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.

Where Can I Learn New Skills?

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 past articles in this series here.

In my final article of this series, I want to focus on a specific aspect of diversifying your skills: when you’ve come to the conclusion that you need to learn something new, where do you actually go to learn it?

Primarily, I think most skills are best learned from doing: if you want to learn to be more patient, you simply have to work on it everyday. If you want to learn how to make better graphics on Canva, you should work on making graphics everyday and getting feedback. However, there are some really great places to learn skills that are more high-level. Let’s talk about them!

1. Khan Academy

Khan Academy is a great place for kids to learn extra lessons about math and science. But if you’re an adult, there are some great courses as well for Computer Programming, Economics, History, and more. I love doing Khan Academy courses to brush up on basic skills—prime example, when I was working on my books recently, I did the personal finance lesson to help brush up on some things I forgot. Khan Academy is free for users, which makes it even better.

2. Skillshare

Skillshare is another great option and it has 2 tiers: a Free account, which gives you access to all the Free classes; and a Premium Account, which gives you full access to everything. I have a free account at the moment and I love it—I’ve taken great classes on using my DLSR (something I want to get better at!), marketing, and more. All for free.

However, if you want to upgrade to Premium, it does seem worth it to get access to more classes.

3. Lynda

Lynda is owned by LinkedIn now, which should tell you everything you need to know about it: if you need new skills with a business or tech focus, then Lynda is the place to go. Back in the day (2013, I think), where I worked at the time had a free Lynda membership for employees, so I would spend my days doing courses on Microsoft Word, Excel, everything that employers were suspicious of me having experience in. (Side note: one time an interviewer fully interrogated me about “when” I learned to use Microsoft Excel. Like, 3rd grade computer class? For older people, it seemed bizarre that I just knew how to use Excel because it always existed for me! But I digress.)

Lynda is a paid subscription, but you can get a free month to test it out. A standard plan is $29.99, but if you pay annually, it works out to $19.99.

Should I Outsource or Learn?

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. To read the previous posts in this series, click here.

A few weeks ago, I had a great phone call with a rep from the company, Bench; what they do is basically super easy, efficient bookkeeping for entrepreneurs and small businesses. It’s like Quickbooks, but slightly more millennial (and way easier to use). While I decided to pass on Bench (just for the moment!), it was a conversation I needed to really think about: do I want to learn to do this better (that is, bookkeeping) or do I want to outsource this?

It’s a question for the ages. Even if you’re a regular employee (not a freelancer, solopreneur, or business owner), you’ll eventually have a moment in your career or your life where you have decide if you want to take the time to learn to do something yourself or simply outsource it.

A simpler way to look at it is this: do I want to delegate this task or add it to my plate?

Again, a question for the ages.

This kind of decision making is so common in life; you have to decide how much you want to take on personally, if it’s worth it, if you want to do it, if you can afford to ask someone else to do it.

Here’s the real question though: how can you make the best decision?

When it comes to your career or your life, there is also a benefit to diversifying yourself and letting yourself gain that knowledge. But weighing it against other factors that are just as important is big. In this blog post, let’s talk over some things to think about when it comes to deciding between outsourcing or learning it yourself.

Do you have the time to commit?

Ultimately, one of the biggest decision making factors is time.

Do you have the time to learn this new task?

Are you motivated to learn?

Are you dragging your feet and avoiding it because you have too much on your plate already?

Only you can know if you have enough time to learn a new aspect of your business or career or life. Only you know if you have the time to take it on. If you hate the idea of bookkeeping, or if you simply don’t know when you’ll make the time for it, then outsource it. If you’re already buried beneath work, or if you’re already pretty far ahead in your career, then adding a new skill that might lead to burn out might not be top priority.

A few other time-focused things to consider:

• Is it your busy season? If so, now’s not the time!

• Are you in the middle of a big transition? (Think: new baby, new house, new job, etc.) If so, now’s not the time!

• Are you struggling with your task list already? That’s right; if so, it’s not the time!

Are you outsourcing out of fear?

There is nothing wrong with outsourcing certain tasks. However, ask yourself if you’re outsourcing out of need or fear of learning something new (or because you’re convinced you won’t be good at it/do it well). 

