How to Manage the “Dark Side” of Freelancing (aka Downsides)

So the other day a fellow freelancer shared this post on the dark side of the gig economy.

Naturally, I was curious. What was this “dark side” of the gig economy? Were there child labor slaves working at Uber? A conglomerate comprised of side hustlers funneling water from drought-stricken areas?

Nope, it turned out the post was about a recent study that reveals a huge discrepancy from the overwhelmingly positive portrayal of freelancing and negative comments on freelancing floating on social media.

And there’s no doubt there’s a litany of content floating on the Interwebs on how amazing freelancing is, where you have freedom to be a digital nomad, live life on your own terms as a #girlboss, ad nauseam.  I’ve been suckered into reading those articles, too.

And according to a recent survey commissioned by Freelancers Union and Upwork, while 79% of freelancers say that freelancing is better than working a traditional job, only 37% of freelancers who freelanced on the side would consider freelancing full-time. Why’s that? Well, there are plenty of reasons, such as financial instability, lack of benefits and insurance, and fear of failure.

The downsides of freelancing and self-employment definitely need to be addressed.  

First things first. Know that:

Freelancing Is a Preference. It’s Not Perfection.

This is something I realized early on. Being self-employed is sold to you as this ideal. But it’s not. There are moments when you find yourself hitting your head against the wall, and being a #girlboss is a hell of a lot more work than having a 9-5.

And freelancing isn’t for everyone. There are people who resort to freelancing out of pure necessity. And the growth of the independent workforce isn’t always made up of people who took the leap because their business was booming, or from choice. It could stem from the fact that hours were cut off from their job, they were let go, or full-time jobs in their field were becoming more scarce. 

You have to do what’s best for you at certain points in your life. And that may mean returning to a full-time job, or juggling freelance with a part-time gig. 

And while some people are more well-prepared than others to launch into freelancing, you can definitely develop those skills and traits to help you be successful.

Here are some of the downside of freelancing and tips on how to best manage these downsides:

Income that Fluctuates Like a Bipolar Mofo
Besides variable income, you’ll also need to deal with ponying up for your own health insurance, pay for self-employment taxes, and save for sick days and vacation. Here are some ways you can beef up your income and prevent getting hit hard from the perils of fluctuating income:

Seek retainer clients
This isn’t really for those who are independent contractors with 1-year gigs, or those who work on a single project for a period of time, but rather for those who are employed in creative industries, such as writing, marketing, or being a virtual assistant.

Have a robust emergency fund…
You can never have enough of an emergency fund. While the recommended amount is generally 3-6 months, I say if you can swing it, try to have 1 year saved up. I know, easier said than done. I can go into detail in a later post on easy ways to save for an emergency freelancer fund later.


…And a baby emergency fund

I had talked about having a “mama and baby emergency fund,” and a baby emergency fund can be anywhere from 1-2 months of your barebones expenses.

Try to stay one month ahead of your expenses
Umm.seriously? Really? Okay, this one’s a toughie. But if you can manage to have all the income you need for the following month, you won’t have to be on pins and needles, waiting for that paycheck to roll in from an employer. I think I also can afford to be a little more lax with when I invoice, although I do my best to stay on such matters. One thing you can do is save your extra beans in a separate savings account or with an app such as Digit.

Come up with a system that works—and stick to It
I’m huge on automating. I don’t really budget, because I feel fairly confident in knowing roughly how much I spend on average in a given month. But if you want to track your spending, there are a ton of budgeting tools out there, like and Level Money.

If you want to just create savings goals and automate them, you can try out Digit or Qapital. My friend Kristin has written a handy post on Qapital and how you can use it to automatically save money.

So my system may be complicated to some, but I have:

+ A business account where I deposit my earnings
+ A main checking account for my personal expenses
+ A long-term savings account for my short-term goals and freelancer taxes
+ A second checking account, one for groceries and household items
+ A third checking account, one for eating out and entertainment, aka “partytime” 

I also have a few retirement accounts, an HSA. For small savings goals I use Digit and just started playing around with Qapital for some saving goals. I know it seems like a lot to keep track of, but I automate everything and check in on it every so often to make sure there’s nothing suspicious going on.

Coming up with a system that works for you does take time. There’s no real shortcut. But the fun part is that there are bunch of tools sprouting up that can help you build out your system.

Dealing with Loneliness and Isolation
Yes, this is definitely a toughie. Sometimes my friends are in between jobs, or I organize work parties (aka coworking meetups) with a few buddies. But you can definitely deal with this in a bunch of ways.

Build your tribe. It doesn’t have to be in-person, especially if you live somewhere where there isn’t a vibrant freelancer community. I’m fortunate to live in Los Angeles, where, for better or for worse, not having a 9-5 is the norm.

Network.  In L.A. you can meet fellow freelancers at coworking meetups. I also am the L.A. organizer for Freelance Fridays, which is a free global coworking event for creatives and entrepreneurs. There’s also Built in L.A. events as well as Built in L.A. events in big cities in the U.S.

I’ve found great groups to ask questions, share my concerns and qualms on Facebook Groups such as The Freelancer’s Club by Careful Cents, Earn More Writing, and CloudPeeps.

Volunteer. You can stay connected with others through volunteering. Check out VolunteerMatch or to find organizations, or do a quick search on Facebook to link up with orgs that match your interests. I volunteer feeding the homeless, and it really is a lot of fun.

