Before I turned 33, had kids, and started driving like a grandma, I used to “occasionally” get pulled over for speeding.
Most people mentally deduct $150 from their bank account the moment they see the flashing lights. But the cops would almost always let me go — without giving me a ticket.
Why? Because I controlled the situation, instead of reacting to it.
When the cop approached my car, I didn’t ask stupid questions — or worse, try to argue. I just rolled down my window, turned my interior light on, and put my hands on the steering wheel at 10 and 2.
When he asked for my license and registration, I didn’t just reflexively reach into my back pocket (never, ever do that). I asked permission and told him exactly what I was going to do.
Finally, I apologized, and asked if it was possible to avoid a speeding charge.
9 times out of 10 this strategy was enough to get me off the hook with just a warning.
By knowing how to tilt the odds of a traffic stop in my favor — and knowing exactly what to expect — I was able to make all the right moves.
Your first freelance writing job works the same way…
Last week, I asked you what was holding you back from moving forward in your freelance business. The most common answers were:
“What if I’m not good enough to deliver?”
“What if they find out I’ve never done this before?”
“What if they don’t like my work?”
But notice what all of those doubts have in common…
They all put you in the reactive position.
What if you flipped that around and figured out how to be in control of your first freelance writing job — so those issues never come up in the first place? Here’s how…
RULE #1: ASK THE MAGIC QUESTION
Years before I started freelancing, I was addicted to watching The Apprentice.
Every season featured one or two challenges where the contestants had to create an advertising campaign for some big brand.
And every season, someone got fired because they didn’t ask the client the magic question: What do YOU want to see in this ad campaign?
They thought their job was to come up with an original idea — when all they really had to do to win was make the client happy.
The contestants who did ask got clear instructions that made their task easy. And the client was practically guaranteed to love their work because it was exactly what they asked for.
Everyone else worked extra hard…with practically no shot of winning.
HERE’S HOW TO USE THIS TO NAIL YOUR FIRST FREELANCE WRITING JOB:
Ask the client to show you a CONCRETE EXAMPLE of a similar piece of work they like.
Example: If they’re hiring you to write a movie review, ask them for a link to a movie review they think is great — and ask them what they like about it. Then write something similar, and listen as they sing your praises.
Btw, if you’re looking for freelance writing jobs on Upwork (which is where you should be looking), you’ll often find these types of examples right inside the job description.
RULE #2: COVER EVERYONE’S ASS
Have you ever noticed that no one ever storms out of The Cheesecake Factory screaming and cursing?
Meanwhile, restaurants with 10x better food have to deal with pissed off customers all the time.
Cheesecake Factory waiters are trained to cover everyone’s ass — their own ass, the company’s ass, and the customer’s ass, too. When you order a steak medium rare, the waiter responds with: “That’s going to have a warm, pink center; is that OK?”
Notice how he didn’t say, “Are you sure?? Because once I order it, it’s too late to change your mind!” That would be a one-sided ass covering. (Don’t do that.)
Instead, he helps you make a good decision by telling you exactly what to expect — which benefits both you (the customer) and the restaurant.
Smart restaurants know that as long as your expectations are in line with what they’re going to give you, it’s almost impossible for you to leave unhappy.
HERE’S HOW TO USE THIS TO NAIL YOUR FIRST FREELANCE WRITING JOB:
Right before I start working with a new client, I send them a quick message to let them know exactly what to expect, and to prevent any possible surprises. Here’s what it looks like:
Hi <NAME>,
I’m excited to get to work on this with you! Before we officially get started, I’ve put together a few quick notes to make sure we’re both on the same page moving forward:
- I agree to complete <WRITING TASK> for you by <DATE>, for the price of <DOLLAR AMOUNT>. (Please note that this includes 2 minor revisions. If more work is needed beyond the scope of this proposal, I’m happy to complete it at my hourly rate of <DOLLAR AMOUNT>.
- I’ll deliver the first draft to you (in a Microsoft Word Document) by end of day on <DATE>.
- If you feel any revisions are needed at that time, just let me know what you’d like me to change, and I’ll send you an updated draft within 2 business days.
- If a second round of revisions are needed, we can repeat #3 above.
If this all sounds good to you then I’d love to move forward and get to work. If there’s anything you’d like to adjust, just let me know and I’ll do my best to accommodate you.
RULE #3: USE CRITICISM TO YOUR ADVANTAGE
I wish I had a dollar for every time a newbie freelance writer asked me, “what if the client isn’t happy with my work?”
