Give Me Back My Five Bucks

Why I don’t want to be self-employed

IMG_1770I was 29 when I quit working in a cubicle and became self-employed. It was a huge step, and I was excited to experience the freedom of setting my own schedule, working wherever and whenever I wanted, and creating a lifestyle that I had always dreamed of. I was eager to test myself to see how much I could accomplish on my own. Plus, I was moving to Germany for a year with my boyfriend, and that just added to the excitement.

My passion for my new freelance life was further fuelled by the fact that so many of my friends were either already working for themselves, or aspired to one day work for themselves. I felt like I had finally achieved something important: after two very difficult years of working 70+ hours/week at both my full-time job and freelancing, I had grown my freelance writing gigs and this blog from nothing, into something that I could actually make a decent living from. I had steady clients in place, and a good amount of extra freelance work rolling in.

However, after a year of doing my own thing, I knew that being self-employed wasn’t the right fit for me … which was interesting to learn about myself after years of wondering if I could make it on my own.

Although the year I spent freelancing proved that I have what it takes to work for myself if I ever wanted to go that route again, I am much better suited working for someone else for the rest of my career. Freelancing and self-employment isn’t for everyone, and I honestly think it’s a lifestyle that not many people can handle (no matter how much they dream of being their own boss). I’m constantly impressed by my friends who are thriving as freelancers because I know it takes a special kind of person to make it work.

Here are four reasons why I left freelancing and went back to my cubicle (and none of it had to do with not making enough money!):

1. Freedom

Yes, freedom! So many people talk about wanting to have the freedom to create their own schedule, and not feel like they’re chained to their desk. Well, I’d rather be chained to my desk for 8 hours a day than feel like I’m chained to my own laptop and smartphone 24/7. Honestly.

Sure, I got to work whenever I wanted, and travel when I felt like traveling. But as it turns out, I was kind of a demanding boss on myself. I always felt pressured to work harder, and when I wasn’t in front of my laptop? I was either checking my emails and looking at social media, or worrying about checking my emails and looking at social media. I didn’t want to miss any new opportunities, and it drove me crazy. It’s pretty horrible to feel like you can’t be without your phone, ever. I had major anxiety, and started to lose all sense of balance. My work consumed me, no matter what kind of schedule I tried to implement. I wasn’t practical, because I was too scared not to hustle as much as I could.

So even though I was only doing actual work for 30 hours a week as a freelancer, I never felt like I could step away. Whereas a full-time job brings me the freedom to leave work behind. After 5pm, I don’t have to worry about projects or clients or income targets, and my evenings and weekends are mine to enjoy however I want. Life is short, and I’d rather hold hands with my boyfriend in the park after work, than sit in front of my laptop trying to hit a deadline.

2. Time Off

I used to think that if I became self-employed, I could take as much time off as I wanted to. But it was actually pretty hard to go on vacation and complete unplug from the outside world. Sure, I traveled a ton, but the problem with being your own boss is that when you’re on vacation, you’re not getting paid. Plus, most evenings (and yep, sometimes during the day) when I was on vacation, I was checking e-mails and following up on work-related admin stuff, or stressed out about a client reducing their budget – none of which were relaxing!

My old corporate jobs allowed me two or three weeks of vacation, which obviously was not enough time for the amount of traveling I wanted to do each year. I yearned for more time to go adventuring, and thought freelancing was the answer. But what I didn’t realize was that perhaps it was just the industry I was in that was limiting my freedom.

I love the industry that I’m in now because of the flexibility it provides when it comes to time off. I feel lucky in that every little bit of time I work above and beyond a normal work day gets given back to me – which works out to having seemingly unlimited vacation time. Last year I took 6 weeks of paid vacation, and this year will likely be around the same. Maybe even a bit more. And best of all? I don’t have to worry about anything related to work while I’m gone.

3. I am not special

I have a very good idea of where I stand in the personal finance world. I’m an average writer with an average get-out-of-debt story. I don’t have any unique skills, and I’m not special. But what I do have is an above-average passion for personal finance, and the desire to help others. And that’s why this blog has been around for almost 10 years.

