The 10 Things I've Learned from Freelancing


I’m not sure when the distinction kicks in, between freelancing and owning your own business? I never really know how to describe myself. Am I a business owner? Or just a freelancer? I guess it doesn’t matter too much - but I’m still working that out in my head.

I think I FEEL like a freelancer, but I would like to be a business owner, and have a proper office, and employees and all the rest - full disclosure!

It’s now been officially THREE MONTHS, since I left my comfy 9-5 position and have been working on my own. Some days I feel like I’m on top of the world, and other days I feel….very different to that. But, the one thing I will say, is that working from home is really the base case scenario for me personally, and I feel healthier, happier and just better in general by being able to set my own schedule and really dig into projects in the comfort of my own (casual wardrobe and) home.

While I’m definitely not the expert, with only 3 full-time months under my belt, I can share some things that I’ve learned!

  1. You need to be disciplined, because there is nobody there to hold your hand, or remind you that things are due. This was something I already knew. I knew that I had to be my own boss, obviously, and I knew that I’d need to force myself to do things even when I didn’t want to. And because I had done freelance for years before leaving my job, I did understand that there would be times that I would just have to force myself to get it done, so it’s been no extreme surprise to me. However….there is REALLY nobody to keep you accountable. Of course you’re responsible to your clients, but only you know what your proper process looks like, and whether or not you’re cutting corners. There have been days where I could have totally let myself get distracted with house work or errands, or deciding to bake something - but I REALLY try to keep “home things” for “home time”. Which is after I close the computer and turn off the light in my little desk nook area. The other unfortunate part of really being on your own, is that you don’t have a second pair of eyes on things (unless you hire an assistant - but we’ll get to that later!), or co-workers to ask for feedback, or have a brainstorm with. I’m a pretty independent worker so this hasn’t been too unfortunate for me. But, things slip through, and its nice to have another set of eyes, other than the client to review things. It’s a really unique experience when you work for yourself, where you have to actually be a master, not only at your craft, but also at all of the other things - the bookkeeping, the admin work, the project management. It’s kind of great because I’m flexing some muscles that I haven’t in a while, but it’s kind of scary because some of them are a little rusty! A regular daily schedule can be really helpful if you are in need of working on your discipline.

  2. Mistakes Happen. This month I feel like I’ve made a bunch of little mistakes. Sent an incorrect invoice, missed a detail on a project draft, and felt a creative block. I’m a sensitive person, so these kinds of things make me crazy - I always fly down the rabbit hole of dismay - I don’t want people to doubt my integrity (with the incorrect invoice), question my abilities (with the detail missed) or for me to wonder about my own creative potential. When you have a client/vendor relationship, sometimes you feel like you don’t get to know these people super well. It’s not quite the same as coworkers you see every day. You don’t go to lunch with them each week, or chat about the weekend over coffee in the morning. So it’s easy to think, “they don’t KNOW that I’m actually really genuine and honest, and they don’t KNOW that usually I’m typically pretty detail oriented, etc.”, but, at the end of the day, mistakes happen, and most people aren’t that deeply critical. That can be hard to accept when you feel anxious or uncertain, but it’s true. We really are our own worst critic. Chances are, they might be annoyed, but usually things like this won’t jeopardize a working relationship. And if you make a mistake that DOES jeopardize a working relationship? That totally sucks, but it can happen and it doesn’t have to be the end of the world (easier said than done, I know!). But, every time I make a mistake, I try to remind myself that this is the last time I’ll ever make that mistake, because I’ve taken a moment to absorb it, analyze it, put steps in place to prevent it and at the end of the day, I’ve learned from it.

  3. If It’s not working, don’t force it. Setting your own schedule is pretty sweet, but I was worried that I would end up being distracted all day and never work. So when Matthew leaves for work (between 7:30-8am - depending on the day) I always make sure I get up as well. I have set work hours for myself between 9-5, just like my previous full-time job, but sometimes, on some days, I feel totally stuck. I used to force myself to be at my desk during those hours, and even if I really didn’t want to, I would force myself to do work - but in the last few days I started to ask myself, why? Why am I forcing myself to do this work when it might actually HELP me if I switch my mind to something else (like my closet that desperately needed to be organized that was haunting me throughout my work day) and come back to work later. Sometimes getting the thing that is bugging you, out of the way can help you have a more clear and creative mind to power through, and get things done.

