I am a Digital Product Designer.


Dann—What does freelancing mean to you? I mean, what do you think when you hear that word, “freelance”?

Jared—[0:10] Being a freelancer means having the dual opportunity to help others and to help yourself. Whatever your craft is, whether it's design or engineering, you get to give that to other people in return for something. Money, equity, whatever, but you also teach yourself a lot, because there's a lot of skills required to be a freelancer. And if you're able to help yourself and help others at the same time, and get paid for it, that's a great combination.

Dann—Do you think freelancers need certain skills to become successful?

Jared—[0:34] Freelancing is interesting, um, because it requires a lot of skills. You are essentially a one person business, so, you know, marketing is involved. You have to have avenues of, like, inbound, right, or outbound. Like being able to find your clients or setting up ways for them to find you. Whether that's social media, word of mouth, references on LinkedIn or portfolio or whatever it is. Outside of that there's a lot of operations, so you have to understand how you make money, right. You have to be really good at taxes. If you're not really good, then I always recommend to people to find someone. Which is actually interesting, because it also requires some level of delegation skill, right. Like even though you are one man or one woman person, business, you can still outsource things, right. So you can still contract, a finance person to just handle your books, right.

You can, if you need to, contract marketing to, like, help you get your things out there, at least give you some guiding principles. And then of course there's the work. More required is like the people skills, right. Being able to talk to your customers. Or talk to your clients. Understand their needs. Learn how to tell them that their idea's actually not a good one without making them feel like they're an idiot, but more like you're empowering them. Like, this is what you brought me here for, right. I like where you were going, but it's just the wrong path. So yeah, like, it encompasses all those things, and I feel like the more someone does that, if they stay in freelance, awesome. If they move into any other kind of thing whether it's like a start-up or a full time gig there's a lot of lessons that they take with them to that kind of role.

Dann—Tell me about how you got started and what led you into freelancing for the first time?

Jared—[2:09] At the beginning of my design career, freelancing was all I could do because I didn't have the skills necessary to go full-time. I was brand new to the thing. I felt that there was something I could prove. I felt that there was value I could provide that just wasn't at the level that a company would want to employ me full-time. So that's how I got in. When I felt like I got to the level that I wanted to be at, I applied. Got a full-time job as a designer. After that job I went back into freelancing, and it wasn't, you know, it had nothing to do with the full-time job. It was just a period of time, like. I was like, you know, I want a little bit more of my time back. I want to explore different things, right.

I realized quickly that freelancing allows you to get breadth, and then full-time allows you to get depth.

I liked being able to explore a lot of these things, because when I actually went full-time I had a lot of surface area. It's like, I've seen this before. I was like, the only person on the team, it's like, why do you know anything about e-commerce if this is like, uh, this is like a coaching company, right? Or like, why do you know anything about, like, cars, if this is a health company, right? So that was one of the benefits. Now, I'm freelancing because I feel like I built up a set of skills that I want to share with as many people as possible. That doesn't mean having, like, ten or 20 gigs. It just means having more than one.

Dann—How did you land your first projects? Seems like it’s always the hardest thing to do. How did you get through this?

Jared—[3:43] The first three or four contracts I got in the city, one of it required me to do a lot of work ahead of time. So I knew I wanted to help this company, I knew they were looking for design talent, but I assumed and I was right that they were probably looking at other people who were potentially more qualified than me, or had like, better, like network to that person. So I thought to myself, well, what are the things that those people are probably not doing? And what they're probably not doing is researching the company that they're about to take a contract for, right. And why would you? If you are in the position that you hope to be in, if you're in the position of people always ask you for work, then you're not really, like, hmm, like, what product do I want to improve and do deep research. You just, like, say yes or no, right.

So I looked up this company, um, I looked up all their competitors. I researched the hell out of this company, I researched the hell out of their competitors and I sent them an email. I'm like, "Hey, if I were working on your product, these are three things I'd change right now." Um, and just like general ideas, right. And if they were compelling enough to the person, they would respond. And sometimes they responded because they were like, woah I did not think about that. Like, can you come work on this right now? Um, or they were thinking about that already, but they were surprised that someone who did not have as much institutional knowledge as them could also perceive that, right. So at that point you've already proved half of your value. It's like, the person obviously has critical thinking, and they can figure out what needs to be focused on. The other half is, are they a good designer. Right. And then it's a much easier conversation, and if you were now competing against people who already had a name brand, you are already higher up on the list.

Because what they've already proven is, like, he knows what to work on. Right. Now it's just, like, does it look good? And that's a much easier conversation.

Dann—How do you charge your clients and how did you come up with that solution?

Jared—[5:30] The way I charge is- is there's a system to it, but it's more flexible than others might think. So when I started freelancing, it was just strict. Like I charged hourly, and I had an hourly rate and basically how I came up with it was if I were full-timing at a company that did not offer equity. How much do I think I am worth at a certain stage of- of a business. Um, and then I divided that by obviously 12 months, and then, you know, 160 hours if you work full-time. And then I discounted that by, like, 20%. 25%, because that's assuming you work every single day. And part of the goal with freelancing is, like, you can manage your time a but more. You know, you don't have to like take time off from a job. You just decide not to work for a period of time.

