Freelancing for Beginners: Here’s How It’s Done

Freelancing for Beginners: Strategies and Solutions

I think that when we come out on the other side of this Covid-19 fever dream that is the year 2020 that many employers and people are going to want to stick with the remote working situation. What we have learned thus far in 2020 is that there are very few jobs that cannot be done via your couch. So long as you have the appropriate tools, you’re golden.

We already see that many workplaces are trading their meatspace workplaces for armies of remote, contract, and part-timers happily be-clad in worn out college t-shirts, flannel jammy bottoms, and fuzzy slippers.

In fact, this was already happening BEFORE Covid-19. All the work I have applied for in the last 12 months has been companies looking for 1099 employees. (Read: contract, freelance, remote.)

And, while working at home with children is like a siege, there are also a lot of benefits that come with doing so.

It’s hard to see your screens, but working at the beach or pool is THE best

The 5 Best Benefits of Being a Freelancer

  1. There is no time card – PMs on most freelance jobs care about the work getting done on deadline. They don’t care when you are actually working on the project. You do have to demonstrate the hours you worked, but you don’t have to punch in and out. This is awesome.
  2. Freelancing = freedom – You can work from anywhere you have WiFi. Do I need to explain this one? Let me demonstrate: Flash to 2 years and change ago. My British Ex-Husband and I wanted to take a trip to Ireland and then London. I had work. But, I didn’t have to take any time off. I finished my work in and around the tours of the Guinness factory, and Downton Abbey (Highclere Castle.) And, all the other fun we were having. I only had to sacrifice an hour or two in the morning, and the same at night. Which I probably would have been doing anyways due to the time difference. Being on vacation and making money while doing so is a revolutionary act.
  3. You choose what you work on – You don’t have to work with brands you don’t like. Or on projects you feel are dull or beyond what you’d like to be doing. Once you establish yourself as a credible freelancer in your field you can pick and choose what you work on. You don’t have to accept sketchy work. Feel like a contractor is going to be demanding and a micromanage you? Don’t take the gig. Red flags going up about the company’s credibility? Say no and run into the arms of a better assignment.
  4. You always have a strong negotiating place – 9/10 times the employer needs you more than you need them. This puts you in the enviable position of being able to negotiate salary, timeline, scope of work, and deadlines. For example: A lifestyle publication recently approached me about writing a series of 5 parenting articles. They wanted to pay me $X, but $Z is my standard freelance rate per word. I told them that, said I wouldn’t take the gig at that rate. They came up to $Y per word. And, offered me a featured spot in the masthead with a photo (which was an acceptable compromise.) I was prepared to walk away from the assignment if they didn’t come up in price and benefit. Because they needed my content more than I needed to work with them. Freelancing is often a lot like playing poker with Kenny Rogers — you gotta know when to hold em, know when to fold em, know when to walk away, know when to run.
  5. Once you establish yourself, work will come to you – Again, this doesn’t need much explaining. Once you are known, employers will seek you out and ask for you to work with them. This is the enviable position I am in. I hope you get there, too.

This All Sounds Great, How Do I Start?

It is simple. Decide what you want to do and start doing it. Freelancing for beginners is an easy thing to start up. Don’t quit your day job, but start doing it. Want to be a writer? Find a few hours a day to blog. Want to be a photographer? Start asking friends if you can do shoots with them and post the results on your Instagram and website. Want to be a costume designer? Volunteer at community theaters or for student film projects. Just figure out what you want to do and start doing it. Whenever you can, wherever you can.

If you’re good (or even if you’re only so-so) you’re going eventually hit effective frequency. And someone, somewhere will offer you the chance to do the thing you do for some sum of money.

Don’t get all excited when it happens and quit your day job, you have a long way to go my little butterfly.

Soon you will fly free, my baby butterfly freelancer…

What Does the Baby Freelancer Do Next?

