Freelance as Lifestyle Design PT I: Doing More With Your Life


How does that sentence make you feel? I’m assuming reading it, you started to get a little defensive. No doubt it conjured to mind a few dreams of your own that have yet to become accomplishments. Those hopes of yours that remain fantasies, ensnared in lists of excuses; every decision you’re not proud of, every goal locked in stalemate, every obstacle you did battle with and lost. Some of these intellectual wrestling matches have probably been on going for months, some for years.

Obviously, I have no idea what’s going on in your life. You’re probably living a great life, maybe even an extraordinary life. But this question immediately confronts you with the idea that there’s still more you could be doing. That’s what we’re going to figure out together today. That to me is what the awesome raw potential of going freelance begs you to ask yourself.

What do you love more than money? As a freelancer you have unique volition to control HOW you use your time, HOW MUCH you charge for it, WHERE you’re working from and IF you even want to be working at all. This level of control BEGS you to look in the mirror and ask yourself if you’re using it to the fullest. Go ahead, ask yourself: What is truly important to me? Is it possible I can prioritize my life around THOSE things instead of fitting them into slivers of time left after my day job?

This to me isn’t some lazy attitude about working less. It’s about finding a more personal definition of happiness, a more complete rendition of something everyone claims to want yet few people seem to actually achieve. It’s my belief that freelancers have a better shot than most people at getting there. The bane of the modern work force is that too many people I know are settling for being “content.” Content is a word you will hear me disparage and discard in this article many times. Content means somewhere along the line you’ve settled. Fuck content. You can do better than that.

If you are reading this piece, then at least a part of you must agree. The first step in bucking the trend and finding authentic happiness is discovering what that goal even looks like. Once you have whittled down the form of your happiness, then you at least have a destination. Whatever that looks like to you, how can you use freelancing as a tool to design your life around it? Accomplishing this is when you fully unlock the empowerment that freelancing has the potential to offer.

There are some questions only you have answers to:
What do you love more than money?
HOW do you want to use your time?
HOW MUCH is that time worth to you?
WHERE are you happiest?
And dare I ask…do you want to be working all the time?

These are the questions that freelancers get the privilege of asking themselves if they realize what fortune they have found themselves with. This guide is not about finding out WHAT you want to do for a living. I’m assuming its motion graphics because you’re here, on my site about freelancing as motion graphics designer. Right now, it’s all about how you’re going to spend your life outside your gigs. As a freelancer you now have full and total control over the answer to that question.

How Do We Define a Job?


a piece of work, especially a specific task done as part of the routine of one’s occupation or for an agreed price:
She gave him the job of mowing the lawn.
a post of employment; full-time or part-time position:
She was seeking a job as an editor.
anything a person is expected or obliged to do; duty; responsibility:
It is your job to be on time.

Let’s Redefine What A Job Means As A Freelancer:

The above definition to me is interesting because it doesn’t say anything about working 9-5. It doesn’t mention the fact that you are supposed to be there Monday through Friday and maybe weekends if your boss needs you there. It doesn’t mention the fact that your vacation days should start out at 2 weeks out the year and increase at a glacial rate after years of dutiful service. It doesn’t mention the fact that you should work somewhere at least a year before deciding whether its working for you or not. These are however part of the standard contract that the vast majority of the American work force agrees to when they take a salary job. As a freelancer let me clarify what a job means to you.

A job is a GIG where you know the length of service up front. A gig is where YOU tell your boss how much you’re worth. A gig is a choice of one employer among many that you can choose to accept or deny based on how badly you need the money at the time. That’s it.

Once it’s over you are free to find another one OR you are free to use your time however you fit with no ramifications or penalties or punitive measures, beyond the fact that you will not make money since you’re not working. Unless you sign one, there’s no lengthy contract that makes you an indentured servant for a year at a time, or puts limits on how you want to live your life. Work in this case sets you free to not work as much or little as you want.




