Why I Traded in “The Dream” to Work for Someone Else


Sometimes the dream doesn't play the way you expect it to

by Stephanie Kaloi, Content Manager

apw-squarespacewoman sitting on a tree with a camera

Eight years ago, I was a newly pregnant college student in my last semester at university, working toward a dual degree in sociology and global studies (and a minor in art history, no less). I really wasn’t sure what exactly I intended to do with the degree, really, except maybe talk about art in fabulous international cafes while studying all the people who walked by. So when two friends of mine started a wedding photography business, I thought, “Oh hey! I wonder if I could do that, too?” Better yet, I thought that if I could do that job, I could also be home with my baby when he or she was born.

working for yourself isn’t everything

Fast-forward a few months and it turns out that, yes, my lifelong interest in hobbyist photography meant that I had developed a bit of an eye for capital-m Moments. My habit of following people around and taking notes with my eyes (aka being nosy as fuck) meant that I was good at finding those moments without people realizing I was there, and both of those skills are crucial parts of being a wedding photographer. A few months later, another friend asked if I would help her shoot a mammoth of an eight-hundred-guest wedding, and after that we started our own business.

The first few years were amazing: We shot so many weddings in such a small amount of time. Navigating the world of business was tricky, and we had our fair share of disputes (see also: having a business partner is hard), but we dove into the world of weddings, loved it, and it loved us right back. In those first three years, we made enough money to support ourselves and our families and travel a bit, and we met countless incredible couples. Additionally, I took on various editing and writing jobs in that time period, and though I wasn’t making hundreds of thousands of dollars a year (and sometimes things were still tight), it was enough to support my family while my husband dabbled around in different jobs, and it was enough for us to get by.

That’s kind of the dream, right? At least, it is if you read any number of articles online, all decrying the idea of working for anyone other than yourself. But the truth is, for every time I’ve read that the only way to be fulfilled by work is to be your own boss, I have a real-life example of how working for someone else has been more fulfilling.

sometimes “the dream” looks different in reality

Then, a year ago, we decided to move from Oregon back to the southern US, where we live today. Six months later, I got an email from Meg (yes, that Meg, the EIC of APW, who is also a longtime Internet friend—we met through another website that I worked for), asking if I would be interested in working three to five hours a week to help APW out during her maternity leave. As I have always aspired to work on the Internet (seriously, since I was fourteen in 1999 and that first AOL CD landed in my mailbox), I jumped at the chance—plus, three to five hours a week in a field I had plenty of experience with? That’s not much. So I added it to my workload, happily filling in when needed, and getting to know the APW team of Najva, Keriann, and Maddie in the process. We completed our move, and when Meg came back from maternity leave, she asked if I wanted to stay on. My husband didn’t have a job yet, and #workontheinternetgoals persisted, so I said yes. Color me surprised (and so pleased) when three to five hours a week turned into ten by year’s end, then fifteen, and then twenty… and now I find myself on track to be full-time with APW early next year.

Somewhere between hours ten and fifteen, I realized that, OMG: I kind of loved this working for someone else thing. And by kind of, I mean a whole, whole lot. But every time I talked to someone at APW about taking on more hours, I would get a little nervous—what if the Internet mysteriously vanishes? What if APW folds? What if I hate being part of a team, or I don’t like being on the hook for content and hours?

the hard knocks of self-employment

I think most people who go into business for themselves do so because, more than anything, they crave that special kind of freedom that self-employment offers. Even when it’s stressful as all get-out, and you’re pulling fifty-hour weeks to get everything finished, you know in the back of your mind that a few weeks later, you’ll be solely in charge of how you spend your time again. Even when you’re paying taxes and kicking yourself for not putting away the 30 to 40 percent you should have to pay the IRS right away (just me?), you know that payment plans exist and the IRS still likes you as long as you get them their money. Even when you have those random nights where you’re up until 2 a.m. editing because your kid just needed you to hang all day and all night, you realize that, oh hey: I have the luxury of being able to hang with my kid all day and all night (you know, if you want to).

