Working For Yourself: Month Seven (Failing Forward)

{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.

Featured Sponsored Content

  • Yay! We are all so excited for you Meg :-) And as someone who is trying to go full time, I am so eager to go through all of the growing pains! I love what you say about falling forward. You have made so much progress so quickly! And how awesome for it to not just be about being self employed, but this amazing brand you’re building. Take some time to yourself to breathe. Much love!!

  • You are one bravy lady, I don’t think many of us could take on that kind of responsibility and still be (even mildly) sane. Take it slow and steady when you can and keep that hubby of yours close!

  • meg,
    thanks for giving us insight into the work that goes into making this community happen…

    Also, This: “There is grace in doing exactly what you’re already doing as well as you possibly

    • Yes, that’s the chunk that I copied to paste over here too. I need to focus on that bit myself over the next few months. Glad you’re taking the time to breathe, Meg!

  • “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.”

    come to think of it, that is exactly what i want to do.

  • Isn’t that funny how you have to learn stuff you never even thought about? I love “failing forward.” It’s perfect.

  • Jasper

    Breathe and take a vacation dear. You’re doing good, just keep steady on things. :)

  • You are magnificent! Keep on keepin on, girl!*

  • Meg,

    Thank you for this. As a first-time entrepreneur, I’m slowly learning to accept that this stuff is hard. That showing up every day, slowing down to make sure the work you’re doing is the work you want to be doing, and “failing forward” (I *love* this) is what makes it happen.

    But piloting my own plane is pretty darn awesome—even when I feel like I’m free-falling. :)

  • Marina

    Good for you. You have taken on some seriously big projects in the last year, and I agree with you that even with all the major changes behind the scenes, the content we all see here out front has consistently only gotten better and better. Keep doin’ what you’re doin’, because what you’re doin’ is really, really fantastic. <3 APW!

  • You are doing great Meg. Breath, enjoy, savour it.

    I love the concept of “failing forward”…

  • amy

    These posts are my favorite.

  • I love the mantra “Failing Forward”.

    As always, wise words and I’m scurrying to take notes.

    One day… one blissfully sweet day…

    More than anything, I love watching the business aspect take shape. It’s a hidden window into a foreign world, where before I only knew “I don’t have a boss sitting in the office next to me. Whoop!”

  • Congratulations.
    You are a living inspiration. Thanks for keeping this community going and for doing all the backstage things needed to keep it moving and growing (now you remind me of the story of The Red Queen, the one that tells Alice that she has to keep running just to stay in the “same ” place).
    Ohhh and vacations :) breath and enjoy !

  • Not Sarah

    I think that some of the reasons you outline here are exactly why I stay working for someone else. I need to do everything, perfectly, and exactly on time, which is incredibly stressful when I am doing work for myself. But by working with other people, I have a manager telling me to calm down when I need to calm down or saying that we just CAN’T fix that problem.

    I love what you’re doing with APW, that you were brave enough to venture out on your own, and keep it up!!

    • L

      I hear you on this one. My problem at the moment is that the pilot who IS flying the plane that I’m on is pretty awful at controlling turbulence. Also, my seat is a little too close to the front and I keep getting scary glimpses of storm clouds. All of that is to say that I’m thinking a lot about what it would be like to be in the control seat myself on my next flight and I love reading these posts about it.

  • Take a vacation!

    I’ve been completely amazed with how you’ve been tackling project after project this year: book, parties, vendor directory, etc. You deserve and need some recharge time. After all running a business is a marathon, not a race to the top.

    • meg

      Oh, we’re gone for the first half of September. Very, very gone.

      • Kayakgirl73

        Vacations are very important. I’m looking forward to my September California trip. We spending the weekend in San Francisco and then going down the coast to LA. I’ve always wanted to see the Pacific ocean for some reason.

  • Way to go Meg! :)

    Also, I love that the picture with the post is you leaning against the bathtub with a glass of hard liqour or possibly apple juice on the floor next to you. Hah.

    • meg


      • Caroline


      • apple juice, ha!

        I love these posts Meg. You came up with that perfect mantra “failing forward.” I think I’m going to tape it up on my wall. Despite being already married, I’ll keep coming back just for your wise pieces from this and reclaiming wife. thanks again, and again…

  • bec

    You have a great business head on you Meg. Thanks for inspiring and sharing!!

