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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.

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“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

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• 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.

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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.

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