What they don’t realize is that you can use the client’s criticism to your advantage. I do it all the time.
Take this blog post as an example. Do you think I just banged it out and published it on the first try? Of course not. First I showed it to my friend Radhika — and she told me 37 things that were wrong with it. (For one thing, the word “ass” appeared way too many times…it was disgusting.)
For me, Radhika’s feedback is so valuable that I’m willing to pay for it. With clients, the deal is even sweeter: YOU get paid to get their feedback.
The key is to get the right kind of feedback.
Most freelancers send their first draft to the client and bite their nails waiting for the client’s comments.
But most clients don’t know how to give feedback in a way that actually helps you. What you’re looking for here is CLEAR, SPECIFIC instructions, like “Please make the first sentence shorter.”
If you don’t tell the client HOW to give you helpful feedback, he’s more likely to say something like, “The length of the article isn’t quite right” — forcing you to guess what he really means.
HERE’S HOW TO USE THIS TO NAIL YOUR FIRST FREELANCE WRITING JOB:
You can show the client how to give you helpful feedback with a message like this:
Hi <NAME>,
Based on what what we discussed last week, I’ve completed a first draft of <DELIVERABLE>. I’m excited to hear your thoughts on it!
Sometimes, minor revisions are needed (as a reminder: 2 of these are included); here are a few quick tips to help you convey what’s needed and ensure we end up with the best possible finished product:
- You can type your comments/suggestions right into the document, or we can schedule a call so you can tell it to me over the phone
- Please be as specific as possible (e.g. “Can you mention at least 5 beaches” is better than “Can you be more thorough?)
Thanks again — looking forward to your thoughts!
-Danny
Now that you know how it’s done…
My goal is to show you that anyone can be a freelance writer — it isn’t magic.
Here’s another secret the Old Pros won’t tell you: We all have doubts sometimes.
When I hear that little voice that says, “Are you good enough?”, one of my tricks is to focus on WHY I became a freelance writer in the first place. For me, it’s about being able to control my schedule so I can spend a lot of time with my wife and kids.
You might have a different reason. Maybe you want to travel around the world, without being chained to a desk. Maybe you just want to be able to work while enjoying a coffee at Starbucks. Or maybe you think it would look cool on your Tinder profile.
What’s YOUR reason? I don’t care if you haven’t gotten started yet…tell me about your “why” in the comments below.
Don’t hold back. Even if your reason is weird — like wanting to break the record for most Burning Mans ever attended — I’d love to hear about it.
Hi Danny!
I have several reasons why I want to become a freelancer.
First, I will graduate this summer yet it’s so hard to find a copywriter job with decent pay for my experience (which is none).
Second, I’d love to have more streams of income so I can travel and live the life I want.
Third, I get bored easily, and sitting 8hrs straight at a desk doesnt work for me.
Hi Danny
This was a very valuable post. I started freelancing because I wanted to have the freedom and time to do what I want
the reason why I like working as freelancer the main reason is that id love to work and have income while I’m with my family, more time with my family is the reason.
I’m going to make this happen because I’ve been a stay at home mom for nearly 18 years and living paycheck to paycheck most of that time. I’m tired of being poor.
I loathe this house we’ve outgrown and I despise my 20 year old rusty minivan.
Our future will be brighter than our past because of freelance writing. Thank you for the invitation to tell you tell you about, and remind myself of, my Why.
Hey Danny, my reason is to be able to live free and be able to choose the people around me, so I can sort the toxic people out. And thanks for this amazing article! It was really helpful!
The 8 to 5 starts feeling like a millstone round your neck after sometimes and it feels like I have an astonishingly cruel large one pulling me down right now. The idea of working my own hours and also negotiating the value of my work is enticing. Written words are captivating and I would really love to see my words bring joy to someone out there or make someone’s job satisfactorily complete. I have lived my life in the confines of my country and although I have travelled a little, I would really love to join that huge pool of… Read more »
I’ve been a database administrator for over twenty years. For the past four years, I’ve contracted with an agency that allowed me to work from home most of the time. That contract ended, and I’m back to working “on-site,” meaning I have an hour’s commute each way, every day. The previous contract spoiled me. I really enjoyed being able to work from my home office, cats purring on either side of my standup desk, coffee pot five feet away. Lunch breaks were taken sitting at the bistro table in the middle of my garden. Occassionally, I would take my laptop… Read more »
I want to be a freelance writer because it is a job that I can do almost entirely independently. I’m highly introverted and have a low threshold for working around people and have always wanted to do something where I could work mostly by myself and save my emotional energy for the people in my life that I really care about. I want a source of income with essentially no ceiling and I want to set my own schedule so that I can travel when I want. I also want the option of staying at home when I decide to… Read more »
The reason why I want to be a copywriting freelancer is because I wanted to make money as fast as possible whilst improving the skills I’m most comfortable at: writing.
