should I apply for the stretch job or the slightly-less-of-a-stretch job?

A reader writes:

I learned through a listserv that several positions are open at a consulting firm. One is a senior level position that involves developing curricula and trainings for a variety of clients. This one made my heart race: it scares me because it would be a huge new challenge with much higher stakes, but feels more aligned with my long term career goals and really exciting. I immediately started writing a cover letter and tweaking my resume. And I wrote back to the person who posted it on the listserv and asked for a hiring manager’s name for this specific position and she nicely shared it with me. So theoretically, I could ship this application out tomorrow.

But I keep doubting my abilities to get my foot in the door, let alone succeed in the job.

This firm is also hiring a project manager. Being a project manager is not my long-term goal. But in some ways this feels like a more natural next step from what I’m currently doing, and I keep thinking that maybe I should apply for that, see if I can get an interview and get hired, and then see if it makes sense to eventually try to transition onto the trainings team.

Is this a YOLO/Lean In moment where I should apply to the harder reach of a job, or should I Lean Sideways-Diagonally-In and apply for a job that’s less exciting on paper, but would still challenge me a lot and which might be a more realistic way out of my miserable current job? I should definitely only apply to one of the two, right?

Without knowing how much of a reach the first job would be for you, it’s hard to say. If it’s one step up, absolutely you should apply. If it’s more of a stretch than that — if it would mean skipping several normal rungs on the ladder to get there — then it’s more of a question.

Do you meet most of the qualifications they listed? If so, it’s not so far out of reach that you shouldn’t apply. On the other hand, if you don’t meet many of the qualifications, then that’s an answer too.

As for whether you have to pick one and only one … I get asked versions of that all the time and wish I had a definitive answer for it, but I don’t. At some places, the best thing to do would be to apply for both. At other places, they’d really want you to pick one. And at some places, if you applied for one, they’d still consider you for the other if they thought it was a good match. Others wouldn’t. There’s just no one answer that works all the time for this scenario, so you’re left doing what feels like the most sensible option to you in the specific context you’re facing.

In this case, I do think that if you apply to the project manager position and not the senior role, they probably won’t consider you for the senior one … because you’d sort of be saying “I don’t think I’m ready for that role,” and if you don’t think you’re ready, they won’t either. Of course, the flip side of that is that if you only apply for the senior role and not the project manager role, you risk them assuming you wouldn’t be interested in the latter and thus considering you for neither.

So there’s just no perfect answer.

But given the specifics of your case, I don’t see why you can’t just apply for both. You’d need to write a separate cover letter for each (making each quite distinct from the other; no sending a generic letter here and just changing the first paragraph), and mention in each that you’re also applying for the other role and why. That feels straightforward and reasonable to me — and if it does to you too, then I say go for it; after all, part of the hiring process is to weed out people who define “reasonable” differently than you do.

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