I’m sure I’m not the only one feeling reflective as the second decade of the new millennium comes to a close. At the end of the last century, I’d just finished high school and was skipping off towards a theatre degree in Chicago. The decade that followed was full of learning, art, failure, success, and ultimately deciding that while I will always be a stage manager at heart, the brutal schedules of live theatre and starving artist lifestyle just weren’t for me.
There’d been a few times during my theatre career where I thought event planning might be in my future (those fundraisers don’t plan themselves!) but it was my own wedding in 2010 which turned that fleeting whim into a real possibility.
2010: My Chicago Wedding for 75 Guests on $5000
Or, where the tiny seed of my future wedding planning business began to grow! On a hot AF day along the shore of Lake Michigan, I pulled off my very first wedding – my own.
It was just over three years of engagement, nine months of actively planning, and a fuck-ton of DIY and I loved just about every minute of it. (I had an experience that lots of LGBTQ+ people share: unsupportive parents. That wasn’t fun. Also not fun? The jacked-up pricing for chair delivery on a holiday Monday, which led to roping friends into helping with pickup and return to save money.)
But while I was planning, I got super frustrated at the lack of inclusion for LGBTQ+ folks throughout the wedding industry and the way it tries to shove every wedding into a very specific mold of The Way Things Are Done.
Coupled with my background in live events, an enlightening conversation with our wedding photographer, and a ton of compliments on our big day, I started toying with the idea of planning weddings for other people. By fall, I had done a bit of research, settled on a name, set up a website, and Crafty Broads was born.
2011: My First Year in Business
2011 brought with it my first professional weddings. I started out slowly, advertising in just one place, figuring out all the legal stuff you have to do for a new business, and testing the waters of wedding management. My wife became my business partner, heading up ur alterations & custom attire division and occasionally serving as my wedding day assistant.
I booked my first paying clients and helped four couples enjoy their wedding days without worrying about the details.
I charged way too little and worked my ass off. I got irritated on behalf of my clients about the same things that pissed me off when I got married. And I discovered (as I’d long suspected) that my theatre training melded seamlessly into weddings.
As someone who’d never had a particular interest in weddings, I was surprised to find that I loved being part of such happy, celebratory events!
2012: Trial By Fire and Travel
In my second year of business, I more than doubled the number of weddings that I managed, working with eleven fabulous couples to make their big days stress-free and fun.
With each one, I created new processes, became better organized, and figured out what questions I needed to ask in order to prepare for running a smooth wedding day! I navigated a few difficult situations and improved my diplomatic skills.
I got my first taste of destination wedding planning when my dear friend Kinzie and her partner Donnie hired me to make their wedding happen in downstate Illinois. An Indianapolis wedding for a San Francisco couple taught me how to plan virtually for a wedding market outside my home base a few months later. And I wrapped up my season with a lakeside wedding in Michigan.
To this day, I love traveling for weddings so much that it’s included in all of my planning and management packages.
2013: Building a Great Team & Going Full-Time
My third season of weddings brought the chance to dive deep into the planning side. After two years of rocking wedding management, I started booking clients for wedding planning and design, too. In 2013, I got to work with a total of 21 couples, four of whom took a chance on me to help them through the whole process.
We also realized we’d outgrown our home office and by midsummer, we’d officially opened the Crafty We had a very busy year!
I’d knowingly booked two weddings over Labor Day weekend. Since the first was a very small restaurant wedding with under 40 guests, I knew it would be ok to work another one that weekend. And because the second wedding, also relatively small at 100 guests, was on the Monday, I’d have a day off in between and no conflicts for rehearsal.
And then I made a huge scheduling mistake.
I met with a couple who had a Friday wedding planned at the end of August. I knew I wasn’t booked for anything in August yet, so I wasn’t concerned about the date. We hit it off, they decided to hire me, I sent off the contract and after they booked, I opened up my calendar to write it in.
That’s when I noticed that their Friday wedding – which remains the largest one I have planned to date at around 350 guests – was on the Friday of Labor Day weekend. Back to back to (almost) back weddings, starting with a massive wedding full of DIY projects and friends gifting talents. (There’s nothing wrong with either of those things, but they both make a lot more work for us planners.)
