I left my full-time office job in January 2013 to pursue self-employment. You can read more about my freelance business here if you’re interested in learning more about what I do. It has been a wild ride filled with many ups and downs, and I have learned many valuable lessons along the way.
I think most people envision self-employment as being the holy grail of work. It is perceived as being the ultimate freedom in choosing to use your time as you please and doing what you want to do, when you want to do it.
While there is definitely a lot of flexibility and benefits that come with being self-employed, it is by no means a perfect situation. Like anything, it has its faults.
I know that many of you may be wishing to start out on your own endeavor in being self-employed (that includes if you’re thinking about starting your own blog), and I wanted to share some of the truths I’ve learned that are often looked over when most people talk about their experience with self-employment and what it’s meant for them and their life.
I hope you find this insight into what self-employment is truly like helpful, and that it gives you some additional information to help you determine if self-employment is the right path for you.
7 truths about self-employment:
1. There are no paid vacation days or the option to take a “real” vacation
Often with full-time office jobs, you might have 2-3 weeks of paid vacation time to take throughout the year. Time to unplug and completely forget about work and recharge your batteries for a bit. With self-employment, you get zero paid vacation days. That’s right – zip. zilch. nada. So any vacations you do plan to take will come directly out of your potential income made for those days.
On top of that, you can never completely disconnect while on vacation. Or at least I have found that to be the case for myself and my business. I always need to bring my laptop on any trips we take and make sure there is sufficient wifi as well. Problems could easily arise with the work you do for your clients, and not being connected and knowing what’s going on can mean dissatisfied clients and losing out on opportunities for future work.
The bonus is that I really do love what I do, so this is absolutely not the worst thing in the world. It’s just something to keep in mind when deciding if self-employment is going to be the right choice for you.
2. There are no benefits
As in no health insurance, no life insurance, and no 401K or any of the other benefits that full-time office jobs typically offer. This isn’t a huge problem for me because I am able to get fantastic health insurance through my husband, but I would have to pay a significant amount of money out of pocket for my own insurance if that wasn’t the case.
3. Friends and family may not take the work you do seriously
I’m fortunate that my Mom is self-employed and both of my parents actually have worked from home for years and years before I took the plunge myself, so my immediate family totally gets it when it comes to working from home. But I think many people have the mentality that it “must be nice” to be a work-from-home Mom and likely envision me sitting on the couch eating doritos while playing around on my laptop all day.
Sometimes if friends have a day off of work, they can’t understand why I am unable to meet up for lunch or grab an afternoon coffee. While there are times that I do have the ability to move my schedule around to be able to do some of those things, I am still tied down by calls/meetings and deadlines that need to be met. It can be difficult to convey that to someone who just doesn’t understand.
4. You may begin to dread tax time
While most people look forward to tax season and getting a large amount of money back, it is a time that the self-employed absolutely dread. On top of having to spend a lot of time just preparing everything to be submitted, you typically end up owing rather than getting any money back. Tax time becomes a lot less “fun” when you have to pay thousands of dollars rather than get that amount back like most full-time, salaried workers do.
5. You are 100% in control of your income
While many people see this as a positive (I am one of them), it can actually be quite frightening. If you don’t manage to find or create work to do that brings money in, you aren’t going to be bringing in any kind of income. You can actually spend dozens of hours applying for freelance jobs or trying to find clients with zero success, and therefore $0 made.
You truly have to hustle to be successful when you are self-employed. Opportunities to make money won’t coming knocking on your door, you have to hunt them down. If you don’t have massive amounts of self-discipline, drive, and passion for what you do, I will be honest in saying that I don’t think self-employment is for you.
6. There are intense ups and downs
Just as soon as you find yourself feeling awesome from landing a huge client or completing a big project, you can instantly be brought down by the fact that someone else isn’t going to be able to pay you on time for work you already completed or the realization that you will need to “break up” with another client whose personality isn’t meshing well with yours.
Making difficult decisions or having to face uncomfortable situations is just part of the territory with self-employment. If you don’t think you have the guts to approach situations where you have to “fire” a client or demand that you be paid when someone is withholding payment for work you already completed, you might not be cut out for starting your own business.
