9 Tips for Negotiating Fewer Hours at a Day Job (Without Getting Fired)

I recently shared my tips for growing your freelance career enough to quit your day job. In that post, I discussed how I gradually “stepped down” from my full-time job by working one day less a week, then going part-time, until I had enough freelance income to quit altogether.

We received some questions from Penny Hoarder readers who wanted to know more about how exactly to negotiate reducing your work hours — and understandably so. Of all the conversations you have with an employer, the “I want to work less so I can do my own thing” conversation is one of most petrifying.

So here are nine actionable tips, from my own experience and the advice of employment experts and fellow freelancers, to help you in this nerve-wracking situation.

1. Know What You Need

Before you walk into your boss’s office, you must have a solid idea of what you want to ask for. “I want to work less” won’t cut it.

Sit down with your monthly budget and your anticipated side gig income and ask yourself exactly what you’ll need from your employer.

• How much money will help you keep your bills paid?

• Would you rather work half-days throughout the week or work a few full days so you can take other days off?

• Are you open to working from home on occasion, knowing you can get more done there (and hopefully spend some time on your own projects)?

While your employer is likely to offer a counter to whatever you ask, you need to know how much you’re able to budge and which items you consider deal breakers. Otherwise, you’re negotiating blind.

2. Time Your Request Right

The easiest way to kill your chances is to catch your boss on a bad day.

As the keeper of my immediate boss’s calendar, I knew which days he’d likely be stressed out due to big deadlines or a heavy meeting schedule. I also knew which days he tended to be in the best mood, like Friday afternoons right before he left for a weekend trip.

If you don’t have that sort of insider knowledge, try buddying up to another colleague who might, like your boss’s assistant.

“Wait until you’ve reached your recent targets,” recommends Kuba Koziej, CEO and co-founder of Uptowork. You want to make sure you approach your boss from a position of strength:

When you’re ready to talk, emphasize the need for the change to balance your life. Focus on the fact that a better work-life balance would make you happier and more productive. You think that a change in the schedule will help. Back that up with a couple of examples of goals you’ve achieved or targets you’ve met.

This sort of argument is stronger when you’re just coming off an achievement. If you’ve recently missed a goal or two, it’s better to wait until you’ve upped your performance so you have more negotiating power.

3. Think Like Your Employer

As CFO of New Eagle, Mickey Swortzel has been approached by employees asking to decrease their hours to pursue a personal project. She advises:

The key to making this a win-win for both parties is for the employee to think through the financial and workload issues from the company’s perspective.

Some of the questions that are helpful to start the conversation include: How can the work get accomplished? What is the timeline for this adjusted schedule? How is this going to work under your current employment contract?

Put yourself in your employer’s place and brainstorm what fears and concerns your proposal might inspire.

As Evan Harris, co-founder and Director of HR for SD Equity Partners, puts it, your employer “will want to make sure you are not trying to take advantage of the company. Cover your bases and try to discuss any issues that the employer may have with the transition before they bring it up to you.”

4. Emphasize the Benefits for Your Boss

Yes, you want a new arrangement because it will be better for you — but you need to frame it in a way that shows what’s in it for your employer.

Studies have shown employees who work from home are more productive. So are employees who are more satisfied with their jobs. Be sure to emphasize how the new schedule you’re seeking will actually help you do better work.

“Keep in mind that you’ll only achieve your goal if you can convince your employer that you will meet targets,” Koziej says. As he explains, you want to be able to say to your employer, “‘Here’s what it looks like when I’m productive. Now, imagine I’m even happier with the schedule.’”

When I negotiated my step-down, I presented my boss with an estimate of how much time I spent doing billable, paralegal-level tasks only I could do, and how much I spent on basic administrative work.

I proposed he could hire a part-time assistant to do these less critical tasks for a much lower hourly rate than he paid me — and he loved the idea.

The work would still get done and the company would save money. Putting my plan into these dollars-and-cents terms made it much more palatable to him.

5. Go In With a Plan…

The more specifics you can offer, the better.

Presenting a detailed plan shows you’ve really taken the time to think about your proposal and decreases your boss’s ability to generate tons of “what if?” concerns.

“Having a plan ready shows that you are committed to the company and presents the employer with a few choices,” says Harris. “Often, the employer will want to make their own solution, but by presenting an option or two, it steers the conversation into the direction you want it to go.”

Dr. Heather Rothbauer-Wanish, a professional resume writer and owner of Feather Communications, agrees:

When asking for time away to focus on a side hustle, it’s extremely important to let the company know that this will NOT affect your current work with them. For example, stating that you would be willing to work an alternate schedule to maintain the same hours will be vital.

When asking for an alternate schedule, adding a direct compliment to the company and/or manager will be a nice way to break into the conversation.

Here is an example:

“I love my position here with ABC Company. As you know, I am also working on {insert side business here} and would love to allot time to that opportunity, too. Is it possible to come in two hours late two days per week? In exchange, I would be willing to make those hours up in the afternoon or on a weekend.”

6. …But Be Open to Alternatives

“As a rule, in any negotiation, there needs to be give and take,” says Trevor Lamson of Connected Recruiting Ltd.

“What are you willing to do or give up to make this happen? Think about how this affects your employer and have ideas to adapt, work from home on that day or split schedules. Be creative; having solutions always increases success in negotiations.”

