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17 Steps to Set Up Your Freelance Business


After getting your first client, the business and finance side of setting up your freelance work can be tricky. As I began my self-employment journey I had a lot of questions. Questions about finances, and how to set up my business, like: Did I need to be a LLC? What should I do about insurance? Are there any business checking accounts that are free? Why do state and federal government make simple things so difficult and convoluted? And so much more! So here are a few things I’ve learned in the last month if you’re getting ready to go freelance, or have been for a while but still haven’t set up the automation and finance side.

And one giant WTF! HELP ME! outstanding question about taxes and the IRS at the end of this post.

17 things you need to do first:

#1. Decide if you’ll be [Your Name], a “DBA”, or a LLC
state and federal website sadness

In the state of Oregon a “doing business as” (DBA) is called an “Assumed Business Name” and is only $50 for two years ($25/year), while an LLC in Oregon was $99 through Legalzoom & $100 Oregon filing fee (annually). If I was doing business as my first and last name I wouldn’t even need a DBA as well. I decided to go the DBA route and in the future if I want to LLC something I can do that then. Now let’s just pause and take a minute to reflect on how poorly designed government websites are. And don’t even get me started on the website copy! Ok, moving on…

#2. Get a Tax EIN #
One of the downsides of being a sole-proprietor is having your social security # out there (on W9s for clients, bank accounts etc). But one thing I learned is that you can file with the IRS to get a Employee ID number that is linked with your social security #. It’s free and it takes a few minutes to fill out online.

#3. Open a Business Checking account
Most major banks offer a “free” business checking account, meaning that they require a minimum balance for it to be free. I decided one of my requirements was to find a FREE free one, as I wanted to keep most of my balances in a business savings account and I didn’t want to have to engineer a system around remembering to keep a specific amount in it. Especially as I started out, I didn’t want to be transferring over “personal” money to my business account. So you have a few options:

Major Banks & Credit Unions:

-US Bank – it was kind of a hassle to set up, but once it was done and all linked up with my Savings account it’s on auto-pilot. You have to go in to a location (with your DBA or LLC proof, TAX EIN (not required, you can just use your social security #, ID, and $100 cash or check). Expect it to take about an hour. The first time I went in their system crashed and I also found out they wouldn’t take my non-US Bank debit card or my non-US bank routing #/account # for the $100. Since their ATM would have charged me a fee (seriously?!), I walked a few blocks to an ATM to get $100. Thankfully, the second time I went in, they had most of the info saved in the system so I didn’t have to start from scratch.
-Credit Unions – many local credit unions also offer free business checking too. Here in Portland, that includes Advantis Credit Union, Unitus Community, and OnPoint.

#4. Sign up for a [miles earning] Business Credit Card
so smug because she's getting miles
I was a little excited for this step! I’m into miles and a bit of a “travel hacker”, so I jumped on the CitiBusiness AAdvantage World MasterCard offer. 30,000 bonus American Airlines miles for meeting the $1,000 minimum spend within three months. I don’t have a lot of business expenses, but I’ll make sure I spend that within three months even if I need to pre-pay some things (like next year’s hosting costs, my health insurance etc). I should be covered though with other startup costs like my second monitor, business cards, health insurance, and some software over the next couple months etc.

#5. Open a Business Savings account (optional)
Having a business savings account isn’t a required step. It’s not like interest rates are going to give you much return (at the moment), but I may as well have my money sitting in a savings account, and that’s an extra layer between the required checking account. I went with ING Direct Savings (errr Capital One 360 Business Savings). Honestly, it’s been a pain in the ass with the back and forth of them needing all this documentation that I’ve sent over and over. C’est le vie, it’s done now. And after I finally got it opened, they informed me that I can’t transfer money to my personal account (when I’m “paying” myself) even though it’s under the same login. And I also can’t add my personal account as an External Account to transfer it either, so I’ll be using my US Bank checking account as the go-between when I need to pay myself.

#6. Set up all recurring expenses to charge to your business credit card
So after my card arrived, I switched any recurring expenses that were previously on a personal card that I had to figure out at tax time previously (like hosting costs), and also made sure my “default” card for anything else like software products etc had the business card saved instead of a personal card.

