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.

The Conversation That Helped Me Turn Down a $96,000 a Year Job

Illustration by Viet Vu

When I was in between jobs a few years ago, I was scurrying around like a crazed rat that had lost its way in a maze. The week after I had been let go from a one-year contract job as a personal finance writer for an insurance company, I met with a bunch of different recruiters at creative job agencies around town.

And when I landed a job interview to basically proofread web articles for an investment firm downtown, I didn’t really know how I felt about it. The contract job (read: no benefits) would last anywhere from 6 to 18 months. The rate was definitely right: $44 and hour, plus $2 an hour for “parking fees.” So I did the math, and a full-time, $46 an hour gig roughly equaled $96,000 a year. Umm..certainly nothing to balk at.

I landed an interview, and an acquaintance who currently worked there and was kind enough to give me great pointers. Right after the interview the recruiter gave me a call to ask how it went.

“Good, I think.”
She asked, “If they offered you a job, would you take it?”
I replied, “I don’t know.”
I could tell she was disappointed in my response, but it was an honest answer.

At that point, I had landed a lot of great job leads for personal finance publications. Writing about money was something I had always wanted to do. I was in talks with about four different places, and in the “courtship phase,” so to speak. So again, nothing was for sure.

About an hour after the interview, I received a call from the recruiter that they wanted to offer me the gig. Of course, she needed an answer as soon as possible. Naturally, I equaled dollar signs to her. I asked if I could have the weekend to think about it.

I got zero sleep for practically two days. I asked my good friends what they thought. Some of them couldn’t imagine why I wouldn’t take it. “Wow, that’s a lot of money.” “You could save up and then take a year off if you really wanted to.” Another good friend asked had some really great advice. She asked me what I was scared of doing the most, and to run with that. My friends were well-meaning, but their words of advice were started to feel like a bunch of bees buzzing around my head. I knew the decision had to ultimately come from me.

Here’s the thing: I initially accepted the offer. It seemed like the practical thing to do. And wouldn’t you be crazy for turning down that sort of money?

That weekend, I met up with my friend Tricia. Her brother from Canada was in town, and we met up her Tricia’s husband Andy for dinner in Echo Park. Andrew was also freelancing at the time, and interested in what I was up to.

I told him about the job I was offered. Telling someone how much I was offered felt insane. Andy asked me a bunch of sound, practical questions that really shed some insight. By the end of our convo, I had changed my mind about accepting the contract job. I didn’t want to take it anymore.

Here’s what he asked:

How many clients do you have now?
I had three clients, and after FinCon, was in the “courtship phase” with about 4 clients at the time. But nothing was set in stone, which was pretty nerve wracking.

How long can you live off your savings?
I had a decent amount saved. Since I am such a frugal person and have been saving my beans since my first job after college, I could comfortably live off my savings for about a year. If I was going to barebones about it, I had enough to get by for about a year and a half.

This played a major part in my decision-making. If I had looming debt and no savings, I would’ve taken the job in a heartbeat. But because I had a cushion of savings, I could weather any potential storms.

How much are you making a month freelancing?
Income-wise, I had a great month the month prior. One of my clients requested more content from me, and I netted $6,000 from just one of my existing clients.

I would be making about $8,000 a month with the contract gig. The $2,000 difference didn’t seem that large. And I felt that if I really tried, I could make $8,000 in a single month on my own. No having to drop buckets of money toward

If you’re thinking about being a full-time freelancer, I suggest raking in at least half of what you’re making at your day job. You definitely need some anchor clients when you’re starting out. Plus, it takes a while to figure out your “productivity flow,” how much time it takes to complete certain assignments, and the scope of projects.

How excited are you about the actual job itself?
I felt confident in my abilities to do the job, but as far as day-in, day-out satisfaction and growth, there was nothing. Besides learning about that particular company’s organizational structure, and perhaps a bit more about investing, I knew I had a cap on learning—and earning potential. Although I was scared to, my gut was telling me that I would just be delaying what I really wanted to be doing.

As a freelancer, I oftentimes take on assignments and work with clients because there’s a chance to grow or learn in some way. Maybe I’m working with a top-notch editor that could really expand my skillset, and push me to be a better writer. Or for publication that is open to hearing a fresh spin or or some of my weird ideas (I have many of those, by the way).

And because I write every day, anywhere from 3-6 hours during the workweek, I’m a stronger—and more prolific—writer.

