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The Newless Memo · Jul 24, 2026

Memo No. 14: The Diary of a 34 Year Old

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Anita Shannon · The Newless Memo

34 has landed at an auspicious time of my life. I am 3 weeks into full-time at Newless, I hit four years in London and it’s my first birthday as an engaged woman. 💍 So I am feeling reflective - particularly in the context of my career and ambitions.

So I thought I would share some more about me, my background and the updates of life - but in a way that leaves you with some hard, tangible pieces of life/career advice. This isn’t a damn soapbox after all!!!

Today I can say I am actively a “founder” in the fashion industry. So how did I get here? This is my trajectory to becoming a “fashion founder” (it’s long and messy):

  • 7 years old: I decide I want to work in fashion when I am older. I sketch fashion outfits on lined paper using colored pencils. Sadly, I cannot draw or paint for shit. I am not excelling in art class; I am more of a thinker and talker, sporty and social. I don’t think I am “creative”. I don’t think I will ever be a fashion designer. Sad!

  • 16 years old: I am good in school, I have a business mind and show leadership across all my activities. I decide to go to university for business. My best friend and I tell people we will study business in college so we can work in the “business of fashion” (whatever that means) when we are older. This sounds like a good plan.

  • 23 years old: I develop a passion for sustainability in college. I am now living in NYC and the concept of “sustainable fashion” is revelatory. I get very into rental, am an early, avid Rent-the-Runway member. Circular fashion wedges itself into my brain - “I will work in this one day”, but that day is not today.

  • 28 years old: It’s COVID, I am living in Berlin, I teach myself to sew - upcycle specifically. The mission of what I want to do is now very clear because of this: we should be making cute “new” clothes out of old clothes. I am still working in tech/real estate, but we are getting warmer.

  • 31 years old: I finally launch a version of Newless. We are slow, we are testing, understanding how the hell this can work. People like the concept, but I have to admit it hasn’t fully “clicked”.

  • 34 years old: We have relaunched as B2B. PMF (product-market fit) feels much closer. This is what I am going to do full-time.

27 years later. The thread remains. I knew what I wanted 27 years ago and I am only realllyyyy going for it today.

But each of those steps gave me something I didn’t know I would need.

Yet, I could have done this earlier - I could have started at 28 with my sewing machine. I’d likely have made worse decisions, but starting then wouldn’t have been “wrong”. I also could wait 3 more years, keep working, learn more - that could potentially make me a better founder. So what’s the lesson here?

In 2017 I tested a rental concept with my friends with cheaper, more "trendy" clothes. I called it "Tapas Style Co", the idea being bites of clothing instead of full ownership. Seduced them over with mimosas of course.

You might know what your ultimate pursuit is for 1 year or 27 years before you commit to it.

There is no correct number of years of experience that gives you permission to go for it. Waiting can make you more prepared, but it also can reduce the time you spend testing “the” thing. Both are real costs and you’re the only person who gets to weigh them. No book, no blog, no investor can tell you when it’s the right or wrong time to pursue your ambitions.

So when you feel the anxiety rising in your chest of being “behind” take a breather and know there isn’t really a timeline.

I joined WeWork in April 2015 - I am 22, in NYC, an early employee by all standards. I didn’t really understand what the company did, but I knew it was involved with startups, and I wanted to get exposure to entrepreneurship.

Six years later and It was the most formative stretch of my career, because WeWork in that era was the kind of company where if you were competent, you got pulled upward fast. I went from working a front desk to a senior director running a $50m+ business.

WeWork putting me on CBC News at 25 was wilddddd. Basically the CNN of Canada.

Then a lot changed at WeWork, and a former exec who’d become CEO at Knotel called and asked me to come over. I thought about pivoting into fashion right then. I didn’t. I didn’t feel ready, and this was a more senior job on a smaller team rebuilding a company out of bankruptcy - great experience. So I took it. I was there two and a half years, and it’s what brought me to London.

Through all of that I was earning significantly more than my peers and sitting in rooms well above my age. And I can say this without it being cocky, because it’s just the shape of the path I was on: if I had stayed in the corporate world, by 35 I would have been C-level with assets and equity in the millions.

But I was so fortunate to make good money young, because it gave me data-backed evidence that climbing a corporate ladder was not what I wanted to do with my life. I concretely knew that fulfillment or success for me is not fully monetary. But it is and should be for others!! Get your bag sis!

