Johan quit his job as a designer a few months ago. He replaced his salary with consulting on design and strategy for startups. I chatted with Johan to understand what had propelled him to make this decision and how he got there. Let’s get started!

Dipping toes in the freelancing water

Kenny: Let’s start from the beginning. When did you quit your job?

Johan: Around four months ago, I was still a full-time employee. I jumped through many, many jobs over my career. Different full-time roles in different design positions. A few years before quitting, I tried to go freelance, naively thinking, “I know how to design so I know how to run a business.” But obviously, it’s two very separate things. During that time, I tried a few things, but it didn’t quite work. So yeah, it’s four months in now and I think I’m doing well so far.

Kenny: So, definitely not your first rodeo.

Johan: I’ve always freelanced because I’ve never got full satisfaction whenever I work full time. There’s no perfect job that can give me what I want personally. So I always chase something else after hours, whether that’s illustration, art projects, or working with clients on branding and website work. My 9-to-5 didn’t have too much of that. I enjoyed just meeting new people, solving problems, and doing things.

Kenny: I imagine it’s a bit more fun as well, right? Because if you’ve been in a full-time job for many months or even 2-3 years, then you know everyone, you know how things work, and you don’t necessarily choose the projects you work on. But with freelancing on the side, you get to jump on different projects and I’m assuming you get to choose, those freelancing gigs, what you’re working on or what you want to do.

Johan: 100%. It’s aiming to get more control over your life. I was in a design job for 6-7 years and I knew it wasn’t a job for me, but I was just there because I was comfortable. I enjoyed life outside of work, but looking back, I was there for too long. It’s as if I was in quicksand, slowly sinking.

Kenny: After that many years, you just don’t have excitement for it. I’m guessing everything is exacerbated. All those things you don’t like are just becoming bigger and bigger.

Johan: For sure. In that job, I was looking for opportunities to change or implement new things. But the place wasn’t super responsive to that. And so, at that stage, I was like, “OK, I need to make a move.”

Conversations with the family before the plunge

Kenny: How did that go, pulling the trigger and freelancing? How did your family receive this? There’s deciding for yourself, but then there’s the decision’s impact on your family.

Johan: I’m very lucky that I have a wife that’s very supportive and I guess my kids are young enough not to know any different, to be honest.

But what I did was I jumped between two or three jobs where I stayed for a year or so. Every time I moved to another job, I thought, “This next job will help me feel more fulfilled.” But then I realized no job would ever give me that. So I had this plan. “OK, within the year, I will leave. I’ll go freelance and do my own business.” And then one of my clients, a freelance client that I did work for, said, “Hey, you helped with our branding for a startup. Would you like to join? But I understand you want to build your own studio. So how about my offer is for you to consult or contract with us for half the week.” I could have a safety net. The other 50% of the time, I’m able to build more with more stability. By that time, I had contract work signed up for 2 or 3 months. I felt that confidence to be able to say to my wife, “Hey, this is what I want to do.”

It’s been nice. Because when I tried to do freelance last time, I felt that desperation to win every every client, every sales call which wasn’t great. I think people can tell. So yeah, part of the safety net was that I was able to breathe a little bit and be able to perfect the other side of the business.

Kenny: When you first tried freelancing, did you have kids before?

Johan: When I first did it, no, I was like, “I can do this. This is easy.” 2 or 3 months later, I’m like, “OK, I’m poor. I can get a job.” But I was lucky that my wife had a great job, at least a good stable job. And there was a timeline to it, right? If it didn’t work, get another job. That was fine. But now that we have kids and the mortgage, it’s a lot more.

Kenny: Different situation for sure. You can’t just jump and do it. How do you feel about that with your expenses and kids? Do you feel comfortable or do you feel a bit uneasy, a bit nervous at times?

Johan: Yeah, it’s funny. It’s probably a mental thing. Because knowing that with this part-time role I have, I know the client is always there and they’re still building. That’s a good safety net. I could always get more hours, but it’s not what I want to do.

How do I beat away the stress? I have to have confidence in myself. I like to be honest. The more projects you win, the more work you do, and the more you have confidence in the fact that there is a market out there, and I know how to speak to them. Although, to be honest, I’m still experimenting. I have to believe:

  1. One, not be so naive and know it’s just design.
  2. But to also have that belief that I can figure it out.

Kenny: How did the conversation go with your wife? What about your kids?

Johan: The first time, it was less of a conversation, it was more of a “you got to give it a go,” and we had less responsibility. We were young, and I could always find a job.

