Setting realistic freelance goals and sticking to them

July 2, 2008 1:06 PM

Freelancers and other creative self-employed types: How do you set realistic, meaningful work goals and stick to them when the main person you're answerable to is yourself?

When you're your own boss, how do you set work goals that are both challenging and attainable - and more important, how do you take them seriously? (What happens when you don't meet them?)

As a freelance writer I struggle with this. Motivation isn't really the problem. (I often struggle to make myself stop working.) It's more about how to keep yourself answerable to yourself without driving yourself nuts.

I try setting goals, but either a) I meet them and then think, hmm, that goal must not have been challenging enough, or b) I don't meet them, and feel bad about it for a while but then that goes away. So then I just give up (if the boss is never satisfied, why bother?) and work hard all the time, which is its own problem, never not thinking about work.

I love what I do, and I want to keep doing it better and better, setting my sights ever higher, but I'm also tired of not knowing how high is high enough, what's reasonable to expect. I know this is a bit of a psychological issue - never being satisfied with yourself, being your own toughest critic, etc - but I'm sure there is some good advice out there.

I'm especially interested in hearing from creative types whose workflow is often dictated by people and/or events outside of your control (i.e. no matter how much you bust your ass, sometimes they're just not buying, assigning, etc.)

posted by El Curioso to work & money (11 comments total)

Discipline. Plain and simple El Curioso. Boring routines and discipline.

In my "spare" time I like to always have one book pending - it brings me no measurable income and distracts from my consulting work - but it's an exercise in self-education and just good practice. I figure after I write about 10 of these I might know what I'm doing. It also helps to productively fill the slow periods when there isn't much other work.

So I write 1 page a day, or more if I'm inspired, but at least one full page. Sometimes (who am I kidding most times) it's crap when I read it the next day and I decide to re-write it, but I plow on. I set loose deadlines for having chapters complete and then I try to stitch together a book.

It becomes a little obsession. Missing my own deadlines is like missing a run, or a drink before bedtime. I can do it when I need to, but I'd rather not. It's part of my routine.

I know this is a bit of a psychological issue - never being satisfied with yourself, being your own toughest critic, etc - but I'm sure there is some good advice out there.

Anyone who says this is fooling themselves. Your customers (or readers) are by far your toughest critics. I have never made myself feel as bad - not even close - as when I receive someone else's bad review. It's like punching yourself in the head compared to being punched.
posted by three blind mice at 1:39 PM on July 2

I never did freelance work full-time, but when I did freelancing part-time, the best thing I could do for myself was to get some hobbies.

Sounds trite, but it's No Joke.

Having something else that you're interested in, that pulls your mind away from work, that you just can't escape thinking about at least some of the time, is surprisingly good for you. It gives you something besides work to think and talk about, and lets your mind rest. Marathon sessions of concentration on a single task/set of tasks can be great in moderation, but fatigue creeps in slowly and subtly. (Besides, then you're not as boring to family/friends/SOs :) )

My own most productive and satisfying moments of freelancing are when I had torn myself away from some other activity. It's about constraining your time. It's the same reason so many poets work within well-established formats: there is freedom in the boundaries. You constrain your time when you get hobbies and so you don't float into the nebulous "well, this project could be better if I just spent a few more hours on it..." Instead you're antsy to get back to collecting stamps or taking pictures of yourself with iguanas.

And I think this advice goes double if you particularly enjoy what you're doing in the freelancing arena.

Get a Flickr account and let's see some iguana photos!
posted by burnfirewalls at 1:44 PM on July 2

Right now I'm keeping myself to big lists of things to do. Breaking things down into small simple goals that can be crossed off-- for me the challenge is the amount of work done, not the difficulty level. I'm an illustrator/graphic artist though, so each project has its own inherent challenges and I work my hardest on each thing. My problem is more of motivation, I come up with ideas but often never finished them in the past. The act of seeing a big page fill up with scratched off achievements reminds me that I'm working as hard as I can.

Basically I keep myself answerable to myself by instituting deadlines and wanting to meet goals. Breaking things down to simpler goals leads me to get to where I need to go without worrying if I'm good enough to take on a huge project. If I pay attention more to the short term projects and finishing them, then I look back with pride about what I've done so far. The more you work, the better you typically get, the more sure of yourself you get. The more work I do, the more I learn about what I want to improve and where my weaknesses lie so I can work to improve them. Of course I also feel that burn of 'You're not working hard enough! Push yourself!' but I know that working consistently and persistently is the way to go for me. Putting in dedicated hours every day to work helps me accomplish what I need to do. Of course I have my own rhythm, I take breaks, but I try and stay creative all the time.

