Tips for The New Freelancer: What to Do Before You Quit Your Day Job
Disclaimer: This post provides anecdotal advice based on my personal experience. This post is neither financial nor legal advice. Before making any major decisions about your income or starting a business, consult licensed professionals.So you Wanna be Your Own Boss?
What could be better than working on your own terms? Many people choose freelance work for the flexibility of working when and where they want. Whether it's managing childcare, pursuing passions, embracing a nomadic lifestyle, or simply avoiding the challenges of traditional employment, freelancing has its appeal.
But while freelancing offers freedom, it has its challenges. I’ve been freelancing for over a decade, and while it's been the right choice for me, it’s not always easy, quick, or guaranteed. In this post, I’ll share insights from my own journey, including the basics of freelancing, types of jobs available, key differences between freelancing and traditional employment, and tips for getting started. Everyone’s journey is different, but this guide will help you prepare for what lies ahead.
Freelancing Basics
So, what is freelancing? What’s it look like? Who can do it?
Freelance work is selling your services to clients and working for them as a contractor. You are not an employee of your clients, which means you don’t have to negotiate with them over things like pay and benefits. They are not your employer, so they can end your contract anytime. You are not their employee so you don’t have to do any annoying team building or work specific hours. They are not your employer, so they don’t have to train you or provide the tech needed to do your work.
There are benefits and risks for both freelancers and clients.
Freelancers do all sorts of jobs: bookkeeping, digital marketing, graphic design, content and ghostwriting, video editing and animation, music production… If you've got a skill, chances are you can monetize it as a freelancer! The fun thing about freelance is that you’re often able to work across industries and, once established, can pick and choose who you work with.
Something many people may not realize, is that this type of work can be incredibly lucrative for people who do not typically thrive in the traditional workplace.
I’ll use myself as an example: I get bored very easily, but I love to learn. When I started working for a digital marketing firm, writing content for clients across myriad industries, I was excited, quick and creative. After year three I was bored to tears. In addition to not learning anything new, I was also dealing with things like pointless check in meetings (we all worked independently), status reports that shared the same information as the pointless check in meetings and a few colleagues I didn’t really like.
Sorry, this is the truth of traditional employment.
When freelancing, I purposely structure my work to be one or two long-term clients that I really like and then shorter-term projects. This way I have great relationships with people I enjoy, but I also get two consistent dopamine hits: learning all about a new client’s needs and successfully completing projects.
Freelancing allows people like me (Pisces? I wonder if there’s a direct correlation!) to thrive in our need for the new and super-short attention spans. Am I a bad employee? No. Do I work better on my own and with shorter-term relationships? Yes!
Freelancing isn’t just for those who crave novelty.
Some freelancers thrive on the ability to create a structured, predictable schedule and work independently without the oversight of a traditional boss. For example, if you're someone who likes to follow a routine, freelancing allows you to set your own consistent hours and create the perfect work environment for your needs. This can be a great fit for people who prefer to focus deeply on a few long-term clients or projects, rather than constantly juggling new ones.
Unlike the fast-paced need for new experiences that I enjoy, some freelancers find fulfillment in the stability of predictable workflows and ongoing client relationships. The key is identifying how you work best and then structuring your freelance career to match that style.
Understanding how you work best is one of the most important things to figure out when starting your freelance journey.
Are You Ready to Start Freelancing?
So, how do people start freelancing? Some dive right into it. Others are more hesitant. This isn’t legal or financial advice, but it’s great advice for life: make sure you fully understand what freelancing is and how it works before quitting your job.
If you’ve never thought about freelancing, my checklist is a great way to start understanding the preparation that goes into it. If you’re anywhere else in your journey, this checklist is a great way to understand what you might still need to do.
You Need to Talk to a Professional About Money
Freelancing income is different from income earned through traditional employment. For example, if you currently have health insurance provided by your employer, this is a new, big expense you have to consider.
Also, the belief that you get to keep more of your money is a big myth. As of this blog post, the federal self-employment tax is just under 15.5%. So, every $100 you earn is really about $84.50.
A mistake I hear a lot of people make is thinking they just have to “make the same amount.” Sadly, that math won’t math.
If you currently make $55,000/year before taxes, you’ll need to make about $63,250 to make home that same amount.
Understanding the math of what you need to earn is vital to making any major decisions, including starting to freelance. Be sure to talk to a licensed accountant who works with self-employed professionals.
Building Long-Term Client Relationships
The hardest part of freelancing is finding enough long-term clients to provide consistent revenue. Read that again, write it on a post-it, and say it a few times a day.
But finding those clients is only the beginning. Once you’ve signed them, maintaining the relationship is key to building consistent revenue. Here are a few strategies to help you build and manage long-term client relationships:
Set Clear Expectations from the Start: Make sure you and your client are on the same page about deliverables, timelines, and communication preferences. Having this clarity prevents misunderstandings later and sets a professional tone from day one.
