The image of a person with their laptop sitting on a beach with a Piña Colada by their side has become the poster child of “freelancing”.

The promise of ultimate freedom and working anywhere and anytime you want is just so appealing, causing many to jump in without carefully thinking about it.

The truth is, freelancing is far from easy. Contrary to what most people think, signing up on Upwork and sending tons of applications a day will not do the trick.

I think what makes freelancing harder for some people is a two-pronged issue:

• Some people aren’t built to freelance.
• Some people aren’t fully equipped to freelance.

Let’s talk about these in more detail.

Is freelancing right for you?

Freelancing is not a ticket to an easy life. It comes with perks, but it also has pitfalls.

Some people can handle these well while some can not. How hard freelancing is for you may depend on your personality, working style, and how well you tolerate uncertainty.

These are some of the most difficult parts of being a freelance developer:

Too much work or no work at all

Freelancing is often a life of extremes. There’s rarely “in-between”. Either you’ll be buried in so much work you have no time for anything else, or you’re totally out of projects so you can’t afford a nice meal in a restaurant.

There is no sense of security

Several factors contribute to this. Finding clients is hard, the competition is fierce, and it’s hard to stand out sometimes.

The uncertainty puts freelancers into survival mode. You’re afraid to turn down projects even though you have too many already because you’re afraid of letting opportunities go.

Other times, you’ll worry about rent because you have literally nothing going on.

It’s almost like a never-ending worry about whether you will get a project again or if you’ll have to go back to your 9-to-5 job.

Achieving a work-life balance is hard

It’s the ultimate irony of freelancing. You jump into it thinking that you’ll finally have more free time, but in reality, it gets harder to switch off and take a break.

It might be a Saturday morning and you receive an email from a potential client asking to see your portfolio. Will you pass the chance up? The inability to let things wait stems from the lack of security.

Since you’re working from home (or anywhere), the line between work and life gets blurred and you end up mixing the two. Plus, you don’t have a team to help you.

Suddenly you’re an accountant, administrative staff, networker, scheduler, marketer, salesperson, project manager – and you have to do everything on your own.

Managing yourself is also hard

Freelancers don’t have a boss to keep tabs on them, so getting tasks done on time requires a greater deal of self-control. You’ll never know how tempting a bed is in a cozy rainy afternoon until you have to choose between snuggling up or finishing a task.

And because you have no website access restrictions, that “quick check” of your Instagram feed can quickly turn into a two-hour scrolling and watching cute dog videos. And that new Netflix series seems so interesting…

Some days you’re going to be filled with productivity manna from the skies, but some days you won’t. It’s just a part of freelancing.

Difficult client relationships

Although there are clients who are a dream to work with, some are just a nightmare.

Freelancers often have to deal with objections and clients who never know what they want (“I’ll know what I want when I see it”), demand for unpaid revisions, and always seem to find an excuse to delay your payments. Or worse, some don’t pay at all.

It gets lonely

Never having to deal with office drama ever again is one of the perks of freelancing. But when your tasks are piling up and your stress levels are through the roof, sometimes you can’t help but miss the quick chats with your officemates while you’re making coffee in the pantry. Extroverted people often find the isolation more challenging than introverts.


Wait, I have to do taxes?! Yep, freelancers have to file their taxes. Unlike employees who enjoy deducted taxes, freelancers either have to do it themselves or hire an accountant. Either way, taxes are a necessary evil for freelancers and no one likes to do it.

How to succeed as a freelancer

As I said before, another reason why freelancing is so hard for most people is that they aren’t fully equipped.

Although there isn’t a life-hack that can guarantee your success, there are things you can do to start off on the right foot and increase your chances of succeeding.

Set a realistic goal

You have to know what you’re aiming for. These goals, if they’re compelling and important enough for you, will help you overcome obstacles, even the ones we’ve talked about before.

Write down on paper the things that you want to achieve as a freelancer. How much do you want to make? What kind of career do you want to build? What kinds of projects do you want to work on?

Plan a good strategy

“If you fail to plan, you’re planning to fail.”

It’s the same with freelancing.

If you don’t plan effectively, you’re going in blind, and you’ll bump into obstacles that could easily have been avoided had you seen them ahead.

Your strategy should answer the following questions:

• What services will you offer?
What is your niche?
• How much will you charge?
• How do you plan on marketing and/or advertising your services?
• How can you build your credibility?

To come up with a good strategy, you have to research. This is where the equipping part comes in. Read books, listen to podcasts, read blogs, watch YouTube videos, and maybe even buy a course if you think you need it.

The key is to find out how successful freelancers did it. What was their strategy? What worked and didn’t work for them? Then incorporate those into your strategy.

A great place to start is my freelancing bundle where I discuss in more detail the steps you can take to build a successful freelance web developing business.

Stay focused and have grit

As you start freelancing, it’s easy to get sidetracked with minor details or lose heart when you get rejected over and over again. But there’s no other way to succeed in freelancing than to keep going.

You have to have grit and self-discipline to achieve your goals. When times get tough, go back to your goals and remind yourself why you even started in the first place.

Learn, and learn some more

I can’t emphasize the importance of learning enough. Not only will it help you create a good strategy, but it will also help you shift your gears if something is not working. If you notice that your marketing strategy isn’t working, learn more tips and techniques from successful freelancers.

Learning new skills can also supplement your income and maybe even present new, more profitable opportunities. Staying on top of your niche and industry will also give you an edge over your competitors.

Constant learning will also give you an attitude of humility because you know that you don’t know everything yet.

Build your business skills

Freelancing is a business. The earlier you embrace that, the better. Running a business may seem overwhelming, but it can be learned.

The good news is business skills aren’t learned by getting a diploma or enrolling in a business course. They're best learned by experience.

As you build your freelancing business, you will hone your business skills, which will in turn make it easier for you to accelerate your growth. You will learn how to market yourself effectively, how to write amazing proposals, how to connect with people, and even how to deal with procrastination and stress.

In other words, if you maintain an attitude of grit and constant learning, you will have a high chance of succeeding.

Build the right kind of revenue

There are two kinds of income that I like most: recurring and passive.

Recurring income is the perfect solution to the feast-and-famine cycle of freelancing. Instead of charging a one-time fee, what if you could charge recurring monthly fees?

This can be done with a bit of strategizing. What kinds of services do your clients need monthly? Which of these services can you provide to them?

Let’s say you are a freelance web developer. Your forte is websites. There are all sorts of website services that people always need, such as maintenance, security, SEO, advertising, and content production.

Once you come up with a list of monthly services that you can offer, create at least three monthly packages.

This way, instead of charging a client a one-time $1,000 fee for a quick WordPress project, you can turn it into a one-time $1,000 fee plus a $300 (or whatever) monthly recurring fee.

Passive income is another kind of income that you need to focus on. It’s any income that you earn without directly trading your time for it.

For web developers, maybe you can sell plugins or creative elements in marketplaces like CodeCanyon. If you love writing, you can start your own blog and eventually earn from affiliate marketing and advertising.

If you're good at what you do, why not create a course and sell it on Gumroad or Udemy?

Having small sources of passive income goes a long way in supplementing your freelancing income.

Wrapping up

Freelancing may be hard, but if you equip yourself with the right knowledge and attitude, success won’t be impossible. There’s always a way to overcome an obstacle if you plan ahead and try hard enough.

I hope you learned something from this article.

You can do it, my freelancing friend!

Much love,


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