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What I’ve Learned In 15 Years As A Freelancer – 8 Business-Focused Lessons

Alice Sullivan is an award-winning ghostwriter, collaborator, and 11-time New York Times bestselling editor. A natural-born storyteller, she’s written 60 books and edited over 1,300 titles

Executive Contributor Alice Sullivan

It’s time to start a new series about the many lessons I’ve learned as a freelancer over the past (gulp) fifteen years. Of course, there are too many answers to put in one post. So, here’s the first of a two-part series illuminating what it looks like to work for myself. 

A woan holding a brown umbrella.

I’m starting out with my favorite business lessons. I’ll get to the fun, personal lessons later, but these are important, too! Plus, the business-related lessons help me optimize my time and talent, which, in turn, fund my lifestyle, my multiple hobbies, and my steady travel plans. 

1. Save 30% of your income for taxes

Man, do I wish someone told me this tip when I was a twenty-something venturing off on my own. (Frankly, someone may have told me, but have you tried advising a carefree twenty-something?) You may not need to spend the entire 30% on taxes. Hopefully, you’ll owe less! But saving this much ensures that you won’t be short when tax season rolls around. And if you have extra cash after paying your taxes, you can move it into your savings account, pay down a credit card, or reward yourself with a gift for being such a responsible human. 

Here’s why it really matters: Early in my freelance career, I did not have a system in place to help me save for taxes. I put money aside here and there, but largely spent most everything I made. One year, after paying my quarterly taxes, I discovered I owed another $16,000 that I didn’t have

For the next two years, I was on a payment plan with the IRS until it was paid back. Yuck! I never wanted to go through that again, so I started putting aside 30% for taxes and thankfully have never had this problem since. 

Now, if there’s leftover money (and there usually is), I invest it. Win-win. Which leads me to my next point: 

2. Invest as much as you comfortably can each quarter or each year

I’ve been lucky to have consistent income as a freelancer, but it’s always good to be prepared for a rainy day and for retirement. Freelancing allows incredible flexibility, and you might want to still be working well into–or even past–the typical retirement age. But you might also want to retire early instead.

So, if you have a surplus at the end of the quarter or year, max out your Roth, make sure you have an emergency fund, and then stash it in iBonds, the stock market, real estate, or a high-yield savings account. (I’m not a financial advisor, by the way, so please make sure you speak with one before making any financial decisions.) 

Yes, this may require you to be very intentional about your purchases and spending for a while. But you’ll thank me later. 

3. Set your own work schedule and stick to it

There’s no time clock to check in and out of when you’re a freelancer. The glory of freelancing is that you can work whenever you want and wherever you want. The pain of freelancing? You can work whenever you want and wherever you want. So you need to be your own benevolent boss and protect your time. 

When I first started freelancing, I had zero boundaries around my time. Yet I was repeatedly frustrated when clients would call me at 10 p.m. or 2 a.m. (yes, it happened once) or on the weekends to talk about ideas. Because I hadn’t decided on what my work hours would be, it never occurred to me that I didn’t have to answer calls, texts, or emails until the work week. Instead I prided myself on being someone who reacted almost immediately to every form of communication. And that soon led to resentment.

Once I began including information on my contracts about my work hours and how I prefer to communicate with clients, it was easier to maintain boundaries. It was also easier to help me separate myself from my work when I was spending time with family and friends. 

Set work hours that work for you and that are generally accepted by your clients. You may have to gently remind your clients now and then that you don’t answer emails on the weekends, or that you only take scheduled phone calls. But it gets easier every time you speak up for yourself. 

Protect your time and energy so you can give your best while you’re working, and so you can fully relax when you’re not. 

4. Create a fail-proof record-keeping system for your work files

Let me tell you a not-so-fun story about a time I royally screwed up. I realize it’s not flattering to admit I’ve made some big mistakes in my career, but who hasn’t? The mistakes have always provided helpful lessons and alternative ways of doing things. 

Several years ago, I was working on a mammoth project that was laid out in three parts. And each part had 10-15 chapters. The problem was that I didn’t have a great process in place to ensure I marked the most recent versions of each chapter, and the client would frequently revise chapters, sometimes sending several versions of the same chapter in the same day. Needless to say, when I put the first full draft together in one document, several of the chapters were the older versions and not the newest ones. Not good. I was let go from the project and felt terrible about my errors. The silver lining is that I created a solid system of record-keeping that’s kept me on track ever since. 

