Everything I know about freelancing, so far
By Joe Berkeley
When I became a freelancer, I spoke with a lot of people who were kind enough to help me. This is what I learned from them, and from my experiences.
1. Incorporate. You don’t need to hire anyone or pay legal zoom. I live in Massachusetts so I had to get an Employee Identification Number first. Get your EIN for free at:
Now you need to incorporate. You can do it here. It cost me $500. Again, no need to pay a lawyer, legal zoom, or anyone else. The people who work in the building in Boston where this happens are really nice and helpful.
2. Start a checking account for your business. You’re going to have to do this twice, once while you’re waiting for your LLC to be formed, then again afterward once the paperwork goes through.
3. Interview 10 people you know who are successful freelancers and find out what works for them and what doesn’t. Most successful freelancers want to help those starting out and most of them have some time. Expect that you will have to go to them. Some freelancers are now on staff, and they will want to talk to you because they have happy memories of freelancing.
4. Meet with your accountant. Review your assets, your obligations, and figure out how many days a year you have to work at your day rate. Then figure out how many days a month that equals. Then factor in that your first month is going to be slow. Don’t panic. You will get work.
5. Set up your book keeping on quickbooks.com. When you get work, send the invoice the day you finish. People take a long time to pay you, 30 days is fast, so there is no sense giving them a reason to delay another day or two. If you don’t want to use an online bookkeeping package, set up two folders on your desk top. One is invoices, the other is paid invoices. When you get paid, move the invoice from one folder to the other. It’s simple but it works.
6. Don’t pay for linkedin premium. I think this is a bit of scam in that they just want your money. You can get what you need out of linkedin on their free platform. It might be worth the money if you want a staff job, but I’m not positive about that.
7. Get business cards at moo.com, go for the luxe, they will be money well spent. When you meet with someone at an agency, you will have better business cards than they do. You want them to save your card so when they need someone it’s on their desk.
8. Put all of your expenses for your freelance business on one credit card, do not mix the business expenses with personal expenses. No co-mingling. If you have two credit cards in your wallet right now, make one of them the business card. You’re going to have to buy some stuff. I went to Staple’s and bought an office chair, some paper, paper clips, printer ink, all that stuff you used to get out of the company office supply closet for free, now you gotta buy it.
9. Set up an office in your home in a room that is dedicated to your business. It should be a separate space for tax purposes. This is a great thing to do in that home and work are going to be smooshed together. By going to one room in your home you are “at work” and when you leave that room you can be at home. My commute up to the studio is about 18 seconds. I have a dedicated space that I built when I was a staffer because I knew I would one day be freelance. I put my desk near a window and my office is a clean, happy place with lots of natural light. There is room for an art director and a planner.
10. Open an email account on Gmail, as google spends a lot of money on their product. If you have an email on aol.com or yahoo it makes you look like a dinosaur. Set up a skype account and figure out how to use it. Geography doesn’t matter anymore, this is all about talent.
11. Use google calendar to plan out your days. You have to be your own project manager, google calendar can keep you on schedule.
12. Get familiar with file sharing software. A lot of times I get on the kick off call with the client, who has about 9 minutes to brief me. He or she typically sends me the document in file sharing software so I to load the software and download the document during the call.
13. Be really nice to the client’s assistant. I got a couple of assignments to write campaigns for feature films. The client was very busy and the briefing was short. After the briefing, the client’s assistant was able to get me the scripts that went with the films so I knew what I was writing about.
14. Contact all of the people you have worked with over the years. They are most likely your source of freelance. The junior writers and junior art directors of yesteryear are now creative directors. If you were kind to them, there’s a chance they will be kind to you.
15. Reach out to freelance directly for clients you know. This is a great deal for them and for you. The agency billed you out at three or four times your current day rate so the client is getting your beautiful brain at 66% off. What a deal.
16. The first day you freelance for someone, bring your passport or ID with you. Some employers have to see one or the other to get you in the system. Have your W-9 filled out on your desktop of your mac. You are going to get really good at filling out forms: non-disclosure agreements, confidentiality agreements, non-competes, etc. Read the documents before you sign them. Be nice to the Form Master or you will have a really hard time getting paid.
17. Your portfolio should be up to date and easily edited. I use cargo collective and I’m happy with it in that I can turn work on and off depending upon the prospect.
18. Set up meetings with people you know who may have work for you. Try to stack up five meetings on each day. One of the people will cancel at the last minute. All of these people will give you something; confidence, a lead, an idea. Maybe one of them will give you work someday.
