While most people start their day by commuting to an office or job site, I begin mine by moving from my bed to the couch in my living room.
With my laptop propped up on a well-worn pillow, I start writing, sending emails, and beginning the other tasks of my work day at about 7:30 a.m. There's no traffic to navigate, aside from my wife getting ready for work and my two cats jockeying for the best spots to nap in. I also don't need to dress up or even take a shower before my day can begin.
It's a hard-won lifestyle that's very different than the the typical 9-to-5 job, but being a freelancer instead of having a traditional job is not for everyone. There are amazing perks to the freelance lifestyle, but you have to be wired a certain way to make it work.
You need to find work
The vast majority of my day goes into writing and completing other tasks as a contractor for The Motley Fool. That means, that unlike at past times in my career when I freelanced for websites, magazines, and anyone else who would pay me, I don't need to look for work anymore.
Most freelancers, no matter their profession, either need to a find a work-from-wherever contracting situation that keeps them busy, or they have to build a network of clients. Both take time and quite a bit of hustle to make happen.
You need discipline
When you have an actual job, having an off day where you get very little done does not impact your salary or hourly rate. As a freelancer, you only get paid for the work you actually do. That means that while I could simply stop working whenever I want and head to the beach, if I do that I don't get paid.
The joy of that is that I can push off work for any number of reasons. But if I want to keep my income steady, I have to find time to make up what I missed. That means that I pay for my beach time or my recent trip to Universal Studios with late-night hours and weekend work -- times when most 9-to-5ers are relaxing (or sleeping).
Everyone assumes you are available
Perhaps the biggest drawback to a freelance, work-from-home (or in my case from a lot of coffee shops) lifestyle is that many people in your world -- even ones who know better -- assume you are always available. That makes me the designated person to pick people up at the airport, and I've gone to a lot more school events than I ever did when I had a traditional office job.
Sometimes that's a perk. I can meet someone for lunch, or join a pal to see a movie in the afternoon on opening day before it gets crowded. At other times it's uncomfortable; you have to be forceful with people you care about that being able to work whenever you want is not the same as not having to work.
It can be quite lonely
While working form home or various public places sounds quite nice (and it often is), my day often goes by without me having an opportunity to talk with anyone. On the day after the Super Bowl or the morning after a major event, I may be full of things to say during a coffee break, but there's nobody to share them with.
You need a plan
While I'm a freelancer, I treat my work life as a very flexible job. That means I have a plan for how much work I want to do each day, week, month, and even year. I'll let myself borrow from one day as long as I make it up that week, but I tend to balk at allowing myself a less-productive week that I'll make up by working harder the rest of the month.
There are weeks I exceed my plan and weeks I just hit it, but I find it important to never come in below my personal goals. That's not always easy -- and it sometimes means that on Sunday, when everyone else is seemingly off having fun, I'm sitting as I am now, with my laptop in front of me.
It's not for everyone
A less traditional work situation has allowed me to do many things. It gave me the time to take up yoga, have a swim most days, and be a more involved parent. It also lets me cook dinner most nights, and gives me tremendous freedom of location.
However, freelancing also means that I have to supply my own health insurance, and that taking a vacation or a sick day means I don't make any money during the period I don't work. And while it's not the case for me now, many freelancers must also deal with having to collect money from companies happy to hire them, but not as eager to pay the bill.
Being a freelancer who does not go to a job everyday has made my life much richer, but it's not a lifestyle that works for everyone. For some people stability, community, and separation between work and off-hours are more important. That's easy to understand, and while I can't picture myself ever taking a traditional job again, no situation is perfect for every person.