#7. Order business cards
I placed an order with Moo (with the new business credit card remember!). If I could change anything about this step of my process I would have done this sooner! Well I did want to wait until my business credit card came through, to meet the minimum spend for my bonus miles, but I went to a few networking events and meetups the two weeks after my “1st day” and I didn’t have cards, which was fine because it ended up being something to talk about, but it would have been nice to have a few to give out. :) Also, I found out after I ordered that if you use someone’s referral link, you get 10% off your order and they get $7.50 in credit. Oh well, next time!

#8. Get your desk and office area in order
Remember, I was already a remote worker for my previous company. When I had first started there we had an office and then a few months later we all went home to work. So my computer equipment had belonged to my employer, but since I didn’t want to take a giant bulky ugly desk home to my studio I opted to purchase my own desk at IKEA. It’s just a simple and small saw-horse/2-leg/slab top combo. Plus, one of their small $10 round rugs to go under a chair, and then I bought a desk chair finally this last year! So in the “office” department I was all set.

While I can work from anywhere, like when I’m traveling, and I do go to coffee shops some afternoons, I’ve found it helps that when I am home, I have a corner of the house that is my work space even though it’s not a dedicated office.

#9. Get any extra computer equipment you’ll need (like a 2nd monitor)

I already have a MacBook Air, and a VGA-out monitor cord that I’ve used when I worked while traveling previously, so I pretty much just needed a second monitor. I’ve found that having a second monitor is pretty essential when I’m analyzing something or even writing if I need to compare things. It’s a huge time saver, I don’t necessarily “need” it every day, but for the projects that I do need it I am ever so thankful for it. I ended up buying this 23″ monitor on Amazon for $150 and it had a $20 rebate too! You could spend a lot more, but this is perfect for what I’m using it for.

#10. Find Health Insurance
I had Kaiser Permanente (an HMO) insurance with my previous employer. It’s not awesome insurance, but the price/value is great if you are healthy. Tip: If you’re leaving a job, check when your insurance ends and how much it would be to extend it through them. The whole “COBRA” thing only applies to companies that have 20 or more employees, so if you work for a small company all that great legislation that was put in place for equality and fairness or whatever, doesn’t apply to you! Yay! How interesting! So after you find out how much it will be, get some online quotes (eHealth is great for this) too. I ended up calling Kaiser and they asked how much my previous employer was going to charge if I continued through them for a few months and she informed me not to do that because the same coverage solo was actually cheaper! Remember a lot of insurance will let you set up auto-pay from a credit card. A great way to get mileage points!

#11. Use your new business credit card for ALL business related expenses
Then link it up to auto-pay the full statement balance on the due date from your business savings account. This will give you at least a month of float on your expenses. Example: I bought my monitor for $150 on October 4 with my CitiBusiness card, the statement date for that expense will be Oct 31, the due date will be Nov 21 and it will auto-deduct from my bank account. This also allows you to earn miles or rewards for all your business purchases and keep your money in your savings account for longer. Win/win.

#12. When you get paid, deposit it into your business checking
From there move it to savings or just deposit in savings. (Since I’m starting with client freelance work, I won’t be getting lots of checks. It will usually be large and infrequent, compared to if I was selling a product) so really I just wanted a Business Savings account until I found out that you can’t get a business savings account unless you already have a business checking account. Ha! From talking to a few other freelancers, they just deposit all incoming checks into one account (personal) and then have learned to deal with the feast/famine of invoicing and payment delay. While it doesn’t really matter where the money is “sitting” (it is all my money) I know for my own personality that I need the consistency of paying myself. So even if I make more money from one month to the next, I’ll be keeping it in business savings account and “paying” myself a consistent amount every month. I’m hoping this will also make it easier at tax time.

#13. Set up accounting software
Wave Accounting app
A few freelancers that I know use Quickbooks online. I won’t be having tons of transactions, so paying $13/mo or $156/year is not a necessary business expense for me. Originally I thought I would use a few categories and labels in in combo with a Google spreadsheet or the Expensify app. But then I found Wave accounting software which is free! It’s kind of like Mint for small business. It’s absolutely the perfect solution for me.

I ended up adding my ‘business’ accounts to Mint and then deleting them to just keep business stuff in Wave and personal stuff in Mint. Then, I will try to pay myself on a monthly basis by transferring money from business to personal. At least that’s the plan right now.