What do you want to do ultimately?
I’ve long been curious about freelancing. I know that a lot of people turn to freelancing because their hours are reduced at their jobs, or they get laid off. But this is something I had long fantasized about.

Andy suggested I do freelance. He said that I could be proofreading articles 40 hours a week for the next year, or lay the groundwork for my freelance writing business. And you know what? He was 100 percent right.
While I didn’t net six figures in my first year as a full-time freelancer, I didn’t starve, either. I actually netted more money in my first 10 months than what I was making at my old day job. And I worked less hours, which was pretty awesome. Plus I was able to hang out with my friends and family, and travel more. And there’s zero doubt in my mind that I made the right decision.

We respond to numbers. You see the words “six-figure salary” and the first words that pop in your head are like “whoa,” or “I want that.” But of course, you don’t know how many hours someone may put on the job to rake in that much dough, or if they’re running their own business, how much they had to put in to get that sort of return. (Case in point: Stefanie O’Connell’s business expenses for generating a six-figure income in 2016. I admire Stefanie for your savvy business prowess and transparency to her readers. Yeoch).

But there’s a lot that goes into making a big decision that goes beyond your salary and benefits (which are obviously both very important things to factor in). For me, having some clients in place, an idea of what you want to focus on, and having an emergency fund, are key.

If you’re seriously considering taking the leap into full-time freelancing, what are you biggest qualms about doing so?

Freelancing Out of Necessity? Here’s Your Ultimate Game Plan

Illustration by Viet Vu

Freelancing can be pretty freakin’ awesome. But it can also suck hard, too. Having just hit my 15-month mark as full-time freelancer, I’ve realized how crucial it is to keep things together—and how easily things can fall apart. Freelancing is a funky hybrid of sorts. One one hand, you have have the freedom and flexibility to choose your clients (ideally), to create a schedule that jives best with your productivity style, and work pretty much anywhere there’s reliable wi-fi. On the other hand, you need to stay super organized, and bear the responsibility of footing the bill for your own health insurance and retirement. Oh, and then there is the anxiety and stress that comes with income that fluctuates month to month.

Freelancing is oftentimes depicted as a choice, something A-types and hustlers do on their own accord. But what if you were given a gentle nudge—or were straight-up forced—into freelancing? In 2015, while I had long wanted to try out the freelance life for myself, I took a baby step from leaving my full-time job with benefits at a job I liked and accepted a one-year contract position. However, about two months into it I was given the pink slip. They were overstaffed and so had to let me go. Initially I was in shock, but two days later I was on the plane to FinCon, a conference for money nerds and personal finance content creators. And lo and behold, I landed a bunch of leads at their Freelancer’s Marketplace.

My leads, along with a robust f*ck-off fund and a super helpful talk I had with my friend Andrew prompted me to not accept a near 6-figure contract position at an investment firm. That was almost half of what I was used to raking in a year. The job would’ve been fine, except that it was putting off what I really wanted to do—freelance! It was incredibly scary, and to be honest, still is. But I found that it has all been worth it. I was able to make more in the first 10 months of the year than I had at my old full-time job.  

But what if you’re not as prepared? If you’re freelancing out of necessity, either because you were laid off or had your hours drastically reduced, how can you best manage? Here are some pointers on how you can make up for that lost income, and land “bridge gigs” that could potentially lead to your next job?

Tap into overlooked pockets of savings
Yes, the 3-6 month emergency fund is something we could all use. But seriously, most of us barely have a couple of hundred bucks to our name. I highly recommend couch scrounging, breaking piggy banks, and trying to find little pockets where money might be. This includes bank accounts you had opened long ago with a few dollars in it.

Moving forward, seriously work on boosting your savings, either by starting off with a few hundred dollars, then a buffer fund that can cover a month’s worth of your basic expenses. I absolutely love Digit, and since I signed up this past March, have saved nearly $3,000. How Digit works is that it uses an algorithm to automatically save money for you. I am super lazy, so love how effortless it is. You can use that money to put toward your emergency fund.

Boost your earnings by doing what’s easiest
I’m all about doing what’s easiest. I had been working in publishing and communications for about 9 years when I was nudged into freelance, I was moonlighting for about 6 years, writing personal finance articles, copyediting art magazines, children’s books, and writing copy for websites. I also was petsitting and test proctoring at a local university. So I reached out to my network and got whatever gigs were easiest for me at time.

