One year later: The benefits and tragedies of self-employment

Almost exactly a year ago today, I quit my full-time job to pursue my passion — writing. It was one of the proudest moments of my life, but it was also terrifying. I had spent the last six years working alongside my husband, a mortician, in the funeral industry. My job certainly wasn’t perfect; but it was stable, well-paying, and sometimes fun. I also loved the people that I worked with and was extremely attached to a few. On the other hand, I knew it was time. I had been working full time and writing on the side for so long that I no longer knew what a “real life” was like. In fact, my “real life” was a mess.

Everyone talks about how lucrative and exciting having a “side hustle” can be, but no one talks about the toll it can take on your life. Since I worked 9 to 5 and had two small children, the only time I could write was at 5 a.m. before work or at 8 p.m. after the kids went to bed. This meant that I was working 16 hours a day at times — actually all the time. And the weekends? I worked those too.

But, like I said, one year ago today was the day I finally snapped. It was a Saturday afternoon and I had worked over 70 hours that week, yet I was stuck working late at my job … again. I called my bosses and asked if I could talk to them. And when I showed up at their home, I nervously put in my three weeks’ notice and hoped they would forgive me. Then I called my husband.

“I did it,” I said. “I quit my job.”

We had been talking about it for months. I always said that I would quit when my side income surpassed what I earned at my full-time job. But saying it and actually doing it were two entirely different things. Ironically, leaving my mortuary job felt like a death in itself. I knew that once I left, there was no going back.

“Awesome, Babe,” he said. “You’re self-employed now. It’s all you.”

The Benefits of Self-Employment

Once my final three weeks were up, I hit the ground running and started looking for writing jobs to fill my 40- hour work week. And it didn’t take long. Soon I was working 40 hours per week, or more just to keep up with the various writing jobs I had acquired and my own two websites. But the work wasn’t draining me the way my old job used to. In fact, I felt like I had a whole new lease on life — like I had rediscovered myself. The fatigue and exhaustion I felt when I quit my job had been replaced with inspiration, creativity, and passion. Some of the other benefits I noticed right away:

  • Flexible schedule — I quickly found that one of the best parts of self-employment was the ability to create my own schedule. And since I was no longer tied down to 9 to 5, I began working 7 to 3, which is my ideal.
  • Less time primping — I absolutely hated doing full makeup and hair every weekday, so abandoning that ritual was fine by me. Doing so also freed up at least 45 minutes of my day, which allowed me to start work earlier.
  • Normal lunch routine — My old job made lunch time nearly impossible some days, either because a funeral was going on or the phone was ringing off the hook. But now that I was working at home, I could make a healthy meal and eat it without interruption.
  • Less stress — I was constantly teetering on the edge of insanity at my old job, usually because there was so much going on. It was stressful. Once I started working from home, the stress instantly melted away. I no longer had to juggle 500 things at a time and make small talk incessantly. I only had to focus on work.

The Tragedies of Self-Employment

Self-employment seemed like the perfect gig at the beginning; but as with most things, the disadvantages of my new arrangement began to show once the newness wore off. First things first, I never realized just how high taxes are for self-employed individuals. Basically, because the self-employed work for themselves, they have to pay twice the amount of Social Security and medical taxes. It’s understandable, but it doesn’t make it any easier to write the check.

And about those checks. I hated paying quarterly taxes at the beginning. When I worked in my 9-to-5 job, I just had extra money taken out via payroll to account for the extra taxes I would owe. But now I had to part with my money the old-fashioned way, and it was painful. For some reason, it’s an entirely different feeling when the money is quietly deducted from my paycheck compared to actually having to pay taxes as if they were a bill. I wrote about how paying cash hurts a few months ago, and it’s true!

No Employer, No Benefits

Another big issue we’ve encountered is a lack of options when it comes to health insurance. Since my husband works for a small employer who doesn’t offer coverage, we’re basically on our own. We hoped that the passage of the Patient Protection and Affordable Care Act (PPACA) would help us, but found that we make too much money to benefit at all. In fact, the cheapest health insurance plan available to us is almost twice what we pay now (we currently pay $393 per month), and it carries a $12,000 family deductible.

Our current plan expires later this year, and we’ll have to decide if we want to pay nearly $800 per month for a plan we’ll likely never use or try something unconventional. And when I say “unconventional,” I mean that we’ve considered joining a healthcare sharing ministry, something that Get Rich Slowly writer Lisa Aberle wrote about last year. But for now, our healthcare situation is up in the air.

In addition to those gripes, here are some other disadvantages I’ve noticed since becoming self-employed:

  • No 401(k) match — My previous employer generously matched the first 4 percent we contributed to our company-sponsored 401(k) plans, and I really miss it. Now I have to save more to reach the same retirement savings goals I had when I worked for someone else.
  • No social interaction — I really miss having co-workers to talk to and spend time with, and spending all my time home alone can get boring. This past winter was particularly rough since it was so cold and miserable outside. I felt completely isolated from the outside world at times.
  • Work becomes “work” — Even if you start doing something out of passion, it seems like almost anything becomes “work” at a certain point. I still enjoy writing, but it’s different now that it’s my full-time job.
  • No paid vacation — I got 20 days of PTO at my old job, all of which I forfeited when I left. Now I get zero paid vacation days, which means that I typically work on vacation. I miss having that carefree time off, and the paycheck that came with it, of course!

