How to succeed at freelancing

February 6, 2018

The essential principal of business —of occupation in the world — is this: figure out some way in which you get paid for playing.Allan Watts

Let me begin by saying that while this has worked well for me, it may not work for you. Maybe even freelancing isn’t even for you. What I am focusing on sharing is more about how to do work that gives your life meaning. It doesn’t matter if that’s as an employee, a freelancer, or something entirely different. All that matters is that it is up to you.

I don’t know about the freelancers here, but whenever I tell someone I’m a freelancer I seem to get a variation of this reaction.

People seem to react as if I just told them I was let go from my job. Surely, working by yourself can’t be something I’ve chosen, right? Some seem to think that this is just an “in-between jobs” kinda thing and I’ll get a full-time position eventually because that’s the “safe” choice. People also ask me whether or not I’m “still working by myself” assuming that if I don’t want to get a full-time job, surely I should hire co-workers, right?

Here’s my friend Paul.

I believe freelancing is the ultimate way to take control of my life, my finances and my daily happiness. I don’t freelance as an interim step until I build a huge company. This is a long-term, long-lasting career that’s now more stable than any corporate job. I freelance because I love being a freelancer.

It gives me the ability to chart my own path in life, not to mention working in my underwear (with my clients being none-the-wiser). I choose who I work with, when I work, and most importantly, when I don’t need to work.Paul Jarvis

While I’m not sure about freelancer’s obsession with working in their underwear, I fully agree with everything else that Paul says. Truth is, as a freelancer I make more money, work less, and only when I want to. I’ve been freelancing for ten years while the longest I ever stayed with a company was for two years. Plus I get to work with my dog!

What I’ve learned along the way

In order to achieve success, we need to understand our motivations and that starts with a deep look into ourselves. We want to be able to assure those who care (or criticize) us on our freelancing choice. It’s not something we were forced to do because we can’t manage to keep a job. Instead, it’s our chosen to path to achieving our goals through hard work and dedication.

Simon Sinek talks about the importance of “Start with Why” for companies and this applies to you as well:

  • What - This is something everyone knows. It’s even what we ask people! What do you do? I make websites, I’m a photographer, I’m a journalist, I sell … stuff.

  • How - Most people know how they do it, however not everyone. Especially in larger organizations, many people have no clue on how they do what they do.

  • Why - this very few people know. What’s your cause? This is HARD. I believe in challenging the status quo and doing things differently.

Although Simon tells us to Start with Why, I like to start on the easier end and work to the trickier why.


Since you’re starting your freelancing career, I’m hoping that this is something you already know. If it’s not, no worries! You can explore different things! Whatever you choose to do, make sure you can describe it quickly and thoroughly as possible.

Here’s two examples from two different companies:

We do digital advertising on Facebook.


We’re a communications agency and the core of our integrated offering. We’re passionate about creativity that has the ability to affect and touch - advertising that people care about. The kind that often separates a product from another. The ability to communicate and create engagement through advertising is perhaps more important today than ever before. Through creative ideas that span across all disciplines in analog, digital or social channels there’s every possibility to position yourself against your competitors.

Although the second option is 10 times as long, I have no idea of WHAT they actually do. Describe what you do in a simple and easy way and be as specific as possible. Being a Javascript developer is great, but being a Javascript developer for travel sites is even better.

Being small is nothing to be insecure or ashamed about. Small is great. Small is independence. Small is opportunity.

When I first started freelancing, I used a company name and everywhere on my website I spoke in terms of ‘we’. My thought was that it was more serious if ‘we’ were several people. Turns out, one of my biggest benefits and hidden powers is in fact my size! It allows me to be more agile in my work style and stay personal the entire time. This has lead me to believe the term “B2B” (business to business) cannot encapsulate the experience I bring to my clients. I do adjust to their different business models (depending on their target audience), but choose to keep business relationship personal, yet professional. This is often refreshing to the client as I don’t prioritize the company over the people in the company and the people whom they serve.

I am a professional because I am personal.

Fredrik Eklund, NY realtor described how his company wanted him to use a corporate profile for his social media interactions. Fredrik declined this, claiming that his success is based on his personality. He later became the highest selling realtor in the US! This stuck with me for years.


Most people know how they work and their process and extend that into their freelancing journey. Me? I choose to give my clients an agency-like delivery (or above) with a personal touch. Clients never have to worry about someone else taking over their account and over the years, we learn to work in the most optimal way. This different relationship approach is appealing to clients when I am running against agencies who are more traditional. So speaking of clients…


One thing that most people heading into freelancing ask me about is getting clients. Clients are central to your success and we all want to remain in business.

Paying clients are the ones who put food on your table. Without them, it’s not a business you’re running, it’s a hobby.

The truth is, there are a million different ways to get clients. As a freelancer, you have the freedom to find clients in the way most comfortable for you. Some prefer going to networking events, others prefer to use their contacts, and some happily find their’s in online marketing. Once you find them, the journey is just the beginning.

Too many companies fail when it comes to retaining their clients. They deserve your care and attention even between projects. For instance, most companies offer new clients free trials or discounts, but don’t continue to offer any great values to past clients. Don’t be like these companies. Play the long game.

That said, there’s one thing we should get out of the way.
Money comes from work and vice versa.

A lot of companies will try to persuade you with promises of “more work on the horizon”, but in my experience, that can put you in a vicious loop. Working to become eligible for more work isn’t fair or honest. If you don’t respect the work you do and put value in it, don’t expect anyone else to.

Pricing work

Being small and independent you also have the option of choosing pricing strategies that work for you. And you can even change along the way! Here are a couple of the different pricing options I use:

  • Hourly rates - some clients prefer this because it’s easy for them to compare to others. I dislike it because it punishes me for being a fast worker. Use with caution.
  • Value based - this is my favorite, but a little complicated for small projects (or ongoing work).
  • Retainers - this is great for securing up income over longer periods of time.

Use a mix and test different strategies!


Very few people take the time to really understand what their live goals are and how their style of work can play into this. Why do they design homepages? Because it pays the bills or is it something more? Without a destination, it’s unlikely you’ll end up there any time soon. A freelancing career allows you to ask yourself questions like these:

  • Do you want to spend more time with your family?
  • Have more control over your time?
  • Earn more?
  • Work less?
  • Travel?
  • Work from anywhere?
  • Be your own boss (this isn’t always as fun as it might sound)

I first tried freelancing in 2004 without a plan. I had no idea why I would freelance, so naturally I failed miserably. I ended up taking a full time offer at the first agency I tried to freelance with. I failed because I didn’t understand my WHY.

Years later, I realized that I want to define my own rules of working. I want to challenge the idea that more employees equals a more successful company. I want to get paid for the work I’m doing rather than 40 hours per week regardless of how much I work. I don’t work just for a paycheck anymore. I work to provide value for others and meaning for myself.

So here’s my final secret for you;
find happiness, then success.

It’s impossible to even enjoy your success if you are looking through an unhappy lens. Once you find your happiness (purpose, meaning, inspiration, value), success will follow.

If you've read all the way down here and enjoyed this post - odds are that you'll enjoy Mastering Freelance - my book with everything I've learnt while freelancing. It has a free email course too!

It’s honest, authentic, and accessible.

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