And while I don’t really do as much copyediting as I used to, I still work at my old job at a publisher about 6 months of the year for about 10-15 hours a week, and I consider them an anchor client. And guess what? I still petsit and test proctor on occasion. Those are both gigs where I get paid to sit on my bum and work on my freelance.

Get your feelers out there, and take on whatever side hustles are easiest for you. If you love to drive and have a reliable ride, sign up to be a rideshare driver, or if you are an ace at repairing your bike, then offering fix-up workshops. Sell your junk on sites like eBay or decluttr, get paid on sites such as Swagbucks, or take advantage of referral codes and cashback offers.

The key is to make money quickly so you don’t have to  needlessly tap into your credit cards. You really don’t want to hurt your credit, so don’t spend more than you need to. Once you get your bearings, you can spend more time raking in cash in ways you really want to.

Create different streams of income
For 27-year-old Tyler Philbrook, a personal finance blogger who runs I am the Future Me, he looked toward several side hustles when his job as a pharmacy tech was cut from 36-40 hours to 28 hours a week. While he had already started side hustling as a freelance writer, he also began to drive for Lyft and Uber, and made money on Amazon through their Fulfillment by Amazon program. He’s currently making $2,000 a month from Amazon, $200 a month freelance writing, and a few hundred a month as a rideshare driver. What’s amazing is he is making more money selling on Amazon than at his day job.

Ideally, you should have been working on your different streams of income by side hustling well before you have to turn to freelancing, Philbrook recommends. “If that’s not possible, don’t freak out. It’s not the end of the world; it  just will be slightly more difficult at first,” says Philbrook. 

Keep an open mind
Okay, so maybe you’re at Point A and what you ultimately want to do is at Point Z. I’ve learned that piecemealing your way to what you want to do is a great approach. So in other words, go from Point A to B, and take it from there. It ultimately took me 10 years and hopefully it won’t take you that long, but by figuring out what I enjoyed the most at each job, then trying to do more of it at my next job, all while building up my skills in my off time. I will get more into detail about this in a later post, but be open to opportunities, taking on new skills, and most important, grow where you’re planted.

Ease up on yourself
This ish takes time. Even though I had started side hustling and building out my client base long before I took the leap to freelancing full-time, I didn’t start really getting into the swing of things and writing for some of the new clients 1-2 months later. And depending on where you’re at, it could take longer. So be patient with yourself, and keep at it.

While you may be freelancing due to less-than-ideal circumstances, by pulling your skills and resources together, you can make this freelance thing work. While it may require more work and grit than a day job, it can be far more rewarding. And you may learn that you’re actually cut out for self-employment after all.

Disclosure: I do get some monies if you sign up via my link for Digit, so if want to check it out and support the blog, I’d be much obliged.

How Getting a Custom Freelancer Contract Can Help you Save or Earn Money


Freelancers Contract

Illustration by Viet Vu

By Tristan Blaine, Esq.

Contracts. The word stirs up such excitement, doesn’t it? But seriously, contracts can actually be sort of fun when you think about all the possible uses for them and you realize how empowering it can be to use them effectively. But not only is it empowering, a contract can help you save or earn serious money. How? Well, to start with, it can help prevent a client from skipping out on the bill, and save on the time and money that may be necessary to track down payment.

To be clear, this post is not meant to be legal advice, and some or all of it may not apply to your situation. I don’t recommend drafting your own contracts. The best way to use this information is to take it to a small business lawyer and discuss how it relates to your freelancing business. Try to find a lawyer who has reasonable pricing and flat fees (they do exist, and I’m one of them!). It probably shouldn’t cost more than $500, unless you have a particularly complex situation. If that still sounds like a lot of money, keep in mind that it’s likely a tax deductible business expense. And having a great contract could easily help you save or earn thousands of dollars, much more than what you would be spending for legal help.

Also note that the client may not necessarily agree to any of these provisions, in which case you should decide whether to drop the provisions or drop the client.

All that said, here are 6 important contract provisions you should know about to save and earn more cash.

1. Detailed description of scope of work
This one is pretty basic, but is often overlooked. Describing in detailed and specific terms what you will do for the client makes it clear that anything other than what’s in the scope of work will cost the client more money. So if the client tries to say they thought your flat rate included, for example, several rounds of revision until the client feels satisfied, you can point to the scope of work that (hopefully) says your price includes only one revision. Often the client will then concede and pay you for the extra work.