The truth is, no job is perfect. I certainly lost some perks when I quit my job, but I gained some awesome benefits too. I suppose it’s all about balance and finding a situation that is as close to ideal as possible. I miss my old job and my old identity, but I’m loving my new-found freedom and the responsibility that comes with it. Now I can only hope that, when all is said and done, I made the right decision. Because, like I said, there’s no going back now.

Have you ever considered self-employment? Do you think you would like it? What is your ideal working situation?

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There are 79 comments to "One year later: The benefits and tragedies of self-employment".

  1. Tina in NJ says 07 May 2014 at 04:28

    As a stay at home mom, I identify with your missing social interaction. I volunteered at my kid’s elementary school and talked to other parents at pick up, but the youngest is in middle school now. I don’t pick up or drop off any more as we only live a few blocks from school. I’ve been talking about a part time job for a while, but fear of change and rejection have held me back. Maybe next fall…

    • Basit Shah says 15 June 2015 at 01:37

      See, being an entrepreneur and doing your own business is something that can be challenging, but it has a lot of perks, however, if you do not move now you might not be able to move next year either. I saw the word “fear” in your comment, if you want to get into self employment or become a business person, you will need to get rid of that fear and failures, you gotta try to see how things go, only things you need are desire and pure perseverance. Good luck.

  2. Beth says 07 May 2014 at 05:01

    Gut reaction: tragedies? Seriously? No one is sick. No one died. You made a choice and you’re still in control of your life.

    Second reaction: I think this post does a good job of pointing out the advantages and disadvantages of self employment. Usually PF blogs praise how great it is to be self-employed, so it’s nice to see some balance. Often times self-employment is also a career change rather than a change in employment status.

    There are many reasons I like working for someone else at this point in my career — especially the social/team work aspect and the opportunities for professional development. I would also have to put off buying a home even longer because you need to show two years of steady income if you’re self employed. Ugh.

    • Jane says 07 May 2014 at 06:21

      Ha! I was going to come on here to say the same thing. Tragedy is such a strong and inappropriate word to describe what you mean. As a writer, you should know that hyperbole undermines your argument. I would change “tragedies” to “pitfalls” ASAP, because it taints an otherwise interesting article.

      • Jenny says 07 May 2014 at 07:43

        In Holly’s recent post on “How to Track Your Spending”, she described her friend’s decision not to track spending despite living beyond his means as “tragic”. One would think that a person who spent years working in the funeral industry would have a better understanding of what that word means.

        • Holly@ClubThrifty says 07 May 2014 at 07:47

          There are usually at least a few people who hate one thing I say, or pick apart a sentence they don’t like. I’m used to it.

          As far as using the word “tragedy” goes, it’s just an exaggeration. It’s also just a word, and it has little to do with the 1000+ word post I wrote.

        • Jane says 07 May 2014 at 08:01

          Holly, since when does word choice in writing not matter? It matters a great deal! Plus you can never argue that a word you use in your title in inconsequential. J.D. learned this last week in his post about “rules” for higher earning wives.

          Now that Jenny brings it up, I remember the inappropriate use of the term tragedy in your other recent post. I am rather surprised that you would use the same word again and this time in an even more out-of-touch manner. I guess you can continue to use the word incorrectly and we can continue to point it out to you.

        • Holly@ClubThrifty says 07 May 2014 at 08:17


          I think it is tragic that you are spending your precious time obsessing over my hyperbolic use of the word “tragedy”.

        • Jane says 07 May 2014 at 08:33

          Trust me, Holly, as a 40 week pregnant women waiting for labor to start, I am acutely aware of your snarky point.

          Regardless, your inability to graciously respond to criticism has been duly noted by me and many others reading this thread.

        • KT says 07 May 2014 at 09:15

          One would think someone who depends on freelance income would be bit a more diplomatic in responding to criticism.

        • Beth says 07 May 2014 at 16:05

          “Be kind, for everyone you meet is fighting a hard battle.” –Plato (Okay, I don’t know if Plato ever said that, but the sentiment is good nonetheless.)

          I don’t think Holly set out to offend anyone, but at the same time online writers should be ware that they never really know what their audiences are going through. IMHO, if you wouldn’t call your lack of a 401K match a tragedy when talking to someone dealing with a far more serious issue, then maybe it’s not the right thing to do in a blog either.

          I’ve worked in customer service long enough to know that yes, you can’t please everyone all of the time and the customer isn’t always right. But sometimes they are, and sometimes it’s worth listening. I don’t think any business is above learning from their customers.

        • Holly@ClubThrifty says 07 May 2014 at 16:12

          “I don’t think Holly set out to offend anyone, but at the same time online writers should be ware that they never really know what their audiences are going through. IMHO, if you wouldn’t call your lack of a 401K match a tragedy when talking to someone dealing with a far more serious issue, then maybe it’s not the right thing to do in a blog either.”

          Beth, I get what you’re saying but I have no desire to write in a way that couldn’t possibly offend anyone. If I wrote that way, I would just be a watered-down version of myself and it wouldn’t be authentic. I refuse to do that.

          I would rather write what I want, knowing that people won’t always like it. I can live with occasional criticism.

          My audience is basically anyone on the internet. If I spent time dissecting each of my posts to find anything that might offend someone on Earth, that would be a full-time job. Anything you talk about touches a nerve on someone, somewhere.

        • Beth says 07 May 2014 at 17:58

          @Holly — I don’t think it’s possible to write without upsetting someone. In fact, making people think is part of the job of a writer, no? Criticism goes with any creative job… One of my other favourite quotes is “”If no one ever criticizes what you do, you aren’t doing anything worth noticing.”