Managing Anxiety and Depression
I’ve long had to deal with anxiety, and when you freelance, anxiety can definitely be exacerbated and heightened when you freelance. You do have more you’re responsible for and more to worry about.

Self-care is crucial, as well as keeping a schedule. Life-work balance may go out the window at times, but you’ll need to stay productive. I try to meditate and exercise every day. While I don’t always manage to do this, I try to squeeze in mini-sessions. For instance, 10 minutes of stretching and resistance, or 10 minutes of meditation.

Things Can’t  Be 100% Awesome Time
This is a general rule of thumb in life. And when you’re freelancing, when things are awesome, you’ll get a thrill at working for yourself. And when they’re not, well, you will need to know that’s just part of the path you’re on. Having a backup plan can help, and just being aware that, yes, you’ll have slow months.

Freelancing is an Exercise in Practicing Patience
You’re not going to land amazing clients at the same time overnight. Nope. It definitely takes time to seek out opportunities, build rapport, and the like. Or if you’re trying to come up with a new way to make money or find clients, you may need to toss a bunch of things against a wall and see what sticks. I’m dealing with this right now, and little ventures I’m trying out for the first time feels like a waiting game.

But knowing exactly what the downsides of freelancing are, you’ll be able to better manage them.

Set Your Estimated Taxes on Autopilot

By Argel Sabillo, Levee

Freelancers are all hustling to do one job: Make money. They are balancing the creative process with client expectations—the last thing on their minds is paying taxes. Consequently, many freelancers ignore the fact they are required to pay estimated taxes four times a year until tax time comes around and the tax bill adds up to thousands of dollars.

Avoid the headache and make your money work for you. Put your quarterly estimated taxes on autopilot so you can focus more on the creative side of your business.

Here’s how in three simple steps:

1. Find out if you even have to pay.
According to the IRS, if you earn self-employment income and your tax bill is going to be $1,000 or more, then you have to make estimated tax payments. Easy translation—if you profited over $7,100 in freelance income this year, then you are required to pay.

There is one exception. If you had $0 tax bill last year, are a U.S. citizen or resident for the whole year, and your prior tax year covered a 12-month period, then you’re off the hook from making quarterly estimated tax payments this year.

2. Estimate what you owe.
The IRS requires that you pay at least the 100 percent of last year’s tax bill or 90 percent of this year’s tax bill—the lower of the two—and evenly spread those payments over four quarters in order to avoid the underpayment penalty.

There are three ways to estimate your tax bill and they vary in accuracy.

You can set aside 25-35 percent of your freelance income toward estimated taxes in a separate bank account. If you underpaid your taxes, you’ll have a few hundred to cover it. If you overpaid, you’ll get a nice refund. You can then adjust for the next year until you save the right amount.

A little more precisely, you can estimate how much profit you expect to earn for the year and calculate your estimated income and self-employment taxes based on this number. Divide it by four and then pay an even amount quarterly. These payments might not reflect your actual earnings each quarter, but should be close to the end-of-year total.

Here’s an example. Say your annual freelance profit is $90,000 (column 3). Your annual tax bill is $26,776 (column 4). Your estimated tax bill would have been four equal payments of $6,692 (column 5).

Table 1-A.

Quarterly Profit Annual Profit Annual Tax Quarterly Tax Bill Running Total
1st Quarter $22,500 $90,000 $26,766 $6,692 $6,692
2nd Quarter $22,500 $90,000 $26,766 $6,692 $13,384
3rd Quarter $22,500 $90,000 $26,766 $6,692 $20,076
4th Quarter $22,500 $90,000 $26,766 $6,690 $26,766
Total $90,000        


Meanwhile, there’s a more complex and accurate strategy. Calculate your estimated tax bill every quarter based on your freelance earnings and expenses every month. Freelancers know — it’s feast for famine, and this strategy is ideal for uneven income streams.

Here’s how it works. Say your freelance profit is still $90,000 (column 2), but the range fluctuated between $60,000 and $100,000 (column 3). As a result, your estimated annual tax bill (column 4) and your quarterly estimated tax bill (column 5) also fluctuated. But the estimated taxes you owe (column 6) still add up to your final tax bill of $26,766.

Table 1-B.

Quarterly Profit Annual Profit Annual Tax Quarterly Tax Bill Running Total
1st Quarter $15,000 $60,000 $15,557 $3,889 $3,889
2nd Quarter $25,000 $80,000 $23,029 $7,625 $11,515
3rd Quarter $35,000 $100,000 $30,502 $11,362 $22,877
4th Quarter $15,000 $90,000 $26,766 $3,890 $26,766
Total $90,000        

Why take the complex approach? You get to keep more of your money in the first quarter.  To do this, you have to be diligent with
tracking your income and expenses.

If you aren’t using a tax app like Levee to automatically calculate your estimated taxes, you can use Form 1040-ES to calculate your bill manually using the moderate and complex approach.

3. Know how to pay.

You can pay the old-school way by sending a certified mail of Form 1040-ES along with a check or money order to the IRS. Or you can pay easily online through their payment portal, EFTPS. If you’re making equal payments and don’t want to miss the deadline, you can even set the payment dates to automatically debit your bank account. Here’s the important tax deadlines:

For the period Due date
1st Quarter Jan 1 – Mar 31 April 15th
2nd Quarter Apr 1 – May 31 June 15th
3rd Quarter Jun 1 – Aug 31 September 15th
4th Quarter Sep 1 – Dec 31 January 15th (following year)

You can also pay via mobile by downloading the
IRS2GO app.

