The Irony of a 10-Year Anniversary: How my Handbag Office was born

This is the story of why my biggest business milestone involved letting go

How offboarding clients, shedding heavy tech, an 18-month detour, and a delayed flight taught me the true weight of freedom - and how a baby blue bag became the foundation for the art of building a lighter life.

On the 1st of May, 2024, I stood in the evening sun on the rooftop above our rental apartment in Florence, wearing a colorful sundress and a sunhat. The magnificent dome of the Duomo was behind me, and the bells of Giotto's Campanile were ringing their 17:30 toll across the city.

I set up my phone and filmed a few short, faceless videos of the view, and of me writing in my brand new pink notebook with the Florentine Lily embossed on the cover. I planned to publish them to the tune of "Dolce Vita" by Ryan Paris.

In the notebook, I wrote, "A new chapter begins... Firenze 1 May 2024," followed by a careful little heart. And then I cheered with a glass of rosé.

A woman's hand holding a pen over a pink journal on a terrace overlooking the Florence skyline at sunset
A wide view of the Duomo in Florence taken from a rooftop terrace during a golden hour sunset
A close-up of a glass of rosé and a pink notebook with a Florentine lily being written in on a rooftop in Florence, Italy, marking a new chapter
A pink notebook and a MacBook laptop on a rooftop in Florence, celebrating a new business milestone

A new chapter once began... Firenze 1 May 2024 💗

It was supposed to be the beginning. I had just made the terrifying, exhilarating decision to start offboarding my web agency clients to make room for my own projects. At the same time, my husband, our daughter, and I had decided to keep the lease on our Florence apartment for another year. The math of decreasing my income while extending my expenses didn't quite make sense on paper. I felt a heavy mix of guilt and wild excitement, but the inner whisper was too loud to ignore.

The 18-month detour and the "Cinderella" phenomenon

And then... the "Cinderella" phenomenon took over.

I did not post the reels. The pink notebook I wrote in got tucked away awaiting a "better day." Instead of stepping into my next chapter, I put everyone else first. A draining, demanding work dynamic with a female narcissist quietly consumed my days, my mornings, my evenings, and my nervous system. The beautiful rooftop videos sat untouched in my phone's camera roll. The dream went on a shelf.

It took 18 months - a year and a half of building other people's dreams while mine gathered dust - before I finally felt free enough to continue what I started that day in May. I wish I had done things differently and put myself first by claiming my mornings and setting boundaries to work on my own projects. But I did not.

Building the foundation: A domain name and a baby blue bag

Then finally, on the 9th of December, 2025, during yet another solo season in Florence, I sat at my laptop, took a deep breath, and did something that took less than three minutes but changed the entire trajectory of my working life.

I bought a domain name.

midlifeinitaly.com.

There are few things in life that compare to the quiet thrill of typing a name into a search box, finding out it is available, and claiming it as your own. It is the digital equivalent of putting a key into a new front door. The room is empty, yes. But it is yours. It was the absolute beginning of my freedom and my peace.

Here is a screen recording of this memorable moment:

A few days later, to celebrate and root this new chapter into reality, I walked down to the Florence leather market. I bought the baby blue handbag I had been quietly dreaming of. It wasn't the most exclusive designer label or the most expensive, but it was perfect for me, and exactly what I could afford on my "listen to your inner whisper" budget.

With the bag on my shoulder, I walked to Café Ditta Artigianale. I ordered a panino and a glass of rosé. Sid, my daughter's Italian Greyhound who had become my constant companion, settled into his own little "bar hang bag" on the chair next to me. I opened my laptop, connected my new domain to a simple landing page, registered the Instagram account, and finally - eighteen months late - posted those videos from the rooftop.

On the video where I wrote in my pink notebook to the toll of the Duomo Campanile in the background, I added the Ryan Paris song La Dolce Vita and the following caption:

"Dream. Create. Celebrate. A New Chapter once began - and now it continues 🥂✨"

I got heavy goosebumps when, after posting, I realized that Ryan actually sang, "This time we got it right".

The day I bought the baby blue handbag and celebrated with Sid at Ditta café 🩵

A delayed flight and the discovery of a proper Italian Prosecco

And here, let's pause. Because you might be wondering: Why rosé? You're in Italy!

Well, because at the age of 56, I had not yet discovered the absolute serenity of a proper Italian Prosecco.

That revelation arrived on the 18th of December, ten days later. Sid and I were at the Florence airport, heading home to Sweden for Christmas. Our flight was heavily delayed and the information was mostly unclear. I went up to the upper bar to get a panino, and the person next to me ordered a beautiful, cold, sparkling golden liquid served in a traditional wine glass.

Because it had so many lovely bubbles, but was served in a regular round glass and not the "flute" for champagne (which I honestly feel is a bit too sour, at least the ones I have tried), I pointed at it and asked the bartender what it was.

She stopped. She gave me a look of profound, deeply Italian, non-arrogant pity and slowly said, "Ma cara... it is Prosecco!"

With no further explanation needed, I said, "Then please pour one for me too".

She nodded and said, "Brava".

I paid her 8.50 euros for it and had one of the most wonderful culinary experiences of my life. That "not too sweet but not too sour" single glass made all the airport confusion - and the typically Italian logistical chaos of being relocated to Pisa by bus due to heavy December fog - entirely enjoyable.

It taught me there can be very nice surprises even in bad events.

My - to my knowledge - first order of a glass of a proper Prosecco at the Florence Airport 🥂 🇮🇹 🛫

A 10-year business milestone: Shedding tech to upgrade life

I am sharing this exact timeline for two reasons.