          I liked your comment about authenticity — I think many of us can relate to that because we read blogs for the personality as much as the information. If you’d responded with that comment upfront, I think you’d find people nodding their head in agreement rather than feeling dismissed.

          I can see both points of view. Language is fluid, but I think we learn a lot in the disagreements over its meaning 🙂

        • Elle says 09 May 2014 at 09:30

          Wow, you guys are pretty mean-spirited. Is it bust on Holly-Day and I missed the memo? YIKES.

      • phoenix1920 says 07 May 2014 at 08:30

        @ Jane:
        ” I guess you can continue to use the word incorrectly and we can continue to point it out to you.”

        While I understand that you feel one word choice was disagreeable, since “tragedy” actually has multiple meanings (as most words do) and also means a “very upsetting situation,” I struggle to see how the use of this word is “incorrect” unless you are suggesting that a person cannot feel very upset by having to write a check to the gvt for thousands of dollars.

        My dh used to run a side business where we had to pay quarterly taxes, and I remember distinctly that first time when we realized the amount of our tax bill–it was a horrible stomach-falling-to-the-ground feeling that came as a complete shock and was very upsetting to me.

        • Jay says 09 May 2014 at 17:00

          I agree 1000% with Holly. For people to pick apart a single word in a 1000+ word article is silly. You have too much time on your hands if that’s all you are able to find fault with in this article.

          And dare I say please get over yourself.

        • Beth says 10 May 2014 at 04:11

          @Jay — Thank you. Your comment has woken me up to the fact that PF blogs have become a time suck for me. (Not just this post.) I enjoy the discussions here, but I’m not really learning anything new anymore. I think I should focus on learning about investing instead.

          I’m not being sarcastic or snarky, and that isn’t a critique of any of the writers here. I would happily recommend GRS and other blogs to people who are at a different stage in their PF journey. Best wishes, everyone!

    • Holly@ClubThrifty says 07 May 2014 at 07:39

      The part about buying a home is so true. We bought a new home early this year, and they wouldn’t even consider my income for our extremely small mortgage. Fortunately, my husband’s income was enough. Otherwise, I’m not sure what we would have done.

      • Diane C says 07 May 2014 at 10:30

        Yeah, I’m going to take a swing at this one.

        Grammar Police/Snark Alert:

        So, tragedy was averted in this case? So happy for you, Holly.

        • Holly@ClubThrifty says 08 May 2014 at 06:59

          Thanks Diane!

      • Beth says 07 May 2014 at 14:59

        I would say rent but they look at your income for that too! (At least where I live.) Glad it worked out for you though!

        Sometimes full time self-employment has a way of finding people at the right time in their lives 🙂

    • Reggie says 07 May 2014 at 15:00

      This is the kind of article I was hoping for last week when I commented that William’s article was glorifying self-employment. This was a great balanced view of the realistic pros/cons of self-employment from someone who is actually doing it, not someone who is THINKING about doing it.

      One point mentioned in the article, but not emphasized, is the fact that she didn’t quit her day job until the income from her side gig was equal to her day job. This required working 70+ hours per week for an unstated amount of time. I think this is a highly realistic scenario that is also not usually shared when people are pushing self-employment.

      Net, self-employment is a career choice with pros and cons, NOT some utopian dream for everyone to strive for.

      • Beth says 07 May 2014 at 15:07


        Self employment doesn’t have to mean working from home either. I’ve worked for amazing small businesses, and know people who have started a roofing or masonry business, for example. So many options — but I think Holly articulates well the challenges of work/life and financial balance.

  3. Jon @ Money Smart Guides says 07 May 2014 at 05:33

    I share many of the same feelings as you do about self-employment. For starters, it is different having to write a check for estimated taxes vs having the money just taken from your paycheck without really noticing.

    The days alone can be an issue as well. I’m more of recluse, so I like being be myself, but there are times when I am about to snap. I’ve started going to the gym in the late morning to get my social interaction fix. I come home, make my lunch and eat while checking up on emails/commenting. It has helped me a good bit.

    Overall, I love the freedom working for yourself brings. I hated the fact that while at a job, I had to be there for 40 hours a week, even if I got all of my work done. By working for myself, if I finish up things at 2pm, I can do whatever I want. Additionally, there are some mornings I wake up and don’t feel like working. So I’ll do stuff around the house and work later in the day or at night when I have the motivation to do so.

  4. Meena K. says 07 May 2014 at 05:37

    I’m actively working towards self employment right now. Hopefully I’ll quit the corporate world within 3 years. Isolation is the biggest difficulty I see so I make sure to attend group seminars and events. As well, interacting with people is part of my business plan.

    • JoDi says 07 May 2014 at 08:27

      Isolation may be the biggest problem you foresee right now, but the cost of health insurance is the biggest problem you’ll actually face if you’re currently insured under your employer’s plan.

  5. Kristin says 07 May 2014 at 05:42

    I became a self-employed professional last year after 14 years working in the industry for other people. I must say, I vastly prefer working for myself at this point in my career. The flexibility is important at this point, since my husband is a full time student with a very inflexible schedule. I can take care of all of the kid stuff, and can work at home if I want. Unfortunately, I was not able to take any clients with me from my last position, so I had to start from scratch. It’s taken a year for me to turn a consistent profit that will support my family. However, I have the potential for a lot more income than if I worked for someone else. Taxes are painful, but not nearly as bad if you just pay your quarterlies instead of ignoring them. For my situation, I think the advantages of working for myself outweigh the disadvantages.

