Dead plant

All Thumbs: How I Fumbled Through Year One

on Jul 27, 12 in Business Basics, Productivity by with 8 Comments

I’ve always been bad at growing things.

Like, really bad. They’d always start out doing well. I’d set a basil plant up in a sunny spot by the window and it would begin to thrive. But at some point in the process, I’d begin to forget about it. Or I’d go on vacation and come home to realize I forgot to ask my roommate to water it. Or I’d overwater it and it’d grow mold (true story).

Despite that, I’m trying to grow my own garden this year. I knew when I planted it that it didn’t have a very good shot. And a few of the plants did the predictable thing: they shriveled up and died. But surprisingly, most of them have instead begun to bear fruit.


I started the garden a bit late in the season, yet as of this week I have several baby jalapenos, a baby cucumber and an array of herbs growing on my back patio. I’ve let go of those plants that died and instead focused my attention on those that continue to grow.

Yet I’ve been having a problem doing the same when it comes to freelancing.

Ready to Call It Quits

Monday night I was feeling so frustrated I began browsing “wanted” ads on Craig’s list. Freelancing seemed easy when I was planning out this first year—I was going to avoid all those mistakes other freelancers mentioned. I’d make sure to set aside income each month for taxes; I’d avoid going paycheck to paycheck and the usual “writer’s up-and-down” by paying myself a steady salary… on months that I made more, it would go into savings. On months that I made less, I could draw from my savings.

But then reality set in.

On Monday I spent the day focusing on my business—and by the end of the day, I was very aware of how different reality was from the expectations I’d had before going freelance. Of course, I’d known the two weren’t really matching up, but it was easy to push it out-of-mind while I’d been swamped with client work. After all, I was busy; that meant I was doing well, didn’t it?

Except I was busy because I had to be just to earn enough to live on—without setting aside money for taxes. And rather than establish a set pay rate and save, I’d been simply using the money I made in a given month the following month; that is, the money I made in June is money spent in July and the money made in July is spent in August—because otherwise, it would be a real struggle to pay bills.

Trying to Get Back On Track

Now, almost a year out of the hole, I’ve finally raised my rates (though probably not enough) and am learning how to maximize my productivity during working hours. I’ve actually figured out what I need to make in order to set up my finances the way I’d like (so that I can pay myself a steady paycheck and set aside money for taxes). And I’m finally beginning to make enough so that I don’t have to struggle to make ends meet.

However, I’m still stuck playing catch up from all the months I was doing that “making ends meet” thing. In other words, when it comes to my business I’m still struggling to save those dying plants. And honestly, I’m not sure what to do about it.

I know I need to let go of what’s already gone—but how do you “just replant” with a business? I can’t simply write off most of this year and chalk it up to experience. I still need to even up with Uncle Sam come tax time. And I’m just not sure how to go about it.

But here’s what I’m betting: I’m betting that a few of you have been where I am. Maybe you have a few words of advice. Maybe you just have a sympathy story. Either way, I’d appreciate you to share in the comments—and in return, I promise to share where I go from here.

Got any advice for a new-ish freelancer? Lay it on us in the comments below.

photo by: jblahblahblah

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8 Responses to All Thumbs: How I Fumbled Through Year One

  1. Kate says:

    Ugh, how frustrating! I’ve been following your journey with hopes of being able to be a freelancer someday myself. I don’t have any tips about squaring up with Uncle Sam, unfortunately. Good good good luck and I’m looking forward to reading others’ suggestions.
    Kate recently posted..Upcoming Events at Vollsjö Mill

    • Melissa says:

      Hi Kate,
      Don’t let my story above scare you. Although I’m still working to grow things, I’m also on schedule to make that new “goal income” starting in Sept. from there, hopefully I can stash away enough to even things up. The nice thing about not making much is that it means I owe less in taxes—but it’s definitely important to have funds saved up prior to leaving for the freelance life (probably twice as much as you think you need) and then to keep in mind that Uncle Sam gets about 1/3 of any money you do make.
      Melissa recently posted..Giving the Cat Aisle a Boost, Pet Business Magazine

  2. I’m glad you wrote this for two reasons. The first is that it’s important for people to remember that you can research and plan all you want but the practical application is always a little challenging. And you are the best prepared person I’ve ever met when it comes to taking the Big Leap. The second reason is that there are tons of other freelancers going through the same thing and it’s important to talk about these things.

    I think I already gave you my thoughts on the subject but I’ll rehash them here for people who aren’t privy to our IM conversations. I think it’s a combination of not charging enough, not prospecting enough, and not using work time to only work on work. Now is a good time to hit the reset button. Do some comps on similar freelance editors to see where your rates should fall. Come up with a solid marketing plan and stick to it. And finally, do not think that just because you are sitting at your desk, it means you are working. Take a hard look at what you’re doing there for ten hours a day and you may find that there are ways you can decrease your work time without decreasing your rates, which means you make more money without investing more time.
    Princess Jones recently posted..June Brain Candy: The All About Expectations Edition

    • Melissa says:

      PJ, just to saw it publicly… this is why I appreciate having you there to vent it to so much. You’re willing to shoot back at me with the truth of what I should be doing differently, without pussy-footing about it. Since our IM chat, I’ve been working on both the prospecting end of things and the productivity angle. So far, things are looking much better. Not 100% fixed, of course, but change only happens so fast….
      Melissa recently posted..Giving the Cat Aisle a Boost, Pet Business Magazine

  3. Anne Janzer says:

    Courage – you’re thinking about it like a business, which is essential. Freelancing takes discipline – but the business does grow. The first year is toughest in terms of the tax thing. Next year, you figure out what you owed this year and pay 1/4 each quarter in estimated quarterlies – and keep aside a buffer based on whether your income is increasing (yes!) or not. (The usual disclaimers apply, I’m not a tax person at all and hire a professional to do this stuff.) But you are a business with overhead and taxes, and your rates need to account for that. And you cannot let your clients define your business, you need to take responsibility for marketing even when you’re busy, and for charging rates that you can build a business on.
    Anne Janzer recently posted..Freelance horror stories: The consulting contract

  4. I’ve been self-employed for almost 18 years now. The most important thing I’ve learned that it’s important to do, besides charging high enough rates, is doing at least a little bit of marketing every single workday. Marketing doesn’t always pay off immediately, but over the long term, it helps even out the feast-or-famine cycle. And marketing can take so many forms: http://editor-mom.blogspot.com/2009/07/marketing-tips-for-freelancers.html

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