  • melissa

    I was really excited to come back from a necessary trip to Whole Foods (I have now found bulgur and know what it is.), and see several new entries from blogs on my reader. I saved this one for last to savor it.

    • I always save APW for last. Always.

      • melissa

        I usually read it first since it’s usually most exciting, but I thought I’d be all mature today. :)

        • lovelove

          I save APW till the end so I can be sure and read all the comments properly!

  • Oh, yes yes! Failing forward. That is SUCH a good way to put it. I have my own business, and finding the will to just keep pushing is the hardest part. And I have the same exact experience: when one thing goes wrong, a million do, and the best skill you can have is just letting it pass you by, while learning what you can from it, and not letting it hurt your ego so much that you can’t put yourself in a situation where you could fail. Yet again. July felt like that for me. August is feeling better.

    Keep at it! You’re awesome.

  • Steph

    Love love love these posts! I’m not in a position a this exact moment to fly my own plane, but I am still learning so much about the process through you and these posts. And I’m so happy for you and excited that you are living out your dream. Hard parts and all. Keep flying high and thanks for letting us share the ride :)

  • I will be reading and reading these posts over and over again – because I JUST QUIT MY JOB! I have decided working for myself (full time planning. DOC) is worth being scared. I actually said to myself “If I had to choose happiness and eating ramen noodles or working here miserable eating steak. I choose ramen and happiness” Now – if I had been making enough to have Per Se steak, that’s different. Since I was at Outback level, though, I am making the leap!

    I may throw up now, but will keep reading about your inspiring journey.

    • DanEllie

      What an amazing leap! Good luck to you and best wishes for the future. Stay strong in mind (and stomach!)

    • Congratulations Kari!!! That’s huge and exciting. :) Wishing you all the best in this new chapter.

  • Kaitlyn

    Love! As always, Meg, exactly what I needed when I needed it. I don’t work for myself, but I did just transition to more of a self-directed roll doing all sorts of things I have NO CLUE how to do with no one around to teach me. “Failing forward” is precisely what I’m doing.

  • Marisa-Andrea

    Funny thing is for me, initially, self-employment WAS scary for those very reasons. In fact, my biggest concern and worry before plunging into the scary unknown WAS “what if I fail and make no money?” And I guess it was legitimate being that lawyers, particularly young ones, are facing the worst job market in a generation. Or two. But really, if I made no money, I guess I’d just do what I did before: get a job. It’s strange how a year and half ago, that answer seemed so unfathomable whereas today, it’s really quite simple. Self-employment is more and less stressful in some ways. Being the person who makes the cogs work…well that’s pretty stressful when you know that every two weeks, someone is expecting and, ahem, DESERVES, their paycheck or you have commercial rent to pay. And it’s less stressful in that I can focus on the big stuff and not agonize over every little single detail of my professional life the way I used to.

  • Marchelle

    Inspiration times a million.

    Then again, you knew that. :)

  • LPC

    Oh yes. So glad you are taking some time, in place, to comprehend and set up systems. I am happy and proud to be involved in your thinking.

  • Kee

    I’m also running my own project and I really like that you are taking “a break” from expanding. It’s easy sometimes to get caught up in success and increased income and more staff and you just want to go go go go and do EVERYTHING AND TAKE OVER THE WORLD (at least that was what I was thinking when I first expanded and it went well).

    But I do think that improving one thing at a time and then leave a period for it to really settle and stabilize is better in the long run, than rushing to make more money and hire more people and do everything immediately. Getting accounting systems in place and making sure that everyone is managing well with their current tasks is really really crucial for sustainable growth of a business or a project.

  • Class of 1980

    How come every time my name gets mentioned here I’m MIA for the day? So here I am, commenting to an empty room.

    Anyway … MEG WROTE:

    “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.”

    You’re inside my head.

    I used to think it was so lame when people would be against a presidential candidate just because they never ran a business. Now … I have to say I understand what they’re getting at.

    Running a business has changed me, and is still changing me more than any experience of my life. I feel like I was an infant before that as far as my understanding of The Way Things Are.

  • Pingback: Working For Yourself: Month Eight (Hard-Earned Freedom) | CHI Turbo 2" Ceramic Flat Iron()