Ask Yourself Tough Questions And Let The Answers Change You

[This was first published on the minimalism and lifestyle blog No Sidebar.]

My wife and I sold or gave away 98 percent of our belongings which enabled us to achieve our goal to become full-time nomadic travelers in July 2023. In my pursuit of a simpler life with fewer things, I had to ask myself tough questions. I needed to––I was a self-described “collector of collections” and had a lot of stuff when I started this journey.

Asking myself the popular question about whether something sparked joy didn’t work for me. I found it too easy to confuse any “joy” I felt for a possession with the fleeting enjoyment of a shiny new object––that proverbial “new car smell.” Sometimes I needed to get rid of something even if I really liked it. On the other hand, important possessions I used everyday didn’t spark joy and they didn’t need to. They just needed to do their jobs.

Instead, I found that I needed to ask myself different questions depending on the item in my hands. Six tough questions helped me identify what I wanted to change in myself in relation to what I owned. When I took the time to reach my answer, I changed my relationship with each item, freeing myself to make clear-minded decisions whether to keep or let go.

1. Do my emotions connected to this item exist only because I possess it?

Many of my possessions had sentimental value. For example, love letters from dating my wife 37 years ago, awards I received during my military career, keepsakes given to me from relatives, and a lifetime of collectibles all carried emotional weight. But I found that the feelings were independent of the items––they existed in me. I could feel the achievement of my military career without keeping the physical awards and the nostalgia for dating my wife without all the letters. I found taking a few quality photos helped me detach the emotions from the physical items.

Photo reminder of some hard-to-get coins awarded to me during my military career

2. Do my family and friends really care if I let go of this thing they gave me?

When my wife and I were first married, her parents gave us the family’s upright piano, the one her great-grandmother danced around in delight when her great-grandfather brought it home in the 1930s. As a military family, we moved that 600-pound piece of musical furniture to 14 different houses. It didn’t fit in our lives, but it had the weight of family expectations––we were the keepers of a family heirloom. When we finally gave it away, we didn’t give away our memory of and love for her great-grandmother, and we didn’t lose the love of our family. I discovered that my family and friends weren’t nearly as disappointed (usually not at all) as I believed they would be when I let go of something they had given me. My guilt was self-imposed.

3. If I let go of these excess clothes, do I care if people see me wear the same clothes on a frequent basis?

Subconsciously, I used to care a lot. I let marketing companies and the middle-school fashionistas of my past impact my adult behavior. Once I realized that it was really me enforcing their rules on what I should wear, I freed myself to wear what I wanted––a few functional, durable clothes. My colors are mostly gray (my daughter lovingly calls it my “groutfit”) and I’m sure I look the same in every photo, but my clothes now reflect my values and take up a lot less space.

Wearing my “groutfit” as I travel (Prambanan Temple, Indonesia)

4. Is this possession an investment or an expense?

I held the notion that many of the items I collected over the years were investments and would be worth a lot of money someday. I felt that I had to keep them until I got my perceived value for them. As I downsized, I learned in most cases my possessions were not worth what I thought they were, both in dollars and in my effort to get that money. My stamp collection (couldn’t find a buyer), coin collection (sold most for melt value), Seinfeld DVD set (garage sale price), electric guitar (sold at 40% of retail), autographed Wedgewood vase (gave to charity), Irish Belleek china (garage sale), and more were not worth even close to what was paid for them, and it would take a lot of my valuable time to get more than dimes on the dollar.

5. Can I borrow or rent this item instead of owning it?

I enjoyed collecting a fairly large bookshelf full of books, but came to realize that there are very few books––physical, digital, or audio––that I can’t get from my excellent local public library. When I need them, I can rent tools, a bicycle, a car, and a suit. And if I ever miss the sight of my old collectibles (I haven’t yet), I can visit stamp or coin shops, antique stores, and museums any time and see more wonderful collections than I ever had.

