I’ve been a blogger for about ten years now, which means I’ve been following people online for a really long time. It also means I’ve watched person after person quit their full-time job to work for themselves. It’s always touted as the “ideal” scenario because why would anyone want to work for a boss, have their schedule dictated by someone else, do work other people tell them to do? Isn’t being able to quit your job to work for yourself the ultimate freedom, the ultimate goal?
For me, the answer is an emphatic no.
I had what is called a quarter-life crisis in my mid-twenties when I was working at an unfulfilling job and feeling completely lost and confused about what I wanted from my career. I had never been particularly career-minded, never one to dream about rising through the ranks at a corporation or getting that corner office. I never had aspirations for management. I just wanted to do work that felt fulfilling, something where my skills could shine.
And yet, as a painfully shy, socially anxious person, I was terrified of every little thing when it came to work. I was scared of messing up, of taking initiative, of speaking up in meetings. I didn’t really know what my skills even were, much less what position they would shine in.
That was around the time when it felt like everyone was starting online businesses. There were podcasts devoted solely to “solopreneurship” and “building a brand.” It seemed like the only way to enjoy your life was to have your own online business. There were life coaches and web designers and bloggers. They were shouting from the rooftops how freeing it is to own your own business, to not “work for the man,” to have your own schedule.
And it started to feel a little condescending.
Because, truly, what is so wrong about working for someone else? Why can you only love your life when you’re working for yourself?
I called bullshit on that real quick.
I knew the answer to finding fulfillment in my life wasn’t by quitting my job and starting my own business. It was by finding things that made me happy outside of work (exercise, reading, joining a book club, travel) and getting really serious about finding a new job. I still wasn’t sure what skills I had or what kind of job I wanted. All I knew was that my degree was in communications, I had some marketing experience, and I loved to write.
And that’s when it happened.
I found it. The job that fulfills me. The job that doesn’t give me Sunday Scaries. The job that doesn’t define who I am by any means, but just makes me feel good.
This week, I’m celebrating five years at this company and I really cannot believe it’s been half a decade. When I started in this position, I was so scared. It took me two-and-a-half days to even approach the break room! It took me a week to talk to a coworker who wasn’t my boss. It took me over a year to find a friend. But from the minute I started, I knew I was at the right place. Five years later, I still feel that way. I still love what I do.
I still love to “work for the man.”
However, that doesn’t mean I haven’t thought about what it would mean to work for myself. I have. I’ve thought about being a full-time freelance writer, working on projects I sought out myself. I know it would take a while to get there. I’d have to spend months, or maybe even years, writing in the nooks and crannies of my life. Early mornings, lunch breaks, evenings, weekends. I’d have to hustle hard and throw my entire self into the work.
Man, does that sound exhausting.
Perhaps fulfilling in some way. And, I can’t lie, the extra money would be rull nice. But mostly exhausting.
There’d be no time for myself. No time for reading. No time for exercise. No time for friends. No time for naps. (I’d really miss napping.)
It’s not worth it for me. That side hustle life is not for me.
Right now, I have one single freelance client. She sends me work when she needs it. Sometimes, that means I’m spending every weekend writing. Sometimes, that means I go months without hearing a peep from her. It’s the ideal scenario.
And there are major benefits to being employed by a company. Health insurance, for one. Taxes, for another. Knowing that my job is steady and I will get a paycheck for the same amount of money every other week. Meeting new people, having a reason to take a shower and get dressed every day. Not having to worry about work coming in – I just take what’s given to me and do it with a smile. I’m challenged in ways that fulfill me, not in ways that stress me out.
So, I take your “working for yourself is so freeing” and raise you a “so is working for someone else.” I don’t think working for yourself is any more freeing than working at a job that fulfills you. I think they both offer their own levels of freedom and autonomy. It’s all about how you choose to view it.
