A Quest to Reconnect with Positive People in our Past


“The pain of parting is nothing to the joy of meeting again.”

Charles Dickens

So much of life is a series of connections and relationships with other people. Some of those connections persist to today, while others come and go. Either way, each person with whom we interact is a part of our life story, as we are part of theirs. Even the most solitary and self-sufficient people among us are indebted to dozens, hundreds, even thousands of people over the course of their lives.

How much do you think about the people from your past? Every so often, we find ourselves reconnecting with past friends, colleagues, classmates, and distant family members. Maybe we encounter them in the airport, while out at a restaurant, at a conference, or some unexpected place.

Perhaps more common, we connect amid some of those milestone moments in life. We attend a wedding of a longtime friend, go to a high school reunion, our find ourselves at a funeral; seeing people whom we’ve not thought about for years, even decades.

“When the roots are deep there is no reason to fear the wind.”

African Proverb

In such moments, we might experience any number of thoughts and emotions. Maybe the awkwardness of the situation prompts us to hide or avoid the person, perhaps pretending like we don’t recognize them. Or, maybe we are drawn to such moments, and we are quick to take initiative to greet them with a few words or even a hug. Such chance re-connections can be moments of joy, anxiety, curiosity, or maybe even fear. Regardless, they draw us back into our past. Even a brief encounter can be enough to prompt hours or days of remembering and reliving, even learning about ourselves, where we’ve come from, where we are now, and where we hope to be in the future.

“I am a part of all that I have met.”

Lord Tennyson 

Whether you are an extrovert who is energized by time around others, or you are an introvert who requires personal time for that same energy; all people crave and benefit from rich, meaningful human connections. We are designed that way, and even though we might initially dread the work or anxiety associated with meeting a new person or connecting with someone from our past, this effort attaches us to a deep, ancient, persistent human need and craving.

This life experiment is one of several opportunities to experience and explore this reality for yourself. It is not easy, and the outcome is uncertain, but it taps into any number of our most fundamental yearnings. It offers a sense of adventure and mystery, provides the possibility for new forms of gratitude, and most fundamentally, gives us a mirror for our own growth, and allows us a chance to feed that yearning for human connection.

  1. This is a 4-week experiment.
  2. The first week of this quest is one of reflecting and remembering. Make a list of at least 20 people from your past that you have not seen or spoken to for at least 5 years. Depending upon your age, maybe you want to make that at least 10, 15, or 20 years in your past. You decide. Choose people who bring up fond memories for this experiment, but don’t just rely on your memory. Check with friends and family members. Look at old yearbooks or photos. Browse your emails and work-related projects that might be siting on your computer. As you make your list, use this as a chance to reminisce. Enjoy it.
  3. If week one was about remembering and reminiscing, then week two is your research and planning week. Choose at least four of the people from your list, and find out where they are today. This quest calls for you to reconnect with at least four people from your initial list, one in each of the following ways. You don’t have to do all of the following during week two. Your only task this week is to do the preparation. That means finding contact information, choosing the people, etc.
    • Choose and plan for one person whom you can reach out to via an email, simply explaining that their name came up for you recently, and that you wondered how they were doing. Sharing something for which you are grateful is always a good thing to include as well. You can share a bit about yourself as well, but if things are going particularly well for you, be cautious about what might seem like boasting.
    • Choose and plan for a second person. For this one, you will do the same thing, but send the message the old fashioned way, with a card or handwritten letter.
    • Now identify and plan for connecting with a third person. Only for this one, you have the challenge of making a phone call.
    • Finally, for the fourth, you are going plan for reaching out to the person and inviting that person to join you for coffee or lunch, just to connect.
  4. Now, for weeks three and four, you have the quest of following through on each on your plans. Reach out. If one doesn’t work, go back to your list and choose someone else.


  • Don’t worry if some of these do not work out. That is why you are starting with a list of twenty people.
  • This experiment can bring about a myriad of emotions. It is great to have a friend or family member so that you can talk through and debrief the experiences.
  • Try to avoid the trap of comparisons. This is not about finding out whose life is the best. It is about connecting with people who were a valued part of your life story. Instead, focus on gratitude, catching up about each other’s lives, re-connecting, listening, and learning.
  • While you might be tempted to use this experiment to mend broken relationships, and that is certainly your choice, this experiment is designed to connect around positive people and memories in your past. So, if you are craving to do reconcile, consider leaving the mending of broken relationships for some future time, maybe even a future quest one of your own design.
  • As with all life experiments, I can’t emphasize enough the value of reflection and journaling. What did you learn about yourself? What did you find yourself thinking and feeling? Might one of these connections turn into a rekindled friendship?
  • These are positive people from your past, but don’t forget about safety. Be wise and thoughtful about what you share and how you connect, just as you do with new friendships. It takes time to build trust, and that applies to people from our past as well.
  • In an age of social media, it can be easy to “spy” on people from our past, but not actually reconnect with them. This is a quest to go beyond that. Actually reach out.

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