It’s ok to ask for help, but it is important to recognize when we delegate or outsource out of a fear of failure or avoiding something we aren’t sure if we’re good at.

Here’s an example: I hate Facebook ads. Whenever clients ask me to do Facebook ads for them, I outsource this task; I recommend someone else or just ask them not to ask me to do it. I’ve been passed on for other freelancers because of this.

The truth is, I know Facebook ads aren’t that scary. I’ve done them before! It’s not that bad! But I find the process of learning too overwhelming and I fear I won’t be good at it. Managing budgets has never been my strong suit. I know I avoid learning about Facebook ads out of fear of failure. And that’s no good.

It’s my goal in 2021 to take a few courses in Facebook ads and to get better at this aspect of my job.

If you outsource, are you giving that person all the information you need?

This isn’t a time where you get to micromanage someone! I said what I said. If you end up delegating a task, but then you micromanage and obsess over how that person is doing it… listen, maybe it’s you.

When it comes to outsourcing, here are a few things to consider:

• Make it easy for that person to do their job. If you’re hiring them, making sure they have everything they need to be successful is really the bare minimum in terms of your job.

• Don’t be horrible. We’ve all had jobs where we were micromanaged and picked at until we were miserable. If you delegate a task to someone whose job it is to do that task, then they’re an expert. If you’ve spoken to them, vetted them, and learned about them, then you know that. So leave them alone. Let them just do it for you!

Your choice isn’t forever

The most important thing to remember? If you choose to outsource now (your bookkeeping, your taxes, your house cleaning, whatever), it’s not forever. You don’t have to commit to never learning that thing, or never doing that thing again.

You might take it back on when you have more time or after you can take a course. You might give yourself a few years. You might never take it back on. But it’s not a forever thing. You can always change your mind!

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.

3 Tips for Anyone Starting a Business

When I started freelancing over a year ago, I made the decision not based necessarily on desire (although I’d been thinking of going full time freelance for a while), but because it was the only option available to me. I’ve written about falling into freelancing before, so I’ll save you all the details. But one big thing I didn’t realize when I started freelancing was that I was essentially starting a new business, with myself as the CEO.

I didn’t really consider it a business—it was just me! I just needed to work to keep paying my mortgage. I also wasn’t selling anything—just providing services based on my years of agency experience.

The truth is being a freelancer is starting a business. Whether our work resembles a business owner that sells a product isn’t necessarily the point… What is the point is that freelancing, selling products, blogging and making money are all businesses. And if you started one, you’re a business owner.

Here are 3 tips if you want to start a business, are a freelancer floundering with what you need to know about running a business, or are just curious about what running an independent business is like.

1. Speak to Accountant Now (and Create Your Team)

The sooner you talk to an accountant, the better. Why? Because paying taxes as an individual proprietor is confusing at best. If you are starting a business, there is a lot of info you’ll need about collecting and paying taxes, registering your business, and more. An accountant won’t have all the answers, but they will be able to help you find those answers.

This leads me to sort of a second part of this point: create your team for your business.

Even if you don’t have employees quite yet, your team will still consist of people who help you run your business. This might include:

• Your mentors: a group of people you can ask your dumbest questions (like, am I stuck up shit creek without a paddle if I forgot to mail my individual tax estimates??) and get good advice back

• Your accountant

• Your bookkeeper (or your bookkeeping software)

• Your lawyer (if you need one—and you never know if you will need one)

Once you have a few go to people that you can always shoot an email with random questions, you’ll be good to go.

2. Don’t Be Afraid to Try Something New

When I first started freelancing, I had a lot of ideas about what I specifically wanted to do. I wanted to get back into strictly copywriting; I was tired of working in social media.

It should not surprise you that I haven’t landed a single copywriting-only client.

I do a lot of strategy. I do a lot of social media writing and strategizing. I also added a relatively new service for me: VA services. (VA is a virtual assistant.)

A lot of my clients already have either a marketing person or an agency. However, their agency charges too much for them to implement the materials—like scheduling emails or blog posts to go live. So, I take on a lot of the busy work, like scheduling, tracking analytics, and more. This helps small businesses offset the costs of marketing while still getting high level work.