I totally agree with you. My parents own a business and are STILL working at age 70 because it’s been so hard to transition it to my BIL. Their business is different than what many people our age are doing, though. It’s been a super demanding career as it’s a service-oriented business (my dad is an electrician). So we always had a business line that rang in our house and would ring at all hours of the day and night (because when your heat is out in ND in February, someone has to answer that call!). I saw how hard my parents worked and how little time off they took and I said NO THANK YOU. I much prefer to be an individual contributor at a company. I like having an HR department that handles taxes and 401k contributions and such and even though health insurance is still expensive, it’s less expensive than if I was self-employed. I don’t really buy into the whole ‘if you love your job you’ll never work a day in your life” line of thought. Maybe that it true for a very very small % of people but I think for most, work is always going to be work. I like my job/career but it’s still work and I definitely want to retire as young as we can. I don’t think there is anything wrong or shameful about ‘working for the man’. I’m all about you do you! But working for yourself is not superior to working for a company!
Totally agree with everything you wrote in your comment! There’s something so nice about having an HR department to take care of stuff like insurance, taxes, 401ks, and such. And I only pay $60 a month for health insurance, which is NOTHING compared to what self-employed people pay. I’ll take that ANY day of the week.
I have done both, and there are so many benefits and disadvantages to each option! For me, working in an office had 3 huge benefits: the health insurance/retirement stuff, being around REAL LIVE PEOPLE every day, and leaving my work at work. Working for myself has major benefits, too, though: I love doing only work I love/excel at (as opposed to in an office, where I was sometimes required to do things I HATE, like giving presentations), I love working in my pajamas/yoga clothes, and I love being able to work wherever I want. Plus, no commute! But I also recognize that I have had a really cushy time of it when it comes to freelancing, so I know it’s not the same for every one. The major disadvantages, for me, of working for myself are: TAXES (paying your own SS and quarterly taxes is a PAIN), feeling like you can never reject work or take a break because a dry spell might be right around the corner, and not being able to separate work from home easily. (And again, I recognize that I am really lucky to be on my husband’s health insurance, which is not the case for many freelancers. If it weren’t the case, that would be a MAJOR disadvantage.)
Yes, yes, yes to everything you’re saying. I can definitely see the upside to working for yourself and how it has to be great to do the work that most fulfills you. I feel like more and more companies, too, are seeing the benefits of letting employees work remotely on a regular basis, and I hope that trend continues because there’s nothing I love more than work-from-home days.
A few years ago when things were pretty bleak at my museum job, I ramped up my freelance with the aim of going out on my own full time within a year or so. I spent that spring and summer working my butt off- I was at a computer from before work til late at night, and I was hustling like crazy to save cash to go out on my own. I was exhausted & while part of it was because I was working full-time too ( though to be honest I was working on freelance at my day job a lot), I realized I didn’t have the long-term hustle in me. My Dad owned his own business as a graphic designer and I saw how for over a decade he was constantly putting himself out there, meeting people, and so forth, and I realized it wasn’t for me. I liked the random freelance for the extra cash, but realized if it was my sole source of income, it would make too anxious and worry all the time about money coming in, insurance, taxes, and so forth. I actually ended up taking a big break from freelance for about a year too after that because it also made me realize I was neglecting my personal journal writing, my blog, and the book I’ve been slowly working on too!
Yes – the hustle life is not for me! And it’s something you have to constantly do, no matter how successful you are as a freelancer because you could lose a big client or have a slow month. I like not being in charge of stuff like that. While I long for a more flexible work schedule, I also really enjoy the benefits of working for someone else.
YES YES YES, THANK YOU SO MUCH FOR THIS. I feel the same. “Why can you only love your life when you’re working for yourself?” YOU CAN. I have so many other feelings about this, but “YES YES YES” really sums it up.
Hahaha, I am so glad this resonated with you! It’s been on my mind to write about this topic for awhile.
Amen! I am so with you on this. I feel like I am constantly being shamed for working ‘for the man’. But you know what? I got the same paycheck every two weeks (with a predictable pay increase schedule), I got healthcare for myself and Eva, I got benefits, I got job security, and I got a nice retirement to look forward to. Yes, being in the military I may have to deploy which means working 24/7 BUT the trade-off is so worth it. Right now I get to create my own schedule, take care of family matters, work out, go to appointments and take care of any other business whenever I please as long as I get my work done. Yes, sometimes I may have to take my work home but this rarely happens. It’s so so worth it to me!