I want to be financially independent ONE YEAR from now so that I can leave my family home & rent a good apartment with good facilities & good internet for my business. I’m also really interested to move on from my current sedentary lifestyle to active lifestyle where every morning I wake up and jog and do exercises that strengthens my body.
I hate “office work”. I’ve always loved writing but have been scared for a few years now to delve into online work. It’s quite scary as I live in a very traditional household and country, and job security in “traditional markets” is the key to survival here. I want to be a freelance writer so that I have the freedom to give my family a healthy life, spend time with them, and actually raise kids, instead of fully outsourcing that to schools. I want to be a more deliberate wife/mother/daughter. Writing online would afford me that freedom. And travel. I’d… Read more »
Danny, this article is absolute gold! Thank you so much for sharing. I’m completely new to freelancing and your backstory of struggling to find a job you love completely resonates with me. I’ve decided to get into copy writing as a method of generating side income but thanks to kind folks like you who are willing to share your stories of success with the world, I now dream of being a full-time freelance copy writer. Also I love that you don’t over-complicate things for all of us newbies. You have a gift for explaining things that are easy to understand.… Read more »
Hi Danny, for me, as the Queen of Self-Doubt-Country and ruler over I-am-not-“insert random adjective here*-land, this article is SO helpful (as anything else here, actually, as I mentioned in my email I wrote you like an hour ago before)! My “Why” is clearly my unability to work in a conventional job, since failing one after another made me even MORE doubting and self-concious and even pushed me into a serious depression…. I always thought there was something wrong with me, until I discovered that it’s not ME who is kinda wrong but my professional circumstances! And this was a… Read more »
Hey Danny, I have been on the fence for quite a while now and hope to break into the world of Upwork as a freelance writer. I have enjoyed writing since I was young and at present am working in a Business School, and looking for a more flexible lifestyle, This would definitely give me some more time to spend with my wife and kids and plan my life a bit. Your valuable inputs as well as your “Freelance Copywriter’s Course”, which I have just registered for, is just the right platform I need to get off the blocks. The… Read more »
I am just coming off of a job with a really toxic company culture. Even though I was able to work from home, I never saw my family because I was constantly at my desk or checking my phone. The notification sound became a thing of nightmares!
I want to be able to continue contributing to my household while still engaging with the people who are most important to me.
Hi Danny My reason is that I love to read, write, and as it turns out research! I got into this whole idea of “the barefoot writer’s life” two years ago after seeing an ad for AWAI. Now, I never took any of their courses, but I did become a member so I could tap into lots of free resources (but I had to pay for the magazine) and I watched or listened to many webinars, took tons of notes and so on. My GOAL is to someday make enough for me to let my husband retire and us to… Read more »
My reason for wanting to be a freelance writer is simple: freedom. I want to do what I love (writing and helping others succeed) in a way that allows me to not worry about being unable to pay my bills or enjoy my life. Being stuck in one location doesn’t sound like the kind of life I want–If I feel like going on a week long trip and I have everything I need paid for, I want to be able to do that. If I feel like going outside is too much work but I don’t want to waste the… Read more »
I’m a freelance software developer / administrator.
Why?
Because with job like this, I can evolve in multiple directions – and be more than another one engineer.
I’d like to spend more time with friends and interesting people, study marketing, business, biology, play musical instruments, run own company, involve in human life extension movement & be able help projects that worth the most even if they have no finances!
Already have some success with freelance – taking a next step to the future right now!
I enjoy writing, I want to do more of it, get better at it, and be able to work from home and care for my mum, take her on holidays while she’s still able
I just want to help my mom get out of stress.
And also make enough money to help my family
I’m saving to join your course Danny – played with your free tips and landed a few jobs already
I just recently heard of this profession and am astounded, as well as disappointed. Wish I’d heard of this decades ago. I’m soon to be 56, and am incredibly bored, lol. THIS is more my alley! I’m presently looking to relocate my family of four adults; have recently recovered from major neck surgery so am unable to work a “normal” job, whatever that is; and my creative juices refuse to work in the traditional job setting! I’m heading out on this new career with courage and confidence, though this is new to me. I’m hoping my years in the Retail,… Read more »
I AM NEW FREELANCER I SEND ALL MY ORDER A CANT GAIN ANY ONE
These blog posts have been so helpful and inspirational to me. I am wanting to become a freelance writer in order to lessen the financial burden on my spouse so she can also do what she really wants. Also to give my 2 young boys a better life.
