level candidates struggle because they don’t know how to position internships, coursework, projects, leadership experience, or part-time work in a way that feels relevant to employers. The bundle is designed specifically to help with that transition from school to the job market.

It includes a resume built from the ground up, a tailored cover letter, and a LinkedIn profile rewrite to help new grads position themselves more effectively before they start applying. There’s also an optional strategy call for interview prep, job search questions, or general guidance entering the market. Check it out here!

This week we’re talking about:

• Why accomplished professionals struggle with positioning

• How direction changed a client’s job search

• The best (worst?) job posting of the week

And for Premium subscribers I’m:

• Debunking recruiter advice about messaging recruiters on LinkedIn

• Answering a Premium subscriber’s question about whether they should apply for jobs they seem overqualified for. I’ll explain why “overqualified” is often interpreted as a hiring risk, how recruiters evaluate senior candidates applying below their level, and why positioning and narrative clarity matter so much in those situations.

Let’s get to it!

CLARITY VS. COMPLEXITY

Most weak resumes aren’t written by weak candidates.

They’re usually written by smart, successful people who’ve built complicated careers and genuinely understand the full range of what they’re capable of doing. That’s often the problem.

Experienced professionals tend to resist narrowing their narrative because narrowing feels reductive. They know they can lead teams, improve operations, influence executives, manage clients, solve strategic problems, and operate across multiple functions. Many of them have spent years becoming more versatile, so when they sit down to write a resume, they try to preserve all of that complexity. They want the document to reflect the full picture of who they are professionally.

The result is often a resume that communicates intelligence and experience while making it surprisingly difficult for recruiters to understand where the person actually fits.

I see this constantly with senior candidates, consultants, operators, startup leaders, and people with broad cross-functional backgrounds. They’ll often say some version of: “But I have done all these things.” And they’re right. The problem usually isn’t accuracy...it's positioning.

The hiring process rewards clarity far more than completeness. Smart people understand nuance. They know business problems overlap. They know leadership rarely fits inside one clean category. They understand that strategy affects operations, operations affect revenue, revenue affects hiring, and hiring affects execution. Because they understand how interconnected their work really is, they write resumes that preserve complexity instead of reducing it.

The hiring system isn't designed to understand the most intellectually complete explanation of someone’s career. Instead, it rewards fast categorization. That’s the disconnect a lot of experienced candidates struggle with in this market.

Many experienced professionals are also trying to preserve optionality when writing resumes. They don’t want to be boxed into one path because they genuinely can do multiple things well. So the resume becomes an attempt to keep every possible door open simultaneously.

That usually creates the opposite effect. When every skill gets equal emphasis, the reader struggles to understand what the candidate wants most to be hired for. The document reads more like a list of strengths than a clear professional identity. Leadership, operations, transformation, consulting, execution, and strategy all compete equally for the candidate's attention because the candidate sees all of them as true and important.

And honestly, they usually are. The problem is that recruiters don’t evaluate resumes in the same layered way candidates experience their careers. Recruiters are usually trying to answer a much simpler question very quickly: “Where does this person fit?” If the answer isn’t obvious, the application becomes harder to process... especially with time constraints.

This is why broad backgrounds often struggle more during difficult hiring markets, even when the candidate is highly capable. In tighter markets, companies become more risk-averse and more specific about what they want. Hiring managers start looking for people who feel like obvious lateral fits, and recruiters become even less willing to interpret ambiguous positioning.

Remember, just because someone got an interview and you didn’t, that doesn’t automatically mean they’re more qualified than you are. Sometimes the person moving forward simply communicated a clearer story, or their background mapped more directly to the role. Their resume required less interpretation. Their experience felt easier to categorize quickly.

That’s frustrating for highly capable people because many of them are actually being penalized for the exact thing that made them successful professionally: breadth, adaptability, range, and the ability to operate across multiple environments. That doesn’t mean experienced professionals should undersell themselves or pretend their careers are simpler than they are. But it does mean resumes work better when they prioritize clarity over total representation.

