Negotiating a raise

Afraid you’re being pigeonholed at work?
Here’s what to do about it.

How to find and prioritize opportunities to branch out in your career today

by Josh Doody

What’s it mean to be pigeonholed?

“Pigeonholed” is a weird term, so here’s what it means to me.

Maybe you have several years of experience and have gotten pretty good at your job. You’re paid pretty well, but have run out of places to go. There are no logical promotions, no new challenges to tackle, just more of the same old routine.

Your salary has been flat for the past few years because it’s never a great time to ask for a raise, and you feel like you’re just doing the same thing over and over and over. You might hear yourself described as “the Receivables person” or “the tester” or some other term with a single focus.

You’re stuck on your career path, possibly boxed in by your own success, and there’s no obvious next step for you.

You may have been pigeonholed.

Here are two ways to escape your dead-end job and avoid being pigeonholed

What can you do to avoid being pigeonholed and continue making progress in terms of responsibility and pay?


There are the things you were hired to do, and then there’s a lot of other valuable stuff that isn’t necessarily your job. If you only focus on the things you were hired to do—even if you’re very good at those things—you run the risk of being pigeonholed.

There’s always other valuable work to be done in a business. This is true whether you’re an experienced software developer or a marketing intern.

Listen carefully for signs that there are other opportunities to do valuable work and then capitalize on those opportunities.

Here’s what to listen for:

  • “I just didn’t have time to get to it this week.”
  • “Someone should look into that.”
  • “Why does this keep happening?”

Those are all opportunities for you to branch out beyond your regular tasks and find valuable new ways to contribute. Think of them as side quests at your job—what are the optional things you can do that will give you new experience and help you stand out?


Not hearing those kinds of statements floating around your office? Time to go on the offensive!

Ask your manager and colleagues what they’re struggling with. Here’s the “ask” version of the three things I suggested you listen for above:

  • Ask your manager “Is there anything you’re struggling to get done that I can help out with? I want to learn more about how our business operates and help where I can.”
  • On your next team call or standup, you can ask “Are there any long-running things we’ve had on the back burner for a while? Anything I can help us finish?”
  • Ask a couple of peers “Is there anything you keep bumping into that’s slowing you down or making your job harder? Tell me about it so I can look into it and see if it’s affecting other people on our team.”

Regularly listen and ask for new ways to branch out

One big reason you can get pigeonholed is that you get comfortable doing what you’re good at. To avoid being pigeonholed, you’re going to have to step out of your comfort zone and do new things.

The more new things you try, the more often you’ll add another skill to your repertoire, and the more likely you’ll be to find promotion opportunities or even new career opportunities to help you get un-stuck.

How to prioritize the opportunities you identify

By listening and asking, you’ll find valuable opportunities to expand your skillset. But then you need to prioritize the opportunities you found so that you focus on the things that are most valuable to your career at its current stage.

So how do you know whether to learn more about your current area of expertise or if you should add new skills to your repertoire in different areas?

The real question is: Should you go wide or deep?

As usual, “It depends!” 😉 So here’s one way to think about this question as you decide where to invest your time, which is your most valuable asset.

Short-term gain

Going deeper by learning more about your current area of expertise can often pay off well in the short-term. For example, a Software Developer who learns a new programming language or jumps into a new part of “the stack” can put that new knowledge to use right away.

That could mean a promotion or a raise very soon after acquiring that new skill.

Or a Project Manager at a Client Services company may earn her PMP Certification, which will often be rewarded with higher pay or a promotion soon thereafter.

Going deeper on your current skillset can pay off faster. But relative to adding a brand new skill to your arsenal, the payoff may also be smaller.

Long-term gain

Going wider usually takes longer to pay off. For example, maybe that same Software Developer sees an opportunity to start learning about Operations inside the company. That learning process will take a while, and there probably won’t be any immediate payoff in terms of a promotion or raise because it will take a while for the Dev to become proficient enough in this new area of expertise to add real value to the company.

Or maybe the same Project Manager decides to learn more about portfolio management at her company so she has more opportunities to move into a Practice Director role later on.

