Going From Freelancer to Employee

There are so many blog posts out there about switching from being a full-time employee to a freelancer. I should know—I wrote some myself.

But back in December when I made the decision to accept a job (a full-time job as an employee!), I started Googling (because that’s who I am). Here are a few of my searches:

• “advice for going from freelance to employee”

• “what to know going back to being an employee”

This shouldn’t come as a surprise, I suppose, but there isn’t a lot being written out there about people who go from freelance to being an employee. A lot of this is because the SEO for these search terms is dominated by people selling courses (big surprise) and a lot of this content is about switching to being a freelancer (and hey, why don’t you buy this course to help you learn how to get clients??).

People who are quitting freelance to go back to being an employee aren’t a money-making opportunity. And that’s just fine.

For me, being a freelancer was really challenging, it was outside of my comfort zone, and it helped me grow a lot as a person and in my career. Was it my forever plan? Absolutely not. I went into it absolutely knowing that. ⁠It was simply something I had to do to make money for the time being, because I found finding a job really challenging—I had really strict guidelines I wanted when it came to being both a parent and an employee.

Freelancing can be really hard. Working for yourself is not the way the Instagram gurus like to portray. Have you ever seen those ads where those same gurus brag about selling 6-figures worth of services in a month? Well, someone has to do 6-figures worth of work if they sell it--so that means they work a lot... and that’s if they’re being honest about how much they sell their services. (The truth is probably that they aren’t making that much money. There is a huge controversy right now with coaches being exposed for not making the big bucks they said they did—which basically renders their services null and void. Shockingly people who work a lot and make a ton of money at their jobs typically don’t spend time bragging about it constantly.)

This is all to say: lots of people go from being freelancers to employees and thrive because of it. If you like me are doing Google searches to see if anyone has lived that, I hope you find this and know you're not alone. ⁠

I did want to share a little bit more about what I’ve been mulling over when it comes to this big change in my life. Let’s dive in!

1. Working for yourself isn’t for everyone (and we have to stop pretending that it is).

Here’s the thing: it’s totally ok to be “just an employee.”

I feel like the mood on the internet is often that working for someone else is useless and your career is only valuable if you start your own business. I just simply don’t believe that’s true. We all find ways of feeling valuable. If owning your own business or freelancing is something that calls to you, by all means, go for it! But if it doesn’t call to you, there isn’t anything wrong with that.

As well, you might really think you’ll thrive freelancing, but then find that you don’t like it—and that’s ok too! It takes a certain personality type, to be quite honest, and some people are just better at it.

Freelancing isn’t better than being an employee. Different things work for different people and encouraging everyone to freelance or own their own business to the detriment of their personality or stress level is… bad.

2. Being a freelancer uses more energy on a wider variety of things.

Not only was I managing client’s social media and writing a ton of copy week-to-week, I was also acting as an account manager, a bookkeeper, and a project manager. It was way more mental energy every single week and for 75% of those tasks (like organizing my time sheet, invoicing, keeping track of my books, and more) I wasn’t being paid because it wasn’t client work.

Plus, at least 50% of my mental capacity went towards worrying about my taxes.

It was a lot. It was super stressful and I felt like I didn’t know how to handle it. A lot of the information on how to handle these things is, surprise, behind a paywall these days; there is no one giving clear cut, good advice on how to manage that level of stress. It’s understandable, but it makes freelancing as a profession a lot harder for people who might thrive in it. And it makes people like me, who are high stress anyway, more likely to leave freelancing.

3. I actually have more time now.

So it turns out, not working weekends hugely improves my mental health? Not having to wake up at 4am every weekday to get massive amounts of scheduling and invoicing done is a huge stress relief?

And being able to set my hours and say, “I’m gone at 5pm!” is another huge relief?

This is to say: I actually have more free time now than I ever did in the past year of freelancing and that’s really, really exciting.

3 Skills Every Freelancer Needs

Welcome to the Diversifying Your Skills series! Learning new skills in your life and career can be really rewarding—but challenging at the same time. What does it mean to realize you’re missing a skill for your career or, worse, life? How can you best learn new skills? I’ll be answering those questions and more in this weekly series. You can read all posts in this series here.

