Freelance by Accident? This Designer Left Tech Giants to Work for Himself
How bootstrapping led to a six figure freelance biz, working only 15 hrs a week. And how you can do it yourself.
Didi Medina is a phenomenal product designer from the A-Teams community, who’s worked for some of the best companies in the world, but one day realized, “I want to go at it on my own.” Check out the top 5 insights from our interview with Didi, and sign up for his workshop if you want to learn more.
Insight 1: Design is people
“Design is people — in my opinion. It’s easy to think about design from a place of what’s possible. But it’s very different to think, “What do people want? What do people relate to? How do people understand the thing you’re designing?” A lot of my designs failed until I learned a decent amount of psychology. And that’s when everything changed — before that I was designing, just using “best design practices.” Things looked good, things animated well — all that good stuff. And then, you’d launch it. And it just didn’t convert. It just didn’t do “the thing.”
Then you get someone from the biz team ringing on your doorbell, a month and a half later, “Oh, we were measuring the performance of the thing you launched last month — you worked on this, right? It’s almost like a debt collector. And I’m like, “Yeah, I made that.” And he says, “It’s not doing the thing we wanted it to do. I’m like, “Oh, I just thought it was supposed to look pretty.” That’s when you start taking a higher level of accountability and figuring, whatever it is I do design — it needs to eventually be used by other humans.”
Insight 2: Fake it till you make it
“I moved out of my parents house when I was 14, and I needed a way to pay rent. So I asked myself, “What is a job I can do that doesn’t need a diploma?” And I landed on photography, because when I was 15 years old, that was the only thing I can come up with. And then once I started getting into photography, I started playing with design tools.
I made a lot of like, fake projects that I put up on my dribbble. And I never told any of the companies that were interviewing me that they were fake. Actually, those projects are probably still there. Never took them down. And I landed my first job as a UX designer when I was 17.”
Insight 3: Sell 150% of your time
“I went freelance by mistake. I’d just moved to New York less than two years ago. And I thought, “What’s next?” I decided, “I don’t know, but I’m not going to another lily pad — another company with status and good pay.” So I left my job and went to Israel to build my own product.
I bootstrapped it. Me and a buddy of mine — we started working on a prototype for a product. I realized I’d run out of savings at one point, so I knew I had to start subsidizing my income. I needed to figure out a way to make enough money to pay just for my expenses.
I asked myself, “How do I make $4,000 a month working 3 hours a week?” So I could spend the rest of my time building my product. I succeeded in that goal — by freelancing. Later, I quadrupled that.
The product I was building was a bust. We didn’t have any backup ideas. And then it occurred to me, if I do more of this freelancing thing, I can multiply that $4,000 a month by four or five and have a salary. I can do that in meantime until I come up with an idea. So I did that.
The trick is taking on bigger companies, instead of smaller ones because they tend to value opportunity cost more than anything. When you work with smaller companies that try to make you allocate every hour of your time, because they don’t know how to think about results or opportunity costs, you can’t sell 150% of your time, you can only sell 100% of your time, and you also get paid less for it.”
Insight 4: Talented? Doesn’t mean you’ll be a great freelancer.
“I think the biggest misconception is you can go freelance, and if you’re talented enough as a contributor, everything would just work itself out. Like you just get paid bank — you’ll get all the clients frolicking to you, and everything will just work out. And it’s not true. It’s so not true.
Most people come from the world of being a contributor — they’re a designer, engineer, or a manager. But when you shift into being self employed, you’re technically running a business of one — but it’s still a company. It’s a company of one. And that means you have to take on a couple of hats. You have to be a visionary, you have to be a manager and a contributor. You realize you take for granted all the resources you have in a company, that made your job possible — that enabled you to do the thing you want to do.”
Insight 5: Your brain can be a fickle piece of shit. Plan for it.
“And there’s the obvious question, which is, “Why do I work by week and not do it by the day?” At least for my line of work, as a designer, something you notice is, your brain is like a fickle little piece of shit. Sometimes we’re creative. And sometimes it’s not. And, you know, when you plan by the week, you can compensate for that.
Let’s say, I need to design a website this week — I can start with finding the time blocks. I can say, “I need to first sketch it out to understand the content and the concepts that are going into it.” Then I’m going to want to give myself at least a day buffer to kind of let it simmer. And then I’ll come back on Wednesday, do an initial draft, then give myself another buffer and then come back Friday and wrap it up.
So when you can plan by the week, you can actually adapt your workflow to work the way you creatively flow that energy out. When it comes to managing my time and my week, I make lists. Make a list of all the things you need to get done. And then after that, make a list of all the time blocks. Try to break it down into chunks of time, then block out your calendar, until you’ve planned out the whole week.”
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