Keep in mind that these tips are only for taking care of your federal tax bill. You have to take care of your tax bill with the state government where you do business. You can find links to your state’s tax office here.

So in three easy steps—made even easier by an app like Levee—you can put your quarterly estimated taxes on cruise control, make paying taxes a breeze, and keep more of your money. Download Levee now to start automating and get the first month free. 

How Freelancers Can Help Each Other Make More Money

As I’ll be focusing on friendship this month, I’ve been thinking a lot about how freelancers can help each other out, particularly with raking in more moola. During my first full year of freelancing, my friends have been my bedrock. They’ve been there to commiserate about everything from assignments from hell to stressful times.

We also have a lot of fun. We get together to cowork and enjoy cheap eats at happy hour. And guess what? We’ve also helped each other boost our income.

Here are some ways freelancers can help each other make more money:


Refer Fellow Freelancers
If I feel as if they’re a solid fit, I’ve referred writers to publications I write for and they’ve also done so in kind. If you see a job opportunity that is up a friend’s alley, pass it along to them. It doesn’t take too much time to write a quick email and a few kind words about your freelancing colleague. I have a freelancer friend who created a spreadsheet to log her friends’ different types of expertise, in case a gig comes her way that she’s not a good fit for.

Be Transparent with Your Rates
This is crucial. The thing with freelancing is that rates can vary wildly. It’s not like being, say, a doctor or lawyer where there are standard rates and you can get legit numbers on how much you should get paid for things. And while there are some databases on freelancer rates such as the one from the Editorial Freelancers Association, but they’re super general. How much you get paid can depend on whether it’s a corporate client or a startup, how much experience you have underneath your belt, and your niche.

As I mainly write about money, I can’t compare the rates for writing for a fashion blog to say, an investment company. Any freelancer will tell you there’s really nothing worse than lowballing yourself. My fellow personal finance writing friends and I shoot the hay about what certain clients pay, how much to charge for X words, and so forth. There’s so much to consider when negotiating rates and it really helps you have friends who disclose what they know about rates and to give you their recommendations.

Don’t Lowball Yourself
Sure, we all have weak moments. We might have had a shitty month, and could use the money. But when you lowball yourself, you’re hurting fellow freelancers who work in your field. Think of it this way: if freelancing can be compared as a produce stand, and there are a bunch of oranges, which all look pretty similar.

Hire Fellow Freelancers
When building your business, you can hire fellow freelancers as virtual assistants (VAs), and to lend a hand with proofreading, researching, photography, and graphic design. I’ve hired my friends to design my business cards, help with photo research, and do fact-checking. This supports the gig economy, and help your friends sustain themselves.

Create an Anti-Feast or Famine Collective Work Group
This is an idea I’ve had for a while and have yet to implement. Along with hiring fellow freelancers, the gist is to help your freelancer friends get through the periods of famine. The concept is pretty simple: if you are slammed with work, and could use help with research, fact-checking, outlining and what have you, then you reach out to the group of fellow freelancers to see who is available.

You then suss out the details, such as the going rate, scope of the “helper assignment,” and how many hours you think it will roughly take. That way your periods of famine potentially won’t be as awful as it could be.

Give Them a Shoutout on Social Media
Share their posts, spread the word about a talk they’re giving or ecourse they’re creating. There’s nothing more powerful than what others say about you. It costs absolutely nothing to spread the love on social media. You can also buy their shit and vouch for its quality.

What are some ways you can help fellow freelancers earn more money?


Photo credit: Alexis Brown / Unsplash

My First Full Year in the Hustle: Freelancer Wins and Fails

Illustration by Viet Vu

This marks my first full-year as a freelancer. And while it definitely wasn’t always easy, I managed to get through it. There were times when I suffered massive anxiety and thought about getting a job at See’s Candies (my teen dream job, no joke). But the truth was, I was doing fine. I was landing clients, worked my butt off, which eventually led to netting a pretty solid income.

What’s funny is that a lot of my more seasoned freelancer friends tell me that the first year making a go on on your own is the hardest. And while I politely nod in agreement, I can’t help but wonder, “What could possibly change the second year? And in the third?” To be honest, I am not even sure if I feel that much more confident. Obviously, there will always be unknowns, and that will never change. That being said, looking back I learned a lot about myself, upped my freelancer game, and have set things in place to make it a bit easier for 2017.

If life can be neatly compartmentalized and labeled as such, here are some of my top wins and fails this year:

Win #1: Making more money than at my old day job. While this wasn’t necessarily a goal of mine, I was curious as to how much money I could earn going solo. Despite working less and having a few slow months in the spring, I managed to net more income my first 10 months of the year than what I was making in an entire year at my old day job and working less hours overall. I decided to “take it easy” the last few months, only to discover how much of an fretful workaholic I am.

Of course, I will need to factor in expenses that are a part of being self-employed (i.e., self-employment tax, health insurance, business expenses), but it feels pretty awesome to know that I can pull off making money on my own.