So being true to that, that's how I calculated, and I would just work on an hourly. But what I quickly found is that when you're working on an hourly basis, and as your skill improves over time, you start making the same decisions a lot faster. And, you know, like, an example would be, build me an onboard form. An onboard flow that performs better than my existing. All right. In the beginning, the process is the same, there's research. There's understanding the problem, identifying the solution, et cetera. But in the beginning, you probably spent a lot of time thinking about that onboard flow. And fast forward 12 to 18 months, you're like, I've seen this like 10 times. I can do this in, like, one tenth of the time. Right.


If you're charging hourly, you're making one tenth the money for providing the exact same value to the company.

Jared—[6:01] So I quickly realized that, like, I was actually losing money by charging hourly. So I actually learned from you [Dann] years ago that weekly is where it's at. Right. Um, and the benefit of weekly, you're not- you're not cheating the client, right. Because you were still thinking about it. The difference of, like, year one and year 10 is the amount of thought processing at the desk goes down. Because when you're just walking around, your body and your brain is actually processing the solution. Right. So, you know, year one, you can't do that. Like, you're out, you're playing frisbee or like, you know, with your dog or whatnot, and like, you're just thinking about throwing the frisbee. 10 years later, your subconscious is figuring out a problem. Right.

Why are you not making money for that same amount of cognitive load?

Jared—[7:34] So someone could like, think about, like psychology and pricing, but it's not really that. It's just like, you are still performing the- you're still providing the exact same, um, value to the business. So you should make that money, right. And when you do weekly, there's another benefit to it. Aside from, like, making the money that you should make. It also releases- like, reduces a lot of tension that you have with your client, right. If you're charging hourly and you say, like, you're going to work out of the office for eight hours. Your client is gonna be watching you the entire eight hours. It's like, how long did he go to the bathroom? Was there, like, video playing? Is he on YouTube in there? Right, like, you know. He went out for a lunch, but like, everyone came back in 20 minutes and he came back in 25. To them, they're literally losing money every minute that you're not focusing. Right.

If it's weekly, it's more casual. It's like, all right, like, he popped in for like four hours today. But he was 12 hours the next day. Right. They're looking at it now as like, at the end of the week, did we get the value that we expected. Right. And the goal is to obviously exceed that. Now if someone's like, "Hey, I need help on this thing. Like, 10 hours." Then that's different, right. Because it's literally they define it as 10 hours of work, so I'm going to give them 10 hours of work.

Dann—Do you think you can make a lot of money freelancing compared to full-time?

Jared—[8:32] I think someone can make a lot of money freelancing, but it depends on, there's a lot of factors involved. So location is one. You know, if you're in San Francisco there's a lot of money here. If you are in Wisconsin, there's a little less money there. Another is the kind of work you do, right. If we're talking freelancing in general, I could be a freelance plumber, and you can make money doing that, but it's not gonna be the same as if you're freelance digital tech person. Right. Whether that's design, engineering, product management, marketing, whatever it is.

But talking at least for myself, a freelancer in San Francisco, there's money there. Right. Businesses are particularly beginning to understand the importance that design plays in- in- in a- in a businesses' survival and ability to execute. And because of that, they're willing to dish up more money for it. And another factor that actually comes to mind thinking about business is the stage of the business. Right. If we're talking particularly about start-ups in San Francisco or New York, or- or like tech hubs, if you're doing a lot of contract work with, say, seed funded companies, or pre-seed, like post-idea pre-seed, there's not a lot of money there. Right. Because they're very tight on budget, and you have to, you think of it as like an opportunity cost, right. To them, like, they're dishing out this money, but if they die, like, didn't matter anyway. Right.

If you're post-seed and you have some money, obviously like there's money there, but you're not making what you'd make if you worked at a public company. If you're working mid to- to public company, then obviously like, they have funds and they understand the values. So, yeah. You can- you can build up a war chest. (laughs)

Dann—So, I noticed you don’t really use the term freelance when you talk about yourself publicly, you seem to always say contract instead. Why is that?

Jared—[10:36] I think contract, the term, helped when I was younger because it did sound more official. It- it sounded like this isn't this guy's first time. Like freelance, you never know, like, how someone's- like, the- the next question someone always asks you is, like, how long. And then the next question is, like, what projects right you working on. Right. And, like, you look at those three questions as like how long, it's like, how long, are you serious? Like, how- how long have we really been doing this thing? And what projects, not contracts, right. Projects. Projects sounds like, what are you spending your time on. Like, what are you hacking away on right now. Right. Um, when I say I'm a contractor, people are like, well what are your contracts?

Like, what are- what are these, like, business engagements you currently have? Right. Um, and it matters a lot less now. Like now, I can use them interchangeably. I- I think contracted's just like, my habit now. Um, in terms of like, the word I use. But when I was younger, it definitely added some, like, weight. Sadly.

Dann—Will everyone succeed at it?

Jared—[9:35] Not everyone will succeed at freelancing, and that's okay. Because it's not the only form of work. You can do so many different kinds of things. You can try it out, and you might love it. You can try it out and you might hate it. Right. But you can try it out. I will also say though, that just because you fail at it at the beginning, does not mean that you will ultimately just be bad at it. When I started freelancing I was terrible at freelancing, right. I didn't know all the things that were involved. I thought I just text you and say, like, yeah I'm free. Pay me, and then I'd do work. Right. (laughs) I didn't know there was, like, all this finesse of, like, you know, do you take X amount upfront. Like, how do you charge them if they're late. All these things I learned over time, so by definition when I started I was bad. Um, but I think that I had some of the skills naturally, or I had the aptitude or hunger to actually learn the things that I was bad at. And if you don't have that, then you can try it, but you're not really going to be good at it. (laughs)

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