Years ago, after both of my grandparents passed away, I opened up a storage unit in San Francisco to store some things of theirs (plus a few of my own). All relics from a past life that I thought I’d want with me in a future life I didn’t yet have a glimpse of.

Years later, as I got ready to move across the country to Georgia, I went through that storage unit. At $40 a month, I shudder to think that I’d spent almost $2000 to keep things like boxes of old New Yorker magazines and a mattress that I could have bought many times over with the money I wasted to hang on to it.

I do respect that mistake as an early-life lesson in decluttering and letting go : You should keep some treasured symbolic mementos of loved ones, but don’t feel pressure to hang on to every memory at the expense of your current self. Yet I know things aren’t so clear cut. For instance, it was certainly not practical to keep my grandparents’ custom-made dining table and haul it across the country, but I love having it today and haven’t once regretted keeping and storing it.

Nevertheless, going through that storage unit was a turning point for me. It was the beginning of my quest to learn to let go of things easily. Personally, I don’t want the things I own to bog me down, siphon away my time, or obscure the truly meaningful things in a deluge of other items (kept only out of fear of going without them).

It’s a journey I’m still on: practicing letting go without regret—and knowing what to keep without regret, as well. It’s a two-way street, and I don’t always get it right. I’d always held the belief that my home is “not a storage unit” and used that mantra to confidently get rid of things, knowing they could be bought or borrowed again, should the need arise. But the pandemic has led me to re-think that too-cavalier thought—and re-think all the ways I decide what to hang on to and what to declutter.

At this point in time, with both typical life milestones as well as a centennial pandemic perspective thrown into the mix (I can’t help but think my grandparents must have been through this, too), here are the questions I’m going to start asking myself when I’m wondering whether I’ll regret getting rid of something:

Does this item serve more than one purpose or person?

“Infinitely useful” sounds dramatic, but many craft and art supplies are. Watercolors, water color paper, puzzles, pipe cleaners, googly eyes, brushes, spray bottles, tissue paper—having many of these used to feel too cumbersome to keep sorted and to store. But facing weeks that turned into months of five young children at home and being mostly unable to run out to the store for craft items to help keep them busy and happy, I have added these things and more to my list of art supplies to keep on hand if I already have them. I won’t be getting rid of anything like this in the near future, that’s for sure.

I’d also include activity books like workbooks, sticker books, and activity books. They’re easy to store, can be used by multiple children and passed down as they grow, and become “new” again if they’re stored in the closet for a while.

The question of whether or not something is useful for more than on purpose or person helps decide what hobby supplies to donate and what to keep, too. Personally, I discovered that if I lose interest in a particular project (like the cross-stitch of draft horses I started when I worked at a swimming pool locker room as a teen), I’m unlikely to pick it up again and it’s okay to get rid of it. Generic supplies, on the other hand, like quarter-inch elastic, which became impossible to find for several weeks during the dramatic surge of homemade mask-making, should be kept for future use.

Is this something that will become more meaningful with time?

This is a tricky question because the longer you hang on to something, the more importance it seems to obtain. But this isn’t what I mean; don’t keep the fondue set you’ve never used just because you’ve already kept it for a decade.

However, consider whether a certain thing might become more meaningful as you age or as your children grow older. For instance, I really, really regret getting rid of my elementary and high school yearbooks. I get so sad that I don’t have them anymore to look back on as my children pass through the same milestones and I miss being able to show them school pictures of Mommy in the grades they find themselves in now.

Will this item be useful as I go in and out of life “seasons”?

There’s a difference between items that you shed because they’re no longer useful or joy-giving and items that you don’t need right now but might need again someday. Again, this feels like a slippery slope because if you kept everything that might be useful again someday, you could end up keeping everything.

What I mean here is generic useful items. A curtain rod with finials that matched the lamp you no longer use, in the house you no longer inhabit, does not fit this bill. But office supplies like neutral-colored magazine holders, drawer organizers that aren’t currently in use, and baskets and other containers are very likely to come back into rotation as your life unfolds. Having them on-hand when you need them saves so much money and time.

For instance, when our family’s life and activities became completely house-based, I regretted getting rid of my storage bin full of baskets. They were so easy to store because of how readily they nest, and I would have really liked being able to grab something from my stash to corral the stuff of all the people in my house who were suddenly home all the time. Getting rid of baskets is a mistake I won’t make again.

By asking these three decision-helping decluttering questions—whether something is useful for more than person or purpose, whether it will become more precious with time, and whether it’s a generically useful item—you can help reduce the regret that sometimes follows lightening the load of your possessions.