Income goals are great; they make sure you are able to eat, and that you can sock away some money toward all the fun and cool things you want to do. I try not to tie too much of my identity into my income. Knowing that your income can fluctuate wildly has kept me most grateful and humble.

The question I get asked the most is “how can I get started making money as a freelance writer?” and in the new year am excited to share how I make money writing, and tips on beefing up your income.

I’ve also grown a lot as a writer. I’m now spend about 4-5 hours a day writing, and as writing is a muscle and a craft, I feel as if I’ve learned a lot, from SEO keyword best practices to branding guidelines. Plus, I’ve been on editorial teams with some super talented editors and content strategists. I’ve learned a lot from working with different people with different editorial backgrounds. And to boot, my writing portfolio is definitely more robust than it was a year ago.

Win #2: Learning to work in different locales.
While not a huge traveler, I’ve been able to see more of the world than I have in previous years because I didn’t have just 2 weeks of paid vacation. Of course, any time I took off from work was unpaid, but being the Cheapster that I am, I made it work.

Whether it’s been at a McDonald’s in Joshua Tree, a train en route to Chicago, or a coffee shop in Honolulu, I’ve tried out different schedules in different time zones to get my work done. I’ve had to do the 2/6 schedule, meaning I work 2 hours, then take the rest of the day off, to stay afloat.

Win #3: Coming up with a solid budgeting system.
After experimenting with different systems, I’ve figured that the percentage method is what works best for me. This has helped me make sure I have my monthly bases covered, and that my other money goals are slowly chugging along. I am a firm believer—in fact, I know—that creative types can totally conquer handling their moola.
I’ve been able to invest on the regular in stocks with Vanguard and the Acorns app, and sock away money in both a Roth IRA and SEP IRA fund.

I also opened an health-savings account. My friend Kate over at Cashville Skyline has written a great post on how HSAs provide a triple-tax benefit. Plus, it’s nice to have money in case unexpected medical bills creep up.

Top Win:
Realizing how much I really need a community. Whether it’s reaching out to a fellow freelance writer to talk about rates, or meeting up with pals for a work party, I need people. My friends have kept me anchored when I was stressed to the balls and provided help when most needed. I’ve been able to meet some great people through Freelancer Union’s local Spark events, and through Freelance Friday meetups in Los Angeles.

In 2017, I would like to focus on community. How to build a community online, and sharing info and resources with freelancers and artists in person and digitally. I’m super stoked to figure out ways on how we can help each other stay sane, grow, and learn.

Fail #1: Not spending enough time on personal projects. Ah, the eternal struggle persists. Part of the reason I decided to do this whole crazy freelance thing was to make more time for my creative stuffs. You know, live the life of someone who could wake up and really focus on improving their craft.

Well, that was an idealized notion that vanished in two seconds flat.

Besides getting a Cheapsters ‘zine out with the tremendous help of my dear cousin Viet and making some headway on some short stories, I didn’t spend as much time as I would like to on creative projects.

Why’s that? Well, money is a huge motivator. That being said, the times when I had a lull, I was so anxious about finding work that I didn’t allow myself to just relax and work on other stuff.

So this next year I would like to devote more time on my creative projects. I think 15 minutes 6 days a week is totally doable. Perhaps right before I start my work, or in the afternoons.  I can definitely bump it up as I get deeper into my projects. Here’s what I would like to work on:

+This blog! (woot.)
+ (Not so) super secret book series to help artists with their $$$$. More details to come!
+ Fiction: Short stories in particular
+ Music: Learn basic audio engineering, improve my guitar skills
+ Random art projects

I know. It’s a lot. And I need to seriously sit down and allocate time to specific projects. But it is a wish list! But wise person said if you get a wish out into the cosmos, the universe has a way of conspiring to make it happen. That might just as well be a bunch of mumbo jumbo!

Fail #2: Not having a freelancer contract. We all know how getting a freelancer contract can help you earn and save more money, but it also is there to protect you. I learned the hard way when a client changed the author of a blog post I wrote to his name. Having only signed an NDA before working with this client, it wasn’t clear who owned the rights. As a result we parted ways—and not amicably, either.

In hindsight, having a freelancer contract I could give to clients when I first work with them could have totally prevented this from happening. Womp. So in the new year I plan on having my own contract, to make sure all bases are covered.

Fail #3: Not getting enough sleep. Seriously. I’ve been struggling with insomnia and sleeping problems for a long time, and freelancing has only made it worse. There have been countless times when I’ve sacrificed sleep, waking up at 3 or 4 a.m. so I can hit all my deadlines. No bueno. Am gonna really try to improve this in the new year, and get my Zzzs!

!!!Top Fail!!!
Lack of work/life balance. Well, it’s weird. In some ways I’ve had more free time, but the crazy ebbs and flows of freelancing, really created a lot of unnecessary stress and anxiety. As Carrie Smith of Careful Cents says, you either need to embrace the craziness,  or try to find a way to strike that ideal balance.

Although I am generally an anxious person, I’m stoked to see how the new year shapes up!

What were your major freelancing wins and fails this year?

*This post may contain affiliate links. I only give shout outs to products that I use, love, and can get behind.


How to Get Paid to Write When You’ve Never Been Published

The question I get the most from my friends is: How do I get paid to write?

I’ve been a writer in some capacity for a long time, it’s only been the last few years that I started to get paid for it.