Step 1: Conquer Your Fear of Money

The financial realities you base most of your decisions on today might be very different once you find your footing in the world of freelance. IF and this is a big IF….IF you are good at your job, you will find work in this industry as a freelancer. I will say it upfront, if you do not put in the time to hone your craft you SHOULD NOT GO FREELANCE. You’re competing for jobs everyday so you need to be able to stand out to get contracts, BUT if you do, you then you are given the golden ticket to a world of opportunity. Out of all the freelancers I talked to for this article, in one form or another, all of them told me that their financial concerns were alleviated after making the switch. I’m going to let them paint the picture for you.


Sekani Solomon

“Being on staff, when you’re doing the same job as a freelancer and getting paid twice as much, that’s when you should reconsider from a business perspective. [As a freelancer] now the game has changed. It’s more about how do I invest, and manage the money that I have. Money might be something I think about, but now it’s much less of a worry. There’s so much work in the city.
I have a LLC which most of my freelancing goes through, so you can write off a lot of your business expenses, like travel, computers, etc. Even with the new tax laws, if you’re an LLC 20% of your income is tax-free.”

Mike Winkelmann (Beeple)

“Was never really my goal to be honest to be freelance. I honestly like working in an office and being around people. The people I worked with I was good friends with so it wasn’t something that I was really setting out [to do] it just seemed like the projects and opportunities that were coming up through freelance were too good to pass up. And to be honest it was a lot more money, so it was like okay, it kinda doesn’t make sense to keep the full-time job. “

Salima Koroma
“I was making more money than I was when I was working 9-5. That was important to me! The money was important! [When I found out how much more I was making] I was like “Damn!” So the money was important. One of my co-workers who was permalance, was telling me, like “yo I get this amount of money.” He told me how much he was making, then he’d leave for a month. That’s the thing, I felt like I was a better editor than some of my co-workers who were freelancing and making way more money than I was. They’d tell me, “yo, Salima, I come in for a month, then I take a month off and travel and chill.” And I didn’t even realize that life, that kind of life existed.”

Mitch Myers
“Going freelance has granted me much more financial freedom. I am making much more and working much less. It’s a good combo to have in your life.”

Mike Puleo
“After going freelance, I’ve made more money so I don’t really worry about finances. Say I don’t have work for a week, it’s not stressful, I know I do good work, a job will pop up eventually. Now I don’t really live my life around money, if I want to do something I will do it regardless.”

Nate Reininga
“Going freelance made me both more and less conscious of how I spend and earn my money. As time goes on and disaster hasn’t struck (as my friends and family always seem to predict), I’ve become less worried. It will come and it will go. But a week ago I had 4 jobs in 3 days and made enough money for the next month.”


Everyone I interviewed agreed on the obvious: Yes, making more money for working the same hours is amazing. I’m sure you’ve heard by now that freelancers get paid alot more than salary employees for the same job. If you are good at what you do and can get booked most of the time then you will get an instant pay raise of usually around double if you’re coming out of a full-time gig. The simplicity of that arrangement requires a minute of contemplation. You can double the amount of money you make for the same time you were working before, with the added benefits of freedom I bragged about above. Let’s say you do want to work full-time the same amount you did before. Most people are already used to that, so it’s what people tend to aim for when they start out freelancing. Strictly speaking about financial difficulties, you can make a lot of your current problems go away and live with a peace of mind and comfort that you literally couldn’t afford before.

Let’s say you’re bank account is in dire straights. Times are tough and the gig marketplace is bone dry. Freelancing happens to demand either an iron stomach or alot of faith. Which point of view you take probably depends on the type of person you are. Riding the rollercoaster, you’re going to find yourself both at the top of the mountain and at the bottom of the valley. But living on a gradient of employment where there’s periods of not working is a life-altering experience. Everyone I talked to agreed, it actually has one incredible benefit that no one talks about. It produces the profound side effect of actually teaching faith. Not in a supernatural sort of way, but faith in yourself.

If you are good, the jobs will come again. Even when you’re down to scraping the bottom of the barrel of your bank account, if you are good the work will find you. Cutting the umbilical cord of a steady paycheck is step number one to liberating yourself from the way everyone else lives and finding the starting line of your own way of life. Because if you ever want to take off any time to do what you really want (and this article will hopefully convince you you really should) then you’re going to miss paychecks. You’re not getting paid while you’re living your dreams and you need to be okay with that.

