What I’ve Learned After 1 Year of Self-Employment

June 27, 2016

What I've Learned After 1 Year of Self-Employment

What was your first grown-up job? One where you thought, “yes, this is the beginning of my career”. In the summer of 2006, I worked as a Jr. Communications Officer at what was then known as the Public Affairs Bureau for the Province of BC. There, I wrote media releases, briefing documents, and speeches for MLAs and a Cabinet Minister. And I was mentored by two smart, talented and driven women: one was a single mother, the other was married to a highly-respected health officer. At the age of 21, I thought I had found my career; this was the place I wanted to be and the ladder I wanted to climb.

At no time in the nine years that followed did I ever think I would work for myself. After graduating from college in 2007, I had a 5-year career in the government, followed by 3 years at a startup. I had always assumed I would stay at one company for a long time, like my parents did, or do 5-10 years at a few. Working for myself wasn’t the goal – until it became an option

It’s hard to believe it’s already been a full year that I’ve been out on my own. On June 26th, 2015, I finished all my work, reached inbox zero then logged out of the 9-to-5 world. At the time, I was equal parts excited and scared. I knew I had enough freelance work lined up that I would survive through to the end of 2015, but I had no idea what would happen after that. As you can see, I’ve obviously made it to mid-2016 and it’s been one of the most rewarding years of my life. I’ve grown personally and professionally, thanks to many life lessons learned along the way. Here are some of the big ones:

You need to get comfortable with irregular income.

Aside from having to get comfortable with working at home (which I’d already been doing for two years) and trying to stay motivated (same answer), without a doubt, the biggest difference between working for a company and working for yourself is earning irregular income. Sometimes, that means not earning much one month, but earning double or triple the next month. Sometimes, that also means not being able to save money one month, but being able to save a lot of money the next. I don’t always love that, but remember it will all even out by the end of the year.

A (huge) cash buffer will help you sleep at night.

There will be weeks when your accounts look low and you want to pay off your credit card in full, but you’re waiting on thousands of dollars to come in. A cash buffer / emergency savings / whatever you want to call it will alleviate your financial stress. Don’t touch it, unless you absolutely have to. Just keep it there, so you know you’re always covered.

Always save more than you need for tax season.

You’ll probably read that you should save 25-30% of your income for tax season, and you should. You probably won’t need all of it, but you should still save it. I saved 30% of my self-employed income last year and only ended up needing about half of it (thanks to my retirement contributions, businesses expenses and accountant for dealing with all the numbers). Even though I know I won’t need it all, I’m saving 30% again this year, because it also alleviates financial stress. And it means I’ll get a nice “bonus” (of money I didn’t need to pay the CRA) each spring. So save save save. Future you will thank you!

Only say yes to the work you actually want to do.

A common mistake made in your first few months (or even years) of working for yourself is saying yes to every opportunity that comes your way. You think you’re crazy to say no to money, and even worry that if you start turning work down, it’ll all disappear and no one will ever want to hire you again. Unfortunately, this can result in saying yes to projects you don’t want to work on, which always leads to someone being unhappy. Either you resent the client for making you work on it, or your client resents you for not doing a good enough job. And it all could’ve been solved by simply saying no.

The easiest way to know if you should say yay or nay to a new project is to first define what kind of work you want to do. Are you a writer who likes writing long blog posts but hates doing interviews? Don’t accept feature story assignments! Are you a designer who prefers to work on big branding projects vs. small one-off projects? Market yourself as a branding expert! Write down the types of work you like to do, and only offer that list of services to potential clients. If it’s not on the list, say no. (Carrie and I talk about this more in tomorrow’s episode of Budgets and Cents!)

If you feel like you’re getting underpaid, you will hate the work.

Determining your rates is often a point of frustration for freelancers – and it comes up every time you sign on with a new client. You worry that if you charge too much, you won’t get the job, and if you charge too little, you undersold yourself and are missing out on extra money. I’ve learned that if I feel like I’m not getting paid enough, I won’t enjoy the work; this translates into procrastinating until I’m dragging my fingers across the keyboard to get it done. If you charge what you’re worth, you’ll feel good about doing it! (And if a client won’t pay you what you’re worth, it’s better to say no thank you.)

