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Take a Class with Me in 2016

I’m pleased to announce that I am now an instructor at, and I have two classes coming up:

Pitch Like a Honey Badger


The Nuts and Bolts of the Freelancing Lifestyle.

Pitch Like a Honey Badger” is intended for freelancers who want to improve their pitching skills and, by extension, their rate of acceptance and number of assignments. The class starts January 20 and is asynchronous, meaning there’s no set meeting time; you can work through it at your own pace.

In “The Nuts & Bolts of the Freelancing Lifestyle,” I’ll be teaching something almost no other writing course teaches: the finances of freelance writing. This course is designed to help you define what financial success looks like for you as a freelancer and to assist you with developing a concrete, practical plan for achieving it. It starts March 9 and is also asynchronous.

If you’ve ever worked with me before, you know that I’m very hands-on with students and colleagues, offering honest, useful feedback and support that’s rooted in the values of transparency and giving.

I hope you’ll consider registering for one (or both!) of these classes. If you have any questions, please feel free to contact me directly at writingjulie [AT] gmail [dot] com.


How to Take a Work Trip across Three Countries with Your Three Kids–and No Partner–without Losing Your Mind

I’d been planning a Cuba trip for a while–I had work to do there and in-laws to visit, and I hadn’t been since early 2013–but for one reason or another, dates just weren’t lining up. Finally, the calendar cleared and I secured multiple assignments that would help pay for the trip, so it was game on– time to book flights.

Except I wasn’t traveling alone.

Four passengers = four passports and four visas. (Photo: @collazoprojects)

Four passengers = four passports and four visas. (Photo: @collazoprojects)

My oldest daughter, who would turn six during our trip, had been to Cuba twice, but the youngest, ages 2 and 1, hadn’t yet met their abuela and tias and tio. With a mother-in-law who’s in her 90s, it’s not as if I have the luxury of putting off a visit with the grands. Yes, I needed to work–covering everything from the papal visit to restoration projects and new entrepreneurial ventures–but I also needed to make sure my kids and their father’s side of the family were getting some quality time together.

Only my husband wasn’t going to be a part of the equation.

A complicated immigration status would keep him at home in New York while I sat on airplanes and hauled two suitcases and as many strollers through three airports in three different countries with three children, starting out at 4 AM in New York City and ending up 15 hours later in Havana.

“Are all these kids yours? Are you a sadist or something?” That’s what the US Immigration officer asked when I came back to the US 10 days after I’d left. I just gave him the evil eye. My kids are great travelers.

My two-year old looks out the window on our approach to Mexico City, our layover on the way to and from Havana. (Photo: @collazoprojects)

My two-year old looks out the window on our approach to Mexico City, our layover on the way to and from Havana. (Photo: @collazoprojects)

That being said, enough people asked how I managed to make the trip alone that I thought it might be worth sharing my clutch tips about how to travel alone with three kids on a work trip without losing your marbles.

1. Pack light.
Yes, you’re traveling with kids, but trust me: kids don’t need nearly as much stuff as you think they do. I managed a single carry-on for all the in-transit essentials: diapers and wipes for the youngest, a change of clothes for each, passports and all other IDs, plane tickets and documentation, my laptop and wallet, a camera, a book, my phone, and a coloring book and pack of markers. Kids–even kids who travel a lot, like mine–can be entertained for a good long while with seat back safety cards, barf bags (make puppets!), headphones, and tray tables (sorry, passenger in front of us; I’ll try to keep it gentle).

Don’t pack the entire toy box. And as for all those things you think are essential: My rule of thumb when traveling is to not pack items you can buy at your destination. A caveat for Cuba is that you probably should pack all the diapers you’ll need; diapers can be tough to find and are expensive and of poor quality. Ditto wet wipes.

