“Calming the Freelance Rollercoaster —

Jonnie Hallman’s Cushion App”


Jonnie Hallman has dedicated the past four years to building an app called Cushion to help ease the minds of freelancers. A long time freelancer himself, he meets the needs of freelancers with useful, smart features and also through giving a digital tool personality and warmth.

At MAEKAN, the story defines the medium. Some stories function best as written text, others hope to capture the emotion through an intimate audio experience. In cases such as this audio story, the transcripts we provide are done to the best of our ability through AI transcription services and human transcribers. We try our best, but this may contain small errors or non-traditional sentence structure. The imperfection of humans is what makes us perfect.

Charis Poon: I work as an editor and producer at MAEKAN, but I’m also a freelance web and graphic designer. When I left my former full time job to get into freelancing, I asked a couple of my friends who were already freelancing (in my mind, they were the pros) for chats over coffee to talk about how they got started and what lessons they’ve learned that make freelancing sustainable. I asked about digital tools for invoicing and got a recommendation that served me well enough, but about a year later, I was looking for an alternative that cost less and hopefully had a better looking interface.


That’s when I came across Cushion, an app that helps freelancers get peace of mind. And man, did I wish I had heard about it when I first began freelancing.

Jonnie Hallman: We have so many people that just say, “I can’t believe I’ve never seen this before. It took me so long to find Cushion. Where has it been?” And you know, I’m scratching my head, I’m like, “I don’t know. It’s been here.” How do I get it in the hands of more freelancers? The people that use it love it. I ask them to just spread it on to other freelancers and that goes a long way.

Charis: That’s Jonnie Hallman, founder of Cushion, talking to MAEKAN Editor-in-chief Eugene Kan.

Almost everyone on the MAEKAN team (and many of our community members) does freelance work and we each have our own ways of coping with the varying workloads, flux of clients, and business aspects of being self-employed. It has proven possible for digital tools to create ease of mind. One of the keys to making it on your own as a freelancer is to lean heavily on things outside of yourself: tools, books, other people, and online communities. All of these things lead to greater success than siloing yourself off.

Jonnie, a long time freelance designer and web developer came up with the idea for Cushion in early 2014 while in the midst of a particularly stressful season of freelance.

Jonnie: Yes, there’s a very definitive moment where I was taking on way too much work without realizing it. I had a problem where I had several clients that I was actively working with. Some were dragging their heels; the others were just starting soon. So I knew that they were going to start and everything started to overlap, but then out of nowhere I had to take a client gig that I couldn’t say no to. So all of a sudden I had way more work than I knew how to handle, but I knew I had to get through it all. So I put my head down for several weeks and just powered through it, but at the end of it I was completely burned out.


I didn’t want to work anymore. I just wanted to take, like, weeks or months off. I just wish that I had something that would’ve told me ahead of time that this perfect storm is going to happen so I could avoid it, so I could maybe find a way to reorganize my time, or be able to confidently say no to a project so that my health isn’t affected by it.

Charis: After this experience he started setting aside months at a time, when financially possible, to work on Cushion with the hope that it might help him regain his personal peace of mind and be useful for others in the same way.

Jonnie: It’s something that I wanted myself. I’ve always had this problem of feeling like freelancing is very stressful all the time. Everyone feels very alone.

Charis: Freelancing is like a rollercoaster with inevitable highs and lows. And even though freelancers might feel alone while working from home, the number of freelancers is steadily increasing. According to 2017 research results produced by Upwork and the Freelancers Union, 57.3 million Americans are currently freelancing, making up 36 percent of the U.S. workforce, and the study estimates that by 2027, the majority of the U.S. workforce will be freelancing. Apace with this growth is the flood of technological tools available. You’ve probably heard a Squarespace ad at some point on your favorite podcast stating that the only difference between an idea and a business is getting a website up.

Jonnie: Freelancers, even though we have all these resources now, people sharing how they become freelancers, all these tools to help you freelance, it’s still very lonely. Especially for people that aren’t in New York or a big city. Like back home where I grew up, my parents are freelancers, but they’re in a town of a few thousand people. Freelancing is not very common there so, like, who do they turn to? And they’ve had to sort of learn along the way.


