The Los Angeles Dodgers are trying to do something no National League team has ever done. After winning the 2024 and 2025 World Series, they’re facing the Milwaukee Brewers in the National League Championship Series. The last Major League Baseball team to win three in a row was the 1998-2000 New York Yankees.
Winning twice gets harder in part because success takes away the pressure to change. Five years into a cleared role you’ve mastered, you may be feeling a version of that right now. The work runs smoothly, and people trust you with it. That’s when a career plateau can settle in without anyone noticing, you included. What follows will help you check whether you’ve started coasting and figure out what to ask for next.
Why Winning Again Is Harder Than Winning Once
The Dodgers could have stood pat after their second title. Instead, they signed outfielder Kyle Tucker to a four-year, $240 million deal and added closer Edwin Díaz. Andrew Friedman, the team’s president of baseball operations, said the organization stays focused on finding ways to get a little better each year.
The same pressure shows up in your career, more quietly. By year five, you’ve probably tuned yourself to the job as it looked when you first mastered it. The work around you hasn’t held still since then. New requirements can reshape what the job asks of you, and a reorganization can change who you answer to. Even a newly approved tool can change how your team works. Because you’re good at the job, none of those shifts feel urgent when they happen.
How to Spot Coasting Before Your Manager Does
Managers tend to notice a career plateau before the person in it does. They read the same results, described the same way, review after review. Check yourself before that happens. If two or more of these sound familiar, you’re probably coasting.
- You can’t remember the last time something at work was hard to learn.
- Your last two self-assessments could trade dates without anyone catching it.
- The problems people bring you are the same ones they brought three years ago.
- A newer teammate got comfortable with a tool before you did, and that didn’t bother you.
- “Busy” is your standard answer to how work is going, but you can’t name one thing you’ve improved lately.
All five can show up in someone whose reviews still look strong, so a good rating doesn’t rule anything out.
What to Ask For Next: Take the Mookie Betts Route
Mookie Betts had already won six Gold Gloves as an outfielder when he moved to shortstop for 2025. It’s one of the hardest positions on the field, and the Dodgers’ general manager said he was ready for the challenge.
Your next ask can follow the same logic. Once you’ve mastered a role, the strongest move is usually a harder version of work you already do well. A title change may follow, but it shouldn’t be the ask.
For a cleared professional, that could mean leading onboarding for people who are new to your team. If your program is upgrading a system or changing a process, ask to own a piece of it. If your organization competes for new work, helping on a proposal is another option.
Bring it to your manager in plain terms. Try something like this: “I’ve got [area] running without much oversight now. Over the next six months, I’d like to take on [harder responsibility]. What would you need to see from me to make that work?”
Ending on that question gets your manager to name specific criteria instead of a vague yes or no.
Be realistic about the limits. Cleared roles often come with firm boundaries. A formal job description, an agency position description, or a contract’s scope can all limit what you take on. If the honest answer is that your next step lives on a different team or program, that’s still worth knowing.
Make the Ask Easy to Say Yes To
When the Dodgers announced the Betts move, the general manager pointed out that it freed the team to pursue another outfielder. They had already planned for the gap the move would leave.
Your manager will want to know who covers your current work, so answer that before it comes up. A sanitized handoff document or runbook for the responsibilities you’d step back from does the job. So does naming the person you’d train to take them on, along with a short training plan.
Stick to process steps and timelines, and keep program names, customer details, or anything controlled out of it entirely. Your organization’s documentation policies still apply.
Mistakes That Keep You Stuck
The most common mistake is asking for a bigger title when what you need is harder work. A new title on the same scope rarely changes much about your day or your growth.
Timing trips people up too. If you wait for your annual review to raise this, your manager has likely already formed an opinion. Others read silence as proof they’re still sharp, when it may only mean nobody has looked closely.
Last, don’t leave your current work messy on your way to the next thing. The trust you built in this role is what makes your manager willing to say yes.
Get Better While You’re Still on Top
Nobody knows yet whether the Dodgers will finish the three-peat. Whatever happens this postseason, the approach is worth borrowing. The front office kept adding to a roster that had already won. The team also asked one of its best players to take on a harder job.
You can make that same bet on yourself before your career plateaus. This week, run through the five-item check above. Then write a short paragraph on the harder version of your current job, and bring it to your next one-on-one.