I know I was definitely one of those people: Self-employment sounded like the dream because it would mean I was responsible for me, and that’s it. It also meant that I would have all of this time to go to those ballet classes I kept wanting try out (except I never actually did). What I didn’t realize about working for someone else, or at least about working for someone the way I do now, is that there’s a special brand of security that comes with not having to make all of the decisions yourself. I didn’t realize how light my shoulders would feel when every major—or even minor—business decision wasn’t on me. I didn’t realize how cool it is not to be concerned with budget, not having to drive three hours one way for a wedding every weekend, or how cool it is to know that if I have my hours as 1 p.m. to 4 p.m. on a Thursday, that’s all I have to work, and then I can walk away. The idea of leaving work at work was foreign to me until I got a boss, and now? Guys, I love leaving work at work.

I also love that in a culture where it often feels that we are inundated with articles and commercials and movies and even billboards that tell us what we need to do is go out on our own, start our own business, run our own show, I’ve found a lot of contentment while working for someone else. Sure, I know I’m expected to be online and available for a certain number of hours a week. Yes, I answer to one or two people at any given moment, and yes, there have been days where I would rather be outside instead of poring over endless comments… but every time I see a piece bemoaning not being your own boss, I find that I no longer agree. Sure, I’m not convinced I would fare well in a strict corporate office environment (especially not those that still place heavy restrictions on colorful hair and tattoos), but I’m responding quite well to knowing that it’s not all on me, all the time.

When it comes right down to it, I get paid (well, even!) to regularly write about my opinions on my favorite playground (the Internet), and then other people, who are generally kind, intelligent, and thoughtful, tell me their opinions on my opinions. And then we go back and forth, round and round, and I love it. At the end of any given work week I am often tired, run down, and looking forward to pouring a hefty glass of Tempranillo, but I’m also giddy, excited to talk about what I’ve been up to, and ready to hit the ground running on Monday. Let’s just say that when I was shooting thirty to forty weddings a year, I didn’t exactly greet Monday with quite the same gusto.

looking to the future

Of course, I do still have my photography business, and I’m even still booking weddings. The difference is that I’m not pouring money into advertising, and I’m not aggressively marketing. I have a steady paycheck that comes twice a month, and now I can choose to shoot up to five weddings a year (or maybe ten). I’m not sure if I’ll ever be fully comfortable with the idea that the Internet is truly my work space (seriously: what if it really does mysteriously vanish?!?), but… I’m looking forward to trying to get there.

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This post was sponsored by Squarespace. This year we are partnering with Squarespace to bring you a series of career conversations about what it means to be a woman with hustle in 2016. If you’re in the market for a new job or looking to explore your options, one of the best things you can do for yourself is create a home online where you can show off your work in the form of a portfolio site, an online resume, or another hub where you can display just how awesome you are. Squarespace provides the creative tools that make it easy to build your online home beautifully, even if you’ve never made a website before and have no idea where to start. In conjunction with our career series this year, Squarespace is offering APWers a 10% discount on your first purchase when you use the code APW16 at checkout. Click here to get your website started today with a free 14-day trial from Squarespace.

Stephanie Kaloi

Stephanie is a photographer, writer, and Ravenclaw living in California with her family. She is super into reading, road trips, and adopting animals on a whim. Forewarning: all correspondence will probably include a lot of punctuation and emoji (!!! 😊 🎉 🎉).

Staff Picks

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  • Laura C

    Self-employment seems like a nightmare to me. Being the one to hustle (beg) for business AND deal with any and all crap from the client AND have to follow up (beg again) to get paid, knowing it’s likely to be late and maybe a fight? Ugh. Seems like a commentary on how terrible employers are assumed to be that that sounds preferable to working defined hours for defined pay and having a defined set of hassles that fall on you while other people deal with other potential problems.

    Of course there are differences in personality and some people just thrive on selling themselves and constantly hustling. But I feel like half the people I hear from talking about going into business for themselves, what they’re really saying is that they’re sick of being exploited by other people, so they’re going to try being exploited by themselves for a while. (And of course they’re still being exploited by their clients, but it’s easier to pretend it’s all their own choice.)

    • stephanie

      By far, the hardest part for me has been making sure people pay me when they say they will. Not everyone does it, but it’s really hard when someone sets a due date themselves, and then two weeks go by and the money hasn’t been paid. I don’t think people often take a second to think about how they would feel if their income wasn’t delivered when it was supposed to be. I think self-employment is so amazing on so many fronts, but after eight years, have yet to come up with a surefire way to always get paid when payment is due 100% of the time.

      • Rosie

        I don’t think there is a foolproof way – the best I’ve found is to try and arrange my finances so that I don’t rely on people paying on time, which makes it less stressful.