If you’re starting a business, you might find yourself falling into work that you never expected. Maybe you make a product for fun that ends up taking off. (I actually always tell clients about American Eagle’s American Beagle April Fools joke from several years ago—that was so popular that they ended up making a dog line of clothes a real thing!) Don’t be afraid to switch up your services or products based on what ends up selling.

3. Protect Your Time (and Keep Your Boundaries Firm)

I’m big on setting boundaries. And especially when you run your own business, you can very quickly erode your own boundaries. Trust me, I know from experience.

The first 6 months I worked freelance, I didn’t establish boundaries. I answered emails when I got them; I answered texts when I got them. Sometimes, I didn’t raise my head from work for hours. Thankfully, Forrest was in school for that time. But once the pandemic hit, I knew I needed to get my shit together.

I couldn’t be both a mother and a freelancer and not have boundaries.

If you’re a business owner, I recommend my guide to setting boundaries. However, as a short summary, here are 3 boundaries that you need to make sure you have:

• Set your work hours and work days. On this note: Communicate with your team that you understand their boundaries and want to respect them. Make sure you note your team’s working hours and days.

• Create a space that is just for your business. An office, a corner, whatever works.

• Write an FAQ in advance to provide to potential clients and customers so you don’t end up answering the same questions over and over.

Do You Need to Learn New Skills?

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.

When I first started freelancing, I knew there were a few skills I had that set me apart from other freelancers or would simply make me an appealing person to work with. They were the fact that I was organized, knew how to set up and run a project, and was an expert in my field (even if I don’t always feel like an expert in my field). However, there were a few skills that I knew I didn’t have.

That meant I had to learn them.

These skills are important to freelancing, and really to any job, but I just didn’t have them; they included things like networking, bookkeeping, and client management. Learning these huge, new skills took time, effort, and dedication. But I knew I needed them.

As time has passed, I’ve realized that constantly learning new skills, or adjusting what I already know, is a major part of my life and my career. There will always be things we don’t know. But not knowing isn’t an excuse not to learn, not to try, or to give up.

If you’re reading this post, then you’ve probably asked yourself “Do I need to learn new skills right now?” at least once. Let’s break down why learning new skills for our lives or career isn’t a failure, what learning new skills is super valuable, and what else I’ll be covering in this weekly series for September!

What It Means to be a Lifelong Learner

Learning doesn’t stop the moment we turn 18. Or the moment we graduate college. Or when we’re 10+ years into our jobs.

We’re all constantly learning. (And if someone isn’t learning new things every single day, or just refusing to learn new things, well, then, I have some feelings about that and I’m sure you do too.)

On the internet, it feels like everyone is an expert. No one feels like a beginner or someone who is just learning. Influencers position themselves as experts on things (parenting, skincare, home decor), but are they really? You should always question someone who says they are, unequivocally, an expert. Why? Because even experts (and at this point in my career, I’d say I’m expert-level in my knowledge of 2 things: blogging and social media) admit freely that they are learning new things every single day.

Being a lifelong learner means staying curious about things, even unrelated to your career, or hobbies, or life. It means asking questions when people talk to you (because you want to know more and learn!); it means reading articles, seeking out new information, talking to people about solving issues.

Being a lifelong learner doesn’t mean you’re in school all the time; it just means that you’re always trying to improve your knowledge, your outlook, and your life.

The Value in New Skills

When I had my son, I didn’t know how to breastfeed. Even 4 weeks later, visiting a lactation consultant, I realized that part of the reason I never successfully latched my son was because no nurse during our 7-day hospital stay explained to me what I was supposed to be doing. They always just said, “Ok, let’s try to latch him” then just watched my struggle and not know what to do for 20 minutes before sighing and holding out a bottle. (This did wonders for my self esteem!)

There is always something new for us to learn. Something that other people can teach us. When you see someone struggling, there is always a question if you should say something. If you see a new mom struggling to successfully latch her new baby, should you say something? (I’m on the side of YES you absolutely should!) If a new coworker doesn’t know how to use the coffee machine in the break room, should you show them? Yes. If you would want to be taught these things, you should be willing to help others.

Sometimes, learning something new can feel frightening, difficult, or overwhelming. Or sometimes, we end up learning a new skill that invalidates lots of our old ones. (For example, I know Hootsuite like the back of my hand—but because it no longer offers a full suite of scheduling tools to free subscribers, I don’t recommend it or even use it. Working with small businesses has taught me that scheduling tools are far too expensive and it invalidates a lot of my agency-level knowledge.)