2. Stay organized.
Keep all the paperwork you’ll need in airports close at hand, organized and accessible. Bring along a notarized letter from your children’s other parent–even though many airlines don’t require them–in which that parent gives her or his consent to take your children abroad. You probably won’t need the letter, but you don’t want to be in a situation where you need it and don’t have it. Because my children carry both my husband’s last name and my last name (and because this confounds so many officials), I also carry birth certificates, a copy of our marriage certificate, and vaccination records as evidence of our respective identities and relationships.

3. Accept help if offered and ask for it if it’s not.
The toughest thing about a 14-hour day of travel was–I kid you not–finding a way to go pee without worrying that my one year old would tumble head-first out of her plane seat and onto the floor. Pressing my five year old into service worked for much of the trip and those tasks where I needed an extra set of hands, but never when I needed to go to the bathroom. I searched for a trustworthy-looking adult and asked them if they could watch my kids for a few minutes.

4. Trust your oldest with age-appropriate responsibilities…
… and reward them with praise (and, if you can, a special treat) for shouldering an extra load. My five year old pushed one of her siblings in a stroller through all three airports and even operated a special elevator by herself when we couldn’t all fit into the elevator for a single trip. I knew that she was a little scared, but I also told her I was totally confident in her abilities and that I was watching her the whole time (which was true). When we had a free moment, I bought her a small bag of chocolate-covered coconut as a thank you.

5. Know your danger zones.
I wish I’d thought to ask whether my airline, Interjet, had milk on its afternoon and evening flights, as both of my youngest children drink milk from bottles. It does not– it only has milk available on morning flights. On the last leg of our return flight home, I had no milk and kid #2 spent the last 20 minutes curled up in the fetal position on top of his tray table.

6. Ease your reentry.
I scheduled in a two-night layover in Mexico City on our return trip, mainly because I love Mexico City, my former home, and because I had some reporting work I needed to do there. But it also ended up being a welcome way to transition between Cuba and home, what with a comfy hotel bed, running water (which we did not have in Cuba), and a room service splurge. If you can break up your travels into more manageable bits, it will be easier on kids… and on you.

7. Take advantage of Trusted Traveler, Global Entry, and similar services.
When booking your tickets, make sure you elect for TSA pre-check if you’re eligible, and take advantage of your trusted traveler/Global Entry memberships if you have them so you don’t have to wait in line for ages when you return home.

8. Bring snacks. Lots of snacks.
Cheerios, fruit chews, apple bars… these are my go-to snacks for kids when we’re on the road or in the air. A snack produced with a parental flourish at the precise moment preceding a meltdown can prevent crisis.

Also, if traveling in areas where you’re not the one in control of when, what, or how you’re eating (as was the case at my in-laws’), bring some breakfast basics for your kids. Instant oatmeal is the best choice; it packs flat, weighs practically nothing, is easy to make, and is filling.

9. Have a clear work plan.
I had A LOT to do in Havana, and while I had my sister-in-law and niece to help care for the kids, I was still the one who had to fit all the usual parenting tasks in at the beginning and end of the day. Being organized before I landed and staying organized each day by following a work plan I’d set for myself was essential to not losing my mind.

Dispirited but not defeated

I don’t know about you, fellow freelancers, but the past eight weeks have felt like “The Twilight Zone” when it comes to getting paid.

Only you know that the problem won’t end after a 30-minute episode.

At first, I chalked it up to The August Doldrums: you know, editors and publishers going on that elusive thing called “vacation” while you continue to sit, fingers to keyboard, filing assignments and checking accounts to see if those outstanding invoices have been paid.

Once the calendar flipped its page to September, I was ready to follow up. With nearly $9,000 of unpaid invoices, most of which represented work filed months ago, I set aside time in my hectic reporting and writing schedule marked “INVOICE F/U.”

That “F/U” is for “follow-up,” in case you were wondering. I know- the temptation to read a double entendre into that is real.

