On being a beginner... again

and again, and again!

What a week!

Firstly I want to say a HUGE thank you for your support with the second hand bag drop. I’m still not over the fact we sold out in less than 24 hours! To everyone who shared their love for it and of course — to the lovely people who bought the bags….from the bottom of my heart, THANK YOU!

I’ve spent what feels like the past month not wearing ‘real’ clothes (aka outfits that feel like me) thanks to my post surgery wound becoming infected and requiring yet again another trip to urgent care, a nasty shot in the bum and a fuck ton of anti -biotics. I have more style related posts in the works, but today, I just need to catch my breath. I wanted to reflect on this business venture, a sort of debrief and have a little catch up while we’re at it.

A while back, a friend had suggested I start my own handbag line.

‘You love bags and you have such a great eye’, I thanked her for her kind words, but immediately stated the obvious—that is, I don’t have the means to bankroll a business venture of that sort. The logistics (not to mention costs) seemed impossible: design, production, labor, marketing, pr… all for something I wouldn’t even know for sure I wanted to pursue full time. As someone who had only ever sold a service, and digital offerings, the idea of selling a tangible product was completely unknown. I had zero idea where to start.

But something about the idea stayed with me.

I knew I had no interest in making something new, (at least not at this moment in time) but I couldn’t lie that I did feel an affinity towards quality craftsmanship and a deep appreciation for bags, in particular second hand pieces that had already earned their stripes, and graduated with patina. Sometimes when an idea strikes you can see all the twists and turns and detours it took for that particular spark to manifest itself. The idea was to curate a collection of second hand bags.

Warmer, warmer.

Everything in this season of life has been led by my gut, with intentionality at the forefront of my decision making that has less to do with ‘should’ and more to do with ‘let’s give it a go’. Something about this experiment (that’s what I kept calling it) felt intuitive. It made sense to me. It felt like a natural progression, even if I were to do it once and never again. Could I make quality second hand bags feels as premium and desirable (if not more so) than the trending it bags? With enough newness in the world, there was only one way to find out.

And so the research began.

I wanted to create a bag drop that put second hand pieces in the spotlight. I wanted to demonstrate how many amazing pieces are out there, and that any of the pieces could easily hold their own next to the likes of the Row, Toteme or any of the brands I truly love, but most of which are currently out of my budget. I took my time finding each piece, with no set number of pieces to find, I just knew i’d trust my gut when it felt like the collection (I love calling it that) was complete.

I already used squarespace (not sponsored, but please sponsor me lol) for my website, and without realizing the template I had customized when I had my site designed already came with a commerce plan. So I started watching all the YouTube tutorials of how to set my shop up. I’m not naturally a tech wiz but I didn’t let that stop me. I’ve come to realize being a beginner is my superpower. I don’t like it, but I’m willing to do it. With each little tech hurdle conquered, my confidence grew, along with it a belief that I could really do this, and turns out..have fun while doing it.

I came into this with the background of someone who in the past led a team. One where everyone had specific roles, where timelines/outputs are shared and milestones are clearly defined. Well all that went straight out of the window, and I can safely say I had to fly the plane while building it! But something about the ‘bootstraps’ of it all was actually what I loved most about the whole experience. I loved watching it go from an idea to a reality. From making the website, planning the moodboards for each bag, shooting the images (didn’t my husband do a great job?!), to setting up all the tech and fulfilling the orders. I loved that I had no one to tell me I was doing it wrong, I just followed what felt right in the moment. Going back to wearing all the hats felt like such a full circle moment, one I’m grateful to say that with this project, I didn’t resent. Instead, I felt liberated by it.

I enjoyed putting so much care and attention into this passion project, especially with the knowledge it would get more second hand pieces in the hands of people who would breath new life into them. And I love more than anything that this was able to happen primarily on Substack, with this community. There was zero mention of this on my instagram, instead it felt like this really lovely intimate thing we created.

Dave winning all the awards and top marks for instagram husband of the year!

I’ve said from the beginning with Substack, i’d rather have one or two people pay me for my work than 100,000 people following it for free. I’d much rather be surrounded by a handful of good hearted people who value what I create, than millions shouting into the void expecting me to create things I have no desire to create. What’s best for me I’ve come to realize is better for you the community. You can’t create from an empty cup. The things I love to create the most are always born out of my curiosity.

My issue is this: when I’m excited about something, I find it hard not to go all in. I can’t lie I felt a little sad packaging my beloved bags not in a HH branded dust bag, or branded packaging, but I have to remind myself…baby steps. You’re not in a rush and there’s nothing to prove. Not to anyone, not even myself. I always want to run before I can walk but I have to get comfortable being a beginner again.

I knew I’d get things wrong, and while I knew I wouldn’t like that, I gave myself grace. I fulfilled every order manually (as I hadn’t figured out in the backend of my site how to set up automated tracking numbers) so let’s just say there were a few grumbles from the people in line behind me at the post office. But you best believe I wrote down every number diligently, assigning to each name on a piece of paper while screenshotting the packages tracking numbers as back up, no matter how long it took me (again sorry to anyone who stood behind me in the post office line). There were also other more boring things I got wrong (that affected me not the customer) with regards to the tax and shipping that I now know how to do differently next time. I’m learning.

It was genuinely surprising to me how much sleep I lost over handing over the parcels to the post office. That night as I tossed and turned I thought ‘what if they arrive damaged? What if they get lost in the post?’ I genuinely felt responsible for each and every piece…hoping with nervous excitement it’s recipient would love it as much as I would. ‘Will they care for it the way I would?’ Honestly…hours I laid awake feeling strangely attached to the fact these items had been in my presence. Each one was hand selected. I got to know each one. I had time to consider their story, and the next chapter awaiting them.

I had to remind my brain this is new. (Plus, that’s what tracking numbers are for Harry!)

I’m learning to enjoy chapter one without comparing it to someone else’s chapter 5. Who knows, maybe it will be a short story? Only time will tell.

It feels good not to know the ending.

Thank you so much for reading, and for being here.

Harry x

P.s. Should I do another drop before the end of the year?