19. Find some freelance partners you can work with, as many agencies don’t want to find one for you. You should have a nice list of reliable, talented, quality people who deliver.
20. If you are on Cobra, call your health care provider to confirm you still have insurance. It usually gets screwed up and if you find out when your kid is in the ER with lacerations to the head, you are going to be mighty angry. Do it when no one is bleeding.
21. Relationships are more important than geography. If you are good friends with someone who is doing work on the opposite coast, you can freelance for them from your side of the country. Reach out to them. They may travel you, they may not. But if you do a great job and solve the problem, you will get invited back for more.
22. When you do get invited to travel, you may save a lot of money by booking your room on Air B’n’ B. Check it out online. Like all things freelance, this isn’t a black and white issue. Some hookers have used Air B’n’B for entertaining their clients and there are probably some nut jobs hiding in the closets in super hero costumes. But if you are male, of reasonable size and prepared to defend your honor, it could be a good idea.
23. Get recommendations from co-workers and clients for your linkedin page. There is a two-week window of opportunity where people will want to help you. Most people require 30 days to write the recommendation after they say they will.
24. Try to stay even. This is a tough one. Because the highs are higher and the lows are lower. When you book a job, you are ecstatic. When you’re slow, you may think, “OH MY GOD I’M NEVER GONNA WORK AGAIN.” You will.
25. This may be a good time to freelance. Most of the established freelancers I have spoken with have made more money as a freelancer than as a staffer. But the income stream is less predictable. Which is why a lot of freelancers with young kids go back to staff. It’s not that they didn’t make enough, it’s that they couldn’t live with the uncertainty. It’s hard to budget when you have no idea what you’re going to make and when you’re going to make it.
26. Spend less than you make. If you make a dollar freelance, you should save at least 33 cents for taxes. There are also hidden costs to freelancing. Healthcare costs more. No company match for the retirement plan. You have to spend money to find assignments. You don’t get paid when you go on vacation.
27. Don’t buy stupid things. I love to read car magazines. As I was drooling over the latest German-built Un-Obtanium sports car, my very wise wife said, “Yeah, Sparky? How many days of freelance you need to work to buy that thing?” Damn. A lot of days. So that’s not gonna happen. But I did manage to publish a story about cars in one of my favorite car magazines, Hemming’s. I shot the photography, wrote the piece, and got a full-color page layout. Half a dozen readers wrote letters saying they loved the story. And Hemming’s paid me with…a hat. Yes, I got a fully-adjustable, poorly art-directed baseball hat with a flat brim that was not ironic in a hipster, gangster kind of way. Now, I wouldn’t work for any agency without getting my day rate. But I always wanted to write for a car magazine and I checked that one off my bucket list. When I met with a potential client at a furniture store, he said, “Oh, I got a ’69 Camaro. I saw your story in Hemmings!”
28. Get an app to keep track of mileage on your car when you use it for business purposes. I use mileagebug. Save all of the bills; cable, electric, heat, as a portion of them can be written off. Your job is not to be the accountant. Your job is to provide the accountant with all of the information he or she needs to do the books correctly. Even if your account is Abraham Lincoln, do not give him or her access to your money. Plenty of creative people have been fleeced. Do not be one of them.
29. Have a project outside of freelance that is 100% positive for when you don’t have work. The reality of freelance is it is not even. I worked 24 days in a row in February, then only two in March. As a staffer, you were used to “the machine” dropping assignments on your desk. Now you have to go find the assignment. Some jobs are three-day assignments. Other jobs I’ve heard of where people get into huge agencies and end up “perma-lance” for a year before someone in accounting figures it out and makes them get out or take a staff job. The outside passion project, whether it’s fine art, fitness coach, the Great American Novel, whatever, can be really good to keep you positive.
Here are some of mine from the past year: lost 25 pounds, published stories in Boston Globe, Hemmings, Laser Sailor magazine, Sailing World, restored a wooden boat, won a national championship in said wooden boat, competed in Laser Worlds in France, rebuilt the Weber grill, created a blog about freelance life, worked on a novel and a biography, perfected my relationship with my Labrador retriever.
30. Work with your accountant to pay your quarterly taxes on time. This is on the list twice so you don’t forget. The IRS is going to get their cut so eat the pain early. Pay your taxes and enjoy life. If you don’t pay your taxes, well, it’s going to get ugly. I try to pay mine a day or two before they are due. There’s an old saying I think of. If you’re going to eat a turd, don’t nibble it. Gobble that turd. Paying taxes is one of the biggest turds there is and it’s good to just get it out of the way.