  6. Stefanie @ The Broke and Beautiful Life says 07 May 2014 at 05:52

    I’ve always dreamed of self employment, but the lack of benefits is quite frankly, scary. Though I guess it’s no scarier than the constant un and underemployment I face as an actor. I just can’t imagine what it would be like to have children depending on me. Guess that’s my motivation- build up my freelance work enough to have babies! 😉

  7. El Nerdo says 07 May 2014 at 05:58

    Paid vacation, benefits, payroll taxes, etc– these are calculated by your employer as part of your salary, so while your check says you get X pay, the employer sees you getting X+n. When you negotiate your salary, you may be thinking of your take-home pay, but they are thinking of that plus everything else that goes into keeping you there. So while it looks like you’re now “paying more”, you’re really paying the same– this is just now apparent to you, where before it was just hidden.

    The problem, seems to me, is that you’re getting paid much less now, which is why the payroll taxes hurt. But hold up a sec. Look at your per-hour rate. You got paid salary plus half of your payroll taxes plus benefits for 70+hour work-weeks. That’s nearly 2 jobs. Then look at how much you’re making per hour now. That’s the real comparison. You could always decide to work 70+hours per week if that’s what you really want, but you aren’t forced to do it.

    As for the lack of social interaction… I see that as a huge boon, haaa haaa haaa (but if that’s not what you want, there are options.)

    • Natasha says 07 May 2014 at 06:11

      I have always loved your posts, El Nerdo. Your approach to personal finance, and “growing your own pumpkin” has been inspirational.

      I agree, looking at how much time you are reclaiming does help you perspective. Now you have more opportunities to write, maybe create an e-book (passive income), and consult. Your earning potential is much greater.

    • Holly@ClubThrifty says 07 May 2014 at 06:26

      Yes, I am aware that my benefits ate up part of my compensation at my old job. I was just sharing how much different it feels to actually write a check for my quarterly taxes vs. having them deducted from my paycheck. Even though I’m essentially paying the same taxes I was before, it still hurts slightly more! =)

      Also, I’m making at least twice what I earned at my full-time job now, so I’m not sure if the second part of your comment is directed at me or at someone else.

      • Brooklyn Money says 07 May 2014 at 09:48

        You are not paying the “same” taxes as before. You have to pickup the part of the social security tax that your employer would have previously paid. Although of course as as freelancer you can have business deductions that would be hard to claim with a full time job.

      • El Nerdo says 07 May 2014 at 10:45

        @ Holly – Yes, I thought I was directing it at you, but now I realize there’s no tragedy (I thought payroll taxes were killing your bottom line). If you’re making double in a lot less time, even after taxes, that’s very good reason for a party (a thrifty one, of course). Then if you keep your expenses at the old level you can have the equivalent of a second salary to pay yourself all kinds of benefits and then some. I see no real downside to your self-employment story, but for people who miscalculate it could be a true tragedy.

        @ Brooklyn Money – yes it’s the same taxes. You realize that your employers would be able to pay employees much more direct cash if they didn’t have to cover payroll taxes and benefits, right? This is why as a contractor one can usually get bigger checks than as an employee (no social security, medicare, unemployment, workers comp, sick leave, vacation, paid holidays, health care, retirement, HR staff, etc. ). At the same time, contractor has to cover all that on their own. It’s like that old Carmax commercial where the guy squeezes a balloon in one place only to have it inflate in another place. Same money, just shifted around– tricks of perception and nothing more. This is something to take into account when negotiating contractor’s fees. Only problem is, some people will race to the bottom and end up broke.

        @ Natasha – thanks for the kind words!

        • Holly@ClubThrifty says 07 May 2014 at 11:57

          Thanks, El Nerdo!

          Yep, that’s totally the plan. We hope to keep our expenses as low as possible and haven’t added anything since we started earning more. Our situation will change as our kids get older, but I hope that the expenses will balance out over time. I want to “keep” my additional earnings and make them work for me, instead of using them as an excuse to increase our spending.

  8. Natasha says 07 May 2014 at 06:07

    I am only an occasional poster, but really love this forum! I am a single mother, with a full-time IT job, and a “side hustle”. I work from home 100%, and hope that this feedback helps.

    1. No 401K match – Try looking at the Solo K – It is WAY more flexible than the 401k (although I understand missing the matching funds).

    2. No social interaction – Definitely take out 2 lunch hours per week to reconnect with friends/ex-co workers. Doesn’t have to be expensive, but maybe take a sack lunch and eat with them? This gets you out of the house and increases social interaction. Also, join a meetup group of like minded people that you meet with 1-2 times per month.

    3. Work becomes “work” – Agreed.

    4. No paid vacation – Plan your own vacation time. That is the wonderful thing about self employment (depending on what type you do). Since you write full-time, maybe compile a bunch of potential posts ahead of time, and submit them to the webmaster, or site owner, then take some time off!

    5. Benefits – This is always tough. My premiums would have gone down if I had was not working full-time. The ACA has been beneficial to some, but not for all. I still hope that the US Medicare age is dropped to cover all citizens (or some type of catastrophic coverage), and that paid insurance can be purchased at a lower cost.

    Very, very proud of your accomplishments, gives me a lot of hope that i will be able to transition my life to full-time self-employment soon!