6. How do I handle new items that come to my doorstep?

Once I used the five questions above to let go of all my excess possessions, there was one more important question I needed to maintain my newfound freedom: how do I keep new stuff out? Do I add them to my inventory of items to manage? Having dealt with decades of the “collect-purge-collect-purge” cycle, sustainable change began when I stopped collecting in the first place. I stopped shopping. Oh, I still buy an item like a shirt or shoes when I really need it, but shopping as entertainment is no longer part of my life. I politely let relatives and friends know I value experiences (eating out, visiting a museum, and travel) and consumables (homemade cookies or a bottle of craft gin) over physical possessions. For gifts that I can’t dissuade someone from giving, I find a new home for it and don’t let it become a part of my life.

The answers to my 6 tough questions changed my relationship with the things I owned and was the start of a newfound freedom. I encourage someone starting this journey to find the questions that work best for you. Asking yourself tough questions to identify the underlying internal and external forces behind why you have what you have will help you hone your values and discard items that are not in alignment with those values.

This is a sister post to my post “The Metamorphosis to Becoming A Minimalist


The Metamorphosis to Becoming a Minimalist

My wife and I sold or gave away 98 percent of our belongings. Our dream to be full-time nomadic travelers took flight in July 2023––a goal we never thought possible until we fully embraced minimalism. 

In her popular book The Life-Changing Magic of Tidying Up: The Japanese Art of Decluttering and Organizing Marie Kondo is adamant that a successful minimalist life only can be achieved if a person does the decluttering all at once and not a little at a time. My experience was the opposite. 

My metamorphosis from a self-described “collector of collections” to a minimalist took over three years to achieve through several stages. Small incremental reductions of what I owned, in turn, resulted in small but noticeable increases of freedom and control in my life. In fact, it changed who I was. While a caterpillar physically changes, I evolved internally, honing my values and perspectives.

Lucky Lager puzzle bottle caps from the late ’70s — one of my many collections

Like a caterpillar becoming a butterfly, I progressed through four stages to become a minimalist.  

Each stage  motivated me to make further (and often bigger) reductions in possessions and commitments resulting in increased white space and contentment in my life. A virtuous cycle. 

Egg Stage: Start small, but discard enough to notice (and then notice!). 

I started with the low-hanging fruit––I culled my closet, shoes, and some books. I disposed of enough to notice the freed up space. My drawers closed easier, my hangers had elbow room, and my shelves could breathe a little. It felt great and a little freeing to take a car load of boxes and bags to the nearby donation center. 

Noticing how great this felt, I was motivated to do more. I went after our basement and attic storage areas––they were full of large plastic bins and boxes neatly stacked on shelves or in rows (reflecting years of storage management efforts). Again, I didn’t do it all at once, but I culled enough so that the empty boxes, bins, and shelf space after each round would continue to motivate me. 

Decluttering enough to notice — I had spent decades buying bins and shelves to hold more stuff

In this “egg” stage, I passed over the vast majority of my possessions because they either had sentimental value (awards and keepsakes), emotional value (gifts and family heirlooms), functional value (tools, supplies, clothes), perceived rarity (collectibles), or perceived monetary value. At the end of this stage, my past self would have stopped––some culling and a car load or two of donations, creating some temporary space until the clutter returned. But this time I used the momentum from this stage as the start of true change.   

Larvae Stage: Devour knowledge about minimalism and keep iterating.

Before I could tackle the “harder” possessions, I needed to learn more about the benefits of minimalism and gain tried-and-true techniques that worked for me. I read several books and blogs, listened to podcasts, and watched YouTube videos taking in many different perspectives on achieving a better life through minimalism. 

There are many different approaches to minimalism. While I gleaned some valuable ideas from most of them, Fumio Sasaki’s book Goodbye, Things: The New Japanese Minimalism resonated most with me. This book provides specific techniques for minimizing every type of possession. While I found he went a bit further than I did in my downsizing, I appreciated his thorough approach to the subject.

