Freelancing Full Time Will Break You (not how you think)
Freelancing Full Time Will Break You (not how you think)
Can you handle the brain damage?
Who should do this
There’s a wide spread of people in the BowTied Jungle. Everyone from very wealthy, already made it people to young people wrapping up high school and trying to figure out what to do for their career. And many somewhere between.
This post is geared more for people just starting out or people stuck in some W2 job that isn’t working out for them.
If you’re already in a well paying career that’s a good fit for your talents, skip this and build your Wifi money. If you’re already rich, this one probably isn’t for you.
One exception: If you have aspirations to build a service based business, it could make sense for you to start out as a freelancer, then hire and scale as you bring in more business and grow. For example if you have strong coding chops, but hate working for The Man, you can start by taking freelance coding gigs, hire help as needed and eventually work up to opening your own dev shop.
Why I’m mentioning this
I’ve been a freelancer most of my adult life so this is everything here is coming from experience. There is certainly a right way and a wrong way to do this.
I’ve done both. Things are awesome now. Have a few solid clients and making great money.
In the past I’ve been so broke I couldn’t pay the electric bill, living in “the cockroach apartment” as I’ve explained on Twitter.
Hopefully I can save you some time and make sure you start this off on the right foot.
Eat what you kill
Working for myself always was appealing. No part of me ever wanted to take orders from people I don’t respect, even if I’m being paid to do so.
I’ve worked various jobs over the years whenever I had to, both white collar and blue. Moving companies, construction, admin, and even sales. If you have to do this too, fine, but keep your eyes on the prize and don’t get stuck there.
I was able to force myself through it, but I felt dead inside because I knew this wasn’t a good fit for my personality. If I was making more money or had more freedom, I could have sucked it up but that just wasn’t the situation. I was also pretty clueless back then about how you get into a high-paying career like tech or finance.
I legitimately thought those were only careers for genius-level smart people, children of rich folks, and Ivy-League grads.
Being self-employed offers a significantly higher amount of flexibility but you can’t phone in any work. Takes a certain kind of person. You can’t just hang out and have a slow day then still collect a check. You are paid to produce. If you don’t produce, you don’t get paid. Got sick and can’t work this week? Hope you saved some money to smooth that drop in income over. Your spouse wants to sleep in, order takeout and watch Netflix for 4 hours this Saturday? No rest for the wicked.
In addition to eating what you kill, you also WILL need to learn to hunt new beasts from time to time. Industries change. New technology makes old ones obsolete. In the video world, what used to take a semi truck full of broadcast hardware can now be accomplished with a laptop and a 16 space hardware rack. It’s your responsibility to keep your skills current and pick up new ones as you spot demand.
Structuring Your Time
Especially if you’re doing work that is asynchronous, you can adopt whatever bizarro schedule you like. There is no boss telling you when to show up, what to wear, how long you have to eat lunch, or what your work environment should look like.
This doesn’t mean you blob out and do whatever you want.
All that matters is the demands of your clients. If you’re on the west coast and the only time your east coast client can meet is 8:30AM their time, set your alarm now.
If you’re the type to fuck off and get distracted by YouTube videos when the boss isn’t supervising you, this life might not be for you. It’s 100% on you to structure your time and figure out the most efficient ways for you to deliver things.
You also need to track your time on projects to figure out what work is most profitable and what isn’t worth your time.
Personally, I can say there are some projects in the Jungle I won’t take anymore and other things I’m actively investing in because the margins are stronger. As far as schedule, my best hours are beginning about 1 hour from waking up until I need to eat, then late afternoon to late. Sometimes very late.
Don’t listen to all the influencer crap about waking up at X time being most productive. That’s for wannabe people. There’s no magical golden hour of productivity for everybody.
What really matters beyond client demands are simply what’s most efficient and you need to figure this out yourself. I’ve always been more of a night guy and I like to do certain things off peak hours to avoid hoards of 9-5 people so I structure things around that.
Taxes
Working for yourself will force you to think about taxes from a business owner’s point of view right away and you get to enjoy some of those advantages immediately.
You can’t deduct miles driven for work, a home office, supplies, new computer purchases, or anything else at your W2. If you’re doing the exact same work for your own operation, you can.
The other thing is the act of paying taxes hurts a lot more so you care about tax advantages a lot more. Why? At your job someone else takes you tax payments out of your earnings, then you get a check for the rest. Feels like the tax never even happened. Your tax refund feels like a fun bonus because you never actually had the money in your hand. People talk about it very openly in this way.
Working for yourself, you get gross payments and have to have the discipline to take out money for taxes every quarter. Lots of people say they are intimidated by having to manage taxes, but in reality it’s not hard once you get the hang of Quickbooks and find a decent accountant.
That actual awful part is having to cut a check every quarter of your hard earned money, then go out and drive over 6 year old potholes the size of a Koi pond and watch public officials blatantly lie to the people paying their salaries. Everybody pays, but it hurts more when you’re holding the money upfront instead of it never hitting your account to begin with.