There are so many other people who have the self-employed thing dialed in. They know exactly what to do and how to do it, and if I’m being honest, I don’t have that fire in me. When I used to tell people I was self-employed, they would tell me how amazing that sounded, and how they wish they could do the same sort of thing. But in reality? I was craving stability and a normal 9-5pm work week. :) Which brings me to my next point…

4. Stability

The ability to work for yourself opens up the doors to limitless streams of income, and I will admit that felt super liberating. But I’m a natural worrier, and even though I had steady contracts which gave me a steady income stream, having the rest of my income fluctuate caused my anxiety to skyrocket. Some weeks I would bring in thousands and I’d feel so confident. Then there were other weeks I’d make nothing and I would start to panic. Everything evened out over the course of the year to provide me with a perfectly livable income (that was actually more than my previous full-time job provided), I couldn’t handle the ups and downs with grace.

My desk job provides me with the stability I crave. I know that every two weeks, I’ll be getting X amount of money. It’s something I can count on, and I need that feeling of stability.

Being self-employed is a terrific option for some people. I have plenty of friends are are self-employed rock stars! But it’s a lot less glamorous and a lot harder than you might think. I know myself well enough to know this now, but it took me half a decade of freelancing and a full year of being self-employed to really understand it.

Have you ever wanted to work for yourself?

Author: Krystal Yee

I’m a personal finance blogger and marketing professional based in Vancouver. I’m a former Toronto Star (Moneyville) columnist, author of The Beginner’s Guide to Saving and Investing, and co-founder of the Canadian Personal Finance Conference. When I’m not working, you can usually find me running, climbing, playing field hockey, or plotting my next adventure.


  1. Thanks for a different perspective. I work full-time but run my blog as my side hustle, and I have always dreamed of working for myself! Your story definitely proved some solid points of the pros and cons, so thank you!

  2. Michelle says:

    Love this! While I absolutely love working for myself, I know that it’s not for everyone. There are so many positives and negatives to both sides.

    Plus, work/life balance is something that I am currently working on. Like you said, it can be extremely hard when you work for yourself.

  3. SP says:

    I’m with you here.

    My professional skills don’t translate well to freelancing (consulting would be possible).Compared to my job, my hobbies aren’t a high enough value for me to invest time into trying to transform into freelance. And I’m not that special in them :)

    The other reasons too: stability, freedom from being the boss, paid vacations, and an opportunity to work on things that a single person couldn’t do (and that I don’t have the credibility to get hired for on my own.)

    • Krystal Yee says:

      Oh yeah, absolutely agree with you on that last point. Even the biggest projects I did while freelancing was on such a small scale that I really started to crave projects with big budgets, or high profile events, or being on a team. I also missed collaborating with others on a daily basis, and even just the social interaction of being around people working towards a common goal. :)

  4. This is a really good post Krystal. I am self employed now and I’m planning to stay that way, but MAN DO I MISS the end of the work day when I know that I don’t have to think about it again until the next day. Not to mention the weekends!

    Now, I have to say working for myself is better than working full time and trying to side hustle online at the same time. That was just bananas. Not having the stable income though certainly adds to the anxiety.

    I’m always questioning if I made the right choice. I think I did, and I hope it eventually gets easier over time but right now it’s quite the challenge.

  5. I totally agree Krystal. Sometimes I wish I could be self-employed and have all of my time and schedules as my own but I once took a job where I worked remotely so it was pretty similar. I could do what I wanted when I wanted as long as I was hitting my targets. Honestly I got lonely and cabin fever-ish. While I sometimes enjoyed being able to get up to work at 7 and then take a two hour break if needed, it gets old after a while.

    • Krystal Yee says:

      Yeah, I wasn’t prepared for the loneliness! I’m an introvert so I didn’t think being by myself all the time would be an issue, but it totally was. Turns out I like the variety of being in an office – with the option stay quiet and do work in my cubicle by myself, or chat with my co-workers, and even just being around people. The environment was a lot more dynamic than me sitting by myself in Starbucks or the library for hours at a time. :)

    • It gets old and BORING! Working with great people is fun. I think work is awesome if you don’t really need to work. Then you can be more choosey on who you want to work with/for. It’s a win!

  6. J. Money says:

    Love it!!

    Way to keep it real up in here!

    I’d totally go back to working for someone else too if it made me happy – why not? You always have a boss whether it’s one main person or your clients/blog readers/Google/whomever and you’re SPOT ON about the “freedom.”