I always feel resentful about spending time chasing down money I’m owed. It’s time for which I’m not getting paid, spent on work for which I’m owed, taking time away from new work that could be getting done, asking for something I shouldn’t have to ask for because I’ve followed all the rules and have honored my end of contractual agreements. But I suck it up, send out inquiries, pull up and reattach invoices “for your quick reference and convenience,” and look at what kind of crazy mathematics I have to pull off to cover my own obligations while I wait to get paid.

But this September has, thus far, been particularly bad. A publisher who owed $3,200, separated into two invoices, paid one invoice but not the other. When I followed up, they were surprised. There was another invoice? Well, yes. Yes, there was. Another publisher lost my invoices: could I send them again? And a third promised, repeatedly, that “payment was being processed this week,” only this week turned into three weeks, and no, I still haven’t been paid.

The kicker came today, when, after filing an assignment for a reputable outlet for which I’ve written a couple times (and have two more commissions in the pipeline), I wrote accounts payable to check on the status of an invoice filed at the beginning of August. I double-checked our contract: net 30. They were past it. Where was my money? I wrote, politely, to inquire.

What ensued has been an exchange of emails that has left me dispirited and disgusted, but not at all defeated. Many freelancers don’t follow up on payments; others apologize for doing so (“Sorry to be a pest, but I just wanted to check on my invoice, dated months and months ago!”). After the series of exchanges below, I am, more than ever, determined to be both diligent and dogged in pursuit of compensation for my work.

I hope you will feel the same. I also hope you will share this widely. Don’t let others devalue your work. Don’t continue to contribute to a system that doesn’t compensate you for your product; I can think of no other profession that permits this. Feel free to lift any of the language of my own emails and edit them to fit your own situation as you seek the payment you are owed.
Email One: From Me to the Accounts Payable Department of the Publisher


My name is Julie Schwietert Collazo and I’m writing to check on the status of an invoice that was filed on or around August 5. The project was [description of project], which was assigned by [name of editor]. The total due was [$xxx.00]. I have not yet received payment for this project; could you please advise regarding the status and when payment can be expected?


Email Two: From Someone in Accounts Payable Who Did Not Indicate His Position/Title

“Hi Julie: We are currently have a backlog with our freelance payments, we will get payment out as soon as we can. Please be patient and we’ll get you paid. Thank you!”

Upon receiving this, I stepped away from the computer to think. Would I write a “Ok, thanks!” email or would I let him know that no, this wasn’t okay? I thought about it for about 20 minutes and then responded:

Email Three: From Me to Untitled Guy #1 in Accounts Payable

“Hi, [name redacted]. Thank you for the update. Do you have an estimate of when the invoice will be paid?”

Email Four: From Untitled Guy #1 in Accounts Payable

“Not at this time. Sorry.”

Email Five: From Me to Untitled Guy #1 in Accounts Payable

“Dear [name redacted]-

This is an utterly unacceptable response, and one that I find disrespectful and unprofessional. I am not writing for a hobby; this is my profession. Like [name of publisher], I have bills to pay and not a single one of the people or companies waiting for payments from me would accept this type of response.

According to the contract with [name of publisher], it is clearly articulated that your obligation is to pay within 30 days of receiving the invoice. Please see the contract here, if there is any doubt as to that fact.

[I inserted a link to the contract, signed by both parties.]

If I do not receive payment by the close of business on Monday, September 21, I will pursue legal action.

Julie Schwietert Collazo”

Email Six: From Untitled Guy #2 in Accounts Payable

“Hi Julie,

My apology for the delay in payment. Please understand that the AP team was in no way trying to be rude or disrespectful and we do appreciate the service you provide to our Company. I’d like to talk to you live if you are available this afternoon so we can discuss your invoice and payment. Please let me know if you are available after 2pm PST and if [my phone number, redacted] is still a valid number to reach you at.

[name of guy #2 from Accounts Payable, who also doesn’t indicate his title]”

Email Seven: From Me to Untitled Guy #2

“Dear [name redacted]-

Thank you for your prompt reply. I’d rather receive explanation and next steps/payment schedule via email so that we have mutual documentation.

