What I learned freelancing for a startup

It was a crazy fall. If you’re a regular WordCount reader, you know I wasn’t around much between Labor Day and Christmas. There was a good reason: I’ve been working for a startup.

I’ve worked with startups before, most recently freelancing for  Entrepreneur Media’s SecondAct.com website for its entire two-year life span (I’d link to it, but Entrepreneur took down the site). I wrote for The Industry Standard during its dot-com era heyday, and before that, worked as a contributor or staff writer for several long-forgotten tech and business magazines or weeklies.

This time, I’ve been working as a part-time editor for a startup website for people who are looking for a new job or want to find out more about what it’s like to work at certain companies.

Startup Energy

There’s an energy to startups that is unlike any other. If you’ve worked for one, you know what I mean. It’s so exciting: You’re making it up as you go along. There’s so much to do and not enough hours in a day to do it. You’re always on deadline.

It’s also can be an enomously frustrating: You’re making it up as you go along. There’s so much to do and not enough hours in a day to do it. You’re always on deadline.

In the end, though, I thrive on the buzz. In this particular situation, along with editing and writing, I’ve had the opportunity to help build an editorial department, including writing job descriptions, helping the organization design story formats and style guidelines, search for contributors, and lead trainings.

I’ve also learned a lot about patience, sharing what I know, teamwork, hiring and showing appreciation – not to mention getting a crash course in GoToMeeting.

Freelancing for startups 101

If you’re contemplating taking a freelance writing or other gig with a startup, here are some things to know:

1. If you say yes to a startup, you’ll say no to a lot of other stuff.

When I said yes to the startup, I had to shelve an assignment with a top publisher — so painful. Luckily for me, I heard from the editor there recently and he doesn’t hate me. In fact, he asked for pitches. (Cue major sigh of relief).

I also had to shelve some other things. This blog was one of them. There was a time when I would have managed by opting out of weekday workouts instead of dropping paid work. Been there, done that, and it wasn’t fun. This time, I put me first and let blogging go until I could manage it again.

If you say yes to a startup, know what you’re getting yourself into and that it might mean curbing some other work. Or set limits on what you’ll do, either by building them into whatever contract you sign, or at least creating some internal limits.

2. There’s always more to do than your time or resources will allow.

This was one of the hardest things for me about working for a startup. The group I’m working with has a mountain of great intellectual property that they could capitalize on in mutliple different ways. Because the division  is new and has a limited staff and budget, there’s only so much they can tackle at a time. As a result, we prioritize what has to be done now and the rest waits until later. That’s a lot of waiting. As an ex-daily newspaper reporter, I don’t do waiting very well. But I’m learning.

3. Good enough is good enough.

When I started working with the startup in mid-August, we were a month away from their second biggest deadline of the year.  Four weeks out, I put a lot of thought and care into the material I was editing, and more often than not, asked for revisions. As we got closer to our deadline and work inevitably backed up, we needed to speed up the editing process to make sure that we’d get everything done on time. That meant asking for fewer revisions and the majority of the time settling for B work instead of going for A+. Or as my boss said, “Just make it good enough.”

For many thing, good enough really is good enough, especially if you’re working on something that you could later update or revise. One caveat: the good enough mentality does not apply to the facts of a story, quotes or proper spelling and punctuation — no cutting corners on those.

4. You’re only as good as your team.

When you’re working under a tight budget and time restrictions, everyone has to pull their weight. There’s little room for people who can’t keep up, or who need a lot of extra coaching – or extensive rewriting. Having writers we could depend on to turn in clean copy and hit deadlines was critical. Some contributors we brought into the project who seemed promising ended up not being up to the task for one reason or another. It didn’t take long before either they bowed out or we stopped working with them after they’d completed their initial assignments.

It’s not fun for anyone when things don’t work out, but it’s even less fun to continue a working relationship that’s an obvious bad fit. You’ll know when someone’s a good fit — I’ve literally shed tearings reading someone’s copy thinking “Yes, they get it.” When you get keepers like that, it’s important to let them know how much you appreciate them, especially if you want to keep them on the team.

5. There are always new things to learn.

Remember what I said about learning how to use GoToMeeting? I learned how to use it to run online meetings. My favorite feature: taking over other participants’ computer screens to lead walk throughs of material on my screen. I also learned how to use Sharepoint to share documents, and a web-based editing tool.

All of those tools are now part of my editing toolkit, which I can post on my LinkedIn profile for other publications that might be interested in working with me someday to see.

6. The stories might be done but the website never will be.

Over the fall, the startup launched a web-tool for editing and database management. Freelance writers and editors working on a big project were using the web tool days after it launched. It wasn’t perfect; in fact, for a time, the editing panel displayed copy only in tiny 8 pt. type and didn’t include some standard features of most text editors, such as a spell checker. With the biggest deadline of the year before us, though, we couldn’t wait until the website was perfect to start using it.

That’s the thing about startups. You can’t wait until things are perfect to pull the trigger. At some point, you decide that what you’ve got is good enough to launch (see #3). Then you make do with the bugs and quirks until the first update.

It helps to keep a list of everything that doesn’t work as well as it should, or features that you’d like to add, so when that update rolls around, you’ve got something to give to the website team and you don’t have to rely on memory for those things that were driving you crazy.

What have you learned freelancing for a startup? Share by leaving a comment.

[Flickr photo by katerha]