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Welcome to Issue #206 of Jobseeking is Hard!

Happy Wednesday!

It’s time for the Jobseeking is Hard Mailbag!

The newsletter’s mailbox is packed, so I figured now was a good time to answer some of your questions.

This week, I’m digging into questions readers have sent me about resumes, LinkedIn, interviewing, and the job search in general. Considering a lot of these are also questions that come up pretty regularly when I’m working with clients, I figured a lot of you are probably dealing with the same things, so this was a good opportunity to address them for everyone.

Let’s get to it!

“I keep changing my resume for every job I apply to, and I’m starting to feel like I’m rewriting the entire thing every time. How much tailoring should I actually be doing?”

You shouldn’t be rewriting your entire resume for every application.

When I’m working on resumes, I want the document to already have a pretty clear idea of what kind of job it’s targeting. If you’re applying to 5 different versions of roughly the same kind of role, most of the resume should continue to work as-is. You might modify the focus of your summary, move a particularly relevant accomplishment higher, adjust some language to better match how the company describes the work, or emphasize something that’s unusually important for that specific opening. But you shouldn’t need to rebuild the document every time you find a job posting.

If you do, I’d look at the jobs you’re applying to. Sometimes people think they have a resume problem when they’re actually applying to a pretty wide range of roles. If one application requires you to emphasize operations, another requires strategy, another requires sales, and another requires project management, there may not be one version of the resume that makes you look like an obvious fit for all of them.

This comes up in my resume work pretty regularly. I’m not trying to create a document that can technically be used for every job someone could possibly apply to. That wouldn’t be effective. I want the positioning to make sense for the jobs they’re most likely to pursue. Then tailoring becomes adjusting the emphasis instead of starting over.

It’s about due diligence, not rebuilding. So yes, tailor your resume. Just don’t confuse tailoring with rewriting.

“I found a job I really want, but it’s been posted for a few weeks. Is it too late to apply?”

If the job is still posted, I’d apply.

Earlier is obviously better, but I wouldn’t assume a job that’s been posted for two or three weeks is already a lost cause. Especially right now, recruiters can spend a lot of time digging out from under applications. AI has made it incredibly easy to find jobs, tailor resumes, and apply at scale. A posting may have 500 applicants, but that doesn’t mean the recruiter has 500 qualified candidates. They may still be trying to find the 15 people who actually make sense.

A few weeks in, they may still be reviewing applicants, the first round of interviews may not have produced anyone, or the hiring manager may have changed what they’re looking for. You don’t know from the posting date alone.

Do the appropriate tailoring, submit the application, and then do the backchannel work.

This is something I talk about in coaching because applying shouldn’t be the end of your process for a role. See who you know at the company or who can make an introduction. Look for clues in the posting about who the role reports to, then use LinkedIn to identify the likely hiring manager or another important stakeholder.

You’re looking to influence, not introduce yourself. Send a short message explaining that you applied, why your background lines up with what they need, and give a specific example of solving a similar problem. And explain why you want this job with this company. “I applied!” isn’t much of a reason for someone to pay attention.

This can be particularly useful on an older posting. If the recruiter is staring at a giant applicant queue full of people who aren’t remotely qualified, a relevant candidate making themselves easier to find can be helpful.

There’s no guarantee they’ll respond, and you don’t need to message six people at the company. But if the job is still open and you’re a strong fit, apply. Then give them a reason to find you.

“Should my LinkedIn profile mirror my resume?”

No. They should be consistent, but your LinkedIn shouldn’t just be a copy of your resume.

When I’m working on LinkedIn profiles, I’m using the resume as a source because the basic facts obviously need to line up. Your titles, employers, dates, and overall career story shouldn’t leave someone wondering whether they’re looking at two different people. But copying and pasting your resume into LinkedIn misses a lot of what LinkedIn can actually do.