I’d really like to fix that, along with other things that are downsides in freelancing, but it’s like one step at a time. This is like a multi-decade problem just around everything. I wanted to feel like, you’re thinking about going freelancing, here’s your packet, here’s how to do it, I want that kind of approach. Where it’s a very achievable, doable thing. But it’s still such a—


Eugene Kan: Still a challenge.


Jonnie: Yeah, yeah. Even though freelancing is becoming so popular now, it’s still like where do you start? There’s no clear answer.

Charis: Cushion’s purpose is like it’s name. It’s meant to provide a clear enough picture of how things stand as it pertains to workloads, invoices, budget, and clients for freelancers to feel like they don’t have their backs against a wall; that they aren’t between a rock and a hard place; that they don’t feel as though the proverbial crap is always just about to hit the fan.

But before the app was built to the degree it is now and before two other full time Cushion team members were hired and the team started working out of the co-working space Small City in Brooklyn, Jonnie sat down to tackle just one problem.

Jonnie: I just wanted to know how long canIcoast without having to worry about taking on more projects to earn more money. I wanted to know, “Could I take three months off comfortably?” And at what date do I need to start worrying about my bank account versus just always worrying about it. Even if you’re doing really well as a freelancer you still remember the times that nobody calls. There’s a freelance season where there’s a bit of a dip. So it always freaks you out a little bit, but I wanted something to say, “You’re going to be fine for the next three months. Don’t worry about it, just make sure you’re prepared for this date.”

“I just wish that I had something that would’ve told me ahead of time that this perfect storm is going to happen so I could avoid it, so I could maybe find a way to reorganize my time, or be able to confidently say no to a project so that my health isn’t affected by it.”

Charis: Jonnie Hallman has always been problem oriented. When he experiences something not working well, he takes it into his own hands to make things right, at least as much as it is possible within his ability. For example, the time he created a lightweight Twitter client called DestroyTwitter as a side project in September 2009 while he was still in college.

Jonnie: When Twitter first came out, I hated every Twitter app that was out there. It wasn’t something that I found usable. I saw Twitter as like an IM client or like away messages from back in the day. So I built my own Twitter app that was exactly that and it sort of took off.

Charis: He clearly hit on a pain point that other people were feeling too. At peak usage the service sent out over a million tweets a month. Unfortunately, DestroyTwitter is no longer available because of Twitter API restrictions.

There are two gargantuan challenges Jonnie sees facing freelancers that he might not be able to directly solve. The first one: healthcare.

Jonnie: The biggest thing that I would love to tackle, but not really love to tackle, not be responsible for having to make this work, but be able to affect change in it is something specific to the U.S. which is healthcare. That’s such a big issue. Freelancers are in the worst position for healthcare and it makes no sense. Small businesses, just in general, just the way that politicians talk about supporting small businesses, it really should be a thing where if you want to start a small business you should get benefits, like a leg up, over people that take a full time job. You should be able to do a single payer healthcare. Let’s start it with just freelancers and see if it works. There should be all these benefits to wanting to go out on your own and do it, because it’s such a risk and it’s, you know, you start freelancing and you realize that, “Oh shit, I have to pay how much for healthcare as a solo person and it’s not good healthcare at all.” Yeah, I mean, that’s one thing I wish was just resolved, because it’s not an issue in any other country. We have users all over the world and I talk to them about some of this stuff and they’re like, “Oh, Canada it’s fine,” or here or there it’s no problem at all.

Charis: The second: taxes.

Jonnie: I can’t imagine saying I want to be a freelancer and all of a sudden, like your employer’s been paying their employer tax and taxes are taken out of your paycheck, how are you supposed to know? Unless you have an accountant who’s familiar with freelancing. How do you know that these are the dates you have to pay and this is how you have to pay and you have to pay estimated taxes and all that? I have known so many people who they feel great they got through their first year of freelancing and then they get their IRS return and it’s like, “Oh, you owe the entire year’s tax.” And it either ruins them, deters them from freelancing ever again, or they just have to pay it, and hopefully they set aside some money to be able to cover that.