A strong resume doesn’t try to communicate every possible thing someone can do. It focuses attention on the specific narrative most likely to get that person into the conversation they actually want.

Have a topic you want me to cover in an upcoming issue? Reply or email [email protected] and tell me what you want to know!

SHAMELESS PLUG

If your job search needs a little more help, Karpiak Consulting offers resume and LinkedIn services, as well as job search strategy coaching.

Who knows…maybe you’ll schedule more interviews in the past week than you have I the last year like this client 🤷‍♂️

So how did I help this Comprehensive Resume Review client gain so much traction, so quickly?

Direction.

Nothing about the background was weak. The issue was that the resume was trying to communicate too many things equally.

This client had a broad background with experience spanning multiple functions and leadership areas. Very smart. Very accomplished. But the resume was trying to communicate the full complexity of everything they’d done professionally, which made the positioning harder for recruiters to process quickly.

The review focused heavily on narrowing the narrative, improving clarity, explaining execution instead of just outcomes, and reducing ambiguity. A lot of accomplished professionals unintentionally create resumes that require interpretation instead of recognition. Recruiters are trying to quickly understand where someone fits.

After making the changes, the client told me they’d scheduled more interviews in the previous week than they had in the last year. Later, after accepting a new role, they mentioned they’d never gotten a job so quickly.

That’s why I spend so much time talking about positioning. A lot of highly capable people aren’t struggling because they lack experience. They’re struggling because their experience is being presented in a way that’s too broad, too layered, or too difficult to categorize.

If you’re feeling like your resume isn’t telling your story the way it should and don’t know how to frame your experience, our services can help. 

Curious what the process has been like for other clients? Check out our testimonials here!

BEST (WORST?) JOB POST

OF THE WEEK

Here’s the job post that got the most people talking on my Instagram this week!

“listed as ‘remote’ for visibility” is wild

If you come across an irritating job posting, email it to the newsletter or DM me on Instagram and I’ll add it to the list to post!

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PREMIUM SUBSCRIBER QUESTION

“Should I apply for jobs I’m overqualified for?”

Check out the Premium Section below for my answer! Not a Premium Subscriber? Upgrade here: www.JobseekingIsHard.com/upgrade

Why upgrade? For less than $0.63/day, you get:

• Subscriber-Only Discounts: Get exclusive promo codes for Karpiak Consulting services, available only to Premium subscribers. Whether you're updating your resume, need a LinkedIn profile review, or want expert help tailoring your applications, these occasional discounts make expert support more accessible.

• Extra Tips & Advice: Gain exclusive insights, strategies, and advice from a recruiter with over 20 years of experience in the field. Discover what hiring managers truly value and how to stand out at every step of your job search.

• Access to Previous Issues: Explore a library of knowledge with all 100+ past issues of the newsletter. Each edition is packed with proven strategies, practical advice, and real-world jobseeking stories to give you an edge in today’s competitive job market. From resume tips to handling tough interview questions, you’ll find answers to every challenge.

• Exclusive Q&A: Have questions about your job search? Premium subscribers can ask Adam directly! Questions will be featured in upcoming issues, with detailed answers tailored to real-world scenarios, ensuring you get the guidance you need.

• Bonus Content: As part of your Premium subscription, you’ll receive 20 additional job search tips delivered to your inbox over the next 20 days. This includes advice on avoiding common mistakes and maximizing your job search strategy to land interviews faster.

Jobseekers, have a great rest of your week, and good luck with those applications!

-Adam

PS!! If you're enjoying the newsletter, let people know! Forward it, post it on social, tag me, whatever...the bigger the discussion, the better! The idea is to help as many people as possible!

About Adam- Recognized as a leading voice on hiring and workplace trends, Adam has been recruiting and providing career advice since 2003, developing high-trust relationships based on honesty with companies and jobseekers. A highly sought-after speaker, he has appeared in numerous outlets, including Bloomberg News, Business Insider, LinkedIn, and CNNMoney. You can find out more about Adam's resume and coaching services here.

AFFILIATES

NOTE: As an affiliate to these services, we will receive compensation if you purchase products or services through the links provided.

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