Julie Schwietert Collazo”

Email Eight: From CFO of Publishing Company to Me


[Name redacted] forwarded your email to me. I’m happy to jump on a call to discuss, but we will not discuss via email. Sorry if that is an inconvenience for you, but I’ve found email insufficient to discuss payment matters. Please let me know a good day/time/number to call you.

[Name redacted]”

Email Nine: From Me to CFO

“Dear [Name redacted]-

I’m not sure why you find email ‘insufficient’ for discussing payment matters; as far as I’m concerned, I only want to know when you intend to process payment and whether this problem with paying freelancers will continue, as I have another invoice I’ll be submitting for a work filed yesterday and I have two more assignments pending. If you are insistent that you must call, please be aware that I will record the conversation, which is legal under New York State law.

You are welcome to call me at [number redacted] anytime after 8 AM tomorrow. After tomorrow, I will be out of the country on assignment and without phone and Internet for 10 days, so I ask that this issue be resolved as quickly as possible.

Thank you.”

Email Ten: From CFO to Me


I’m sorry, we will not consent to being recorded. If you’d like to discuss payment without recording, please let me know; otherwise, we’ll tender payment when able.

[Name redacted]”

Email Eleven: From Me to CFO

“[Name redacted]-

I’m not asking for your consent. New York law clearly indicates I’m within my rights to record a call, with or without your consent.

It’s clear to me that you and your colleagues don’t intend to act honorably; you’ve made a clear-cut situation far more complicated than necessary, and your contract is absolutely clear about the terms of payment. If I do not near from you by tomorrow, whether by email or phone, with a specific plan of action and timeline for payment, I will initiate legal action.

Julie Schwietert Collazo”

Email Twelve: From CFO to Me


I understand your frustration on payment (I would be frustrated if I were in your position). I would like to discuss it with you. Payment issues happen in business from time to time. When they occur, they are not necessarily (and absolutely not in this case) a function of dishonorable behavior or deceit. We had a significant partner file bankruptcy, which has created this issue. We are working through it. You will be paid in full. If you would like to discuss the timing of this, I am very happy to call you to do so. But, I am in California, which does not allow recording conversations without consent. I do not consent to being recorded. If you want to discuss your payment without recording, I am standing by to do so. If you do not want to do that, you will still be paid in full.”

Email Thirteen: From Me to CFO

“[Name redacted]-

I certainly understand that ‘payment issues happen in business from time to time.’ I’ve been a business owner and, of course, as a freelancer, I’m frequently in the unfair position of being put at the mercy of a publisher’s ‘payment issues’… though I doubt you or others on staff absorb the similar–and very real– tangible, literal costs of such issues. Nor does your landlord, electric company, or Internet service provider, I’m sure, wait until issues resolve for you to pay them. Yet [name of publisher redacted], like too many publishers, expects freelancers to bear the brunt of the effects of problems they didn’t create. And, unfortunately, too many freelancers don’t assert themselves because they’re afraid they’ll never get paid, or that they’ll ‘burn bridges,’ a ridiculous notion, considering that they’re not the one who caused the problem.

It’s not unreasonable to want to be paid according to the contract we both signed. In addition, what continues to confound is: (1) why you would feel it is at all ethical to allow editors to continue commissioning freelance content in the midst of such problems (which clearly don’t have a resolution), and (2) why you wouldn’t inform freelancers who are due money what the generalities of the problem are, detail how it affects them, and present them with a reasonable resolution, one that has a timeframe attached to it. That’s fair and professional business.

I am not willing to have an off-the-record phone conversation. You can expect to hear from my lawyer.

Julie Schwietert Collazo”

and his final reply, which will not be met with a response from me, other than the one I’ve clearly indicated is my recourse:

“Understood. Please put him or her in touch with me. Happy to discuss with them.