31. Set up a SEP IRA or a Keough or some other retirement plan that your retirement specialist/accountant/smart spouse thinks is a good idea. When you pay your quarterly taxes, also make a deposit into your retirement account. You used to have beautiful benefits. Now you have to cobble your own together. The one good thing about this moment is it makes paying taxes suck a little less because at the same time you are putting a little something away for yourself.
32. Get your 401(k) out of your previous employer’s plan and roll it over into a IRA you control. I sent out a request for proposal to numerous financial firms including Fidelity, Merrill Lynch, Morgan Stanley, and Vanguard. After a careful review, I chose Vanguard because of their low fees and positive reviews. Here’s a tip. The company that is holding your money right now doesn’t really want to give it up. When you call them, they will want to give you the runaround. So if you choose another firm, have the new firm set up a conference call with you and the old company. Because now there are two companies recording the telephone conversation, your old company that doesn’t really want to give you your money, and the new company that really wants it. The new company knows which words to say that will make the old company cough up your money.
33. Get on “working not working” if you can. Post on facebook you are looking for a code. Or ask someone who is on the site to nominate you. All the cool kids are there and if you are on the site it will make you happy. Workingnotworking now has a “pros not bros” policy and your work will be reviewed by their new screening team. So it’s not a guarantee you will get in but it’s always good to try.
34. When a bill goes past 30 days and you haven’t been paid, get on the phone and politely ask if the bill got lost in the system. First time you freelance for an agency, your bill may be lost. It’s not personal. Be extremely nice to the person who does the paperwork in accounting. When that person asks you for your W-9, send it as soon as possible.
35. Think of yourself as an entire business all in one person. You are new business, creative, accounting. So part of every day you have to be prospecting for your next assignment, collecting bills, etc. It takes ten “maybe” assignments to get one real assignment. It takes a couple of phone calls and emails to get paid, even if the person you reported to was ecstatic with the work.
36. Decide how you want to spend your time. Remember how you resisted the urge to buy the Porsche/Hinckley/Rolex/luxury item goes here? The luxury you own is freedom. You are free to choose what you do, who you do it with, and what experiences you want to enjoy. In the summer, I get up early and start working by 4:00 am. That way, I can give my clients a solid 10-12 hours of work, then quit by 4:00 pm and go for a bike ride or a practice sail in my Laser.
37. You are going through a transition right now, which feels strange. Be motivated but do not jump at the first crap staff job that comes your way. Watch the film “Lemonade” a documentary about people who used this period of their lives to reinvent themselves.
38. Pricing, ah, the mystery. Most shops will want to beat you down a bit on your day rate. Factor it in. There are some jobs where they want to beat you down so much it’s just not worth your while. Figure out what the least amount is you can work per day then do not go below it. When people say, “I’ll take care of you on the next one,” it is a lie. There is no upside to working for cheap people once, why do it twice? Some people don’t budge on their rate at all. Others say yes to everything. A freelance recruiter told me the right way to go about it is to pick a happy medium. Maybe you can be flexible on the day rate if it’s a 10-day gig. Maybe you can be flexible on the day rate if you can work from your studio. Just be really clear what the scope of work is. I had one client that wanted 27 pieces of creative written in two days. I’m fast, but I’m not that fast. I took a pass. Nobody would’ve been happy.
39. Clients you should avoid: most of them are small business people who have never paid a creative person. Generally speaking, they want to know what you are going to do before you do it, then they don’t want to pay you. Run the other way. Tiny tyrants should also be avoided. I met with a wealthy client who was developing a massive real estate project. He berated the art director I brought to the meeting and was a pompous ass. When this five foot, two inches tall gentleman spoke, his staff all quivered like abused animals. I got the feeling that the staffer that invited me to the meeting brought me in to feed the lion his daily quota of meat. After the meeting, I told the staffer, “if I worked at a big agency, I would tell you that we had a great meeting and I’m going to figure it out. But you know what? I don’t work at a big agency. I work for me. And your boss is mean. And there’s no way on God’s green earth I’m taking this job.” Keep in mind this feels really good when you do it. But for the next two weeks, I did not have any work. So I paid for my principle. That said, I believe this pompous ass of a human being would have ruined my life for months for a short money project fee that would have humiliated all involved and rewarded no one.