7. I wouldn’t trade it for the world
Clearly, self-employment isn’t perfect. But then again, nothing in life ever really is. Despite all of the flaws that come with being self-employed, I still love working for myself and wouldn’t trade it for anything. It’s given me the opportunity to earn a part-time income while being a stay-at-home Mom, and will also give me the opportunity to continue working from home while growing my business and increasing my income once my kids are all in school full-time.
Are you considering self-employment? Did any of these truths open your eyes to the reality of being self-employed?
I’m glad you put some balance into this often fairy tale world. When I started freelancing I imagined it would be easy to set my own hours and take on as much or as little work as I wanted. I found that the world was a lot less flexible (and more time consuming) than I had imagined!
Sick baby? Tough! Previously committed to deadlines must be met!!
Hi Christina!! How are you?! Loved this post and I agree 100%!! I’m in a “down” right now because we took a 9-day vacation to AZ and I asked for time off from all of my clients. I’m back at it now, but it’s tough getting back into the swing of things. I could have worked while on vacation, but it’s SO hard for me to focus when I’m not in my environment (ie my home), which is a huge downside. I wish I could work from a hotel room or from a different location, but I really just do my best work when I’m here at home.
What does your mom do for self-employment or from home?! That’s awesome and it must have been a great example to you to see that she prioritized her kids and her work! I’m hoping to show my girls that and I think that’s a HUGE benefit of working from home — they’ll SEE that I work everyday and that I work hard!
Anyways, it’s great to be back!! I should be back to blogging soon haha. So hard to get back into the swing of things!! Hope you are doing well! 🙂
Yay, you’re back Sarah! I’ve missed you and your posts!!
My Mom is an attorney with her own solo practice now, she’s a pretty bad ass lady hah. I agree, I think it’s so beneficial for kids to see that too!
#3 is the worst for me! Trying to convince my mother-in-law that my photography business was a real business and not a hobby was like trying to get my 4 year old to understand algebra. I was making more money doing that than working in my corporate job, but short of showing her my tax return she just didn’t get it! Ahhh!!!!
I agree with every one of these points. I am very lucky to have access to healthcare through the military since my husband is in the reserves. Tax time does terrify me though!
I’m still getting used to being self-employed. While it’s definitely an adjustment, I’m so much happier than when I had a traditional 9-to-5 job! Now if only I could get up early every day…
It really is quite the adjustment at first! Haha I go through phases of being good at waking up early, and then go back to “sleeping in”. Sometimes I find myself a lot more productive when I’m more well rested anyway 🙂
I especially agree with your first point. When you are an employee, you can forget about work after 5 p.m. You can truly enjoy a vacation and totally forget about your worries at the office.
But when you are self employed or own a business, your mind is always on your business even if you’re not actually working. It’s really tough to take a real mental break and unwind.
Personally I work 7 days a week from morning to night. The only real breaks I take are when I work out or go out (on the occasion). Other than that I’m probably reading emails before I even crawl out of bed and am fully awake.
I’m so glad you shared this! I’ve been thinking about this a LOT lately…it’s nice to be brought back down to reality about what it’s really like. I’m currently employed, but I work in an industry where I am attached to my phone 24/7 – work doesn’t necessarily stop after office hours or when I’m on vacation, so I totally know what that’s like. It would just be nice to eventually do it for myself instead of someone else! haha! You’re right, though, as an employee at a company, I do look forward to tax season!
Good lowdown on the ups and downs of self-employment. My hubby had his own hvac biz for a lot of years. Your points were excellent. It’s good to know what you’re getting into before taking the leap. I’m so glad you’re happy and it’s working out so well for you and your family. 🙂
I only side hustle so I have never tasted full-time self-employment, but many of the things you listed are things I’ve thought about. It would be very difficult for me to give up my job for self-employment at this stage of my life because I would miss the consistent pay, PTO days, stock purchase plan, etc. But both have pros and cons, that’s for sure.
Number 8 might be that you enjoy self-employment so much that you let the housework and laundry pile up;0) Lol!
Seriously though, you have done so well and seem very content!