[Name redacted]”

After a gaffe, the decision to be more deliberate

Like every other freelancer I know, I get stuck in the not-so-mentally-healthy “feast or famine” mode way too often.

That means one or more of the following:

-I take on a little too much work, work I can do, and do well, but which makes me a little nutty and has me in front of the computer too much.
-I take on a job I don’t really want or that doesn’t pay as well as I’d like because I’m afraid that if I don’t take it I might regret my decision when a dry spell rolls around.
-I spend extended periods in triage mode, ordering and reordering my to-do list by deadline rather than other factors that should probably take more precedence.

This isn’t good, of course, but for a long, long time–far too much of my career–I’ve felt that it’s inevitable, just part and parcel of life as a freelancer.

I’ve made incremental improvements every year, saying no to projects with ridiculously low fees or turning down some projects that felt far too fluffy, but there’s always more progress to be made… as I was reminded yesterday after making a terrible online gaffe involving an overly candid email sent to recipients who shouldn’t have been cc’d on the message.

The email, sent late in the evening, long after people with 9-to-5 jobs stop working, was a symptom–and an embarrassing one–of a larger problem. Despite recent vigorous efforts to scale back–unsubscribing from mailing lists that clutter my inbox and waste my time and saying no to a couple projects that didn’t pay well and were puff writing I don’t want to be doing, for example–I realized that there was (is!) still a lot of work to be done. I need to be more deliberate in every area of my work, and the first order of business is developing a better system for dealing with email.

I don’t know about you, but pretty much every time I look at my inbox these days, I already feel exhausted, even before I make a keystroke. There’s so much junk mail masquerading as important messages demanding my attention. There’s the feeling that I have to have my inbox open from the moment I’m awake until the moment I go to bed, in case an editor or source sends a message requiring urgent attention. And on and on and on. But the reality is, the less time I’m looking at my inbox, the happier and more productive I am. The less urgent everything seems–and is. And, obviously, the less likely I am to feel so depleted that I hit “Send” when I really need to give a message a second look and make sure that it’s appropriate… and addressed to the intended recipients.

This isn’t about slowing down, necessarily, though I feel like lots of freelancers write posts about that, setting goals that are difficult, if not impossible, to achieve. The reality is, this is not a profession for folks operating at a slow pace. It is, however, about being more thoughtful about each action, about taking the time to make sure that every word counts (and those that don’t stay in my head or between myself and my most trusted confidante, my husband), and about devoting time and attention to communication that truly matters.

Have you or do you struggle with similar challenges as a freelancer? I’d love to hear about them in the comments.

Wave Accounting: An Early Review

I always get a little nuts this time of year, nuts in a good way, in a “I am going to OWN next year” kind of way. I revisit my goals for the existing year and assess my success. I analyze how I can be and do better next year, not just as a writer, but as a business owner (because, you know, writing is a business). I take a close look at how I’m managing finances and at my overall systems, not only for money (expense receipts, invoices, and the like) but also for communication and task management.

As I started the process of assessing 2014, I realized that I really needed to get some new systems in place before 2015 rings in. My accounting system, in particular, needed an overhaul; it was scattered and inefficient. By drawing up original invoices every time I needed to bill a client, I was wasting a lot of time. And by doing this in Word or Excel and simply storing invoices in a folder on my desktop, I was creating extra and unnecessary work for myself with respect to tracking payments.

I started talking with colleagues, asking them what systems or software they are using. Some said Quickbooks or Freshbooks; others sang the praises of Harvest. I took a quick look at each of these, but was discouraged by the fee-based structures. I’m always looking for ways to trim my expenses, not add to them, so despite the glowing recommendations for some of these services, I was more inclined to look at free apps. Sure, I could try Quickbooks or Freshbooks free for two weeks or a month, but did I really want to go through the hassle of setting up accounts, inputting my financial information, and then shutting down the accounts in a few weeks? Instead, I decided to set up a new system on Wave, a free service.

