Working For Yourself: Month Eight (Hard-Earned Freedom)

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

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  • Anne

    So, not at all related to this post, but something I’ve been noticing over the last several weeks or months: Meg, you have the cutest collection of dresses ever.

    • And even better than that…you look so happy in that picture.

  • Anne, Right?

    Meg, you’re an inspiration. You’re doing what I strive to do, and via posts such as this, it seems *almost* possible.

  • You’re inspiring to us all. Knowing it’s possible to work for yourself keeps me pushing towards that goal.

  • Yes to all those little prayers… And yes to gratitude and enjoyment when they finally come true. Well done, Meg!

  • As I sit here, on my patio, in the beautiful North Carolina weather, being kept company by my kitties, I think of you as an inspiration. I am on a short “lunch” break and in a few minutes I’ll go back to writing an article for an awesome newspaper that I write for. I freelance for. I work for myself. Sure, I “work” for other people, but I am so, so happy to be able to do what I do. It’s so hard, especially since we really can’t afford this, but I’ve never been so happy in my life. I hope that my blogs are able to take off and I will completely and utterly work for myself one day, but for right now, this pseudo-self employment is pretty awesome. Thank you for sharing your journey.

  • Let me preface this that I don’t mean it to be at all snarky:

    “I’m not going to send business emails while on proper vacation; I’ll loose my mind.”

    You probably meant “lose,” which is a typo we all make all the time. But in this case, it was such an appropriate typo. If you were going to answer all those emails, you just might lose your mind. But since you’re not, your mind is loose, free to do whatever it pleases for a couple of weeks.

    (I like happy typos.)

  • “and then I took a nap”

    Stress, followed by relaxation. Congrats, girlie!

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  • Not Sarah

    Congrats! You have accomplished so much in the last year.

    Happy vacationing! You deserve it.

  • Tamara Van Horn

    Thanks Meg! The lessons about maintaining boundaries (and not) are the message I need right now. Have a wonderfully unplugged vacation!

  • I hope you have a very restful and rejuvenating vacation. The hard work is really paying off. You are definitely changing the world of weddings for the better. You deserve the break.

  • Brianne

    Meg, I don’t comment much, but know that I truly love and appreciate the risk that you took to make this blog (a blog that kept me sane and motivated through my own wedding) your job. It makes me so happy, and as I am just now on the verge of starting my own non-profit, makes me feel like it’s a possibility. Enjoy your much deserved break!

  • Lily

    You have accomplished truly amazing things with this blog and all that has come along with it (blog feels too small for this operation). So glad you can relax and unwind and take stock of this magnificent thing.

  • Well put. I’m stil figuring out how to take a vacation in the version of self-employment I’ve chosen, but when I do I know it’ll be worth it.

  • Oh my god. Your post could not have come at a better time. I’m not self-employed (though last year I did try SO hard to make it work for myself). Rather, I just started a new temp job at a big agency. I was thrilled about it last week. This week it hit me like a ton of bricks. I’ve been overcome with that feeling of drowning in someplace new…where everyone speaks a different language and you can’t keep track of all the projects you are now responsible for…all at lightning fast speed and such limited training! Ah, its been a rough rough week. I am hoping and praying for the little bit of light I see at the end of the tunnel to shine on me full force. Thank you for your inspiration. Many of the stories within this blog have helped me through my past year and I just knew that today would be no exception. Thank you.

  • The challenges of being self-employed are like working on a startup where your time, energy, and commitment are worth more than ANY investor. Of course, it means the payoff is worth more than cash (admittedly, the cash isn’t bad either!). Here’s to continued success!

  • april

    Many, MANY congrats to you darling Meg. It’s such a treat to watch the success of APW grow on a daily basis. Well done, lady!

  • maile

    Relating to this post so much. Overwhelmed by all the awesome that you are. You are such an inspiration and should be so proud of everything you’ve accomplished. Also, that photo is gorgeous! xo

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