    I am most definitely not a morning person, so I am learning to let myself be flexible when I need to - but also stick to a routine to help keep myself on track. It’s a mix of both, but it has to be a balance. That’s the benefit to working for yourself, and frankly, it’s something I used to complain about when I worked 9-5. Sometimes I’d think to myself, “what if I can’t be creative today, and I have to be in the office from 9-5- but really, I need to take a walk, head somewhere that gets my inspiration going, and come back to it in the afternoon or evening to do better work?”. And now, I can do that (take a walk, come back to it). When the ideas or the inspiration won’t come, you CAN take a breather and really let yourself enjoy that creative process. Forcing yourself to sit at your computer, and end up on Instagram or wherever else, isn’t productive. So take that break if you need it! Just make sure you do eventually, come back to it!

    ”If it’s not working, don’t force it”, can also be applied to client relationships. Sometimes we really want a project or a partnership to work out, but sometimes it’s just really not the right fit - sometimes personally, and sometimes professionally. If you find yourself not enjoying working with someone….you don’t have to! And, it’s okay! This hasn’t happened to me yet - but it’s something I’ve thought about, for sure. Sometimes we’re just not the right fit for a business or for specific projects and it’s not always personal. It doesn’t mean you’re a bad designer/contractor, or a bad person, just like some friendships and relationships don’t work out, some business connections don’t either. The Universe, God, Life, Karma, whatever nomenclature you prefer to use - it will provide new opportunities for you in some way at the end of the day - so just chill a bit!

  4. Set clear boundaries between “work time” and “home time”. I’m finding this is especially hard because we live in such a small space. My little “study carol” for a desk is really awesome, it keeps me from being distracted by the laundry that needs to be folded, or the baking dish soaking in the sink, because I simply cannot see them! However, it does make it hard to really separate work and life - because this little study carol is in our living/dining space! I find that since my husband gets home so early from work (well, not SO early, but earlier than I used to at my full-time job) I continue to work when he’s home and done for the day, but I don’t always remember to stop! It’s small, but it has helped me - when I’m done for the day, I close my laptop (and I leave it there, on my desk), push in my chair, and turn off my sconce. When the light is off, the office is closed, I like to say! Just a small visual thing, but it has helped a lot in just reminding me, to not go back to my desk, and pick it up tomorrow morning.

  5. Remember to take breaks. I haven’t been awesome at this so far. I do enjoy some slower mornings - I take extra time to make coffee, and clean the kitchen a bit - make sure I get dressed for the day etc, but I haven’t taken a lunch break since starting to work at home. Usually I’ll have an egg and a piece of toast for breakfast, maybe more around a brunch-time - but then I don’t eat anything until well…dinner? Definitely inhaling the coffee as the day goes on - but I need to be better about scheduling some small breaks, and even if I’m not especially hungry, just to get up, walk around, maybe put on some laundry, or do something around the house that is a quick task, just to refresh my brain. If you follow me on Instagram, you probably have heard me speak about my 15-minute-cleans. I set the timer on my phone for 15 minutes, and just….go crazy! I try to clean or do as much as I can in 15 minutes, and then get back to work, or sometimes I will extend it for another 15 if it’s really messy or have more tasks to complete, but this just makes me hustle a bit more - knowing it can only possibly last for 15 minutes, ha! It’s also a good way to make sure you don’t get distracted with housework during your work day, and end up spending 2 hours doing laundry instead of gettin’ that work done!

  6. Don’t sweat the small stuff. I am a pretty anxious person, so I tend to sweat, um, like, everything. This kind of statement usually bugs me, because I can’t HELP but sweat the small stuff, but it’s really true. I am trying to remember that not everything is personal, and not everything mean as much as my anxious little heart says it does. Running a business, or working freelance is tough, and you have to get thicker skin if you want to survive. If I spent every day worrying about if I could REALLY do this and keep it going for the next 10-20-30 years or not, I wouldn’t be getting anywhere. You have to just trust that you are talented enough, brave enough, smart enough to do it. You can totally do this. We can totally do this!