It took about 30 minutes to establish an account and link several of my bank and credit card accounts to Wave. The interface was fairly easy to use, though I had difficulty with one bank account, and it was clean and uncluttered, too. The dashboard is a one-stop-shop for useful information.

I set up the invoicing system right away, as that was my primary reason for signing up for a Wave account. Creating an invoice is easy enough, but I wish the “Memo” section was offered in the default template as opposed to the customized one. When attempting to edit the invoice, the system got hung up and I had to refresh the page, which cleared the invoice, requiring me to start all over again. I’m also not thrilled about receiving daily (so far) emails from Wave informing me about features or services that I could be taking advantage of; perhaps I need to play around with my settings to turn these emails off.

I’m a little bit concerned about having all of my accounting information in the cloud rather than on my own desktop, but overall, I’m happy with the service. Wave tracks what I’d rather not, which is whether invoices have been paid, and has helped me to create a standardized system for billing clients. There was widespread agreement among friends that each accounting program has its pros and cons, and if the choice is between a paid service and a free one, I’ll take the latter.

What system do you use for accounting? Pros and cons? Share in the comments.

How to Ditch Your 9-to-5 Job

[Note: This piece was originally published on Matador, where I was managing editor and lead faculty member of the travel writing course. Over the next few months, I’ll dust off some other articles from my Matador days that I’ll be updating and republishing here.]

Since quitting my 9-to-5 job as the assistant director of a mental health agency in 2004 and becoming a full-time traveler and writer, many people have remarked that they envy my lifestyle. What they don’t recognize is that they can create the same kind of life for themselves by following a relatively simple set of steps, which I’ll share with you here. I didn’t plan the kind of life that I have now—in fact, I didn’t plan at all; I just quit my job without a Plan B, which is not the best idea for most people. My experiences of living on the edge, though, have helped me identify the top 10 tips for you to ditch your own 9-to-5 job and have a bit more security than I did.

1. Let go of your long-cherished vision of your professional self.
When I found myself unexpectedly answering my boss’s question, “How are we going to work together?” by answering, “We’re not, because I quit,” I didn’t realize that one of the biggest challenges ahead of me was letting go of the career trajectory I’d mapped for myself. By the age of 25, I’d been the first poetry therapist to work in two New York City social service agencies, I’d already reached the middle management rung on my profession’s ladder, and I’d simultaneously begun building my own counseling and consulting business with two colleagues. I was published in an academic journal and I was the director of a board. I was well on my way to fulfilling my high school yearbook’s prediction of “Most Likely to Succeed.” Dropping out of the profession meant I’d be disappointing a lot of people—my parents, who had paid for my Masters degree, my mentor, who had nurtured my learning and my career, and myself, as I’d planned big professional accomplishments by the age of 30. In order to ditch your 9-to-5, you’ll need to begin to let go of whatever conventional career plan you had for yourself and whatever expectations everyone has ever had for you.

Practice becoming comfortable with ambiguity and what others might consider to be aimlessness. Don’t underestimate the work this step takes. Our society is largely structured around the maintenance of the 9-to-5 life.

2. Perfect your pitch.
When you’ve made it through step 1 and you’re starting to become comfortable with the idea of the new professional you, one of the next challenges you’ll confront is explaining yourself and justifying your career and lifestyle change to almost everyone you know. Don’t be apologetic for your decision to forgo the traditional trajectory, but do take the time to develop a pitch or a story to tell when someone asks you why and how you’re forging a new path for yourself. A true and well-crafted narrative is compelling to most people—even those who’d like to see you conforming to social expectations—and it can often serve you well. When I explain how I was once a social worker who had her own business and worked as the assistant director of a New York City agency, then owned an art gallery, and then became a full-time writer, editor, and translator, it becomes a hook for continued conversation and often leads to offers of work and further exposure.