I needed help. So 2013 was the year I went from self-employed business owner to boss with employees. I was really picky about who I hired and it paid off. My first employee, Tamara, stayed with us for three seasons and when it came time for her to get married in 2018, she hired us to manage it!
I also needed more time. It had become increasingly hard to balance my new career with the nannying job I’d kept since my theatre days. So, in the fall I said a tearful goodbye to two tiny humans I’d spent most of my waking hours with for the last four years and started working for myself full-time.
2014: Full Speed Ahead and Still Learning
This year, I really started finding my groove. I’d more or less figured out who my favorite kinds of clients were (independent, feminist, LGBTQ+ folks tossing traditions that don’t suit them and picking new ones instead) and I booked my busiest season yet with 19 weddings. I hired three more part-time assistants to work those long days with me.
2014 was also a big year of learning and new experiences for me. I’d booked my first international wedding, in Switzerland, which I was just absolutely stoked about! A few months before the date, it was called off. Then I had a string of canceled weddings, a lot of unfinished DIY projects showing up on wedding days, one dissatisfied client which I took very personally, and several others who were just not a great fit for me and my philosophy.
While there’s nothing I could have done to prevent the called-off weddings, the other situations presented opportunities for improvement. With my team, we talked through the complaint and brainstormed how to make sure every client is thrilled with their planning experience. I re-vamped my contract and policies to be very clear about how we handle DIY elements. I adjusted my consultation process and became pickier about who I let hire me.
Just to be clear, though – this wasn’t a downer year! I also did tons of weddings with incredible clients that I absolutely loved, some of whom are friends to this day.
2015: Best Year Yet
This was an awesome year for me and my business! As in previous years, I continued to grow, learn, and have the best clients around. Truly, one of the things I love most about this job is the incredible people I get to meet.
In 2015, I did some of my favorite weddings of all time with some of the best people, both clients and wedding pros. It was a blast! I’d give you the highlights, but every wedding this year was a highlight.
There was Dan & Ashley’s wedding with Chef Michael Lachowicz’s 5-course French feast.
Sinead & Dave’s Redfield Estate wedding with a piñata for the kiddos.
And Claire & Michael’s pig roast and s’mores bar at Ignite Glass.
Then Joel & Rebecca’s rockin’ dance party kicking off with Raise Your Glass.
Alice & Zach’s epic wedding with a giant indoor swing for two and DJ towering above us with a slide for kids of all ages at the old Redmoon Theatre space. (Now Moonlight Studios. Get cool spectacle stuff for your events from New Moon.)
I adored Alyssa & Alex’s old Hollywood glam, art deco style wedding at the 19th Century Club. That bubble exit was the best!
Jodie & Jim worked his connection as one of the Smylie Brothers for their brewery reception.
Bettina & Chris were the third couple in one group of friends to hire me for their Monastero’s wedding. Carolyn & David brought me up to the Kenilworth Club (a venue I just love!) and Mary & Rob introduced me to the Floating World Gallery.
Darek & Shuling and Sarah & Paul must have great minds because they thought alike in their venue choices – we closed out the year with back-to-back weddings at Mrs. Murphy and Sons.
For icing on the 2015 cake, I was also named one of the Top 10 Wedding Planners in Chicago by Yelp. What a year!
2016: Moving On
I’m not going to bullshit you here: 2016 was rough.
Not on the wedding front – I had a great year with 14 weddings, including my best friend getting hitched in our hometown, St. Louis. It was another season with the usual ups and downs and lots of wonderful, memorable moments.
But on the home front, things weren’t looking so good. In December, my wife and I made the difficult decision to divorce, and with that came the division of the business we’d spent five years building together. I packed up and moved back to my hometown, St. Louis, not knowing exactly what was coming next.
2017: A New Beginning
This year was all about rebuilding. I overhauled everything, including my business name. Crafty Broads became Aisle Less Traveled; I dropped all sewing work and refocused only on wedding planning. I got a new logo, new website, added a bunch of new a la carte services, and basically started over.