These things take a while because you’re often learning a totally new skill and because you’ll need time to apply that skill in order to add additional value to the company. But once you have that new skill and can leverage it to add value to a company, the payoff can be much larger because you’re able to influence an entirely new business function.

So should you go wide or deep? Both! Start by getting good at your core job function—going deeper—and when you feel you’re running out of room to improve, look for an opportunity to add a new skill to your arsenal by going wider.

Throughout your career, you’ll have more opportunities and make significantly more money if you alternate going deeper and going wider as you progress. By actively looking for new opportunities to add value in your role and then prioritizing those opportunities for short- and long-term gain, you’ll avoid being pigeonholed and earn a lot more throughout your career.

Using Skill Stacking to amplify new skills

Sometimes, you should pursue opportunities to gain a deeper level of experience with a skill you already have; other times, you should pursue opportunities that give you a broader skillset to draw on.

Let’s talk about why building a broader skillset makes you more valuable and will help you to be ready when big new opportunities become available. And I’ll explain why you should look beyond your current job for opportunities to add new skills to your repertoire.

Skill stacking

The value in learning new skills is in combining them to do unique new things. For each new skill you add to your repertoire, you could gain multiple new skills that you didn’t have before. So if you have two skills and you add a new skill, you may have more than three total skills now.

Why? Because that new skill might also augment your existing skills to create more new skills.

Let’s call this Skill Stacking. I didn’t invent this term, but I like it so I’m using it :)

Here’s an example of Skill Stacking:

Let’s say you’re a video game character and you have two skills: jump and crouch. That’s all you can do. These are great for when things are coming at you because you can jump over them or crouch under them. But that’s about all they’re good for and you’re mobility is limited because you can’t really move side to side.

You learn a new skill—Run—and now you have three skills.

Ah ha! You no longer have to wait for things to come to you—you can go to them. You can explore and move around.

But here’s where the magic of Skill Stacking comes in to play.

You can also combine your new skill of running with your two previous skills of jumping and crouching. Because these three skills work so well together, you have gone from two to at least five skills by adding only one new skill to your repertoire. Here’s what you can do now:

  • Crouch
  • Jump
  • Run (new)
  • BONUS: Jump across gaps by running and then jumping (new)
  • BONUS: Slide under things by running and then sliding (new)

While you only added one new skill, you actually gained at least three new skills.

Sometimes, a new skill is just one new skill. But most of the time, you can combine a new skill with other skills you already had to create even more skills.

Each of those new skills—the ones you explicitly add, and the ones you gain by combining existing skills—may be valuable in its own right. And the more valuable skills you have, the more opportunities you’ll get and the more you can earn throughout your career.

A simple real-world example

Here’s a less abstract example.

Let’s say you’re pretty good with Excel. You can use basic formulas, you’re comfortable with data manipulation like filtering and sorting, and you can create simple charts and graphs to display the data. Maybe you use this for understanding some of your projects at work.

Then you learn PowerPoint. Nothing fancy, but you can put some text and bullets in your presentations, and add graphics like screenshots and pictures.

You have now learned two skills: Excel and PowerPoint. But you also have access to a third skill: Reporting.

You can create charts and graphs in Excel, then include them in a PowerPoint presentation, and create useful reports for your team or for management.

So by adding “knows PowerPoint” to your repertoire, you added one new basic skill, and Skill Stacking means you also added another valuable skill that can help you communicate with management and gain more visibility for the other work you do.

You can also look for opportunities to add new skills outside of work that might pay off for your career as well. Reading books on new subjects or picking up new hobbies could net you new skills that you can stack with the skills you typically use at work.

Maybe that podcast idea you’ve been knocking around will give a chance to work with the Marketing department to edit their new podcast. Or maybe that little toy React app you’ve been building on the weekends could give you a chance to build a prototype for a new app your company wants to launch.

Keep a lookout for new skills you can stack so you’re ready when valuable new opportunities open up at work. Those opportunities will increase your earnings and add variety to your career.

You've changed jobs before and felt like you were leaving money on the table. You never have to feel that way again.

In this free 5-email series, I will show you how to conquer that feeling for good.

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      I'm Josh Doody, a professional salary negotiation coach who helps High Earners negotiate their job offers. On average, High Earners improve their first-year compensation by $47,273 with my help.

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