Why I Quit Freelancing (to Really Work for Myself)

Why I Quit Freelancing (to Really Work for Myself)

It’s been quite a week, friends. On Monday, I literally touched three states and one province, driving from Boise, through Oregon and Washington, all the way back home to Squamish. I got to catch up with a few good friends on Tuesday morning, then tried to get back into work mode. Admittedly, the anxiety and grief I’d been trying to ignore on my trip caught up with me, and I have since shed a lot of tears – and, as a result, did not get a lot of work done. But with the low’s, I can always find a high – and I did have one thing to celebrate this week.

Wednesday marked the beginning of my third year of self-employment! As I’ve mentioned in previous posts and on the podcast, I never thought I would work for myself. It wasn’t part of the plan. When I got a job with the government in my early twenties, I thought I had made it. I was going to climb that career ladder until I retired and collected my pension. That was the plan. Quitting to work at a startup wasn’t part of the plan. And quitting the startup to become a full-time freelancer definitely wasn’t part of the plan. Then one day, it became an option.

My first day of “funemployment” was June 27, 2015. Looking back on that now, I had absolutely no idea what I was doing. All I knew was that I had six months of freelance lined up, and a four-month buffer in savings I could use if I ever found myself without work. If I had to find a job after that, I told myself I’d never regret at least getting a taste of working for myself. The opportunity presented itself and the shopping ban taught me how little money I needed to live on. I had to at least see what would happen if I went out on my own.

After my first year of self-employment, I outlined most of the lessons I had learned in this post. You definitely need to be comfortable earning (and budgeting with) irregular income. Having savings in the bank is what will help you sleep at night. You should always save more than you think you’ll need for tax time (because not doing so could end your business). Hiring an accountant will be the best money you spend all year. And if you don’t feel like you’re being paid what you’re worth, you won’t enjoy doing the work.

All of those lessons still ring true for me today, but I learned another lesson in my first year that I wasn’t ready to share until now: I don’t actually love being a full-time freelancer. And by “freelancer,” I mean writing and doing other kinds of contract work for clients. When I quit my job, my goal wasn’t to do client work forever. My goal was to work for myself. I wanted to wake up in the morning and spend the first few hours of my day working on my blog. And for the first two years, I couldn’t, because I was always putting my clients first.

Blog posts were delayed. Some weren’t written at all. I have over 50 of them currently sitting in my drafts folder, right now, along with a list of ideas I’ve thought about working on. None of them have come to life yet because I always prioritized my clients’ goals and deadlines over my own.

This has been a running theme in all areas of my life: putting other people first. I didn’t actually realize that, until I started therapy in April and figured out a number of issues could be fixed by setting more boundaries in my life. On the personal side, that has meant communicating more of my thoughts and needs with the people I love (which has been both terrifying and liberating). And in my business, that has meant being honest with myself about what I want – and don’t want – and communicating that to my clients.

There are a number of reasons why I knew I wanted to quit freelancing one day:

  • I stopped feeling excited about the work.
  • I hated having to follow-up on late payments (this wasn’t an issue for me in 2015/16, but I feel like almost all of my clients were late to pay in 2017).
  • I started resenting the clients who paid late.
  • I then procrastinated the work.
  • And I wasn’t being the best freelancer I could be.

But I was still afraid to cut the cord. I first started freelancing on the side of my day job back in 2011, and it had done so many good things for me. It boosted my annual income, which helped me pay down my debt sooner. I then funnelled that money into my emergency fund, which helped me feel comfortable quitting my day job. And having enough client work lined up is the only reason I was able to quit my day job at all. For all those reasons and more, freelancing had been an incredible gift.

The problem with “gifts” like this is that I am the type of person who feels like she owes people things in return. I stayed at my last job for longer than I wanted to because deep down I felt like I owed my boss something. I felt like she had taken a chance on an island girl, brought her to the big city and made some of her dreams come true – and I owed her. The problem with quitting to work for multiple clients is that I then felt like I owed multiple people for the opportunity. I am grateful for it. But feeling like I was obligated to work felt – well, like an obligation. And pushing back my own goals for two more years felt like I was giving up on my dreams.

It wasn’t until a friend suggested I look up what percentage of my income has been from freelance work in 2017 that I realized I could potentially walk away from it. The answer: less than 10%. Last year, it was 31%. I needed that money. And I still need the 10% it’s given me this year, but I also know I could make up that 10% in other ways – ways that would involve me finally putting myself and my blog first. With these numbers in mind, I was one step closer to quitting. The day Lexie died, I made the decision and sent the emails to my clients.

Similar to my experiences with learning to communicate more of my thoughts and needs with loved ones, quitting has been liberating. Immediately, it felt like a huge weight had been lifted. And it’s opened up so much space for creativity and inspiration to pour into the work I’m doing.

