If you want some support in taking action but being nagged makes you contemplate violence against the nagger, accountability software may be the perfect solution for you.

Different systems have different approaches, but the basic idea with accountability software is that you set up the system to help you establish habits or do projects, and the software:
- sends you reminders,
- asks you whether or not you’ve done your scheduled tasks,
- keeps
track of your progress, - gives you nudges if you’re slacking, and/or
- gives you little rewards for staying on
track.
Many systems also have a social component. If you’ve read my What is accountability? discussion, you know that I’m not a big fan of accountability. I turn to it only in very limited circumstances. When I do, accountability software is my method of choice. I find being nagged by people offensive, but I’m fine with being nagged by software.
Gentle, good for projects you enjoy
Accountability software is a sweet tool you can use to give you a gentle nudge and help you remember to do things that you like that get lost in the craziness of everyday life. You probably can’t use it to force yourself to do something you hate — it’s just not intense enough for that. And you know that if you decide to bail, you can just turn the software off.
Trouble finding good free accountability software

Hoping to find some gems I could recommend to you, I tried a lot of free accountability software systems, with very disappointing results. Most had serious problems. They were severely crippled unless you upgraded to a paid account, or they had intrusive advertising pushing you to upgrade. Some collected a scary and unnecessary amount of personal data and had privacy policies with giant, gaping holes in them.
Two sites I like
Everything isn’t bleak, however. (Well, see update below.) There’s a site I use regularly that I’m excited to recommend to you, though it’s only for a specialized purpose.
750words.com will seduce you into developing a daily writing habit, even if it never occurred to you that you wanted one. Or maybe that’s just what happened to me.
Update: Things are looking bleaker. 750words.com moved to a fee model in 2013. The fee seems high to me — $5/month to write one entry a day (it’s cheaper if you buy several months at once), though you get the cool badges, stats, and other motivational tools to keep you writing every day. If money’s not a concern for you, though, you may want to check out the site.
A site I used daily that I adored, rootein.com, permanently shut down in August, 2012. We’ll see if someone else picks up the site and runs it. Meanwhile, I’ve found another site/app combo that has a similar feature set, HappyRitual.com, but I have mixed feelings about it.
750words.com
750words.com helps you establish a practice of writing 3 pages — or 750 words — daily. The idea is that you write these pages quickly, without stopping to think or caring about organization, grammar, spelling, or making any sense.
Many people (including me) consider this practice to be richly beneficial. It can help you unleash your creativity, get clarity about your life, and improve your writing.
Julia Cameron’s wonderful book, The Artist’s Way, is the place to learn about this practice, which she describes as writing morning pages. I also like Mark Levy’s book on freewriting, Accidental Genius.
The site is brilliantly designed to seduce you into writing every day. It has many tricks up its virtual sleeve to keep you in the writing groove, but the most powerful one for me is the badge system, which rewards you for continuing to write every day (and other things).
You may know intellectually that it’ll make no actual difference to your life if you get that Pegasus badge or not. But it feels like a big deal. Once you have a longish streak going, you really don’t want to break it.
The site has a bunch of other cool features that keep you engaged in the writing process, and it gives you a sense of being part of a community of writers.
It’s no longer free. After a 30-day trial, you have to pay $5/month (less if you buy a block of months at once) to do daily writing on the site.
HappyRitual.com
This site and app combo has a simple feature set that helps you keep doing regular habits.
I initially felt it was helpful but needed some improvement. But after a few months, the problem s with it irritated me too much, and I stopped using it. It may be okay for your purposes, though.
Access, cost, number of rituals, flexibility
You can access HappyRitual completely online, or you can get an iTunes, Android, or Playbook app. You can create up for four rituals for free. With a $2.99 upgrade or the purchase of a $2.99 iTunes, Android, or Playbook app, you can set up unlimited rituals and get e-mail reminders to do the rituals.
I like that the system is flexible enough to allow you to create habits you’ll only do a few days a week, though the implementation is a bit clunky and unnatural to me.
The e-mail reminders haven’t worked well for me. They come every day, but nowhere near the time I set for them. They also keep reporting about rituals I’ve deleted from the system. I find these e-mails, which tell me I haven’t done rituals that I’ve deleted and have no intention of doing, to be demoralizing and counterproductive.
Recording your success
One of the things that initially charmed me about the site is the way it lets you record your success. You get a calendar where, hopefully, you mark your successful completion of each habit each day. You get to choose the symbol you use from a nice selection. I’m an absolute sucker for yellow smiley faces, which are the default.
And, yes, I do get a little thrill when I get to add another row of yellow smiley faces each day. Because I’m hokey like that. Even more fun, when you complete all your habits for a day, the system rewards you with a group of people saying, “Yeah!”
Bottom line about HappyRitual.com
It’s not perfect, fancy, or complex, but it has some nice features. I initially liked it and used it regularly. Ultimately, the problems with it turned me off, and I stopped using it.
So I’m still on the lookout for something good. If you find any other good free or inexpensive productivity services or apps, please let me know!