        • stephanie

          Yep, that’s always my goal, it’s just not always feasible throughout the year.

    • NotMotherTheresa

      Ugh, yes! I went through a period of self-employment, and having to beg to get paid for the services provided was one of the parts I detested! I hate hassle, and I hate confrontation, so the last thing I felt like doing after a long day was calling people up to argue with them about how much they owed me and when! In all, I left thousands of dollars on the table from simply deciding the trouble wasn’t worth the $400 I was going to get out of the person.

  • Sara

    While I have a fantasy of owning/running a coffee shop, practical nature of owning a business sounds terrible to me. More power to all of you that are self-employed because that’s so so hard. But I love to travel and am such a high stress-high anxiety person that if I were in control of my own business I could never go on vacation and relax. I would constantly be obsessing over what was going on at the store, or on the phone the whole time. I would have to be there all day, control freaking out all over the place. I love turning off my computer and being done for the day, the weekend, the week.
    I feel like I was created to be second-in-command. I don’t want to make the hard decisions, but I’m great at figuring out the most efficient and practical way to execute those decisions.

    • stephanie

      I feel you on travel! I am in what feels like a minority of wedding photographers who don’t particularly love to travel for work. I’m always happy to do so—and I love the couples who have flown me out to shoot their weddings—but I spend the day or two before the wedding thinking about it and the days following worrying something will happen to the photos, my hard drive that they’re backed up on, or any piece of equipment. I have been lucky in that I have been able to turn work trips into trips for my son—this summer I brought him along when I went back to Portland to shoot, and then used that money to take us to LA, Universal Studios, and San Francisco. So it’s been SO GOOD for that, but it’s also… I don’t connect travel and work together, and don’t like being responsible for wedding photos when I’m supposed to be taking a break.

  • SarahRose472

    I feel this so hard. My husband started and ran an high-growth business in the past few years while I was still in school and had no income…all the responsibility, all the time, on him. Even for someone as passionate as he was about running his own business, it has worn him down and made him start to long for a steady paycheck, where the buck doesn’t always stop with him.

    I always knew that wasn’t for me, but seeing this process up close has made me feel like I’m actually pretty ok with CEOs getting paid way more than all of the rest of us because it’s such an enormous mental/emotional burden to have the final responsibility for solving shit, for keeping the company profitable, for sustaining your employees’ jobs.

    • stephanie

      Oh man, being the one who supports your family is such a taxing thing! I mean, I love photography and I loved when I was shooting so many weddings a year, and I even love that it meant my husband was able to figure out what he really wanted to do (and he’s now in school for it and working in the field while a student).. but it was so emotionally taxing. Steady paychecks are a remarkable, magical thing that I’ll never take for granted.

  • Kara

    I crave security and structure (hi I’m an ISTJ), and the thought of owning my own business is just not something that interests me. I’m also highly risk adverse, like I do risk analysis all day every day. Sooo working for myself is not something that interests me.

    More power to those that enjoy working for themselves, but there’s still nothing wrong with working for someone else who genuinely cares for your well being.

  • Sarah E

    I constantly go back and forth on whether self-employment– even just as a side hustle– is right for me. My job, which was dreamy for the first 12-18months, has gotten way more stressful, thanks to company growth (that doesn’t directly affect me, but takes my superiors’ attention). I’ve never been with a job this long, so right away I start questioning “Should I stay? Should I look elsewhere? Has this run its course?” I’m pretty sure I can see this through to the next phase, but the rose-colored glasses are off.

    In terms of self-employment, though, I think about how I work best, and it doesn’t jive. I’d love to have the control over decisions, but I work best around others, not at home, and I’m still learning how to impose my own structure on the day. Marketing is one of my weaker points, so would I even be willing or able to drum up business? Idk. It’s hard to tell the difference between knowing my weaknesses or just doubting my abilities.

    • Rosie

      I’ve been self employed for 4 years; when you’re a one person business you have to do every role in the business, and some of them won’t be your strong points. I think what you need depends on which industry you’re in: I’m pretty shoddy at marketing but I have long term clients so I don’t need to find new business very often. In some industries I probably wouldn’t get away with it!

      • stephanie

        I was coming here to say this—I’m not great at marketing (mostly because I just don’t… care), so I’ve had to seriously hustle to counter-balance that as a photographer. I can definitely imagine there are several industries in which marketing isn’t as crucially important, because you’re not having to constantly pull in new people.