Always think of yourself as a lifelong learner, someone seeking value in learning new things; there will probably never be a point in your life where you know everything.

What Comes Next?

So what now?

You know you need to learn new skills—either for your job, or your hobby, or something you want to achieve.

So where do you start?

I’m glad you asked! This month, I’ll be sharing a post every weekend about learning new skills: what skills you need for freelancing, the best places to learn new skills, and much more. I hope you find it valuable! Don’t forget to sign up for my newsletter going out at the end of the month for exclusive content.

3 Tools You Need for Freelancing

Some people choose a freelance career. It becomes the best choice for them. They have time to prepare, to create a workflow, to research and get ready for the path they’ve chosen.

However, some of us don’t quite have that going for us.

Have you ever seen those memes on TikTok about puppy dog eyes girls (I can’t add that emoji to my blog post, but you know what I’m talking about!) versus bruh girls? I feel like those memes could be easily applied to lots of things, but especially to “those who choose freelancing” versus “those who fall into freelancing.”

Those who choose freelancing have a great Instagram aesthetic, great topics for their Reels, and a workflow ready for invoicing, keeping time, charging clients, and more.

Then, there are those who fall into freelancing: crash landing into tax season, knocking over everything in a coffee shop trying to figure out invoicing, late night panics about chasing invoices or getting new clients.

You get the drift.

This blog post is for the people who fell into freelancing—people like me. I haven’t shied away from the fact that freelancing wasn’t really something I chose, but really the only option forward at a certain point. After I got laid off, it felt like I was starting my career all over again. I was exhausted and burnt out and I just plain didn’t know what to do. Freelancing opened up as an option and I went after it—pretty much only because searching for jobs, and the variety of biased rejections I experienced, were soul crushing.

When I started freelancing in earnest, I didn’t have a process. I didn’t know what I needed. And unfortunately, I didn’t have time to do the research I needed to do—I just kind of had to figure it out on the fly.

So, for those currently in the process of freelancing, let me make it easy for you. Here are 3 tools you need no matter what kind of freelance services you offer.

1. Bookkeeping Software

Surprise! You’re now your own bookkeeper and HR person! You’re going to need some kind of bookkeeping system. So far in 2020, I have kept myself afloat using a combination of Square for invoicing and a spreadsheet. I don’t have a ton of expenses—and because 2020 is the way it is, I don’t need to have tracked my mileage at all (because I haven’t driven… anywhere?). However, I already have a bettering bookkeeping system lined up for 2021.

One note here: you should definitely start a separate freelance banking account now. Get all your payments sent and/or deposited into this account; make all your purchases out of this account; and pay yourself out of this account. This will really simplify your life. (Unfortunately for me, right when my freelancing kicked into high gear, banks closed and I couldn’t open a separate bank account until JULY! My books are a mess, send help.)

2. Time Tracking Tool

Clients will often want a breakdown of how you spent your time on a project—even if you’re being paid by the service, not the hour. (Although you will frequently be paid by the hour!) My favorite tool for this is Clockify, which I’ve mentioned before. I like it because it has a Chrome extension where you can start your timer from anywhere. Plus, you can set up multiple projects underneath a client, which is great if you need to invoice differently for certain projects. They recently introduced a Dark Mode and while that’s not my thing, I know for many people, it makes a huge difference for them!

3. Email Marketing

You’ll probably need to send emails to clients in some form, especially as you get more clients. If you have a website and start marketing, it’s good to have your email marketing plan set up now, rather than later.

I have used all of the email marketing tools out there but my favorite is Flodesk. The only downside to Flodesk is that there is no free level—it’s only paid. However, most people have sign up codes to use to get it for 50% off for life. (That’s a pretty good deal.) The templates are gorgeous. Plus, it’s the same price for however many email addresses you end up having—whether is 100 or 100,000. In comparison, MailerLite and Mailchimp charge over a certain number of subscribers and emails sent per month. You can sign up here and get 50% off.

