Freelance as Lifestyle Design: Mastering Your New Reality
Beloved Contributors
Perfect You
Everyone has ambitious plans for a version of their life they’d love to lead one day. Daydreams that seem possible for some version of you but never for You.
You want to do all that stuff, but You actually exist and that’s not easy. You’ve got commitments, obligations, and financial responsibilities to real people. But that vision, that mirage of Perfect You is free from it all. They are doing exactly what you wish you were. Screw that guy! But man, their life seems great.
Hold on to that styleframe of Perfect You. One day might not be as far off as you think. All I can discuss for sure is my experience. But going freelance really helped me shorten the gap between what my life was and what I wanted it to be. It seems like I’m not alone either based on the others I spoke with for this piece.
Being self-employed, there is a casual liberty to making lifestyle changes:
Am I going to work next week?
What companies am I working for?
How much am I charging them?
Where am I working from?
Full-time employees can make similar decisions, sure. But once they take a job, they usually can’t update their choices for at least another year. It’s not easy to get another full-time job once you quit. Gigs however, come and go with such promiscuity that gaining and losing employment starts to feel very casual. At the end of your current gig, you will get to decide again the answers to each of these questions. When you do, I encourage you to ask yourself:
What is utterly important to me?
Working 50 weeks a year, 9-5 a day at an office is kind of a default behavior. It’s what everyone does because thats what most jobs expect. While for financial reasons that might be completely necessary for a lot of people, freelancing rates are inflated under the very assumption that you won’t be working 100% of the time. If something is utterly important to you, does it seem appropriate to allocate it the scraps of time leftover from a default work schedule? I offer some exceptions to consider:
Relationships: I love my family and I want to spend more time with them. Maybe I can take jobs where I work from home so I can see them all the time.
Travel: Seeing the pyramids seems life-changing. I’m going to try to do remote After Effects work on my laptop to pay for 2 months exploring the Mediterranean.
Personal Goals: I’ve been working on my album for 3 years now. I think seeing that completed would mean so much more to me than a few weeks worth of a paycheck.
Money: I’m paying off my house by the end of this year. Even if I have to double book myself working on pharmaceutical spots for the next 11 months, I’m going to have a record year financially. (This article isn’t all about working less)
I’m not preaching some lazy attitude about working less. More often than not I’ve worked ridiculous hours because money was really important to me. I’m just questioning if the default preset is the best setting for you. Happiness is something everyone claims to want yet few people seem to actually achieve. It is my belief that as a freelancer you have more opportunity to get there than most people do. Get ready to fully unlock the empowerment that made me fall in love with being self-employed.
The Guide to Finding Your Own Way of Life Through Freelancing
Step 1: Conquer Your Fear of Money
I will say it upfront…If you’re not willing to put in the time to hone your craft, you SHOULD PROBABLY NOT GO FREELANCE.
You could, it just probably wouldn’t be very fun. You're competing for jobs everyday so you need to be at a certain level to win those hiring competitions. I knew lots of people who went self-employed right out of school and their experience was generally less positive than what I’m describing. If you’re not able to charge a decent rate or get consistent work, it becomes less empowering and more demoralizing.
BUT. The more work you put in on your portfolio, the more unbelievable your opportunity becomes.
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. Out of all the freelancers I talked to for this article, in one form or another, all of them told me that their monetary 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 do have. There’s so much work in the city. Money might be something I think about, but now it's much less of a worry.
I also have a LLC which most of my freelancing goes through, so you can write off a lot of your business expenses, such as travel, computers, etc. Even with the new tax laws, if you’re an LLC 20% of your income is tax-free."
Mike Winkelmann (Beeple)
"It was never really my goal to be honest, to be freelance. I 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. Eventually it was like okay, it kinda doesn’t make sense to keep the full-time job."
Salima Koroma
"The money was important! That was important to me! I said “damn” when I found out how much more I was making! One of my co-workers who was permalance, was telling me how “I get ____ amount of money.” He told me how much he was making, then how he’d leave for a month. I felt like I was a better editor than some of my co-workers who were freelancing and they were making way more money than I was. They’d tell me, “I come in for a month, then I take a month off and travel and chill.” 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."
Making more money for the same hours is a huge gift you receive once you make the switch. Let's say you do want to work the exact same amount you did when you were full-time. Most people are already used to that, so it's what they tend to continuing doing when they start freelancing. If you are good at what you do and can get booked consistently then you can look forward to an instant pay raise of close to double what you were making as an employee. I think that might need to marinate a bit so I'm going to repeat it:
You can double the amount of money you make working the same amount of time you did before.
But there’s no guarantees.
Your earning potential is unlimited, but if you don’t work you earn nothing. Your steady paycheck was essentially unconditional. Unless you got fired, it was reliable and it showed up every 2 weeks. It seems obvious but I want to be as upfront as possible and make sure that’s clear. Depending on who you are, this “eat what you kill” lifestyle is either going to excite you or scare you. No one is going to pay you without working and you need to be okay with that, but if you’re driven then theres no cap on what’s possible.