    • Her Lindsayship

      “It’s hard to tell the difference between knowing my weaknesses or just doubting my abilities.” Yup!! I feel this too. I know I wouldn’t want to start a business on my own, but I have some interest in doing so with a business partner who would hopefully balance out some of the weaknesses.

    • Kaitlyn

      I feel like the first part is me in a nutshell! I would love love love to own my own small business (I keep describing it to my fiance as wanting to be “a pillar of my community” hahaha), but can’t decide if it’s right for me. I think it’s more that I’m scared than anything and trying to figure out how I’d fit in a side hustle with my day job and horrendous commute.

    • NolaJael

      Learning to self-promote can be a huge hurdle for the newly self-employed. Some people get over their fear and embrace it. Some people just can’t and their businesses wither and become that dreaded first year statistic.

      • Sarah E

        For me, it’s just distaste for learning enough so that I don’t feel I’m just shouting into the void, but actually reaching potential clients.

  • sofar

    My husband comes from a long line of entrepreneurs and business owners. They’ve all found overall success, but at a huge cost sometimes.

    Sometimes, one of his cousins/uncles/dad will say something like, “You’re just a paid slave if you work for someone else.” And I’m sitting over here thinking, “OK well it was my steady desk job and every-two-weeks-like-clockwork paycheck that paid our rent for six months while my husband was facing some business setbacks a few years ago.”

    So many of his relatives will ask me when I’m going to quit my job and join him in his business, and I’m like, “Uh…. NEVER. I enjoy getting paid like clockwork and knowing my hours in advance, thanks!”

    • Lisa

      Most of my friends are performers, and they’ve cobbled together 3-4 jobs either teaching, performing, or working in service industries. When I was graduating with my degree, I realized that I actually like knowing where my money is coming from, how much of it I’m going to have, and that it will show up on a regular time frame. Also, employer-sponsored health insurance. While I wish I was performing more, I don’t envy a lot of their cobbled together schedules and the constant juggling act of managing them.

      • nutbrownrose

        I just moved, and finally got a job I didn’t know was exactly what I want to do 6 months ago, and I still have to work 4 jobs to make ends meet. Because this perfect job that can lead to an even more perfect job, and get me contacts in my hopeful industry, only pays 17 hours a week, and is closed for the month of December. And so are 2 of my backup jobs (substitute teaching). Therefore, I will be packing boxes at Amazon to pay the rent.
        All I want in life is to love my work (and now I know what that work should be), and get a salary for it, so I can relax when my college or university or public library goes on Christmas break, instead of panicking about how to pay the rent. I feel like these are reasonable expectations, and yet they seem impossible to achieve.

      • Bsquillo

        See, I like doing both sides of this- having a steady, predictable day job with benefits, but also cobbling together all sorts of performance or other hustles on the side :) Best of both worlds for someone who is generally risk-adverse but also has a lot of creative energy!

    • NotMotherTheresa

      My husband comes from a similar family!
      At least in our case, another huge cost of entrepreneurship is the strain that it puts on family relationships. I come from a long line of “wage slaves” and one of the nice things about that is that it generally keeps family and work pretty separate. What my sister does over at Merrill Lynch has no bearing on whether I’ll be able to afford my mortgage this month. When the entire family is made up of business owners (particularly business owners in an insular area who all share the same last name), there is no dividing wall between your personal life, your work life, your second cousin’s personal life, and his work life. They all become intertwined, and it tends to turn into one big, murky, resentment filled soup of awfulness. Everyone gets along pretty well, all things considered, but it’s definitely created some deep seated resentments between relatives that wouldn’t be there if everyone worked salaried positions where their livelihoods weren’t affected by what Bob said that Tim said about John yesterday!

      • sofar

        OMG you totally get it. That’s so true.

        Because it’s family, there are NO professional boundaries. I can’t count how many times I’ve been eating dinner with my husband and his brother texts him that there’s an “emergency,” and it’s really just business stuff. And how many times a machine breaks, and my husband has his uncle come fix it and now he owes uncle a favor (which will inevitably be called in at 2am some random wednesday). Yes, some bosses in salaried jobs also don’t have boundaries. But I feel that kind of behavior is rarer in the salaried realm. Plus, you can quit your job with the crazy boss. You can’t escape your family that easily.

