Posts Tagged ‘Entrepreneurship’

{Me, on vacation, with the text of The New Yorker all over me}

This month I spent half of it halfway around the world on a mostly-unplugged two week vacation. I spent the other half of it back in San Francisco, hard at work. And I’m typing this from a runway in Seattle, on a delayed flight to come back home after moderating the Offbeat Empire panel at Geek Girl Con this weekend. That sort of sums up this month: wonderful and nuts. Or as I like to think about it, finding balance between two extremes.

Self employed small business owners are always telling me how they can’t take vacations, and I’m always arguing that as a small business owner you can’t afford not take vacations. Yes, most of the time self employed vacations are not going to involve international trips (though the more of those we can pull off the better), but if you can’t take time to totally unplug, to stop answering emails, to get out of the office (by which I mean your house), and to just STOP, you’re not going to get a chance to see the big picture of what your business needs, and what you need. The first half of the month I spent time staring into space and napping, lying by the pool and reading the New Yorker (see above), but I also did a lot of on paper journaling. I’d stare into space and think about what wasn’t working in my life and business, and then stare at my journal and write lists, ideas, thoughts. And by the end of the two weeks I had a far better idea of what I wanted my next steps to be, what my big picture goals were for self employment, and what I needed to change right this second. And what I needed to change right this second was fixing my business infrastructure and working smarter. I needed to spend more time doing big picture stuff, and less time focusing on tiny details.

When I got home to San Francisco, within a few short days I’d handed in my final edits on the APW book (It was funny: when I saw the index for the first time, it finally hit me. I’d written a real life book with a real life index, holy shit what was that). And just like that, for the first time since I started working for myself full time in January, I didn’t have a book to write. And the amount of extra time and breathing space that gives you is intense.

So I did common sense things. I talked to my staff to get their feedback about what was working and what wasn’t. We made some invisible to you but huge to us editorial changes (hint: edit flow and editorial calendar plug ins). I had a long meeting with my excellent accountant where I finally handed day-to-day book keeping over to him, so I could keep track of what I was making on a month-to-month level, instead of only doing the books in a flurry of stress once a quarter. (Hint: just because you can do it yourself—and I’m good at Quickbooks—does not mean you should.) I worked on my 2011 budget. I made the first steps on building a foundation for new, post-book projects. And I even took an afternoon off now and then, to enjoy the finally-emerged-after-an-awful-foggy-summer San Francisco sun. I started a needlepoint project, so I could calm my mind after a busy day of working online. I spent a little more time with my husband.  And for the first time this year things felt a little bit easier. I had a little more time for gratitude. I had time to think about how this blog has grown since my full time leap in January, and how amazing all of you guys are (even the quiet ones).

And then this weekend I dashed up to Seattle to Moderate the Offbeat Empire Panel at Geek Girl Con. I’d never been to Seattle, which is very pretty. But mostly it was amazing to spend the weekend with the Offbeat Empire team. Ariel and I kept cheerily introducing each other as, “This is my closest competitor,” which is totally true. But it’s great to live in a world where I can hang out with my closest business competiors, and we can trade advice, and try to help each other create more awesome. And my roomates the two different nights, Megan Finley, Managing Editor of Offbeat Bride, and Cat Rocketship, Managing Editor at Offbeat Home, are awesome, hilarious, smart ladies. And that was even better.

So onwards and upwards. I hope to close out the last of this year with more balance, more breathing, and more sharing of ideas. And oh yeah, a book I wrote. Because that’s totally happening too.

The last two months, I’ve talked a lot about the ways working for yourself is hard and overwhelming. I’ve talked about the stresses of running a small business, and about the feeling of failing forward, over and over again. This month, it felt like the sun finally broke through the clouds. It felt as if all the work, and stress, and confusion paid off, and I remembered why I was doing this.

I spent all of last year focused on building APW so I could quit my job. Every single morning, I would hop over the cable car tracks in my high heels, running to my job as a (fancy) secretary—a job I’d taken just so I could fully get APW off the ground. And every single morning as I did that, I’d say a little prayer, “Please, let me sell the book. Please, let me work for myself. Please, let this be worth it.” And then it happened.

But this year has been such a whirl of adjustment that it’s been hard to focus on the fact that I finally got what I wanted. I figured out how to write a book… and wrote a book; I got an office, I gave up an office; I figured out accounting, I fell behind on accounting; I got a staff, I realized I had to learn how to be a boss. It’s been really complicated. And in the midst of that complication, I kept looking back on myself last year and saying, “I got it. Now I’m going to try really hard to enjoy it fully.” But it’s been hard. Complicated.