Stay Proactive with Communication: Regular check-ins with your clients, even if it’s just to update them on your progress, show that you’re on top of things. Clients appreciate not having to chase after you for updates. A quick weekly email or call can make a big difference in trust-building.
Go Above and Beyond: Whenever possible, deliver more than expected. This could be in the form of extra attention to detail, offering advice, or suggesting improvements they might not have thought about. Clients notice when you’re invested in their success, and this often leads to longer contracts or referrals.
Be Flexible but Firm: Sometimes clients will ask for more than what was agreed upon. Being flexible can be a good way to build goodwill, but don’t be afraid to set boundaries and ask for additional compensation when the scope of work changes.
Ask for Feedback: At the end of a project or milestone, ask your client for feedback. Not only does this help you improve, but it also shows the client that you’re committed to delivering the best service possible.
Show Appreciation: It’s easy to get caught up in the work, but don’t forget to show appreciation for your clients. A simple thank-you note or a holiday card can go a long way in keeping the relationship strong.
This is one of the many reasons why hastily quitting a job to freelance is a terrible idea. It takes a long time to find, sign and build a long-term relationship with a client.
This is where most of your efforts will focus in the beginning, and you should do this while you still have the security of regular income.
The Best Place to Start Freelancing and Other Freelance Client-Acquisition Tips
When I started freelancing, I didn’t know what I was doing. Don’t make the same mistake I did! Rather than research my options, or find a mentor, I looked for “freelance writing jobs” and ended up in the hell that is content mills.
Content mills are online portals where you get assigned writing jobs. If those jobs are approved, you get paid literal pennies. But what if the writing is not approved? You’ve spent that time working for free (I’m convinced they still use your content).
The best place to start your freelancing career is Upwork. Back when I started, they were still called elance and they were and are the safest place to find consistent work. I have coached multiple friends on how to get started on Upwork because it is a reputable, safe platform where you can earn decent money, have an advocate, they do all the tax reporting for you (praise the Universe!) and there are safeguards to ensure you get your money.
Upwork is reviews-based so while it can take time to get that first job, once you do, and once you get a great rating, it gets easier. This also allows you to start building a portfolio! Upwork makes cute graphics when you get a review that you can share on social media, or your freelance website, to help you gain clients off of the site, too.
My best advice is to get on Upwork, learn how to use it, and make sure you knock every job out of the park. If someone approaches you outside of Upwork, you can bring them onto the platform, giving you all of the protections you need without the stress of having to develop a contract (or the cost of paying an attorney to do this for you).
Freelancing Tips for Planning Your Business
I’ve said it before and I’ll say it again: there is a lot of preparation that goes into freelancing.
Here’s some tips to get you started so you are more likely to succeed.
Define your services. What problems do you solve for others? Do you create logos that attract leads? Do you organize new parents' homes? Do you build e-commerce sites? Whatever you do, you have to be able to pitch it quickly and well.
Create boundaries. Some clients require a lot of time and attention. Others want you to just run with what they give you and show them when you’re done. For this reason, you need to think about your boundaries. We’re not talking about personal time or ethical boundaries here: this all comes down to money. My most basic services packages do not include regular phone calls. They include an initial call and they include a call after deliverables are received so that me and the client can review and ask questions. If I have a client I can tell is going to need a lot of one-on-one time, I have an add on for phone calls. Remember: the time you spend doing extra for a client is lost revenue. This is not to say you shouldn’t go above and beyond. It is to say that you should make sure you’re compensated for extra work.
Determine your pay structure. Unpopular approach: I have an hourly rate. In addition to flat-fee projects, I have clients that pay me based on time. This is especially true of my longer-term clients for whom I do repetitive work. For example, if I am adding products to an ecommerce website, there’s not really an easy way to price that. The solution? An hourly rate.
Hello? Is There Anybody Out There?
No matter how great it is to not have to be in an office, or on your company’s internal messaging system, or in the breakroom with the guy who spills coffee and doesn’t wipe it up EVERY DAY, the lack of people does have a downside.
I have a rich social life. I go out at least three nights a week. But I don't have colleagues. I don’t have people whose office I can go visit to run questions by. I don’t have someone a desk over I can vent to.
I also don’t have guaranteed work: there’s no manager assigning me work.
For this reason, I find networking vital.
We don’t have a local freelance group, but I am part of my local Chamber and our downtown business owners' organization. Meeting with other professionals throughout my community has enabled me to have a network of like-minded, smart, experienced people I know I can call any time. And they know they can call me.
These folks are also often the first to hire me or recommend me to others. And, let’s face it, referrals are the lifeblood of freelancing. Whenever someone calls and has already heard that I’m great to work with, it brings me great relief.
How to Start Building Your Freelance Network
If you’re new to freelancing or working in a region without a strong freelance community, building a network can feel daunting. But it’s essential for long-term success, especially when word-of-mouth referrals can become one of your best sources of new clients. Here are some practical ways to start building your network:
Join Local Business or Industry Groups: Whether you’re in a big city or a smaller town, look for local business organizations like your Chamber of Commerce or industry-specific groups. If your area doesn’t have a freelance-specific group, join broader organizations where your clients might be. For example, graphic designers might join marketing groups, while writers could connect with publishing circles.
