From Freelance to Full Time: My Return to the Office

There’s a lot of advice out there about making the jump to freelance. How to set yourself up, the highs and lows. Fewer people talk about what it’s like when you go from freelance back to full time. I did it and lived to tell.

In the space of the last 8 years I’ve gone from full time to freelance to full time again.

When I was a fulltimer I never thought I’d be interested in going freelance.

Then I went freelance for six years and I swore I would never go back to a regular job again.

Now here I am with almost a year under my belt working full time for Proposify.

Obvious lesson? Never say never, my friends.

I’m here to prove that you can survive this teleportation and I’ll share what I’ve learned in the process.

Full Time Freelancing

Before we get too far I want to address the word, ‘full time’ being used as the opposite to ‘freelance’. It’s what most people say to mean they work full time in an office, or in-house.

This maybe suggests that as a freelancer I wasn’t working full time, or rather, not hard enough. Sure, my hours were probably different than someone going to an office every day, but I was still working a lot, and hard. I was a full time freelancer.

But because it’s the vernacular, for the purposes of this article I’ll use the term ‘full time’ interchangeably with ‘in-house’ to mean you work in an office for someone else, as opposed to freelancing.

Just know that I know that all you freelancers out there are working hard for your money.

Freelance to Full Time is not Failure

Sometimes when I was working as a freelancer I thought people might think I had gone out on my own because no one would hire me for a full time job.

Of course that wasn’t true. I had worked many years for other people but I wanted to try things on my own terms and the timing was right with some immediate opportunities for freelance projects. 

The same feeling started to plague me when I considered working full time again. Everyone knew I loved working for myself so after six years if I was really that successful as a freelancer, why on earth would I give that up to work for someone else — unless I had failed?

It really bothered me that people might think I had failed.

But that was just negative self-talk I needed to get over.

My reasons for deciding to go back and work for someone else were varied, the same as my reasons for going freelance in the first place. And none of them involved failure.

The reality is, as much as I loved freelancing, there are a lot of challenges working for yourself.

The Joy of Payday

Regardless of the fact I worked steadily, cash flow was always a bitch.

While I had a couple of regular gigs I could count on, it was hard to know how much work I would have long term, and more worrisome, when I would get paid.

Also, some agencies wouldn’t pay me until their project finished and they got paid so it could be months after I did the work before I would finally see a cheque. If only Kyle had written his post about collecting on invoices years earlier!

I’m not going to pretend that the best part of working full time isn’t the biweekly, dependable paycheque.

It is.

There are a number of other things I like but all things being equal, getting paid regularly without having to chase down clients is pretty damn great.

It’s right up there with PAID VACATION.

Career Advancement

When you work in an office for a company, you can usually see the path you want to follow to move your career forward.

For example, you’re a designer so maybe you work your way up to becoming an art director and then eventually creative director.

But when you work for yourself it can be more difficult to see how you advance your career and skills. Who’s going to give you a promotion? You can crown yourself queen but that doesn't mean you’re royalty.

It’s one of the major reasons I decided to join Proposify. I’d been working in the marketing agency context for almost 15 years. I loved it and I got to work on lots of different projects for different companies but even when I was freelancing I was basically doing the same type of work, offering the same services, producing the same types of deliverables.

So when Proposify’s co-founders Kyle and Kevin — who also happen to be my friends and former co-workers — approached me about joining their team, I was intrigued. 

Here was a chance to work with a startup (something I had never done), to help grow a new business (it was less than 2 years old when I joined), to apply my knowledge and experience to a totally different industry (what did I know about SaaS?), to focus my attention on one brand (rather than five), and to help my friends put the pedal to metal in building their company.

I was happy freelancing and doing the work I was doing but with this offer from Proposify I could see the next step in my career and I could see the potential for how it could help me grow both professionally and personally.

Co-workers

For much of my career I’ve worked with some really great people. I met the bulk of my closest friends through work. That’s part of the reason why I was originally hesitant about going freelance, I liked working with a team. I liked being around people (well, most of them).

Fortunately for me, I was still part of a lot of teams at agencies where my friends worked and I would often gang up with other freelancing friends to work on projects. I generally got to choose who I worked with.

I felt like I had the best of both worlds when I was freelancing  - I worked with people just enough to satisfy the social beast in me and then I could escape all the crazy that can happen like office politics and petty infighting.