It’s easy to wax poetic about being a freelancer. There are so many pluses: I can take days off whenever I want*; I can schedule my time however I please*; I can choose what work to take on and what work to pass on*…

What are those asterisks for you ask? Sorry, let me check the footnotes…

* You can take days off, except the days where your clients expect you to be working, especially if they email you, call you, text you, or check in on you.

* You can schedule your time however you want, but you’ll need to factor in when your clients are awake and working as well.

* You can choose what work to take on and what to pass on, but you’ll always have to consider word of mouth and how much money you’re making each month.

So, yes, there are many pluses to working as a freelancer! We don’t often talk about the not-so-fun ones: that it’s easy to say you work for yourself, but you kind of aren’t. It’s more like you’re working for multiple bosses, all with different needs, and schedules, and communication styles.

This isn’t to shit talk freelancing without reason. Some days I love being a freelancer; some days I just wish I had a normal job (like when I wish I had an account manager who could take on all my client meetings!)

One thing that we often don’t talk about with freelancing is that you need more skills than just the ones you’re selling as services. Yes, you’re a good writer, or a good graphic designer, or a good strategist. But are you good at… bookkeeping? Do you have a customer service voice? Let’s chat the 3 skills that every single freelancer needs.

1. Bookkeeping

Here’s an embarrassing story: mid-way through July, I all of a sudden realized I should be paying my estimated taxes into the state and federal government. I sort of abstractly knew this was a “thing”, but for whatever reason thought that my first year of freelancing, I didn’t need to do this. (This is still a bit of a hazy point; lots of accountants say that is the case, but other accountants say it’s not. The government doesn’t really list that… but all I know is, I don’t want to be penalized or investigated for tax fraud. And you probably don’t either, right?)

It goes without saying: you need either to learn bookkeeping now so you have a good record of your invoices (or use a simple invoicing software like Square) or hire a bookkeeper or seek out a bookkeeping software. I recently looked into Bench and while I really like them, I wasn’t quite at the point financially where I needed their help. If I had more clients and more invoices, it would definitely be top of my list.

Right now, I primarily use a combination of spreadsheets, my Square invoices, and Quickbooks. I don’t have a ton of expenses yet, so that’s not a huge concern to me. On top of bookkeeping, having a great accountant who you can call and ask questions is huge.

2. Customer Service

Do you know someone who says stuff like, “I won’t ever have a job where I have to work customer service again”?

I used to say that all the time when I worked retail and food service. I actually really loved working both in retail and food, but the customer service aspect was always challenging for me. I’m not super assertive and especially when I was younger, I struggled to establish boundaries.

That being said, it turns out when you’re a freelancer, you’re every part of the job: client management, customer service, service provider, CEO… everything. It’s all you, baby!

So if you like me said you would “never work customer service again”, I have really bad news for you.

Providing good customer service when selling your services can be really challenging. It’s hard to take feedback, especially if you’re an expert in your field—a client hired you for that reason, so it’s hard to make changes based on their desires. But balancing client requests and your expertise is important and learning to communicate effectively is huge! It’s all about good customer services, uses the right language and tone, and providing a great experience on top of great services.

3. Organization

How organized are you?

On a scale of 1 to 10, how organized is your desk?

More bad news, if you answered “oh shit, I’m not organized at all”, you’ll need to learn some organization techniques soon! You can read my series about getting organized here.

Being organized will make your life so much easier at the start of your freelancing career. Rather than realizing mid-way through the first year that you’ve lost a contract or don’t remember where you put the notes you took at a meeting that you need. Here are a few of my tips:

• Buy a filing cabinet or filing box. Create folders for every client. Any printed contracts or notes go in here. (Create this same system in Google Drive; call it FILING CABINET and create the same folders.)

• Create an tagging system for your email inbox.

• Clean off your desk and keep it clean.

• Keep a notebook for each client. (I buy notebook packs I find on sale at TJ Maxx or Marshalls.) All notes for meetings I keep in this one notebook!

It’s pretty easy to set up a system to start organized now. It doesn’t have to be boring or a huge chore—just something you do to keep yourself organized and sane. I usually set aside a few hours each week to get organized, update my invoices and hours, and make sure all my tasks are organized in Asana.