Freelancing Lessons
Freelancing Lessons My First Year
If you're thinking of going freelance, this next blog's for you. It's a guest post by Sven Lenaerts - a super talented and (in the nicest possible way) crazy Belgian, currently working in NYC. He's an expert in product strategy and specialises in improving the conversion of digital products. Here, he shares some of the lessons he learned during his first year as a freelancer. Lessons he learned the hard way so you don't have to.

Guest Post by Sven Lenaerts

Are you a freelancer? Awesome. Me too.

I’m Sven, I’m a 21 year old Belgian living in New York City and I work as a freelance UX designer. I focus strongly on conversion optimization and help businesses achieve their online potential. Shortly before I dropped out of college, I started my freelance business Umber. In my first year, I learned some very valuable lessons, I’ve summarized them in this post.

Oh, spoiler: Things didn’t always work out.

The education model is dead

July 2013

In July last year I started my business. There were a couple of reasons I took this decision and I neatly summarized them in a Medium post called: “The education model is dead.”

That’s a pretty bold statement for a naive student. In essence, I was tired of how the system wasn’t setting me up for a successful career in the digital industry. I was in my second year Interaction Design and I was frustrated. There were classes I was correcting my teachers. Progress in my education was too slow and it wasn’t teaching me the particular skills I was looking for. Studying in my spare time was more fruitful than spending time at school.

Naively I thought I could do it all better. How about starting a business? I was going to interact with real clients and learn how all of this works. After all, the crux of college is to monetize your skills, isn’t it?

Actions followed my words. I filled out paperwork and soon after I had my own business. I got my VAT number, hired an accountant and started looking for clients. Studying full-time, running a business and attempting to have a social

life requires careful planning (and a lot of coffee). It was the start of something awesome. Hopefully.

Lesson 1: If you’re no longer getting out of it what you’re putting into it, it’s time for change.

The power of writing

August 2013

I always wrote a lot. I published my thoughts about the industry, some tutorials here and there and I got extremely fascinated how user experience and conversion strategy works.

Writing about my experience and knowledge helped me to find clients. Whenever I approach potential clients, I always sent links to some of my writing work. It helps showing that I’m capable of the job.

Initially, I wrote to help me pay my bills. Later, I discovered it’s a great marketing tool as well. Writing landed me my first couple of gigs. Later that month, Fueled, an award-winning app development company in New York asked me to come work for them as product manager. At the end of August, I moved from Belgium to New York City to take my career to the next level.

You might wonder, how did I get a call from the other side of the world? Fueled’s director found my article on the future of interfaces and gave me a ring. Write.

Lesson 2: Start to write, create, build.


September 2013

As I started to get some gigs, I made the classical mistake every beginner makes: I undercharged.

I didn’t do my research and gave a number I thought was right. Then you learn about taxes, the accountant you have to pay, overhead.. and you realize financially there’s more involved than you’d think.

It’s a lesson I learned very quickly and it made me realize which is probably one of the most important lessons within this industry.

Lesson 3: Never forget you’re running a business and your income depends on how you run it.

Building a network

October 2013

As a student, I took a lot of opportunities to participate in design contests and in general just meet people whom I believed are relevant to what I do.

I suck at networking, but my work spoke for itself. As I won a couple of smaller awards, I got in touch with valuable people. This would become the foundation of my professional network and that would ultimately lead to some smaller gigs. For someone starting out, that makes a big difference.

Best of all is that I learned that most of your networking happens outside of the professional environments. Something as simple as being nice is a way to build your network. Listening to designers is building a network. Giving advice to people is building a network.
Your peers, especially in environments such as college or your job are very valuable relationships. Treasure those relationships.

Lesson 4: You’re already building a network, right now.

The Struggle

November 2013

If you’ve read the wonderful book “The Hard Thing About Hard Things” by Ben Horowitz, there’s a chapter he speaks about “The Struggle”.

Every freelancer knows the feeling. There’s a moment, a couple months down the line you question your decisions. You question why you got into this and why you made sacrifices to try and make this work.

I learned that success is temporary. It can be quiet in between new projects and that can be cruel. You will question your work. You will see better designers. Cheaper designers. Cooler projects. Clients who stay quiet after you sent a proposal.

Some months, are just plain awful.

Lesson 5: The Struggle is real.

Dealing with famine

December 2013

When people speak about freelance, often you hear it’s feast or famine. A middle ground rarely exists.

Once there’s no work and bills come in, being a freelancer becomes tough. I’m lucky to have another job I can rely on, but it still hurts to see income being stripped away because I’m doing a bad job at managing my business poorly.

I took failure to land new gigs personally and that’s not the best way to deal with situations like these. Over time I learned that there are far too many external factors which influence your success as a freelancer. I knew I had to figure out how I could make this work. There will be bad times and you need to be prepared for them.

I have a list of projects I want to work on when I have no client projects going on. You can keep yourself busy with projects which also benefits your business. Write. Build. Create. Don’t put business development aside.

Lesson 6: Winter is coming, be prepared.