While I’ve worked in editorial in some capacity for the last decade, I haven’t gotten paid for most of the writing I’ve done. When I first got out of college many moons ago, I wrote for for free (or for very little money) covering local music and restaurants for blogs and weeklies. And for the last 10 years or so I’ve been hard at work learning the craft of fiction. Although I enjoyed it immensely, these things never paid the bills.

I started earning side cash back in 2010 by copyediting an arts magazine and proofing books for self-published authors, and doing one-off copywriting jobs here and there. It felt great to earn some side cash. I was able to put that money toward vacations, new computers, or to use as “get ahead money.”

I spent about $800 for a certification in copyediting (my employer at the time was generous enough to subsidize for half). I made a pact for myself that I would need to find a way to earn that $800 back, I could call it even. It soon paid for itself and I can easily say it was one of the best investments in myself that I’ve made.

And although I officially started freelancing full-time as a writer last year, I got my first real gig as a freelance writer in the fall of 2014 through a content platform called Contently. Contently connects creatives (i.e., writers, designers, motionographers) with brands to create content for their marketing campaigns. I hands-down love Contently. They gave me my first real break as a professional writer and they look out for the talent.

It was at FinCon, a conference for people who create content about money, that I realized that personal writing was blowing up. I mean, I knew there was a slew of personal finance content online, but I didn’t realize how closely the financial industry paid to the money blogger community. I had initially created this blog to assert my frugal ways, to find like-minded folk, and to help others. I was essentially living in a bubble until I attended that conference.

Within my first month with my client I received a bunch of assignments and worked my butt off while maintaining my day job. It turns out I was making nearly the same as one month’s salary at my day job. And that was just from a single client. I quickly saw the earning potential of freelance writing.

So here’s everything I know (thus far) about how to get paid to write when you’ve never been published. I hope that you get something out of what I’ve learned so far.

Step 1. Figure out your niche
This is essential. Figure out what kind of subject matter you want to cover. There are about a billion places you could write for. This will help you narrow it down to writing about things you are better suited and qualified for, and helps better your chances of getting your foot in the door.

For instance, my friend Joel owns a dog walking business, and has spent a lot of years learning about dog behavior. He’d be great for writing on pet sites and dog blogs. Jeff has experience writing reviews on comic sites and is a huge comics nerd. His area of expertise is more along the lines of pop culture and all things nerdy.

You’ll also want to ask yourself these questions:

1. How hot is this market? Are there quite a few outlets that are willing to pay for content?
2. How qualified am I to write about it? The joy of writing is that you don’t necessarily need a fancy degree. You just need to show that you can do the job, and do it well.
3. Do I have any valuable contacts that would make for good primary subjects (interviewees) for pitched articles?

Step 2. Figure out which outlets you want to write for—and whether they pay
It’s best to narrow it down to a handful of outlets that you want to write for. So how do you figure out if a publication pays? Sometimes a site will have a “Write for Us” page where you can get more info or contact someone in their editorial department. They might mention whether they pay their writers. You can also check out Contently’s Rates Database. Some of the freelancer rate charts can be misleading because it depends on a host of factors, such as the niche and how closely connected the publication is to generating revenue for a company.

Another way you can figure it out is if there are clearly advertisements on their page. This can be in the form of banner ads, or more likely, through sponsored posts and affiliate links. Just because they may be generating revenue doesn’t mean they necessarily pay their writers.

You can also look at the roster of contributors. Check out their bios and do a quick Google search to see which other outlets they write for. Do they write for places that pay? Places that probably well pay, or just okay? I’ve been lucky to oftentimes know people who write for certain outlets, and can reach out to them to see how they like writing for a certain publication and if they pay by word or post. A lot of it has to do with network and niche.

Step 3. Create some writing samples
Better yet, post these on an online portfolio or to your blog.  A blog can be a money-making vehicle in itself, but it’s a great way to learn about what you’re all about. It can also provide an outlet for making friends and connections, and be a testing grounds of sorts to try out new ideas.

And look beyond the major publications you know and love. Think about places that could pay you to write some marketing copy for a brand. Some sites you can check out:

The BackScratchers

I can only vouch for Contently, as that’s the only site I’ve landed work through. Sites like Contently and Skyword have free built-in portfolios, so if you don’t have a professional website up yet, you can link your sample work on those platforms.

Even if you’re just starting out, I would steer away from low-paying content mills.

You can also write for company blogs. Check out a company’s site and if they have a blog, they may hire freelancers to contribute. It doesn’t hurt to send an introductory email to their advertising director or head of content.

Step 4. Come up with story ideas
Study the publication. If you don’t already, follow it on social media. Read the articles, figure out what the style, tone, and voice are. Subscribe to the newsletter. You can get an idea for a publication’s vibe and message.  You really need to do your homework. There’s nothing worse for an editor who is knee deep in the deluge of story pitches to get a set of pitches that show the writer doesn’t know the publication well. Make sure your pitch doesn’t go in the trash. When you pitch stories, make sure your ideas are a great fit for their content, editorial objectives, and is something you feel comfortable pitching.

I have made the mistake of coming up with what I thought was a super clever idea, then get the assignment, but realized I wasn’t able to really make it work. It really makes you come off as an amateur, and it’s really wasted time.  If you’re in doubt, do a bunch of research, think about who you would interview, and draft an outline.