But it’s also been terrifying. On top of always putting other people first and feeling like I owe them, something I am only just starting to talk about in therapy is the fact that I don’t feel like I am worthy of all the good that comes into my life. I don’t know where this belief comes from. I didn’t even know I had it, and I almost quit therapy when I realized I was going to have to dig deep and figure it out. But it’s there – hidden underneath every part of my life, including my work. I don’t want to feel this way anymore. It’s a recipe for a life of lost dreams.

So, here I am: at the beginning of my third-year of self-employment, and my first year of truly working for myself. I will never say a bad thing about freelancing. I didn’t quit because I hated it or hated my clients. I quit freelancing because quitting became an option, and I knew I would regret not seeing what would happen if I went out on my own. I also quit because I want to believe I am worthy of the opportunity.

Like so many of the changes I’ve made in my life, I don’t know how this is going to turn out. But losing both girls in nine days reminded me that life is short – too short to keep putting myself last. If I owe anyone anything, at this point, it’s me. And if I’m good to myself, I have to believe I’ll be a better version of myself for you too.

As always, thanks for your support. <3

  • What a beautifully written, thoughtful post, Cait! Thank you for sharing this story. As a long time reader of your blog, it is really insightful to hear the “back story” to the progress I’ve seen and the transitions you have made over the years. It is really inspiring. Thank you for the great Friday post, looking forward to continuing to follow your journey!

  • Cait – I continue to watch you grow and bloom and deliver on promises to yourself in amazing ways. We’re all just figuring this whole LIFE thing out and it’s not easy, but you become stronger, more creative, and healthier with each step. I’m proud of you and hope my journey is as redeeming as yours has been.

    • Thank you so much, my friend. Sometimes it’s difficult to really see all the changes as you’re making them… but it helps when friends are keeping track for you. :)

  • I’m a true believer that you get back in life what you dish out. So for you to say you “don’t feel worthy of all the good that comes to you in life” is a direct representation of how good of a person YOU must be. Listen, I don’t know you personally but I can tell without a doubt you’re one of the nicest, most genuine people walking this face of the earth so yes you so deserve everything that’s come your way. Good for you for quitting freelance, I know *exactly* how you feel. I was lost and had no time to blog, sold it and ultimately had my voice taken away (which comes to be expected with a sale) though I miss scratching that creative itch, I don’t miss the stress of meeting deadlines anymore. I may look to take on posting somewhere once a month or something because I genuinely do love the blogging community but it would need to be the perfect opportunity with my boundaries set from day one. No doubt you’ll fill that 10% void no problem at all!

    • Well, I certainly appreciate all the kind words, Catherine! The not feeling worthy stuff feels pretty deep-seated, at this point. Like there’s something hidden inside me that tells me I’m not good enough. I truly didn’t know it was there but am grateful it has come to light at this age, so I actually have a chance to change it. And if you ever start a blog again, you know I’ll be reading. :)

  • Beautiful post, Cait. I admire your strength and tenacity and your willingness to be vulnerable and share with us what motivates your decisions and the choices that you make. :)

  • Thanks so much for sharing! I can definitely relate to the way you’re feeling (not worthy of good things). That’s definitely a scary thing to learn but now you’re at the beginning of writing a new pattern. And that’s so exciting! Congrats on taking a step towards working for yourself and your awesome blog!

    • Thanks, Brittany! And you’re right: I’m at the beginning of something new and it does feel exciting. :)

  • This is so inspiring! I remember reading about when you first went fully freelance and being inspired by that too. I’m about to embark on going freelance myself, and I think where I want to eventually get to is working fully, truly for myself. But right now I’m so happy to take this first step. Beautiful post and so encouraging to hear from someone that step ahead on the journey.

    • Congrats on switching to freelance, Grace! Like I said, I’ll never have a bad thing to say about it – especially because it helped me transition to where I’m at now. So I’m excited to see where your journey takes you, too. :)

  • I’m so glad you were able to take the leap and do this! I think you are so very talented, and I am honestly excited to see what you pour your heart and soul into next…whatever it is, I’ll be following it!

    Thanks for sharing your story with me. I feel like it’s made me a better version of myself.

  • “I don’t feel like I am worthy of all the good that comes into my life.”

    You’d be surprised, Cait, on how many people consciously or non-consciously share this feeling. Often others come first, with ourselves always coming last in our priority of things. I don’t know the deep-rooted cause(s) for this attitude. Perhaps we don’t (internally) give ourselves “permission” to love ourselves enough. Maybe that leads to insecurity, to not being able to not “sweat the small stuff” in our lives, to really see the “big picture” in our lives. All I do know is that when you gradually grow older (as I have) you sometimes eventually stumble upon the answers to these issues and what you could have done differently but by then you also realise that these answers often have come too late. Keep at it friend and continue to seek out the answers.

