Freelancing for beginners & the trap of overnight success

Freelancing for beginners & the trap of overnight success

Many of the overnight success stories out there seem too good to be true and when we look up advice on freelancing for beginners, it can be hard to judge who’s the real deal.

Today, I want to show you an unusual story about an overnight success experience I had freelancing on Upwork. Years ago, I had just left my job to freelance. I went to Upwork and began pitching projects.

Almost instantly, I landed my first client, and within a month or two, that turned into about $5,075 in work from just that one client.

freelance digital marketing project review

Not bad!

This was the first serious project I pitched on Upwork at the time. I know it sounds nuts if you’ve been sending out proposals and never hear back.

On the surface, it might look like I applied for that one job and instantly landed a great client. It would even be easy (and tempting) to make it look that way. It would also be wrong.

It is only the tip of the iceberg and what you are not seeing are the MANY proposals I sent at the same time but never heard back about.

Today, I want to take you behind the scenes and show you what an overnight success really looks like.

The truth about overnight success in freelancing

The reality of an overnight success as a freelancer is that there is a lot we are not seeing. Often, the example didn’t mention how the subject practiced sending client proposals that didn’t work out over and over again.… until they finally tweaked something and saw that overnight success.

The best way to claim an overnight success is by ignoring all the work done before the success or starting a replica project of something you’ve already done before, so you know the exact steps to success again.

Most people don’t tell the real story and with good reason. I stumbled on the sidewalk the other day, and I’m surely not going to post that anywhere. It doesn’t seem worth it to expose that to the world and feel like a fool.

When the superstars tell their story of struggle and how they made it against all odds, we tend to like the idea of the underdog winning. On the other hand, it makes us face reality and it isn’t as romantic as an overnight success.

You might have heard of the popular Dyson vacuum cleaners. It took James Dyson 15 years and more than 5,127 iterations to make it work but now he is worth $5 billion.

Another example is the Game of Thrones writer, George R. R. Martin, who has been writing for decades before creating the hit show. In fact, Cinemax recently bought the rights to his work Skin Trade from 1989.

Those stories of extreme success can feel overwhelming and are perhaps not exactly what we are looking for even though we wouldn’t say no to five billion dollars.

We tend to forget that the newspapers and magazines make money bringing us sensations — not the non-ordinary, everyday, details. The overnight success stories are in the newspaper exactly because they are a rare sensation but if we follow the news it can quickly feel as if that’s normal.

Freelancing is a terrific choice as a starting point because it is flexible enough for us to start on the side and we can systematically earn more until we are ready to quit our job.

The danger of chasing overnight success

As sexy as overnight successes are, it turns out that they secretly suck. It’s hard to shake the idea so let’s look at a few examples.

From time to time publications check back in with lottery winners, the perhaps most well-known type of overnight success, to see how they are doing now. They often agree that it isn’t as great as it first appeared.

In 2005, Lara and Roger from England won a $2.76 million lottery jackpot. They bought a big house, luxury holidays and a Porsche. After a freak fire, they spent most of the remains on repairs and temporary accommodation.

Before they won, the couple apparently never fought. That changed and the story goes that Roger drove away in the car after meeting a new girl.

Or there’s this guy named “Bud” who won $16 million in the US and was one million dollars in debt after a year! 

His former girlfriend sued him for a third of his winnings while his own brother tried hiring a hitman to kill him hoping to inherit some of the money.

What comes quickly, goes quickly I guess.

While Bud did say “I was much happier when I was broke”, the point here is that there might be a better way to our dreams of success than overnight success.

That alternative is to progress step by step in a systematic and predictable way, instead of from zero to a hundred like a fighter jet.

As Luis Romero argues, the problem with overnight success is that it makes us impatient and shortcut-minded.

That has devastating effects on our performance and judgement because we are taught that it is possible. And naturally, why would we do more for the same success when we (apparently) can get away with less?

It makes us feel like a loser and a failure when we see someone else who’s half our age and has done twice as much. It feels like there’s something we don’t know.

A secret that we are missing out on. Too many of us end up chasing the idea of figuring out what that is. 

It’s painful and ironically, that is exactly what holds us back from the success we are craving in the first place because we constantly move on to something new.

The overnight success stories of others lead us to become “wantrepreneurs” and start new things as we tend to think that the success came from a particular business model or industry.

Instead, it’s important to recognize that the only metric to achieve that is by working on the same project for a while.

The two personality types: which one are you?

Looking at it through this lens, I’ve noticed two different types of people. One loves doing something new and values that it is new and novel.

The other likes the comfort and confidence that comes with being great at something and knowing that there are unlikely any surprises when pitching or working on similar projects. 

It’s easy to mistake the latter for being lazy and afraid to leave their comfort zone. The difference is that they might leave their comfort zone in other areas that they find more meaningful. That makes it easier to complete freelance projects on Upwork.

Believing in the stories of overnight success puts us in the first group of people and keeps us stuck there until we figure out how to change the way we think about it.