2. Intellectual property provisions
Make sure you are up to speed on what intellectual property rights you have in your work (a topic for another post; or find a good intellectual property lawyer), and that you clearly state in your contract what rights you are and are not giving to the client. Generally, if the client wants more (or all) of your rights, they should pay you more.

3. Clear payment terms
Another seemingly obvious one, but have you included exactly how and when payment is to be made? If not, the check could get “lost in the mail.”

4. Late fees
Part of the payment terms, but this one deserves its own category. Late fees are a great way to incentivize clients to pay on time, every time.

5. Limitation of liability
You may not be thinking about what happens if your client sues you, but unfortunately it’s a possibility. But did you know you can limit the amount of money the client can sue you for to only the amount they paid you? Yep, just make sure you have one of these nice little provisions, and you could save some serious cash.

6. Liquidated damages
Sounds complicated, but it’s not really. It’s simply a way to make it easier to enforce the contract in case your client violates certain provisions. You see, sometimes it’s hard for a court to determine how much one person should pay the other for not following the contract. For example, if the client uses your intellectual property but doesn’t credit you as you had agreed, how much is that worth? Maybe it’s your lost profits, but it’s often hard to figure out how much profit you would have made had they credited you properly.

To deal with this you can simply stipulate “liquidated damages” of a reasonable dollar amount or percentage of your fee, and this is the amount that the client would likely have to pay you for breaching certain parts of the contract.

Fun stuff, right? Let me know if you have any questions or comments on any of this!

Tristan Blaine is a “freelance lawyer for freelancers,” which is a fun way of saying that he has his own law practice and works primarily with freelancers and small businesses. He also created a website, Law Soup, for everyone to get some quick answers on a variety of legal topics.

My Personal Road to Financial Wellness: What Freelancing Is Really All About

The following blog post is part of The Road to Financial Wellness blog tour. The Road to Financial Wellness is a three-month, grassroots campaign promoting financial empowerment on a national level and encourages people to pursue their dream lifestyle. Find out more about local events near you.

When I took the plunge into freelancing full-time last fall, approaching it as a yearlong experiment, I really didn’t know what I was in for. And although I had been hard at work building a solid relationship with money for as long as I could remember, learning to deal with money matters when self-employed is a completely different beast.

Sure, there is learning to work with income that ebbs and flows, budgeting for self-employment tax and your own healthcare, and creating your own routine and structure, which are all part of the rite of initiation that millions of the self-employed have gone through.

And as I am two-thirds into my experiment freelancing full-time, I’ve been spending a lot of time thinking about why I decided to try out freelancing in the first place. While I’ve never been big on building wealth, I’ve been deeply interested in being free to create a life that is more in step with my values.

Here are a few insights I’ve gained on how freelancing relates to financial wellness:

It’s Changed My Relationship With Money
Back when I was working a day job, you agree to working a certain number of hours for a set amount of pay. And you do whatever it takes to get the job done. I remember at one salaried job I worked diligently and was crazy about timing myself so that I was super productive. But how did I get rewarded? Did I receive a raise, or maybe got to go home early? Nope! I was just given more stuff dumped on my plate!

When you freelance you get paid for the value you bring, not the time you put in. Conversely, you can see the clear exchange between your time and money. Oftentimes I consider whether it’s more valuable to me to get paid X amount of money to write an article or keep that time to myself, whether to go on a hike, spend time with my friends, work on my fiction, or just lollygag.

Because I am pretty careful with my money, I feel like I have the freedom to make that decision instead of taking every job that comes my way. When I first started I felt compelled to take on every writing assignment that came my way, but soon realized if my heart wasn’t in it, I wouldn’t do my best work.

I Can Be There for Others
Now that I have more flexibility with my schedule, I’ve been able to be more available for my friends and family. I sometimes head over to my 81-year-old friend Marie’s house to get some work done in the middle of the day, and now that my mom is about to enter semi-retirement, I can carve out time during the week to help her with her transition.

I used to worry about having to take time off if one of my parents fell ill and needed me to take care of them. My work life and personal life is better integrated. With freelance I can ideally still work while being there for others. I’ve taken on the approach of being a minimalist freelancer, meaning I do my best to do enough to maintain financial wellness while having time for other aspects of my life. It’s a daily struggle, and I’m still working at attaining that.