40. Don’t be the person who is looking for work. Be the person who is doing something interesting while looking for work. This is all about your passion projects that could lead to new and interesting connections and assignments. Journalists say, “one clip leads to the next.” Photographers say, “one photo leads to another.” In my spare time, I was going to Laser sailboat competitions on the weekends. Since no one else was doing it, I decided to write up regatta reports that ran on the fleet’s facebook page. That lead to stories in the Laser magazine. That lead to a Hall of Fame sailor asking me to work on a book with him. It may pan out. It may not. But new possibilities are being created.
41. Find a community you can join. Freelancing by yourself can be lonely. It’s great to be part of a group of like-minded people. Maybe you join a basketball league, volunteer at the church, or get involved in town government. Find a place where you can spend time with people who are like-minded. I spend my free time surrounded by people who love to race small, inexpensive sailboats. It’s good for the soul. I show up with proper equipment, sail fair, and go to the after-racing social activities. Then I write stories about the events. That’s all it takes to make an entire fleet of friends.
42. Be very careful with people who want a “project fee.” You know, how much for, some brochure concepts, copy, and revisions, it’s not that much, really. Ah, well, how many revisions? How many days of work? What is the approval process like? If there is someone in the organization that enjoys torturing people, and you have agreed to a flat project fee, you are going to get crushed into a fine powder by a large, corporate steam roller. Be specific about what you are going to do up front so you don’t get burned on the back end. Scope creep can crush you when you are a sole proprietor, a freelancer, or a small business person. Be specific about what the job entails.
43. The Freelance Fairy is a mysterious little minx. When you go looking for her, she runs the other way. Then when you stop looking for her, your phone rings and there she is. Let’s say it’s a Monday morning. You woke up, ate breakfast, took a shower, shaved and put on some pants so your significant other does not give you a hard time about freelancing in your underwear. You have no work today. The right thing to do is to do some quality prospecting, send out five emails or call people who may have work for you. Tend to the books a little bit. Catch up on paying the bills. Work on the passion project. Book some meetings with people. Then Walk. Away. From. The. Mac.
If you sit there looking at the screen or your iPhone, the Freelance Fairy is going to know it and nothing will happen. If you forget about it and go about your business, the phone will ring while you are at the supermarket buying bananas.
Conversely, if you really want to get a three-week, full day-rate offer, book a vacation. The second the non-refundable plane tickets are purchased, the Freelance Fairy will show up in a seductive outfit with a beautiful assignment.
This is a tough one and there is no easy answer. I have worked on assignments on vacation when I could, like a trip to Martha’s Vineyard. I got up at 3:00 am, started working at 4:00 am and knocked out a full day of freelance by noon. And I have said no to assignments when there was no time to work like when I was at the Laser Worlds racing sailboats in France.
Even veteran freelancers have no idea what makes the Freelance Fairy appear. Yesterday, I had coffee yesterday with a writer who has been freelancing for 12 years and is working more than 200 days this year at his full-rack day rate. It’s a mystery to him.
44. People do not call you back unless their hair is on fire. I can’t tell you how many calls I’ve received, “Can you be in New York tomorrow, we need you for six months!” Then they never call back. It’s not personal, they just solved the problem and forgot about you. Maybe the assignment went away. Maybe the person who called you got hit by a bus. You’re never going to know so don’t waste time thinking about it. This is not personal.
45. Some people want to have a meeting before they hire you freelance. Okay. Everyone gets one free meeting. That one meeting should be enough for them to get the idea. If they want another meeting for free, be careful. There are all kinds of creatures in the “Waste Your Time” Forest. You will learn how to identify them all. Most professionals who hire you will say this, “Hi, it’s Jane from Acme Advertising. We have a big pitch coming up. Are you available for two and a half weeks starting next week? What’s your day rate? Oh, great. I’m going to send you a non-disclosure agreement, a confidentiality agreement and you can join the kickoff on Monday. Any questions, call my assistant.” That phone call took less than two minutes, and you have 2.5 weeks of work. Usually the longer the call, the less likely you are ever going to get any work out of it, so proceed with caution.
46. Time is relative. When you are at the agency, how many months passed between the time an assignment was created and the time it was produced? Was it enough months to give birth to a child? Build a house? Create an independent nation? Agency time moves slowly. Some accounts create one commercial every two years. Freelance time moves quickly. You want an assignment now. You want an answer now. You want to get paid now. You have to remember that the agency person who may hire you has a zillion problems and you are the least of their priorities.
47. The iPhone is the business. Get the best service you can find and make sure the phone rings when someone calls you. The person at the agency has a list. There are many names on it. If you don’t answer the phone, the next person on the list gets the call. The person at the agency doesn't want to call you. He or she has to call you.