There are several areas you need to attend to before you can call yourself a bonafide freelancer. And/or even think about quitting your day job. These are the things a freelancer must have in place before they go live:

  • Build a Roadmap for Success
  • Create a Portfolio of Work
  • Shine Up Your Resume and References
  • Find Out if You Need a Business License
  • Save at Least 1 Month’s of Rent/Expenses
  • Decide How You Want to Work Freelance
  • Look at Your Financial Structure
  • Register With Staffing Agencies and Freelancer Websites
  • Pitch Your Ass Off
  • Build Up a Few Reliable Freelance Clients

Let’s begin with these freelancing tips…

A roadmap can be a bit like Shoots and Ladders

Build a Roadmap for Success

I hate the phrase “business plan.” It seems so staid and boring. And, part of the reason you’re working to leave the 9-to-5 grind is to leave phrases like “business plans” behind.

But, if working in strategy for 20 years has taught me anything, to have success you need a working plan to get there. Freelancing is no different. There are three reasons you want to create a roadmap for yourself –

  1. You need to determine what your overall goal for your freelance career is
  2. It’s important to break that goal down into actionable steps
  3. Providing yourself a way to measure your ROI (return on investment) is really important

Is my roadmap static?

Nothing in this world is static, freelance baby. Your goals will change month-by-month, year-by-year. Sometimes day-by-day. What is important is that you keep in mind why you’re deciding to go freelance. Creating an overall goal helps you see that. Personally, I reassess my goal yearly, and I reassess my steps to get to that goal on a monthly and daily basis.

Your roadmap doesn’t need to be formal. As Michelle Goodman says in My So-Called Freelance Life, “All you need is a short list of your freelance goals for the year – a roadmap of where you want your career to go, and some directions for how to get there.”

An example of a beginner freelance roadmap

Recently, I returned to full-time work after taking about a year off to be home with my daughter. I had to go back to the beginning and rewrite my own roadmap, as my goals and methods had significantly shifted since the last time I wrote one. I want to show you mine, so you can get an idea of how simple a roadmap can be.

Overall goal: Rebuild a client list which will provide full time income

  1. Create new portfolio with my most current work
  2. Re-do my resume and reach out to references to ensure they will still provide me with a positive review
  3. Write on my blog at least once a week
  4. Optimize my blog for SEO and build a roadmap to monetization
  5. Work on my social media presence
  6. Pitch at least 3 new clients per month
  7. Pitch 1 big publication per month
  8. Do as much business writing as I need to in order to build a solid nest egg

If you want to be microgranular, you can break these down into subgoals, month-by-month -or- day-by-day. It’s also important to keep in mind what your biggest goal is. For me, it is to buy a house with a yard for myself and my daughter. And, to work hard for the next 5 years so that I can eventually free up time to travel with my kiddo (and, British Ex-Husband) and spend more time on really creative, outside the box projects.

Really, it’s up to you to decide what your goals are and how to get there. Dream big, plan small – just realize that it will take time and patience to get you to where you want to be.

Here is the front page of my portfolio as an example

Create a Portfolio of Work

It should be pretty obvious why any freelancer, let alone a beginning freelancer, needs a portfolio of work. If it’s not clear, here is the reason: In pitching new clients (whomever they may be) you need a place you can point them to prove that you can deliver on what you say you can do.

When creating my first portfolio, as a writer, I had to start from scratch. I had been writing for many years, but I didn’t have clear examples of the kind of writing I wanted to do (at the time, pop culture writing.)

So how did I handle that?

I wrote my own pieces and created pages on my portfolio I could link to on the main landing page. Begged my friends with larger followings or bigger online publications to let me guest write pieces for them. I pitched my ass off to any place where I thought my storytelling would resonate. And, patiently waited for someone to say “yes.”

Point being, you don’t need to have a parcel of professional work to have a portfolio. No matter what you’re doing (dog trainer, floral artist, professional fire-eater) there are lots of ways to demonstrate your competency to potential clients and employers before you get your big break.