Pay other people (what they are worth!) to help you.

One of the things I’ve enjoyed most about working for myself has been hiring other freelancers to help me with projects – and paying them what they are worth, too! I’m not banking millions over here, by any means, so I’m not exactly throwing money around. But I’ve learned that, even though I could probably do some of this work myself, my time is better spent writing. And to that end, it’s cheaper for me to pay an expert than to waste my time trying to do some things myself. (Note: I also like to pay the same day I receive an invoice, because I know how satisfying it is to be on the other end of that.)

At the end of the day, it feels good to know that the opportunity to work for myself has also given me the opportunity to work with other people whose work I love and respect. Even though we’re all freelancers (and some could look at us as competitors), I like to think we’re all co-workers in this weird world of online business.

Hire an accountant.

Seriously, just do it. It is literally the best money I’ve spent all year.

You’re in control of your schedule – so control it!

When you work from home, it’s easy to slip into a pattern of working all day every day – not just because you want to make money, but because you genuinely enjoy the work. Unfortunately (or fortunately?), no matter how much you love it, it’s not healthy to work during all your waking hours. You need to take breaks, take days off and take vacations. And you’re in full control of your schedule, so you have the power to create a routine you love. For example, I usually take Tuesday off to go hiking, as well as Friday afternoon and most of Saturday. (I also take a few hours off most afternoons!)

The key with this is to take your schedule seriously. If someone asks if you can finish an assignment while you’re on vacation, either get it done before you leave or say no and tell them when you’ll be back. The same thing goes for regular days off. You need them. Your body needs them. And trust me, your client needs you to take them. I’m a firm believer in not only managing your time, but managing your energy – and if you don’t take care of yourself, I can guarantee your energy will be low and you won’t be very productive. Eat well, take breaks, go for walks and get some exercise. It’s that simple.

“Your mornings will never be the same.”

That’s what David said to me, when I told him I quit my job. One year later, it’s still the best statement I can use to describe what it feels like to work for myself, and is what I now say to everyone I know who quits their job. “Your mornings will never be the same.” You won’t dread the sound of your alarm clock (likely because you’ll stop using one). You won’t rush around to get ready (because, at most, you’ll get dressed and brush your teeth). And you won’t hate the thought of going to work (both because you don’t have to commute and because you love what you do). Mornings are my favourite time of day now.

Be grateful and have fun!

There is not a day that goes by where I’m not grateful to be in the position I’m in right now – grateful for the opportunity, for all the clients who have trusted me, and for my family/friends who have supported me. When I quit 12 months ago, I told myself that even if I had to get a job after six months, I would never regret taking the chance to work for myself. And every month that goes by, I think, “wow, I’m still doing this!” It seriously feels like a dream. But, like any dream, I have no idea how long it will last. Maybe I’ll survive another year. Maybe two. Maybe five. Or maybe I’ll get a job again. Who knows!

What I do know is that I’m going to enjoy this self-employment journey for all it is, as long as I can stay on this path. It has come with freedoms I never knew existed, and opened more doors than I could’ve imagined. I’ll share more details about that in another post later this week. Until then, I think Carrie would ban me from our podcast if I didn’t celebrate this milestone… :)

How do you celebrate your successes*, friends?

*Don’t say retail therapy!



  • Reply Kate @ Cashville Skyline June 27, 2016 at 4:27 am

    Congratulations on a successful first year, Cait! I love all your tips, especially the one about only taking on projects you really want to do. That definitely applies to side hustling, too! Nothing is worse that spending your nights and weekends on a project you’d rather not be doing! And I love your recommendation to pay everyone what they’re worth. I’ve followed that rule, too.