        • NotMotherTheresa

          Yessssss!!!! That is all entirely too familiar!!!
          Plus, I don’t know about everyone in our boat, but at least with us, it always feels like money is very emotionally complicated. If you work for DuPont, and your cousin works for Ford, and your cousin gets a bigger bonus than you do, you might be a tad envious for a second, but you aren’t going to get mad at the cousin, because their bonus is coming from an entirely different pool of money than your bonus. On the other hand, when you all own businesses that are partially intertwined, it means that even if it’s contractually clear who the money belongs to, it doesn’t always feel emotionally clear.
          I cannot count the number of times one person has bought a new house or truck with money from their business, only to have everyone else grumbling behind their back “That’s supposed to be MY Tahoe. MY family is the one who built up that arm of the business.”
          I realllly dread the fights that are going to ensue when the older generation (AKA the generation that built everything up and owns most of the assets) dies off, because I can already tell from the simmering resentments that it’s going to be WWIII. I mean, my husband and his cousin get pissy if one of them buys a new sofa when the other’s bank account is low…I can’t see the division of major assets going smoothly!

          (I mean, I suppose lots of rich families have a similar set of problems, but that’s the thing–none of the businesses are making anyone super rich. We have the same financial problems as any middle class office worker, we just ALSO have complicated estate and asset issues!)

          • sofar

            Real. So real. *solidarity fist bump*

    • AP

      Ugh, I totally hate that condescension toward 9-5 jobs that’s so prevalent in the personal finance/ financial independence blogosphere. My husband listens to a podcast on real estate investing where they refer to jobs as “J-O-Bs” and talk about “wage slaves.” I got pissed and told my husband if he ever refers to himself (with his upper middle class white, privileged, male ass) as a slave, I will kill him.

      • Lisa

        Really? Maybe it’s just the FI bloggers I’ve been reading, but all of them talk about how they used their steady employment as a way to achieve their goals of retiring early or having more say in what type of jobs they took. It’s actually made me feel more empowered to look at my job as a means to an end–instead of constantly upgrading our lifestyle in ways that I don’t feel we need, I can accept my employment as a temporary circumstance until I have enough money put away to leave the 9-5 cycle. (If I want to! Or I’m free to only take jobs that actually interest me!)

        • AP

          Oh, I am totally on board with achieving financial independence. It’s one of our family goals, for sure, especially getting to the point where we can work when we want to on work that we love. It’s just the condescension I don’t like, which you’re right, isn’t the tone everywhere. There are a few my husband listens to that are more strident than others and talk about people who have 9-5 jobs as sheep and mindless consumers. (Radical Personal Finance is one that comes to mind, and Smart Passive Income sometimes.) One of my struggles as we set financial independence as a goal is to grapple with the privilege that is inherent in that decision. So I’m maybe a little sensitive when I hear casual use of the word “slave” to refer to someone in a white collar desk job.

          • Lisa

            That’s perfectly fair, and I’m totally with you on the word “slave.” Besides the obvious connotations, it’s incredibly judgmental towards people who aren’t setting that goal for themselves. I think FI is going to eventually make me very happy, but it isn’t for everyone.

            I’m relatively new to the idea of FI, and I’ve been scouring Frugalwoods, Mr. Money Mustache, and JL Collins for information over the past couple of months. I’ve read some of Making Sense of Cents’s older posts, but I’m not in love with the newer ones, which mostly read like advertisements. I’m trying to get my husband on board with the idea of FI; his chief concern right now is finding a job after he graduates, but I’m already talking about what I want to do with that future income.

            Did you read The Simple Path to Wealth? I liked it a lot! I’m super tempted to get it for my sisters, particularly the youngest one who’s just starting her career and literally said she doesn’t know what to do with all of her money (what a problem to have!), but I worried it would come across as preachy.

          • AP

            Yes, LOVE Simple Path! We found JL Collins through a Youtube channel we like called Mike and Lauren. They are a 20something couple who started investing in their teens (!) and are now financially independent and traveling around in an RV. Show them Mike and Lauren! They talk about the power of compounding interest and living within your means in a way that is relatable and not preachy at all.

          • Lisa

            Uggggh, I wish someone had told me about investing when I was younger! My parents set up a money market for me as a baby, and I’ve been dumping all of my savings into it since I can remember. (I would even save up my allowances.) If I had been putting that money into investment accounts, I can only imagine what I would have by now instead!

