Why Indy
Free Resources
indy university
Start for free

The Five Questions to Ask Yourself Before Returning to a Full-Time Job

Mar 24, 2021
(updated: Dec 2, 2022)
Max 5 min read

Last week I told you about the five questions that you should ask yourself before quitting your job to go freelance full time. But what about the opposite? What about when you’ve been working freelance full time but you feel that it might be time to take a full-time, salaried job again? You’re going to need to ask yourself a different set of questions before going that route. 

How is this job different from the one that made me leave full-time work?

Whatever your reasons for considering taking another full-time job are, it’s smart to make a list of all the things that made you leave the 9-5 life in the first place. Use this list when evaluating potential new jobs. Of course, no job is going to check off every box and allow you the exact same lifestyle you enjoy as a freelancer. You always trade some freedom for the security of benefits and a consistent salary. But you can still use your list to help find jobs that offer certain aspects of the freelance life. Especially in this post-2020 world in which remote working has become widely accepted, you can reasonably expect many roles to offer a semblance of the freedoms you enjoy as a freelancer.

What tradeoffs am I willing to make?

But when it comes to the aforementioned tradeoffs you should draw a line somewhere. When the freelance checks start drying up and you look back to the full-time world you can compromise pretty quickly. You may start saying “Well, maybe I wouldn’t mind having a strict schedule” or “I guess it wouldn’t be too bad to spend 50% of my time on administrative tasks” or fill in the blank with whatever it might be that would make you run from a potential job under normal circumstances. 

The list I mentioned above of the things that made you flee full-time work to begin with can be helpful to prevent you from making tradeoffs that will cause you to start dreaming of quitting your new job within three months. It’s easy to panic when things aren’t going well with your freelance clients, but sometimes it can be better to refocus on finding new clients or a new niche instead of making tradeoffs that could ruin your day-to-day life. 

Can I still work on my freelance/side gig/passion project on the side?

One thing I have run by each and every boss I’ve interviewed with in my career is whether I can still do my freelance writing on the side. No matter what I’m supposed to be writing about at my day job, I want to know that I can still write about things that I’m passionate about in the evenings. I’ve written some soul-sucking things between 9-5 at other jobs, but the ability to come home and write travelogues about Iceland or interview famous adventurers makes the grind a little easier during the day. Sometimes it can be the best of both worlds. You get the full-time paycheck and benefits, but you still get to do things you’re passionate about with your skills. If you’re a graphic designer, maybe you don’t love making company logos all day at work, but if you can still do freelance illustrations for a friend’s comic book in the evenings you can get that creative buzz you need to keep going. Some jobs will take up all of your time or will frown upon you doing outside freelance work, I would advise steering clear of those roles when interviewing for full-time jobs. 

What kind of freedom will I have?

Perhaps the most important benefit of freelancing is the freedom you have to work wherever, whenever, and however you want. Depending on your specific clients and roles that may not always be the case, but by-and-large that is why people join the freelance world. As our writer Matt Crossman says, one of the most important things he’s learned as a freelancer is to take advantage of the ability to enjoy long lunches or play with his kids. Getting back into full-time work can put an end to these freedoms. But in today’s remote-friendly world you can negotiate for some of these freedoms. Work better in the evenings? Ask if you can take some time off during the day with the understanding that the work will be done on time. Or maybe you prefer to work from a coworking space; many companies offer to subsidize or pay in full for their remote workers to have a desk or an office in one of these spaces. Again this is a good time to write down the things you will miss most about freelancing and try to find jobs that can offer these benefits. 

Is this going to put a cap on my earnings compared to my freelance money?

Some are looking to get back into full-time work because their freelance income isn’t cutting it, but others are looking for different benefits. Among those would be health insurance and retirement benefits. Some are just looking for the consistent paycheck instead of the roller coaster of freelancing. However, one thing to consider before being drawn to the allure of that consistency is whether the capped income of a full-time job would be limiting your money-making ability. Some freelancers can make significantly more independently than they would by taking a salaried position. Do some math and project out whether you would actually be able to make more during an average-to-good year than you would from the salary being offered at your potential new job. If you can, I would suggest not using 2020 as an example year considering how incredibly unique it was. For many, it was the most challenging year of their lives. But for some in certain industries it was a really great year. I would base predictions off more normal years to try and project earnings in 2021 and 2022. 

If you’ve ever been in this scenario you’ve likely asked yourself a lot more than five questions. The important thing when thinking through making big decisions like this is to avoid impulsiveness. Don’t act out of panic or fear, but instead take every piece of information into consideration and make the right decision for both you and your family. One other thing to keep in mind is the fact that you can always go back to freelancing if the full-time role doesn’t work out. That’s the beauty of freelancing. If you need help organizing your freelance gig including contracting, invoicing, proposals, and more check out Indy!

Get started today!

Get the tools to manage your entire freelance business, free online courses to accelerate your growth, and join a community of freelancers just like you.
Mail icon
Join our
affiliate program
Get 90% commission for Indy Pro sign-ups via your affiliate link!
Want more freelance tips?
Crush freelance struggles with weekly tips delivered to your inbox.