    Good for you for a) giving it a shot, and b) not being afraid to jump back into the 9-5 world though I’m sure people will give you $hit for it… You accomplished something 99% of the world won’t ever do! Well done!

  7. Very interesting perspective – I’m definitely one of those people who assume that working for yourself is THE way to go but just like anything else if it wasn’t without its downs for every up everyone would strive to do it. I think a lot of companies are starting to open up to providing their employees some flexibility which is a nice balance for those who want the structure of a 9-5 but still crave some independence. Remote offices, work from home days, 4 day work weeks, etc.

  8. I can totally see both sides of this argument! I’m just about to jump into the freelancing pool, but I know it’s the right choice. While I would prefer a stable income, I believe that I will see more benefits in maintaining my own schedule and projects and knowing that the money will be there eventually.

  9. NZ Muse says:

    NOPE. Never have. I also agree on the whole aspect of working on bigger projects and making a difference that way.

    I can’t lie, often I read about bloggers making a killing online and feel a pang. But having freelanced a lot over the years (including while traveling full time) I know already it’s not for me, even though the flexibility would be nice. I’m also terrible with boundaries and I would be such a workaholic.

  10. Kate says:

    Yes! Fantastic post! My boyfriend and I are currently in the midst of a year abroad and before we left Canada I had grand plans of working for myself, freelancing and just loving it. But, after a few months I realised it just wasn’t for me. It was a bit hard to admit that at first, but now I know it’s just being true to who I am.

    Kate |

  11. Jack says:

    This article was really good perspective for me right now. I’ve been really unhappy and unfulfilled at these 9-5 jobs and I’m currently trying to figure out what I want to do. I worked really hard to pay off my debt and I live a pretty simple life so my expenses aren’t too high. I’m 28 so I feel like it’s still an ok time to take a chance on something.

    I have a side hustle that I can work at more often to cover all of my expenses, which would give me time to work on my own projects.

    Worst case scenario, I hate it, and I go back to office work. But I figure I’ll never know until I try!

  12. Self-employment and freelance is best when you’re already established or have a partner who works full-time to help cover the peaks and valleys in earnings. Try qualifying for a mortgage on your own when you’re self-employed. Not easy.

  13. I had never considered the downside to entrepreneurship. I would have thought that the freedom to create your schedule would trump all other reasons but as always, there are other things that I’m not considering!

    I haven’t thought of working for myself yet. I want to establish contacts and prove myself before I go do so which is why I am starting to work for someone else soon!

  14. Aaron says:

    Kudos to you for giving it a go Krystal. I don’t know many who work for themselves that aren’t putting in well over 40+ hrs a week plus the burden of having to get that next client. That’s quite a tradeoff when working for the man often offers you the freedom of limited work schedules + stable pay.

    Bless you for trying!

  15. Thanks for sharing your thoughts. I totally understand the “Time Off” portion of your post. There’s this urge to always work, because no work equals no pay as a freelancer.

    Perhaps the secret really is to be a hybrid freelancer? If you can generate 70%+ of your income online in a semi-passive way, and the rest through freelancing, then the urge to always work isn’t as much since you’re still getting 70%+.

    When I’m traveling or on vacation, I just make sure I continue to publish at least 3 posts a week on Financial Samurai. And if you can get the majority of your traffic via search, then even the pressure to post the same schedule fades too.


  16. Derek says:

    I can identify with everything you’ve said here.

    Good luck in the future, where ever your path leads you.

    I’m sure you will do very well and be just fine.

  17. ZJ Thorne says:

    This is such an important thing to learn about yourself. Structure can be a very helpful add-on of the traditional work environment.

  18. Many thanks for the confession.
    I totally agree personal business and freelance is not for everybody. It is high risk with potential high rewards, but it might go either way.

    I am glad to see that you have tried it and had courage to share your ideas and feeling about “freedom”. Was it a difficult thing to get back to work for somebody?

    • Krystal Yee says:

      Yeah, actually it was a little bit. Some people kind of had an “I told you so” attitude about full time blogging… and didn’t believe me when I told them I wasn’t going back because I needed the money. :)

      Also, I personally felt like a bit of a failure too… it took me a while to be ok with it. But not everyone has what it takes, and it was humbling to realize that I was one of those people.