            I’m going to have to check out the YouTube channel. I’m sure my afternoon’s productivity just went out the window…

          • Lisa

            I tried to convince my husband of the RV idea, but he is reeeeeeally not sold on it. Apparently I married the biggest homebody ever, which has me all kinds of upset.

          • AP

            Oh lord, I don’t know what’s worse, your homebody or my husband who wants us to live on a sailboat.

          • Lisa

            MY HUSBAND SAID THE SAME THING. He’s not interested in the RV, but he said he could see himself living on a sailboat. I had to remind him that I have horrible motion sickness, and daily life with me would be hell if we lived on the water.

  • Kate

    Okay, but the real question is how do I work for APW?

    • scw

      seriously!

  • Her Lindsayship

    I think this ties in with the “do what you love” advice – you just can’t apply a single philosophy about work to every individual. For one thing, it assumes that different personalities all have the same approach to work and work-life balance; and for another, it completely ignores the reality of different levels of privilege. Sure, anyone *could* start a business with no capital and no backing, no idea if they’ll actually make any money in the next year. But choosing stability over being your own boss or ‘doing what you love’ shouldn’t be considered a cop-out. We all have different needs, and it’s just not helpful to value one kind of work over others. It feels judgy.

    • La’Marisa-Andrea

      Yes. Also the doing what you love philosophy bugs me because even when you’re doing what you love, it is still WORK, it is still labor. Bills still have to get paid, etc. A business is still a business.

  • Kaitlyn

    This was very interesting, but I’m stuck on the EIGHT HUNDRED GUEST wedding. Who in the world did they invite?!

    • Lisa

      Entire church community or a very large family. I’ve heard of some Indian weddings with 500+ guests, and one of the Duggar daughters* had 1000+ people at her wedding because they invited the whole church to attend the ceremony and ice cream social afterwards. It’s certainly possible!

      *I’m shamefully admitting one of my intermittent guilty pleasures and posting the caveat that I stopped watching immediately after the allegations against the eldest son came out.

      • Danielle

        #noshame

    • stephanie

      The groom’s family is from India and also Hindu, and I believe large weddings are more the norm. It was a really incredible experience!

  • NolaJael

    This is the kind of tangential career advice I wish we talked about more with young people. We focus almost exclusively on subject matter and earning potential, to the detriment of a lot of other things that make people love or hate their jobs: working with teams vs. alone, indoors vs. outdoors, sales vs. non-commission, flexible hours vs. fixed hours, and so much more.

    • Lisa

      It’s taken me years to figure this out, and it was something I told my littlest sister to strongly consider when she was looking at jobs after graduating college this summer. I’m hopeful she’ll make fewer mistakes than I did because she’s already strongly evaluating her priorities and figuring out what type of work environment makes her happiest.

    • NolaJael

      And I hate that flexible work schedules are only discussed in the context of family planning. I have no kids but I hate having to use my precious vacation time to go to the dentist or take my cat to the vet. Lots of people would benefit from flexible schedules, not just societally designated caregivers.

      • Yes! One of the things I share with people about flex scheduling is that I don’t care if you take a 3 hour lunch, if your work is done well and reasonably on time. That’s my actual example, not even a “necessity” except that sometimes the soul needs a 3-hour lunch.

    • Sarah E

      Yup, 100%. I was intensely interested in the field I studied in college. But working in that field likely meant long hours in office settings, or emotionally draining, underpaid field work. No, thank you. Figuring out HOW I want to work has been way more important to me than WHAT I want to do.

      • stephanie

        I love this discussion! I absolutely hope that my experience will help my son down the road.

    • Kara

      YES! That’s one reason I wish high school students and especially college students would take the Myers Briggs test. It helps people understand certain aspects about their personalities and can help them make career decisions.

      A free and simplified Myers Briggs test is available through https://www.16personalities.com/ . It’s free, super easy, and very informative.

      • INFPer

        Perhaps…but “type” isn’t the sole driver of job preference – especially if you’re making that a single decision point in late adolescence. Can it be insightful? Sure – as can a lot of other tests and experiences and job contexts. I’m an INFPer THRIVING in an ESTJ world – working in “INFP” type fields would be…annoying and too draining for me.

        • Kara

          True, but it may provide perspective. Like I said I’m an ISTJ, I work in an environment that encourages innovation and adapting quickly, but someone has to make sure deadlines are met and things are correct / quality products.

