Dream Job, Nightmare Income: Why I Still Freelance

Sometimes I’m tempted to go back to work full-time. Not because I miss working outside the home or because I feel the need to interact with adults more often during the day. Only because I want more money. What I make now is fine (forgive the melodramatic post title), but I have some lofty goals I want to accomplish that require more money.

I fantasize about going back to work while continuing to freelance on the side and bringing home an extra $3,000 each month that I can use for whatever I want. I dream about what I’d do with the extra money.

I’d buy a house.

I’ve been renting for 9 years and lived in 10 different places. Thankfully, I’ve stayed put the last 2 years, but I’m ready for home ownership. The trouble is saving up a down payment.

If I buy a house with $0 down, I’d be forced to pay private mortgage insurance (what happens when you have less than 20% equity in your home) and my monthly payment would be about $1,100. I would struggle to make that type of payment each month. Or, I could save up a 20% down payment and decrease my payment to about $750-$800 a month. That I could comfortably afford.

With an extra $3,000 a month, I could have a good down payment in less than a year. Plus, I could use the job to qualify for the loan and not go through the rigorous income documentation process I heard goes on when you try to get a mortgage as a self-employed worker. Double benefit.

I could pay off my student loans.

I’m carrying about $30K in student loan debt, you know, for the degree I used for all of three years. Though my college major was Management Information Systems, my degree came from a business school, so I did get a ton of business knowledge that helps with my freelance career.

Still, with an extra $3,000 a month, I could pay off my student loans in less than a year. In fact, if I went back to work for two years, I could pay off my student loans and have a down payment for a house.

I could buy a new car.

I’ve had my car for six years, but honestly, it feels like I just got it yesterday. My only complaint is that it’s a two door, which is often inconvenient considering I have a two-year old. I’ve managed though and as she gets older I expect it to get easier. But, if I ever have more kids, an extra two doors would simplify things.

One year at a job, plus freelancing on the side, would let me get the Nissan Murano that I love so much. Three years, and I'd have the car, the house, and my student loans paid off.

I could buy new furniture.

I could buy new electronics.

I could put more money toward retirement, college fund, vacation, clothes, shoes, hobbies…

…but would I be happy?

I see how people end up trapped in jobs they don’t love for years, how they wind up forgoing their dreams for the American dream. Even though more money would let me buy the things I want and achieve some financial goals, I’m happy where I am. I’m happier with less money freelancing full-time than I was with double the money and working for someone else. So despite not having as much money as I’d like, I keep freelancing because I love it.

Profile image for LaToya Irby
LaToya Irby is a full-time freelance writer and a graduate of the University of Alabama. She primarily writes about personal finance, freelancing, and other self-employment topics.

20 thoughts on “Dream Job, Nightmare Income: Why I Still Freelance”

  1. And don’t forget that you have another option — working to increase your full-time freelance writing income. Maybe what those financial goals mean (if your current freelance work can’t support them) is that it’s time to increase rates and consider targeting a new market segment. That’s one of the biggest perks of freelancing after all. Your growth is never limited by that “steady income.” I don’t know about you, but I’ll keep taking year-over-year double digit growth over “steady” income any day. If you’re not there yet, look for what you can change to make it happen. If you are, just hang in there — that growth adds up pretty darn quickly! 🙂

    • You’re right. That’s exactly what I need to do. It dawned on me as I wrote the post that I have the ability to get that extra $3K a month. I just have to do what it takes to get it.

  2. I work two jobs (as you know) and I do it for a number of reasons. The extra money is nice, but I really do it because I love the other job and I missed it when I stayed home.A third of the teaching paycheck goes to childcare and there’s not much to teaching to begin with pay-wise, so money isn’t a huge consideration. It is a safety net though. In fact as my hubby’s business dwindled and he needed to start fresh, I was really glad I had the two incomes.

    If you love what you’re doing for a career, by all means take on the day job because you’ll enjoy what you’re doing. If you really just love to write and you want to do that full-time, build up the business. If working a traditional job makes you feel trapped it’s not worth it if you don’t need it.

    I’m trapped at times by bills thanks to a big budget and spouse’s dwindling paycheck, but that won’t last forever and then I’ll still be teaching until I retire early to teach professional development (based on the educational theory book I have yet to write.) LOL I like teaching. So I teach. It’s more work, it’s more stress, it’s more money, it’s also very rewarding. I couldn’t say the last part about an office job though, so I totally get where you’re coming from.

    I’m with Jenn. If you don’t want to go back to work and you don’t need to, don’t. It sounds like you live comfortably as you are now. If you WANT to work in a different career at the same time, it’s an entirely different matter.

  3. Great post, LaToya. I think echoing Jenn’s post of last week regarding her car, freelancing does something we may not realize. It keeps us real. I hesitated BIG time when I decided to sell my eight-year-old car to my kid. Besides loving the car, I loved not having payments. I held on to that car because there was no good reason not to.

    We could do all those things with a “real” job, but would we? Hell no!