Let’s forecast the worst: Times are tough and the gigs are bone dry. Your bank account is sending you low balance fees daily. In such times, freelancing demands an iron stomach. (Also you should probably take a second look at your money management strategies) How you handle uncertainty probably depends on the type of person you are. Riding this rollercoaster, you're likely at some point to get a view of both the peaks and the valleys. But living on a gradient of employment is a life-altering experience. The interviews I conducted were pretty unanimous in this.
Freelancing actually had one incredible side effect that no one talks about: building faith in yourself. The jobs always come again.
Like we talked about above, in this game, employers allow you to pad your rate by default. They know inconsistency happens to freelancers and they’re prepared to compensate you extra because of it. Working the “default” full time schedule, you can make senior level money and beyond for working the same hours you were working before. If you want the stability of a full-time job and freelance money, permalance roles are fairly commonplace and they feel nearly indistinguishable from having a full-time role. But money isn’t even the best part of the equation as far as I’m concerned.
I’ve mentioned that this is about sculpting a lifestyle around what makes you happy. If your full-time salary took care of your needs before going freelance, then making double means you only need to work half the year to match it. Once your bases are covered financially, you have options. Do you choose to continue working for the thrill of art and profit? Or do you instead choose to reclaim your time do what brings the most joy to your life?
Cutting the umbilical cord of a steady paycheck is step number one. Once you’ve detoxed from that bi-weekly dependency then you’re prepared to start weighing your decision.
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 going to be there any more....now what?
Now you figure out what your best life looks like.
All of us are really two people. The world only gets to meet one of them. That’s whoever the messy realities of being alive have sculpted us into. But another you exists, even if you’re the only one who will ever meet them.
Perfect You.
They’re killing it. Their hopes and dreams make up everything good we believe about ourselves (no matter how delusional) and what’s possible for us one day. What does that person want?
Let's start with Me.
The biggest difference between me and Perfect Me is that he’s way more talented than me. I’ve devoted years of my life to learning how make music, write screenplays and visual design but it really seems to come much easier to that guy. I have trouble finishing anything but he’s already completed the album, drafted the pilot and transcended into the pantheon of great designers. Becoming that guy would be worth anything to me. Freelancing allows me to devote more time to bridging that gap.
When there’s no enticing gigs in sight, instead of scrambling to find something, I often choose to work on Me.
At it's best, doing freelance gigs allows you the power to only work on the projects that are exciting. If there’s no paid gigs that meet that description then you always have the option of doing what excites you. For me that’s usually a creative project of some type, but I’ve prioritized many things over a paycheck in the past. Traveling, relationships, family, even (gasp) just having fun. There’s no more annual 2 week maximum on time off, so its a value proposition you get to weigh at the end of each gig. As long as I'm in a good place financially, it's possible. And like I mentioned above, getting to a good financially has never been easier than as a freelancer.
It’s worth the financial hit to accelerate the projects that I’m dying to bring to life. It’s worth doing a bucket list trip. Has anyone ever regretted seeing the Serenghetti because they missed 2 weeks of a paycheck? I live in New York City and the amount of money everything costs is disgusting. Even a sandwich is $15. If I can live with the guilt of throwing my money away on a daily basis by living there, then not getting paid for a few days or even weeks to do something I find utterly important is a no brainer. Most importantly, I gotta prove that Perfect Me isn’t that special after all. F*ck that guy.
The freedom to make my dream project, vacation, or ambitions come true whenever I choose is worth any uncertainty in the world. It can accelerates goals and dreams that would’ve taken ten times as long had they been organized around the default schedule.
Mini retirements and multi-month vacations are no longer “trips of a lifetime” but can become a regular occurrence for you.
Enough talking about me. 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. Their stories are great examples of re-allocating time towards the things that truly matter. Here's their stories to help inspire your own narrative.
Stories of Extraordinary Lives
Mike Winkelmann aka Beeple (freelance 3D generalist)
"Even though I work really long hours, because I work from home, I’m able to still see my kids a ton. My wife stays home and 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 its really helped a lot with.
To be honest even this year, 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. Last year, I had a talk in Austria, so we took the kids and did three weeks in Austria, Italy and Sweden. 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 even in the last three years. The kids are still really young, but 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."
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 were 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."
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."
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."
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."
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 because 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 going to be real there are things that are way more important for me. 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."
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."
Justin Weiss (freelance 3D generalist, founder of this site)
"As a freelancer, I'm finally starting to take my own advice and spread my wings. My (now ex) 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 stupid of me not to take advantage of a free flight to the opposite side of the Earth. In June I'm going to take two months off from work to live and travel in Israel, Greece and Egypt. The ability to take that time off opened the door to long term travel, a dream I've had since graduating college."
Action Step: Formalize What Your Dreams Look Like By Answering the Questions Below
Self-Discovery Questionnaire
What's motivating you to become a freelancer in the first place?
How do you want your life to change as a freelancer?
What are the 3 you spend your time that are most important to you?
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!