          There are aspects of your personality that are useful to understand. For instance, if I was put in a Sales / Marketing role, I would up and quit. I just can’t handle that much interaction.

      • mssolo

        It’s worth pointing out that the Myers-Briggs is founded on some long debunked science. It think it’s really useful in giving people language tools to describe themselves, but what it’s really measuring is your mood on the day you take the test. If you have pretty stable moods, then you’ll get similar results each time, but for a lot of people it varies wildly, especially if you take it repeatedly over a number of years. I have the same personality I had as a teenager, but entirely different MB results, and people I share MB results with have wildly different personality types from me. The only thing that makes it more accurate than horoscopes is that it’s got more categories!

  • Leah

    Having watched others fail at the “working for themselves” thing and knowing it would not suit me in the least definitely makes me respect folk like Meg all the more. I wouldn’t be able to handle the pressure of working for myself, let alone being responsible for a bunch of other people’s salary. I’m glad there are folks suited to that hard stuff, and admire them all the more for knowing how ill-suited many of us would be for it.

    • stephanie

      Meg is pretty impressive! As someone who has run a business well and is voluntarily leaving it to work for her… I can definitely attest to this. :)

      • LP

        My Hindu coworker’s 400 person wedding was considered tiny. He said it’d be the equivalent to a 30-40 person American wedding. They have a very strong sense of community.

  • archivist777

    When your enjoyment of the work is equal (between the pre and post employed jobs) and the only difference is whether you are the owner or employed, I can definitely see why being employed could take a lot of stress off your shoulders. Especially with the scenario in this article, where being employed probably means working from home with flexible hours and not even putting in a full 40 hours a week yet.

    But in my experience, the vast majority of employed workers have to commute to an office and work at least 40 hours a week, doing something that isn’t necessarily a passion of theirs. In the last decade, I’ve had 4 different employers, and really enjoyed only one of those jobs. I’ve only ever been able to take 3 to 4 weeks of vacation a year, and that no longer feels like enough. I’m burned out, bored, and don’t feel valued anymore. I know there are other positions out there that could be better, but it’s not always easy to find them, let alone get them and receive the salary you want. Working for myself sounds like a wonderful and needed change at the moment. My husband and I are planning to start some online side-hustles soon, because we both need hope that the future can be different from the never-ending 8 to 5.

    • NolaJael

      “I’ve only ever been able to take 3 to 4 weeks of vacation a year, and that no longer feels like enough. I’m burned out, bored, and don’t feel valued anymore.” THIS.

    • Sarah E

      Yeah, I think part of the “dream” of self-employment is being able to loose the holds of capitalist-driven work standards. However, there are plenty of self-employed people who are yoked to it just as much as any employee might be.

      • NolaJael

        Agreed. I’ve definitely seen that the idea that you’re never finished/enough/done haunt a lot of self-employed people.

        • archivist777

          That definitely worries me about having my own business. But compared to the dismal state of my work satisfaction now, I would be more willing to deal with that, 100%.

      • Kate

        Definitely! For lots of self-employed people, the idea of taking a break is scary, and you never get a chance to switch off. Everyone’s different, but I remember always feeling like I couldn’t relax, just in case.

      • gonzalesbeach

        My partner runs his own business. He’s had one week of proper turn-the-email-and-phone-off vacation in 4 years. And yes, one week he might work 25 hours but the next is 60+ and a lot of the time, those hours are all over the place. Most are in the 60’s really. But he wouldn’t want to trade it for working for someone else. It’s just as demanding, if not more than working for a company. Actually scratch that. It is more demanding.

    • NotMotherTheresa

      Most people owning their own business are also doing something they’re less than passionate about…for every one hip boutique and cozy coffee shop, there are a bunch of accounting firms and house cleaning businesses.
      Best of luck with the side hustles. What you’ll likely learn is that not every personality is equally well suited to entrepreneurship–if you’re super independent and a natural salesperson, you may love it. If you aren’t, that’s okay, too, but it probably means you’ll quickly see the upsides to a 9-5!
      My husband and I both started our own businesses (construction and a law firm, respectively). His construction company is doing well, and most days he’s pretty happy with his decision. On the other hand, I was absolutely miserable–I hated having to market myself, I hated not having anybody down the hall who I could go to with questions, I hated the lack of predictability, I hated the way that I was never truly off the clock, etc.
      I think if I would have been more honest with myself about my personality, I would have seen the issues going into it. However, as a society we really push a lot of the values that make a good business owner, and that made it hard for me to admit to myself that I’m NOT some super confident maverick who was born to blaze my own trail.