    BTW, my reward for a job well done is a new pair of shoes. I’ve been extremely good the past few years. 😉

  4. Nice post, LaToya. I really enjoyed reading it.

    I’m in a position at the minute that I thought I’d never be in. Having worked the same corporate job since 2006 whilst running my freelance writing career alongside it, I always said to myself that once I was earning from writing what I was earning from my corporate work for three consecutive months, I’d start to look at leaving to focus on writing full time.

    That time came…and passed a few months back. I did think about leaving – and I still do – but things change. I don’t love writing any less and in an ideal world, I’d be doing it full time. In the past few months, though, I’ve been given a pay rise (the company’s not doing great financially. Only three people in my region were put forward for a rise and I was the only one to get one – that was arguably the one time I’ve really felt it worthwhile working there), told it’s going to be a regular increment and basically explained that over the coming months the duties I don’t like doing will be taken off me and I’ll be given more time to focus on the ones I do enjoy doing and that I’m good at.

    So now I’m stuck with what to do.

    I want to write full time, there’s no doubt about it. But I’m struggling to walk away from the job that’s giving be a few thousand dollars each month, which I’ve been told will continue to increase.

    It is a financial decision – I’m not the type of person to sugar it up and say give some other reason. I don’t particularly like the job and the people, with the exception of one or two, are pains in the asses. But it’s relatively easy, hassle free and most importantly, it allows me to focus my time on my writing career without stressing too much if I don’t get a new gig.

    Saying that though, there’s only so much new writing work I can take on whilst working in the corporate role. I’ve managed to get my weekends back, but it’s coming up to half past midnight here, I’ve got at least another half hour’s work to do before I can turn the computer off and I’ve been at it since 7.00am this morning.


    • I know and respect your lifestyle Dan – I have it, too. If you don’t like your current job your decision to leave should be easier. As much as I love teaching now, I hated the two jobs I had previously. Nine years ago I took a huge pay cut to move into a career that I loved and even though it landed me with plenty of debt, I wasn’t sorry I did it. Now I have the benefit of two jobs I like and working with people I enjoy as well – I hope you find your happy medium and some happiness with your work decisions as well.

    • I remember feeling that way when I made the decision to leave my job. When I finally gave my notice, I felt like “It’s now or never.” Looking back, I actually wish I’d done it sooner.

      • The concern I have is that the past few weeks I’ve been wondering whether I’ve been trying to convince myself that I DON’T like working in the corporate world.

        I used to really hate it. Seriously. Getting up for work was an absolute nightmare. This was actually a big reason why I took up freelancing – I no longer wanted to feel like that.

        Lately, though, things haven’t been too bad and I’m kind of enjoying the office environment.

        But, writing is the career I want, which is the reason why I’ve been thinking about staying in both to develop a few ideas I have so that I can have that office environment – but in which i’m the one in charge.

        I don’t really know. I guess I’m thinking out loud.

        I love writing, it’s what I want to do, but I’m wondering if I could now look into incorporating the two things I like – the social side of an office but every aspect of writing.

        This blog really needs to be optimized for the “need someone to talk to” keywords. It’s great!

          • Hell yeah.

            I think that’s what I might do, actually.

            Rather than get up, put on my pants and shirt and make the 30 minute commute to work so I can have a moan to my colleagues there, I’ll just put on my pants and shirt and make the 30 second journey to my computer and AFW.

            In fact, I might just skip the pants bit. Again.

  5. Re qualifying for a mortgage as a freelancer, what I needed were two years of income tax filings. The bank cared how much money, not where it came from.

  6. The only part of working for someone else that I miss is being in an office around other people every day. But it isn’t enough to make me go back to work full-time at a “real” job. My stated salary would probably be much higher than it is now (since I have an MBA) but what I bring home would probably be about the same after commuting costs, a wardrobe of business suits, lunch out every day and full-time daycare. In fact, I may even come out much better with what I’m doing now. Either way, I’m staying put. 🙂

  7. You could also get regular health insurance!

    BTW, it always sounds easy to get that extra $3K, but it isn’t just hours, it is the “right” hours. Not many gigs come with the flexibility to get you the extra $3K without packing in some 14 hour days. (Why does everyone need things on Friday after giving back notes on Wednesday?)

    Brian Nelson
    Professional Freelance Writer

    • I think you bring up something a lot of freelancers quickly forget. They’re in business. If they’re serious about it, they’ll make sure they account for things like health insurance costs when doing their early market research and planning their target market and pricing strategies. The only reason a freelancer would need to take on a regular job for that benefit is if they neglected that aspect of starting their business. In that case they need to make a decision — go w/o the health insurance, forget solely freelancing and take the other job, or get their house in order business-wise and make the changes they should have made up front. There really are no excuses.