Nail down your process

January 2014

As you freelance more, slowly you start to figure out a process which works for you. I took time to really figure out how my process should work, how I should be able to handle multiple projects at the same time and in general how I prepare projects, onboard clients and create the deliverables.

I learned to end every day with a mise en place for tomorrow. In the same way professional chefs organize their ingredients, I organize my calendar and my projects. It makes your day go much smoother. It saves me time on project management which means more time to work on actual deliverables for clients.

Lesson 7: Do your daily mise en place.

Mastering business development

February 2014

As I started to formalize my process, I took a step back and viewed my freelance career from a holistic point of view. I realized, a lot of similar freelancers are out there. There are without a doubt better designers, and there are definitely cheaper ones.

I needed a niche.

A unique selling proposition.

My differentiating factor.

(Enter buzzword here)

I figured I have a surprisingly strong business-oriented perspective on the work I do for clients. When I design a website, I understand they are investing money and would like to see a return on investment. I knew that by providing my insight, as well as focus on conversion strategies I was making my services more attractive. I also wanted to provide clients transparent pricing and a breakdown of where the money is going to in a project.

And.. it worked.

I tested my strategy with a particular client who requested a proposal. I had limited bandwidth, but it was a nice opportunity for me to do some testing. I sent my proposal, doubling my usual rate.

I got the job.

the client admitted I was expensive but I provided more value than cheaper options. In nearly every proposal I experiment with my rate and my sales pitch. As I win and lose for a variety of reasons, I gain tons of knowledge which helps me for future proposals. I’m at a point now I feel comfortable asking for more money if it makes sense and if I lose the pitch I don’t mind - it’s part of freelancing.

Lesson 8: Never forget you're in sales. Don’t just be different, be valuable.

Working too hard

March 2014

As everything started going a lot more smoothly, I made another classical mistake beginners often make. I didn’t say no to projects when I got an inbound lead with a good fit in terms of budget. I didn’t want to lose out.

I love the hustle, the hunt for the next project as I got better at sales. But, I ended up without bandwidth to actually finish the work as I closed more deals. I didn’t have time to properly hang out with friends or have fun. It didn’t take long and I got burnt out as I worked hard to try and make it all work. I didn’t
want to lose my reputation - one of the most important things you have as a freelancer.

I had to learn to accept that things don’t always work out, even though there’s a perfect fit. If you can’t, you shouldn’t.

Lesson 9: Say no.

Find that special client

April 2014

There will come a time that you’re involved in engagements which are very exciting and fruitful. Clients who become friends, who pay their invoices the minute you send them (I’m not even exaggerating here) and refer other leads to you. Heck, I can even curse on our Skype calls. These clients aren’t a myth.

Treasure them. One client made a huge difference for me. The engagement went beyond the initial scope and we’ve been working together for a couple months now. It’s a great experience. Plus - they referred more work to me from other people.

I deeply respect clients who understand a professional relationship is something which grows and I’m ready to go the extra mile for them. Every client has the opportunity to become someone meaningful in your personal and professional life.

Lesson 10: Make clients and friends.

Getting fired

May 2014

I was in heaven. Client work was going smooth, I had some really cool projects lined up and I was working together with awesome people.

Then, a client fired me.


The relationship was pretty smooth so far. Our calls were good and in general I seemed a good fit for what the client was trying to accomplish.

Though, I was in a busy time and I didn’t have enough bandwidth to deliver often, which was part of their expectations. When I delivered, it wasn’t really what they were looking for either. We didn’t got synced properly. I screwed up. I got fired.

It wasn’t a bad breakup, but it was pretty eye-opening. It was the first time I disappointed a client in terms of my work and I was in a position I couldn’t do my best effort even though that’s what the client deserved.

I made a crucial mistake and it learned me a lot. In the end, it was the best for both of us.

Lesson 11: Sometimes it doesn’t work out. Learn what went wrong.

Hitting my plateau

June 2014

More clients started to appreciate my work and I got more opportunities to be involved in projects which interest me.

I learned that I can’t do it all. I can’t keep growing vertically. There are only so many hours in a day. I will need to scale horizontally and collaborate with other people to make it work.

At least, that’s something I’m trying to figure out right now. How can I handle projects I don’t have the bandwidth for to create the actual deliverables, but be involved as art director? Should I hire people? Work with other freelancers? It’s an interesting problem and truth to be told, I don’t have an answer yet. I haven’t learned my lesson here yet. I’m working on it.

Lesson 12: Scaling vertically is limited, horizontally isn’t.


12 months later it has been a helluva ride. I got in the game to focus on my personal growth and learn how to be a better professional designer.

Still, I’m struggling to figure it all out. It’s still hard for me to say no to clients. Or to set more realistic expectations in terms of bandwidth. I still take failure personally and I still realize I’ve got tons to learn. I don’t have it all figured out yet.

That being said, I learned more than any college could teach me. I’ve enjoyed so many things on the way. Both in freelance and life, the best is yet to come.

Want to know more about Sven?

When he's not freelancing Sven works for Fueled - an award winning app development company in Manhattan, New York. Follow him on Twitter and check out his portfolio for more.

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