#14. Use Time Tracking software
harvest example screenshot
Harvest app has a free plan. I use that. Maybe if I get big and fancy I’ll upgrade but really for now I don’t see myself paying for this service. And I don’t need to invoice through it (and Wave appears to have an invoicing option). I have used Google Docs to track time previously as well. TenXer is another data tracking option that I love (for more than just working). But overall, I’m using Harvest right now, as I like the ability to track time easily to specific tasks groups and have it automatically fall under billable/non-billable in a weekly report.

#15. Decide on a task/project planning service
Whatever your task management system of choice is, figure out what you’re going to use and put a system in place. I use Asana for personal tasks and recurring items, so although I tried it at first for client project management type work, and it felt a little jumbled. So I’ve been using Trello for planning out client projects and of course Google Docs for the actual content  (documents, spreadsheets).

#16. Set up a blog/hosting
I already had hosting service, so I just bought a domain name and hosted through my current service, using WordPress. I also found a great responsive theme on Creative Market’s weekly freebie area a few months ago that I thought maybe I’d find a use for at some point. My business website serves as a “home” for my consulting offerings (like email marketing strategy and implementation, analytics, etc.) and as a place where I can blog about marketing/small business.  

#17. Figure out Taxes
From the looks of it, it appears that I have started my business too late in the year to have to worry about the next quarterly tax payment so I’ll be filing my 2013 taxes as usual in February and then doing the quarterly estimate taxes next year. I am still 85% confused on this topic so if anyone has any tips that would be great! From reading the IRS site it sounds like they “suggest” you file quarterly, but then if you do it and estimate wrong then they’ll fine you? Huh? I am so confused on this still! Help!?!

Did I miss anything? And any help on the taxes question? (Other than the standard “ask a tax professional” response).

#57: Read Seth Godin Books That I Haven’t Read


small-is-the-new-bigThe Dip51drpze7irl_sl110_

#57 on my 101 Things in 1,001 Days List was to read all of Seth Godin’s books. I was already about halfway done, when I added this to my list, but then he just kept on writing books! Give a girl a break, and let me catch up! ;) If you’re unfamiliar with Godin, he’s a best-selling marketing and business author who writes “bite size” marketing books and a blog.

My favorite book of the 12 is Small Is the New Big: and 183 Other Riffs, Rants, and Remarkable Business Ideas. I like how this book is divided into alphabetized one page blurbs. While not all 183 are “remarkable” ideas, it’s a great way to bring you out of the details of getting things done on a day-to-day basis. It adds a little caffeine to your marketing day. This book is better listened to than read. I really enjoy listening to an audio book that’s narrated by the author, because it’s much more personal and you feel like you’re getting the right tone/inflections.

I just finished his last book, Tribes — We Need You to Lead Us.  As usual, it was a quick read and resonated with me in a Gandhi sort of way, “be the change you want to see in the world”.  This book isn’t on how to be a better leader, just about deciding to lead. I think my favorite thing was going to read the review on Amazon and finding this in the Editorial Review section:

“The advice found in this book should be used with caution. Change isn’t made by asking permission, Godin says. Change is made by asking forgiveness, later. That may be true, but in this economy and in certain corporations, it may also be a good way to lose a job.” –Publishers Weekly

Hilarious! Seth Godin, are you laughing?

My only critique with Godin’s writing is that he’s often too quick to dismiss stable and “boring” businesses. There’s a time and place for unconventional (that’s why it’s not called “conventional”). For example, I don’t want my toilet paper to be hip and clever– it’s just toilet paper. And it doesn’t matter how “outside the box” your company is if you’re still unprofitable. I am a huge fan of his books though, I just like to take everything with a grain of salt.  :)

meatball-sundaeunleashing-the-ideavirusthe-big-red-fez 51pin3xfrdl_sl110_ permissionmarketing all-marketers-are-liars free-prize-insidesurvival-is-not-enough

5 Ways To Streamline Your Job Search


It’s been over a year since I quit my job to travel.  Now that I’ve been back on the job hunt for a month, I’ve assembled a list of ways to streamline your job search.

