Why Most People Fail at Freelancing (And How to Know If You’re Different)

Most people fail at freelancing not because they lack talent, but because they are not ready for the uncertainty, self-discipline and business skills that come with working for yourself. In this episode, Al Calder weighs the freedom of freelancing against feast-or-famine income, managing your own taxes and time, and the traits that help freelancers succeed. If you can handle the ups and downs, set boundaries and keep learning, freelancing can give you the freedom to design a life you love.

Welcome to The Freelance Insider Show!

Today we’re taking a deep dive into why most people fail at freelancing. We’ll look at the ups and downs of being your own boss, setting your own hours, and working from the comfort of your backyard, but also the not so glamorous side of things, like the feast or famine cycle and the potential for burnout.

If you’re still dreaming of working from home in your pj’s, this one’s for you!

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What You’ll Learn in This Episode

• The real upsides of freelancing: flexibility, freedom to choose your hours and where you work, project variety, and being your own boss.
• The hidden downsides: inconsistent income, no paid vacation or employer benefits, and the challenge of keeping work and life in balance.
• The traits successful freelancers need: self-discipline, resilience, comfort with financial uncertainty, and a habit of continuous learning.
• How to manage money and find clients: building a savings cushion, tracking income and expenses, and building your own client base beyond Upwork and Fiverr.
• The questions to ask before you leap: whether you can handle the risk and the loneliness, and whether you have a plan for slow periods and a safety net.

Episode Highlights:

• Broad overview of the upsides and downsides
• Essential traits of a freelancer
• Setting boundaries as a freelancer
• Money Management
• Finding Clients
• The need for continuous learning
• Networking

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Full Episode Transcript

Welcome

Al Calder: Welcome to Freelance Under the Hood, the podcast where we help you work from anywhere and design a life that you love. I’m your host, Al Calder, and today we’re answering a big question: is freelancing right for you? In this first episode, we’ll explore the exciting ups and the challenging downs of freelancing, and help you decide if it’s the right path for you.

So, what exactly is freelancing? It’s a way of working where you’re self-employed, offering your skills and services to clients on a project-by-project basis. It’s a growing trend, and more and more people are ditching the traditional 9-to-5 to work for themselves. But is it all that it’s cracked up to be? Let’s dive in, get under the hood, and find out.

What are the upsides of freelancing? Let’s explore the freedom and get under the hood of freelancing. The biggest draw is flexibility and freedom. You get to choose your own hours, you can work from anywhere with a Wi-Fi connection, and you can be your own boss, which means you set the direction of your work and your career.

Another big draw is variety. As a freelancer, you get to work on different projects with different clients. It keeps things interesting and allows you to build a diverse, versatile set of skills.

But there’s more to it. That freedom isn’t free. There’s a lot of responsibility that comes with it. You’re also in charge of your own taxes, your own insurance, and your own retirement savings. And let’s not forget, there’s no paid vacation days.

So, whether freelancing is right for you depends on how you feel about that. There are no guarantees here. You’ll never know when the next paycheck is coming, and it can sometimes feel like a rollercoaster ride.

Freedom, Appeal and Hidden Costs

Al Calder: Let’s start by talking about the freedom of freelancing. As a freelancer, you have the power to choose when and where you work. How many hours you work and who you work with. No one to tell you what to do. That’s a very liberating feeling.

Freelancing provides a great deal of flexibility and autonomy, but also a certain amount of pressure and responsibility. There’s no one to hold you accountable or check in on you. When you wake up in the morning, there is no boss to answer to. So it’s up to you to make sure you’re productive and stay on track.

Another thing to think about is how you manage your own time. You need to be disciplined with your time and prioritize what needs to be done. You can’t just go out and grab a coffee before you start working. It’s important to treat your freelance work like a job, not like a hobby.

One of the hidden costs of freelancing is work-life balance. When you’re your own boss, you’re in charge of setting the boundaries between work and family. You can work all day and night, or you can choose to limit your hours and spend time with your family. Some people take freelancing way too far, or they treat it like a hobby and they don’t respect their clients.

Traits, Confidence and Boundaries

Al Calder: Now, let’s talk about the critical skills that a freelancer needs. To be a successful freelancer, you need to be disciplined in many ways. Ironically, you need to be more disciplined than if you were working in an office environment. You need to be self-disciplined because no one is watching over your shoulder. You need to be able to motivate yourself and focus on the task at hand. That’s often easier said than done.

Another key trait is resilience. You need to be able to bounce back from setbacks and keep moving forward, no matter what. Freelancing is not always easy. It’s not a straight line. There are ups and downs, and it can feel like an emotional rollercoaster.

The next trait is trying to get comfortable with financial uncertainty. You need to be okay with not knowing where your next paycheck will come from. Let’s face it, freelancing is a business and in business, you can be rich one day and poor the next. But if you’ve got the stomach for it, you can build a lifestyle that gives you freedom and flexibility.