BUT GOOD NEWS. THIS WHOLE TIME PEOPLE HAVE BEEN PAYING YOU EXTRA FOR THE TIMES YOU’RE NOT WORKING. Like we talked about above, they’ve been padding your normal salary the whole time simply because they know at some point you might not be working full-time like everyone else. Assuming you can find the work you need to stay busy, you’re going to capitalize this. You’re going to take this extra income, thank them for paying for your vacation and take off on your own. How cool is that? Embrace the situation because it can be your new reality.


ACTION STEP: Get Used to Not Getting Paid Regularly


Step 2: Deciphering Your Dreams

Okay, so you’re good. You can stomach that steady paychecks aren’t essential to making lots of money….now what?

Now you figure out what your dreams look like. Because you’re going to have the ability to choose them over money.

All of us are really two people. One is WHAT we are. The WHAT is the messy reality of being human that the world sees you to be. But another you exists, even if it’s only real to you. WHO you are is the construct in your mind’s eye. What others see is just the tip of the iceberg when it comes to the real you and there might be massively important pillars of your life that, like dark matter, are only visible through the consequences they have on the rest of your life. What does the real you want that might not be a part of your reality right now?

Let’s start with me. I like, you have dreams. One of them is that one day I’d be able to teach people something that’s important to me. If you’re reading this then thanks for making my dreams real. But that’s just the tip of my dreamy iceberg.

I love my personal projects. Though I don’t think of myself as particularly artsy, I’ve got my hands in almost all the mediums of art at this point so I think it’s about time to come out. Yes I’m artsy as hell. One of my biggest dreams is the freedom to pursue these projects that seem important to me, whether anyone is paying for them or not. As far as I’m concerned when I come home and work on this site, work on music, work on learning powerful new motion graphics skills, that is often literally the most exciting thing I could be doing. It’s that exciting because in the realest way I know how, in that time, I am making my dreams come true.

I love motion graphics. I think its an amazing career for 999 reasons but most of the time no matter how much I like what I’m working on, my work is only occasionally dreamy. At it’s best, doing freelance gigs allows me the volition to only work on the projects that have the potential to excite me. But even when those gigs don’t come, and I choose not to be working, I’m not too down about it. If I’m in a good place financially, it’s actually the best part because I get to work on my dreams instead of building someone else’s. That FREEDOM to do my own thing if I want to instead of showing up to work regardless, the freedom to make my dream project, vacation, goal come true whenever I choose to take off is worth any uncertainty in the world.

What activity do you love to do where you can literally feel your dreams coming true? These are the moments we’re going to make you hyper-aware of and make them the centerpiece of the life that you’re trying to design.

This is a massive question to tackle. A massively personal question as well. If it scares you looking that hard at what may or may not be in your life right now, what might help is more examples of what other people doing. Part of the reason i was so excited for this piece was to shine a spotlight on the amazing freelancers I know who are doing exactly what I’m talking about without even realizing it. In their stories you can literally feel the excitement coming off the page. It’s obvious that they’re using their time on the things that truly matter to them. Here’s some stories from freelancers that might help get you jazzed about writing your own narrative.


Stories of Extraordinary Lives

Mike Winkelmann (aka Beeple) (freelance 3D generalist)

“I’m able, because I work from home, even though I work really long hours, I’m able to still see my kids a ton. My wife stays home so the kids are home with me all day. So I’m able to get up and see them at breakfast, see them right when they get up, eat lunch with them, I’m there for dinner, tucking them in and everything. I’m there all day even though I’m putting in a 12 hour day. So that I think is a huge thing that freelance has done. It’s also allowed me to work on personal projects just because I have more flexibility with that even though at the moment I feel like I’m taking on too much freelance and need to rebalance that a bit more towards the personal work. I think with travel too, I recently started going to more conferences and talking and stuff like that, which would definitely not be possible if I had a day job where I only had so much vacation time for stuff like that. So that’s another thing that its really allowed me to do. To travel more. All of those things I think I’ve really helped a lot with.