A Complete Guide to Setting Boundaries

This month, we’re going to talk about establishing boundaries: in your business, in your personal relationships, and beyond. Establishing boundaries is so important to everyone and something we don’t talk about enough! I hope you find value and comfort in these blog posts. You can read all posts in this series by clicking here.

This week, I’m finally ready to post my full guide to setting boundaries. This guide will cover everything you need to know about setting boundaries: what that means, how to do it, what to say, and how to keep yourself from letting boundaries lapse.

Boundaries are one of the best things you can do to keep your relationships—from work to home—emotionally healthy, as well as to improve your own mental health. There are tons of benefits to setting boundaries—you can read the pull quote below, but here’s a rundown:

• Setting boundaries reduces your stress, as well as your mental load. If you aren’t having to constantly balance the emotional needs of other people, or be on call to everyone at the same time, then you will experience way less stress.

• If you have children, setting healthy, respectful boundaries teaches them to do the same thing: to set healthy, respectful boundaries, to respect themselves, and to prioritize their mental health.

• Setting boundaries help define the line between your work life and your home life.

I’m glad you’re here and reading my guide to setting boundaries. As I’ve said in previous posts in this series, I’m not a mental health professional—just one person who loves to write and who attends therapy to help set boundaries in my professional and personal life! I hope you find this guide helpful.

How to Set Boundaries

What does it mean to set boundaries?

Good question! Here’s an example to help illustrate what that means.

Let’s say you are a mom of 2. Your children’s ages are 3 and 1. Both are walking, but only one is verbal at this time. They have a bad habit of always following you into the bathroom no matter what. You wish they wouldn’t, but if you close the door, the one-year-old throws a fit and the 3-year-old joins in.

What is a boundary to set in this example?

1. Establishing with the 3-year-old in age appropriate language that you want to be alone in the bathroom. Bathroom time is private time.

2. Remind yourself that you deserve private time. Again, bathroom time is private time and you get to decide if you want your children in the bathroom with you or not.

3. Encourage the 3-year-old to entertain the 1-year-old when you’re in the bathroom. “It upsets [baby] when I go to the bathroom. But bathroom time is private time. If she gets upset, can you comfort her for me? You’re so helpful! When I’m done, we can all bake cookies together.”

Firstly, the boundary is defined: you want to go to the bathroom alone and you have that right, even from your children.

Secondly, the boundary is communicated: from now on, you’ll be going to the bathroom alone and closing the door. There will be consequences if they open it.

Thirdly, acknowledge their emotions. “I know it’s upsetting with Mama goes to the bathroom alone. I love that you want to spend time with me. But bathroom time is private time.”

Lastly, you keep the boundary. When you go to the bathroom, you close the door and you don’t let your children sit at your feet.

That’s just one example of setting a boundary! But here’s a rough outline of those steps again:

1. Define the boundary and why it is important to you.

2. Communicate the boundary.

3. Acknowledge the needs of others.

4. Keep the boundary established (even when it’s challenging).

The last steps is admittedly the hardest one. How can you stick to your boundaries when you have a child crying outside the bathroom door? Or when a client calls you over and over on a Saturday afternoon? Or when your boss asks you to please respond to emails after 7pm? Where do you draw the line? Let’s talk about sticking with our boundaries—that will make up the majority of this guide!

---

How to Stick to Your Boundaries

Enforcing Boundaries with Love and Kindness

First things first, let’s remember why we’re setting boundaries in the first place.

In the example I provided, we aren’t setting a boundary with our children to be alone int he bathroom because we don’t like our kids. We want and deserve a few minutes alone; and we want to make sure our children understand that bathroom time is private time.

Boundaries are created out of love and a desire to be better--not a desire to hurt other people.

Setting boundaries doesn’t mean we don’t love the people around us, that we don’t like them, or that we don’t respect them. You can set boundaries and show love and kindness while doing so!

All that being said: sometimes, our boundaries aren’t respected. This doesn’t happen out of unkindness, usually. It just means that perhaps they don’t understand the boundary, they don’t understand why it’s important, or they don’t realize that what they’re doing is crossing the boundary. However, sometimes people do it, plain and simple, because they don’t feel like respecting your boundaries—which means they don’t really care about respecting you. In this case, the only advice I have is this: it’s not your job to make it easier for them to do this!

