A Guide to Becoming a Successful Freelancer

How do you become a successful freelancer?

I couldn’t possibly answer that for everyone. The best I can do is tell you what I did and try to simplify it into principles that can be widely applied. I have been self-employed as a video creator since April of 2016, so my advice comes through the lens of a creative professional. 

First, what is the difference between a freelancer and entrepreneur? 

I like Seth Godin’s definition

Freelancers get paid when they work. We’re not focused on scale… and we’re not tiny versions of real entrepreneurs. Freelancers do the work for clients who need them.

Hiring employees to scale when you’re a freelancer can be a bit of a trap, because you are likely to give up the very thing you set out to do in the first place.

Entrepreneurs, on the other hand, are organized for growth. The job of the entrepreneur isn’t to do the work, it’s to build a company that does the work.”

I don’t know how to be an entrepreneur. I’ve never done it. I have only ever been a freelancer, and I agree with Godin that it’s important to accept that difference.

These are just a few things I’ve learned. You might know better. Follow them at your own risk.

1. Develop the character within.

So much of being successful in client work comes down to having a personality that’s easy to work with. You also need more than just a kind disposition.

You will never really succeed at freelancing (or for that matter in any other part of life) if you don’t consider the needs of others over your own. This is not only the key to being likeable, it’s the only way to find out what really sells.

I won’t talk about this in depth here, but I’ll point you in the right direction. If you’ve never read the classic The 7 Habits of Highly Effective People, you should make time to do so immediately, and not only read it, but digest and apply the principles to your own life. 

It asks big-picture questions we often don’t consider in life until it’s too late, such as our purpose and meaning and what we want people to say about us when we die. It also goes to the foundational level of relationships and would probably solve 90% of relational issues if people applied the habits.

2. Find a skill.

What are you naturally drawn to? What do you have a knack for? Think more along the lines of things you’ve already shown a prolonged interest in and not things that sound fun in passing. Your disposition likely provides clues.

I was never drawn to science or accounting or law. I never wanted to be a doctor or vet or chef. I did have a burning interest in music, photography, and writing since I was an early teenager. I wanted to do these things whether I was paid to do them or not. They made life interesting to me.

3. Vet the skill (See if it can make money).

Just because you love doing something doesn’t mean you could do it as a career. It needs to be profitable. People need to be paying for this already.

If you have never heard of anyone getting paid for what you’re thinking of doing, it’s probably a bad idea. 

If the market is oversaturated with people doing what you do, it will be harder to make money, but at least the idea has been proven.

If you have a new idea you just can’t let go of, try to make a sale doing it as fast as possible. If you can’t get anyone’s interest, let the idea die.

When you’re planning to work with businesses, ask yourself this question: how can I help them make more money? Because at the end of the day, this is what every business wants. If your idea simplifies life for the business owner, or makes their process more efficient, or reduces friction between employees, you’re still helping them make money because these things are roadblocks to profit. That’s how they see it and it’s how you should see it.

If you’re offering a service to consumers rather than businesses (things like wedding videos or slideshows for graduates), the game is a little different. They usually want it as cheap, fast, and high-quality as possible, but it’s hard for it to be all three.

You don’t have to invent a new thing. You can focus on being exceptional at something people are already paying for.

4. Develop the skill.

No one will pay you if you aren’t good. One might, but they won’t a second time, and they won’t recommend you.

Getting good is one of the harder parts of the process and requires patience. It takes time. The only way you can do it is to create and finish projects again and again. And you need to publish them, even if they’re bad, because it puts a necessary pressure on you.

If you can get a full time job where you can learn your skill on someone else’s dime, this is the sweet spot. I was fortunate enough to be employed making videos for 8 years before I branched out on my own. Few people get that chance. 

If you don’t have that privilege, don’t be discouraged. It didn’t need to take that long. Most of that time I didn’t want to be a freelancer and only started entertaining the thought towards the end.

Start putting in the reps, finish projects often, show them to the world, be embarrassed and frustrated at how bad you are, and pick up and do it over and over. It’s only through this repetition that you’ll get there.

5. Learn the business. 

Development applies both to your skill and your mindset. You might have the skill a long time before you’re ready to branch out and run a business. You might find that you actually don’t want to be self-employed.

