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June 28th, 2025

Situationships

How to help a friend stuck on the career ladder

Karla L. Miller

By Karla L. Miller The Washington Post

Published June 27, 2025

 How to help a friend stuck on the career ladder
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Reader: I'm writing on behalf of a dear friend who is the "rugged individualist" type and not one to seek outside help or advice. She has climbed the corporate ladder to a director-level position and is well regarded in her field. She enjoys working on data analysis and research but is weary of administrative and managerial chores like vendor contracts and annual reviews. Also, she has hit a wall: There's no real opportunity to move further up at her firm, and there are very few firms in her industry with a department focused on her skill set. She has been in contact with recruiters, but nothing has come up. She's a few years from retirement.

I have suggested she consider stepping back to a lower-level position where she could do the work she enjoys without dealing with the management headaches. Yes, it would be less money, but her kids are out of college, so her budget is more flexible.

My friend seems open to the idea, but I think she worries that she would be seen as beating a retreat or unable to "hack it," even though she has proven herself again and again.

Is there a way to frame this notion in a cover letter or phone call? I imagine a recruiter would look at her resume, say "overqualified," and move on to the next applicant.

Karla: She's looking to move further up the corporate ladder; you're suggesting she move down. Let's take a look at both of those options.

One frequent complaint about advancing into management and executive status is that it leads people away from the satisfying work that drew them to that career in the first place. So seeking a promotion at either her current firm or another is unlikely to resolve the administrative drudgery and management stresses.

On the other hand, seeking a full-time job with a lesser title and lower pay could undermine her at the peak of her career - not necessarily because people will think she can't hack it, but simply because it makes no fiscal sense to go out of your way to accept less than your time is worth. That's especially true the closer she is to retirement, when she needs to be maximizing her savings.

Although your friend can't move up and doesn't want to move down, however, she still has bargaining power and professional collateral that could help her move laterally, exchanging income and title for something of equal or greater value, such as time.

For example, I know quite a few full-time consultants who have managed to have it both ways: Securing a promotion to "business owner" while freeing themselves up to focus on the work they find most satisfying. They write their own job description, choose the services they want to provide (or charge more for the services they don't), and set rates that reflect their market value. Those other companies in your friend's industry that don't have a department built around her skill set or the budget to hire a full-time analyst of her caliber? They probably still need her skills and may happily pay her to provide them a la carte.

Of course, the contractor life isn't for everyone. (I talk a good game, but I'm all about that predictable paycheck.) It involves more risk and less of the built-in resources a third-party employer provides, such as tax withholding, health insurance and a 401(k) match. It also brings its own administrative grunt work: Contract negotiation, invoicing and building a client base. In terms of mental labor and responsibility, it can be more demanding than being a full-time employee.

Fortunately, your friend's reputation and experience could give her options for gradually transitioning to the setup she wants. If her company allows any flexibility, she could negotiate to swap some pay for a shorter workweek. That would reduce her total income, but the value of her actual working hours would remain constant. Meanwhile, she could use her extra time off to plan her next steps, perhaps with the support of a career coach or accountant.

If she's ready for contracting, her current employer could become her first client, enjoying the benefit of her skills and institutional knowledge at a lower administrative cost. (Note: She would need to familiarize herself with the legal differences between full-time employment and contracting to make sure she doesn't end up performing the directed labor of a full-timer without any of the benefits.)

Of course, as with any letter I receive from friends, parents or other third parties, the entire discussion of your friend's options is academic. The decision to hang out a shingle - or not - is hers to make, and it's best undertaken with professional guidance. Your role as a dear friend is to listen more than talk; validate her feelings rather than advise her on what to do about them; and support whatever she decides is best for her well-being.

Karla L. Miller advises on workplace dramas and traumas.

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