Enforcing boundaries with love and kindness will look different for everyone. However, here are a few example phrases I keep in my arsenal:

• “Do you remember when we talked about appropriate times to text me? It was a few weeks ago, so I just want to circle back to that and remind you that my working hours are…”

• "Last time we spoke, I mentioned that I do try to get to emails within 24-48 hours. A few days ago, you emailed me 3 times in 2 hours. I get that sometimes things happen, but due to the volume of my inbox, I have to ask you to please not do that. I appreciate you as a client and this project is so fun, but that does get overwhelming for me.”

• “I’m so excited to bake cookies with you later. But for now, I need to work. I’ve put the red light sign on my door. Do you remember what that means?”

Keep gently reinforcing boundaries! You don’t have to be rude (or feel rude!) when you do it.

---

Communicating Boundaries Respectfully

When we set boundaries, we want to make sure that not only are we communicating our boundaries, but also acknowledging the feelings of others as we do so. This might mean:

• Reminding our children that we love them and respect them and that, when we’re doing with xyz, we’ll do something fun together.

• Reminding our clients how much we appreciate their work.

• Reminding our friends and family that we appreciate them and love them.

Communicating boundaries respectfully also means acknowledging the boundaries and feelings over others. This might mean having longer discussions about our boundaries, how we communicate best, and how we don’t want to be spoken to. This is great for extremely close relationships, like your partner, siblings, parents, or others.

However, for clients, this is definitely more complicated.

Sometimes as freelance workers, we can feel not like we are a boss, but rather like we have multiple bosses. With all my clients, I try to reiterate one small fact: I am a freelancer, not an employee; as such, I am not beholden to rules of an employer like an employee would be. I set my working hours; I set my response times; and it is up to me set those expectations from the beginning. Those expectations are ultimately boundaries and if a client repeatedly pushes on them, the boundary needs to be established even more—and reinforced, as we’ve discussed. That being said, this is a relationship that is often much more fraught, because it is almost entirely without emotion.

Our work boundaries are often more challenging to communicate than our personal life boundaries—and that’s ok. Here are a few great things to say:

• “Hi there! I’m sorry if you expected a reply to this when you sent it. For the sake of my mental health and to allow myself to be the best employee, I do not respond to work emails or questions after 6pm. I try to get to these emails and texts first thing when I start my work day though.”

• “I noticed that you have been texting me after 6pm a lot recently. Here is how I prioritize my work. Would that help you better understand why I’m not getting to things at a certain time?”

• “Would it be helpful to schedule a weekly check in time so that we can handle all of these concerns at once? Maybe that will reduce both of our inboxes!”

This is definitely challenging work, but it is valuable. The more you communicate your boundaries, and reinforce them, the easier it will get.

How to Respond to Gaslighting

Setting boundaries is where we are all most likely to experience gaslighting, unfortunately. In this case, I want to the Mindgeek on Instagram, who has tons of resources to responding to gaslighting behavior.

View this post on Instagram

A post shared by Sarah Crosby (@themindgeek) on Aug 21, 2020 at 11:27am PDT

Here are a few examples of gaslighting in response to setting boundaries:

• “I don’t remember you saying that” or “that’s not what you said!” when you remind them of your boundaries.

• “It’s not that bad”

• “You’re just being dramatic.”

If you experience these things, the only thing I can offer is sympathy; know that I understand, your boundaries are valuable and important; and that you know your truth more than anyone else. The Mindgeek’s tips are good ones.

---

How to Move Forward

Where do I go from here?

You set the boundary; you communicated it; you’ve been working on enforcing it… what happens now?

The thing about setting boundaries is this isn’t one-and-done work. It requires constant checking in and re-establishing. It can feel overwhelming to think of this work as being one that never ends. But instead of thinking of it as endless (“oh my god, I have to keep reminding my kids to do xyz everyday—this is the worst”), think of it as an opportunity: “each time I remind my kids of xyz, I get another opportunity to teach them to prioritize their mental health and relationships.”

Working on ourselves and our mental health isn’t ever going to be a one-and-done process. Don’t I wish it was! That being said, looking at things as opportunities to grow and change, to experience something new, to work on being our best selves is much, much better than thinking of it merely as endless, slogging work.

I hope you found this guide to setting boundaries helpful. Thanks for reading, as always!