To be honest even this year, I went to, I was in New York for a week. I was in Amsterdam for a week. I was in Toronto for almost a week. In two weeks we’re going to Boston, then Barcelona, then Tel Aviv. Later in the year we’re going to Paris and Greece for a couple of weeks. So, none of those things would be possible with a full time job, maybe I’d have to pick one of them because I’d have two or three weeks of vacation. There’s just tons and tons of stuff. Last year, I had a talk in Austria, so we took the kids and did three weeks in Austria, Italy and Sweden. So there’s been tons of stuff even in the last three years. The kids are still really young, I’d like to do even more travel than that. I’d like to be gone the entire summer and just kinda travel and work from wherever. There’s been tons and tons of stuff that would just not be possible if I had a full-time job.”

// When Mike was telling me his itinerary for this year I couldn’t help but be impressed. I can’t say I’ve ever heard of anyone with a family going to that many places in one year. Not only was he able to take the vacation time with his family but it sounds like working from home has been him the ability to see them in any moment he’s not actively working.

Tel Aviv, one of the roughly 1,456 places Beeple is taking his family on vacation this year.

Lorcan O’Shanahan (freelance motion designer)

“This year I’ve traveled more just for work than I have in the last 15 years prior. I was hired late last year for a 6 month project that would end with me and a few other artists flying out to the Olympics in South Korea for an entire month. There was other trips to Paris, Austria and London scattered throughout the year for graphics testing days and a crash course in Vizrt for the live 3d graphics work we would be helping build out. Overall it was a financially rewarding gig that taught me more than I would have learned continuing with my normal projects as I had before. I can now stop worrying and start giving some thought as to what kind of work I want to be doing.”

// Lorcan got to travel to South Korea, Paris, Austria and London and get paid to do it. Not only did he get to travel he got to construct amazing live experiences with the craft he loves. What a life.

One of Lorcan’s gigs let him attend and contribute to the Olympics last year in Seoul.

Sekani Solomon (freelance 3D generalist/ designer)

“I took a month off to finish my CGI short. I started the project a year ago, but I needed some time to properly wrap it up. The film is about appreciation, how we interact with each other, and the thoughts we don’t necessarily show. If you peel back these invisible layers, then we can see that’s these are beautiful things.”

// Sekani is amazingly talent at what he does. (Seriously check his site out) He has been working on a short CGI film for the last year. As a freelancer he made the judgement call to take off for a month and dedicate his time to finishing it right. I would vouch for his courage but his film speaks for itself. Also it just won a Vimeo Staff Pick!

A still from Sekani’s award winning short.

Mitch Myers (freelance 3D generalist)

“I think something that would be specific to being a freelancer would be given the opportunity to develop and design the new Adobe After Effects brand identity for the 2018 release. It was incredibly fun to have full control of the direction of the project as well as my calendar to enable me to make time to produce it.”

// All of you reading this probably use After Effects. If you’ve updated to the latest version you’ll see Mitch’s work every time you boot up the program. Every time you boot up think of it as a reminder to take advantage of your situation like he did.

Mitch’s kickass ident that you will see every time you open up After Effects for the next year.

Nate Reininga (freelance shooter, editor)
“Me and my girlfriend happen to both produce videos for a living. We came out here to Cali, as girlfriend and boyfriend, with the intent of shooting music videos for friends. In the process of doing that, we’ve made more connections, and shot more projects than we ever would have imagined. Instead of the cold misery of New York winter, me and my girlfriend decided to just get in a car and take off across the country and have a 3-4 month work-cation.”

// Nate traveled across the country shooting music videos with his girlfriend because he thought it was too cold in New York. And told me he didn’t have anything cool going on in his life. You’re so humble Nate.

If that was a photo of NY everyone would have winter coats on and a frown.

Salima Koroma (freelance shooter, editor, writer)

“As a black woman, as a person of color. I am really into stories about people of color, specifically black people. I’ve found that, those kind of stories when I did them at different outlets, that’s what I cared about and I had to do the stories I didn’t want to do to do the stories about black people that I cared about. And when I did those stories it always went through huge scrutiny and they didn’t understand, they didn’t know that this section of America existed so they always were second-guessing me. The fight made it not worth it to do the things I cared about. I can’t say specifically a story. I meant there were a lot of stories that were shot down by [redacted] or totally changed, or made more safe or comfortable for the audience, which is not what I wanted. It was almost at the point where I felt guilty for doing stories I cared about, but now, I don’t feel guilty for doing stories I care about.

