Dear Anna,

I’ve been with my boyfriend for three years, and I love him—he’s funny, supportive and kind. Right now, we’re living at my sister’s place while saving for our own apartment. He’s 29 and I’m 27. I work full-time as a freelance writer and make a comfortable living, but his part-time retail job barely covers his own expenses, so moving out feels like it’s slipping further away. He’s tried a lot of different things—short courses, odd jobs—but nothing sticks. He says he wants to find a career, but he doesn’t know what path to take and has no degree, certifications or family support. I keep thinking a tech role would suit him, but I don’t want to micromanage his life. How can I encourage him to take the lead and figure out his next steps? — Not Your Career Coach

Dear NYCC,

You’re in a tricky spot—equal parts romantic partner and unwilling project manager—and it’s wearing you down. You clearly care about him, but you’re also watching the clock tick on your own dreams while he scrabbles to find his footing. That tension isn’t just financial; it’s emotional.

First, it’s worth naming what’s going on here: You have different levels of stability and direction right now. You’ve built a career you can live on, and you want your own place. He’s still in the “trying things out” phase, which would be fine—if it weren’t holding back shared goals.

I’ll also say that not having family support is no small thing—it raises the stakes for trying something new. Without a safety net, even a small risk can feel like stepping off a cliff. You do have your sister’s help right now, which is a gift. It’s not an excuse for his inaction, but it is a factor worth keeping in mind.

At the same time, you’re not wrong to want him to step up. Love isn’t about carrying someone forever while they drift. Even in relationships where one person isn’t working outside the home or contributing financially, there’s still a shared sense of contribution and commitment. Moving toward stability isn’t just about money—it’s about him showing you that he’s equally invested in building a secure, shared life.

But here’s the catch: You can’t will him into taking the wheel. If you try to plot out every step for him (“I found you a coding course!” “Apply to this!”), you’ll end up either resenting him for not taking ownership or he’ll feel parented, not partnered. (Possibly both.)

Instead, think of your role as opening doors, not dragging him through them. This can sound like:

“I know you’ve been trying to figure out your next move. Do you want to set aside an evening to brainstorm together?” Or: “You’ve talked about wanting a better-paying job—what’s a small step you could take this week?” Or: “What do you need from me to help you follow through?”

The key is that the ideas and the action steps come from him, not from you. You can encourage, but don’t do the legwork.

It might also help to set a shared timeline. This isn’t an ultimatum (“Get a new job or I’m out”), but more of a checkpoint: “I’d like us to be in our own place by next summer. To make that work, we’d need to bring in X per month. What’s your plan for getting there?” Numbers make things concrete—and harder to avoid.

Also, watch for the difference between being “lost” and being unmotivated. Plenty of people don’t know their exact career path but still work steadily toward something. If he’s consistently avoiding any steps that move him forward—whether that’s job hunting, training or sticking with something long enough to build experience—that’s not about lacking direction. That’s about avoidance.

It’s worth taking a step back and asking yourself a few key questions—not just about him, but about the relationship and what you want for your own future.

-- If nothing changed for the next year or two, would you still be happy in this relationship?

That’s not a trick question. If you imagine life exactly as it is now—same living situation, same income, same patterns—does that feel sustainable and satisfying? If the answer is no, that’s a sign that change isn’t just preferable, it’s necessary.

-- How much financial responsibility are you willing to carry long-term?

Sometimes one partner makes more than the other, and that’s fine. But here, it sounds like the problem isn’t just income disparity—it’s uncertainty about whether your partner is moving toward a career path at all. You should clarify for yourself: Are you OK being the higher earner indefinitely, or do you want a partner who contributes at a certain level?

-- Is your frustration about money masking deeper concerns about drive or compatibility?

It’s tempting to focus on the job situation, but often the real question is: Do you feel like you’re working toward a shared future together, or does it feel like you’re dragging him toward one? Money stress is real, but mismatched ambition or values can be harder to fix.

These aren’t questions to spring on him over dinner like an ambush; they’re for you to sit with first. Once you’re clear on your own boundaries and expectations, you can have a more direct conversation about what you both want and how you’ll get there.

If you decide you want to stay together and move forward, think about setting small, concrete milestones: applying to a certain number of jobs per week, completing a specific certification, or saving a set amount toward moving out. This makes progress measurable and gives both of you a sense of shared momentum.

The goal isn’t to light a fire under him with pressure, but to figure out whether you’re on the same team, moving toward the same horizon. If the answer is yes, then you can work together to make that future happen. If the answer is no—well, that’s important information too.

If months pass and you’re still in the same place, it’s worth asking whether you’re building a life with him, or building one around him.

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