3. Make an inventory of your skills.
Whether you take the time to plan your transition or whether you jump into it headlong, as I did, it’s incredibly helpful to make a written inventory of the skills you possess that can bring you work and other opportunities. As I listed my competencies, I realized I had skills and knowledge that were so second nature to me that I hadn’t realized their potential value as sources of work. In this initial list, include everything that comes to mind—don’t censor yourself at all. If you can cook, clean, write, translate, organize, sing, type, take photos, transcribe, surf, do calligraphy, or make movies, write it down. If you’re short on ideas, ask a trusted friend to make a list with you.

4. Narrow the list.
Once you’ve made an inventory of your skills, review it and begin to narrow down your possibilities for independent work. Subject the items on our list to three criteria: (1) Which of the skills are portable? (meaning you can use them anywhere in the world); (2) Which of the skills are profitable? (meaning that they’ll generate income—not enough just to scrape by, but something to actually live on); and (3) Which of the skills have the lowest demand load? (meaning which will not require you to purchase special equipment, obtain employment authorization in another country, secure a work visa, or otherwise require negotiating red tape and the constant monitoring of bureaucratic requirements and deadlines).

5. Rework the list.
Now that you’ve determined which items on your list are most portable, most profitable, and lowest demand, begin to refine the list a bit more. What are the top five skills you could use to seek work that takes you outside of the 9-to-5 grind? Which skills might lead you to actual job leads? How can you generate work using these skills no matter where you go? Which skills will lead to work when you need it?

6. Plan with a partner.
If you’re in a serious long-term relationship, you need to discuss your ideas and plans with your partner. Ditching the security of the 9-to-5 life and trading it in for a life that is more independent and flexible is not for everyone and it requires risks that may not be acceptable for all people. When you are in a relationship, the needs and abilities of your partner with respect to adapting to your plans need to be discussed and agreed upon. What kinds of shifts may need to occur in your day-to-day life in order to make the transition realistic and to what degree is your partner willing and able to accommodate and support you?

7. Assess your security needs.
If you’re the type of person who needs medical and dental insurance, a 401(k), and a steady, predictable paycheck, then you will need to do some serious planning to fulfill these needs before ditching your full-time job. There are resources for meeting these needs off the regular workday clock (see Freelancers Union for some great ideas), but you’ll need to do most—if not all—of the legwork on your own. You’re now the chief, cook, bottle washer, and human resources director.

8. Be for real.
Before you ditch your 9-to-5, do a searching inventory of yourself. The main criterion? Be for real. Are you a person who needs structure? Do you work best with others? Do you have a hard time scheduling, organizing, or delegating your time well? Do you need the praise of a superior or the affirmation of colleagues? Are you envisioning life off the 9-to-5 grid as one long adventurous, romantic narrative? If the answer to any of these questions is “Yes,” it’s likely that you’ll find life off the time clock to be a serious challenge. Among the many people who have commented that they’re envious of what they view as my freestyle life, there are a couple who have acknowledged that they’d never be able to follow in my footsteps because they need a boss, they need the predictability of a regular paycheck, or they need someone to assign tasks to them. I admire these people because they know themselves and make their career and lifestyle decisions realistically according to their own personal and professional needs.

9. Create community.
Working off the clock has many advantages, but it can get lonely at times, especially after the initial thrill of working on your own wears off. Be sure that you’ve made plans for connecting with other people no matter what you’re doing or where you are.

10. Assess your progress.
Every once in awhile, take some time to assess your progress. When I stop to think about how my life has unfolded since turning in my resignation and never turning back, I recognize that I work more now than I ever did, but that I’m also happier than I ever was. I also realize, though, that I need to continue refining my short-and long-term plans in order to maintain my current lifestyle. Since I don’t have a boss to sit down and do an annual performance evaluation with me, I need to do constant evaluation myself and so will you.

Worth Watching: “Freelance Strategy Hacks”

There’s a lot of material here that will be old hat for long-time freelancers, but I learned a few useful tips in Shane Snow’s video “Freelance Strategy Hacks,” and I think this is especially exceptional advice for folks new to freelancing.