I’ve Stopped Hiding Behind the Guise of Being Busy
For the longest time I didn’t have much career focus, and I didn’t think I could ever combine two of the things I loved the most: writing and helping others have better relationships with money. Besides holding a day job, I’ve always felt pressed for time to work on my passion projects. I felt as if my social life got in the way of focusing on my creative endeavors.  So I would make the excuse of being too busy when I felt like being a hermit.

And when I started getting paid to write about personal finance a few years ago, it was pretty amazing. I almost couldn’t believe my luck. And when I am not trying to hit deadlines,  I am able to make time to work on my passion projects.

But I have come to realize that for a long time I had been hiding behind my aspirations. I need people in my life, and I want to be better at maintaining relationships.

I am someone who values people but also needs a lot of time by herself to think, wander and create. And striking this balance can be a complex project. Being self-employed has enabled me to be more honest with myself, that I need people yet also need a lot of alone time.

Working hard at being financially healthy has given me the freedom to take the leap to freelancing fulltime. And while I create a new budget and structure to help me stay financially fit, I am also realizing how freelancing is a sort of portal to learn about myself and live in accordance with my values.

Illustration by Viet Vu


On Coming to a Zen-Like Approach to Freelancing

As I’m nearing the end of my 8th month as a full-time freelancer, it’s hard to believe I’m two-thirds in to my yearlong experiment. Life has certainly been a little crazy, and I’ve slowly come to realize how much I’ve learned in the last eight months. I’ve learned a lot about managing my time and money, landing and working with different kinds of clients, and dealing with self-motivation—and the occasional lack of it.

I’ve been practicing Zen Buddhism under the teachings of Thich Nhat Hanh for about six years now, and while I’ve gone off track more times than I would like to admit, being a practioner has helped me deal better with my anxiety and be a more peaceful, compassionate person. Plus I’ve met some great people.

As I am starting to formulate my own approach to the freelance life,  I see just how much freelancing that ties in with my Zen Buddhist practice. I’ve mused a little bit as to what it means to be a minimalist freelancer, and here are a few ideas how you can have a more mindful, Zen-like, mindful approach to your work.

While not all freelancing professions are created equal, and depending on what line of work you are in, you can build and maintain a roster of clients and have relatively stable work. However, as I’ve discussed with my mastermind group buddy and freelance mentor Alan, continuity is not something you can rely on as a freelancer. Granted, life is filled with uncertainty, but there is a greater margin for stuff going up—and down—when you freelance. You may gain a boatload of clients or lose some, and your money ebbs and flows, too.

You can love the work that you do but it’s also important not to connect your feelings of worth and well-being to it. This is far easier said than done, and can be applied to any job, but with freelance you could have a one-off assignment or have something end earlier than you would like.

Focusing on the here and now
I struggle with anxiety about freelancing on a daily basis. I am someone who craves stability, and I know that if I’m not okay with living with a little bit of variance and uncertainty, then I probably shouldn’t freelance. What’s funny is that I’ve been doing really well. I enjoy all the writing that I do, I’ve been doing well money-wise, and I’m creating a structure to carve in time to work on my two main passion projects—working on a short stories collection and this blog. And now that I have a much more manageable schedule, I have more time to focus on my passion projects. I really can’t complain. So why do I feel so anxious all the time? I guess I get anxious no matter what the circumstances.

I made a deal with myself. As long as make my emergency fund a savings priority and have a backup plan in place when I have a lull in work or the going gets tough, that’s the best I can do.

Zen Mind, Beginner’s Mind
I don’t always succeed at this, but I try to treat every assignment I do as if I’m writing for the first time. This keeps me excited about the work and it helps me do my best. When time permits, I savor the work. It’s helped me enjoy what I do immensely. This can be challenging to do when you have a lot of deadlines and write about the same topics. But trying to approach something with a new set of eyes really helps keep the work fresh.

Equanimity essentially means giving everything equal weight. This might be the hardest thing to do, because wouldn’t you naturally spend the most time and energy on the stuff you enjoy the most, or that pays the most money? Isn’t that the smart way to work? By giving everything equal importance, you’ll be able to savor the work more and in turn produce high-quality stuff.

Not expecting anything special
The last few months of last year were insane. I worked pretty much non-stop and made more money in a month than I ever imagined making. However, I was so stressed that I vowed never to work that way again. I oftentimes think about what it means to be a “successful” freelancer. Does it mean working for big league publications and high-paying clients? Or landing an assignment with a rate that’s four figures? What data is useful in figuring out this “success”?