Your resume is usually being read in the context of a specific application. The recruiter already knows what job you want because you applied to it. LinkedIn doesn’t have that advantage. Someone might find you in a search, click on your profile after you applied, see you comment on a post, or get your name from someone else. Your profile needs to give them enough context to understand where you fit without a job posting sitting next to it.

That’s why I tend to use the headline and About section differently. You have more room to explain what you do, the areas you specialize in, and the kind of work you want to be associated with. You can also include relevant keywords throughout the profile because recruiters are actually searching LinkedIn for them.

The Experience section doesn’t need every bullet from your resume either. I’d rather use it to give someone enough information to understand the scope of your roles and highlight the experience you most want to be found for.

Your resume and LinkedIn should support the same career story. They just have different jobs to do.

3 PREMIUM SUBSCRIBER QUESTIONS!

“I use ChatGPT on my resume, so I know it’s always optimized for each job posting. What else can I do?”

“I’m applying to jobs I know I can do, but I don’t meet every requirement. How do I decide when it’s still worth applying?”

“I’ve been unemployed for a while. At what point does the gap itself start hurting me, and what should I be doing about it?”

Check out the Premium Section below for my answers! 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.

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That’s it for this week’s mailbag. Hopefully there was something in here that helps with your own search.

One of the reasons I like answering these questions is that the specifics may be different, but the same issues come up over and over again when I’m working with clients. People are trying to figure out how much to tailor, whether they’re too late to apply, what to do beyond submitting an application, and how all the different pieces of their job search should work together.

Keep sending me your questions! The mailbox will fill up again soon enough, and we’ll do another one of these.

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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Hey There!

Welcome to Issue #188 of Jobseeking is Hard!

Today's issue is brought to you by The Rundown AI! 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 common sources of frustration in the job search is that candidates and hiring teams are often focused on completely different things. Jobseekers naturally focus on qualifications and whether they meet the requirements listed in a job posting. Hiring teams are usually focused on whether someone appears capable of solving the problem that justified opening the role in the first place.

That disconnect creates a lot of confusion during the hiring process.

This week, I want to talk about why job descriptions are often descriptions of business problems and how interpreting them differently can change the way you position yourself.

I'll also share how one Comprehensive Resume Review client discovered that having another set of eyes on their resume was extremely helpful because recruiters weren't necessarily interpreting their experience the way they assumed they would.

This week we’re talking about:

• How reading job descriptions differently can change your entire job search

• Why recruiter interpretation influences resume effectiveness

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

And for Premium subscribers I’m:

• Debunking LinkedIn advice that says candidates should respond to every recruiter message

• Answering a Premium subscriber’s question about how to position a career that spans multiple functions and specialties. I’ll explain how to identify the story hiring teams are most likely to hire you for.

Let’s get to it!

YOU'RE READING JOB DESCRIPTIONS BACKWARDS

One of the most common mistakes I see during coaching calls happens before someone ever updates a resume, rewrites a LinkedIn profile, or submits an application.

It starts with how they're reading the job posting.

Most jobseekers approach a job description like a checklist. They scan the qualifications, compare them against their own experience, and start calculating fit. They look at years of experience, software requirements, certifications, industry exposure, and responsibilities. Then they try to determine whether they meet enough of the requirements to justify applying.

It's a reasonable approach, but it assumes the job posting exists primarily to describe the candidate the company wants.

Most of the time, that's not really what it's doing.

Companies don't create roles because they enjoy hiring people. They create roles because something needs attention. Revenue isn't growing the way they want. Projects are slipping. Customers are frustrated. Managers are overloaded. Teams are scaling faster than existing leadership structures can support. Technology has changed. Processes have broken. Someone left and created a gap that suddenly became impossible to ignore.

The job posting is simply the company's attempt to describe the type of person they believe can solve those problems.

Unfortunately, by the time that business need gets translated into a formal job description, the original problem reads like a wall of qualifications and responsibilities.

A company struggling with inconsistent customer onboarding doesn't write, "We need someone to fix our onboarding process." They write, "Seeking a customer success leader with implementation experience."