First, to stake my claim regarding this important milestone in my life. As I write this, I am looking at photos from June 1st, 2016 - the exact day I started my agency, LakeHouse Media. Now we are approaching June 2026 and my 10-year anniversary. In those photos, my desk is covered in the heavy machinery that I then believed a real business required: massive screens, thick binders, colorful pens, a bulky paper calendar for 16/17, an iPad, and endless accessories.

Now, ten years later, to celebrate a decade in business, I am doing the exact opposite of what the industry tells you to do. I am not expanding. I am not taking on more clients. In fact, I have offboarded almost all of them.

I decided to downgrade my physical presence to upgrade my life. I unsubscribed from the expensive, heavy Adobe Pro programs and replaced them with Canva Pro. I left behind the endless WordPress updates of pro plugins, unsubscribed from email automation services, and replaced all of it with one beautifully simple and user-friendly platform: Systeme IO.

However "free" my agency was for the last decade, I did not truly feel free. I was tied to that 27-inch screen and the constant tracking of time for invoicing. I wanted, I needed, to change all that in this new era. I wanted the freedom of fitting my entire business into a baby blue handbag with only my MacBook, a pink notebook, a beautiful pen, and a lipstick as my office setup.

From workstation to Handbag Office - Pernilla Öberg's wooden desk in Florence with large screen, candles and a rooftop view, a laptop on a Florentine rooftop terrace, and her baby blue Italian leather bag at a café

From desk to Italian handbag - my cozy attic office in Florence that evolved into a "Handbag Office" in a baby blue handbag 🩵

The $1 Trillion digital knowledge industry that belongs to midlife women

But mostly, I am sharing my timeline and midlife evolution for the woman reading this who is currently in her own 18-month delay. The woman who has a dream filed under "someday", who is putting everyone else's needs before her own, and who thinks she might be too late or it is too complicated.

You are not too late. But you do need to stop waiting.

We are standing at the edge of a massive economic and cultural shift. The digital knowledge industry - the business of packaging what you know (or what someone else knows) and sharing it online - is projected to reach $1 Trillion by 2028. And the people stepping into this space most successfully are not 20-something tech bros. It is us, the midlife women.

According to recent data from Forbes, women over 50 are now the fastest-growing and most powerful founders in business. A 50-year-old founder is nearly twice as likely to succeed as a 30-year-old. Meanwhile, solo female travel to places like Italy is exploding, with women driving an $118 billion market.

The world is quite literally waiting for our demographic to step up and claim our space. There is a seat for you at the 1 Trillion USD e-learning table. You just have to decide whether you want it or not.

The domain I bought on that December day wasn't just a website address. It was the foundation of an automated digital business that runs in the background while I live my life. The baby blue bag was just the container; the real asset was the decision to upgrade my '90s PC skills and build an income that belongs entirely to me.

If you have a domain name whispering in your head, or a baby blue bag you've been putting off buying until you "earn it"... do not wait 18 months. Do my free "Seven Days to Find Your Next Chapter" and get my free "But How?" Toolbox. Buy the domain. Buy the bag. Order the Prosecco. The door is waiting for your key 🗝️ 🩵 Get it here:

Seven Days to Find Your Next Chapter →

And if you are looking for the practical tools - the structure, the strategy, and the free guide to the one trillion dollar knowledge economy - it is all in the Digital Renaissance Blueprint:

Download the Blueprint →


A walk down memory lane - the beginning of LakeHouse Media in June 2016

The LakeHouse Media web agency office setup in 2016, featuring a large iMac screen, heavy binders, paper calendars, and complicated tech equipment.
iPhone 6 in 2016. The LakeHouse Media web agency office setup in 2016, featuring a large iMac screen, heavy binders, paper calendars, and complicated tech equipment.
An iPad in 2016. The LakeHouse Media web agency office setup in 2016, featuring a large iMac screen, heavy binders, paper calendars, and complicated tech equipment.
The LakeHouse Media web agency office setup in 2016, featuring a large iMac screen, heavy binders, paper calendars, and complicated tech equipment.

Setting up my new office in 2016 - a new 27-inch iMac, an iPad, an iPhone 6, tons of tech accessories, binders, pens and a thick paper calendar for 16/17 🖥️📚📱✏️

The LakeHouse Media web agency office setup in 2016, featuring a large iMac screen, heavy binders, paper calendars, and complicated tech equipment.
The LakeHouse Media web agency office setup in 2016, featuring a large iMac screen, heavy binders, paper calendars, and complicated tech equipment.
The LakeHouse Media web agency office setup in 2016, featuring a large iMac screen, heavy binders, paper calendars, and complicated tech equipment.
The big office printer. The LakeHouse Media web agency office setup in 2016, featuring a large iMac screen, heavy binders, paper calendars, and complicated tech equipment.
The cabin AirLink wifi set-up
The cabin AirLink wifi set-up

The LakeHouse Media office in 2016 - the outback agency that became reality thanks to an AirLink wifi 10 km away from our cabin 📡


The LakeHouse Media lake office, a MacBook, a thermos and a wooden coffee cup with a lake view
Pernilla Öberg sitting with her MacBook by a calm lake in the Swedish arctic mountains of Vallrun
Pernilla Öberg by the lake in the Swedish arctic mountains

Pernilla Öberg, LakeHouse Media by the lake in Vallrun. My other favorite workplace - the Swedish arctic mountains 💚💙


About me

Pernilla Öberg - writer and creator of Midlife in Italy, photographed a cold winter's day in Vallrun, Sweden

I'm Pernilla - a happily married empty nester sharing my solo seasons in Florence, slowly and honestly. This is where the stories live - the cafés, the walks, the work, and the quiet process of finding the next chapter. The everyday texture of solo seasons in Florence, the honest process of building something new in midlife, and the quiet tools that are making it possible. Browse by category, or begin with the Seven Days email series if you feel ready to explore your own next chapter.

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