Pitch appropriately.
Make sure it’s a right fit for the publication, and that it might offer something slightly different to the publication. If it’s a product blog or trade publication, you might pitch to the director of marketing. If it’s a traditional outlet, you’ll most likely pitch to the managing editor. There’s a ton of articles out there on what makes a good pitch. I found that a solid headline, and a succinct pitch of 2-3 sentences outlining the idea and some of the main points you would cover, work best.

You might feel intimidated to pitch to the managing especially if you’ve never done it before, but having sample work you can show them and letting them know how exactly how you’re qualified to write about a particular topic will help you get your foot in the door.

Step 5. Create sample articles
Imitation is a form of learning. Follow the format and layout of existing articles and write a sample article accordingly. Of course, you can write in your own style, but formatting an article to adhere to existing blog posts shows that you’re paying attention to the details. I once had an English teacher that made us rewrite our essays until we earned an ‘A.’ Do a few round of drafts until you feel as if you’ve nailed it. If a publication offers a style guide, make sure you look it over closely.

How much should you charge?
I say charge as competitively as you can.  If you’re off to a strong start, you can use that rate as leverage when you negotiate rates for the next place you write for. Oftentimes established sites have set rates with very little wiggle room. If you’re a newbie, you might feel compelled to charge less. My first client paid a very competitive rate, and that’s helped me set my rates to be fairly competitive. Sometimes articles require a lot less research, are a lower word count, and less work overall. In that case, a lower rate may feel worthwhile to you, especially if you can churn something out quickly.

The bottom line is to charge a rate that you are excited about.  If you are just starting out, getting paid $30–$50 for an article might be enough for you to get juiced up and turn in killer work. However, if the rate is too low in your book, you won’t be motivated to turn in quality stuff, and you probably won’t want to stick around for long. Good managing editors know this, and they want to make sure rate feels fair for both parties involved.

What if an outlet doesn’t pay? Should I still write for them?
In the freelancer community, “writing for exposure” is known to be a cardinal sin of sorts. And I can understand why. By writing for free, you’re undermining your talents and in some ways devaluing the field at large. I would say avoid working for free if you can. Sometimes places dangle that proverbial carrot over your head that you write for free now, it could potentially lead to paid work.  But if they can get you to work for free, why would they bother to pay you? And if they paid you, would it be sufficient pay? I have heard instances where an internship does lead to a paid position. I’m just saying you can’t always bank on it.

I know some established writers who write a single post for free because it was good exposure and was a great addition to their portfolio. It’s totally a judgment call, and a personal choice. You get experience working with an editorial team. Could it help you expand your network of contacts? Could it get into conferences or conventions that could lead to paid work? Do you get a byline?

Just remember: If you can make your first $50 writing, you can earn your first $100, and so forth.
Happy writing and good luck! 🙂

A Few Half-Truths About Freelancing

Now that I’m hitting my five-month mark as a full-time freelancer (yikes? hooray?), I’ve been reflecting about what I used to think freelancing would be like what it’s actually all about. You might even compare it to seeing something in a movie and then experiencing it in real life. For instance, daydreaming about, say, sliding down a snowy hill on piece of flat cardboard, and the act of doing it, where the snow is most likely icy and hard rather than the soft, powdery stuff.

Here are some misconceptions I had about the world of self-employment:

It’s Either Feast or Famine
Sure, there are times when you’re incredibly busy—and then there are times, not so much. When it comes to how busy you are, there are also a lot of gray areas. For instance, say you’re working at a steady clip, and you have enough clients to get by comfortably. And then an opportunity comes your way. It’s not a job that you’re extremely excited to take on, but it’s also not one that you make a “whoa that smells super bad” face at, either.

You hypothetically have the bandwidth to take it, but at the same time taking on another gig cuts into time you could be spending working on a passion project or just piddling around doing nothing. Of course, this is the freelancer’s equivalent of a champagne problem. So you have to gauge whether it’s worth it to you.

Say you could really need the money, but your heart isn’t into it. You might risk passing up an opportunity that comes your way or do shoddy work because you just didn’t care about the project. In that case, even if you’re low on funds, the money might not be even be worth it.

You Are Your Own Boss
Well, you’re self-employed, meaning you get to handle your own accounting, health insurance, and self-employment taxes. Congrats! Just kidding, sorta. While you technically are your own boss and can decide whether to accept a gig or work with a client, conversely you have like five bosses, all with different demands and schedules. So you’re going to have to do a bit of a juggling act. Depending on what work you do, you still have to meet deadlines and turn in quality work that your clients are happy with.

You’ll Generate Tons of Money from Multiple Streams of Revenue in No Time
Okay, maybe it was just me who thought this. Although I have been extremely fortunate at landing new writing gigs and clients, I can’t say I’ve been able to rake dough through seven different channels of revenue, which is the online buzz on how to become a self-made millionaire.

Because the potential is there so create a new platform (i.e.,YouTube series, podcast) and products (i.e., affiliate marketing, online course, self-published ebook), there is also the reality of how much time it takes to produce a new platform, product, or service. I’ve been a lot more careful about choosing long-term projects because of how much time I’ll need to invest in such a venture.

A few years ago I was obsessed with the idea of creating an Etsy shop. One of my best friends was kind enough to talk me out of it, reminding me of how much work it takes to build a business. Making the products is one thing, but building a platform and an audience is an entirely separate game. I went so far as to purchase the domain and created social media accounts before I realized that I really didn’t have time or audience to make it work. I was glad my friend was real with me and gave me a reality check.