The more we dive deeper instead of switching to something new, the easier it will feel to land freelance clients because we begin to notice the same patterns over and over again. Actually, it didn’t get any easier. we just got better!

An alternative to freelancing for beginners

One of the best “hacks” to freelance success for beginners is to spend more time hanging out with people that want or have the same as us because it will rub off on us.

Just like the opposite has an effect, too: If we often hang out with friends that drink all the time, we tend to drink more as well.

Instead of focusing on the overnight success, a more sustainable alternative is to accept that it’ll take longer but in exchange, the success will stay with us if we build a good foundation. And it sucks to give up something we love because we didn’t build a good foundation anyway.

For example, since I was a teenager going to the gym was a challenge for me. I’ve always loved sports but for some reason it was difficult for me to stick to a gym routine. Like everyone else, I’d sign up for the gym in January and stick to it for three months.

Eventually, I’d miss a day here and there. Before I knew it, I had missed a month and the routine was totally gone. The next time I tried, it happened again. It kept happening FOR YEARS…

Until something turned my grey hairs and I realized that even if you have money and other things that we dream of, it isn’t fun if we aren’t healthy. Think about it: cool, we can go on the wildest holiday of our dreams but what if we have constant back pain? How much fun is that?

I realized that I had been looking at it through the wrong lens this entire time. Instead of seeing how quickly I could get a beach body, the goal became how can I get it and look good for the rest of my life?

I learned that the best help we can get is from the science of habits because a habit will eventually be automatic like candy on a Saturday night or brushing our teeth in the morning.

It sounds boring but the results are terrific.

Instead of trying to lose 5kg in a week (and failing), my goal became to begin working out five days a week. I began with swimming and agreed with myself that I could go home after 15 minutes if I wanted to.

On the days where I didn’t feel like working out, I used outdoors-expert Bear Grylls’ trick of just exercising for one minute and then I could go home if I wanted to.

That saved me many times and the reality was that I would rarely go home after just that but it helped me get out of the door. The only thing that counts in the beginning.

Fast forward three and a half years, I’ve been consistently training 4-5 days a week and seen excellent results because that got easy after a while, so I added more to it.

It changed because I began measuring how often I’d get out there rather than what I did when I was there.

We can apply the same principle to freelancing on Upwork by for example spending 15 mins every morning just looking at projects. Sooner or later, we’ll want to apply for some of them, one thing leads to the next and suddenly you’ll wake up to clients knocking on your door.

Fifteen minutes is little but if you feel like it is challenging to get off your ass, it might help. That means no more life hacks and instead, more patience. Ironically, that is what gives us the results we wanted from the life hacks and overnight success in the first place.

Now that you and I have looked at the elephant in the room — what to avoid — let’s look at common advice you can throw out the window and what to do instead if you want to freelance as a beginner and earn money on the side.

The problem with most advice on freelancing for beginners

When people talk about freelancing for beginners, they love to offer advice like “write a blog” and you “MUST get on Facebook, Instagram, Pinterest, and Twitter”.

It’s hell.

They mean well and it is not meant as an attack but we can only do so many new things at once before we eventually crash and burn.

Most of the advice about freelancing for beginners is solid but the challenge is that there is too much of it.

Everyone (including me) has an opinion on what to do and for someone new to freelancing it’s a lot to take in at once. It gets overwhelming and leads to feeling paralyzed.

The challenge comes down to when to do what among all the options out there. A coach once told me what NOT to focus on and it was perhaps the best business advice I’ve ever gotten.

To hear from someone who’s already been there what we can ignore and come back to later is liberating.

Next, let’s look at popular questions about freelancing from beginners.

Your questions answered

Some of the most common questions I get from new freelancers are:

  • How to find and land clients (and what if you’ve sent many proposals and never heard back)
  • I don’t have a freelance idea
  • I don’t know how to set my rates
  • How do I know that I am good enough to do the work?
  • Should you use freelance websites to find work?

Let’s dive into each one in a rapid-fire manner before looking at the ingredients we need to begin freelancing. That way, you’ll gain a quick overview before starting on your freelance journey.

How to find and land clients

I know this can be hard to hear if you’ve been spending a lot of time on business cards, a website, and social media. 

To land clients, we simply contact businesses via our existing personal email or use freelance platforms. We don’t have to be spammy and we don’t need a professional email.

If businesses aren’t interested, it is either because they don’t care about the problem we are working to help them solve, the way we reach out to them isn’t attractive or it simply isn’t the right time.

Anything else, including a website or social media profiles doesn’t matter because it will make you feel demotivated when you spend a lot of time working on it and get no results.

I don’t have a freelance idea

If you don’t have an idea, see how to find one here.

If you already have an idea but haven’t started yet, why not? Do you need to “get your ducks in a row”? 

You might feel afraid of starting for some reason, like not knowing what to tell clients, how to find them or what to charge. That is fine, you don’t need to know everything upfront. Rather work to understand what’s blocking you and find a solution for each thing one by one. Most of those answers can be found in this guide.