Aviva Legatt attempted to negotiate a step-down from her administrative job at the University of Pennsylvania to launch a side business and finish her doctoral dissertation. She went in with a clear request but was flexible enough to pivot when it didn’t work:

I wrote out a list of tasks, what I could do from home, and how much money seemed appropriate with the proportion of tasks versus my full-time salary. When I learned that this kind of arrangement wouldn’t work for my department, I took on another role at the university as a high-performance team facilitator [for another department].

7. Consider Benefits

When asking for a reduced schedule, bear in mind many employers will balk at the thought of extending full-time benefits once you go part-time — although they are required to offer health insurance if you work at least 30 hours per week and the company has 50 or more employees.

If you’re worried about the added cost to your bottom line, consider tweaking your offer to include a lower salary or hourly rate in exchange for retaining some of your benefits, which might also include paid vacation or a 401(k) match.

You can also consider alternative health insurance options available to you, such as joining a partner’s plan. Legatt was still a Ph.D. student at the University of Pennsylvania when she asked to work less, so she was able to switch to a student insurance plan when she was no longer able to use the staff one.

8. Offer a Trial Period

One of the best ways to ease the blow of requesting to reduce your work hours is to offer your employer a way out.

My boss asked that we have regular check-ins to touch base and make sure the new arrangement continued to work for both of us, and I was happy to agree. It reassured him and also gave me a chance to do a test run of my business’s viability.

At first, we met every couple of weeks to discuss my project load and upcoming deadlines. After a couple of check-ins, it was clear I was getting my work done and there were no complaints from the rest of the team, so we met less often.

I made sure to go into each meeting armed with a list of what I’d been working on, as well as an outline for how I’d tackle upcoming tasks, to put my boss’s mind at ease. I suspected he was also polling my colleagues to make sure my new schedule didn’t put any extra work on their shoulders, so between meetings I made sure to work my tail off to get everything done, and done well.

If your boss decides to nix your new schedule after a trial period, you’ve still bought yourself some additional time on the payroll while you decide what to do next.

9. Decide Whether to Be Transparent

How much should you reveal about why you’re asking for a different arrangement? Our sources’ opinions varied.

Lamson, the recruiter, believes that “if this is truly your desire, just be upfront. This is a difficult discussion in itself; accept the fact that asking this may lead to the employer becoming concerned. Be prepared for the repercussions.”

But Adam Hatch, a career advisor at Resume Genius, prefers a more cautious approach. He knows firsthand what it’s like to ask a boss to cut your hours so you can focus on a side business. Here’s what he recommends:

[Don’t] even mention your side business. If your boss asks why you want less time, deflect. You don’t have to explain yourself, so be general. Say you have a lot on your plate, or you need to spend more time with family, or even that you have some projects you’ve been meaning to tackle.

But you don’t need to go into too much detail. Be careful, though; you want to avoid coming across tight-lipped because it will seem like you’re hiding something… you have no responsibility to inform your employer what you are up to during your off hours.”

It all depends on your personal work situation and risk tolerance. If you have a good relationship with your boss, your company has shown flexibility to employees in the past or you have a high risk tolerance, the simplest thing to do is lay all your cards on the table.

My boss knew I’d been working on my writing in my off-hours, so I saw no point in being coy about it. I was ready to accept his reaction, whatever it was, even if that meant finding a different job elsewhere.

In short: Trust your gut.

Reducing Work Hours: A Case Study

Ron Stefanski stepped down from his day job to focus on building websites like Jobs for Teens HQ. His story is a great example of many of these tips in action:

The first thing I did was tell my boss exactly what was going on. I explained to him that I had a side-business that was going well and I wanted to work on that full-time.

Then I told him that the last thing I wanted to do was “leave the company in a bad position because they had been so good to me as an employee,” and I explained that I would be available for them as a consultant if they’d like. The key here was that I was ready for them to say “no,” but was hopeful they would say “yes” as I needed the money.

The arrangement didn’t include any paid vacation or health insurance benefits. My thought was that in order to make this happen, I’d have to become a paid consultant for them because otherwise they’d still have to provide me with benefits, which is a big ask since I was no longer a full-time employee.  

After my boss discussed the situation with the executive team, they agreed that this arrangement would work and we could have a trial period of one month. I went with an hourly consulting cost that was 20% greater than what I was making as a full-time employee because that’s a good estimate of how much an employer pays over a salary for all benefits.

We limited the engagement to six months (with the option to sign another six months if needed) so that I could have an end date that would allow me to work fully on my own projects. In the beginning, I had a lot of work from them, but then they transitioned further away from me as time went on and overall, I would say the arrangement was a win-win for both of us.  

What If Your Boss Says No?

So, the biggest question of all: What if your boss flat-out denies you?

Well, at least you tried, and you’re no worse off than you were when you were working full time and wondering “if only.” Now it’s time to find another way to make your dream happen.

That might mean applying for a part-time job at another company. It might mean switching to a work-from-home job so you have more control over your hours. It might mean “slashing” together a handful of side gigs like dog sitting or selling stuff on Etsy.

There’s more than one way to make time for your freelance business, and as anyone who wants to be an entrepreneur will quickly find out, hustle is only one part of being successful — the rest is learning to never take “no” for an answer.

Your Turn: Have you ever negotiated a new working arrangement with your company? How did you do it? Share your tips in the comments!

Kelly Gurnett is a freelance blogger, writer and editor who runs the blog Cordelia Calls It Quits, where she documents her attempts to rid her life of the things that don’t matter and focus more on the things that do. Follow her on Twitter @CordeliaCallsIt.