I have learned more reading 2 of your post than I have in the whole six months Ive been reading and researching this business. I want to start writing so I can finally make enough money to give my little girl a better life. I want to be able to take her to Disney and see her enjoy it instead of sending her with another family because I can’t afford for both of us to go. I want to be location independent so I can travel with her. I want to get out of this old trailer and into a… Read more »
Hi Danny, I don’t have a website-I hope that is not something you need to be a freelance writer because I have no money to set one up at this time! I have been trying to find a legit work at home job for some time now. Of course my mailbox is full of the work at home scams; so many I have no idea how to unsubscribe from them all! I am a 60 yr old former R.N. who retired from that profession in 2009. I worked as an R.N. in many capacities over a 30 yr span &… Read more »
I just love writing. Writing is my way of expressing myself when no one is around to listen. I remember during high school days, I used to write on my planner and make a diary of my daily experiences, thoughts, and feelings.
Until now, I’d still wanted to do this hobby, and try some other kinds of writing.
And since I love writing, I wanted to try this as one way of earning.
Thanks, Danny.
Hi. I have question about getting started on upWork. I am new to upwork but not to Grapgic design. I ‘ve had steady jobs in my field since 2006 and for many ears now I have owned and operated a grahic design site with success, but clients have been trickling in lately and I wanted more work, so I upwork seems like the place to be, but mannn is it different. I can see alot of clients want “90% job success” and such. Also it looks bad that I have no job history so what should I charge at first?… Read more »
My reason, because I’ve always wanted to control my schedule, and travel. I’m 19 graduated college early as a Environmental tech, but unsatisfied with being controlled I decided to make this my full time career. I’ve always loved writing. Still is my favorite hobby. Nice to see i can get paid for it.
Excuse the typos.
My “why” is to have the financial freedom to keep doing what I’m already doing. I’m a missionary and I love it. But getting funded is not what I’m good at. I have long experience as a writer. I’m trying now to put that to good use, hoping to earn enough income a few hours a week so I can spend the rest of the week with mission work. I’m also specializing in “cause writing,” so that even my writing work can delve into the causes I love so much. Thanks for this great article and the reminder to reflect… Read more »
Why do I want to be a freelance writer? Oh, let me count the ways…. First off, I have a BA in Education specializing in English and an MA in English. I taught at university for 3 1/2 years and LOVED IT. Then, surprise, I got pregnant and they fired me. I was an adjunct so I had zero money and suddenly a new baby to take care of and try and support. I was out of work for 6 months–because no one wants to hire someone who’s main job on their resume is teaching American literature to college students,… Read more »
Very helpful article
My main reason is the need for a challenge. I am a very driven person and an office job only keeps my attention for a short while. I believe I have the skills and the right attitude to build my own business.
Then I would also love to spend more time with my two small kids, who are now mostly being cared for by their grandparents while I am at work. I also have a long commute, which means I get to spend even less time with them.
Danny,
I am reminded time and time again why you are so good at what you do. To the point and accurate. Thanks so much.
I want to free up my time and improve my income to travel and visit my kids and grandkids more
Cheers
Howard
I want to become a succesfull upworker so I can stay at home as a foster carer and support the children a thousans precent when it comes to appointments, homework, parent meetings and just being them for there when their parents are unable to. I hope this dream will come true.
Hi Danny. First off, I’m grateful for all the insights you so openly share. You know, you’ve actually managed to chip away a few layers of jade from this 50-something guy’s crusty ol’ heart. That’s quite an accomplishment. I’m only half joking here. But I’m not kidding when I say I’m excited to get started on this journey. Why? Because, like you, I really want to control my time. I’ve spent way far many years with colleagues and bosses instead of with my wife and five sons. It’s sickening how many of their milestones I’ve missed. So, from the bottom… Read more »
Hi Danny, thank you for encouragement.
