Business Design

The Practical Guide to Freelancing: surprising ways to succeed from day one

Published on:
March 19, 2021
Written by:
Sebastian Hallqvist

I know the feeling.

You don't exactly know what you want to do with your life. There are so many careers you could pursue. So many options.

Sure, some of them sound intriguing, but you don't actually know what they would mean for you. This is the irony of making life decisions when you're young; you don't understand your options all that well.

You can feel yourself being pulled into a traditional 40-year career at some job you don't really care about. It's where society wants you to go. And you will end up there, almost by default. But something about it doesn't add up. A voice deep down is screaming at you not to jump on the hamster wheel. Your intuition says there must be another way to live your life.

Perhaps you've already spent years working a "normal job", only to arrive at the question, "is this it?", followed by an itch to do something more rewarding.

Either way, you know what you don't want: to spend the next several years rotting away in the same cubicle, day in and day out, working on some meaningless task because your boss told you to – just so you can make enough money to scrape by and wake up the next morning to do it all over again.

There is more to life than that.

Becoming a freelancer may have crossed your mind. You’d like to create something of your own and have the freedom and autonomy you can only get from self-reliance.

But how do you build a successful freelance career? And is it even possible for someone like you?

You’ve probably been fed this idea that you have to slave away at a job for years to become an “expert” before you can even think about going out on your own.

While that’s sometimes a smart way to do it (more on that later) — I’m here to tell you it’s not true.

I successfully launched my freelance design–career right after college, without even finishing my bachelor’s degree.

Three and a half years later, I am able to work only half-time and still bring in a comfortable six-figure income. And I don’t have to live in a city as expensive as New York or San Francisco to find the work.

I’ve been involved in challenging and meaningful projects with people from all over the world. I work 100% remotely — and I did it before the pandemic made working from home a norm.

The reason I only freelance halftime (and nowadays even less) is so I can spend the rest of my waking hours bootstrapping my startup, which is what I dream of doing full time.

To my younger, lost, and confused college soul, this would have sounded like a dream. It still kind of is, and I’m grateful every day to be living it. But it wasn’t exactly easy to get here.

It’s hard to get the ball rolling in the beginning. All of the odds are stacked against you. Perhaps more importantly, it may not necessarily be what you want to do at all.

I made several mistakes along the way that I could have avoided. Knowing what I know now, there are things I would have done differently and one path, in particular, I would have taken in order to make the transition into freelancing smooth and successful from day one.

If you’re still in school, recently graduated, or a couple of years into your professional career, I want this to be your guide for accurately considering freelancing as a way of life.

I will share the most powerful lessons I’ve learned in the last couple of years as a freelancer and entrepreneur so you can have the confidence and know-how to successfully launch your freelance career if that’s what you decide to do.

Before the practical lessons, however, let’s talk a little bit about what it means to be a freelancer and do your own thing.

Should You Go Out on Your Own?

First of all, you may have some doubts about whether you’re the kind of person who should go out on your own. While I don’t think there is just one type of person who should, it’s definitely not for everyone.

Running your own company has many benefits, but it also has specific demands — and even drawbacks. I personally know people who used to run their own company but are now much happier as an employee.

While I can’t tell you what type of person you are, I can tell you what brought me to this path.

I’ve always been introspective, slightly weird, and highly independent. Even more telling, I’ve always had an unusual urge to get things exactly right according to the way I see things.

When I was little, my mom could only play with my brother’s Legos because if she even touched mine, I would immediately get upset that she “did it wrong.”

While I’m not a kid anymore, and I’ve actually gotten pretty good at collaborating with other people, this is still a part of my personality.

I also have a high risk tolerance and a deep, intense intuition telling me there’s no long-term alternative for me: I’ll never be content working for someone else.