But the second time, there’s more risk, more on the table. I didn’t really have to talk about it with the kids because if anything it was a benefit to them because running my own business and being at home without having to travel to the office or having weird hours to work. It’s better to be more available for them.

But the conversation with the wife was more objective and looking at the numbers. Guaranteed X amount from this person. I have at least two or three months with this client for X amount. Once I was able to prove that, hey, I can match or get close to what I’m getting in a full time role and it was quite stable, then it made the conversation easier. It was good to be able to do that. Luckily she also has a great job. So, we’re a partnership. If she wants to do the same, then we would have figure out how that works.

Definitely the first time was more emotional. “I need to do this.” Second time we have to be a bit more rational. “I need to do this and here are the numbers.”

Try it out or overthink it

Kenny: When I started, I didn’t know what I didn’t know. That adds up to the nervousness. “How am I going to do it and figure it out?” Doubts creep in. Whereas if you found a few clients and did a few projects, you’ve gone through a few cycles. You know what to expect. You know to expect that your sales process can be very slow whereas sometimes you get super busy. You have a better sense of how things go. You also get the confidence as you said, “I figured it out once, I can do it again.” And the more you do it, the more confidence you have because you have more proof of success.

Johan: There were clear boundaries when I went to college, and you know how you succeed in school. But, how do you succeed in business? That was the first part of figuring out the guidelines and where I’ll succeed. “I’ll try this and I’ll try that.” And if it doesn’t work, you have to be open and pivot. This is why I say it’s not just design. It’s all the other stuff around it.

Kenny: I was thinking about just that today. You can read so many different books about business and even freelancing. But there are just so many ways to do it already. So many ways to find clients, so many ways to sell your services, so many ways to set your pricing. There’s so much to figure out it can be overwhelming and stressful.

Johan: You’re paralyzed by the choice. “I want my own choice. I don’t want a job.” Here you go. Have all the choices you want. Good luck with that.

I’ve read so many books that give you theory. But it’s just the doing that gets you there faster. You have to do the work to see if it’s true and if it works for you and your situation.

The perfect job doesn’t exist

Kenny: How did the seed get planted in your head to go build your business?

Johan: 100%. I left one job, which is great, but then it was hard for me to maintain the amount of intensity with the contract at the same time. I moved to a recent job, which was lower intensity, but a lot more meetings and less productivity. I felt I was wasting my time.

That’s when I said there’s never going to be a perfect job. I can’t rely on someone else to give me that. If I want to design the life I want, then at least take control over how to get there.

That was the pipe dream. Working in an agency before, like two jobs ago, I was in an agency and I could see more and get closer to how it works and client conversations. The more you’re part of that, the more educated you are, and the more you have under your belt.

Kenny: What I’m hearing is that the risk was quite reduced for you. You had some learnings as a freelancer previously, you worked in an agency where you took part of client conversations, and you had that part-time contract aligned. Still a leap of faith but it was quite safe with everything considered.

Johan: For sure. Though, to be honest, around that time, people were getting let go from their jobs left, right and center. A redundancy happened in the company I just joined, within a week. Soon after, like a few months later, it happened again.

I do believe in this idea of small bets. At that time, I was not living that philosophy. I was “all in” in that job. Daniel Vassallo talks about how employment is actually risky. I’m giving the control of my time and money to someone else. They can let me go with a two-week notice or none at all. That doesn’t sit well with me. The less risky thing for me, at least in the long term, seems to be going out on my own.

Kenny: You’ve been going from job to job trying to find the “perfect” job. How do you feel now that you’ve been a few months in? Do you feel self-employment fits you? Is that grass greener on that side?

Johan: That’s a good question. I don’t feel I’m there yet. But I also know how that there is more possibility for me to change what it’s like. I have control of the wheel or the levers and to be able to get there. Yeah, the grass is definitely greener on this side, at least for me. To follow the metaphor, I just need to water it more. There’s more shit I have to do, more manure to put on the grass. Part of that is shifting my mindset. There are people less skilled than me doing this. And it’s because they notice certain things that I don’t and I need work on that.

Compounding effort

Kenny: I never really understood when people said, “There is no better time to start than now.” I always thought that’s some sort of motivational platitude. The more I’ve tried building my own stuff, the more I see it actually makes sense because there is an opportunity cost to keeping your job. You’re never going to be in those situations and you’re never going to figure them out.