A company dealing with rapid growth and organizational growing pains doesn't write, "Our managers are overwhelmed and we're worried about retaining people." They write, "Looking for a people leader with change management expertise."

A company struggling to get alignment across departments doesn't write, "Nobody can agree on priorities." They write, "Must possess exceptional stakeholder management skills."

The qualifications are clues, and that distinction changes how you evaluate opportunities and how you position yourself for them.

One of the reasons job searches become so frustrating is that candidates spend most of their energy comparing themselves to the qualifications while hiring teams are focused on something else entirely. Hiring managers aren't usually trying to identify the most qualified person in an abstract sense. They're trying to identify the person they believe is most likely to solve the problem that justified opening the role in the first place.

That's why candidates with nearly identical backgrounds can experience very different outcomes. One candidate presents a collection of skills. The other presents evidence that they've solved similar problems before. One talks about stakeholder management. The other explains how they aligned competing priorities across multiple teams to move a stalled initiative forward. One talks about leadership. The other explains how they inherited an underperforming team and improved retention, productivity, or engagement.

The underlying experience may be exactly the same. The difference is that one candidate is describing qualifications while the other is describing solutions.

Once you start reading job descriptions through that lens, a lot of hiring behavior starts making more sense. You stop asking whether you meet every requirement and start asking whether you've solved similar problems. And you begin to realize that the strongest applications aren't focused around showing you “have skills.” They're built around demonstrating that you've already used those skills to address the kinds of challenges the employer is facing today.

Have a topic you want me to cover in an upcoming issue? Reply or email contact@jobseekingishard.com 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 having another set of eyes on your resume will be extremely helpful like this client found 🤷‍♂️

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So how did I help this Comprehensive Resume Review client improve their resume?

Interpretation.

The theme in this week's newsletter is that candidates often misunderstand what companies are actually telling them through job descriptions. They see qualifications. Hiring teams see problems. The same thing happens with resumes.

Most candidates read their resumes through the lens of everything they know about their careers. They know why projects mattered. They know why accomplishments were important. They know the context behind the work. But…recruiters don't.

This client’s challenge was that some of the most valuable parts of the background required interpretation from the reader. Leadership, ownership, coaching, growth, and strategy were all present, but there were places where the resume assumed the reader would automatically understand the significance of those experiences.

Focus on seeing the resume through the eyes of someone who has never met you before. Where was context missing? Where was impact understated? Where was the resume asking the reader to connect dots that should have already been connected?

That's often where the biggest improvements come from.

If you’re feeling like your resume isn’t telling your story the way it should and don’t know what context is missing based on your goals, 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!

unfortunately my labor activates on payroll-based benchmarks

Instagram post

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!

Today's issue is also brought to you by Oyster! C’mon give it a click…it costs $0 and helps support your favorite job search newsletter 🙂

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PREMIUM SUBSCRIBER QUESTION

"How do I figure out what story my resume should tell when my experience spans multiple areas?"

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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$35.40 per month, for 3 consecutive months (regularly $59 per month)

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Make this the start of something new for your career. Build in-demand skills, discover new career paths, and earn multiple job-ready certificates through expert-led instruction from leaders at Google, IBM, and more at a special low price.

Sign up here!

https://imp.i384100.net/c/4709194/2979777/14726

BETTERHELP: 15% OFF YOUR FIRST MONTH OF ONLINE THERAPY

Mental health is a massive part of your career. Anxiety, depression, self-worth issues…all become more intense the longer a job search goes on. With my link, get 15% off your first month of online therapy with BetterHelp!

​http://www.betterhelp.com/jobseekingishard

PREMIUM SECTION

Hey all! Thanks for being a Premium member! I hope you find the additional info helpful as you navigate your job search.

DEBUNKING CAREER CLICKBAIT

Technically this is the Career Clickbait section, but calling this clickbait feels a little unfair. Clickbait is usually trying to get your attention. This feels more like rage bait.