I don’t know how to set my rates

As a starting point, using an hourly rate is a good choice. You’ll get a better feeling for how long things take the more projects you complete and you can adjust your rates as you go.

There is no scientific answer to this, simply pick a number you are comfortable with. You can adjust as you go. For me that was $25/h for my first few projects.

How do I know that I am good enough to do the work?

For me the balance is if I know the scope well but might not have the latest updates on the topic. 

It is important to understand your client. Many prefer to work with someone they already trust even if that person isn’t the best in the world at a new topic. The trust is a bigger deal to many than the lack of skills as long as you are resourceful.

It also depends on your client’s goal. Is this an area where they absolutely need to get results and are 100% focused on it or is it something that they just need to get done? Pick what you are more comfortable with.

If you have the feeling that you can complete the project and make them happy even if you have to spend some free time on top of the paid hours, I’ve found that to be good enough to start. 

If you know that you can look up how to do the task and from that, do it well for the business, go for it! The important part here is more about how we help them solve their problem and how we feel about it.

You’ll be surprised how many businesses value that we communicate with them frequently and are proactive and organized. Resourcefulness and being able to look things up will also help.

Should you use freelance websites to find work?

Only if you already have an approved profile. Otherwise you’ll benefit more from reaching out to businesses directly via email since you can learn more about them and find just the right ones for you to work with.

On freelancing platforms, you often don’t know who or what type of business you are working with and that can make your experience unnecessarily challenging.

The only ingredient beginners need to land clients as a new freelancer

freelancing for beginners

Freelancers starting out often get into doing too many things at once. In this chapter, we’ll look at the only ingredients you really need to get moving and earn your first money freelancing. 

There is one thing that is more important than anything else: helping a business solve a particular problem. That’s it!

It sounds overly simple, right? 

The challenge most beginner freelancers have is focusing on a problem they think businesses have when in reality it isn’t a priority for them.

The key is to focus on a problem not that you and I feel the business have but one that they know they have. Reach out to other similar businesses and ask. They will help if you are friendly and tell them you are simply looking to learn.

If this makes you feel uncomfortable, great! It means you are on the right track. This is the opposite of an overnight success. Instead, we are systematically figuring out how to earn money on the side.

What can wait

Compare that to all the things that we are supposed to do but that doesn’t really make a difference in terms of earning more but will just keep you feeling busy. 

Here’s a quick list of things you can ignore until you are making several thousands per month freelancing:

  • Create a website
  • Blog
  • Be on social media
  • Get business cards
  • Networking events
  • Facebook groups or forums

Solving a good problem for your clients will make you the most money by far. It’s that one thing. I’m repeating it because it is THAT important.

Now that we know what to focus on and what to ignore, let’s look at how we can make sure we do a good job.

How to get “overnight” success with Upwork freelancing: the 30-day Upwork taster

I deliberately kept the above section short because you don’t need to worry about anything else.

With this simple framework, you’ll be able to predictably get responses to your Upwork proposals and land clients. 

In fact, it’s so simple that I bet only one percent of people reading this will take it seriously. The vast majority reads it, nods along and goes back to their old ways. That’s why I’m not afraid to give away the “secrets”. Most people don’t act on it anyway.

Anyway here are the four steps:

  1. Set aside 45 mins at a specific time during the day, that you know you usually have free every day. I like mornings but take your pick
  2. Practice blocking out distractions during that time. It will take a while to get good. It’s fine to procrastinate at first as long as you show up
  3. During that time, send ONE good proposal. If you feel as if that takes less time, brainstorm what you could add if it had to take all 45 minutes to write the proposal. What else could spend extra time adding to make it good?
  4. Do that for 30 days in a row without missing a day

That’s it. Simple right?

Bonus step: put a calendar on your desk that shows a whole month in one page (using an electronic version doesn’t count). Then cross out each day as you send your proposal. It’s a great help to stay on track.

SSO Fiscal Deadlines | Human Resources

If we instead of following the steps above move on to read more tactics without having the habit down, we’ve already lost.


  • Overnight success might be sexy but it isn’t what it looks like on the surface and the downside is bigger than the upside. A better alternative is a slow and steady, step by step, process to success because we build a strong foundation that will keep us for the rest of our lives
  • There’s value in not trying out a bunch of new stuff and instead dive deeper within one area. Not just for the freelance projects themselves but also for the pitches
  • To earn money on the side with Upwork, most of us need to spend less time on tactics and more time on showing up every day

Which freelancing site is best for beginners?

In my experience, Upwork has been the best freelancing site for beginners because they have the most client projects available.

How can I start freelance with no experience?

The best place to begin with no experience is to help with smaller projects that you can do a great job at. That might be online research or data entry. Focus on doing an extraordinary job and clients will take notice.

Is freelancing easy?

Freelancing is not easy in the beginning but over time we get better and so it feels easier.

How do freelancers get paid?

Freelancers often get paid based on an hourly rate, on a project-basis, or with a monthly retainer (a fixed monthly fee) depending on their agreement with the business they help. There is no one size fits all, some type of payments fits some type of projects better than others.


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