  • Cait, I’ve got one thing to say. YOU ARE WORTHY. All the bullshit, all the negative thoughts, all the doubts – it’s your ego trying to make you go back to what’s comfortable. Comfort zone is not living, it’s simply existing. Stretch your soul and mind every day. Challenge your ego. Tell yourself every day, twice a day, whatever it takes – that you are worthy. Tell yourself – I am worthy. It will take work but eventually, you’ll believe it. Big hugs to you! Loved this soul bearing post.

  • OK, this is going to sound really clueless, but as someone who goes to work for an employer, clocks in, and gets a paycheck, I was wondering: what is the difference between working freelance and being self-employed? How is the relationship with your clients different?

    • The difference is I don’t have clients anymore. Working for myself now = projects like the podcast, Mindful Budgeting planners, the book and a future course. :)

  • Remember all decisions you makein the past helped you to became the woman you are now, You must to do what you feel right for you in this moment of your life and I’m sure you’ll take right wasy. God bless you daily!!!

  • This is my dream – to be able to work solely on my own projects – but I’m not there yet. Best wishes to you! What an exciting step to take!

  • I love reading your posts. You often share things that are close to home for me. Look forward to more of your blog work now that you are quitting your freelance gigs. Thank you.

    • Thanks, Christina! I’m excited for the blog to be my #1 priority now, too. :)

  • Congratulations for entirely working for yourself! That is very exciting and I have no doubt he will be much happier and succeed in making up for lost income.

    Like you, I often wonder when the good times will end. I just can’t believe all the luck that is come about. So the way to get over it is to just appreciate every moment you have and know that one day things will change. But before that day comes, you’ll be able to maximize everything.

    • Thanks, Sam! And you’re right: it’s all about staying present and being grateful for each day we get to do this now. :)

  • Wow! This post couldn’t have come at a better time. I’ve just made a similar decision in my own life to stop pursuing a acting career, at least in the way I was approaching it. And when you wrote how a weight had been lifted and how more creation poured in – that resonated with my experience also.

    Sometimes we have to learn to put ourselves first and be brave enough to make wiser choices.

    • I’m so glad to hear you also felt the weight lift, Tom! Congrats on making the right decision for you.

  • Cait, I’m sorry for the pain and sorrow that brought you to this point but I’m happy for your brighter future. Of course you’re worth it! And you can’t help anyone else or do your best work if you don’t take care of yourself first–the whole oxygen mask on the airplane speech.
    So congrats and best wishes. You’ve got this.

    • That darn oxygen mask analogy – I hear it all the time, yet always forget about it! Thanks, friend. :)

  • Cait,
    I have just started reading your blog, and I appreciate your honesty about your journey through therapy and your grief. I am always going through some of that right now and it was reassuring to read this post. All the best,

  • That feeling of owing your employer/client I know that feeling. I’ve never been one to quit even when I’ve wanted to, mostly out of a sense of guilt. And maybe this one might just be me, but I always feel like I’ll put them in a bad spot.

    I’m glad you had the courage to take the next step in your life.

  • What an exciting step in your journey! So much hard work, persistence, and talent has gotten you to this point, and I’m sure that will carry you on to a successful period of truly working for yourself. And what powerful beliefs you’ve taking hold of and acting out of. Very inspiring.

  • Congrats on taking another step forward, Cait. It really sounds like this is the best option for you right now – and it’s great that you have the guts to go for it.

  • I love hearing your thought process on this. I just left my job and I’m going to start using your phrase – “Funemployment” – for what I’m doing next. I’ll be pouring a lot more energy into my blog and app and couldn’t be more excited.

    As other opportunities have come up, I have to keep reminding myself that every hour working on a freelance project or contract is time I’m not investing in what I actually *want* to spend time on. So, I’ve resisted the urge to take on other opportunities so I can give full-time blogging and coding for myself a real, legitimate shot.

    Thanks for the reminder – hearing your journey helps validate for me that I’m on the right path!

  • I really admire your courage, and I got a lot out of hearing about your process that led you to quit. Even though it came from a place of loss, which is tough, it seems like you knew it needed to happen. Your evolution since you became a freelancer is amazing. It sounds like you were set free by getting off the ‘comfortable’ government 9-5 (is it really a comfort or a curse).

    Thanks for sharing this with us. Your writing is super clear and your work has inspired me to consider self-employment, intentional living, and putting myself first with my time.

  • Just came across you and love everything you and your business are about. This article resignated so much with me as I’ve just made the decision to do the same. Good luck Cait and such a great read!

  • Thank you for your this! I’ve recently left my job to do freelancing as well and can already feel the itch to do more blogging and less freelancing. I hope to make the transition myself sooner rather than later.

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