  7. Make yourself get out of the house. I’m pretty terrible at this, because my favourite place to be is at home. Sometimes I realize I haven’t left the house in DAYS and I will try and make myself get out - even to do a small errand. Sometimes I even just go out on our deck (yes, in the winter) and get some fresh and frosty air! A walk around the block is always good too. Or, checking our a favourite store or place, can give you lots of good inspiration. This place for me, is Homesense! I find just wandering the aisles to be really relaxing, and even if I don’t buy anything, I feel totally refreshed looking at all of the interesting pieces and products that they carry. The best thing about this store is that everything is pretty affordable, so if you do fall in love with something it’s not going to ruin you, but also, their assortment is never the same, so you can never get bored! The evenings are typically pretty quiet, and I am usually able to go after the workday, so thats when I like to go. Lots of time to browse, and it’s never crowded. I always make sure to grab a buggy, even if I don’t want anything specific - you can plop your purse in there, and if you do find your next holy grail item, you don’t have to worry about someone snagging it before you get a cart - you’ve got one right there!

  8. Remember that you’re playing the long-game now. Those little wins, or little mistakes can totally affect your day, and even your week. But you have to remember, with good momentum, and even setbacks, the journey of owning and succeeding with your business is long. There will be great days, bad days, confusing days, days where you just #canteven, and all of the days in between. Keep the momentum and remember that tiny steps, still move us forward! Don’t get too comfy and try not to get too in your head about a great month, a bad month, or a mediocre month. Keep your eye on the long game - it’s a marathon now, babe - not just a sprint! And this brings me to my next point….

  9. Make sincere goals and plans for your business (that aren’t just about money). While it’s important to look at the month ahead - is that all your doing? I think when we look too closely at our future, we forget that the future holds a really long amount of time. For me, to keep getting up every morning and finding satisfaction in what I’m doing, I have to look forward. Like reaaally forward. In the past six months I’ve had to really, seriously ask myself: Do I want to make a nice tidy income, working at home, having a great work-life balance, leaving space to be a part-time stay at home mom etc, or do I have dreams that include having a team work with me, and renting out a larger office space in the future? What does a healthy work/life balance look like for me personally, and for my family? Some of these questions have bits to do with money, but they aren’t focused on the dollars and cents as the be all, end all.

    I think when we focus on building a business that supports the lifestyle that we have dreams of living, we can really set our sights on specific goals to get there. Leaving my full-time job wasn’t just about money - if it was, I would have stayed until I found another interesting job that made even more money! But I had dreams of impacting the design space in a way that I would be unable to, while working there. I wanted to feel more present in my own life. I wanted to have the bandwidth and energy to take on new challenges outside my comfort zone. I wanted to have a work life that worked best with my personality (Hello, I’m an introvert who worries about legitimately, everything). I wanted to save some of my social energy for friends and family, and actually want to end up attending events happening in my life, instead of feeling depleted from being around people at work (no offence to my lovely ex-coworkers! It’s not you, it’s deffs me - love you guys!).

    To get a little personal, one of my goals, is to be busy enough to hire an assistant. Not necessarily full-time, but a few days/hours a week. I know there is a fine line between waiting until you need to outsource, and also waiting TOO long to hire, and providing bad service - so I am just trying to be conscious of the fact that you usually need to hire before you feel like necessarily need to, or can afford to.

  10. Have fun. One of the biggest indicators before I left my job that I needed to make a change was honestly just my ability to get up and get ready in the morning. Naturally, I’m not a morning person as I’ve said 100 times, but there was something more than that. I wasn’t really enjoying what I was spending my time doing. Not to say that work should always be rainbows and butterflies, but there should be a little pep in your step! Of course jobs, relationships, and life in general go through ups and downs, but having “fun” or at the very least, a deep sense of satisfaction, is super important! Remember that life is really yours to live. It’s up to you how you choose to spend your time, and how you choose to use your own “power”. I used to read sentences like that and think like, “ugh, such privilege! I can’t just leave my job and do something fun! I have bills to pay!” And, yes, that is super true - you can’t just run off at a moments notice and decide to be an influencer, or a blogger, or something that you don’t have the foundation to do yet, and I definitely do not recommend taking the jump without some type of safety net - but you CAN make plans, and try your best to make something new for yourself happen!

If have been thinking of doing something new for yourself, or taking a leap - I would encourage you to do all that you can to take that step! Maybe that means cutting down your trips to Sephora, or reaching out to people you admire and asking if you could shadow them. Honestly, maybe it just means taking a class on Skillshare - or starting that instagram account! If you have any questions, I am genuinely happy to chat with you about where you’d like to be headed - or even just about the trials and tribulations of freelancing! It’s fun and scary all mixed together, and I can truly say, there is nothing like it!