Of course, the definition of success depends on the individual. But I see a lot of people writing e-books and selling e-courses on how to kick ass at freelancing. I think sometimes it can be an illusion. Of course it requires a lot of skill, focus, and discipline. You really have to be a self-starter and comfortable at hustling and networking. This isn’t anything new.

But some of your success is left up to chance. Sometimes you work in a niche that’s hot. Or you entered at just the right time. I’ve made a lot of money some months, and not as much in others. I landed my first four-figure assignment and it was pretty awesome. But I’ve also experienced my first lull. Lulls are awesome too, because I have more time to work on my other projects. Are these “meaningful” events? Signs that I’m on the “right track?” I’m not really sure, to be honest. I do know that I’m happier knowing not to expect anything “special,” as if something huge to about to happen.

Practicing gratitude
I try to be grateful for every opportunity that comes my way, and to do my best work. The joy exists in the work itself. There isn’t a day that goes by that I’m not grateful for getting the opportunity to test out the waters. Every day is a little bit different. And that is pretty awesome in itself.

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? 


How to Make Friends with Risk (Even When Fear Is Still Hanging Around)

I have never been much of a risk taker, especially when it comes to my money. I mourn every nickle lost playing penny slots on family trips to the Indian casino, and my mind on autopilot naturally does a cost-benefit analysis of purchasing a pound of bananas versus a pound of pears (a pound of pears wins every time, by the way). What can I say? I’m just “grandma” like that.

And when I talk about risk it’s not just the monetary sort. This risk can be a big move, or a job change, or trying something completely new. So when an opportunity presents itself, even though there’s a big part of me that knows there is much to gain by taking a chance, it’s super tough. I decided to leave my steady, 9-5 job with benefits, a job I enjoyed, to take on a contract job that was more along the lines of my long-term goals of being a personal finance professional. It was a big decision for me, and it felt like I was taking a risk. It’s that part of you that is going from what you’re comfortable with, what you know, to a bottom-of-your-stomach feeling of facing the unknown. Here are a few tips on making friends with risk:

1.  Remember what you have to gain.
When fear takes over your instincts kick in and you want to cower underneath a rock, it’s difficult to have perspective on why you made the decision in the first place. By reminding yourself what you have to gain, you’ll be able to stick to your decision and work through any rough patches.

2. Find your anchor points.

My former boss introduced this concept to me to explain his foray into starting his own business. Anchor points can be what you perceive as sound and steady. If you’re foraying into freelancing full-time, your anchor points could be a couple of steady clients you can depend on for income. If you’re moving to a big city, it could be a volunteer group you want to check out or maybe fun hiking trails in the area. These anchor points will help build a foundation (and maintain your sanity) as you make your big move.

3. Think: It’s not a leap, it’s a transition. 

If you’re like me you might feel momentarily paralyzed when facing fear. Think of your decision as a series of smaller steps rather than leaping into an abyss of the unknown (although it may feel that way). And try your best not to idealize the past and replicate former conditions. For instance, if you are moving to a new place, you might miss your awesome friends, favorite pizza place, that sort of thing. In your new town you may want to have the same friends and hangouts of course, but the pieces may not come together immediately. The thing is that you’ll be working with different puzzle pieces, so expect something different. It may appear imperfect at first, but the unfamiliar can be an exciting thing!

4. Have a backup plan.
Isn’t that a slap in the face to blissful optimism? It certainly is. Being pragmatic will help you get back on your feet in case things don’t work out. Sit down and figure out some options for a Plan B, Plan C, and so forth. Rule of thumb: it never hurts to have an emergency savings and to build out your support network. Also giving yourself a time frame also helps. Do you plan on staying in the new city or work on starting your own business for 1 year, or maybe 2?

Life is filled with uncertainty, and to borrow a cliche, change is the only thing you can bank on. So why not embrace a change that can help you grow in the long run?

Skimp or Splurge? Starting Your Own Brewery

In the last Skimp and Splurge story we featured Studio Mucci and their Etsy Store. In this installment, we’ll cover running your own brewery or cider mill. You haven’t had hard cider until you’ve had Downeast Cider—or so I’ve heard. *sad face* Downeast Cider is run by 20-something founders Matt Brockman, Ross Brockman, and Tyler Mosher. Their passion for high-quality hard cider began in 2011 when Ross and Tyler were just college seniors.