    • Reply Cait Flanders June 27, 2016 at 7:21 am

      Oh, it definitely applies to side hustling! If you don’t like the work that you agree to do on the side of your day job, you definitely shouldn’t do it. Extra money isn’t always worth it.

  • Reply Our Next Life June 27, 2016 at 4:30 am

    So many great lessons here! I agree that working from home takes some major adjustments (feel free to share those lessons, too! I’ve been working remotely for five years, but feel like I can still improve at it), and I can only imagine how much more adjustment it takes to get used to the uncertainty and ups and downs of freelancing. But you definitely make it look easy. I also think that every single piece of life advice ever should end with “be grateful and have fun”! ;-)

  • Reply Andrew June 27, 2016 at 4:51 am

    Congratulations on your first year Cait! I love the part about taking care of yourself first. Actually I love all the lessons in here. There are some great insights for someone like me who is just getting started in this area. Thank you for sharing your knowledge. It will definitely help.

    • Reply Cait Flanders June 27, 2016 at 7:25 am

      Thanks, Andrew! Glad you liked it. :)

  • Reply giulia June 27, 2016 at 5:09 am

    congrats for this lovely first year of self employement :D

    • Reply Cait Flanders June 27, 2016 at 7:25 am

      Thanks, Giulia!

  • Reply Rob June 27, 2016 at 5:21 am

    “How do you celebrate your successes*, friends?”

    Retail therapy? :-) Naw, just kidding Cait (although I do enjoy a small “at-a-boy” self-indulgent sweet piece of chocolate cake to celebrate on occasion).

    Actually, though, I tend to celebrate my successes by reflecting how I achieved them – what were the mistakes made, what were the lessons learned, what plans will I be making to repeat those kind of successes while lessening the risk of repeating those past mistakes. It’s all part of living to one’s potential and then going a step further in stretching one’s self to perform even better with loftier goals.
    Just like you’re doing, buddy!

    • Reply Cait Flanders June 27, 2016 at 7:27 am

      Your comment made me think of one more lesson I’ve learned, Rob, and that’s to setup systems for certain tasks! I would be lost without my budgeting/accounting systems, onboarding systems and more. And only learned that by making some mistakes! Every month feels like a new month, and is a little more streamlined than the one before. Makes work and life so much easier. :)

  • Reply Kalie @ Pretend to Be Poor June 27, 2016 at 5:43 am

    Really good advice, Cait! I agree that working on projects you don’t like, or that under-pay, really defeats the point of self-employment. But I understand how tempting it is to say yes to everything, especially at first. I’m glad you’ve loving your work now, and your mornings!

    • Reply Cait Flanders June 27, 2016 at 7:33 am

      One of the scariest decisions I’ve made, so far, was saying no to a steady income of $1,000/month from one client… and I had to do it because I could tell I wasn’t going to enjoy working with the client. So many red flags! I had to trust my gut instinct and know my personal limits. Zero regrets.

  • Reply Rachel @ The Latte Budget June 27, 2016 at 6:18 am

    Congratulations on your one year! Though I am still blogging on the side, I can agree that my mornings aren’t the same since blogging. I jump out of bed and am ready to go! I think I accomplish more in my first hour of the day than I do for the entire rest of the day. Gotta love what you do, and I’m glad you seem to love it!

    • Reply Cait Flanders June 27, 2016 at 7:35 am

      That’s awesome, Rachel! It feels so good to wake up happy and excited, doesn’t it? :)

  • Reply Eric Bowlin June 27, 2016 at 6:25 am

    “Only say yes to the work you actually want to do.” This is something I followed back when I was still working. People would be absolutely SHOCKED when I’d pass up work…as if their money was greener.

    Everything else is great advice too.

    • Reply Cait Flanders June 27, 2016 at 7:36 am

      Haha, I’m guessing you got a few blank stares, Eric. Good for you for knowing your limits and working within them.

  • Reply Jenn June 27, 2016 at 7:08 am

    Spa pedicure vs. Basic pedicure. This is my treat as I’m trying to not reward myself with food. I am not a dog.

