Notes from My Desk: How Failing at Copywriting Helped Me Succeed

Summertime is great isn't it? I'm actually in the Beartooth Mountains as we speak (hopefully not as scary as they sound) so enjoy this pre-scheduled delight of a post. I started this "Notes from My Desk" series which takes a more personal look at my life as an entrepreneur. I talk about the struggle to get where I am today, and the lessons I learned along the way. To read more personal stories, click here.


I've technically only been in business as Lauren Caselli Events since April of 2014. Before that, I was a copywriter for a year, and it wasn't until just this past June (like, last month) that I stopped taking copywriting clients.

But before I talk about how I'm just an OK copywriter, and how I decided to start saying no to copy projects even if it hurt my bottom line, I should probably talk about how I got here in the first place.


in New York City, which is where most humbling stories begin. I graduated from college in 2007 and got a job immediately that started three weeks after I walked across the stage at Georgetown University. I was heading to New York to plan weddings and, despite the fact that i had assisted at high-profile events, I had no idea what I was in for.

Y'all. Planning high-end weddings in New York City will bend you until you break. I worked for a wedding planner who didn't blink if we were in the office until 9pm and didn't think that we needed to ever have a conversation about paid vacation. It was intense. It was miserable. And it taught me a shit ton. (Shhhhh, don't tell my 22 year old self. She cried every day and couldn't wait to quit.)


mostly because I couldn't stand another 30 hour WEEKEND and because the woman I interviewed with didn't seem like the type of boss to throw misprinted invitations at me. And because there was promise of free food (and what broke 22 year old wouldn't have jumped at THAT chance?).

I stayed in corporate for 4 years, at the same firm, mostly because the economy came to a screeching halt about 6 months after I signed on. Nobody was moving jobs (people didn't even have jobs to move from, so who was I to think about my next upward career move at 23?) and so I thought it best to stay put...and read a lot of news articles on the internet. That year, I think I knew more about the fluctuations of the stock market than I knew about how to load the copy machine. And trust me, I loaded that dang copy machine so much the copy repair guys started calling me to fix things.


I had to go. I always thought I'd go back, but once you pay $585 for a one-bedroom apartment with million-dollar mountain views in Bozeman, Montana, that 3-bedroom closet with two Craigslist roommates and someone's rotating boyfriends for $1200 starts looking pretty unappealing.

But I digress.

I left New York to do some backpacking and to spend time in the Mountain West (this was 2012, almost 5 years to the month after I moved to New York). I also was feeling that antsy feeling that one gets when they realized that their life had been centered around work and getting a "good job" since they were 9.

My parents were children of immigrants, so I couldn't blame them for instilling the fear of poverty into me. But I just knew I was meant for something different. Which sounds so cliche I want to vomit. I'll clarify: I knew I was meant for something different, and my 27-year-old self thought that was sleeping in tents with dirty hippy boys 4 months out of the year.

(Spoiler: that is NOT in fact what I am meant for. Took me a lot of nights sleeping on the ground to figure that out, though.)


(Here's where the story gets good)

And despite my best effort to actually look at all the cards laid out on the table (Hint #1: Lauren, you've been in events your entire career. Hint #2: All your friends ask for your help with wedding planning. Hint #3: You love planning events so much it makes your molars hurt.), I said to myself:

"You know what business I'm going to start? Copywriting! I have no agency experience, and I don't really even have a great blog, but I know how to string sentences together so LET'S DO THIS!"

And while I'm clearly being very tongue-in-cheek here, I had no business starting a copywriting business except that in 2012, everyone had every right to start a business as long as they had a laptop.


because I had never started a business before AND I had never worked with a copywriting client before.

My best advice? Start your business with at least some vague idea of how to work with clients. Whether that comes from working with friends and family on your craft, or coming from an industry that is similar, it doesn't matter. What I can tell you is learning your craft AND simultaneously learning to run a business is some messy BS.

(Now you're saying "OKAY LAUREN, GET TO THE POINT!"

(Hold your horses. I'm almost there.)

The real truth? I struggled. And I ALWAYS freelanced for someone else while I was building my copywriting business. Because sometimes you need to have your rent paid before you spend two hours binging on Netflix in a creative slump. Part-time work helps ease that transition. It also gets you out of the house, which I can't recommend highly enough.


I sort of hated copywriting for other people. I hated the millions of revisions, and I hated coming up with 100 synonyms for "authentic." I liked writing my own copy and my own blog posts, but because I was writing so much for other people, I didn't have the energy or the time.


But not without teaching me EVERYTHING I need to know about business. I learned how to work with clients and how to manage their expectations.

I learned how to give proper deadlines and manage a workload.

I opened a dang bank account for my business to keep everything separate.

I paid taxes as a freelancer (ouch).

I navigated running a business and a relationship (poorly, I might add. Hopefully, I get another chance soon to try that one again.)

I inserted myself into my local community as a copywriter and got somewhat well-known locally, so that when I made the switch into events, I already had some history and a network behind me.

I learned how to structure my days.

I learned when to be hard on myself (September - May) and when to relax (June - August).

(Hey, those summer months in Montana are few and far between and you need to take advantage of them before they give way to snow.)

I learned that Netflix is my literal enemy.

And I learned that, no matter what anyone tells you, you can start one business, let it die slowly, and immediately after, start another one without too much fanfare.

So if you're worried about "not choosing the right business" then you shouldn't be a business owner. We all gotta work the kinks out one way or the other and the fastest way to untie those anxiety knots is to dive in, head first, and give it a try.

Your turn, #bosslady. Have you ever failed at one thing only to sweep up another (more successful thing) in it's place? Tell me in the comments below!