You Get to Lounge Around All Day in Your PJs
You could wear sweats and nobody would care, but you’re also definitely hard at work. And while you do have a ton of freedom and flexibility in how you structure your time and make your money, you need to be super disciplined at staying on top of things.

I’ve been able to stay afloat as a freelancer by doing a combination of copywriting for the web, personal finance writing for blogs and corporate brands, and picking up hours at my old job. (I’ll get more into creating a CRM, or Customer Relationship Management strategy in a later post.) Right now my personal finance writing is growing a lot, which is pretty awesome. But it’s definitely work, and focused work at that. Meaning you don’t get paid for going to the bathroom or hanging around the water cooler.

Since I’m still relatively new to being self-employed, I’m sure I will uncover more half-truths about freelancing along the way.

What misconceptions did you have about freelancing?

Four Ways to Structure Your Time

One thing I’ve been trying to figure out is how to best structure my time. I must say, I’m pretty awesome at tracking my time on assignments, but structuring my time within a given day is an entirely different story. It’s definitely in an experimental phase and I expect to keep trying out new things along the way. If you’re in the same boat as me, here are a few ideas to try on for size:

1. Sprints
My good friend Julia (and retirement goals buddy), who works in UX gave me this idea. As a UX designer her team works in two-week sprints, which is a period of focused, high-intensity work. Two weeks might be a bit much, so you can either organize your time to work in what I call a Mega Sprint, which is the badass version. With a Mega Sprint you crank away for a couple of days or even a week.  You can also do a Baby Sprint, which is working at high-intensity for a day or so. I did this a week ago and was surprised at how much work I managed to get done.

You may do a sprint out of pure necessity, or out of choice. Depending on how much work you have on your plate, you might be able to get a week’s worth of work done in a few days.

2.Top Load
I’m an early bird, and my dream schedule is getting most of my work by early afternoon at the latest. As I am working onsite for a gig for another month or so, I won’t be able to try this out until mid-April or so. On days when I work entirely at home, I am usually up by 6 am, work on my fiction and this blog for a bit, then start my freelance work. You can top load within a day or within a week.

Bottom Load
Conversely, you can also bottom loading, which is great if you’re a night owl who loves to burn the midnight oil. This is definitely not me, as I tend to get super groggy around 9 pm or so.

This is what I thought might work best for me, but have been having trouble sticking to it. The Half/Half approach is when I do a block of work in the morning, then take a mid-day break when I exercise, eat lunch, and run errands, then do another block of work in the afternoon. When I do this I tend to have a hard time settling back into work mode after the midday break. I think on my full days when I work from home I am easily tempted to run a bunch of errands or work on other things.

I love to keep my days loosely structured, meaning I’ll have a list of things I need to knock off in a given day, and then kind of do a mix of writing, admin/invoicing, sending out emails, and chores. I know some people like Cait from Blonde on a Budget likes to take one day off during the week and Saturdays, which seems like a pretty cool setup. 

 My schedule has been feeling a bit crazy lately, and once I get a grip on things I would definitely like to play around with different ways to structure my time. Ultimately it’s up to you to figure out what works best.

How do you like to structure your time? Any suggestions?

What It Means to Be a Minimalist Freelancer

As someone who practices Zen Buddhism and minimalism, I’ve been thinking a lot about what it means exactly to be a minimalist as a freelancer. To be being minimalist has to do with your approach and mindset to how you work. It’s about getting rid of what’s not important to you.

And as I’ve nearing the end of my 4th month doing it full-time, I wonder what I could do differently in the future. How can I better align my values with the craziness that comes with being self-employed? I am definitely still figuring that out. Here are some things I am going to keep in mind going forward:

In Your Work
I touched about this briefly in a previous post about optimizing, not maximizing your life. It’s about not taking everything that comes your way—you can afford to do so, of course. Nix projects and clients that add unnecessary stress in your life, or aren’t building your portfolio. Instead, take on work that is either meaningful, pays enough so you can work less and focus on other projects, or could lead to more meaningful work.

Of course, this can feel like a pipe dream but it’s definitely something to aspire toward. Sometimes you have to take a job simply because you need the money or are a regular workhorse who has problems saying “no” to work.

In Your Tools
Do you really need five project management programs and three tablets? I’m all for implementing apps and tools to enhance your system and processes as a freelancer, but too many tools can make your workflow a bit cumbersome.

You might find that you can do more with less, or be smarter about streamlining your work with just a couple of programs. The main tools I use on a daily basis are Evernote for my to-do list, Toggl to track my time, and Freedom, which is an Internet blocker I use when I am writing fiction. All these apps are 100 percent free. And I am landing more clients and gaining more ways of earning money, I am also looking into streamlining how I do my billing and track expenses. It’s starting to get a little messy. Oof.

In Your Digital Communication
This is something I struggle with daily. If you’re like me you have a million articles on your Facebook Newsfeed saved, subscribe to the newsletter of every blogger and website you dig, and check your email compulsively. I’ve installed Periscope, Blab, and Meerkat on my phone and pretty much every single new social media platform out there. And do I use even a fraction of them? Nope.