Last but not least, the ability to keep learning. Freelancing is not a job, it’s a lifestyle. You constantly need to learn and improve your skills in order to stay competitive and relevant in a fast-changing world of work.

Setting boundaries with clients is also essential. You need to know when to say no, and when to say yes, and how to set expectations around deadlines, costs and scheduling, so that your clients understand what you can do within these constraints.

An important concept to learn is the balance between the supply side and the demand side of your business. You need to create work, but you also need to keep clients happy. You need to make sure you’ve got a lot of work to do, both in the near term and in the long term.

Managing Money and Finding Clients

Al Calder: Another thing that’s really important is how you know whether freelancing is right for you. You’ll have to think about it. Do you have the self-discipline to make it work? Are you comfortable dealing with the ups and downs, both financially and emotionally?

The freelancing life isn’t for the faint of heart, but it can be an incredibly rewarding career. If you are open to learning, trying new things and taking calculated risks, this lifestyle might be for you.

Let’s explore the first question: can you handle the financial uncertainty? One of the biggest challenges as a freelancer is the uncertainty of income. Some months you might earn a lot, and then the next month you might earn nothing.

It’s really important to have a savings cushion that will keep you going for a while. You need to be prepared for those lean months, and you need to have a plan for how to deal with them. What about those slower periods? You can use them to learn new skills, to try new ideas or to rest and recharge your batteries.

One of the key things you need to learn is how to track your finances. You need to set up an invoicing system and keep good records of everything you buy and sell so that it’s easy to do taxes at the end of the year. There are lots of great tools out there like QuickBooks, FreshBooks and Wave to help you manage your finances and make them a little less stressful.

Another area that’s really important is finding clients. You can start by joining freelancing platforms like Upwork and Fiverr, but remember that while these are great places to find work, you’ll be competing with a lot of freelancers for the same jobs. Like any marketplace, you might not get the best-paid jobs this way, so it’s worth having a few strategies in place.

The key to building a sustainable business is to build your own client base, rather than relying on a platform. You need to find a way to connect directly with companies that need your skills. It takes time to build trust and build a reputation, but it’s worth it for the stability it provides and the higher-paying clients.

Learning, Networking and the Bigger Picture

Al Calder: What about learning? As a freelancer, you need to be constantly learning and staying ahead of the curve. Invest in courses and training programs that can help accelerate your career, but also take the time to learn from people who are further ahead in their journey than you are.

Networking is another thing you need to work on. People who know you and trust your work are more likely to help you find new clients, but you need to network with them first. You need to create an online presence too, with a portfolio of your work so that people can see what you can do.

It’s important to remember this: networking is not something you do once and then forget about. You’ve got to actively reach out to others and stay connected, whether that’s through LinkedIn, social media or local meetups. When it’s done right, networking is a great way to build your credibility and your client base.

The freedom that freelancing gives you is really exciting, but you also need to understand the business side of it. It’s not all about doing the work that you love — you also need to manage your time, your money and your clients. You need to think about marketing, accounting and customer service.

Questions Before Taking the Leap

Al Calder: Let’s try something with you now. Ask yourself these tough questions before you jump in. Sit down and think about whether freelancing is the right thing for you and for your family.

Are you willing to give up a stable job and step into the unknown? Are you comfortable with the risk of freelancing and the potential loneliness that can come with it? Do you have a plan for dealing with those slow periods, and building a safety net for yourself and your family?

Are you ready to make a real commitment to your business? You’ll be spending a lot of time learning, working on your skills and maintaining a healthy work-life balance. You’ll need to prioritize these things, or they will suffer.

If this seems daunting to you, that’s okay. Freelancing can be a wild ride, but it can also be an amazing experience. Just remember, if you choose this path, you’ll need to put yourself out there and stay positive, even when things get tough.

Look, the best thing about freelancing is that if you have the right mindset and you’re willing to put in the work, you have the freedom to design your own life. There are no limits to what you can achieve if you set yourself up properly.

If you figure out that the online course route doesn’t feel right for you, perhaps there’s another type of business you can think of that could be a better fit. For example, you could create a freelance business that offers services on a regular basis, like writing content, designing websites, presenting on webinars or working as a virtual assistant.

If you’re making the leap, I wish you all the best of luck, and if you liked this episode, I’d love for you to subscribe to this podcast, leave a review and share it with a friend. Your support means a lot to us because we love this community so much, and we want to help more and more people find the freedom for themselves.

Handling Rejection and Deciding

Al Calder: And that is our show for today. I’d like to remind you to please subscribe to the show. Thank you for joining us on the show. Don’t forget to like this video and subscribe — it would mean the world to us. We’ll see you next time.

Ready to take the next step? Download the free Freelance Reset Checklist at remoteofficeworld.com and subscribe to The Freelance Insider Show so you never miss an episode.