  19. TJ says:

    What industry did you go into to after you decided freelancing wasn’t for you?

    • Krystal Yee says:

      I went back into marketing (what I went to school for) but in the architecture and engineering industry. :)

  20. Wow, what a story. I’ll say this, good for your for taking the plunge and figuring everything out. The only way you will know if the life for you is to go out and try it. You did it, you lived the “dream” of many bloggers, and found out it wasn’t for you. Oh well, now it is time to move on and begin the next chapter of your life. Thank you so much for sharing your story with us!

    Bert, One of the Dividend Diplomats

  21. Julio says:

    Indeed, entrepreneurship is only for the brave. That’s why socialists hate our guts. Hillary and Bill, for instance, could never open a business in their lives so they have chosen to milk the taxpayer and business owners thru government corruption. Enjoy your “Joshes” and “living abroad,” while the rest of us carry the planet on the back.

    • Sean says:

      No “Julio” or whatever your name really is,
      no one is milking anyone except you stealing time and attention spouting your BS.

      Cretins like you are worthless and a dime a dozen.

      By the way, “socialists” or whoever you are talking about do not hate entrepreneurs at all.

      Some people simply wish to have life run safely and correctly.

      I see a lot of GOP leaning people moan about how “regulations are hurting business” when they really mean “I could make more money without these safety rules, without these labor laws” and cheat the world at large in the guise of “fair competition” when what they really mean is “survival of the fittest and to hell with the rest”.

      Of course a short sighted fool might be in that position and decide “I’ll always be on top, the successful never fail” and screw safety nets and everything else to live in a personal “gilded age” like the robber barons of yesteryear.

      By the way “carrying the planet on your back” doesn’t hold water either. Most of the people in the GOP seem to never want to pay taxes.

      they come up with nonsense like “Barstool economics” morality tales where amounts of money are tossed around to make their own personal case.

      How about reality:

      Middle class might lose 30-40% of their INCOME TO TAXES while the rich whine about paying anything at all.

      You are a useless clown.

  22. Anonymous says:

    This is so true, I am self employed & crave the steady income of being an employee. It is great for security & definitely leads to less stress in that regard. I’ve recently started my blog as my side hustle & although I have high hopes for it, I intend on it remaining a side hustle :-)

  23. deleted says:

    P.s Francesca at From Pennies to Pounds!

  24. Jaymee says:

    Krystal, as I’m reading this, I felt myself breathing a sigh of relief! It was almost like someone was giving me permission to not want to be self-employed or become an entrepreneur you know?

    Over the years, I picked up that I won’t become wealthy unless I have a business of my own or work for myself and that idea makes me nervous. My job as a nurse is as secure as it gets I think and I’ve enjoyed the stability, lack of worry after my work is done and being able to leave all my work at work when I go home. I worried that if I stayed in this place, I will never be financially free.

    So it’s great to hear this from someone who’s experienced both and realize that it’s okay to keep my job for now and hustle some more in my spare time. I don’t think I’m cut out to be self-employed at this time and now I feel better owning up to that. Thanks Krystal!

  25. Reader says:

    Krystal I enjoyed your article. I am lucky I didn’t have to experience on my own what it’s like to be self-employed because my parents are the ones. I grew up thinking I never wanted that kind of life. They were incredibly successful at some point, and the business still continues…it’s been 50 yrs. But they scarified in a great deal – family, marital qualify, and my father’s health. MY family is estranged as their business always came first. I appreciate the risks they took and work ethics they displayed. But you’re right, if you own business, the business will pretty much dictates your life. My dad was unemployable in a corporate setting at an early age. He’s in Japan, and back in the old days, if you “derailed” from one corporate job, you’d be considered finished – “unhirable”over there. So in a way, self-employment was only way for him. Luckily though, it perfectly suited for his natural persona.
    I’m in between my jobs now and having an incredibly tough time to find another employment. I’m so depressed because I hate the thought of that path…a possibility that self-employment could be only way for me, and trust me, I don’t want that.

  26. Trisha says:

    This brings up things to consider for sure. I like how you’ve mentioned that not everyone is cut out for entrepreneurship and that there can be stability and freedom in working for a company. For those that can and want to work for themselves, great! For those that can’t or don’t want to, it OK!

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