    • Reply Cait Flanders June 27, 2016 at 7:37 am

      Oh my gosh, that made me laugh, Jenn – but is also brilliant! Just texted that quote to a friend. :)

  • Reply Julie@ChooseBetterLife June 27, 2016 at 7:33 am

    Congrats on your anniversary and season 2 of your podcast- Yay!

    I had sooo much school that my first “real” job wasn’t until I was 29!!! Sometimes it gets so bad that I wish for my “non-real” jobs at a bank and restaurant. So now I’m working on starting my own business and it’s so much more fun to get up on the mornings I work on these new projects.

    • Reply Cait Flanders June 27, 2016 at 7:40 am

      Sounds like your mornings will never be the same either, Julie. :)

  • Reply Jordann June 27, 2016 at 8:13 am

    It sounds like your first year of freelancing was a success, which is great! I need to get better at the “only saying yes to the work you love to do” both in my side hustle and at my full-time job.
    Question: How long did it take you to get out of the starvation mentality with accepting new work? You mentioned feeling like it could all dry up at any moment, how long did it take you to become comfortable with not accepting work?
    I ask because I’m still not comfortable with it, though I wish I was.

    • Reply Cait Flanders June 27, 2016 at 9:50 am

      That’s a really good question. In some ways, I don’t think it ever goes away… I felt it just last week! But with each month that passes, I can look at my numbers in FreshBooks and see two things: 1) I’m always doing better than I think I am, and 2) there are sooo many ways to make money (which is evident from the number of clients/projects I have). So I guess it’s just trusting that what you’re doing is working, and then hoping it will continue to work. I’m going to talk a lot more about income later this week!

  • Reply Louise Rayner June 27, 2016 at 8:28 am

    It will be 16 years of self-employment for me September 6th. It’s been a roller coaster ride, but one I love most days. You are right the irregular income is the hardest to deal with, even 16 years in. As an accountant, I glad you commented to hire one. I met with a client this morning who’s wife is looking to start a business this fall. We were able to talk about start-up, expense tracking and other issues before she starts. So much better than trying to fix mistakes/issues later on.

    • Reply Cait Flanders June 27, 2016 at 9:52 am

      Oh, hiring an accountant is a must. Honestly, I started emailing different accountants in the area, even before my last day at work! I knew I wanted someone to look at my numbers (especially expenses) and work their magic. Best decision ever. :)

  • Reply Bri June 27, 2016 at 8:41 am

    Congrats!! I hope to make this leap one day (currently 4 years in government communication/project management) with a regular side gig freelance fitness writing, blogging and coaching. It’s hard to know when to make the jump (probably when I pay off my credit card debit??) to leave the cushiness of the government, especially in these times.

    • Reply Cait Flanders June 27, 2016 at 9:53 am

      Yes, I’d say once your debt is paid off and you have a solid amount of savings in the bank to float you if you ever needed it. I don’t think I would’ve felt comfortable quitting if I didn’t have that – plus enough work lined up to know I could survive for the first six months! Everyone’s numbers are different, but I would say you have to be comfortable with your monthly cashflow, before you think about quitting. I have a feeling it’ll happen for you. :)

  • Reply Emily @ Always Emily H. June 27, 2016 at 9:42 am

    I just had a light bulb moment when I read this: If you feel like you’re getting underpaid, you will hate the work.

    Even for those who do not work for themselves, this is often times quite true. I recently left my dream job where I initially loved the work because I ended up hating it due to being drastically underpaid. I am now at a job less suited for me but being paid appropriately and am not hating the work even though it is boring (and I should probably hate it). Thank you for bringing this to light!

    • Reply Cait Flanders June 27, 2016 at 9:54 am

      YES! I’m writing about this exact topic on Wednesday, Emily. Glad you had a lightbulb moment! (And even more glad that you’re happy now!) :)

  • Reply Alexis Kienlen June 27, 2016 at 9:52 am

    I have worked at home for almost 8 years now. I have a job, but it is very flexible and I take freelance writing gigs and do creative writing on the side.