If you meet a goal, try and think positively! Sure, it's work, but it's awesome to complete a task. You could've just given up, but you didn't. And that's great! Then think, what next do you want to do? If you fail, it's not really a failure-- you can always approach it again.

It's hard when people just aren't buying-- but when that happens I just work on personal projects and bust my hump trying to get more marketing done. The thing that's rough about freelancing is that you're the boss, and with being the boss you can't just be creative, you have to learn the business and work hard to get all aspects of your business running smoothly and to full-capacity. It's another job in itself!

My point I guess is that you should feel proud of yourself for trying this-- freelancing/self-employment isn't easy. When jobs aren't there, it's way too easy to fall into the trap of 'Where have I gone wrong? I must be doing something wrong,' and then beat yourself up about it. (I know, because I've done it like a hundred times this year already) Sometimes when you try to set your sights high, you lose sight of what you're doing, and it's too hard to see improvements when you're always thinking you're not good enough. If you work hard and celebrate the successes and don't let the failures get to you too much, and step back every now and again to assess where you've been and where you're going, I think you'll feel less critical of yourself.

Good luck! It's tough, but ultimately I think it's so rewarding!
posted by actionpact at 1:48 PM on July 2

the best thing I could do for myself was to get some hobbies.

Excellent observation. There's this thing called Metafilter that has proven to be a great distraction.....

Seriously though. Working alone can give you a bit of cabin fever. Metafilter is like a walk to the coffee machine and some small chat, but it makes a lot of difference in your ability to concentrate.
posted by three blind mice at 1:54 PM on July 2

burnfirewalls is absolutely right. You need other things to do. Give yourself permission to take breaks. One of the reasons you go into freelance or self-directed work is when you're the type of person (like me) who hates imposed structure (or just can't sit still). This basic personality trait of course interferes with the need to impose the effing structure on *yourself*. So what I've learned to do is give myself permission to mess with other stuff. I am incredibly well organized, which is a plus, but also hate doing the same or similar tasks for extended periods. So I've basically made my workday 12 hours, but within that I do income-generating work about 5-6 hours, gardening, cooking, chores, MetaFilter, my (secret) blog and sometimes general goofing off. I think the key is that even though I resent so-called authorities telling me what-when-how, I am so well organized that I tend to get stuff done ahead of time anyway.

Lots of stuff in the green about how to get organized.
posted by nax at 1:58 PM on July 2

I wonder if you would benefit from a big, hairy goal that all those other goals clearly lead toward. Then when you complete a goal, you see it as a step toward something bigger, and you've got momentum for the next goal.

My big goal is being able to do creative, challenging work anywhere that there's an internet connection and make enough money that I can send a proportion of it to small businesses in the developing world. Every goal is a step toward that big, hairy goal. So when I meet a goal, I think, "All RIGHT! One step closer! On to the next!" I'm less than a year away now and really chomping at the bit.

I'm also into quantifiable goals.

I set an income goal for the year. From that, I set an income goal for each day. Each day, I need to either meet that income goal with billable hours or spend X hours on business-building work that will pay off in the future. This business-building work includes developing info products, marketing myself, etc.

I also set deadlines for my own projects (info products), but these can be frustrating, because client work often interferes.

I use LifeBalance software to set and track the goals that lead to the big, hairy one. And I use Freshbooks to track all my time, not just billable hours. That keeps me from wasting too much time online.

And to show just how obsessive I can be, I also use Time Out software to keep me on track. I set 15-second mini-breaks to occur every 10 minutes. When the mini-break icon appears, I not only rest my eyes briefly, I (often) think, "Is what I'm doing what I should be doing? How is it bringing me closer to my goal?"