It’s easy to lose track of files if you’re in a busy season or if there are a huge amount of files for a single project. But not having a fail-proof system in place only creates more work for you in the future, so come up with a plan now. Plus, if you’re in the writing world like me, version control—knowing which version is the most up-to-date and ensuring that you and your client are working on the same document—is crucial. 

5. You can’t be an expert in everything! Hire the best to help you grow and manage your business

In my first few years as a freelancer, I wore multiple hats because I had to. But once I was consistent with my income, I reached out to experts to help in the various areas where I was not an expert. 

As a freelancer or contractor, you might need help with legal, marketing, your website, social media, sales, cleaning your office, or meal prep and delivery. Outsourcing tasks you’re not great at, trained for, or in love with lets you focus on what you excel at.

My first big expenses as a freelancer were hiring someone to create my first website, and hiring a lawyer to create a contract for me. If I recall correctly, it cost $500 to secure my domain name, my first website cost $1,500, and my first work-for-hire contract from my lawyer cost $500. Those were huge expenses at the time. But I made all that back and more upon signing a new writing client. 

6. Research what your peers charge and adjust your rates accordingly

In a recent post for Brainz magazine, I outlined how I was eight years into freelance life, when I realized I was asking for peasant’s wages when my peers were charging far more. Coming from a corporate work environment, I’d already gotten my proverbial hand slapped twice by HR for discussing my salary when a friend asked what I was being paid. 

I know now that HR shouldn’t have called me in because there’s a law in place that prohibits companies from punishing employees for discussing wages. But I had no idea that law existed. And I was scared to lose my job. 

When I left the corporate world, it never occurred to me that I could and should freely have conversations about rates and negotiations with fellow freelancers. Instead, eight years after I was on my own, I offhandedly asked my lawyer if I was on par with other writers when she told me I was charging less than half of what my peers–some with much less experience–were charging. That was a huge turning point in my career. And I’ve been a huge advocate for financial transparency ever since. 

Transparency in pay helps everyone, so ask around about rates and do your research. Practice quoting your higher price out loud to a friend, or even into a mirror, and not blinking until you can imagine your potential client answering in a positive way.

7. Give back in terms of your knowledge and encouragement to those who are earlier in their careers

I’d love to say I’m “self-made,” but the truth is many people have helped me along the way by providing knowledge, mentorship, encouragement, and connections. Once I was established as a freelancer, others began reaching out to me to learn more about how I’d set up my business and how I’d achieved a level of success. I’ve since participated in multiple mentorship programs to help new writers and creatives, and I frequently give advice to those who are looking to make a career change. I believe sharing your knowledge is one of the most impactful ways to help others. 

Financial gifts also make a huge difference. No matter your line of work, there are bound to be conferences, courses, or other events that you can contribute to, in order to help your peers grow in their careers. Giving back helps you say thank you to the folks who helped you get where you are today. 

8. Create a system to follow up with your leads, but don’t beg anyone to work with you

What’s the longest amount of time you’ve courted a business lead and it paid off? For me, it was seven years. That’s not typical for me, in case you’re wondering. Most of the time, I’ll follow up with a potential client for a few months. If there’s zero response, I eventually stop messaging them as often. However, a dear friend of mine makes it a rule to follow-up with someone until they say yes (or no), or until they die. And she’s gotten several fantastic clients after years of consistent contact. So, it’s all about your own comfort level. 

People are busy and forgetful, and nudging them through email can sometimes help you land a client, especially if you’re providing useful information and keeping up with their lives. That said, after a few months of silence, I have a hard time continuing to pursue clients with regularity. I may check back in with them every quarter or every six months, but if they don’t need my services any longer or don’t want to work with me, I accept it and move on. 

Your time is valuable, and so are your services. Not every client is the right client for you and that’s okay. 

In the next article, I’ll talk about the more nebulous aspects of being your own boss: self-care in its many forms, and why you should view yourself as your most precious commodity!  


Alice Sullivan, Ghostwriter

Alice Sullivan is an award-winning ghostwriter, collaborator, and 11-time New York Times bestselling editor. A natural-born storyteller, she’s written 60 books and edited over 1,300 titles. She specializes in nonfiction—specifically memoir, self-help, and personal growth. She helps clients identify their goals and messages while creating engaging content to connect with their target markets. Her favorite projects are those that challenge her point of view and expand her knowledge.



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