    • mssolo

      I think stronger labour laws make a big difference. I suspect in countries with a maximum length of working week and a minimum paid leave allowance you probably see more job satisfaction in employees. Though, living in a country with at least some of that, what we seem to be getting more of is false self-employment as a way of getting around those laws. If you’re a delivery company it’s easier to claim all of your drivers are self-employed contractors, and work them 60 hours a week with no holidays, than it is to pay them salaries.

  • Jessica

    I’m the only employee at my 115 year old non profit, and last year I had to seriously look at applying for new jobs because of some bad budget decisions the previous Treasurer made. It made me realize that I love setting my own hours, having tons of responsibility, and being able to be independent about projects and goals. But I also get to say “no” to things that would put me over my allotted hours per week, which is a source of freedom I do not want to give up.

  • La’Marisa-Andrea

    I have my own firm and man is it hard. It is also a very lonely place and I often want to throw in the towel. I don’t find employment anymore stable than self employment. That’s really a matter of perspective to me. I enjoy self employment for many reasons and even in economic downturns I can plan for it whereas with employment you never know if you will be laid off etc. I have a lot of freedom to say no in theory but the reality is, I’m running a business and we have to make money so the NO isn’t exercised very often. I don’t prefer self employment to being employed. They’re both different and I have loved and hated both.

  • Kate

    Yes! There are so many articles about how amazing it is to work for yourself (and it can be) and so little from people who decide to stop being self-employed. It’s as if it’s viewed as a failure. I got to a point in my own business where I didn’t want to expand anymore, and there was someone I trusted who did, so a sale seemed like a good idea. 6 months later, I LOVE working for other people. The stress and anxiety I’ve been carrying for the last few years has melted away. Sure, there are times when I’d love to do my own thing, but right now, this is perfect.

  • lindsay

    yes yes yes – thank you for everything in this article. My parents owned their own business and while it was nice for them to be able to take 2 week vacations without clearing it with anyone first, they carried the weight of knowing they needed to make shit happen to pay themselves (and pay others). The good years were good, and in the shitty years, my mom went without a paycheck for months so they could make payroll for others. And when their business, their baby that they built for 20 years, closed and went bankrupt, it was a huge impact on their finances, but also their identity. What did it mean for them as people if their business wasn’t successful? Would other people see them as failures in the way that they felt inside? When articles talk about starting your own business, they very rarely talk about the mindfuck that can come with it.

    My parent’s experience in entrepreneurship and self-employment made me never want to own my own business. I’m perfectly happy working 40 hours for someone else (in a position where I’m valued and can contribute my talents) and expressing my entrepreneurial side in a side hustle.

  • ART

    My husband owns a pretty new business (just him, plus me, no actual employees yet) and it is fascinating and inspiring, but also terrifying and stressful. I work at a 500-ish-person firm that is 100% employee owned (we have an employee stock ownership program that all employees are automatically enrolled in after a certain amount of time, then vested bit by bit over several years). It is how our profits are distributed (back to us). I really love this model – I work both for “someone else” (the company) and for myself (as a part owner). I don’t think I would choose to go to a privately held or publicly traded firm. I may end up in government or some institutional setting (like a school) down the road, but there’s something both entrepreneurial and super safe about the way my firm is set up (and the way I get paid every 2 weeks and have insurance and benefits!)

    • Danielle

      That sounds like a wonderful model! I wish more workplaces were worker-owned.

  • emilyg25

    I love this! The idea of being my own boss kinda makes me want to hurl. I got no hustle. I highly enjoy job security, set hours, being part of a team, leaving my house and getting benefits. I don’t really know why people make such a big deal out of entrepreneurship, tbh.

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  • mssolo

    I so much prefer working for someone else. My mum was self-employed and worked from home, and it just put me right off it! Clients expected her to be available 24/7, they resented the fact she needed time to do all the other things you have to do when you work that aren’t work (like taxes!), and they thought they could get away with underpaying her. Me, I like a really strong divide between work and home, to have other people in charge of making sure my taxes are right and my pension is paid up, and to know how much money I’ll have at the end of every month. Work life balance ftw!