Yes, the trade-off is absolutely worth it for me! I just don’t have it in me to constantly be hustling after work. I like the predictability of my day job and my benefits and my salary. It gives me room to explore other hobbies and take care of me at the end of the week!
I couldn’t agree more. I don’t know when freelancing became something EVERYBODY should aspire to…. I mean, sure they’re always people who have businesses and are self-employed, but most of these jobs are not even that glamorous and wouldn’t you want to go home at 5 pm and not think about work for a second. I much prefer working for an employer and doing what I love in my free time, thank you very much.
Agreed… working for yourself really became this echelon for everyone to aspire to, not taking into account that not everyone WANTS that. Some of us really enjoy working for a company and having a job to go to every day. I don’t think my anxiety could handle having to hustle after work every single day! No, thanks.
I LOVE LOVE LOVE that you have a job that you find fulfilling and get to have outside interests. I think that is ideal and AMAZING! And amen to working for the man. I work for the government and my husband has his own business and I would NEVER want to do that. I want work separate from personal life, and I WANT a personal life. So I am with ya.
Congrats on five years!!!
Thank you! It’s definitely easier to “work for the man” when I find my job to be fulfilling and satisfies my needs. It would be another story if work was super stressful! And yeah, it’s probably a constant struggle for people who work for themselves to separate work from personal, and I’m glad I don’t have to worry about that.
I LOVE LOVE LOVE that you have a job that you find fulfilling and get to have outside interests. I think that is ideal and AMAZING! And amen to working for the man. I work for the government and my husband has his own business and I would NEVER want to do that. I want work separate from personal life, and I WANT a personal life. So I am with ya.
Congrats on five years!!!
Yessss, thissssss. All of it! Once upon a time I thought I wanted to be one of those “professional bloggers” and then I realized that requires A LOT of work and hustling. I like clocking out and not having to think about the next big thing. Maybe that makes me sound lazy, whatever. Like you said – I just want to do work that I find fulfilling and spend my free time doing things I enjoy. My family is full of entrepreneurs so I feel a little bit pressured to follow in their footsteps and one day maybe I will. But for now I’m enjoying the freedom and peace of mind that comes with working for the man.
So much hustling! I am not built for that kind of life. I like having my free time be solely for the things that make me happy and letting my job stay at work. And I also like that I don’t have to worry about “marketing” myself on this blog. I have the freedom to write whatever I want, whenever I want, without worrying about sponsors or building a brand. There aren’t too many personal blogs left anymore, and I’m grateful my little corner of the Internet is holding on strong.
Ahhh I love this post!! I really do enjoy doing freelance work – mostly for the extra cash and it’s been an awesome use of my brain during maternity leave. However, I am also really happy to be going back to a full-time job with a steady paycheque and what I think is the best perk of all – extended health benefits and pension / RRSP.
However, since having a child I do wish I could work LESS and make the same amount of money ha ha. I really hope that one day I am able to get to a place ‘working for the man’ where I can have a more flexible schedule. My ideal would be 3 days per week in the office and 1 day per week at home… but I’d also like to still make my f/t salary working those 4 days a week 😉 We’ll see, maybe one day!
Isn’t that the ultimate dream? Working for the man so you don’t have to hustle yourself, BUT still having a flexible schedule. And yeah, I’d gladly work 4 days a week if I could make the same amount of money, hahaha. Hopefully, more jobs begin to understand the need for a more flexible schedule and work-from-home opportunities.
This is something I’ve thought a lot about and I agree – I don’t really want to work myself. Would it be awesome to travel all the time and be able to have a more flexible schedule? Sure, of course. But I also would feel the weight of that all the time, the anxiety of knowing that I have to figure out ALL OF THE THINGS or I won’t make it on my own. I need the security of working for someone else.
Exactly! And I think we can have flexibility with our schedules when working for someone else. I feel like more and more companies are opting for unlimited PTO and work-from-home opportunities because they know how important that is for our generation. But even still, there is way more freedom in working for someone else than working for myself because the hustle life is just NOT for me.