In my experience, most freelancers and entrepreneurs have similar qualities:

  • They’re highly independent
  • They’re comfortable being alone and making uncommon choices
  • They’re comfortable with (sometimes extreme) uncertainty
  • They’re confused by the expression being a self-starter (what’s the alternative?)
  • They’re curious and impatient

If you have some or all of the qualities above, chances are you would do well to go out on your own.

It can get lonely

The problem with doing your own thing is that you’re doing your own thing. There’s often no natural social context. If you don’t develop smart and deliberate habits, it can get lonely.

Different people will have different personal requirements for social connection. Some programmers I know are perfectly happy to stay in their “cave” seven days a week. Other freelancers need an office with coworkers to go to every single day.

For me, going to my favorite coffee shop most days, messaging with my coworkers throughout the day, and my free-time activities are all enough to keep me sane.

It also helps to get to know other people with the same kind of lifestyle. Some of my best friends now are also freelancers and entrepreneurs.

It may not be what you imagined

Many people dream of the freedom to work from anywhere or even to not have to work much at all. While this is certainly possible to achieve as a freelancer, many fail to realize it’s not actually what they want.

In order to stay sane, humans need meaningful things to do.

In his now-classic book “The 4-Hour Work Week,” Tim Ferriss calls this “the void” — when you finally achieve “freedom,” you then have to fill the void that freedom creates.

Ironically, what we find meaningful is often some type of work.

It helps to anticipate this so you can drop the delusional fantasies of living your life on a tropical beach and instead figure out what type of work will be part of your ideal day.

Lastly, there are lots of ups and downs with running your own thing. The highs are higher, but the lows are also lower. To thrive as a freelancer or entrepreneur, you have to learn to like this roller coaster.

That being said — it’s pretty awesome

If you’re the right kind of person, with healthy expectations, I couldn’t recommend freelancing enough. It’s pretty awesome.

You can make more money than at a regular job, and you have more freedom to design your life. For example, I recently relocated to Switzerland for a couple of months so I can ski the Alps when I’m not working. There are endless possibilities like this. You should get excited about this kind of lifestyle, but don’t forget you’re the only person responsible for making it all happen.

Now that we’ve set some expectations, let’s get into the most powerful practical lessons I’ve picked up — and some common mistakes I’ve identified during the last three and a half years as a freelancer and seven years as an entrepreneur.

As mentioned, there are some smart moves I’d have made in the beginning had I known what I know now.

But let’s start with something I did get right from the very beginning, thanks to a lesson I learned playing music as a teenager.

1. Focus On the Craft

In my teenage years, I played guitar in a rock band. And you know what — we were going to be rock stars!

So why haven’t you heard of our music?

When we started the band, we first wrote a couple of songs and practiced in my friend’s basement. Then, we quickly started promoting. We got gigs at corporate parties. We entered music competitions. We rented a studio and posted the recordings on YouTube. We even put together our own gigs and forced our friends to come to see us play.

To be fair, we did put ourselves out there. That’s important. But we forgot the most important thing of all: Instead of spending all that time promoting, we should’ve stayed in the basement honing our craft — writing better songs and becoming a unit.

We should’ve done that until we were so good we no longer had to force our friends to listen to us. Until we no longer needed to ask to get gigs.

“Be so good they can’t ignore you.”

— Steve Martin

I like that quote from Steve Martin because real success is literally that simple.

This is what we should’ve been focusing on in my band, and it’s what you need to focus on to succeed as a freelancer. Everyone can talk. But if you can show how good you are, you won’t need to.

Show, don’t tell

To succeed as a freelancer you need a marketable skill set, and you must be able to demonstrate that skill set. By marketable I mean something that can help other people get what they want.

If you’re great at writing copy that sells, and you can prove it — what do you think those who want to sell something will say to you?

“Here, take my money!”

That’s what they’ll say.

How to start honing your craft

The easiest way to develop this kind of skill set is to get a job at some sort of agency where you get to practice doing something specific and end up with assets you can demonstrate you worked on (more on this in the next section).