The more you stay in your job, the less you develop those skills or practice those scripts that you need to develop to figure out the situations and what to say to solve the situation. You just don’t practice making those decisions

Johan: It’s like compounding effort. The sooner you invest in this life, the more time you have to put into it. Doesn’t mean it’s too late at any stage, but by staying with it and working on it, you’ll be a lot stronger all around.

Kenny: You’re flexing that muscle.

Johan: Before, in my job, I would design 70-80% of the time. But now, it’s more like 40-50%. And getting close to a similar amount of money. But there’s also all this other stuff like business development or reaching out. You realize you can be a lot more efficient or get to a point where it’s good enough.

In a 9-to-5, you aim for this perfection because if you have 8 hours to get this design perfect, you’ll spend the 8 hours on it. But you become more execution focused and understand the brief a lot better. So you get trained to see things that are the most valuable thing to work on and you work on that. You get to be more critical around certain things and communicate to the client, “It’s not an efficient use of your money or my time to do this.”

There is no safety in full-time employment

Kenny: How did you feel when you had to quit your job? Were you nervous or indifferent because people were made redundant?

Johan: It’s funny how it happened. But I was happy. I was really excited to leave because I knew I was going to do it. I thought, “This is the time.”

I told my manager and they said, “OK, I’m sorry to see you go. I wish you’d stay, but I totally understand.” And literally, the next week, 2-3 were let go from my design team from another round of redundancy. I might have passed through in that round. I think I would have. But it was great confirmation for me that things are never as stable as you think it is.

Kenny: Like the universe telling you you made the right choice.

Johan: Exactly. If you’re walking around, and everyone’s getting like let go left, right and center. There’s got to be some concern. At first, maybe you feel invincible, but, how far can you go? No, I think that’s why I was just feeling a lot of excitement.

Keep your pipeline going at all times

Kenny: When you’re starting something, you’re excited, and there’s, almost inevitably, the moment when the rubber hits the road. It starts becoming real. In the last few months, when that happened, what was your lowest moment? A moment when you realize, “Wow! This is hard.”

Johan: Definitely, there was a point where I finished a couple of client work and that month was the best month I’ve had. Quickly after, I realized that the pipeline was dry and I didn’t really have as much for the following month. I felt concerned. I thought, “What can I do?” There was no magical shorcut like “I just got this person to get more work.”

So, I reached out as much as I could to ask for referrals. It wasn’t a good month, but you never know where it will come from. As long as you’re consistently reaching out and doing your work. I had random referrals come in the next month, which helped me out. Maybe I was just lucky. What I’ve learned from that is I can’t rely on the current work. I have to be consistently doing and building stuff.

Kenny: Once it’s over, you don’t know if they’re renewing because I’ve seen that also with people. They tell you there’s a ton of work. But something happens in their world or their company, and in the end, the project turns out not to be their priority anymore.

Johan: I really want to implement a strategy you mentioned in our conversation. You were on a certain platform, and then you want to build something else beyond that. What is that for me? Referrals can only get you so far. I’m looking at playing the long game. It could be more articles or SEO or more cold emails.

It’s funny because I started posting more regularly on LinkedIn. Not that I got direct jobs out of them, but just from doing that, people I used to work with were able to refer me or speak to me or a restart conversation. It’s less direct, but being more in people’s faces helps.

Kenny: The lesson here was to do a little bit of outreach now and then and keep in parallel.

Johan: Yes, LinkedIn content, cold DMs and reaching out for connections on LinkedIn. That’s all I’ve been doing. I need to turn that dial up a bit more. Those things have definitely helped.

Cultivate relationships

Kenny: I know you have a coach and you’re part of a design mastermind. Did you have that at the time? Or were you facing that dry pipeline on your own?

Johan: It comes back to this whole thing of the guardrails and having someone to help guide about the best way forward. Yeah, I’ve joined a mastermind ages ago and it helped me when I tried to freelance back then.

More readily now, it’s also having conversations with people ahead of me and saying, “I have this problem. What would you have done, or what do you recommend?” Just being part of different groups and having conversations has helped in general. Once you realize you’re alone, you feel less scared to reach out and be more open. In a job, I felt more closed to go, “This is my dream.” I had thoughts like, “Don’t ruin my dream.” But now that I’m out, I can’t do this alone. I’m open to help. But, I’ll try to be helpful to other people. It has helped lift the spirit as well.