  1. Set up RSS feeds. Just because you’re unemployed doesn’t mean that you want to spend hours every day combing through the same websites.  First, create a list of sites that you frequent for your job search.  Then, using iGoogle (personalized home) or Netvibes, create an extra tab and start adding RSS feeds and/or bookmarks (if RSS isn’t available).  I use,,,, and a few industry/regional specific websites.  I also have a Note widget on my iGoogle that I use to record the date, company and position I applied for, just for future reference.
  2. Template your resume and cover letter. By assembling several resumes and cover letters you can save time when you actually find a job to apply for.  I’m not suggesting you do a “find and replace” on the company’s name, but if you have different cover letters geared towards different industries and highlighting specific skills, it makes it that much easier on you to personalize it further.  Why reinvent the wheel everytime?
  3. Put the word out. Assuming you’ve already assembled a killer resume, email it to your network.  While friends and acquaintances are higher in quantity, people who have seen you in action (coworkers/bosses) are usually more valuable, leverage that relationship.
    In search of desk and a job.
  4. Manage your online presence (eg. Sign up for LinkedIn). As much as I loath using internet marketing buzz words,  if you’re on the job hunt it’s imperative that you use it to your advantage.  Not only should you know what the first 10 Google results are for your name, but you should be on LinkedIn (and actually using it).  Also, if your Facebook and MySpace profiles aren’t set to “friends only” or “private”, take a look from a future employer’s perspective.  Even if you’re employed you should be aware of this.  Last year, I had the laughable good time of looking at my assistant’s MySpace page to discover that his “cronic migraines” were instead hangovers (as posted back and forth between himself and a friend).  Thanks for making my job easier buddy!
  5. Find ways to stand out from the noise. Seth Godin and Auren Hoffman had good posts about this recently.  Economic downturns flood the job market with “talent.”  However, it’s also a great time to let go of under-performers.  So while you might be an A-player, your resume will blend in with all the C-players out there.  So find a way to stand out.  A few ideas:  make your cover letter content useful, get recommendations on LinkedIn,  leverage your contacts who can attest to your A-playeresque (my new word) qualities as recommendations.

Along with the above tips, I also try to allot a specified amount of time per day for job searching, (almost no exceptions).   By living your life as if you were gainfully employed — including getting up at a reasonable hour and putting clothes on — your job search is just part of your daily routine.  Personally, this puts the “demoralizing” part of being unemployed to a minimum.

Got any job searching tips?  Do share!

#5: Finish my MBA

I’m finally done! After 2 years of part-time classes, I’m officially done with my MBA! After undergrad, I had no intentions of getting my MBA, and I’m glad that I took some time away from school before going back. It gives you some perspective on what you’re learning.

What did I learn? Not what I thought I was going to learn. When we first started the program, one of the professors said that getting your MBA usually isn’t about what you think you’re there for. After the first year, that really sunk in. So yes, I learned how to apply business school principles to my job, but more than just statistical analysis and economic theory (which are helpful if you know when and how to use them), I learned about myself. Yes, that sounds kind of cliché, but I don’t really care. There’s definitely something to be said for everything you learn in business school, but the process is just as important. Note: I did not just use the word “journey”. OK, I’m going to go buy a wooden bead necklace, practice meditation and drive a Pious, I mean a Prius; maybe later I’ll stop wearing a bra and discuss my personal vision. :)

The 4 Hour Work Week – Week 12: 52 Books in 52 Weeks

I have mixed reviews about The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich. First, it’s an excellent reminder of how short life is and that we should pursue what makes us “happy”, not stay in dead-end jobs etc. However, I really dislike the idea of “outsourcing” your life and producing or managing random products (that don’t create value) just for revenue, to go live selfish lives.

Differences of opinion aside, it’s great to be reminded of taking mini-retirements. The first section is about fear and defining what you’d like to do and the worst case scenario if it didn’t work out. The next section covers freeing up time, so it’s kind of the opposite of “Getting Things Done” and more about streamlining so you have less to get done. The rest of the book was about outsourcing your life and generating income, so I really enjoyed the first half of the book a lot more. Overall, I would recommend the book because it makes you take a closer look at the life that your living (or not). Sometimes it’s good to take a zoomed-in look at your life, decisions, and future plans.

The List: 52 Book | 52 Weeks

Olivia Raymer
Things I ♥: travel, food (I'm a pescatarian), the Pacific Northwest, bikes (I ride an orange mixte), beer (IPAs), summer, coffee, lists, and kitties. Travel enthusiast, former product manager, dabbler, and currently helping small businesses with digital strategy at Early Bird Strategy.

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