At The Crossroads: A Self-Guided Spiritual Retreat For People Turning 40

At The Crossroads: A Self-Guided Spiritual Retreat For People Turning 40

For my fortieth birthday, Jasmine gave me a gift that any introverted, middle-aged priest would appreciate: a private, 48 hour spiritual retreat at a nearby Cistercian-Trappist Monastery— specifically, our Lady of Calvary Abbey in Rogersville, New Brunswick.  It’s a special place for both of us— a place whose very atmosphere itself has been worn thin by the perpetual prayer of generations of monks, thereby making the partition between this life and the eternal seem somehow delicate and ephemeral. It is a place where, for me at least, communing with God seems as effortless as breathing. While there, I wanted to make the most of my time. So, I put together a self-guided retreat program that would allow me to take serious stock of my life— past, present and future.  

It’s possible that this program may be of some use to others.  In fact, it’s with this hope that I offer it to anyone interested. Perhaps you too have a birthday with a zero in it and, for this reason, feel the need to seriously reflect on your life. Or, perhaps you’ve reached a major milestone— the birth of a child, the loss of a loved-one, a change in career, the beginning/end of a marriage— and you feel the need to put the whole of your life into perspective. If that’s the case, then what I offer you here may be of some use.  

Preliminary Comments

The entire program is based around 4 sessions. The first two sessions involve answering a series of questions regarding the past. The last two sessions, questions about the future. You can respond to the questions in several ways. For example, you can write them out in a journal or dictate them audibly on a recording devise. 

It took me roughly three to four hours to get through each session with breaks in-between to eat meals, go for walks, pray, read, etc. I could not have done this self-guided retreat at home with texts and e-mails coming in, my children running around and the constant temptation to watch TV or engage in social media. Therefore, I would highly recommend going to a retreat centre or monastery. Don’t bring a tablet or laptop unless you possess the self-discipline to shut off the wifi and keep it off.


Session 1: Learning from the Past and Experiencing Forgiveness

Spend twenty to thirty minutes in prayer and/or meditation. 

Prayerfully read Psalm 139

Ask yourself the following questions. 

  • What do I regret most in my life? What do I wish I had done instead? Have I forgiven myself for these past mistakes? If not, how can I forgive myself and move on?  
  • In what ways have I hurt others? Have I sought forgiveness from them? From God? 
  • In what ways have others hurt me? Am I being called to extend forgiveness? If so, what might that look like?  

Not surprisingly, this first session was (although extremely cathartic) also quite difficult. Here, I found it helpful to be gentle and go easy on myself. I should also offer the following piece of advice: If you have suffered major trauma in your life— especially during your childhood years— it might be wise to do at least this section of the retreat under the supervision of an experienced spiritual director or licensed counsellor. To put it simply, there are some things that can be extremely difficult to face alone.  


Session 2: Celebrating the Past and Experiencing Gratitude

Spend twenty to thirty minutes in prayer and/or meditation. 

Prayerfully read Psalm 116

Ask yourself the following questions: 

  • As I look back on the past, what are some of the best decisions that I made? (As you think of things, thank God for giving you the guidance and strength to make those decisions).  
  • As I look back only life, what sort of things have I done that I can be truly proud of? When have I been particularly noble, self-sacrificial or courageous? (Take time to celebrate what God has done in your life).  
  • Looking back on all the people I’ve ever known, who has blessed me the most? Have I told them how much they mean to me? (Thank God for them).


Session 3: Looking to the Future with Courage

Spend twenty to thirty minutes in prayer and/or meditation. 

Prayerfully read Luke 3:7-17

Ask yourself the following questions: 

  • As I think about my future, what am I most afraid of? What are my greatest fears regarding my professional life? What are my greatest fears for my marriage and/or family life? How can I learn to be at peace with these fears?  
  • What are some negative or destructive attitudes and habits that I presently hold? How will these things negatively impact the people I love? What might my life look like in 10 years if I refuse to change? What about 20 years? What about when I’m 80 years old?  What can I do to begin the process of change now? 


Session 4: Looking to the Future with Hope

Spend twenty to thirty minutes in prayer and/or meditation. 

Prayerfully read James 4:13-16

Ask yourself the following questions: 

Imagine you are 20 years older (or any other duration of time that you feel is most appropriate).  Imagine that, in this ideal future, you are fulfilled and happy. Now, ask yourself the following questions: 

  • In this ideal future, what does my family/personal life look like? What about my professional life? How is my health? Be vivid and specific. Now ask yourself: What can I do within the near future to begin making this vision a reality? 
  • What major things do I feel God calling me to do within the next 20 years? (again, specify another duration of time as you feel most  appropriate).  

I can’t tell you that this two-day retreat was easy. It forced me to revisit dark parts of my past that I had left buried and untouched for many years. It forced me to confront my greatest sins and fears and regrets. But it was truly worth it. There were moments when I felt enveloped in an immense and awesome love— a love that was so kind, benevolent and forgiving that it made me weep with joy. Indeed, not only did I feel the love of the Living God himself but the love of countless family members and friends that He, in his infinite goodness, has placed in my life. How incredibly fitting, then, that my return to Saint John would be marked by a surprise birthday party that Jasmine had planned— a birthday attended by an astonishing variety of people (friends, family and church members)  each of whom have come to mean so much to both of us over the years.   

If you choose to undergo this or a similar kind of spiritual retreat, my hope and prayer for you too would experience healing, refreshment and, most importantly of all, the divine love that envelopes us all.