    So much good advice here- from accountant to passing up on work you don’t love etc.

    Strategies that I use- I don’t work at night. I try to make sure my evenings are free. I keep my computer out of my bedroom. And I have a landline, so that functions as my work phone so that people I am interviewing etc, can’t get hold of me at all hours, and I can maintain a separation from work.

    I should add that work does pay for my landline, so I might not do this if I have to pay for it myself.

    • Reply Cait Flanders June 27, 2016 at 9:58 am

      Good add-ons, Alexis! I’m weird and actually prefer to work at night, but I love taking afternoons off. I don’t know why, and I also don’t think it will last forever… but working whenever you want to is a luxury when you are single and live alone. Totally agree about not bringing computer into the bedroom. That’s my sanctuary. Books only. :)

  • Reply Revanche @ A Gai Shan Life June 27, 2016 at 10:19 am

    Happy first year anniversary, Cait!

    I love these review / recap posts, it’s good to hear how things are going and what mistakes have been made, what lessons have been learned.

    Though my situation is quite different from yours (regular jobs! four dependents! lots of travel!), I remain inspired by your choices. Even if I can’t do exactly the same thing, you give me food for thought for what I might be able to do when the time comes.

    • Reply Cait Flanders June 27, 2016 at 4:04 pm

      Always glad to add food for thought to the table, friend! Thanks for being part of the journey. :)

  • Reply Linda @ Brooklyn Bread June 27, 2016 at 10:28 am

    Very inspiring . There is such a leap between thinking you’d like to be in control of you life and then actually doing it. It takes some bravery to go for it, but it sounds like its really paying off for you. Your tip about having a buffer is so key – that is the idea that is so scary to people – not having that regular paycheck, all the what if’s! But it is great to see people succeeding, making money by offering hard won insights to people and putting something good out into the world. As I shill products in my PR day job, I dream that one day some years from now I can make money in a way that is useful to people, instead of just being one more sales person!

    • Reply Cait Flanders June 27, 2016 at 4:08 pm

      Your background will certainly help you, when the time is right, Linda! I often think I’m a terrible marketer (or just find so many of the usual tactics “icky”). You could always offer your services on contract, too. :)

  • Reply Catherine June 27, 2016 at 10:34 am

    Congrats Cait. I know myself well enough to know I have zero desire to work for myself, I admire those that do! I usually don’t feel the need to celebrate, I get enough out of knowing I succeeded!

    • Reply Cait Flanders June 27, 2016 at 4:09 pm

      Thanks, friend! And yea, it’s already 4pm and I haven’t even thought about how to celebrate, haha. Think I’ll chalk this milestone up to a win and call it a day :)

  • Reply Kara June 27, 2016 at 11:29 am

    This is a great read! I’ve been freelancing for two weeks, but I already love my mornings so much more. And I have NEVER been a morning person! Not dreading the work you have to do is a total game changer. Thanks for writing this Cait!

    • Reply Cait Flanders June 27, 2016 at 4:10 pm

      Glad to hear you’re enjoying it so far, Kara!

  • Reply Mackenzie June 27, 2016 at 3:36 pm

    Congrats on an awesome first year Cait! Cheers to many more successful years to come :)

    • Reply Cait Flanders June 27, 2016 at 4:10 pm

      Thanks, Mackenzie! :)

  • Reply Scott June 27, 2016 at 6:03 pm

    Happy One Year Anniversary of taking control of your future! I read a blog post recently that was almost a polar opposite of this one (was about why working for a company fit the blogger better than working for themselves). Super interesting to see some of the parallels, as well as the opposing approaches to the same topic from two people who are doing it!