As New England’s newest and fastest-growing hard cider company, they’ve managed to stay true to their original, homespun process of using all-natural ingredients to make freshly pressed hard cider. As a hard cider lover, I’m a little jealous that I don’t live in Boston to enjoy their cider. Hoping it comes to the West Coast one of these days!

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In the past few years, Downeast Cider increased their input threefold and made the Forbes 30 Under 30 in the Food and Wine category. They also do cool things like host a prom at their headquarters and are co-sponsoring a music festival. Good times! Here are some tips from Matt, Ross, and Tyler on what to skimp or splurge on when it comes to running your own business:

Office furniture: Skimp
All of our furniture either came from the island of misfit furniture from a back-alley used furniture store or from the dump. It’s actually a recycling company that will get truckloads of old furniture from businesses that are no longer businesses, and they drop it off on our loading dock with a backhoe.

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Useless Merch: Skimp
Which is most merch. You don’t need T-shirts and hats and golf balls and all that garbage. First, if it’s not high quality or useful, most of it will actually end up in the garbage. If you’re a tiny B2B software company that nobody has ever heard of (or pretty much any small company for that matter), spending $500 on T-shirts is an ego stroke and a waste of money.

Lawyer: Splurge
Much like insurance, you can easily justify skimping on your lawyer when setting up your corporate docs. If things go sour, these documents, such as your operating agreement and articles of organization, are the map for solving issues. If your map sucks, it’s useless and you’ll have to start over again. If you’re gonna skimp, write something on a napkin. If you’re going to spend any money at all, make sure it’s quality work. Mediocre legal work is a complete waste of money.

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Customer Service: Splurge
Especially if you’re an entrepreneurial amateur. Over-the-top customer service is another insurance possibility. If you make a mistake and your customer doesn’t think you give a shit, you can kiss them goodbye.

Equipment: Skimp
At least in our business, you can get a lot of what you need for much less than full price if you can find it used.  New is oftentimes no better than used when you are talking about stainless steel equipment that is built to last a lifetime with proper care.

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How I Survived My 20s—And How You Can, Too

Your 20s are tough. You’re trying to figure out what you want to do, who you want to be, all while trying to eke out an existence for yourself. My 20s was a period of couch-change scrounging, bargain hunting, bouts of existential crisis, and requisite floundering.

Now that I’m in my early 30s I can tell you that my life is more of the same, except that I do feel a lot happier, focused, and more confident. And it’s not that I’m super successful or have achieved amazing things. (That whole you have to achieve X and Y before you hit 30 is a myth, my friend.) It’s more about taking comfort in the fact that I am resourceful enough to get through a rough patch.  I don’t have it all figured out, and probably never will, and I think that’s a good thing. It’s cool to keep learning, growing, and changing and at times laugh at your former self.

I didn’t make very much money during my 20s. Like a lot of people with creative pursuits that don’t necessarily translate to making big-time bucks, I struggle with wanting to make more money and having enough time to work on my passion projects. One thing I did do that worked out for me was that through self-education I learned a thing or two about managing my finances. Here are some things I did money-wise that helped me get through:

I moved back home.
Yea, I know. After graduating with a degree in Anthropology, my career aspirations were a little murky. All I knew was that I wanted to write in some capacity and get some real-life work experience. So I moved back home for about a year and a half, worked at a coffee shop, and interned at a couple magazines. It kind of sucked at times, but my living expenses were super low. And after I landed my first full time gig as an editorial assistant at an astrology publishing place, I waited six months until I had saved about 5k to move into my first apartment. It was a tiny single apartment on the Westside. But for $675/month in 2006 (really unheard of these days in L.A.), it was a space all my own so I couldn’t really complain.

Takeaway: Moving home can suck, but sometimes it’s a means to an end. It’s not a reason to be a professional slacker. Just make sure you have a good reason for doing so and a game plan for moving out in tact.

I paid down debt
I was fortunate to have received a fair amount of financial aid, grants, and scholarships so my student loan debt was only at about 10k. My interest rate was pretty low (about 3% or so) and I slow-boated it. As I started making more money, I tried to pay down as much as I could more toward the principal and could pay it off sooner. I made it a priority to pay it off. If you just graduated or are about to, look into your student loan repayment options well ahead of time (I’d say at least 6 months in advance) to see what plans you qualify for.