If you’re like me and want to work for yourself at all costs, the other option is to start learning a certain skill set all on your own (of course, you may also have to do this first in order to actually get a job at an agency).

Learning on your own takes discipline and creativity. You have to design your own curriculum. And you won’t get paid for quite some time.

The good news is that the world is complex, and, oh I don’t know … the internet exists! This means it doesn’t take that much to learn something most other people don’t know how to do.

Something I found useful as a beginning designer was the Daily UI Challenge. There’s a similar challenge for writers called Ship 30 for 30. I’m sure you can find one that’s relevant to your domain if you hop on the ol’ Google machine.

With this type of challenge, you quickly end up with recent work you can show to prospective clients. It’s not as good as having actual client work to show, but it might get you in the door.

Whichever way you choose, just remember this:

The goal is to be able to convince prospective clients you know what you’re doing within a certain domain. And for that to be sustainable, you must actually know what you’re doing.

2. Claim Your Independence

Once you’ve acquired a marketable skill set, it’s time to start working with clients. You should do this as early as possible since the best way to truly learn is by doing.

I get roughly 80% of my work from some kind of previous connection — usually someone I’ve worked with before.

This may sound daunting if you’re just starting out. One of the things stacked against you is that you have no history of working well with other people, so no one can recommend you or think of you next time they need the services you provide.

For this reason and several others, including the one mentioned in the last section, there’s one particular path I’d generally recommend to people who want to become a freelancer: Start working at an agency.

I know, I promised you freelancing, and working at an agency isn’t that.

So why am I going on about getting a job first?

Again, you don’t have to do this. I’m simply saying it’s the easiest and often the smartest way to get started. It’s what I’d do If I had to start over. And it doesn’t have to last very long.

By getting a job at an agency, you’ll not only get to develop your skill set while getting paid, but there’s also a perfect way to transition from there into freelancing, which minimizes risk and gets around the networking problem all at the same time: becoming a subcontractor.

Become a subcontractor to claim your freedom

By working at an agency, whether you’re a marketing, design, or business consultant, you’ll gain specific skills and experiences. You’ll also learn about the industry you’re in.

After 10-12 months let’s say, you’ll likely have worked with a few different clients. You’ll have a personal relationship with them and with the people at your place of employment.

If you’re a decent human being, show up every day, and do good work, the people in charge will like you. If they like you and make money from your work, they’ll want to keep you around.

This is the time to negotiate for your freedom.

As always, the more options you have, the better your position for negotiating will be. If you have one or two job offers at the ready, that’s ideal.

This is how you do it:

  1. Tell your employer you’re getting restless, and you’re ready for a change. Regretfully explain you’re considering other options that’d mean leaving them, like going back to school or accepting another job offer.
  2. Reassure them you appreciate them, you like working for them, and you’d like to stay if possible. You just need some change.
  3. As a solution, suggest becoming a subcontractor for them and doing the exact same or similar work as you’re already doing. This way, they get what they want, and you get a little adventure — you get to learn how to run your own business.

If they don’t accept for some reason, another way to do it is to fish for a job offer and then negotiate with the new employer to become a subcontractor directly instead of becoming an employee.

Once you have your independence, you can officially say you’re a freelancer (congrats, by the way!), and you’re free to take on more clients and start negotiating for better terms, higher fees, etc. But you still have the security of your work as a subcontractor. This makes the transition into freelancing easier and less risky.

What about experience?

You might think to yourself, “If this is the smartest way to start, isn’t it better to stay at a normal job even longer to have time to learn and hone my skills?”

Yes, there’s obviously an upside to that. But you have to keep your eyes on the prize here: First of all, if you’re reading this, you probably don’t want to spend years slaving away at a desk job before you go out and create your own freedom.

Second of all, there are many things unique to the context of being a freelancer you simply can’t learn at a normal cozy job. It’s the same thing with being an entrepreneur in general.

This is the mistake people make when they try to eliminate too much of the risk of entrepreneurship — they get comfortable and stuck. Chances are they will never take the leap.