Think of yourself as a plumber. The pipes in the house are frozen and water is leaking everywhere. This is an emergency. First plumber to answer is probably going to get to fix the leaks.
48. Reduce your overhead where you can. When I was staff, I paid for a company to mow my lawn. It was $75/week. Now that I’m freelance, I do it myself. It’s easy and it gives me the chance to keep an eye on my property and there’s something hypnotic about the sound of the lawn mower that inspires me to think of new ideas.
By reducing your overhead when you can, you put yourself in a position to be able to enjoy your freedom. That said, don’t go nuts, declare Marshall Law, fire the cable company, drop the heat to 48 degrees and have the kids wear hats in the house. If the family revolts, you lose.
49. Have a Cash Cushion. Figure out how much it costs you to live and have enough cash on hand to be able to live if you don’t have work for a month or two. The Cash Cushion enables you to enjoy life and keeps the Freelance Fairy in line. Otherwise she can drive you crazy.
50. You were humble at the agency. Get over it. Come up with a two-sentence answer to, “what have you been up to lately?” Here’s mine. “In the past ten months, I’ve won four pitches and one national championship. I have an offer to write a book and a major project with a big agency that is about to go into production. I would love to work on a project with you.”
51. There is a cliché in journalism, “one clip leads to another.” In photography, it’s “one picture leads to the next.” When you get an assignment, there are a lot of things that could happen as a result of that assignment. If you don’t have an assignment, use your passion project to make connections and contacts that could lead to something else.
52. The Steady Gig, the Holy Grail. The best outcome is to have half a dozen clients that give you steady work rather than 100 clients that give you one day each. It’s tough finding steady work, but do everything you can to make your project clients happy. The goal is always to do such a good job you get invited back. You know you’re doing a great job when you get an offer to join the staff. I’ve met freelancers who have had steady clients for decades.
53. There is a lifecycle and a rhythm to everything in nature, including freelance. There are times of the year that are going to be slow. You can work really hard prospecting for work from December 23-January 2. But it could be more productive to enjoy that time off as almost everyone is thinking of eggnog and Santa and champagne and family. No one is thinking about hiring a freelancer.
54. If this is going to work, your spouse, life/partner, pet, parents, dependents have to be onboard. If the important people in your life are fighting you every step of the way, you just can’t do it. You need 100% support from the people who matter. Have a sit down with them to discuss the pros and cons of freelance.
55. If you created an LLC, you can’t just set it and forget it. There is an annual report that needs to be filed once a year. Ironically, in some states, you only file it once every few years. If you don’t file the report, the LLC is dissolved and you have to do all of the paperwork again.
56. Follow my blog, freelanceisgood.blogspot.com Be inspired by those who have done what you want to do.
57. Create a routine such that you get to exercise regularly. This is a great way to deal with stress and it helps you stay even. You are also less likely to get sick if you are fit and healthy.
58. A friend says “spot hero” app for smartphone can save you 50% on parking spots. She goes to her meetings and uses the apps to save a ton.
59. Embrace your inner problem solver. You are going to have to solve marketing problems, computer problems, accounting problems, new business problems, getting paid problems. It’s all on you. At first, it hurts. But after you figure out how to crack one problem, the others are easier to figure out as well. This is going to make you much more versatile as a person and more independent. Celebrate each little victory and be a good friend to yourself.
60. Give every assignment everything you have inside of you. There are no small assignments, only small hearts. Put your heart and soul into each one, as sometimes the small assignments can lead to great things. Today, I am writing a biography for an artist’s Wikipedia page. Is this more important or less important than a Super Bowl TV commercial? I don’t know and I don’t care. But I want to write the best Wikipedia entry in history because I have not written one before. Sometimes a trail of crumbs can lead to a fresh loaf of bread. Treat each assignment like it is the only one people will ever judge you on. Make it great.
The biggest gift you have now is freedom. Millions of people have fought for freedom, died for freedom, and been imprisoned because they dared to live as free men and women.
All you have to do is make some phone calls, send out some emails and solve the problem when you get the assignment. Being freelance isn’t as easy as being staff, and it’s not always perfect, but everything about it is yours. The first time you hold a check that you earned with your talent and your work is a very rewarding moment.
If you have any questions, let me know and I’ll do my best to answer them. I want to help you because there were some good, decent, kind people who helped me.
Remember the people who help you. Forgive the people who don’t and start living a happy, simple life, free of drama and bullshit.