    • Reply Cait Flanders June 28, 2016 at 7:47 am

      Yes, I think you’re talking about the one my good friend Krystal wrote! (We went to college together!) I think it all comes down to knowing what type of work environment you prefer and what’s the best fit for your personality/lifestyle. When I look back at the reasons I used to “hate” jobs in the past, it always came down to the fact that the pace felt too slow and/or I wanted to get my hands on a bit of everything. I hated having to wait for permission to start things or to try things my way. I also like being in control of how much I earn, even though it’s irregular and not as much as I used to make. So really… it makes sense that I prefer to work on my own!

  • Reply Katherine Blaney June 27, 2016 at 7:32 pm

    Thanks for sharing! There is so much insightful content in this post – I especially like the thought “I like to think we’re all co-workers in this weird world of online business” and I definitely agree that you need to hire others to help you sometimes!

    Keep up your awesome posting :)

    • Reply Cait Flanders June 28, 2016 at 7:48 am

      Thanks, Katherine! :)

  • Reply Maryalene June 28, 2016 at 4:58 am

    I’ve been self-employed for 5 years, and it’s hard to remember what life was like when I needed to be in an office at a specific time each day. Part of me misses the leaving work behind aspect of a 9-5 job (seems there is always work you could be doing when you’re self-employed) but I certainly don’t miss the inflexibility of an office job.

    It’s funny because I took the kids to the beach yesterday, and we inadvertently left at 5pm. I couldn’t figure out why the traffic was so bad and then it dawned on me that it was rush hour and everyone was heading home from work.

    • Reply Cait Flanders June 28, 2016 at 7:49 am

      Haha, I love those moments most! When you’re totally clueless about what’s normal to others vs. what is now normal to you. :)

  • Reply Jack June 28, 2016 at 6:46 am

    You’re so inspiring Cait! Thanks for all the tips. I’m going to keep working at my full time job until I have that huge cash buffer you talk about. There’s definitely too much anxiety without it!

    • Reply Cait Flanders June 28, 2016 at 7:52 am

      I think that’s a great idea, friend! I’ve had to use mine a couple times and am always grateful it’s there.

  • Reply Hanna @ TheMillennialNextDoor June 29, 2016 at 7:16 am

    Great post! It is my lifelong dream to quit the 9-5 life and work for myself, doing something I love. I’m not sure if it will ever happen for me, but it’s inspiring to read about others who have made it a reality! I appreciate the honesty in this post and that you make it clear that this lifestyle isn’t all sunshine and roses. I think we have a tendency, or at least I do, to put our fantasy lives on a pedestal but as we should all know by now, the grass isn’t always greener on the other side. Congrats on your 1st successful year!

  • Reply J. Money June 29, 2016 at 12:45 pm

    Well that was fast :)

    I was nodding to almost all of these!

    What actually inspires me the most about you is that after all the talking and thinking about stuff (whether it’s this or anything else), you actually finish the process by TAKING ACTION on it. Not everything is a “go”, of course, but so many people talk and talk and wonder and then talk some more and never end up going after anything. (And as you know, I fall into this too)

    So I’d like to simply congratulate you on making the decision to go for it! I’m glad it’s working out so far, of course, but I’m more impressed with how you always follow through with things.

    Congrats, my friend :)

  • Reply Shelly Seward June 29, 2016 at 5:31 pm

    So much wisdom in one post! Congrats on your one year anniversary of self-employment. I’m sure wherever you are in one, two, or five years; you will be successful.

  • Reply Leanne July 1, 2016 at 4:03 am

    I’m hoping to at least go part time and do some freelance work by 2017 and you’re such a huge inspiration to me Cait! So grateful to call you a friend xx

  • Reply Elizabeth Mayberry July 3, 2016 at 3:08 pm

    I love this so much! I just went full time self employed June 4th 2016 (one month tomorrow!) and I am learning so much every day. This is such great advice and I am soaking it all in!

  • Reply Haley July 12, 2016 at 9:32 am

    I’ve been at my first ‘real job’ for about 5 years and I’m still in denial that this is an actual career. Great tips for self employment! Also, I’m happy you mentioned the podcast.. I just started listening to them during my commute and was looking for more, so I’m looking forward to adding yours to the list

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