Every 50 minutes I take a 10-minute break and do something completely different, like crazy dancing to loud Bollywood tunes. And I'm with nax on the longish days full of big, big breaks. Today, I took 2 hours in the middle of the day to ride my bike to the co-op, pick up my CSA food, and read a book while sipping chai.
posted by PatoPata at 2:26 PM on July 2 [1 favorite]

I decided not to work on weekends unless I wasn't going to meet a deadline. Otherwise, work time is about 9 - 5 weekdays. If I get over a certain number of billable hours, I feel free to take Friday off. When I work, I track my time so that my contractees (?) get value for money. That is, if I'm logged on for a job, I don't go look at metafilter or whatever, I keep working until I log off (my spreadsheet for billing). It surprises me how often I fall below 7 hours a day with this, but, the good news is, my contractees are happy, I'm happy and not overwhelmed, and I have enough money to live on. If I were to work superhard (say twice the billable hours I'm doing now), I would have to find myself another contractee, and I would never be able to take a break.

What I should be doing more of is self promotion, but as I'm currently studying at the moment and don't want my business to take over my life, I've quite happily put that on the backburner.

My system will not work for everyone.
posted by b33j at 2:56 PM on July 2

I try setting goals, but either a) I meet them and then think, hmm, that goal must not have been challenging enough ...

I don't think all my goals or tasks in a given day need to be super-challenging. Indeed, I find I'm most productive when I alternate something challenging with two or three easy things which nevertheless need to get done - like this:

* code new search page (challenging)
* change wording on About Us page (easy)
* check backup file; make sure backup worked (easy)
* code new login feature (challenging)

Lots of my work is easy (for me). It still needs to get done. And it can be really rewarding to cross three tasks off my to-do list with just five minutes of effort.
posted by kristi at 4:17 PM on July 2

When I have a goal I'm excited about meeting, I try and tell as many other people as I can. I hate telling other people when I've failed to follow through on something, so the more I increase the chance of someone else asking me "so how did x go," or "have you found a publisher for y?", the more likely I am to follow through.

In other words, if you're only accountable to yourself, share the love. (And the guilt!)
posted by j-dawg at 5:02 PM on July 2

I try setting goals, but either a) I meet them and then think, hmm, that goal must not have been challenging enough, or b) I don't meet them, and feel bad about it for a while but then that goes away.


In terms of fuzzy concepts like "challenge" and "success": I don't know how mathematically inclined you are naturally, but what's worked for me is to quantify everything I easily can.

Finished applications/projects get listed in categories:
• Deadline Met; As Planned
• Deadline Met; Slightly Compromised [in these cases I'll note the specific nature of the compromise(s), there in the entry -- for you it might be things like "unsatisfying end in last paragraph" or "should've gotten quotations from two more sources"]
• Deadline Met; Seriously Compromised
• Slightly Late; As Planned [in this case, noting how late]
[etc. ... all the way down to Seriously Late; Seriously Compromised]
It's also really useful to have a category called Abandoned Solely For Deadline Reasons, to track how many things you were really interested in but couldn't finish.

And after I find out this info, each application gets noted as successful or not (in my case, it won the grant/prize/etc. or it didn't).

I do all this by calendar year (fresh start every New Year's Day) and I've now got six years of these records to look back on and evaluate. (In my case, I'm a composer making most of my living from grants, prizes, commissions, fees, etc., many of which involve annual deadlines for the same thing).

The key is to be both entirely honest with oneself about every deadline-meeting circumstance and dispassionate about the eventual results. This way I get an acurate record, don't invest in it emotionally, and get to see all my goal-setting and deadline-meeting success expressed, at least roughly, in percentages.

Some obvious meta-goals include increasing the percentage of "Deadline Met; As Planned" entries and keeping my overall yes percentage low, because a high yes rate indicates one isn't "reaching" enough -- in your case a high yes rate might indicate you could try doing more submissions to very competitive/selective publications you wouldn't necessarily think you have a chance of getting a yes from. (This method has helped me reach for and win a number of things I wouldn't have guessed I'd have a chance at until a few years later.)
posted by kalapierson at 11:15 AM on July 4

It surprises me how often I fall below 7 hours a day

I've been employed by a software development company that billed all customers by the hour. It was surprisingly difficult to be able to bill more than 70% of working time without doing overtime or being very single-minded without doing any kind of management meetings.

That realisation is the most important thing I learned at that company. I've been self employed since then, and I'm able to be quite content not hitting 7 billable hours per day.

So, please don't think goals aren't challenging enough if you meet them. If you set yourself up to needing to bill 7 hours a day, you're setting yourself up for failure and getting burned out. Set goals such that you meet them with at least 20% less time than estimated.
posted by flif at 12:34 PM on July 4