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27 Things I Wish I Knew Before Becoming Self-Employed

I’ve been self-employed, running my freelance graphic design business full time for almost 7 years now. It has been one of the greatest decisions I’ve made, but also came along with lots of struggles. If you’re considering quitting your “real job” to follow your dream of running your own business, make sure to consider the following 27 things I wish I knew before becoming self-employed.

1. Friends and family always think you’re available

Even though working from home is becoming way more popular than it used to be, not everyone understands what being self-employed means. Friends and family may assume you’re aways available to hang out or meet up for lunch. Sometimes when I say, “Sorry, I have to work today,” it’s met with the response of “…but you’re you’re own boss, can’t you just do it later?” They may not realize there are deadlines and conference calls and plenty of other obligations that must happen during everyone else’s working hours.

2. You will spend way more time working than you think

A lot of people think if you don’t have a boss telling you what to do, you don’t need to work as much. However, that could not be farthest from the truth. In many cases, you’re starting your business from scratch. It takes a HUGE amount of time to establish yourself and build up reliable clientele. Thankfully I’m in a place now where I cut my hours down significantly, but for the first few years I was absolutely putting in 12+ hour days sometimes 6-7 days a week. Now, I admit I may be a bit of a workaholic, but don’t think just because you work for yourself that it means less time on the job. At least not right away!

3. Setting aside money for taxes

This is a big one! When you work for a company, you receive a paycheck with your taxes already taken out. When you’re self employed, you’re responsible for this payment yourself. Don’t forget to set aside a percentage of your earned income every month to ensure that you have enough to pay estimated taxes each quarter. Unfortunately, you’ll be writing a large check all at once, instead of having a little taken from your paycheck every week. This can be pretty jarring at first, but if you set aside enough for it, it won’t hurt at much.

4. Unpredictable workload

Depending on your field of business, certain times of year may be busier than others. While this is common in large companies as well, it can be stressful when you’re the only employee. Sometimes I find it hard to schedule my client work because one day I may have only a few projects to get done and the next day I might have a request for 5 urgent deadlines. It can be difficult to make sure everything gets done without any coworkers to rely on when things get busy.


5. Managing multiple clients/customers at once

This is something I’ve definitely struggled with a lot in the beginning of my career. Remember how when you were in school, all your teachers would assign you homework and tests seemingly all at once? They weren’t aware that your other teachers gave you a large workload that week as well. It’s very similar to having multiple clients. Everyone wants their project completed first or their order sent out ASAP. It can be difficult to manage multiple clients at once, instead of having one boss who may be more aware of how much work you currently have on your plate. In addition to this, at least in the graphic design field, it can be hard to switch back and forth between different clients. You might be working on one project in a certain style for a time, and then needing to work on something for a different client who requires a completely different aesthetic.

6. Dealing with criticism

When you work for a larger company, and a client or customer complains, it’s typically not completely your responsibility. When you’re self employed, every complaint and criticism usually falls back on you. It can be difficult not to take every negative interaction personally. When I send a client a design and receive negative feedback, I used to get very upset about it. But what I’ve come to realize is that it’s not possible to make everyone happy 100% of the time, you’ll just have to build up a thick skin and learn to not take everything too personally.

7. Some people don’t think you have a “real job”

Like I mentioned earlier, self-employment and working from home is becoming much more common nowadays. However, not everyone understands what you do all day. Some people may think that if you don’t have a 9-5 job you go to everyday, that you’re sitting home in pajamas. (Well, maybe you are in pajamas most of the time – I sure am! But that doesn’t mean you’re not working hard on your business).

8. Working with clients in other countries/timezones can be challenging

One of the cool things about working from home is that you can work with clients from all over the world without leaving your house. The downside to this is that not everyone is in the same time zone or recognizes the same holidays. You might be getting ready to end your work day while your client is just beginning theirs. Sometimes it can be hard to coordinate schedules and get everyone on the same page. Another thing to consider is holidays. One year, I forgot to put up an autoresponder email that I would be out of the office on the 4th of July. One of my international clients called me with an urgent project because they weren’t aware that it was a large holiday in the U.S.