I stumbled upon your blog today. I was desperately looking for tips to help me get started with freelance writing. I want to do this full time, but I have no idea how and where to get started. My reasons are simple enough. Want my means of earning a living to be independent of location and time. Want to be able to make use of the various freelancing platforms out there, to have an unconventional lifestyle. Don’t want to be tied down to a desk for the next 20-30 years. My problem is that I have no idea how to… Read more »
I wanted to be a freelance writer for several reasons: – Being a writer is such a cool thing – girls look at you with respect. People bow down to you. – Being a freelance writer tells that I am a rebellion who doesn’t like t stay behind a 9-5 job and wants to enjoy sitting in a coffee shop writing and getting paid for it, too. – Yes, I want to make at least $10k per month, on auto-pilot, through my blogging so that I can travel around the world and just be able to find tons of time… Read more »
I want freedom from my 7 am to 5 pm job (yeah, it’s 10 hours for me).
Freedom is what is pushing me to become a freelancer.
I am home with my daughter, who is homeschooling, and want to be able to bring in an income doing something I love that lets us live comfortably.
I want to control my schedule, and along with it, my destiny. I don’t want to have to cover shifts for coworkers who happen to be sick on a given day. I want to have the flexibility to devote my energies to the things that matter, like become a professional boxer and future world champion.
I’m not writer (English is not my first language), but I’m children’s book illustrator. I could work full time as a freelancer when I lived in Ukraine few years ago. And that experience was the best what happen with me in my carrier. It was so great I had enough time for my family and could travel a lot. But now I’ve moved to Canada and I need to earn much more then before and it’s much harder to get money for life only by freelance job. So now it’s my dream to become a freelance artist again.
I want to be able to earn enough money to buy the very best health promoting foods.
I want the time to be able to do extensive movement/exercise each day.
I want to have my body looked at and fixed by professionals (chiropractor for example).
I want to be able to continue travelling the world.
Most importantly I want all of the above so that I can achieve my goals of helping to improve peoples lives by motivating and inspiring them to become the best version of themselves.
I have always had this crazy ambition of traveling all over the world and giving myself the chance to experience many different cultures around the globe. This is even more true for me now that I have a daughter and want to give her those same experiences. For me, Upwork is my key to being able to move around the world yet still make the income needed to support the lifestyle. The simple pleasure of knowing I am in command of my job is such an uplifting feeling. Thank you Danny for all that you have done for those on… Read more »
Is learning to write to a professional standard difficult, or time consuming? I would love to be able to earn a decent living, away from an office environment.
Great article. I’ve read through your blog. The Crystal Ball Technique is genius. This really circumvents the need for years of experience.
I loved to write short stories but that was a long time ago. I never thought of myself as a copywriter but now I see how important this is for everything in life, you can do anything if your writing is good and keeps people reading. It even forces you to organize your thoughts. Your article, once again, has a great story and great lesson, both for writing and for our daily lives (you made me laugh when you mentioned driving like a grandma, I am so much like that too now that I have a family). Thanks again! I… Read more »
My reasons:
I just simply love writing!
I am working on becoming a copy writer because I want to create a discipline around writing that will help me to do my own writing. I have taken Danny’s course and I can say the it is very well made and full of good intel that is based on sound Psychological principals. Rome wasn’t built in a day. Romulus and Remus started out as pups sucking at the teats of a wolf. They had to grow up first before they could start building. I know!! t takes all kinds to make a world. I just replied to my first… Read more »
I want make myself really useful and earn some extra cash, to be self employed!
I would LOVE to become a freelance writer because I need the flexibility to write in my own time, while also working on our newly acquired vineyard. We are the peasants as well as the owners 🙂 so combining physical work with some of my favourite mental work AND earning some extra money would be a dream.
My husband left me and my nine year old daughter a year ago. I have been a stay at home mom for nine years. I can’t find a job that pays enough so I work two. I am close to losing our home. I sold my car and bought an old one so I could have the money. This situation has left me desperate and scared. I haven’t gotten started yet because I am not sure how to begin, but my “why” is so I can get to a point where I never feel this way again. I don’t want… Read more »
Donna, take a breath. I’m sorry for your situation but I know no one is sorry he asked. I am a single parent with the father not being involved and sometimes I just want to go rock myself in a corner. 1. Sign up on upwork, 2. get your profile set up, 3. peruse some jobs and send off your proposal to one. You were a stay at home mom and we all know that takes you being able to balance lots of things at once and make it effortless. You can do this! If its possible see if your… Read more »
I’m new here. I’m also a single mama! We can do this! I would love to hear updates from the 2 of you. ????
I love your articles because they are always inspiring and full of useful information.
My “why” is to be able to travel around the world, work whenever I want from wherever I want and spend more time with my future husband.