How Many Times Do You Have to Fail Before You Succeed?

I was recently sorting through the old e-mails in the two and a half years of this blog’s gmail account. Besides using it for the blog, I’ve got personal correspondence in there and a lot of freelance-related conversations. It’s given me a timeline/picture of my first 6 months trying to make freelancing work and how I failed and succeeded my way into something that worked for me.

Looking at the big picture nearly two years later later helps me see how the failures were as important to me as the successes. Sometimes I made the same mistake twice, other times I learned my lesson quickly. Even once I started BlogCrafted, I wasn’t immune to hitting snags.

Here’s a timeline of what I tried, why it did or didn’t work, and what I learned with a good dash of hindsight.

Copywriting — 6 months to fail

My logic was as follows: 1) I like writing. 2) I majored in English and can write quite well. 3) There are a lot of people looking for content.

First, I got involved with a content production company who paid an embarrassingly-low amount of money. This was late 2007, however, and for copywriters without much know-how, experience, and preparation, rates were pretty low. I managed to make it work for a while, but within a month I’d said “no no no no.” I just couldn’t write 400-word keyword-rich articles on any topic at the drop of a hat. The payment didn’t make it worth my time.

After a little writing here and there (among other things, I tried sites like Associated Content & Squidoo, which pay per view and such), I landed a gig for most of the spring of 2008, writing content for two blogs. This was easier as it was on a particular topic, but it was also generally soul-crushing. It wasn’t like writing for a lot of the personal finance blogs which have teams of writers who provide engaging content, it was just anything remotely-related to the products that I could put up there. I tried to take pride in my work, but it was hard.

The pay was reasonable, so I stuck with this gig until I made the transition to full-time site work.

In Hindsight:

1) I’m not cut out for it. I like blogging, but I’m not cut out for writing content just for search engines and especially not on topics I just don’t care about. I still can’t look at water filters or dried superfoods without feeling a little sick.

2) I should have tried getting hired as a real blogger. If I was going the blogging route, I should have actively sought out jobs writing for a site that interested me like Wisebread. It might’ve taken something away from my blog, but being part of a community and writing about something I cared about would have made a huge difference to my morale and endurance.

3) I should have marketed my work properly and networked. One of my biggest failings in all my early attempts was not marketing and networking properly. I should have built a portfolio site, maybe with a blog, and generally gotten my work out there. The gigs I did I found through places like Craigslist and eLance…not the best places to get work.

4) I should have researched. I should have researched more about the last two before I started. I was getting out of a job I really hated, but even then I should have taken more time to look at how the better-paid people did this instead of just figuring it out as I went along.

Crafting — 1 month(ish) to fail

The other and much more short-lived freelance area I entered right off the bat was crafting. I like to craft and I had a few little successes both with selling pieces and with doing commissions. But I figured out crafting wasn’t right for me in the long-term much faster than I figured out writing.

In Hindsight:

1) I think my biggest failure was in not wanting to market. I also think that crafting wouldn’t have been the right choice for me, but for some reason I was scared to death of marketing my stuff. I think I was afraid people would find flaws in my work. Whatever it was, I psyched myself out of this one.

2) I didn’t have any particular product or brand. I made some cute little iPod cases and some lovely bags, but I didn’t really have a product or brand to back it up. It would have been hard to market without that, even if I’d tried harder.

It’s likely that I could make this work, but only if I had an inspired idea and took the time to build a brand and do it right. At the time, I was doing it because I could and without everything I know now about blogging, networking, branding, etc.

Copyediting — 3 months to fail

Even though my own writing isn’t always perfect, I’m pretty good at cleaning up other people’s writing. It’s easier for me to see the flaws in other people’s work and when I’m getting paid to do it, I get even better.

This gig doesn’t even need a hindsight section, however, because I learned very quickly that while I could clean up bad writing, I really didn’t want to. I ended up feeling stressed about whether or not I’d caught every error. I also had a hard time focusing on it for long periods, so I had to break it up. That wasn’t very efficient.

I’d much rather scan code looking for errors than copyedit a Master’s thesis (which I did).

Unfailing at Web Consulting

Fortunately, all the skills I was building through running a WordPress site were valuable enough for me to switch my freelancing focus entirely to BlogCrafted.

I learned from my past errors by:

1. Doing work that I enjoy. It’s hard to explain how much more I love this work than any of the three failures.
2. Creating a site to advertise my services and portfolio (though I’ve let the latter slide a bit by not updating).
3. Promoting and networking, both with clients and with other awesome folks who do the same work.
4. Valuing my work at market price.

At first I worried about whether or not I’d be able to get clients if I charged what it was worth, but when I made myself do it anyway I found that my business didn’t suffer and I made accommodations for a few people. I also had an unpleasant incident last summer with a client who wouldn’t pay.

I continue to learn, but, after doing blog consulting for nearly two years, I feel like I’ve actually succeeded as a freelancer. I’m glad the most cringe-inducing memories are two years behind me.

…And I Survived

None of these failures were of the “hit rock bottom and failed completely.” I didn’t have money invested in any of them, so while I lost time, earning potential, and sometimes undersold myself, I didn’t lose a great deal of money.

Your goal shouldn’t be to fail. You need to throw all your energy into the projects when you start them, full of hope and enthusiasm. I’m glad that the first three didn’t work out for me because then I really prefer web consulting work. But I think if I’d thrown myself into them with more planning and less trepidation, I might have done better before I figured out they weren’t for me.