Try checking and responding your emails just a few times a day. For instance, when you first start your work day, before lunch, and about an hour before you’re ready to wind down. Doing your tasks in batches can help a ton.

In Your Approach
This is probably the biggest thing I have been struggling with. Pay attention to the task at hand. Don’t take on too much in any given day. It’s easy to feel overwhelmed, to wish you could get all your work done in one fell swoop. Take your time, don’t rush. Take breaks if you need to. Go for a walk, or a short swim at a nearby pool.

If you’re curious to learn more about minimalism, here are a few resources to get you started:

The Minimalists: Joshua and Ryan of The Minimalists have really started a culture on how we can live more fully with less. They have local meetups in different cities around the world where you can shoot the bull with like-minded folk. Joshua’s book, “Everything That Remains,” is a memoir that chronicles his path from living a crash-and-burn, materialist lifestyle to a deliberate, minimalist life.

Blonde on a Budget: Cait Flanders is currently going through her two-year spending fast. It’s inspired me to go on my own version of a spending fast. She’s pretty awesome and inspiring.

And Then We Saved: Anna Newell Jones is the queen of living a life free of material distractions. She shows you going on a spending fast can be done. Besides a bunch of articles on her site, you can also glean tips on how to go about on your own spending diet with her upcoming book “The Spender’s Guide to Debt-Free Living.” She’s also just put out a book that includes wisdom on the minimalist lifestyle as well as interviews with some of the heavy hitters called “How to be a Fearless Minimalist in a Cluttered World.

Zen Habits: Leo Babauta is the man when it comes to creating habits to live a healthier, more meaningful and productive life. I have been following his site for years. He teaches you how you can create real change in your life by changing your habits, little by little. Check out his book “Essential Zen Habits, Mastering the Art of Change, Briefly,” which includes super short chapters on how you can change your bad habits and do all the things you’ve ever wanted to. I got through the book in a couple of sittings and it’s one that I come back to again and again.

The Freelancer’s Guide to the Galaxy

If you’re new to the world of self-employment, you may feel as if you’re stepping on alien terrain, not sure what you’ll face along the way.

This infographic totally gets it. Created by the folks at FreshBooks, it captures the trials and tribulations that freelancers face after taking the leap. From what you need to prepare to promoting yourself on social media and handling your own accounting, it offers a pretty comprehensive look at what it means to be a freelancer.


I personally swear by the notes I jot down in my phone. (Was there even life before Evernote?) The corporate temptresses are no joke and Retirement Neverland can feel like an illusion, but it’s important to keep trekking and stay hopeful. 🙂


New Year, New Start: Optimize, Not Maximize

As you know last year I decided to take the leap and become a full-time freelancer. It was a major decision for me, and a very difficult one at that. I was offered a high-paying contract gig, one that paid nearly six figures. I know. It was the most money I’ve ever been offered for a job. As a writer and proofreader who has only worked in non-profit and publishing, I never thought I would be ever be offered that much money for a gig. I waffled over it like crazy, and didn’t sleep for days.

And although adjusting hasn’t been life on Easy Street, I know that it was the right choice for me. I have decided to commit to at least a year to freelancing, until the end of this October. Ideally I would love to live this way for as long as possible, but I figure a year would help me get a feel for the ebb and flow of this sort of work and learn to roll with the punches.

As we kick off a new year, I’ve been thinking a lot about how I want to spend the next year as a freelancer. The toughest thing is achieving a balance between all the things I want to work on, I find that my passion projects and freelance business are oftentimes at odds with one another. Instead of trying to maximize my work, I want to try to optimize.

What does this mean, exactly? Maximizing and optimizing are terms used in the investing and business world. Maximizing means to gain as much as possible, no matter what the cost. Optimizing, on the other hand, is finding an approach with the most cost-effective or highest achievable outcome given the constraints. Okay, so I may be tweaking the meaning slightly, but to me this means figuring out what’s the important to me, what gives me the most joy, and putting more time and resources into the things that matter more.

The big questions for me are:

How much freelance should I take on? How much money should I try to make?
How much time should I devote to passion projects?
What can I do to best support these priorities?

Income-wise, December was an amazing month for me. I made more than twice as much as I did working my old full-time job. But I worked like crazy and had little time for anything else. My family and I took some weekend trips over the holidays and I remember getting up at 4 am to work. I worked in the lobby of a hotel while my family was out and about. It sucked. And I am going to be  honest: I don’t ever want to work in that fashion again. So instead of taking on as many clients as possible, working crazy hours and making as much money as possible, moving forward I can be a little more picky with clients, work less and make enough to survive. I can then make more time for my personal projects, which are my fiction (I am working on a graphic novel and collection of short stories), and this blog.

While trying to grow and develop my freelance business, I will continue to carve out some time each morning to work on my projects. I have not been successful at this, to say the least. My goal is to start super small. I will start with 10 minutes every morning and see how that goes. Of course, you can’t get too much done in 10 minutes, but as my good friend Alan Steinborn of Real Money has told me, consistency is key. You must do it every day, no matter how long.

To support my goals, I am going to commit to working my own projects every day, no matter the looming deadlines. Even if it’s just for 10 minutes. I am going to be careful with taking on more freelance work. If I find myself having any downtime or a slower period, I will be sure to have a game plan in place to take advantage of this time.

So I ask you: What’s important to you? What steps will you take to optimize your life? What will you do to support these goals?