When people would ask me if I ever considered going in-house again I would say that I preferred playing the field to getting married.

When I started at Proposify I was looking forward to being part of a full time team again but the reality has been more challenging.

I like everyone I work with but I wasn’t used to being around people all day, every day. I’ve also had to relearn aspects of office culture and working with people with different experiences and backgrounds.

I had spent the last number of years working with people who were very similar to me doing similar work. We were of like minds, similar sensibilities, and similar skills.

Basically I ended up isolating myself, not necessarily in terms of quantity of social interaction but the type of social interaction. So it’s been good to shake things up a bit and break out of my self-imposed bubble.

Pace Yourself

People often hire freelancers because they’re in a time crunch to get things done, whereas working in-house you typically have more time to properly flesh out ideas.

I also would get hired for pieces of projects, so smaller chunks of work to be completed in a shorter timeframe. I was used to kicking out projects quickly, in sprints. Execute, execute, bam, bam. Get it done, make the revisions, on to the next.

So when I started at Proposify I felt like I had to accomplish the role of marketing manager in two weeks.

It was an absurd expectation and one only I was responsible in creating. But I was so used to working on a project-to-project basis with a crazy deadline looming over me that I felt a level of anxiety in the first month working on my job. I WASN’T DOING ENOUGH FAST ENOUGH!

Fortunately I came to my senses and reminded myself that this was a marathon, not a sprint. Yes, there were things to get done and there were deadlines attached but I didn’t need to have everything figured out and executed in the first two weeks.

That’s the beauty of working for one brand instead of twenty. You can think, strategize, execute, test, and try again.

I’m privy to the big picture and able to contemplate what the next steps are, rather than being asked to solve one section of a puzzle I’ve never seen.

Flexibility

This is probably one the biggest benefits most freelancers will list about their jobs. That they can decide when and how they’re going to work.

If I had other things I needed to do I might work for the morning, take a couple of hours in the afternoon to run errands, and then work all evening.

Or if I hit a wall one day and just couldn’t get ideas or words to come, instead of sitting at my desk in agony trying to force my brain to work, I could take a walk, go kayaking, then come back refreshed and ready to rock. Even if I was working under a tight deadline, as long as I met the deadline, how I got there was up to me.

I could decide what kind of projects I wanted to take. I had a rule about working with assholes. I could fire a client or sometimes if the deadline or budget expectations of a project were totally unrealistic, I would just say no. I was never able to do that when I worked for someone else.

Don’t get the idea I was turning down work like some sort of entitled prima donna. But there was a reason I worked for myself and personal happiness was a major part of it. It provided huge peace of mind to know that if I wanted to, if something or someone was really causing me that much stress, I had the power to say no.

Going back to work full time has changed that. Although Proposify is pretty flexible, I don’t have quite the same freedom with my time and I have a more structured work day. But I’ve actually liked that change for the most part.

Working for yourself, you can end up working all the time. There’s always something to do plus when you’re not sure when or if the next job is going to come along, you feel like you have to say yes to every project.

You end up not taking the breaks you need or creating work/life boundaries that are essential to your mental health and personal relationships.

While I often do work-related reading or work on my blog posts in the evenings because it’s quiet, I now am able to keep most of my work happening during the day. I didn’t realize it was that big a deal until my boyfriend mentioned it recently - that it’s been nice that I’m not working all the time.

Move Carefully, Choose Carefully

Overall, while my transition from freelance to full time has been an adjustment, it’s been a positive change for me.

Part of the reason is that I was open to the change, and I was fortunate that an opportunity like Proposify was my re-entry point to the full time world. I chose it deliberately for very specific reasons:  

I’ve known Kevin and Kyle for many years. I know that we share similar values when it comes to work/life balance, to respecting people, to valuing good work and a good laugh at the same time. And they know me  - my experience, how I can contribute to the company, and they trust that I’m going to do my best.

You should keep these things in mind when choosing any job but especially when you’re going from working for yourself to working for someone else.

While there will always be challenges to any change, being on the same page will increase the chances of a successful full time teleportation.

Conclusion

I’m not suggesting that full time is better than freelance or vice versa. They both have their pros and cons depending on your work style, your tolerance for risk, self-discipline, and social skills. It also depends on timing and opportunity.

But having punched from both corners of the ring, my advice is to be open to the idea of change — either jumping into freelance or returning to full time — and recognize that change brings growth.

For me, that change led me to Proposify.