The calculus is complicated, even if you’re comfortable with your employer’s plans for Covid safety. Some companies will, at least ostensibly, give workers a choice; others will ratchet up the pressure or dole out ultimatums. How much do you push back? How do you decode corporate statements to tell you what you really want to know: Will it kill my career if I stay home?

The other variables to analyze feel infinite, the stuff of life: that workout you can now sneak in each morning, the leisurely walk to the bus stop with your kid, the exodus of $15 sad desk salads from your lunch routine. But also, wasn’t the chatter and camaraderie at the office the thing that made work feel…almost fun? Who can even remember at this point?

The good news—and the bad news, for the indecisive among us—is that we’re in a unique moment.

“There’s never going to be a better time to make the pitch to your company,” says Ed Voelsing, founder of the Rivet Group, an executive recruiting and talent-consulting firm in the Charlotte area. “ ‘Allow me to work remotely.’ ”

Workers, dreading back-to-office orders, have approached Mr. Voelsing in search of permanent telecommuting jobs. One client moved to Ohio during the pandemic and doesn’t want to give up his new life: cheaper, closer to family.

Mr. Voelsing recommends that employees tread lightly if they’re early in their careers. The office is where you learn by osmosis, tout your work and occasionally get pulled into a random meeting with higher-ups.

“You get to state your opinion in front of a whole bunch of executives who now know who you are,” he says.

Consider how much leverage you have: How rare and revenue-generating is your skill set, and how hard would it be to replace you right now? Are you open to taking a pay cut if it means you can stay remote? How would you feel if your career stagnated a bit down the line because you couldn’t ascend away from headquarters?

Some 43% of 1,046 remote workers surveyed by insurer Prudential in March said they’d be nervous about their job security if they stayed home while others returned to in-person. Yet the data indicates many of us really don’t want to go back, at least not every day. Nearly nine out of 10 workers in the same survey said they want to work from home at least once a week after the pandemic subsides; one in three said they wouldn’t work for a company that forced them to be on-site full-time.

Bethany Goldszer quit her previous job, with a nonprofit in Queens, N.Y., after leaders called everyone back to work last June. Now conversations are bubbling up at her new employer, a charter school where she’s been working remotely, about returning to five days in-person come fall. Ms. Goldszer made a pro and con list about what staying home would mean: no frantic mornings trying to find parking on city streets, no daily tolls—but also the possibility of “people even forgetting that I exist.”

The sticking point was the prospect of having to make her commute a high priority as she begins house-hunting on Long Island.

“I’m tired of making decisions like that,” she says. “I don’t want where I work to factor in.” She floated her remote-work pitch by a board member, who she hopes can advocate for her when it’s time to make a formal request.

Then again, is having no commute the answer? Harvard Business School professor Ashley Whillans says preserving some sort of physical transition between work and home helps us set boundaries. During the pandemic, many filled the time gained from killing their commutes with more work.

“People feel like they have to be chained to their desks all the time,” Dr. Whillans says. Evaluate your remote work experience: Are you capable of maintaining separation and avoiding burnout? Or have you spent the past year logged on at all hours, stressed and miserable?

Gaetan DeSimone, a graphic designer and animator in Easton, Conn., kept a journal chronicling how he was adjusting to remote work and using his extra time. There was the bonus hour with his toddler daughter in the mornings, the ability to pop out to his new garage studio when inspiration struck at 2 a.m., and then head out for a bike ride the next day when he couldn’t focus. His company left it up to him to decide whether to start coming into the Manhattan office. Still, “there’s that looming concern of, what if one day they change their tune?” he says.

He asked his manager if staying remote would affect his future opportunities. When he said no, Mr. DeSimone’s decision was made.

How you’ve adjusted to remote work is only one piece of the puzzle. How did the people around you do with remote work?

“Was your boss extra hypervigilant, calling you every five seconds?” asks Joyel Crawford, a Philadelphia-area executive coach. Maybe showing up at the office will boost trust and actually buy you some more autonomy.

If you’re the manager, consider whether it’s easier for you to lead meetings and rally the troops over Zoom, or in a conference room. Over the past month, Ethan Tyler, a corporate affairs director in Girdwood, Alaska, started to notice that some tasks were falling through the cracks on his remote team.

“I’ve just felt this kind of a disconnect,” he says.

When the group met up at a local restaurant recently, they were able to swiftly outline projects and divvy up work. Conversation felt less awkward.

Mr. Tyler was excited to hear his company was bringing everyone back at least three days a week starting in June. He can’t wait to get in his car and make the hourlong trip to his Anchorage office.

How serious is your company about remote work?

Will staying home hurt your chances for promotion? Will leaders reverse course in a year, ordering you back? Tips on reading the risk, from professor Ashley Whillans:

Office downsizing: If your company is shedding real estate, that could be a sign that it’s committed to a flexible model of working.

Hiring from afar: Are new employees from around the country onboarding into fully remote roles? Or has the company been focusing on recruiting local talent in the past several months? If it’s the latter, executives might be switching gears.

Signals from the boss: Pay attention to what leaders are doing, not saying. “Do you see your bosses Zooming in from their offices?” Dr. Whillans asks.

Subtle perks: Is your company offering things like free lunch to those who come back? That’s a sign they want you there.

Write to Rachel Feintzeig at rachel.feintzeig@wsj.com