    • Holly@ClubThrifty says 07 May 2014 at 11:54

      Thanks for the thoughtful comment, Natasha!

      1. I actually have a SEP IRA at the moment. It allows me to save 25% of my net employment income each year (I maxed it out last year!). I use it in conjunction with my ROTH IRA.
      2. That is a great idea, although I don’t know anyone personally who does what I do for a living. I do belong to a few groups that meet on Skype/Google Hangout though, and it really does help to bounce ideas off of like-minded people.
      4. We go on lots of trips because I’m a travel writer first and foremost. I have to struggle not to check email or work, and I am only successful about half the time. I’m a workaholic at heart, so it can be a challenge!

      Good luck on your journey to self-employment!

  9. Sandra says 07 May 2014 at 06:09

    Nice article. I challenge one assumption though. You have two children and you believe you will not needto use health insurance? I hope that is the case, but it is highly likely not to be so. Get the healthpolicy and take advantage of all the well care that is provided with your premiums. Annualmcheckups, vaccinations (please don’t tell me you dont vaccinate, because then my belief in your judgement will fall preciptously). I am older than you and my children are grown. One accident can destroy all the planning you have done to become financially secure. And you will age, and yes, need health insurance. Stuff happens no matter how many healthy lunches you eat.

    • Holly@ClubThrifty says 07 May 2014 at 06:33

      Hi, Sandra!

      I never said that I didn’t need or wouldn’t purchase health insurance. I said that we would likely join a healthcare sharing ministry, as hundreds of thousands of people across the U.S. do every year.

      It’s similar to health insurance, in that the group collectively pays for each other’s medical bills once they hit a certain amount. Here is a link to one of the sharing ministries we are considering if you are interested in reading more:

      Also, we have always had a high-deductible health plan (and still do at the moment until it expires), so we have always had to pay for well visits out-of-pocket. I am more than happy to pay for our well visits out-of-pocket, as I always have. In fact, I just took our two kids to the doctor last month and paid for it out of our Health Savings Account. And yes, they got all of their shots. My daughter had to get her final shots so that she could start kindergarten this year =)

  10. Bob says 07 May 2014 at 06:20

    I feel your pain when it comes to health care being up in the air.

    I currently pay $244 a month for my wife and daughter on a 90/10 plan with a $250 deductible and out of pocket max of $2500…This is set to expire after the mid term elections (how convenient).

    I am like you and don’t qualify for any subsidies since my household income is above $35K per year.

    I will be forced into a plan that costs $500 per month with a 12K family deductible.

    There are a lot of people in the middle class who will feel the pain from this law.

  11. Brian@ Debt Discipline says 07 May 2014 at 06:21

    I believe there are pros and cons for either side. It really depends on your personal situation. I would not leave my job for self-employment, unless I could duplicate my income and cover healthcare cost. With changes in healthcare cost, it could become easier to cover this in the near future.

  12. Daniel Koffer says 07 May 2014 at 06:48

    As a self employed individual I can contribute far more to my 401k than an employee. I usually contribute 35-45k/year. That’s a huge advantage that isn’t mentioned in this article.

  13. Michelle at Making Sense of Cents says 07 May 2014 at 06:57

    There are definitely pros and cons to self-employment, but I could never go back to my old day job, or to work for someone else. I have only been fully self-employed since last October, but I have loved every single minute of it so far.

  14. SavvyFinancialLatina says 07 May 2014 at 07:05

    I think being self-employed is pretty cool. I haven’t been self-employed but dealing with the pressure of corporate is tough. But I rather have a corporate job than work in a family business. My husband works in his family business, and it’s tough in other ways. He doesn’t have to deal with politics, but he does have to thread carefully with family.

  15. Babs says 07 May 2014 at 07:38

    Employers also pay Workers Compensation Insurance for injuries incurred at the workplace. So be careful!

    The small business I work for has a great Independent insurance broker. You might look into that for your health insurance needs. His company shops for us among many different companies & plans. He does this for individuals too. There is no fee, I assume he gets commissions from the insurance companies, but we don’t get any pressure to buy more than we need or can afford. He has really built a nice business on good service.

    Also I would like to add that 70 hours a week is borderline criminal & I don’t even know how you could do that with a spouse & house & 2 small children. If you are making more money now then good for you!

    • Holly@ClubThrifty says 08 May 2014 at 07:07

      Good point about Worker’s Comp insurance, although I hope not to get hurt as a home-based writer. Ha!!!

      Anyway, I agree that 70+ hours of work is borderline criminal, but I did that to myself. I have a tendency to take things to extremes. Looking back, I’m not sure how I juggled everything. All I know is that my life sucked.

  16. Broke Millennial says 07 May 2014 at 07:57

    You pretty much nailed all my concerns about self-employment. I recently worked a few days from home while my bosses were out of town and I got so bored. I love the social interaction of an office. But, it would be nice to set my own schedule.

  17. Scooze says 07 May 2014 at 08:04

    Interesting article and good comments. I just want to add that I think you should reconsider working during your vacation. Vacations are valuable because they allow you to recharge your batteries and get some much-needed rest. You are cheating yourself of an opportunity to come back with a better mindset if you choose not to take a real vacation. Even if you just give yourself two weeks, its still important time.

  18. Lisa Aberle says 07 May 2014 at 08:08

    This is an appropriate post for me to read today, because as of today, I am completely self-employed for the first time since, well, since I got my first real job 18 years ago. My challenges will be figuring out how to maximize my income while working 25 hours/week or less, and figuring out a schedule. Thanks for the article!