Now I have the ability to say Yes or No. When I was at Time, or NowThis, it was like do this work. A lot of times it was soul-sucking bc you didn’t want to make it, you just had to do. Now people come up to me and they’re like do you want to make this thing, and I can say “nah I don’t want to do that, I’m good.” They’re not my boss. I’m my boss. So, being my boss, it’s okay for me to say no to things I don’t want to do. That’s really big for me as well, having a choice.

Yeah money is important, but if I’m guna be real there are things that are way more important for me. I wanna live life. Like I wanna live my life. I don’t think, let’s say 40-50 hours a week, that’s a long time. That’s a lot of time to be dedicating to making somebody’s else’s dream come true. So the idea of my time being my own, that is very important to me. I don’t mean like “I need my time to myself” I mean that I am the master of my time. If I want to create something, I have the power to do that and if I don’t and I decide I want to stay in bed, I can do that. I am the master of my own world. That is very important to me.

It’s freed me up to do things I never would’ve experienced if I had been bogged down by work all the time. Now I do stupid shit like ride bikes during the week at Central Park or paint, or write, listen to music and not do anything, watch TV, play video games. These are things I was literally never able to do because I was working. So just being able to live life. And doing shit I didn’t have time for before. “

// Writing a TV pilot, series that she is now having her managers pitch to TV networks! Also when she is producing stories, it lets her do stories she cares about that uplift hip-hop and black culture.

Soon Salima will be attending more premieres for her new TV show no doubt.

Mike Puleo (freelance editor, mograph)

“I’m a big fan of live music. I went to see Phish 10 times one month. They had a 3 run in Saratoga Springs, a 2 run in Philly, and 3 days in New York City and 3 days in Denver, Colorado. Def wouldn’t be able to do that full-time. I got to enjoy the summer one year, see friends and family that I don’t get to see as often as I used to. I got to travel to Denver, Pennsylvania, upstate New York, Connecticut, and Long Island. I don’t think most full time people could do that and have their job still waiting for them when they got back.”

// Mike took a whole month off to travel and see Phish 10 days in a row. (Haven’t been personally but they must be really great to see them 10 days in a row)

Mike’s in that crowd somewhere no doubt.

Justin Weiss (freelance 3D generalist, mograph designer, founder of Rapid Motions)

“As a freelancer, I’m finally starting to take my own advice and spread my wings. My girlfriend happened to have moved to Israel recently and I was lucky enough to get a free trip there through the very lenient generosity of the Birthright Israel program. Since I’m freelancing I decided it would be very stupid of me not to take advantage of this free flight to the opposite side of planet Earth and make the most of it. So in June I’m going to take two months off from work to live and travel in Israel, Greece and Egypt. As a freelancer I can take off no problem for as long as I want which opened the door to living a dream I’ve had since graduating college.”

Adventure ahoy.


ACTION STEP: Formalize What Your Dreams Look Like By Answering the Questions Below



Click Here To Fill Out the Questionnaire

1. What’s motivating you to become a freelancer in the first place?


2. What don’t you like about life as a salary employee? How do you want your life to change as a freelancer?


3. What are the top 3 most important things to you in life? (aka what is way more precious to you than money?) In what ways can freelancing give you the opportunity to make them a larger part of your life?


4. What do you want the story of your life to be?


5. Does travel factor into your plans? Using gigs to travel? Remote work? Finding overseas clients?


6. How are you going to find clients?


7. What are you most stressed/ uncertain about when it comes to the idea of freelancing? How can we solve those problems now so you aren’t afraid?


I give thanks and credit to the amazing talents who lent their insight and experience to me to cover this topic properly: Mike Winkelmann, Sekani Solomon, Mitch Myers, Lorcan O’Shanahan, Nate Reininga, Mike Puleo, and Salima Koroma!

Read Part II to find out more about the resources that’ll make it easier to execute your dream lifestyle…

Freelance as Lifestyle Design PT II: The Execution

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