A recruiter recently posted that candidates should always respond to recruiter outreach because LinkedIn InMails cost recruiters money. According to the post, ignoring recruiter messages not only costs recruiters credits, but may also damage relationships that candidates might need later in their careers.

There are a few problems with this.

First, jobseekers are not responsible for managing recruiter budgets. Recruiters pay for sourcing tools because sourcing is part of recruiting. Sales teams pay for CRM software. Marketing teams pay for advertising. Recruiters pay for sourcing platforms. That's simply part of the cost of doing business.

Second, not every recruiter message deserves a response. Anyone who's spent time on LinkedIn has received outreach for jobs they're wildly unqualified for, dramatically overqualified for, located thousands of miles away, or completely unrelated to their background. Expecting candidates to respond to every unsolicited message because it might save someone a credit misunderstands how communication works.

The relationship argument is even weaker. A recruiter who damages a future relationship because someone didn't reply to a cold message probably wasn't much of a relationship to begin with. Professional relationships are built through meaningful interactions, not mandatory courtesy responses to unsolicited outreach.

Now, if a recruiter reaches out with a relevant opportunity and you know you're not interested, a quick response is certainly a nice thing to do. I've done it. Most professionals have. But there's a difference between professional courtesy and professional obligation. Jobseekers have enough things to worry about without feeling guilty about someone else's InMail credits.

Watch or read a questionable piece of career content? Send it along and I’d love to debunk it! contact@jobseekingishard.com

PREMIUM SUBSCRIBER QUESTION

"How do I figure out what story my resume should tell when my experience spans multiple areas?"

This is one of the most common positioning problems I see with experienced professionals, especially in technical fields. The first mistake people make is assuming they need to figure out exactly what they are.

Am I a systems engineer?

Am I an infrastructure engineer?

Am I a platform engineer?

Am I a cloud engineer?

Am I an architect?

Am I a technical leader?

The problem is that many successful careers don't fit neatly into a single category. The more experience someone accumulates, the more likely they are to work across multiple functions, technologies, teams, and business problems. That's especially true in technology, operations, consulting, and leadership roles where responsibilities naturally expand over time.

When candidates get stuck, they're usually trying to answer the wrong question. The goal isn't to discover the one perfect label that describes your entire career. The goal should be to figure out what hiring teams are most likely to hire you for. Those are very different concepts.

One of the things I see constantly during resume reviews is candidates trying to preserve every aspect of their professional identity at the same time. They want the resume to communicate the full complexity of what they've done because all of it feels important and all of it is true. Unfortunately, hiring teams aren't trying to understand your complete professional identity. They're trying to understand where you fit relative to the role they're filling.

That's why I often encourage candidates to stop asking, "What am I?" and start asking, "What is the strongest proof-of-concept story in my background for this role?”

For example, someone may have experience in infrastructure, cloud platforms, distributed systems, automation, software engineering, and technical leadership. All of those things may be true. But if the majority of their recent success came from building and operating large-scale infrastructure, that's probably the story that deserves the most attention. The other experiences still matter, but they become supporting evidence rather than competing narratives.

One of the easiest ways to figure this out is to look for patterns.

What kinds of roles generate interviews most consistently?

What problems have organizations repeatedly trusted you to solve?

What responsibilities keep showing up throughout your career regardless of title?

What would your former managers be most likely to hire you to do again?

Those questions usually reveal a clearer narrative than trying to identify the perfect professional label.

A lot of candidates assume their story should be built around technologies, certifications, job titles, or functional categories. More often, the strongest story comes from identifying the recurring problems you've spent your career solving. That's usually what hiring managers are trying to understand anyway.

I hope that helps! Good luck!

If you’re a Premium subscriber and have a question about your job search, email us at contact@jobseekingishard.com and I’ll answer it in a future issue!

That's it for now, and send in those questions! Don't forget to put "Premium" in the subject line so I can stay organized!

Do you have any thoughts or suggestions for the premium membership? Let me know! The premium tier is a work in progress, and I want to create something of real value for subscribers.

Have a good one!

-Adam