Kenny: When you face something alone, I don’t know why it makes it way bigger in your head. Whereas when you realize someone’s going through the same thing as you and they overcame it. It lightens the load, “Okay, it’s not that bad.” Obviously, it’s still a big deal because it’s affecting you emotionally. But it lessens the burden.

Johan: Totally. Some of these groups have weekly calls, and people talk about their problems. The guy running it shares his insight. But other people also come in with ideas and thoughts. It’s nice to know you’re going through this with other people.

It’s another way of getting referrals. We all have our own kind of niches. And I truly believe it’s all about relationships. As big as the Internet is, with the 1:1 relationships that people have, you can more readily recommend someone. I could recommend you to someone who needs automation expertise. Because I know you through our conversations and even though you’re on the other side of the world. In general, those 1:1 relationships will help.

Kenny: Especially in your line of business with high-ticket services. You’re not sending a 5 bucks e-book. The relationship and rapport are crucial. Because it is a lot more money and you also work longer with people so you need to get along well enough to make it work.

Johan: Referrals are great. It’s the easiest shortcut to get trust from someone. I can do great work with someone and they can refer me to someone else. A referral is like reducing the risk straight up. I’m all for keeping relationships open all through the work. Even beyond that, we’re all humans and we want to help each other succeed. And that’s really important.

Kenny: How do you keep in touch with people? Obviously, you build rapport while working on the engagement, but what about after that?

Johan: Sometimes I see an article or a new product or something else and I’ll email them. “Hey, this reminded me of you. How are you doing?” Or, I check in on the work we completed last month. “How’s things going? How’s it tracking?” But even with LinkedIn, sometimes I’m curious to see how people are doing. I DM them out of the blue for no reason. “Hey, how’s things? It’s been a while.” You start conversations. Maybe I’m just a sucker for conversations. I’m stuck in this room by myself. I want to talk to people. That’s a huge part of it.

More profits and less time on client work to build products

Kenny: Anyway, what’s next for you? I know you were crafting your offer. Where are you on that? You were talking about small bets. Do you have plans on building something on the side?

Johan: The massive goal for me right now is to remove the time I need to spend on the lower-level stuff. Ideally, to get help with some of the organization, some of the junior level design work so that I can help more on a top level and to get more time for myself to even speak more strategically.

But also, a bigger goal is to create something that is more service-based, more of a product, more of an experience. I’ll share with you once I get a clearer picture on that. I see this as a vehicle to get myself more freedom of time because it has the largest potential of leverage to get myself more time to build other small bets. For sure, I do have a few ideas, but I can only do that once I’ve cut the amount of wasted time and get more profit with less time. I’m trying to figure out that situation. How do I get the same amount of profit within half the time? That’s my current challenge.

Kenny: What I’m practicing is having conversations with my clients about how much they value what I’m providing. And to frame my value in a way that is not necessarily tied to the time spent on the project.

Johan: There are different ways. The question I got in my mastermind was, how can I deliver the same amount of value in half the time?

I audited how much time I spent and how much revenue and profit I would get for that. But I had to ask myself, “How can I deliver in half the time?” I audited all the steps and the deliverables I provided. And so I’m picking up some ideas on how to remove myself or systemize. For example, recording a Loom video for onboarding to slowly remove myself from those tasks.

Kenny: Yes, you can think about it as “the work that I do and its impact is the only value I provide.” It’s obviously much more than that, right? It’s project management as well. It’s how you collaborate with the client. And, like you said, the onboarding experience. How smooth and how pleasant is it for the client? And that also provides a lot of value because if it’s super clunky, it appears unprofessional, and it’s not a great first impression.

Johan: Definitely. It’s also similar to the job experience. If I work 9 to 5, I’ll spend 9 to 5 to get this one button done right. But how do I cut the stuff that doesn’t need to be done either? So there’s a few different things. It’s duplication but also value. So it’s a big question. That’s where I’m at at the moment. How do we get so close to the ceiling and then how do we remove the time connection?

Kenny: It might be the hardest because it really is a mindset shift. You need to change all those habits or ways you think, switch that, and reflect, “Okay, I used to think like that, but now I need to gain the habit of thinking differently and asking different questions.”

Johan: It’s very true. It’s almost a personal thing. It’s probably less about the client as much as we think it is. There might be guilt. For example, how can we charge X amount when you’ve done something in one hour? I don’t know. There’s definitely this kind of personal bias to it. It is a challenging problem but a good one to have.

You can find Johan on LinkedIn, Twitter or check out his consultancy website Tension Studio.