10 Lessons Learned in 10 Years of Self-Employment

When I started designing blogs back in 2007, it wasn’t my intention to work for myself full-time. There was so much I didn’t know about managing clients, time, a company, and finances.

I knew nothing.

I launched a blog and then graphic design business 10 years ago then The Everygirl 5 years later. It’s been the ultimate learning experience full of endless change and  “I have no idea what I’m doing” moments. I went from working solo out of my bedroom to having a business partner and full-time team of 5.

People always had this idea that my day-to-day life looked a lot like it does in the photo above. And sometimes, instagram makes it look that way but it’s really not the case at all. But that’s my love/hate relationship with instagram and blogging. We get this glimpse into people’s lives and think we know them, but at the end of the day, it isn’t the whole picture. There’s so much behind the scenes that isn’t nearly as fun, exciting, or glamorous as it might seem. But seriously…does it seem glamorous?

Here are 10 lessons I’ve learned in 10 years of self-employment.

People might not take you seriously

This was a lot more prevalent when I ran a business designing blogs from my living room. People were always commenting on how nice it must be to be able to sleep in and do whatever I want. Hours can be shifted but when work has to get done and you’re the one doing it, you can’t just do whatever you want.

Come up with rules and a routine

Set some day-to-day ground rules that will help you be your most productive self. Pay attention to when and how you do your best work, know when you need a break, and figure out a routine that works for you. I lose focus sitting at a desk all day and usually need a little break in order to do my best work. If you know that by stepping away you’ll do better work when you return, do that, but don’t use that as an excuse to be lazy. It’s a fine line and it’s up to you to set the guidelines.

My desk was in the living room of my first 3 Chicago apartments and I developed a horrible habit of never fully walking away from work. Find a designated office space and core(ish) work hours. Force yourself to leave at the end of the day, even if it’s just for a few hours. It’s so important to check out.

You can work too hard

I’m speaking from experience on this one. My first few years designing blogs, I never felt like I could say no and had a pretty consistent wait list, which was both a blessing and a curse because I just didn’t stop, and designed an average of 5-8 blogs per week. Five days of CrossFit a week and working until 2AM eventually broke me and I got shingles.

There are those points at the beginning where you might not be able to say no, so if that’s the case, be sure to set timelines that will allow you to take a little break. I also made the mistake of needing to reply to every single email immediately until a friend realized I always replied right away, and told me to slow down.

Waiting a few hours is ok. You’re not a machine.

Stop comparing

It was always so easy to look at other designers who were so much “better” than I was or sites with a larger audience than The Everygirl. Someone will always be bigger and better but no business is perfect, and you’re running your business because it’s yours. Stop playing the comparison game and start believing in yourself.

Find a network of people who get you

Find friends who work for themselves by going to a co-working space, coffee shop, or via social media. Having people to co-work and share stories with, and people who get you when no one else does is so important. I personally loved working solo and still love the days I spend on my own, but it can be lonely for some. Most important, having someone to talk to who understands what your going through can be a life-changer when you’re feeling stuck.

Say goodbye to real vacations

I just talked about rules and routines and you can totally 100% sign off if that’s your thing, but I don’t think I’ve left town and not checked email in the past decade. I also didn’t travel until about 2 years ago because I could never really take the time away and was always so stressed out about finances, but that’s a whole other issue.

If you’re running a business solo, you can let clients know you’ll be away and can set up an OOO notification, but ultimately, it’s up to you to decide if it’s worth it. Now that we have a team, I can sign off, but I would rather stay on top of email and return to 8 unread emails vs. completely check out and come home to a bomb that went off in my inbox. But that’s just me.

Money sucks

When you’re ready start a business account and pay yourself a salary if you’re able to do so. This will help you set a budget, save for taxes, and will generally give you your own identity separate from your company. We obviously have this for The Everygirl but I do not for my blog since it’s just something I do on the side.

I didn’t put a percentage away for taxes and didn’t pay my quarterlies. I always just had a little money set aside for when I might need it but there was zero reason behind how much. Then my old accountant (we parted ways immediately after this happened) was “off” on what I owed by a few thousand dollars. I found this out the day taxes were due, so let’s just say that week was the absolute worst. Put that tax money aside!

Try to create passive (or semi-passive) income

I sold pre-made templates that required installation but way less than half the work, so at the end of the day, those templates were a great way to make some extra cash.

A Back Up Plan isn’t a bad thing

As a self-taught blog designer who only knew the blogger platform, I was very aware that my business had a shelf-life. Right before launching The Everygirl, I was in crisis mode. I had to start something else or to go back to school to study web/graphic design. I never saw it as a sign of failure–it was just my reality. I needed to do something to make it work and felt a good mix of stuck and terrified.

It’s so worth it

Being your own boss is scarier, harder, and more rewarding than you could ever imagine.