Things to consider when creating a freelance portfolio

  1. KISS – Keep it simple, stupid. Don’t create a portfolio with lots of moving parts that are going make it tough for people to navigate it.
  2. Put your best, and most recent, work up top – This is just straightforward. You want potential clients and employers to see your best work. You also want them to see your most recent work. This shows them you are working. And, will psychologically encourage them to consider you as a serious candidate.
  3. Make friends with a copyeditor – Have them review all the work and text you are plugging into your portfolio. Spelling, grammar errors, and typos make you look unprofessional. (My copyeditor is my Mom. Thanks, Mom!)
  4. Put your resume on a separate page on your portfolio – And, link it to the landing page. If you look at my page you can see that I link directly to my resume in the menu bar. This is so potential clients and employers can easily navigate to my resume without having to ask me for it.
  5. Make sure you put contact information on your portfolio – Um, duh.
  6. Consider making your portfolio password protected – If you are an online trickster who gets into trouble from time-to-time on social media (like me,) you may not want your portfolio to be found by trolls and people who hate you. ‘Nuff said.
  7. If you write a great blog, link to it – Um, duh. This is another example of your work.
  8. Get some good professional headshots taken – Think of these pictures as ones you’d like to see on the dust jacket of a book, should you write one. Post them on your About page, or with your resume. In the digital world of hiring the people you work with may want to see your pretty little face before contacting you for an interview or RFP (request for proposal.)
My very first “author’s” photo, courtesy of Julie Michelle

Shine Up Your Resume and References

This is a no-brainer. Just like any other job, you are going to need both a resume showing your past work. And, references who will say really nice things about how awesome you are.

Take the time to properly format your resume for both web optimization and for hard copy/PDF delivery. Contact your references and make sure they still are willing to say awesome things about you should a client or employer call them.

Find Out if You Need a Business License

This is SUPER important. If you are working in a state or municipality which requires you to have a business license you could get hit with massive fines if you don’t.

Also there are sometimes restrictions on where you can work. Some areas might not be zoned for home workers. In that case you need to find alternative space to work out of. If you are a 1099 worker, who has filed a W9 with the company you’re producing work for, you don’t need a business license.

Remote workers are often covered by a W4, having filed a W2 with their company. They don’t need to worry about this. It also makes tax time a lot more simple.

Business licenses can cost from $35 to $100 per year. You need to build into your yearly expenses to pay that fee in order to have your freedom to work freelance.

(Thankfully for me, Chicago doesn’t require business licenses for freelance writers. Nor do they have restrictions on where you can work. So I tippy-tap in my jammies from the corner of my bedroom which I have turned into an office. Lucky-ducky me.)

Save those dolla dolla bills

Save at Least 1 Month’s Rent/Expenses

This is just a suggestion. One that I have and have not followed at various points in my freelance career. When it was just me, living on my own, I was content to live paycheck-to-paycheck. Recently, in light of my divorce, I have been more focused on building out savings to protect my daughter and myself. Should we need to part ways with British Ex-Husband (who we plan to cohabitate with, but who knows if that will work?)

For me, a good method of savings is putting half of every paycheck in a savings account. I use the other half to pay bills. I do a lot of piece work right now (with one big client,) and I’ve been amazed at how quickly I’ve built up savings.

In considering your savings plan, you need to take everything into account. Don’t just save 1 month of rent, plug in all your other expenses. Car payment, insurance (of all kinds,) credit card debit, utilities, groceries, essential items (diapers, deodorant, etc.) Plus build in a little extra for emergencies, or so that you can occasionally order sushi from GrubHub.

It’s also helpful to look for ways to cut expenses. This will help you achieve a higher savings rate and get you to the point you can quit your 9-to-5 sooner. Check out Choose FI for great tips on how to track expenses and optimize savings.

Decide How You Want to Work Freelance

Do you want a home office? Or, do you want to work in a co-working space? Would you rather work from a coffee shop? Maybe from a beach in Tahiti?

All these are possible for the full-time freelancer. If your goal is to get to a point where you are working only for yourself, take time to consider what that would look like.

For me, that looks like having a home office based in Chicago, and having the ability to work while I travel with my daughter.

Pick your happy place and work hard to get to the place where you can work wherever you want to.

Do not pass go, do not collect $200

Look at Your Financial Structure

This section is SUPER SUPER DUPER important. You cannot just collect money and have that be the end. You need to look at how you’re going to structure your financial business so you can get the experienced help you are going to need.