I would just love to be self employed. Like DC, I’ve done all the side hustling on top of my full time job, but never have been 100% self employed. My biggest issue is I want to go back to working from home. I’ve always telecommuted, but got an office job last year and I can’t handle it! I am gone so long each day. Good for you for working from home! I don’t think I would care about people taking me seriously, but the taxes would totally stress me out.
I do, in fact, dread tax time. Between FICA and quarterlies… blech. But then it’s over and I wonder why it felt like such a big deal.
I do wish I had paid vacation days, though. My husband wants to travel more, and I just look at the subtraction to our income.
I’m currently doing a balancing act between self employment as a side hustle and full time employment so I notice a ton of differences first hand. I agree that it’s super hard to unplug and actually take time off when you’re self employed. This is why if I ever want a day off where I don’t do anything related to freelancing I have to work ahead. Tax time kind of frightens me because next year will be my first year filing self employment income and I’m so used to getting a refund so I don’t know how it’s going to work out. I will probably need some professional help because I’m almost positive I can write off a bunch of expenses and even things out but we will see.
The idea of being completely self-employed (instead of doing both like I do) is so intimidating! I think the biggest thing is paying taxes and realizing that all of that money you thought you earned is gone – poof!
Everything you’ve said here is true! I don’t mind any of it since I am earning considerably more now. As far as vacations go, I just “work ahead” as much as I can so I can take a week off. I still check email every day, but this strategy allows me to take a few real vacations each year.
My husband is self-employed, and I could relate to so much of this. #1 and #6 especially. Ever since he became self-employed, my husband has always brought his laptop with him even for week-end visits with extended family. And ups and downs? We’ve learned to take them in stride, but they were a little too intense for me at first. I’m glad you’ve been able to rise to the challenges you’ve listed : )
I know self employment is definitely not for me! Haha. Even when I work my normal job from home, I find it so hard to disconnect. Why stop working when you could be earning more money? I know if I were self employed that would be a really hard balance for me to find. I think I might just never turn off, and that is certainly not healthy!
Haha that’s very true, I had a problem with that for quite some time as well. But feel like I’ve finally found the necessary balance 🙂
This is my 2nd attempt at being self employed. I’m finding people are warming to this time around much better. Ever since I was a kid, I’ve always wanted to run my own business. I’d spend all my free time setting up a supermarket in the garage, or an accounting business in my bedroom. I’ve played with many ideas on what I wanted to do but nothing really stuck until now.
For me, #1 would be the most challenging. Not impossible but I don’t want to risk burn out either. It’s just getting the business to a place where I can outsource comfortably and have solid processes in place to do so.
That is awesome that you are giving it another go Lisa! I wish you the best of luck in your dream of being self-employed 🙂 You got this!!
To add to your list: when you’re self employed (in the beginning @ least or if you aren’t lucky enough to have a friend or spouse on the ride with you) you don’t have any real assistance.
In most jobs you have an assistant or you yourself are the assistant and therefore you’re part of a team . . .
When you’re self employed an “Yourself” is the only self it can get quite overwhelming because it is just you and you need to be constantly vigilant of making sure you are using your limited time in the most efficient way.
It’s tough.
Absolutely Karen! While my hubby is a great emotional support in so many ways, I don’t have him assist me with my business itself at all. It can be tough to make sure I’m working smart and making the most of the time I have!
The no retirement thing is what gets me. I currently work a full-time day job, and I freelance on the side. I would love to be my own boss, work when I want, but freelancing doesn’t seem to be worth it in the long run if you don’t have a partner to support you with a 401K and health benefits. I’m sure there’s ways to save money for retirement, but with an unsteady income, I would assume it’s a big challenge. If anyone has any tips on saving for retirement without support from a spouse, I’d love to know!
Oh man….does this ever ring true. Even after almost 8 years of being self-employed (initially with wife and 3 kids, then shortly after starting the journey, 4 kids!)
Worth it? Absolutely. Hard? Yes, and often.
Oh wow Scott, that is very impressive! My husband and I are considering the idea of having 4 kids someday (just have one now), so that’s pretty awesome to me that you are juggling so much with that many kids. You must be a productivity rock star! 🙂 I completely agree, self-employment is by no means an “easy” route, but the reward definitely outweighs the tough parts.