9. You don’t have a set schedule

When you work a typical job, for the most part, you know when you’re expected in the office and when it’s time to leave for the day. Working from home means you don’t necessarily have a set schedule. As long as you get your work done, you can usually do it at any time of day or night. While this can be very freeing, it can also be difficult for those who need structure and have a hard time getting going in the morning.

10. No benefits/health insurance

This is definitely something you need to seriously think about before becoming self-employed. When you work for yourself that means you’re also responsible for providing your own insurance and benefits. Paying for insurance yourself can be very costly. If your spouse’s employer covers you and the children then that is definitely something to take advantage of. Not having benefits also means if you’re not working, you’re not getting paid. That means no paid sick days and no paid vacation.

working from home

11. Things like buying a house may be more difficult

When it’s time to do things like getting a mortgage, it may be more difficult if you’re self-employed. Banks may like to see a steady paycheck to believe that you will be able to make your payments on time. You may have to show plenty of records proving you have a reliable income.

12. No job security

One difficult reality about becoming self-employed is that there is no real job security. If you don’t have work, you don’t get paid. And while you can’t necessarily get fired, there is no guarantee that you’ll be making a livable income every month. Some may find this unpredictability exciting, and others may find it a bit scary never really knowing if you’ll bring home a paycheck.

13. Income can be unstable

Some months your business may be doing great and you’re raking in the dough. Other months can be slow and you may wonder if becoming self-employed was the right decision for you. Ups and downs are usually normal, but the downside of running your own business is that you don’t get a steady paycheck that you can rely on every week. The upside to this is that your income potential is unlimited!

14. Friends may try to get things for free

This may not apply to every type of business but I’ve definitely found that some people may expect you to do work for free because it’s your own company. They probably wouldn’t expect your boss at a big company to give away free stuff or services, but since you are the boss they may feel as if it’s not a big deal and you’re just helping out a friend. You’ll need to get good at setting boundaries and saying no often!

15. Work/life balance can be nonexistent

When you work from home, it can be really difficult to turn off work mode and go into home mode. Even if you have an office, it’s likely just another room in your house. I always find it super hard to stop working for the night because my laptop is always right there and there’s really nothing stopping me checking my email just one last time to see if anything important came in. It’s very necessary though to create some kind of work hours so that when 6pm (or whatever time you choose!) hits, you know it’s time to put the work away and spend time with family or anything else you enjoy doing aside from your business.

16. Working alone can be… lonely

You might think getting away from the office gossip is a benefit of working from home. But it can also get
pretty lonely not having any coworkers to talk to or commiserate with all day. Most of my work interactions are solely through email. While it can be nice to not have to deal with the office environment, it can also be hard to lose the social aspect of the workplace.

17. You don’t have anyone to push you to be productive

At a typical job, you probably have a boss or manager giving you tasks throughout the day, or checking up on your productivity. When you’re self-employed, all of that falls on you. How much or how little you do with your time is completely your responsibility. If you don’t have the discipline to get yourself up and working every day, it may be hard to lose that external push to be productive. Check out this post from TwinsMommy to learn more about multiplying  your productivity when you work from home.

18. Being self-employed with kids isn’t as easy as you think

I always hear moms saying that they would love to work from home so they can be with their kids all day. While this is definitely a priceless opportunity, keep in mind that it’s not as easy as it sounds. Before my son was born I was working more than full time hours. I thought that once he was here he would sit and play and let me get some work done during the day. This could not be farther from reality! Trying to be productive with a toddler on your lap, banging on your computer, pulling you in every direction and being VERY loud, is not easy! I get my design projects done mostly during nap time, or for a few hours after he’s in bed. That being said, I wouldn’t trade my work situation for the world. But something to keep in mind is that you probably won’t be able to work during the day nearly as much as you may think.