Before taking the plunge, I would do everything you can to make sure you have some padding in your bank account for when things slow down, because they will. The only reason we were able to launch The Everygirl was because we both worked full-time from home that year, so having a full-time job and savings made it possible. I dipped into savings more times than I probably should have and burned through most of it but it felt worth it.

There were moments with both businesses when I questioned everything. That’s normal and will happen from time to time, but ultimately, nothing beats waking up every morning and doing something that’s yours, that you’re really passionate about.

Are you thinking about starting your own business or do you have one? I’d love to hear more about it. Please leave any questions or comments below. As always, I’d love to hear from you and would love to help if I can! 

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  • This is amazing. Thank you so much for sharing! I’m into the beginning of year 3 with my brand after leaving my corporate creative director position in 2015 and so much of what you said makes sense. The Everygirl blog is one of the reasons I started my business! I still remember reading an article on there years ago and it pushed me into action. So thank you for that.

  • Hi Danielle,
    I’m a graphic designer/art director, and I love the idea of going full-time freelance some day. I have a stable 9-5 and a solid income right now, so I’m really worried about the ups-and-downs of freelancing. How did you drum up business leads originally? How often, if ever, was there just zero work? What did you do to get out of that?


    1. Hi Jessica,

      I happened to get into blog design when there were (literally) a handful of blog designers out there. I shared the whole story here

      So it was a mix of hard work, crazy late hours, and excellent timing. I had a pretty regular wait list that went down to a handful or less of clients and at that point, I’d freak out, but then I’d get a bunch of inquiries. Like I said, I got really lucky. I never paid for advertising but had my link at the bottom of a couple thousand blogs floating around online. Probably not helpful but my whole situation was sort of weird/different.

  • I’m 99% sure I’ll open my interior design business I’ve dreamed about… pretty much my entire life, when I move back to Chicago. The only factor I need to figure out is how to get the clients. But I guess I’ll figure that out as I go.

    Very inspiring article! ???? Thanks for sharing.

    1. You can also start doing it part-time while you get things going! Not sure if this will help you but most of my designer friends book clients through referrals. So excited for you! Such a crazy/fun (and a little scary but worth it) experience!

      1. That’s my goal. I’ll have to see how everything pans out. I plan on moving back in October so I’ll have to see how it all goes and just embrace the crazy. I would love to meet up with you for coffee and chat when I move back!

        1. I’m actually getting married that month and will be gone for two weeks, and we’ll be in the middle of holiday content so meeting up would be really tough, but I’d be happy to share any advice I can over email.

  • Thank you so much for this! I’ve been following you + The Everygirl for longer than I can remember and so appreciate everything you’ve done! I’m a designer/art director and just recently went freelance ( It can be so terrifying sometimes, it’s encouraging to know that everyone has been there! When you started your online design business did you do lots of online marketing to get yourself started or mostly activate your existing network?

    1. You’re so welcome, Salina. Congrats on going full-time! It’s a journey but you’ll figure it out.
      The only marketing I did was putting my link at the bottom of all blogs I designed, and I kept it in my terms that my clients had to leave the link there. Brought a lot of traffic and clients my way!

  • As a beginner blogger, this is incredibly helpful advice. Often I feel so overwhelmed and like I have no idea what I’m doing, but it’s so reassuring to hear success stories and see the big picture. You’re such an inspiration and I found this post to be really helpful.

    White Silk, Black Leather

  • I’ve been interested in blogging, graphics, the Adobe suite, web design, etc. for a while but it all seems so overwhelming I don’t really know where to start! I’ve been reading around on your blog and it sounds like you were self-taught. Any tips on how you picked up HTML/CSS and Photoshop?

  • Thanks for sharing! I just left my corporate career in Marketing after 15 years to pursue Interior Design (which has been a long time passion of mine)…and considering a blog as a side project. This is definitely inspiring! As strong women, it’s great to hear about others out there willing to take chances and be confident things will work out, even if it’s a little scary in the beginning 🙂

  • Thanks for sharing Danielle! I’ve heard many of these before but it’s always nice to hear them reinforced. It shows that they really ring true! Currently I’m doing both graphic design full time during the day at a company, and also running my stationery design business on the side! I became an official ‘business’ with stationery this past March even though I’ve been doing it freelance for years and years. My goal is hopefully to grow it and maybe do it full time, but we’ll see how things go. So far this first year has been going well though! Thanks for always being so helpful!

  • That first one has been huge for me. I struggle with people (family, especially) calling my work a hobby. I got a Facebook message this week from a friend of a family member, asking me to answer some of her daughter’s questions about my “little typing job” which felt like a punch in the gut. I need to be more confident with explaining that freelance writing is my career, not something I’m doing just to pass the time.

  • I loved reading your story and I do have a blog for like 2 years but I am at the point of I have to monetize or do something else. I am retired and would like just some income but I am not very techy so everything has been a struggle. I took classes but need another way. I am on Pinterest Business acct but I had 125k but I am still doing the same as I always did but it went down to 9.5k. Any suggestions?