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What 3 Weeks Organizing My Photos Taught Me About Downsizing

Are you downsizing? Did you struggle with some of your favorite possessions? Have you thought about downsizing your photos?

Our Downsizing Challenge

Organizing Photos Downsizing

60+ years of photos were stored in 5 large plastic storage containers that needed two people to lift them. Some were in photo frames; some in photo albums and some were loosely thrown into the containers.

The challenge was to reduce 5 heavy containers down to 2 easily manageable ones.

Back in 2011, we sold our large 5-bedroom family home and moved into a small 2-bedroom apartment by the beach in the Northern Beaches of Sydney, Australia.

That turned out to be a major downsizing challenge. I’m sure that many of you have experienced that and know what that feels like. The emotions, the garage sales and the online ads took over our lives for the next few weeks.

Our nomadic life began in 2013 and, once more, we needed to downsize our possessions, which ended up filling up one of our son’s garages.

Would we ever return to live a normal life again with possessions?

In 2014, we returned for a few months and the plan was to reduce our possessions even more to 10 plastic storage containers.

We opened the garage door and instantly felt overwhelmed as we struggled with the emotions of the task at hand. We quickly closed the garage door and headed off to the nearest pub wondering what the hell we were going to do.

Six very long weeks later, we had reduced our possessions to 10 plastic storage containers, 1 suitcase and 4 paintings and a man box of “bits and pieces” that needed to be kept “just in case.” Our “storage life” then journeyed to a friend’s shed for a few months and then found a home back in our other son’s garage.

So back to our photo challenge… we thought we had a plan!

Our 5-Step Photo Downsizing Plan

Step 1: Review all photos (10,000+ estimation), and remove from the current photo albums and frames.

Step 2: Discard those of poor quality (there were many of these and we guess we kept them because we had paid for them in the many rolls of film that we took….long live digital cameras, that is all I can say!)

Step 3: Create two piles 1) photos that are to be kept 2) exceptional photos that were to be rephotographed and saved to three external hard drives – one for us and one each for our boys.

Step 4: Place photos in acid free bags in date and event order.

Step 5: Store in two plastic containers.

Sounds simple, right?

Where to Start

Do not start where we started! It will end in disaster and confusion. We (sorry, I mean “I”) opened the first box, dived into the memories and sat fixated for the next few hours pulling all the photos out of the albums in no order at all. I felt relieved that I had just saved these photos from the cheap plastic photo albums that had housed these memories for so long.

Organizing Photos Downsizing

In this euphoric state of mind, I sat with hundreds of photos surrounding me until I realised that we (once again, I) needed to put them in some sort of date order.

With the empty photo albums now completely destroyed, any chance of dating our precious photos had now gone up in smoke.

We struggled to get our next four containers into date order. There were individual photos from our respective childhoods, ancestral family photos, wedding, babies and our boys sporting achievements and holiday photos.

Organizing Photos Downsizing

Looking back, I should have been more diligent on writing on the back of photos the dates and events.

A task that should have taken a week turned into three weeks. Each afternoon, we had to wait for the right light to rephotograph the photos. We had to tread carefully around the piles of photographs spread out on our living room floor, most of them now dated and some even with the event shown.

One pile still sat in the corner, obviously being ignored by both of us. We just did not know what to do with them.

Over the years, friends and relatives sent us many photos of their children and important dates in their lives. We had lived abroad and we had missed many of their events. Some we thought we could recognise and some we could not – we are not big fans of “miscellaneous” files but in this case we could not avoid it.

Three weeks later our photographic memories were now stored neatly into two containers, in acid free packaging that will prolong their life, and three external hard drives of our family’s history.

Friends are now coming to us to sort their family memories out. It could be a new business for us, but the answer is no. After all, we are nomads and we are travelling the world. We are having adventures and taking more photographs!

Let’s Have a Conversation:

Could you downsize your photographic memories? Which photos are most special to you and why? How many photos do you think you have in boxes and old albums? Please join the conversation.

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When we downsized I threw 40 years of travel photos away.
Each trip was in a separate album and dated but after many years of our children and grandchildren viewing these photos, no one was interested. Great memories but took up heaps of space that we didn’t have in our new apartment


Did you take photos of your photos of your favourite travel moments and put them on a hard drive?

Frances Siejkowski

I have been sorting our huge collection of photos for several years now. I have placed many into albums and made digital files from many others. There are photo boxes and albums organized by date and I have gifted our four children albums of their own with their baby pictures, school photos, birthday, graduation and wedding photos. It’s been a labor of love and I hope to finish it soon.


It really is a labour of love. Our boys have portable hard disks with our best photos of their younger lives on it for them. Now they have their own children they are loving looking back at the memories and comparing themselves to their boys


The timing of this article is mind-blowing, as I’m just finishing up this very project today. I didn’t put dates on my photos either, so the best I can do is organize by decade. I feel like I just re-lived my life. It’s bittersweet – so many great memories, but so many loved ones are gone. It was highly emotional. Nothing like holding on to physical photos – I’m not one to digitize them.


It is bittersweet but also enlightening. I was speaking to a friend about it yesterday and she laughed as she had all these photos with people in it she couldn’t remember who they were or where they were taken. She felt better going through them.


I did the same a couple years ago, tho my photo stash was smaller than yours. I made pockets by taping 2 sheets of junk mail together on three sides. Did a quick initial sort and then went back thru each pocket. Ruthlessly culled at each step. After, a friend with computer skills & scanning equipment helped. He saved each pocket separately both to Google photos and to a thumb drive. My arrangement is not strictly chronological, but by topic: My Childhood, My Son’s Childhood, First Marriage, Homes, Pets, Trips, etc. Ancestors are grouped with each surname in a separate file. It worked well and I can quickly find anything I want. I paid my friend with lunch out and a pound of his favorite cheese. The physical photos we shredded, except for the dearest which I keep in a tin 5 × 7 x 3 inches.


Loved the idea of placing them in topics! Thats a great tip

Michele Yellin

What happened to the photos not in the 2 containers? That’s my biggest question. We have scanned many photos, but what about the physical copies? Shred, or just trash. It is an emotional process but necessary.
thanks for sharing your journey.


Hi Michele, we trashed them! Definitely felt emotional doing that but well worth it in the end.

The Author

Jane and Duncan Dempster-Smith are nomadic semi-retirees, baby boomers, travellers, House Sitters and co-founders of To Travel Too Their motto is “Age is no barrier when it comes to travel.” Although not yet pensioners, their goal is to travel the world on what is currently the Australian Age Pension of approx. AUD 33,716 (USD 25,110) per year, or AUD 92 (USD 69) per day for two people.

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