Charis: Jonnie’s thorough awareness of the whole gamut of freelancer issues comes from growing up in a household where both of his parents were freelancers. His father has been a freelance book cover illustrator for the past 40 years. After college, rather than following immediately in his parents’ footsteps, Jonnie took a full time role at Adobe as a mobile developer and then as a prototype designer. Even though observing his parents’ lifestyles included making note of their anxieties, full time work just didn’t cut it.

Jonnie: Growing up with him, seeing how he was always paranoid about losing all of his clients. He kept a book under his desk of all his book keeping. I was always surrounded by freelancing and I tried a full time job at one point and it just physically didn’t feel good, like I felt uncomfortable the entire time sitting next to a manager knowing that there’s a chain of command ahead of me that I couldn’t control anything. So that just made me think that freelancing was in my blood originally.

Charis: There are useful lessons for freelancers to learn whether they started in the 1980s or are starting now or plan on starting in the next five years: how to organize your life, coping with watching your finances drain, and building a network of people. The main difference between Jonnie’s father making it as a freelancer four decades ago and now is what the internet has made possible: easily accessible resources, support systems, and tools. Cushion takes full advantage of that.

Jonnie: I think we’ve finally embraced the fact that we’re a small and nimble team and that’s sort of our advantage. We look at other competitors and they’re big companies. They’ve been around for ten years, but because of that they have a legacy of ten years to support. So the web was very different ten years ago and the technology that was involved was very different. So now we’re building with tools that let us build much quicker. Just the way I like to work, we like to ship new features each week or each day and that’s sort of unheard of for a lot of these big companies that have to go through meetings and have people sign off on things. So I think for us it’s just something that we pride ourselves on. Being a small team and being able to know all the users personally. People that have been with us for over a year we know them, we know their name. Chatting with them is more like talking to a friend and getting their feedback.

Charis: This is what makes Cushion unique. Sure, Cushion does a bunch of things well: forecasting, tracking invoices, highlighting work overload, and visualizing budgets, but this is Cushion’s “special sauce.”

Jonnie: You want to be working with something that feels familiar, you want comfort. So I think having a face to a tool rather than being just a blank spreadsheet or something goes a long way to feel like, for people who don’t live in a big city, that at least they have somebody sort of guiding them through building this tool. And I think that’s something that I’m proud of, being able to be very transparent with what we do.

Charis: From the first day that Jonnie registered the domain name cushionapp.com, he has kept a blog, and then he added a journal to document the process of planning, designing, and developing Cushion. The website has a page that shows running costs down to the cent and there’s a changelog with every single developmental change to the app since 2014.

Jonnie: You know, sharing our running costs goes a long way. We get featured everywhere for that kind of stuff, because it’s something nobody else does, which surprises me too. We just came out with a new page on our website that’s just revealing our purpose. We want to be a sustainable business. We want to be a small team that works really efficiently. We don’t want to be a start-up that’s looking for an exit. We’re in it for the long haul and we want that to be very apparent. So just being as honest as we can with people, I think will go a long way.


Eugene: Is that at all challenging?


Jonnie: No, I think it’s the easiest thing in the world is just being honest.


Eugene: And is that pretty inherent to your personality?


Jonnie: Totally. I don’t hold back with talking about things or sharing things.

“We want to be a sustainable business. We want to be a small team that works really efficiently. We don’t want to be a start-up that’s looking for an exit. We’re in it for the long haul and we want that to be very apparent. So just being as honest as we can with people, I think will go a long way.”

Charis: It’s been really easy to talk to Jonnie via Cushion customer support. In fact, that’s how this interview with him got locked down. The typical digital service user might dread having to contact customer support, but Cushion support is a whole different ballgame from the kind that involves hold music, listing a string of customer ID digits, or filling out post-support interaction questionnaires.

Jonnie: From my perspective it seems like start-ups that are on that path of, you know, taking C rounds, Series A, Series B, support starts very early where they’re like, “Okay, we’ll have a support person,” once they get to a certain stage, but I want to keep this going as long as I can. I love talking to people because it’s instantly like I can instantly respond to them, give them an answer, make them feel welcome, and then I learn from it too. We’re learning so many, like, what are the features that people like, what are the things that keep them coming back to Cushion, and sometimes it’s not features, sometimes it’s just the way that they feel using it, like a comfort level. And that’s the kind of stuff that wouldn’t get back to us if we had a layer of, like, a support team just fielding stuff and giving a summary.