Takeaway: Do not ignore your debt. It is not going anywhere unless you do something about it. Even if you are in a sticky situation, look into deferment or paying what you can until you are in a better place to pay it off. Make it a priority. You really don’t want the debt hanging over your head to get in the way of your goals.

I invested in myself.
I took evening classes at a nearby community college and through online university extension programs in graphic design, fiction writing, and completed a certification in copy editing. While this wasn’t as fancy as going to grad school or getting an MBA, the certification in copy editing has paid for itself many times over. I was able to get freelance work on novels and magazines. Not only was it a lot of fun, but it felt nice to generate some extra cash. My work paid for some of the less expensive courses and half of the ones at UCLA Extension because learning these skills would help me contribute more to the job.

Takeaway: Invest in yourself by taking classes that will help you in your career and also with your creative pursuits. Ask your employer if they offer compensation for continuing education. Even partial compensation would be rad. There’s also a wealth of online courses these days, i.e., I’ve been using Lynda as long as I finished college, and have used it to learn about everything from InDesign, Photoshop, Excel. The best part about Lynda is that you can just watch a short video that gives you instruction on exactly what you’re trying to learn, and apply that skill right away. I know that Lynda offers a 10-day free trial, and you can literally spend days learning a ton from their video tutorials.

I learned how to budget.
I am a little bit of a “budgeting fanatic or a “budgeting whore” rather. I usually am trying out several apps at once.  Whenever there’s a new method or app for personal budget, I am one of the first to jump on the bandwagon and check it out. I started getting into budgeting during college and used a simple system I created in an Excel sheet. Was it tedious? Sure. But it helped me figure out where my expenses were and what areas I went a little overboard in. And eventually I developed my own budgeting style. These days there are plenty of budgeting apps (i.e., Digit, Mint, Learnvest, Level Money) that makes it much simpler. I can wag my finger like a little old lady at you youngins and say how much harder I had it than you.
Takeaway: The sooner you learn how to budget, the better. It’s not about getting it perfect, it’s about starting out and being okay at it.

I side hustled.
I test proctored, did some catsitting, and some freelance editing on the side. Any extra money I earned was “get away” money, money I saved for something big like a vacation or new computer.
Takeaway: Finding ways to make extra revenue is a great way to pay down debt, keep yourself financially afloat, or “get ahead” on your other goals. I’m a little envious of the youth of today, because there are so many ways to side hustle.

I played the frugality game.
I became a master at saving money whenever I could. When I was 24 and signed my first lease,  I felt like a total grownup. But I was also terrified. Terrified that something would happen to my job, I wouldn’t make ends meet, and have to break my lease. So I learned to be really good at being frugal. Remember there’s a huge difference between being stingy and being frugal. Being stingy is trying to get everything at the lowest price and living a somewhat miserable existence. Frugality, on the other hand, is about being resourceful and figuring what the value of certain things are to you. I cut back on everything from on groceries, eating out, clothes shopping, going out. If you turn it into a game and have your sights on the big picture,  it’s kind of enjoyable.
Takeaway: Try to save where you can. The three biggest expenses you have are shelter, food, and transportation. Cutting back in any of these three areas is a great place to start.

I did not upgrade my lifestyle.
Whenever I got a promotion, raise, or jumped jobs that upped my income, I didn’t make drastic changes to my lifestyle. I drove the same car, I lived in the same place, and kept the same lame-o friends (just kidding, I love my buddies!) I lived like a pseudo-urban monk and due to living in a super small space, kept my possessions to a minimum. There were moments when I thought I would turn out like the 80-year-old Korean woman who lived in an identical studio apartment across the way for 40 years, but I knew I had to focus on some of my other goals like start saving for retirement and pay down my debt before I could move into a larger space.
Takeaway: By maintaining your same lifestyle despite having more money, you’ll be able to put that money toward other things while having the freedom that if something happened, you won’t get into a pickle. We can talk about how to know it’s the right time to upgrade to a bigger place, buy a nicer car at a later day.

Being in your 20s is exciting yet also can be nerve-wracking. It’s tough to make it work, whether you’re trying to start your own business, carve out a career path, or balance your artistic passions with making a living. But with a little bit of balance, self-knowledge, and discipline, you’ll make it through.

How are you making it through your 20s?