Done With the Freelance Life? Here’s How to Transition to a 9-to-5 Job

Heather Comparetto / The Penny Hoarder

There’s a lot of advice out there for people ditching their 9-to-5 jobs for freelance life. Some of it has come from this very website, because we’re supportive of alternative career strategies.

Hustle is hustle, right?

But what happens when you get an amazing job offer and decide to ditch your freelance life for a day job?

After five years being my own boss, I was so tired. Working for yourself is empowering, but it can also be emotionally and physically taxing. I wanted a support system for the next phase of my career.

Since I had already worked for The Penny Hoarder as a freelance writer, I thought switching over to life as a full-time employee would be easy. Seamless, even.

I wasn’t worried until my mom asked if I was ready for the change. “Are you going to be OK with this?” she asked, not unkindly. “Are you ready to give up your freedom?”

Way to be a downer, Mom. I started looking for advice for transitioning successfully, and found few options. Had no one else made this decision before?

Ultimately, I went bravely where so many thirtysomethings have gone before: to work.

Here are a few lessons for those doing the same, both with gusto and relative ease.

Don’t Change Your Routine Overnight

Prepare for your new job like you used to prepare for the first day of school. Pack your bag, plan your lunch, iron your shirt and get a good night’s sleep.

But if your new job presents a dramatic schedule change, you’ll need to plan further ahead for a smooth transition.

As a freelance writer, I typically worked from 10 or 10:30 a.m. until 6 or 7 p.m. Morning meetings? Something I tried to avoid.

I still thought I’d suddenly start popping out of bed around 8 each morning.

You know what happened? I overslept on my second day of my new job.

My supervisor forgave me, but I (still!) remain mortified to admit this transgression to the public.

If you’re changing your routine to take a full-time job, give yourself at least two weeks to shift your sleep schedule. The National Sleep Foundation suggests adjusting your lights-out time in 15-minute increments; a slow transition will be easier on your body than an abrupt change.

Get Ready to Communicate. A Lot.

When you’re a freelancer, no one really cares how you get from point A to point B as long as you get the work done.

When you go back to work for someone else, get ready to communicate early and often. Your boss may not look over your shoulder all the time (we can hope, right?), but do expect to provide regular updates on the tasks you’re focusing on. You can’t ghost while you’re polishing all your projects to perfection.

This isn’t the time to get in the habit of sending long-winded memos, either. However, you should check in by email, Slack, or your team’s preferred method of not actually speaking to one another to provide updates on your work. You will find the right balance between MIA and TMI quickly.

Ask Questions, and Don’t Apologize for a Single One of Them

As a freelancer you figure everything out, from tax payments to health insurance. Meanwhile, your full-time job is likely to come with benefits you haven’t seen in years, if ever.

Don’t skimp on the chance to read over your benefits documents and ask your office’s human-resources team lots of questions.

I still notice that when I send a question to our HR pro, I usually start with a phrase that minimizes my request, like, “I have a silly question for you,” or “this might seem crazy, but…”

Stop doing that! When it comes to the complex world of earnings, withholding, benefits and perks, you can’t possibly expect to know it all.

Ask away. Learn.

“I found that transitioning back into full-time work was pretty easy,” Marian Schembari, who later went back to self-employment when she launched Oh Hai Copy. “It was such a relief to not think about work all the time. To have someone else calling the shots. To go home at a reasonable hour and not check work emails at 2 a.m.”

But she admits that full-time work eventually stifled the entrepreneurial mindset she had developed.

“It’s easy to forget that just because you have a traditional job doesn’t mean you have to be a traditional employee,” she says. “Granted, your freedom to get creative and push back really depends on your new manager, but it doesn’t hurt to think through what more creative skills you bring to the table and really try to turn your new job into a flexible role you’ll love for years.”

Go home at 5 p.m. when you can. Do not check your email at 2 a.m. But do keep an eye out for opportunities to thrive in your new role.

Give Yourself a Break

You’re experiencing a big change, so be nice to yourself. My role at The Penny Hoarder requires little to no physical activity, but I was surprised by how physically tired I was at the end of a full day of work. My brain felt fried, and my maladjusted sleep schedule (see above) wasn’t helping.

The solution? Try to chill out.

First, I tried not to overschedule my evenings during the first few weeks of my full-time job. It’s easier said than done, especially when you used to do laundry at any old time of day and now you’re banishing your home tasks, like doing dishes and cooking, to the evening hours.

I’m still moonlighting on some freelance-writing projects, but taking a break between “shifts” has been essential for survival. Take a power nap, go to the gym, have dinner with your family — take time to reset before you get back to work.

Spending even just a half-hour at the gym in the early evening has helped me stir up a bit more energy for my after-work tasks, while clearing my head for fresh thoughts to percolate.

And while you’re thinking about clocking out at 5, start thinking about your newly found vacation time. “Freelancers are really bad at stopping, ever,” Dana Sitar, a freelance blogger before joining The Penny Hoarder, says. “When you work a 9-5, you should stop on evenings and weekends and take your allotted vacation.”

“I find comfort and even more productivity in teamwork and delegation,” Lizabeth Cole, our director of media relations, admits. “I have also found more time to be present with my friends and family, or at a Pilates class because the decision that I made [to take a full-time job] allowed me to reel in the guilt and 24/7 schedule that freelancing had me locked into.”

There’s a lot of talk about the perks of freelance life, but I think I’ll enjoy life as a full-timer for a while.

Your Turn: Have you ever left the freelance ranks to take a 9-to-5 job? What lessons would you share from your transition?