This is not a pretentious “follow your passion” piece of advice. Genuinely I often wish that being rich AF was my goal, it would be really fun and my wardrobe would be insane. But those experiences told me it wasn’t, and I couldn’t unknow it.

So I went the other way. I took a huge pay cut and became a Chief of Staff at a proper VC-backed B2B startup so I had the hard startup experience on my CV. And then I shifted to a founding team role at a consumer startup, another pay cut but more valuable experience.

And I was doing all of this while building and running Newless on the side, putting my own money into it, and using my savings as I needed to.

Yet with all the pay cuts, double hours and stress - I have never been happier. Because with each step it’s brought me one step closer to my ultimate goal.

The lesson is not “quit your job and follow your dreams”.

The lesson is not “money doesn’t bring you happiness”.

The lesson is simply know yourself. Reflect. Understand yourself and what actually makes you happy. Not what you think you’re supposed to want.

A job can be a boring means to an end. That’s okay!!! Maybe the burning passion inside you is to have a manageable career and amazing hobbies. That’s cool!! Maybe it’s to be a stay at home mom or dad! Love it - just do you babe.

But don’t let any blog, TikTok, podcast or whatever the f*ck tell YOU what YOU want.

A few months ago we decided to shift Newless from D2C to B2B. The mission has not and will never change: to make cute new clothes out of old clothes. Every version is simply a different answer to how. And we have had a few:

  • V1: Consumer Events: In-person sessions with our designers upcycling our customer’s clothing live. Prosecco flowing, music bumping, bring a friend - it was a social experience to replace what we lost with shopping. I still really believe in the potential of this model, but the brutal truth: events don’t scale and people are more price sensitive to events than clothing. The same person will spend £200 on a dress but only £50 on an event like this, even if the outcome is the same.

  • V2. eComm: We stood up a website that read like a cool D2C brand, same imagery, styling, etc. A very clear menu and paint-by-numbers approach: “you like this skirt? Great, send us some trousers”. I also really believe in the potential of this model, but you are asking for a lot of behavior changes from the customer. And, probably most importantly, acquiring new customers is very expensive. CAC has never been higher, and I am not a creator with a built in customer base. I could go for it, work towards that - but it’s just not my edge.

  • V3. B2B (technically B2B2C): Supporting brands to redesign their excess inventory into new on-trend collections. It’s already showing a lot of traction and there is just a feeling of everything flowing easier. It’s sort of a joke, but most investors will ask “can this be B2B?”. It’s generally safer, better odds of success, and your CAC drops dramatically.

Three of our designers, Scarlett, Hollie and Daiana, at our first official Newless pop-up.

Reads like a strategy, doesn’t it? So did I have a clear trajectory to B2B? Absolutely not.

There is a school of thought, and a lot of podcasts to back it up, to say that you’ve got to double down on your convictions. That you will get 100 no’s before that one yes that changes everything.

Not-not true!

But the reality is the decision to pivot and the decision to double-down are the same thing.

Let’s look at an example:

You run an ad campaign. It works really well. You run a version of it again, same spend, but it underperforms. Now: do you try again because it worked the first time, and you assume the failure was more a structure or timing thing? Or do you kill it, and eat the lost investment and allocate that money elsewhere?

Which brings me to lesson 4, and our final of the day:

That decision, in some form, happens daily. Half of the advice ecosystem would tell you that great founders knew when to change course, and the other half will tell you that great founders had the conviction when everyone doubted them. Both are true, because it depends.

In the moment you have partial data, a hypothesis, and a deadline. You make a call. You find out if it was right six to twelve months later, and by then the story has smoothed over into “we pivoted to B2B and it was the right move,” as though it were obvious.

It wasn’t obvious. It was a hard decision made with not enough information. Is it right? It’s too early to say. But I’ve gotta trust in my decision-making because if I don’t, who will?

So that’s 34 - a long thread, a lot of pay cuts, and a decision I won’t be able to grade for another year. But we are loving every second!

If you're sitting on something you've been circling for a while, the question I'd ask isn't "am I ready." It's "what am I actually waiting for." Sometimes that's a real answer. Sometimes it's just the anxiety of feeling behind, which we've established is worth precisely nothing.

Thanks for reading and tagging along - it means the world to have you here.

XOXO,
Anita

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