For years I didn’t even consider working for myself. It took me seeing how a business was run—how clients were developed and meetings conducted and projects completed—before the confidence in me rose. Eventually, I started seeing that I could do it for myself, but this process takes time. When you’ve been trained to look to someone else for your income your whole life, thinking about finding it on your own can be scary. It can also be motivating.

At one point in time I was making less than $40,000/year working for someone else. We took on a video project where I provided most of the creative direction, scheduled the shoots, directed the talent and crew, edited the final videos, and created all the motion graphics animations. Apart from the sale and client relationship, which are hugely important and without them there would be no business, I was responsible for most of the project.

How much did my company charge for that project? $90,000.

This was perfectly fine and normal. This is exactly how business works. I wasn’t mistreated in the slightest. I agreed to my salary and was compensated well, and I was grateful to work with generous people who valued my skills.

Still. I did 85% of the work on a project that lasted a month and paid more than double my annual salary.

Realizations like this motivated me through the fear.

6. Show your work.

As mentioned already, you must create and publish the projects you’re working on. Show them to the world when you aren’t ready, when you know they’re bad, when they embarrass you. Otherwise, you will never grow.

Showing your work does two things:

  1. Displays your skill to the world.
  2. Creates an association between you and the thing you do. 

This is marketing, plain and simple. You’re strengthening the tie in people’s minds between you and the skill. When they think of it, they think of you. “Oh yeah, Adriana is a photographer. You should call her!” Or, “Doesn’t Jacob work in consulting? He’s always writing about business online. Maybe you should call him.”

“But I don’t have any work to show!”

You’re going to create some to show.

Believe it or not, I almost envy you, because you’re about to do the coolest and most exciting project you can imagine. There’s only one catch: you’re going to do it for free. 

Yes, absolutely free. You aren’t going to discount it at all. (I may have first heard this concept from Seanwes, I can’t remember.)

When you do a project for free, you maintain control. You can do it exactly how you want to do it, and because it’s a gift, the client won’t make unreasonable requests. You’re not pulling a quick one either. You’ll tell them exactly what you’re doing from the beginning and make sure they accept the terms in writing just like a normal project. 

I once approached a local donut shop and did this. It was free, and the only stipulations were that they couldn’t edit it, they couldn’t use it anywhere without giving me credit, and it had to keep my logo on the ending. They were thrilled, and the video turned out great—in fact, it’s probably the most popular video I’ve ever made. It got over 24k organic views on Facebook.

That’s great for them and great for me. It’s a lot of exposure for about 3 days of effort.

Why would you work for free? 

A few excellent reasons:

1. It gives you something to work on. – Do not ever twiddle your thumbs and think about how awesome your work is going to be when you finally get a project. You have to do something now.

2. It gives you a chance to learn and edit your process. – The pressure is totally off as you reach out to the client. Easiest sales call ever. “I’m calling because I want to make a video for you, absolutely free, to spread the word about my work. Would you be willing to meet in person to talk about it?” You’re still working with a client, you’re still planning your shots, you’re still delivering something that represents their brand. Pretend they are paying you $100,000 for the work. How would you act? Do that with this project.

3. It promotes you. – I wouldn’t say it’s free for you since you’re spending your time on it, but when you first get started you have more time than money. You don’t need to spend money on a marketing campaign anyway. Most advertising dollars are wasted because people expect a quick fix and don’t want to put in the effort. You will put in the effort, and you’ll see the results from doing so.

7. Send emails to your personal network.

Send a message to all friends and family that you think would be interested to hear about your life and career change. This email is simple, human, and short. It explains what you’re doing, who you help, and how grateful you would be if they mentioned your name if the opportunity arose. You aren’t selling anything. Don’t ask if they have work for you. It doesn’t matter how much your friends love you, they will be creeped out when you try to sell to them out of nowhere, which is why multi-level marketing is so gross.

Here’s the exact email I sent out:

You should expect nothing from this. This is the very beginning of letting the world know what you’re doing, and it puts a tiny blip on their radar. However, the people who love you want to see you succeed and will be happy to promote you should the need arise.