Charis: This is how the app has taken form over the past four years.

Jonnie: We like to just say, like, “What do we want as freelancers?” and there’s a good chance that it’s going to resonate with other people. We certainly take a lot of feedback from people that give us suggestions and then we shape those to the way we think that should be implemented. There’s a lot of hopping around. We don’t settle with one idea for months at a time. We don’t set these road maps that are set in stone. We like to just change things up along the way and think of it more as this fluid, ongoing process of shaping the tool, instead of just saying these are the features and then we’re done. I like to feel it out and say we can tweak this thing a little bit or this would be useful.

Charis: A picture of Jonnie’s work life comes into focus. He and his team hop around amongst a variety of developing ideas; they’re shipping features every week, if not everyday; he’s personally providing online customer support to all Cushion users and writing about the experience regularly.

Jonnie: I kind of miss having two to three months off. But at the same time, when I took that time off I was working on Cushion. I think personally for me I need to be working all the time. It’s sort of what keeps me sane and feeling, like,productivity, feeling productive, gives me energy. So, I get excited about building stuff and sometimes I get antsy on vacation when we just have to sit somewhere nice by a pool or something. I like it for a week or so, but I’m ready to start working again. I think it’s . . . I don’t know, we’ll see, maybe now that I’m getting older, I’m not like when I first started I was in my twenties, now I’m in my thirties, it might change. What I find valuable might be a little different.

Charis: Despite his clear love for constant work and productivity, (anecdotally, Jonnie really did once answer a support request from me while he was on holiday) Jonnie readily talks about the personal toll of weathering the ups and downs of running a small business.

Eugene: Looking back at something you wrote in 2015 that pertains to sort of the emotional swings that come with doing this, do you think you’ve developed a sense of emotional fortitude after all these experiences, like almost being battle-hardened?


Jonnie: Totally.


Eugene: Is there a process to that? How would you—


Jonnie: I mean, just being numb to it. And that’s just a freelancing thing. I had that when I was freelancing, just being able to say, like, my bank account is draining right now and I’m okay with that. I need to focus on finding more work and doing that kind of stuff. And that translates right into running an app. Being able to pay people and watching the company’s bank account drain while you’re trying to find new users or grow the business itself. It’s definitely . . . I mean, I still feel it. I still have those ups and downs. I have a supportive wife who’s also a freelancer so she definitely knows what I need. It’s just finding the things that put you in a calmer space or it’s sort of like, just not thinking about the things that are really stressing you out and just trying to focus on what gets you out of that.

Charis: If users like Cushion, there’s a good chance that they would like Jonnie as a person and if you know Jonnie personally, there’s a good chance you’d like Cushion. The product is very much a part of himself. It can be draining and a wellspring of concerns, but it’s also a source of excitement and energy.

Jonnie: All I want is just for Cushion to be my career, to be able to have a full time salary that is paid for and have a team that is doing the work they enjoy doing and getting paid well for it. Beyond that, I just want to have a good quality of life, be able to travel, be able to not stress about work, but still be able to work and enjoy it and be excited about it. You know, I worry about the day that it comes that I’m just not into it anymore. It’s been four years now and I’m just still so excited to work on Cushion. That tells me something, whereas before you know I would have a full time job for a year and just be totally over it. It helps that this is my baby. I think this will keep me going for a long time.

Charis: Using the Cushion app has shown me in comforting graphics that I can worry less about my finances and that I should be more careful of when I’m overworking myself. Getting to know Jonnie through support channels and through putting together this story has shown me that sometimes when you really love what you do, you might wind up giving it more of yourself than would be advisable, but the returns you’re investing in is shifting the system of how things are done for a growing demographic. The bet being made is that stressed freelancers will rest easier and pursue new possibilities more.

Jonnie: I want to see it where freelancing is the norm and starting your own business, starting a small business is not something you say like, “Oh, good for you, you’re thinking outside of the box,” all that kind of stuff. I want it to be like, “Oh cool, what small business are you starting.” It should be the norm.