We’re talking taxes, people.

If you are a 1099 worker or remote worker, this is a little more straightforward come tax time. Your employer will provide you with tax documents and you can file on a standard short form. 1099 workers do need to understand their tax liability and make sure they have saved money for the taxman in advance.

When you accept a blend of 1099 work and just straight up freelance work, you have more things to consider. Here is what I suggest:

  • Consult an accountant and find out, given your income, what your tax liability will be for the year.
  • Create a business savings account and pull money out of every paycheck to prepare for paying federal, state, and local income taxes at the end of each year. (Yes, this is an essential expense, build it into your budget)
  • Do some reading on what kind of deductions you can take to make your tax liability. For example: I have to buy a new computer this year. That is a tax deduction. Penelope is going to need a part-time nanny soon. That is a tax deduction. My British Ex-Husband and I are still legally married. We file jointly with me as head of household. He is a tax deduction.
  • Engage a professional to help you prepare your returns. This is time saving and reduces stress for you. There are lots of online services that can prepare and file your taxes for you. I prefer H&R Block. Over the years, they have maximized my filing and deductions so well that I usually end up getting a tax return. For a full time freelance worker that is like a cherry on top of ice cream.

However you approach it, you need to take time to consider your financials. Otherwise you’ll get on the IRS’s shitlist. And, trust me, you do not want that.

Agencies are your friends

Register With Staffing Agencies and Freelancer Websites

What, staffing agencies? Kate, we’re trying to get AWAY from working full time for big corporations, not leaning into finding another time-suck 9-to-5!

Wait. Staffing agencies aren’t the same as they used to be. They now encompass freelance and contract work. In fact I would say that 50% of my new work this year has come from a staffing agency. I recommend Creative Circle highly. They are very active and work their asses off to land you work. Also if you want to transition back into a full time job, they can help you with that, too.

As far as freelance websites, there are a lot out there, but only a few good ones. Here are the ones I recommend:

  1. Upwork
  2. Fiveverr
  3. Task Rabbit

There are way more out there, but these are the ones I have had the most success with in my time as a freelancer. If you want to check out the Top 20 Freelancer sites for 2020, click here.

We want a pitcher, not a belly itcher!

Pitch Your Ass Off

The reality is that when you are a beginning freelance worker, jobs aren’t going to come to you. You will have to PYAO (pitch your ass off) to get to those first paying jobs. This is why being on listing services is so important. (So you don’t have to cold-call potential clients, you can find companies that already have identified a need for a freelancer.)

On Upwork, they state that you likely will have to pitch between 5-10 times before you get your initial gig. That’s a lot of pitching.

In reality, I have found that you need to pitch way more than that to gain traction in your field. When I was just starting out, I spent all my spare time pitching. I think I averaged about 10 pitches a day.

How do I structure a pitch?

Pitching is the same as having a job interview. It’s making a case to an employer as to why you are the best choice for the job. There are lots of ways to pitch, but I have boiled down my style to a template that I can personalize for each pitch. Here’s it is:

  • Greeting and introduction – Say “hi” and introduce yourself in 1-2 sentences.
  • Create 3-4 bullet points highlighting your strengths/experience – Tell them about your achievements and your past work. Try to keep it to 2 sentences per bullet point
  • Identify the problem they are seeking to solve – This is important to illustrate your understanding of their needs and what they are looking for in a partner.
  • Tell them how you will solve their problem – Use your creative juices here, illustrate how you can solve their problem in a novel, innovative way.
  • Thank them for their time and provide a strong call to action (CTA) – Simple enough.
  • Provide a link to your portfolio – ‘Natch.
  • Add in your contact information – How else are they going to contact you?
  • Attach your resume and references – Duh.

This is how I do it. I find I have a 75% return rate on using this pitch template. Granted, I don’t get every one of those jobs, but I do at least get a response, a call back, or a RFP.

And, don’t limit yourself to corporate or businesses. If you have aspirational goals (like writing a book, or creating a IGTV series) find the contacts you need to get a foot in the door. One off the things I have always had going for me in my career, in general, I have never, ever been afraid to ask for what I want.