If you want to do your own thing, you’re only taking an agency job with the end goal in mind: to break free as soon as possible. If you feel ready after three months — then go!

Just remember to always stay true to your word, honor your agreements, and treat the people who helped you with respect.

Taking a shortcut

If you’re as stubborn and independent as me (again, I don’t necessarily recommend it) and choose to go out on your own without any real experience, you’re going to have to be more proactive in the beginning.

Initially, you’ll have to optimize for getting work and developing your skill set — not for getting paid.

Once you’ve done some good work with different people and organizations, and new work starts to come in without as much effort on your part, you can start raising prices.

If you choose this path, you have to build up your connections with prospective clients on your own.

I’m not a fan of networking events. In my experience, they don’t often lead to genuine connections.

I think the right way to build a professional network, and the one that’s worked for me, is to play the long-term “infinite game” of always being helpful and staying in touch.

It’s important to note that this is a general life mindset, not strictly a professional one: You never know where, or rather who, the next client will come from.

Other ways to get work

To actually get work in the beginning, you’ll probably have to pursue lots of possible options, both by talking to the people in your network (again, it can be anyone in your life) and by cold calling/emailing.

Some concrete ways through which I’ve found work opportunities in the past:

  • Connect with agencies and become a subcontractor, even if you haven’t worked with them before
  • Look at who’s hiring, and ask if they’re open to consultants as well
  • Look at internet forums and job boards for freelancers/entrepreneurs, like Indie Hackers and Remote OK
  • Work on the appearance of your website/portfolio and your LinkedIn profile to attract clients
  • If you can afford it, try to collaborate on interesting projects with impressive people, even if you don’t get paid (this can lead to paid work later)

3. Become a Business Person

There is another part of freelancing that’s often forgotten: You’re not just a consultant — you’re a business.

Acquiring business skills will come easier to some people. Perhaps your expertise is some type of business knowledge. But many freelancers are creatives of some sort, and I’ve observed a tendency in people who are pure creativity: They don’t want anything to do with the business side of things.

This is a huge mistake.

Let’s get one thing crystal clear: As a freelancer in the free market, money determines the rules of the game. This is not art. I will say it again so you can hear me through the screen: THIS IS NOT ART.

Everything you do as a freelancer amounts to one thing, which is making your client money. Hopefully, your work will take place in a context where there is additional meaning. But you will never escape this fact.

If I design an interaction, it won’t make an ounce of difference how beautiful, cool, and innovative it is if it doesn’t get people to click “buy.”

You may be one of the people who struggle to accept this. Perhaps you believe you’ll be able to create your own niche where this rule doesn’t apply.

You can try, but remember this: It’s more fun and rewarding to win in a game many are playing than to lose in a game you made up yourself.

You are an asset

An asset is relatively exclusive access to something valuable. The more exclusive and valuable — the bigger the asset.

You should aim to become an asset to your clients.

The more unique and valuable your skill set is, the bigger an asset you’ll become. The opposite of this is a generic skill set that’s easy to find and easy to replace.

If you understand how businesses work, you’ll be better able to anticipate your clients’ needs and therefore be better able to help them get what they want. The more you help them get what they want, the more they’ll want to give you their money.

In my experience, a genuine understanding of business can make you into a bit of a unicorn — it’s just that rare in some professions! Developing business skills is often one of the biggest things you can do to become an asset to your clients.

How to start

You certainly don’t have to go to business school to learn more about business than the average person.

I would recommend doing the following:

1. Read “The Personal MBA” by Josh Kaufman. If it piques your interest, go to his website and find what you like in the list of other books to deep dive in.

2. Read “Million Dollar Consulting” by Allan Weiss.

3. If you’re more of a visual learner, you can find tons of business lessons on websites like or

4. Optional but super powerful: While you’re learning, create something in the real world as an application of what you’ve learned. It can be as simple as selling your designs at Teespring. Or if you’ve already started your consulting business, you can apply what you learn to that.

