Week 9 of the Clever Girl Organizing Challenge: People in Our Lives

It’s Week 9 of the Clever Girl Organizing Challenge, and so we begin the second half of this 16-week adventure to help you reclaim your homes and lives back. 

If you’re following along with The Challenge in real-time, you know that today is February 29th: Leap Day! Leap Day is special and rare, so, I wanted to give this week’s attention to something else that’s special and rare: our relationships with the people in our lives, today and in the past. 

To be clear, I’m not saying that this week is about decluttering relationships out of your life… even if that sound like a good idea to you at times! 🙂   What I want is to draw your attention to a few things, and see if there are any of these that sound like something you could do.  So, of our two levels this week, one is about taking positive action to reinforce our relationships and the other is about decluttering some of the ways in which people and our connections can get in our way. Because, make no mistake:  The way in which we live our lives and connect with people can absolutely support our peace and happiness, or can be a source of stress, anxiety, and regret. 


16 challenge

Week 9:  People In Our Lives

Level 1 Challenge: Make Connections Stronger. This one is about taking some time to think about the people in your lives who important to you, and making sure they know it.   Consider this list (and come up with your own) of actions you could take this week: 

  • Write (and send) a letter – There are people in your life with whom you have lost touch – old friends, family, former colleagues, etc. Or there have been people who have brought meaning to your life, and you feel you haven’t sufficiently thanked them for what they’ve done to make your life what it is today. Maybe go through the lists you tend to keep (the holiday card list, your contacts, old address books, even Facebook friends) to find a name or two of people to whom you could sit and write a note to let them know you’re thinking of them, or thank them for what they’ve meant to you.  Could you even imagine how amazing that person’s day will be when a heart-felt letter shows up in the mail from you?  Wouldn’t you be blown away to receive one? Why shouldn’t the people who matter to you feel that good? 
  • Phone a friend – Think about the friendships that have evolved (devolved?) a bit to being primarily text-based at this point. You went from talking all the time to emailing and now you’re just texting or DM (direct message) or PM (private message).  Life’s so busy and you’ve managed to stay connected with a sentence here and an emoji there.  What if you reached out and called that person?  Sure, maybe you need to schedule it, and it feels less spontaneous, but what about just saying, “Hey, it’s been a while since we just talked. I miss your voice! Got some time in the next week to chat?”
  • Give Someone Your Time – We all know that time is the one currency we just can’t make more of… and how important it can be not to waste. Think about someone in your life who could use a little more time, a little more patience, a little more… well, a little more YOU. Maybe it’s someone you know, and maybe it’s even a stranger who could benefit from having you in his or her life for a moment, through volunteer or charity work.  
  • Write Down Your Story –   I’ve worked with a couple of clients who are looking at downsizing and struggling with their memories attached to the things in their home. We talk about the concept of stories, and how to preserve them, for the people who want to know them in the future. This isn’t just for Baby Boomers; this is an exercise that anyone can engage in to help others remember what memories were important: How you met your significant other, your favorite memory as a child, your biggest regrets, your greatest accomplishments, your biggest life lessons, and so on…. Could you take time to write down your story, and know that someday, someone will be grateful you took the time to write it down? 


Level 2 Challenge: Decluttering connections. This one is about eliminating a few things. Not people, per se, but editing down some of the parts of connecting with others that may feel “in the way” or negative. 

How to tackle this one:  The first is very tactical, the second is tactical-but-not-without-some-thought-on-the-matter, and the third is a big and heavy one. 

  • Clean Out Your Contacts – Honestly, keeping your contacts and address book cleared of clutter is just as useful a task as a lot of other organizing.  Sometimes it’s just as simple as making sure you don’t have to scroll through lots of useless contacts to get to what you’re looking for.  Sometimes, it can be just about eliminating the possibility of an embarrassing butt-dial or email hack. Take some time to go through and determine “Does this person really need to be in my at-my-fingertips directory?”   If not, consider deleting a name or two.  
  • Clean out your Facebook Friends (or wherever else you collect online connections) – Our Facebook and other social media accounts can get cluttered just as easily as any other part of our lives.  And, when you are regularly exposed to things that annoy you in your newsfeed (yes, Leap Year also means Presidential Election Year) it can really make your perusal of your Facebook world somewhat aggravating, can’t it?  What if you took some time to review your friends list to determine if you’re really getting something out of having that person in your virtual life, and consider unfriending (or “unfollowing”, which means you’re still “friends”, but their updates no longer show up in your newsfeed anymore)? What if you could make this activity more pleasant for yourself with just a few clicks? 
  • Forgive Someone – Maybe you’ve been holding on to a grudge for a while. Maybe it’s been so long that you don’t even remember what it was about. Or it’s about a friendship that just had too much time pass, and you’re embarrassed. You were mad at the time, and the anger has passed, but the relationship got away from you in the process; you spent more energy being upset than the original transgression may have warranted in the end. If you’re thinking about it now, and it’s still causing some negative feelings, perhaps you might consider whether forgiving this person brings some relief to your life. 




How The Challenge Works:
As With Every Week, Your mission:

1) Take on Level 1, and if you’re feeling up to the challenge, Level 2. If you’ve already got those covered, identify a challenge for yourself that you know you should be tackling.

2) Whenever possible, take BEFORE and AFTER pictures. You don’t have to share them with anyone but yourself, but it is a fantastic way to (a) identify clutter that’s become invisible to you over time and (b) truly measure and appreciate your progress. 

3) We’re all about letting things go…  be critical about what you’re keeping and why you’re keeping it.  Always ask yourself these critical questions to help decide if you should hold onto items: 

  • Is using this item part of my current life or likely future?
  • If I didn’t have this item and needed it for some reason, is it easily replaced or borrowed?
  • Can someone else use this more than I seem to be using it now? 
  • Am I keeping it for a “maybe some day” or a “just in case” option? How likely is that situation? And am I keeping more in that category than I should, given the space constraints I have?
  • Is it part of my past, and holding onto it reminds me of a former self? And am I keeping more in that category than I should, given the space constraints I have?

4) Stay FOCUSED on this task.  Know what FINISHED looks like, and don’t get distracted by other projects or areas of attention that cross your path while you’re on this assignment.  

5) Have a plan on where things will go — give away to someone you know, donate, sell, recycle or trash.  This Challenge isn’t just about creating new piles that don’t have a future!

6) Work in manageable chunks of time and energy. It’s a marathon, not a sprint! 

7) Celebrate and reward yourself for a job well done!




  1. Janet Barclay

    A very good friend of mine passed away on December 30, and I’ve realized that if he hadn’t been persistent in staying in touch (he actually called me the day before), it would have been a very long time since we connected (other than on Facebook). That was a huge reminder not to take important relationships for granted.

    • clevergirlorg

      Janet, Thank you for sharing your experience and thoughts. I’m sorry for your loss, and glad that you’ve taken from it a life lesson as you move forward. I appreciate your reminder for us all!


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