      And whether or not you can bring in an extra $3k or not each month really depends on the same thing — who are you targeting and are you charging the right rates for that target market? One monthly blogging gig with writing done on my own time brings in that much (no strict deadlines even, and certainly no 14 hour days — unless I choose to double up to take another one off). If someone’s charging $20 per post, they’re probably going to have a very different experience trying to earn that much extra each month, and it might not be possible for them. That’s another situation where it’s time to evaluate things and then either realize that you’re not cut out for it to the degree of earning what you really want to earn (right now at least) so you should take the regular job, or start fixing what’s holding back your freelance writing income.

      As for the Wednesday / Friday issue — I’ll admit I’ve had that happen quite a lot. Just another good reason I decided to no longer work on Fridays. 😉

      • Poor planning isn’t the only reason insurance would be an issue. Depending on where you live, even the best self-employment insurance doesn’t fully cover certain things.

        For example, a good friend of mine had to pay practically all of her maternity care and delivery charges out of pocket because she was a freelance photographer and her husband was self-employed. Had she had a job for just a year, she would have been able to pay a tiny fraction of that for the same amount of coverage. Insurance for the self-employed also don’t always cover any preexisting conditions and can be hard to arrange for children or adults with special needs. You would also have a very hard time getting coverage for psychiatric care – at least in Texas and a few other states I know of.

        Is that a reason to get a job? Not necessarily. Hopefully there is a way around the restrictions. However, plenty of people continue to work while they are pregnant and having children because they simply can’t afford to not have that insurance, and they don’t have the option under their husband’s plan.

        There are a lot of things that can be said about making the decision to quit a job when you’re single and young. Being relatively healthy and able to manage all of your own business and spending makes things easier, especially starting out. The same can be said for freelancers who are able to get insurance and other benefits through a spouse’s job (as many freelancing young mothers do thanks to maternity restrictions.) My point is that freelancing is a absolutely a business you have to plan for adequately, but the risks of going it alone have to be mitigated as life circumstances change.

        • It still comes down to planning. Planning to have children in the near future, or know it’s a possibility? Then it’s your responsibility to either secure insurance that will cover you (and I’d be beyond surprised if there’s nothing at all out there for the self-employed when you really look at all the options through unions, chambers of commerce, and other organizations these days), or make sure you have enough to self-insure yourself through that. The simple fact is that if you can’t make enough to truly support yourself, you’re probably not in a position to freelance full-time yet, at least not without some other options to support you. One of the biggest problems I’ve seen with new freelancers is that they don’t even consider these things before just jumping in, and then they act so surprised when they realize it’s nto the same as full-time employment. Of course it’s not. And being responsible in business means you know that going in and you prepare yourself for those challenges up front. Are there risks? Absolutely. That’s a part of being in business. Fortunately there are a lot of options these days to help freelancers lessen those risks. I don’t know. I think I’m just tired of seeing people jump into freelancing and then complaining that they can’t support themselves or can’t get insurance or this, or that, or the other thing, all because they didn’t bother planning and figuring out what they were getting into before doing it. Even if you’re thrown into it due to job loss, there’s no excuse for anyone to jump in ignorantly. I know LaToya personally probably understands the financial and insurance-related implications better than most simply because of her specialty area, and she was able to make choices in part because of that. I’m more thinking of those completely new to the game without that kind of background knowledge who don’t even attempt to understand some of these things until it’s too late and they’re struggling and / or ready to quit.

      • You were mentioning the things you COULD do. Getting better insurance for a much better rate would probably save you as much money each month as paying off your student loans 🙂

        I get health insurance through my wife’s job, and frankly, it’s the only reason she hasn’t quit yet.

        Unfortunately, no amount of planning can make up for the fact that only people who work for companies with group health plans get “real” insurance. You can’t even buy that kind of plan as an individual or small business. Good luck finding a non-group plan that covers ANY kind of maternity or delivery costs. Which is why I couldn’t figure out why the family values folks were against health insurance reform.

        There are TONS of hidden costs in freelancing. The one that is bigger than insurance is taxes. I can’t count the number of freelancers who get to the end of the year and have no idea that they owe approx 50% of their income in taxes (self-employment + income taxes) AND they also have no idea that they were supposed to be sending in tax payments as they went along each quarter. Those shocks aren’t pretty. Your only hope is to keep every receipt and rack up as many business “expenses” as you can.

        Of course, if it was easy, everyone would do it 🙂

        Llama out.

        • Some do indeed have maternity options available. I can’t remember if it was through the Freelancer’s Union or Media Bistro, but some of the health plans had that option (even if many didn’t) for freelancers when I was researching options for an article. So they’re out there. You just have to look a little harder to find them unfortunately.

    • Yep! And save $300 a month or rather put that money towards childcare, which would be necessary if I worked outside the home.

  8. LaToya, some years ago a friend (and then-colleague) was miserable at her job. She missed her kids, she wanted to do other things, but she felt bad leaving her boss. Her husband earned a good income, and she didn’t need the money. Yet she hesitated.

    I’ll give you the same advice I told her. This is not a dress rehearsal. This is it. There are no bonus points for being miserable.

    (She left. Turned out her husband told her the same thing).

    Oh, and eventually I took my own advice and left too.


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