Brain Damage
When I talk about being brain damaged from working for yourself, I’m referring to the shift in how you view working life.
If things get really slow or you fall on your face and have to go back to working a W2 for a little while (like I did at one point) you will feel like a complete moron the entire time. Having to do some busy work to make your boss happy makes you feel like you’re back in the 5th grade raising your hand to ask for permission to use the bathroom.
The inefficiencies, obvious mistakes, and pointless interactions will grind your gears. I found myself chewing the inside of my cheeks every time a co-worker wanted to invade my lunch and make small talk because I ordered Korean food and he wanted to tell me all about how he knows what bibimbap is. Cool story, Ryan.
Freelancing for even a few months rearranges your head. Once you see it’s possible, the magic glasses are stuck to your face forever. Congratulations, your brain is now broken.
I went back to the office years ago initially optimistic.
“hey maybe this will make me more balanced”
Had it in my head that I could just work a day job, pursue my hobbies in my free time, then live a normie life like regular people. Pure fantasy. Had to learn the hard way I’m not built for normie life.
Lasted a few months. After work I started putting up flyers and dropping business cards every place that would let me to find some tutoring clients. Not my favorite thing to do, but pays well enough that I could match my paycheck in half the time while I got other things up and running. I’d spend time at my desk pricing out life in terms of clients.
Rent costs X number of clients, food costs Y clients, etc.
I probably should have built up more of a client base before I quit, but brain damage was already done. I figured if I had 80% of life paid for by working on this in off hours, but could probably get to 150% fairly quickly if I focused on that all day.
Took the leap and it basically worked. Wasn’t always pretty, but I got out and stayed out. Wasn’t until early COVID times that I really got my priorities straight though.
Same deal now that I’ve leveled up from work I don’t do anymore. Once you see what your capable of, going backwards is excruciating. If I have to go back to writing cheap sync music to eat, will probably play out like a lump of sodium in water.
Don’t repeat my mistakes
Speaking of screwing up, if you do this right it shouldn’t happen to you. My main mistake was drinking the “follow your passion” Kool-Aid for too long.
I’ve mentioned I have a music background and I spent far too long trying to make creative work and fund it with lower hanging fruit like writing TV and web sync music. Or doing things like playing in wedding bands and dive bars. Or thinking that prestige leads to income.
I was watching margins compress well before COVID, then you know what happened next with the money supply. Rates stay the same while everything else gets more expensive. Meanwhile guys I used to be jealous of because they release music on cool person record labels and win industry awards are still living with roommates in some cases.
You want to jump into your freelance work and be paid well right away. Don’t “follow your dream”. Follow the money. Don’t sell your passions. Identify your transferrable skills & talents (BowTiedBull outlines what these are) and apply those to something with a clear demand.
You don’t necessarily need to jump into something you’re going to do forever. Get started somewhere, then pivot later if necessary. Think about what you can get up and running today. That’s where you start.
Doesn’t have to be glamorous. Don’t over think this. Even if you know the service will be obsolete in 5 years, demand today is still demand you can tap into.
In 2023 with Wordpress and Squarespace and Wix and all the rest, people are still paying me good rates to do fairly basic web design work. Even with AI image generation, there is still money to be made doing graphic design work. You can then roll that experience into something more specialized with better margins later as you learn.
Maybe you start doing some web design or fixing Wordpress sites for not thrilling amounts of money just to get some portfolio pieces up, but then work your way into web3 and smart contract work.
For example, I did commercial composing for a while in tandem with video production work (mostly live events and streaming gigs).
Now that I see margins are way better doing motion graphics and 3D work and my newbie coding skills dovetail nicely into that, that’s where I’m focused. My music work also gives me an edge with the audio portion of this so it’s a no brainer for me.
Similarly, I learned to film events with a guy who’s more suited to working in the field for personality reasons. He hates editing and being at a computer all day. He now works very regularly as a Steadicam operator and has a pretty ridiculous collection of lenses, hardware, and cameras. Same equation at the heart of it. More specialized skills and gear + demand = higher day rates.
Side Note: Weirdly once I stopped trying in music and just did whatever I wanted, some wild commission opportunities came in. Invoices in the $5-10K range. I would have eaten my hat in broad daylight for something like that years ago. The math of life is just like that for some reason.
Questions?
I’m happy to advise if someone has specific questions on this. Will go into as much detail as I can, but I don’t have experience will everything and a million things can qualify as “freelancing”.
Everything from teaching piano lessons to coding to painting houses to baking fancy cakes.
FYI:
We can define freelance work as working for yourself in something not saleable.
For example, if you build an affiliate site on your own that makes money, you are not freelancing. You are a soloprenuer because you can sell that website, whereas if you are a graphic designer doing client work, you can’t sell your self-employed design career. The skills have value that you could apply to a business, but they don’t have equity you can sell in a marketplace.
“Solopreneur” operations are different and something where I’m very much actively learning so I can’t speak as authoritatively there just yet.