19. Knowing when it’s time to change course

I wasn’t sure exactly how to title this one, but what I’m basically trying to say is that it’s up to you to know when you’re business isn’t working out. This by no means means to quit though! Sometimes what you originally set out to do just isn’t the right fit for you. Here’s an example: During my first year in business I did everything from web design, to coding, marketing, graphic design and copywriting. I tried to do it all and it just wasn’t working out. Eventually I came to realize that my real passion was graphic design and I completely cut (or found referrals for) the other services. It can be hard to change up the business plan you believed in so much. But it’s usually all for the better! Click here to read about the benefit of finding your niche in business.

20. You wear multiple hats

Not only are you the employee, but you’re the boss, the bookkeeper, marketing team and complaint department. You may think becoming self-employed only means doing the work you love and probably left your “real job” for. But keep in mind that there are a lot of other aspects that go into running a business and unfortunately not all of them can be fun.

21. Getting everyone in your house to give you time and space to work

This is a tough one! I have to say my husband has gotten A LOT better about recognizing when I’m in work-mode. But in the early days, it was a hard to say no when he wanted to go out in the middle of the day or kept coming into my office in talk. While it’s great to have the company, sometimes you just have to get your work done, and that might mean telling your family that while you’re in your home office to treat it like you’re out of the house.

22. Learning how to say no and stick to boundaries

Setting boundaries and learning how to say no is something you’ll have to be very skilled at. There will be some projects you may not want to take on, or may not have the time or experience to do. Instead of saying yes to every job offer that comes your way, you’ll have to learn how to pick and choose what you’re able to do. There will also be clients and customers that will expect too much out of you. Don’t be afraid to set boundaries and stick to them.

23. Making time for other things

One thing I’ve always been known for is saying “…but I have so much work to do!” When you work from home it can be SO hard to put the computer down and do something, anything other than work. Lately I’ve been trying to schedule in a workout every day. Instead of telling myself I could be getting work done instead, I try and think of the benefits of taking a break and letting my mind relax for a bit. Making time for other activities is crucial to successfully being self-employed.

24. Chasing down invoices

When you work for someone else, you can expect a paycheck on a reliable schedule. When you’re self-employed you have to chase down those invoices yourself. I’ve found that most clients pay in a reasonable amount of time. However, in some cases, you need to follow up multiple times in order to get paid.

25. Some clients expect you to be available 24/7

This goes along with setting boundaries. When you’re self-employed and working from home, some clients will assume this means that you are always available and at your desk. It may be helpful to come up with office hours for yourself and make sure everyone is aware that you won’t be available after (or before!) your set hours.

26. Getting dressed in the morning can be a challenge

This blog is called Pjs and Paint for a reason. 9/10 times you will find me working in pajamas. However, one thing I’m definitely working on is trying to get dressed first thing in the morning. Something about getting out of pajamas and into regular clothes puts you in a more productive mood and you’re less likely to be tempted into sitting on the couch procrastinating your work. It’s not easy to resist temptation to not get dressed, but give it a try and see if it makes a difference in your day!

27. Dealing with unexpected expenses

Budgeting for unexpected expenses is definitely something to keep in mind. When you’re working for someone else and your desk chair breaks, or your computer stops working, it’s typically not your responsibility to get things fixed or replaced. When you work for yourself and your laptop dies, it’s up to you to cover the cost of repairing it or buying a new one. These costs can add up quickly so be sure to have excess money in your business account to pay for the unexpected.

With all this being said, I wouldn’t trade being self-employed for the world. It’s been an amazing opportunity and I’m learning new things every day. Stay tuned for a more positive post on what I LOVE about working from home and also ways I’ve learned to deal with these 27 struggles listed above.


Wednesday 6th of November 2019

Yes my daughter realized most of this and had to go back into the work force.

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