    • Beth says 07 May 2014 at 15:13

      Congrats and best wishes!

  19. Brian @ Luke1428 says 07 May 2014 at 08:14

    I think you’ve outlined both sides of the argument well. There is no job absent of challenges and struggles. And I can see how the lack of socializing with others would be a big deal. Just don’t let that drive you crazy like Jack in The Shining. 🙂

  20. Don says 07 May 2014 at 08:28

    “Choose a job you love, and you will never have to work a day in your life.” – Confucius

    • Donna Freedman says 07 May 2014 at 15:36

      I respectfully disagree. Or at least I’d like to say that just because you love something that doesn’t mean it isn’t work.
      I love writing and I’ve been doing it full-time for 30 years, freelancing for the last 10. Some days I love it and some days I feel like flinging myself out a window. (Of course, since I live in a one-story house it would be a largely ceremonial gesture.)
      But EVERY day it feels like work. Sometimes I still can’t believe I’m being paid to do what I love, but it is definitely work.

  21. Alex @ Credit Card XPO says 07 May 2014 at 11:01

    Being self-employed definitely has its pros and cons, but I wouldn’t call some of the disadvantages “tragedies”. Hopefully one day you could hire writers to write for your websites so you could actually own a business not a job. =)

  22. mary w says 07 May 2014 at 11:05

    I urge you to continue your health care even when the cost rises. My DH ran a marathon in February and was going to hike the Inca Trail this fall. This morning, however, was spent getting a liver C-T to get more information about the masses in his liver.

    The reality of how healthy you and your family is can turn on a dime.

  23. Carla says 07 May 2014 at 11:07

    I have considered it and have done it one way or another. When I had my web store and blog I worked my 45 hour a week job and worked the business during the evenings and weekends. I never made enough to quit my job so I worked the two jobs until illness forced me to go on disability. Eventually I sold the business because I could not handle it at the time.

    When I first started this new job two years ago, I was on 1099 so I had no benefits. Though I am now w-2 I still don’t have paid time off or paid holidays. The benefit is that I work from home and its part-time because I can’t work full-time. Part-time jobs outside of a cafe or grocery store is pretty hard to come so I am pretty lucky.

    I am working on a new project which will add another an hour or two of work per day and I am worried about it but I won’t know unless I at least try.

  24. Dave Lalonde says 07 May 2014 at 11:58

    Not having 401k, health insurance, or PTO is brutal. But despite the cons that you may come across, I have to say, one of the greatest joys in being self employed is having the ability to see the seed you planted; grow.

  25. lmoot says 07 May 2014 at 12:18

    See, I don’t think I can be self-employed. I always love the option of running away for several months at a time which would probably be bad for business. Though I guess independent contractors can have the option of taking on less gigs.

    Hmm, seems like maybe the cons of self-employment should apply to self-employment that is intended to support the majority of one’s expenses. I’d like to “do my own thing” one day, but only if my profit needs don’t exceed a few thousand per year, and the time-commitment is less than the job I’m leaving behind.

    When you have large, unmoving expenses, or are counting on earning a higher amount from self-employment then yeah, it’s terrifying.

    • Carla says 07 May 2014 at 19:56

      When you run away from work you still need a job when you get back…

      • lmoot says 08 May 2014 at 15:41

        Yeah, but it’s a whole heckuva lot easier to get another job than to start another business. Especially if you use your extended time off to learn a new trade or industry to add to your list.

        • Carla says 08 May 2014 at 16:16

          That is true, especially if you did learn a new trade during your “time off”. In my experience there are not many things that employers hate more than someone whose been off work just because. You’d better be learning something!

  26. Bruce says 07 May 2014 at 14:16

    I have been self employed for nearly 30 years and will never work for another boss. I work when I want, and take the dog for a walk or take a nap when I want. Sometimes I work at 3 AM if I can’t sleep. Sometimes I take an entire day off. I save a ton of money and time not commuting to work.

    Please follow up with an article about the valuable deductions available to the self employed. Yes, health ins. is high, but for the SE, it can be deductible. Auto expenses, meals out, office supplies, computers, phones, phone bills, internet service-many of these items are either partially or fully deductible. Please consult with a good tax person or better yet, CPA. I have found that the deductions more than offset the additional FICA taxes of the SE. Good luck!

  27. Redstar says 07 May 2014 at 18:28

    I have been self-employed (completely) for almost 5 years. Yes I do agree that taxes are excruciatingly high (live in Hawaii) and so is our healthcare cost. Fortunately my husband’s HC premium is 90% paid for at work and we pay for mine which in Hawaii is $450-$500 a month. The benefits? I make much more working about 35-40 hours a week, I enjoy what I do, find plenty of interaction with my clients, and I control my time. We contribute to a ROTH and now own a home. Many sacrifices and part-time jobs and patience to hone my craft and establish ourselves before I left my last official “employer”…. My peace of mind and flexibility are priceless. And I usually work with great people… No career path is perfect. Look for the silver lining and you’ll find it.***

  28. realuser says 07 May 2014 at 21:02

    My mostly failed business lasted some years before putting me in debt I’ll be in for a decade.

    All I can ever do now is pay back some bank. I have my expenses down and a payment plan and all that jazz but I’ll be committed to ten years working 2 or maybe 3 jobs with before it’s over.

    Could be you.