Leverage Online Communities: If local groups aren’t an option, you can still build connections online. LinkedIn is a powerful platform for freelancers to network, especially by joining industry-specific groups or following companies you want to work with. Additionally, platforms like Reddit, Facebook groups, and niche freelance communities like Freelancers Union can be great places to connect with others in your industry.
Attend Networking Events or Conferences: Even if you’re not the most social person, attending in-person or virtual events related to your industry can give you face-to-face time with potential clients or fellow freelancers. For freelancers working remotely or in isolated areas, virtual conferences and webinars have become a great way to build relationships.
Collaborate with Other Freelancers: Sometimes, your best network will come from working alongside other freelancers. Whether it’s through referrals or project collaborations, freelancers can help each other land clients or share advice. Consider partnering with freelancers in complementary fields—for instance, a copywriter and web designer can team up to offer package deals.
Give Before You Ask: One of the best ways to build a strong network is to give value before asking for anything in return. Offer advice, make introductions, or share resources with others in your community. People are more likely to recommend or hire you when they see that you’re generous with your knowledge and time.
Sure, it is a two-way street. When freelancers I know need an accountant, Realtor, caterer or anything else, I refer them to the people in my network. And I’m happy to do this. I have a great network of awesome, skilled people I’m proud to send others to because I know the work will be impeccable. Building a network is fundamental to striking out on your own.
Freelancing is not Easy or Guaranteed
There are times when no one is calling. In winter, from about mid-November through March, my long-term clients are experiencing a slow season and I’m not getting any new work.
It’s discouraging. It can be scary to not have money coming in.
The best way to manage this annual terror is to use it to work on your own business, because your freelance work is a business.
I try to plan a trip during this time to keep my spirits up and distract myself from the flat trendline in my bank account.
But the most important thing is to increase my focus on my own business. During my normal times I spend two hours every morning in deep work on my business. In slow times, I add to this.
Downtime is great for:
Reviewing your website and Upwork profile and updating it. Have you added any skills, completed a project that should be in your portfolio, or won any awards you could update your profiles with?
Cleaning up. Find and organize your orphaned files, go through that stack of mail you keep saying you’ll get to later, unsubscribe from the newsletters that sit unopened in your inbox.
Content Creation. All those great ideas you’ve put on a list for “when I have time to film videos”? Film them now! Not only will you have new content but you’ll also get a thrill from crossing them off the list!
Freelancing is Not Easy or Guaranteed
There are times when no one is calling. In winter, from about mid-November through March, my long-term clients experience a slow season, and I’m not getting any new work.
It’s discouraging. It can be scary to not have money coming in.
The best way to manage this annual terror is to use it to work on your own business, because your freelance work is a business. Here are a few strategies to help you manage slow periods and make the most of your downtime:
Diversify Your Income Streams: Relying on just one or two sources of income can be risky for freelancers. During slow periods, consider exploring other ways to generate income. This could mean offering a new service, selling digital products (like templates, e-books, or guides), or branching into passive income streams like affiliate marketing or creating an online course. Having multiple income streams can help balance the slower months.
Skill Development and Training: When work is slow, use the time to invest in yourself. Take online courses, attend webinars, or read up on industry trends. Adding new skills to your repertoire not only helps you offer more value to your clients but also keeps you competitive in the ever-changing freelance market.
Update Your Portfolio and Marketing Materials: Downtime is perfect for refreshing your website, updating your portfolio with recent projects, or refining your marketing strategy. Use this period to optimize your LinkedIn profile, enhance your SEO, or create new content like blogs or social media posts to attract future clients.
Reach Out to Past Clients: Don’t wait for work to come to you. Slow periods are a good time to check in with past clients to see if they need any help. Often, they’ll have a new project you can assist with, or they may recommend you to someone in their network.
Use Downtime to Plan for the Future: Slow seasons don’t last forever, but they can be a great time to strategize. Take this time to review your business goals, make financial plans, or map out projects you want to focus on when things pick up again. This will keep you prepared and motivated when business gets busier.
Stay Fresh, Cheesebags
Is something taking longer than it should on the regular? I thought my blogging schedule, for example, was going to be perfect. Turns out the writing process takes me longer than I expected. Because of this, I recently changed up my routine to make sure I have 3 writing days in my 13-day cycle. .I replaced “admin” which doesn’t need a whole two hours every thirteen days. I replaced “follow-ups” and incorporated those more organically.
Take time, regularly, to assess if your workflow and routines are actually working and amend them as necessary.
Freelance is Rewarding but Understand the Risks
Going freelance is one of the best decisions I’ve made for myself and I do think it’s the right choice for many people finding themselves unfulfilled in traditional work. Understanding what goes into it and carefully preparing, are the keys to a successful freelance career. If you’d like help assessing your readiness, download and use the checklist. Or, better, let’s jump on a call and see if you’re at a place where coaching could help you take the plunge!
