10 Realities of Freelance Life

As I’ve previously discussed, I recently made the transition to freelance work and I’m loving it. Many people have a romanticized view of freelance life, though, and there are a few hard realities I’ve encountered in my first few weeks that I thought I’d share with anyone considering taking the plunge.

10) You will spend a lot of time just trying to get paid.

Remember when your regular paycheck was deposited on a predictable schedule directly into your bank account? It seems like a hazy dream now, doesn’t it? Just because you’ve lined up enough projects to pay the bills doesn’t mean that your clients are going to pay their bills precisely when you need the money. You will spend a lot — I mean, A LOT  — of your time writing and sending invoices, following up on old ones, recording expected pay dates, and anxiously watching your bank balance whittle down even as you accumulate more and more earnings on paper.

9) You will spend at least one third of your time on personal accounting.

At least, that’s my estimate, based on my own experiences. Part of that includes the invoicing mambo described above, but there’s plenty more to do once that’s taken care of — tracking your business expenses, filing your receipts, filing estimated quarterly taxes, and more. Since you don’t have a friendly HR department helping you with your benefits anymore, you’ll also spend a lot of time scrutinizing health plans, retirement plans, and all the other places your money goes to live (if you haven’t spent it all on booze, women, and rock’n’roll).

8) …And what’s left over after that will have to be split between doing your work and finding more work.

You need to always be thinking about the next job…and the job after that, and the one after that. I already have work lined up through the end of the year, but I’m tracking down even more long-term projects to get me through next spring. The best advice I could give someone who’s thinking of becoming a freelancer is: it’s not enough just to land a long-term contract that pays the bills. It has to be a high-paying enough project (per hour) that you can pay your bills by only working one third of your available time, because the other two thirds will be spent doing your accounting and tracking down new work. That’s a pretty high bar.

7) You should probably still get up in the morning. And put pants on.

You’ve probably already figured this out if you’ve read the first three items on this list — you can’t sleep half the day with so many things to do. But this is an important discipline, too, something that my mom (who’s been freelancing for decades) told me: you’ll focus better and get more done if you create a work day for yourself (up by a certain hour) and dress for it too, even if it’s just throwing on a pair of real pants instead of your PJs. Then, you’ll also be more ready for all that networking you’ll have to do to scrape up extra work. And, you’ll just feel less gross all the time. Sadly, for most of us, the pantless workday exists with the free lunch in the workplace of fantasy.

6) Sometimes you’ll get lonely.

The noise and bustle of office life can seem infuriating when you’re in the middle of it, but it suddenly seems comforting when it’s gone. A day can get very long when you work at home by yourself. Even though I’m fairly introverted, I find myself filling up my social calendar far more than I ever have, partly because my social energy isn’t being drained every day by a multitude of office interactions. I learned quickly how important it is to set up lunches and coffee with friends, and to attend happy hours and networking events — not just to drum up new work, but also to keep myself from going stir-crazy.

5) People will ask you what you do “for real.”

When people ask me what I do, I say I’m a writer. That is what I do. I write for clients — blog posts, marketing plans, business models, publicity pitches — and I write for myself — short stories, essays, novels, vignettes. And I do manage to scrape up a little money from all these activities, though of course some bring in more than others. (What a wonderful excuse to remind you to pre-order my new book!) However, I’m often asked what I do “for real.” People seem to be incredulous that I make any money at all from these activities. And there’s a note of truth in that — it took hard work and long hours to get to the point where I could. Regardless, there will always be some people who ask what your “real” job is, or assume that you lack a “real” job involuntarily. I try to answer politely and thank them for their concern, biting back the response, “Everything I do is real.”

4) It becomes a lot easier to lose track of time or forget what day it is…

Maybe this is more a reflection on my own absentmindedness than a general rule. Without a constant influx of meeting reminders and company memos, I find I often forget what the date is, or even lose track of the day of the week. Though sometimes I wonder if that’s partly because whenever I worked in an office, I’d always be counting down the days until the end of the week. That said…

3) …But you’ll still look forward to the weekend…

You’re working from home now, but chances are most of your friends aren’t. And a lot of the social life of cities and towns is built around the evenings and weekends, too — street markets open, bands flood the bars, festivals and parades and block parties happen. That means that the weekend is still your biggest chance to spend some quality time with your favorite people, get out, and do something fun.

2) … Because sometimes the hard part isn’t finding the discipline to keep working, but having the discipline to stop.

This is another valuable lesson I learned from my mom. If you’ve managed to carve out a life for yourself freelancing, you’re probably already an incredibly disciplined person. The problem is, that means you’re probably also the sort of person who easily falls into the trap of overworking — once you find the discipline to get going, it’s hard to find the discipline to stop. Work is rarely done; and when you work on a project basis, that usually means that even if you’ve just completed one job for a client, there may be two or three others still outstanding. Without the clear boundaries between work time and personal time set up by 9-to-5 life, it becomes easy to keep going and going until you burn out. This is especially easy to do when you’re working on something you love. I could happily write and write night and day…until I burn out. And on the other side of burn out, I’d find that I’d lost sight of many of the other activities and relationships that give my life joy.

1) You might be poorer, but you will be happier.

Let’s be honest, no one becomes a freelancer because they want to be broke all the time. But the reality of waiting for checks to come through and trying to scrape together just enough projects is enough to make any newly-minted freelancer think long and hard about just how stifling that 9-to-5 was. And that’s okay; it’s not for everyone, just as office life isn’t for everyone. But for those who do finally settle into the freelance life, the money you’re missing seems less and less important than the independence you’ve gained. And the two o’clock beer on your patio on a Friday afternoon with all your work set down for the week.