    PS: 401k match? Paid vacation? You don’t get any of those things with self-employment. You work 80 hours a week and stay up nights scrabbling for clients and hoping that the darkness you’re staring at isn’t what’s left of your soul. The only people who write fluffy pieces about self-employment and how wonderful it is are people who have some spouse working a high paying job or have some other source of wealth to prop them up.

    • Erica says 08 May 2014 at 08:23

      My experience has been the opposite. I started my business as a single, female, 30-year-old homeowner without a dime from anyone! And I’ve been at it for six years, making more money than I did in corporate gigs.

      I think the lack of safety net actually contributed to my success – I HAD to hustle or else my bills would go unpaid. I know a number of freelancers with high-earning spouses and they tend to just kind of dabble in a few small projects here and there. They harass me and other successful freelancers about joining their “networking” groups but I can rarely make the meetings since I’m, you know…working.

  29. Pamela says 07 May 2014 at 21:07

    I’m shocked that so many people chose to comment on the word “tragic”. Did they miss the entire point of the article which was to show the pros and cons of self employment. I was so focused on and interested in the “actual content” of the article, that I honestly didn’t even notice/pay much attention to the use of the word.

    Holly – Thank you so much for the honest information. I’m currently pondering self-employment or. even better, early retirement. I gobble up useful information like this.

    • Diane C says 08 May 2014 at 12:39

      That’s great that you read Holly’s article that way, Pam. Here’s another take on that headline.

      Many of us have developed a level of concern for the well-being of each of the people who write here. When Holly used the word “tragedy” in her headline, their reaction may have been similar to my own. My immediate response was “Oh no, what happened?” Did someone dear to her die, or have a terrible accident or receive a terminal diagnosis? I scanned the entire article, ready to provide sympathy, empathy and appropriate support. What did I find? A load of whining about things she most likely knew of long before making her decision to go solo.

      Do I feel that the headline was misleading? Absolutely. The author and the editors of this blog used an overly dramatic headline calculated to play on our sympathies to get us to read the article.

      Do I feel used? Absolutely.

      Is this tragic? Fortunately not.

      However, crying wolf nearly always results in diminished support for the cryer’s future needs. I hope the author and the editors will heed the message of the many unhappy commenters.

      The poorly worded headline, as you noted, thoroughly obscured the point of the article.

  30. Viren says 07 May 2014 at 21:35

    One of my friend was extremely good as an employee. He was accountable and took the responsibilities with ease.
    However, once he chose to become self employed, he no longer had the same dedication. He was not equally accountable to himself.
    Guess what, he understood this quickly and got back to the 9-6 job.

  31. Gary says 08 May 2014 at 08:35

    Good article – I can relate because I myself am attempting to make the full leap. One thing you mention that is a stumbling block for so many people I think, and I really wish wasn’t the case, is this idea that “…once you leave there is no going back”.

    I really believe that is not the case nearly as often as people think. Since quitting my last two jobs, I have had multiple enquiries from both about coming back to help out. It is quite refreshing to know that is there if I want, and I bet it would be there for more people than not if they would just give it a try.

    I wrote an article on exactly this topic if anyone is interested:

    Thanks for all the great posts!

  32. Michelle says 08 May 2014 at 10:31

    Self employed for 10 years and going strong!

    I agree with many of the points in the post. Self employment is not for everyone — it has challenges and benefits like anything else. Knowing your strengthens and weaknesses can help you decide if it’s a good idea for you.

    One thing I would add — although paying my quarterly taxes is difficult, there is a benefit when it comes to business deductions. Internet service, client meals, mileage, postage, a new laptop — all deductible on Schedule C. Not to mention the Home Office deductions.

    I make more working part-time at home than I ever did working full-time for someone else. More importantly, I have flexibility that I can only get from self employment.

    That said, just because it worked for me, doesn’t mean it’s a good idea for you. As they say, “your mileage may vary.”

  33. TheGooch says 08 May 2014 at 19:20

    My experience is a testimony to how bad being self employed can be.

    I was pretty amazing at computer repair in my military service days, and all of my customers told me that I would make a lot more money going into business for myself. Eventually their praises brainwashed me to the point that I actually believed that if I started a business, I’d be the next Michael Dell.

    What actually happened is that did make some money providing computer repairs services, building customer computers, etc, but the profit fell far short of the expense. I blindly threw all of my personal savings into the business with the hopes that it would grow to support itself.

    Nope. It took my life savings, left me in debt, and asked for more.

    That’s when I rejoined the normal 9-5 workforce.

    Moral of the story? To be self-employed, you can’t just be good at producing whatever product/service your selling, you have to be good at strategy, marketing, finance, etc.

    You can make the greatest widget on the market, but if you cannot make people aware that it exists and convince them that they need to buy it, you’ll go broke.

  34. Even Steven says 08 May 2014 at 19:43

    I never really think about the corporate offerings that the 9-5 offer, while I’m greatful to be working and working towards financial independence, I would like to be in a position where these have no impact on my life.

    No 401(k) match –
    No social interaction –
    Work becomes “work” –
    No paid vacation –

  35. Jay says 09 May 2014 at 16:48

    In addition to PTO, which I think some folks classify as both ‘vacation days’ and ‘sick time’, don’t forget about holidays. No work = no pay.

    But I wouldn’t change a thing. Working as a rental is the best decision I ever made.

  36. Emma says 12 May 2014 at 04:56

    I find the discussions about language on GRS interesting, and as a writer I can sympathize with needing a thick skin! However, I think that thick skin needs to be tempered with an open mind lest it become arrogance. We don’t write just to hear the sound of our own voices, after all.