My first few connections came from this step, which led to clients who pay me to this day.

8. Make calls to potential clients.

I did very little of this, but I did do some and it led to paid projects. It’s still a struggle for me to pick up the phone and try to make sales. I don’t like being sold to, and I have a feeling no one else does either. But if you know what you’re doing and are clear on your goals, cold calling is still effective.

What is the goal of a cold call? It depends on what you’re selling.

Low-cost purchases are easier to talk about and you can get to the pitch quickly. The more expensive the purchase is, the longer it takes to nurture your prospective customers.

Think of it like a relationship, because it is. When you’re looking for someone to cut your grass, you can find out in a matter of minutes if they are the right person for the job. If their price is right and they listen to you and show up on time and cut grass well, they’re in. On the other hand, if you are looking for a spouse, it’s going to take a while to know if that decision is right.

If I was selling air filters or window cleaning services, I could make a list of 300 local businesses, pick up the phone, and basically say, “We provide pure drinking water for businesses. Is this something you are interested in? Oh, you already have this service? Well, would you be interested in a free sample of our water? I should mention we’re cheaper than most competitors…” You get the idea. I can get down to business quickly because the stakes are low and the investment from the customer is small.

In my situation, I’m not selling small-ticket items. Videos can cost an organization between $2,500-$10,000, and sometimes many times more. You don’t just pick up the phone and ask if someone wants to buy that. 

You can call and hope for a successful introduction. Ask if they have a minute, quickly let them know that you’re here (because remember, what you do could really help them), and ask if they would be interested in letting you buy coffee or lunch for 30 minutes in the near future. This is still an ask, it’s still time they are spending on you, they still have to be somewhat ready to purchase a video before they say yes, but it’s a lot easier than making a cold sale.

9. Your first win: in-person meetings.

What I was after was human connection. Business friendships. Because that’s really what it comes down to anyway. If you sell high-ticket services that require a lot of face-to-face interaction with your clients, you’re going to have to have some sort of connection with them. If they hate being around you, or you hate being around them, it’s doomed.

Your goal is the same in this business friendship as it is with any relationship: seeking to understand them. Remember point one above. This is one of the 7 Habits: “seek first to understand, then to be understood.”

There is no other way to do this but by putting in the time. People have to trust, not just that you can do good work, but that you can handle the task at hand, and this level of trust isn’t given overnight. 

At this meeting, listen far more than you talk. Don’t show off 10 videos you’ve made when you haven’t even heard if video is a part of their strategy. Get to know the person. Who are they? What’s their story? What are they working on? What challenges are they facing? When they share what stumps them, give them your best advice. If possible, teach them how to get what they want for free—even if it means without you!

I don’t know how many times I’ve ended up telling a potential client how to get what they want without me. Is that smart business? Absolutely. Am I losing a sale? Absolutely not. This is one more deposit into their trust account that proves I’m out to help them and not use them. This builds long term results. When the true need for me arises, they know who to call.

If at the end of the meeting you’ve listened with all of your attention, let them do 75% of the talking, added as much value as possible for free by giving away your expertise, and it becomes clear they won’t be working with you soon, there’s a final ask you can make.

Ask them, “Is there anyone you know who comes to mind who might need what I do? Would you be willing to connect us, even just giving me permission to email them and use your name?” If they’ve enjoyed the conversation and seen that you’re competent, they will usually be happy to do so.

Then you get back to your office and send an email with their name in the subject line to the new person. E. g., “Subject: Madison Jones sent me…” This email will almost certainly be opened. 

Repeat the process with the new person, asking at most for an in-person meeting, and showing sincere interest in them if they say yes.

And if they say no? Write down when you reached out, give it a couple weeks, and try another method of getting on their radar. Send a hand-written note with a $5 gift card to a coffee shop. Find an incredible article that could help them and send it their way. Write one of your own! Do something you would do if you were already good friends.

Pro Tip: teach something related to your field.

As an ongoing effort to market your services, consider teaching about your field. This does several valuable things:

1. Teaching markets you. – It keeps your name in front of people in the best way possible. You’re not just saying, “Look at me, I’m awesome, you should buy from me,” which people tend to zone out or even resent. You’re teaching something that helps or interests them, and their love for your name grows.