This is an attribute that you need to embrace. If you don’t ask for what you want, you won’t get it. Be assertive, and at times, aggressive. But, be kind, likeable, and professional. (Also never drink at networking events. It is a bad look. And, will cause you more problems than it’s worth to have that free beer or glass of rosé. Trust me.)

If you want some really great advice on pitching, check out this article on The Freelance Hustle.

They are the ones who give you the dolla dolla bills

Build Up a Few Reliable Freelance Clients

This is key to being able to leave the 9-5 grind. To consider yourself a full-time freelancer, you must be pulling in enough money to cover your monthly expenses. And, hopefully, thensome.

To achieve that financial goal, the freelance beginner needs to find at least 3 or 4 reliable clients that will provide you with monthly assignments. You may need to cobble together bits of income from here and there to make that happen at first. But, once you begin to gain credibility within your industry, you’ll be able to command higher rates, and (again) you’ll find people seeking you out for work.

Don’t ever screw over those reliable clients, though. They are who you’ll fall back on when times are lean. And, times will be lean. Especially in this Covid-19 fever dream we are living in.

Want to know a secret? My first real freelance client was eHow. They paid me between $15-$30 per 200 word article. Sometimes I’d bid on and write 10 articles in a day. This really helped me refine my how-to writing style. It also gave me a huge tutorial on researching topics I was not already an expert in, or interested in, and being able to write authoritatively on them.


Living your freelance dream is not out of reach. Just focus in on what your goal is, and approach it in an organized and deliberate way. You’ll get there eventually, little baby freelancer. I promise. Good luck!

Whatcha wanna know?


  1. What are the best freelance jobs for beginners in 2020? There are a wealth of opportunities out there for a beginning freelancer to take advantage of. Try being a virtual assistant, copywriter/copyeditor, professional resume/cover letter writer, handyman, dog walker, IT consultant, or wedding photographer. (If you have the skills.)
  2. Can freelance really provide me with full time income? It sure can! Take a look at CNBC’s list of the top paying freelance jobs of 2020. It’s incredible how much you can earn if you put the work into your career and education.
  3. What books do you recommend for the beginning freelancer? My So-Called Freelance Life by Michelle Goodman, The Hustle Manifesto by Ross Simmons, One Million Followers by Brendan Kane, and How to Win Friends and Influence People by Dale Carnegie. These books will teach you about the business side of being a freelance worker, give you a reality check about your freelance career, teach you how to market yourself, and how to effectively network. All important skills if you want to be a success in your freelance career.
  4. How often in the beginning of your freelance career did you have to take work that you didn’t want to? A couple of times, at least. Thankfully for me, I have a general interest in everything, so copywriting tasks are not that dull to me. I worked for a couple years as a virtual assistant. I didn’t love that, but it gave me the money I needed to be able to focus on my writing. (And, a lot of down time.)
  5. How long did it take you to make real money freelancing? A full 2 years. After my layoff in 2008, I had to rely on my savings and unemployment to pay the bills. I used this time to work on building a strong portfolio of work that demonstrated my capabilities. In 2010 I was finally offered my two first real money paying freelance jobs – as the editor of an online film review publication, and as a columnist/podcaster on an online pop-culture publication.
  6. Do I need to pay someone to design my portfolio? You can, if you have the money. But, in 2020 there are enough website builders that can assist you on creating a professional site that you don’t need to. Personally, I used WordPress Pro to host both my blog and my portfolio. Their backend is really easy to use, update, and customize. Plus there are a lot of plug-in tools that can make your life easier. It costs about $400 per year. Whereas, between buying a domain, paying for hosting, and paying a web designer $75/hour (minimum) to build your site and CMT… you’re going to spend a lot of money.
  7. Should I continue my education while freelancing? If you can afford so, yes. The more skills you are able to list on your resume, the more (and the better,) work you’ll be able to book. Check out sites like Coursera, Flatiron School, EdX (where you can go to Harvard for free,) and General for a variety of courses that can enhance your skill set and make you a more attractive freelance candidate.
  8. Isn’t this a Mommy Blog? Moms can be freelancers, too. Geez.

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