    A few times readers have corrected my terminology too, and some of them weren’t nice about it. One thing I’ve learned is that historically, people who have privilege control language. Maybe that privilege is you’re the dominant race, religion or sexual orientation – or maybe that privilege is you’re perfectly healthy or haven’t had anything truly tragic happen to you.

    I can think of a whole slew of words that were considered “acceptable” in my grandfather’s generation, but now are recognized as being demeaning or derogatory. Why? Because people spoke out about something they thought was wrong. They said “how you treat me and how you label me is not okay.”

    People of privilege often say “you’re too sensitive”, “It’s your problem” or “that’s just how I speak/write” — it’s easier to shut people down than be open to criticism. IMHO, we should listen to those who critique our language because often they know something we don’t.

    I wouldn’t have used the word “tragedies” either, but for an entirely different reason: SEO. Although, “comedies and tragedies of self employment” might have been a nice play on words.

    • Holly@ClubThrifty says 20 May 2014 at 13:29


      I just saw the rest of this conversation. I apologize for my late reply!

      You say that I’m a person of privilege, and I’m truly curious what made you reach that conclusion. I’m actually the product of a one-income household in a relatively poor part of the Midwest. I’ve endured an abusive marriage, a divorce, and two spinal fusions that left me unable to work or continue my education for an entire year in my early 20’s. I’ve worked as a waitress, a cashier, a house cleaner, and a nanny. I’ve been so broke that I couldn’t buy groceries or pay my utility bills more than once.

      The point is, I might be seen as a person of privilege now, but I certainly don’t feel like one.

      I actually never studied writing, literature, or journalism at a college level. I earned my many writing jobs through hard work and by never giving up. I also earned them by being myself, and NOT by letting others bully me into sharing their viewpoint or changing my words.

      I’m fine with others critiquing my writing. I actually enjoy a lively debate- even if others don’t agree with me. The comments section is an open mic, and I’m glad that people feel comfortable voicing their opinion. It would be very boring here if they didn’t.

  37. John says 13 May 2014 at 05:31

    So, let me get this straight: A discussion about the (debatable)exaggerated use of the word “tragedy” has now devolved into Emma vaguely comparing it to demeaning and hate-fueled terms and euphemisms used to describe race in the 1950’s and 60’s? She then goes on to wax poetic about how “privileged” people label others while simultaneously labeling the author as “privileged” without really knowing anything about her. Others have said that her use of the word “tragedy” is offensive to those who have experienced a “real” tragedy. Really? I feel like I’ve entered the PC Twilight Zone.

    Clearly, you read this thread of comments and saw it as Holly being “privileged” and dismissive. I read it as her not allowing herself to be bullied by a small minority of readers and not letting them dictate to her how she should write and react.

    IMHO, I think it is unfortunate that out of the thousands of people who read these articles on a daily basis, 5 or 6 people (female writers, apparently) continue to hijack the comments section in order to put on their own “Writing Master Class” to tear down other successful (mostly female) writers. Are your grapes really that sour, folks? Oddly enough, if they were to follow your splendid writing advice, they probably wouldn’t have gotten the job here in the first place.

    • Emma says 17 May 2014 at 06:40

      Thanks for sharing your point of view. A couple of points to clarify:

      1) As I pointed out, conversations about language have been happening on other posts, including J.D.’s. I don’t think we can dismiss people as jealous or say it’s women hating women – we really don’t know where people are coming from. I haven’t noticed those patterns with people who have critiqued my work, but that’s just my experience.

      2) I wasn’t just referring to race during a specific era. Think about how the language surrounding disabilities has changed over the decades. It’s not acceptable to say “retard” or “gimp” anymore, for example.

      3) We’re all privileged in some ways and not in others. I didn’t say privilege was a bad thing, just something we should to be aware of as writers.

      4) Why can’t we talk about writing on blogs? Bloggers blog about how to make money blogging all the time. Wealth/financial security (or a lack thereof) influences how we see the world.

      As I said, I’ve had my work nitpicked too. Many years ago, a reader took me to task for using the term “Eastern Europe” saying it was outdated and loaded with Cold War baggage. He had a good point and I learned from him. Sometimes I wonder what learning opportunities I’ve missed when I’ve been defensive or apathetic.

      I can only put ideas out there. People can take them or leave them, use them or attack them. It’s up to them.

  38. Diane C says 18 May 2014 at 22:49

    Oh Emma, I was hoping you’d respond to John’s impassioned screeching. Thanks for taking the time to clarify and defend your points. That was an awesome rebuttal. From now on I’ll make a point of looking for your comments, as you are very insightful.

  39. Abeesh Thomas says 02 February 2015 at 23:24

    My wife is self employed at In Singapore, Govt provides subsidies for self employment, e.g. no tax. IMHO, one must remain employed for a long time before taking the decision to be self-employed.

  40. Eli says 17 February 2015 at 11:42

    Being self employed has only one benefit. You don’t work like a robot or work horse. After the economy collapse advertising has fueled itself with greed starting with google . So now to advertise you need to pay google from $200 to $1000’s per month to get your business seen. Leaves only the big fish companies to take the 1st page listings. I have lost more than 50% off business, have lost my home, my credit and now am bankrupt . No forced to go out of business and the sad part about it is that some employers denied me a job because of my credit not to mention being self employed for 18 years is of no interest for most companies to get you hired.

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