It was harder than I thought it would be. I knew that a new brand would take time to grow but I didn’t quite realize how much it would be like starting completely from scratch. It didn’t help that I was in a different city where I hadn’t spent years already getting to know the local wedding scene.
I took on a part-time job to make ends meet, put my head down, and got to work. Travel became an even bigger part of my business, with all of my weddings for the year being in Chicago. I put a lot of miles on my little hatchback going back and forth.
I was fortunate to plan and manage five incredible weddings during this year of transition! First, there was Jessica & Ben’s wedding at a stunning law library in the loop. Jessica’s midnight blue gown was a beautiful alternative to the usual whites and ivories. Miniature sugar models of their cats adorned their wedding cake. And they had the most beautiful agate table numbers!
I planned with Kiley & O’Neil for about a year leading up to their wedding and I think they’d agree that it was everything we hoped it would be. We had an absolute dream team of some of my favorite Chicago wedding pros: Food Evolution (unfortunately now closed), Pollen Floral Design, and Christy Tyler Photography.
In September, I got to do something completely new when Mary & Pam chose me to plan their Chicago elopement.
A few weeks later, I wrapped up my season with Alexis & Josh’s wedding at Artifact Events and Hanna & Alex’s puppy playroom pizza party ice cream cart extravaganza.
2018: Super Gay Wedding
One of those pros became not just a friend but a podcast co-host. In February, we met up in Chinook, Washington to brainstorm and record the first bits and pieces of Super Gay Wedding. United by our mission to make the wedding industry inclusive to the LGBTQ+ community, Amanda Summerlin and I are interviewing couples and pros about their experiences.
In 2018, the Aisle Less Traveled team did six weddings in four states and I also began working with several clients on plans for their 2020 weddings.
March took me back to Chicago for Sarah & Joe’s St. Patrick’s Day wedding.
In the spring, I finally launched a project that I’d been dreaming up for years – the Choose Your Own Wedding planning subscription. Finally, there is an affordable wedding planner (me) for couples on limited budgets. I am so proud of this program and so excited to be able to help more people plan the weddings they want with a lot less stress!
In June, I was honored to assist with the annual PrideFest wedding in my neighboring county. Teresa & Shel had a 25-year history and four children between them when they tied the knot in front of a park full of Pride-goers and 50 of their closest friends.
Following that, I was off to California for James & Amy’s wedding while Kelly managed Francis & Rebecca’s big day in Chicago. July brought Anna & Dan together for another Chicago wedding.
In the fall, I managed Sam & Anneliese’s backyard circus wedding here in St. Louis, and we ended the year with former-assistant Tamara’s rustic wedding in Wisconsin. With a cheese fountain, of course!
On a personal note, just before the holidays, I met someone special. With my new love has come another round of evaluating my life and how my business fits into it.
2019: Change is Coming Again
In the final year of the decade, I am very happy about the path my business is taking! My subscription is growing, little by little, and my clients continue to be the best ones around.
This year, I spent a lot of time working on plans for next year’s weddings! It’s been an exciting year because I’ve had the chance to work with more couples on full-service planning – which means I’ve been having a blast getting to know them over many months as we dream and design their weddings together.
In April, I made my way to Covington, Kentucky (a suburb of Cincinnati) for Katie & Greg’s wedding at the Madison Event Center. My dear friend and fellow wedding planner, Bec, flew in to assist me and we had a blast!
Next up was my second year of assisting with planning the Pride St. Charles wedding. Chrisla & Pam are such a sweet couple and were married on the mainstage with their three kids serving as their wedding party.
In November, I started another huge transition: moving myself and my business to Seattle!
Remember that new love I found at the end of 2018? Well, little did they know when we started dating, but I’d been harboring a dream of living in the Pacific Northwest for well over a decade. So when they were offered a new job in Seattle, I was 100% on board!
I’m closing out the decade by settling into my new home, growing my relationship with care, and – as always – continuing to build Aisle Less Traveled to be the best it can be.
Here’s to another decade of new beginnings, love, and weddings!