4. Productize Your Services

If I was going all in on freelancing, this is where I’d put all my focus at this stage of my career. Quite frankly, I should have done it even earlier, which is easy to say now.

I think the traditional consulting model based on hourly rates is stupid, and discussing the problems with it could fill several books. So I won’t bring it up here. For now, all we need to keep in mind is this:

Fundamentally, the traditional consulting model creates opposing incentives between the client and the consultant; the former wants good work quickly for as little money as possible, while the latter benefits in several ways from taking as much time as possible and therefore costing more.

The solution? Productize your services.

This creates a win-win situation, and you should do it as early as possible in your career.

Productizing means:

  1. Your clients can more clearly see you as an asset to invest in: They know from the start how much they will pay in total and can easily assess if the investment is worth it.
  2. You can forget about counting every single minute of work you do (for example, should you count the 17 minutes you spent in the shower coming up with world-changing ideas for your client?). Instead, you can focus on getting them what they want, which is always some variant of making more money.

If you can produce a 10x return on your client’s investment, I guarantee they won’t care if you spent two hours or 200 hours on their account. And if they do, they’re not very smart, and you should start working on getting better clients.

However, I’d still recommend going for the typical hourly-rate model in the very beginning, for two reasons:

  1. Most clients are used to it, and it helps to conform to the standards when you’re still a nobody.
  2. It helps you to learn how long it typically takes you to complete certain types of projects, which will guide you in pricing later when you start productizing your services.

Get organized

“At the core, a business is a collection of processes that can be used to reliably produce a particular result.”

– Josh Kaufman

In order to productize your services, you must first see yourself as a business made up of certain processes used to produce particular results. The better you are at defining, structuring, and creating documentation for these processes, the better you will be at creating profitable service products.

If you consistently underestimate how difficult it will be and how long it will take to produce a particular result for a client, productizing will actually leave you with less money and less happy clients.

Different types of service products

Probably the most recognized type of service product is a retainer. That simply means the client pays a recurring fee for access to your expertise (for example, they have the right to ask you questions over the phone for x hours per month).

This type of product is only relevant in some industries and for some projects — and completely out of the question in others. It’s also something you typically do later in your career.

The type of productizing I’ve used most is tiered offerings.

Say I was going to do a user-research project for a client. I could then offer three different tiers:

Tier 1

  • Basic user interviews with participants from one customer segment, with transcripts

Tier 2

  • In-depth user interviews with participants from two different customer segments
  • Documentation of my conclusions

Tier 3

  • In-depth user interviews with participants from two different customer segments
  • A participatory design session
  • Documentation of my conclusions
  • Suggested improvements with redesign examples

Each tier will have a different set price — just like different products.

Notice how you can make some options less attractive, while still giving the client a sense of autonomy.

For example, the first tier in the above example is not really an option for most clients unless they have someone who can interpret interview transcripts in a useful way.

You can use this to drive clients toward the option you want to end up with, which should be the one where the client gets the most value — and consequently where you get paid the most.


Tying It All Together

Freelancing is not for everyone. It can sound sexy, but it’s easy to overestimate the upside and underestimate the downside.

If you want to become a freelancer and do your own thing, it’s crucial to have healthy expectations — whatever you choose to do in life, there will always be hard work involved if you want to do it well.

However, if you’re the right type of person and have healthy expectations, there’s nothing stopping you from going out on your own — even with minimal experience — because you’ll be forced to keep learning quickly throughout your career as a freelancer, probably much more quickly than at a cozy job.

I hope this guide will give you an accurate picture of what it means to work as a freelancer and the confidence to determine if it’s the path you want to choose. If it is, and you follow these lessons, chances are you’ll do well from day one.

Don’t hesitate to reach out or comment with any questions. Good luck!

This article came out of a talk I did in late 2020 at The Media Institute in Sweden.