2. Teaching positions you as the expert. – If you know enough about a thing to teach about it, people will see you as very capable at your job.

3. Teaching opens up endless possibilities for content. – There is no marketing without content—without the pictures, videos, or words you put out into the world. Many marketers scratch their heads merely trying to figure out what to publish. Start by teaching the most basic lessons and your content will seem endless.

4. Teaching can grow into something more. – Publishing content consistently will expand your influence in your field. Eventually, you could even have enough content to create an information product—a class or course or e-book or workshop.

10. When the first paid project comes along, execute with everything you have.

While you always want to over deliver on your promises as a freelancer, when you’re first starting out, it’s more important than ever. Go above and beyond to make those first clients proud. They are the start of the fire you’re building, and it takes more effort to start a fire than to keep it going.

Communicate with your clients. Let them know when things will be done. If something goes wrong, own it completely, take every ounce of the blame, and do whatever it takes to fix it.

11. Ask for referrals.

Hopefully your client is blown away by your work, your process, the whole experience. If they are, this is the perfect time to ask the same question of them you’ve asked of others in meetings: “Is there anyone you know who comes to mind who might need what I do?” 

They will be thrilled to help spread your name.

12. Repeat steps 8-11.

Before long, you should have as much work as you need. It’s a sweet feeling when you no longer have to ask for work but the work starts coming to you because you have momentum.

When are you ready for full-time freelancing?

You’re ready when you’re losing money because you’re unavailable due to working for someone else. When your day job pays you less than you would be making spending that time on freelance work, it’s time to quit the job.

Or, you don’t ever have to quit. 

Many aspiring freelancers feel they must do one thing or the other—that they’re either an employee or a freelancer, but never both. There is no rule that says you have to choose. There is no shame in getting a “job,” and no superior glory in freelancing on your own. It’s a matter of what you prefer. 

If your job is flexible and comes with good benefits, maybe you shouldn’t be quick to leave it. These things get expensive when you’re paying for them on your own.

If your job exposes you to people you enjoy being around, maybe you shouldn’t be quick to leave it. It can get lonely sitting in your office all day chipping away at your own projects. 

If your job provides a nice contrast to the freelance work you’re doing and refreshes your creativity, maybe you shouldn’t be quick to leave it. Sometimes the best thing you can do in creative work is walk away from it for a time. 

But if your job is truly holding you back, if you’re ready for the next level of growth in your freelance career but you have no more time, or if your job has become your main excuse for not going all-in on your dream, you should quit the job. 

At some point, you may have to burn the ships, as they say. There is nothing as motivating as knowing it’s all on you—that if you don’t do the work, if you don’t get the clients, if you don’t deliver on your promises, you will fail. This is the fire that pops your eyes open in the morning and plants your feet on the floor with purpose. 

You just have to do this reasonably.

Having a safety net.

This can look like one of two things:

  1. Several months of living expenses in cash.
  2. A part-time job that preserves availability for freelance work.

You could also combine the two.

When you’re first starting out, your freelance work should not be your only source of income. For one thing, there probably won’t be enough of it, and for another, you might compromise your work standards just to get paid.

You need a safety net, a source of steady income so you can breathe. This is in no way a defeat. In fact, you can still consider yourself self-employed while working for someone else. Think of your employer as a long-term freelance contract. They’re just one of your streams of income.

The ideal scenario is a job in your field where you can get paid to sharpen your skill. 

The second-best thing is to find a job that is flexible and provides you with enough spare time to build your freelancing career.


It didn’t take me long to realize that I don’t need many clients before I’ve reached my capacity. I just need a few good ones. If I was in a situation where I needed more all the time, my approach would be different.

If that’s you, I highly recommend Book Yourself Solid, the book by Michael Port. It lives up to its subtitle: The Fastest, Easiest, and Most Reliable System for Getting More Clients Than You Can Handle Even if You Hate Marketing and Selling. 

It’s absolutely  true. If I applied what Michael Port teaches in this book, I would have more clients than I could handle in a matter of weeks. The reason I don’t is that I’m satisfied with the amount of work I currently have.

Best of luck on your freelance journey!

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