On 1 Year of Being My Own Boss, Anne Lamott, and Treating Business Ownership as a Creative Endeavor

ServiceCrowd has been incorporated for a year now. We didn't really launch until November, and then pivoted our model entirely in the March/April timeframe, so who knows how we should be tracking our "anniversary" but making it a year since incorporation feels like a milestone worth celebrating, even if I definitely thought a year ago that I'd have more figured out by now.

But I don't have it all figured out. I have barely anything figured out, business-wise. And the past year has been a huge lesson for me in being okay with that.

I'm the kind of person who plans. Ask my mom, who I drive up the wall every time we go on a family vacation and I have each day meticulously planned out, tickets for the attraction of the day purchased, lunch and dinner reservations made. This is how I thrive. I love a journey, but I want to know the destination. Call it "Type-A." Call it being a "control freak." Hell, call it Capricorn Sun, Sagittarius Moon and Rising. Knowing where I'm going before I start on the trip is who I am.

But it turns out that when you don't have enough startup capital to run robust market research, when you don't have thousands of dollars to spend on ads where you could actually learn what messaging resonates, when you have to rely on your own network and voice and good work to take you anywhere, you can't really plan things out too far in advance. You kind of have to go with the flow of the market, which has, at times, been absolutely excruciating for me to deal with, psychologically. Should I take this particular piece of work that conforms with what we want to be doing, but can't pay what I think is market rate, or that piece of work that has absolutely nothing to do with our long term goals, but pays the bills?

A year ago, I probably would have told you there's a right answer to that question. Now? I am only certain that there isn't any point in saying "this path is right" and "this path is wrong" when it comes to these larger decisions about the business and about how I spend my time, because I've pretty much let go of trying to strong arm ServiceCrowd into being one thing or another. It is me and I am it and we will be fine.

I had the occasion to talk to Nathan Smitha yesterday (talk to? let's be serious here, talk at; there was definitely a long-winded follow up email sent; sorry about all the words, Nate) about Bird by Bird, the formative creative writing "manual" by Anne Lamott that you probably read if you took any creative writing classes in high school or college (I, personally, had an amazing literary magazine advisor in high school who had us reading it). We were talking about how hard it is sometimes to just sit down and get things done. Mostly around content for our new(er) pivot. Given that he didn't take any classes where he would have encountered Bird by Bird, I shared one of my favorite passages from the opening chapter about how she advises writers get things done on a daily basis ("Short Assignments"):

...all I have to do is write down as much as I can see through a one-inch picture frame. This is all I have to bite off for the time being. All I am going to do right now, for example, is write that one paragraph that sets the story in my hometown, in the late fifties, when the trains were still running. I am going to paint a picture of it, in words.

And it got me thinking not just about how having to produce content on the daily is a creative endeavor, because of course it is, but about how business ownership in and of itself ends up being more of a creative endeavor than I ever would have thought going into it.

By which I mean: When you sit down to write, or draw or paint or do whatever creative thing lights you up, you often have to let go of any preconceived notion of what the end result of that creative expression will be. Sitting down to write a fictional magnum opus about the Scottish aristocracy in 1413 is all well and good, but it quickly becomes entirely overwhelming (uh, is this an example from personal experience...maybe, maybe not). Instead, you have to really hone in on what, in particular, sparked your interest about this topic or subject, and just start writing in short assignments, shitty first drafts. Will you end up in the same place you thought you would when you started? Almost certainly you won't.

Will you end up with something good?

Sometimes! But sometimes it's absolute trash and you have to start again!

Do you have to learn to be authentically grateful for the reward of that creative expression in and of itself?

You absolutely do, or it will drive your Type-A, Capricorn Sun, Control Freak ass crazy.

Framing business ownership - agency ownership in particular - in this way for me has been incredibly freeing. I've found myself going back to Bird by Bird over and over again the last few months and distilling Lamott's advice into more generic advice that I think is so applicable to early stage businesses (with extreme apologies to Lamott):

• Break things into smaller tasks. Need to come up with a 12 month marketing strategy? All you have to do RIGHT NOW is write that 1 ICP down. Tomorrow you can do another.
• Perfectionism is the enemy. Embrace the messiness of what you're doing, and know you're probably going to get it wrong most of the time. This phase of your business is Lamott's "Shitty first draft" and you are going to rework, rewrite and replot later, so just get it down and out there. Or, to put it a more pithy way "Embarrassment is the price of greatness."
• "[Business ownership] is about hypnotizing yourself into believing in yourself, getting some work done, then unhypnotizing yourself and going over the material coldly." (Again, apologies to Ms. Lamott for just stealing that quote about writing directly!)
• There isn't any way forward except to be authentically yourself. Your voice is important in how you frame not just your content, but your company's values and aims. Make sure that they feel like really you and not like a version of you that you think others would prefer to see, or you will feel miserable all the time.
• Feeling bad about yourself is part of the process. Be grateful for the journey and what you learn about yourself, your own mind, and your own limitations along the way anyway.

Approaching the messiness of this early phase of the business the last couple of months as if it were a creative endeavor in its shitty first draft has left me feeling excited, humbled, grateful and feeling ready for whatever it is that comes next, be it 20 more years of ServiceCrowd or something else entirely. As someone with the words "What's Next?' tattooed on her arm, the answer to that question being "I don't know" and being okay with that has been one of the biggest positive changes for my mental health and well being that has ever happened in my career. I can't remember another time when I felt, well, inspired by the tasks ahead of me in my job.

I'm still going to plan out my vacations, though. Sorry, mom.