Finding the right voices that teach and inspire you is an important step in advancing your minimalism skills. I felt stronger knowing there is a supportive community and that I wasn’t alone in wanting the benefits of owning far fewer possessions than most citizens of developed countries.

As I learned new techniques and challenged my mindset, I iteratively returned to my closets, drawers, shelves, and storage with a fresh perspective and continued to make progress.

Pupa Stage: Ask yourself tough questions and let the answers change you.

As I advanced in my pursuit of a simpler life with fewer things, I needed to ask myself tough questions about who I was, what was important to me, how I let external pressures drive my internal decisions, and what were my expectations of the things I owned. 

Asking myself Marie Kondo’s famous question about whether something sparked joy didn’t work for me. I found it too easy to confuse any “joy” I felt for a possession with the fleeting enjoyment of a shiny new object––that proverbial “new car smell.” Sometimes I needed to get rid of something even if I really liked it. On the other hand, important possessions I used everyday didn’t spark joy and they didn’t need to. They just needed to do their jobs. 

Instead, I found that I needed to ask myself different questions depending on the item in my hands. The six tough questions below helped me identify what I wanted to change in myself in relation to what I owned. 

  • Do my emotions connected to this item exist only because I possess it?
  • Do my family and friends really care if I let go of this thing they gave me?
  • If I let go of these excess clothes, do I care if people see me wear the same clothes on a frequent basis?
  • Is this possession an investment or an expense?
  • Can I borrow or rent this item instead of owning it? 
  • How do I handle new items that come to my doorstep?
This photo is all I need to relive the joy of meeting
Warren Miller and watching his ski movies as he narrated them

These questions exposed my underlying beliefs, emotions, and societal pressures I attached (often subconsciously) to my possessions and impeded my ability to let them go. The answers to my 6 tough questions helped me change my relationship with the things I owned, freeing myself to make clear-minded decisions whether to keep or let go, and was the start of a newfound freedom. 

I examine these six questions in more detail in this sister post.

I encourage someone on this journey to find the questions that work best for you. Asking yourself tough questions about your possessions to identify the underlying internal and external forces behind why you have what you have will help you hone your values and discard items that are not in alignment with those values.

Adult Stage: Ready to fly 

I became a minimalist long before I pared down to the amount that I needed to meet my nomadic travel goal. My mindset and values completed their metamorphosis about 8 months before my belongings and commitments reflected that change. 

Getting rid of a lifetime of possessions in a responsible way (selling, recycling, re-homing, donating, etc.) takes a lot of time. 

The upper side of our major “everything-must-go” yard sale

For example, my wife and I culled, scanned, and then disposed of all physical photos except our small wedding album. It took days of hard work, but we are now enjoying the fruits of this labor by having immediate searchable access to over 7,000 photos. We enjoy and share these old photos far more than we ever did when they were stored in albums and boxes in the basement. 

The lower side of our major “everything-must-go” yard sale

It was at this stage where I was able to tackle the hardest downsizing as I had the mental tools and fully understood my values in regards to my possessions. The emotional, sentimental, societal, and other belief barriers were no longer preventing me from taking action. Scanning in our hard copy photos ourselves and taking nicely laid out photos of keepsakes, awards, our kids school artwork, and other emotional and sentimental items (e.g., my bottle cap collection and autographed Warren Miller program) helped ensure I retained a record of the memories that these items represent and why I was keeping them. Looking at these and our other photos helps me reap a bigger memory dividend––the best return on investment we can achieve in life. 

My wife and I completed our downsizing in July 2023, and now we travel the world full-time with a backpack and a carry-on each. My wife Launa shares poignant observations from our travels on her blog at Launa At Large where you can sign up for her thought-provoking electronic postcards. We love our freedom and the calming white space that minimalism has brought to our lives. 

Ready for full-time travel with a carry-on and a backpack

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