But this month, when I went to New York City a few days early just because I call the shots in my own life, it really hit me. I worked in the park. I worked in the beautiful public library. And in those moments, the fact that I had earned the freedom to work in the park on a beautiful summer day hit me at gale force. Self-employment wasn’t easy, but it was worth it.

And then there was Yay New York. We threw Yay New York in seven weeks, and during that period I consistently felt overwhelmed and like I was failing. Tickets were not selling fast enough. We were not lining up sponsors fast enough. I was afraid I’d taken on too much. But when it came together, it was magic. It made me realize the hugeness of what I’d undertaken this year: the business, the growth of the website, the growth and deepening of this community, and now two weddings and a party. The failure was worth it.

Right now, as this post goes live, I’m far away on vacation. Taking vacation as a self-employed person is hard, and most people I know don’t do it. I spent the week before I left getting three weeks of work done in one week (while recovering from Yay New York). I had to make sure systems were in place for things to run when I was gone. When I get back, I’ll have to catch up. But for me, someone who occasionally has to send business emails at intermission of a Broadway show, it’s necessary. I’m not going to send business emails while on proper vacation; I’ll loose my mind. I’m totally unplugged right now, not checking Twitter, not checking the blog, not checking email. And that’s what is going to give me the power to get through the remaining months of the year, doing what I love.

This month, I was reminded why it was all worth it. And then I took a nap.

Photo: Me on Katie Jane’s roof the night before Yay NY, taken by Amber Marlow Photography

{Photo by Maggie, just because I like it.}

This month has felt less about self employment and more about running a business. And running a business can be a bit high-stress and tricky. I’ve had days this month where I spoke to two lawyers (only one of whom I am married to), an accountant, dealt with a budget issue, managed employees, and chatted with our web designers, all in the same day. On days like that, I miss just sitting down at my computer and writing. But I’m also proud of all the myriad types of work that go into making APW tick, and I’m proud to be learning how to do all of them.

In the second half of my first year of self-employment, I’m coming face-to-face with the fact that this undertaking is a complicated one. When I quit my job, it was easiest to look at the year as just a continuation of the work I’d already been doing (plus a book): write posts, sell ads, grow traffic, use new-found time to write book. But it’s not really like that. To run a business well, you have to think about how your budget is going to play out over time, how you want the business to grow (and how you don’t want it to grow), what your employees need, legal issues, and, well, more. That, and you need to keep sitting down every morning to write. It’s hard, but the freedom that it gives me, along with the ability to do work that I love, makes it worth it.

When I wrote my last post on self-employment the ever-wise Class of 1980 commented, “Self-employment takes you closer to the way things really work. Instead of being a crew member on the plane, you are piloting it… and Oh My God just the slightest touch on the controls makes the plane do big moves!” I’ve been thinking about that comment all month. People think self-employment is scary because your business ebbs and flows, and you might lose your income. But that’s not true. Self-employment is scary because it shows you that business always ebbs and flows, and you just haven’t been looking directly at that fact for all this time. If you make a salary, there is someone above you, with their hands on the controls, trying to make the plane fly smoothly, so you still get your paycheck. Turns out, I’d rather be flying the plane than not. Of course.

At points during this month, while I undertook a variety of new-to-me projects, I felt like I was failing, over and over again. My mantra on those days was “Fail forward.” And I kept reminding myself that the only way I know to be successful is to fail, over and over again, and learn from it. On a particularly rough morning, Lisa of Privilege reassured me, “If you aren’t failing here and there you are certainly leaving money on the table somewhere else.” And I realized, yes. We fail when we want to test the boundaries of what we know how to do well, and that’s how we grow.

Which isn’t to say that things have been all hard all the time around here. APW made and sold its first merchandise this month, to a smashing success (those tote bags sold out in 72 hours, and we ordered a limited additional run, which is also almost gone). We worked to plan a big party (which looks like it’s going to be so fun that there are no words). I spoke at a wedding event, which was smashingly fun, if funny. I finally announced the APW Vendor Directory, which is shaping up to be truly excellent. And, most importantly to me, we’ve been consistently producing content here that I’m deeply proud of.

But mostly, I realized that I’ve been sprinting like a madwoman all year, and it’s time to slow down. For the first time, when people ask me what my next project is, I’m telling them, “Nothing.” Of course, I’m me, and that really means, “Nothing right this second, at least until my book is published in January.” I’m planning to spend the fall breathing, getting systems in place, and making APW run as well as it can. Getting accounting systems in place might not be glamorous, but it’s important, and I’m going to focus on it. There is grace in doing exactly what you’re already doing as well as you possibly can, and that’s what I hope to spend the next few months doing.

That, and taking a vacation. I need it.