Mentoring in retirement sounds like a wonderful idea. “Invest in the next generation. Share your life experience. Feel a renewed sense of purpose.” But in reality, far too often mentoring feels awkward for both mentor and mentee.

To the mentee, it can often feel like a mono-directional exchange of information, the older imparting “wisdom” to the younger during weekly or monthly appointments. Interactions are often confined to stiff formality and contrived “coffee chats” in which a mentor is supposed to (halo glowing) grace the young Padawan with Yoda-like insight. Anxiety bubbles under the surface for the mentee: will I be heard in this meet, or just get “should upon” for the next hour?

To the mentor, the high expectations surrounding mentoring can create a sense of pressure and a feeling of inadequacy that deters people from mentoring in the first place. Doubts creep in. Do I really have something to share with the next generation? Would they want to listen?

There are few things so human and so cross-cultural as the older grandparent, parent, boss or teacher sharing insight and life experience with the grandchild, child, employee or student. But I’ve found the entry point into a mentoring relationship makes all the difference. The best mentoring relationships often look more like intergenerational friendship.

Skilled mentors often share five characteristics.

1. Skilled mentors find genuine delight in the next generation and develop friendship based on common interests.

It might be baseball, city government, or philosophy. But rather than starting a mentoring relationship with a “you need this” mentality, talented mentors often develop the relationship because they’re actually curious about the young person, want to learn alongside them, and they share a common interest. This kind of humility cracks open the door for learning to be mutual and shared, rather than one way. This mutuality builds the trust necessary for not just skill transfer but spiritual formation to take place.

2. Skilled mentors bless and affirm a younger generation.

Rather than pointing out deficiencies, elders who become effective mentors are first people of wisdom and blessing.

For example, in Clint Eastwood’s colorful film Gran Torino, Walt Kowalski, a hardened, cursing, and angry Korean War veteran, ends up mentoring Thao, a Hmong teenager in Detroit who tried to steal Walt’s car. Out of shame for his offense, Thao’s family makes him do yard work for Kowalski for two weeks.

During those two weeks as Thao does chores for Kowalski, Kowalski enters Thao’s world by eating food with his family, showing him his garage full of tools, and by encouraging him to date “Miss Yum Yum,” a Hmong teenager that Thao struggles to even make eye contact with. Kowalski affirms the confidence-less Thao and even lets Thoa borrow his precious 1972 Gran Torino to bring his girlfriend to the movies.

Thao – like so many mentees – didn’t first need advice. Rather, he needed to know he was valuable and had something unique to offer the world. He needed an elder to affirm his identity and point out his unique talents and value.

3. Skilled mentors share their stories and are genuinely vulnerable with their mentees.

The truth is, young people want to hear more about your mistakes than your successes. Having done hundreds of panel presentations for my work, I’ve found that vulnerability always goes way further than expertise. Advice is fine – when asked for. But hearing honest stories allows mentees to learn from a mentor’s mistakes, and, hopefully, not repeat them.

4. Skilled mentors are patient and commit to long-term relationships.

Michael Lindsay, the president of Gordon College, says about mentoring, “What does matter [for the success of young adults] is the formative influence of an adult who speaks into your life and who has sustaining relationship that you carry with you.” If each of us thinks of the people who’ve deeply influenced our lives, these are generally people we’ve known not for weeks or months, but for years. And they’ve endured our silliness, our sin, our mistakes – and are still there for us.

5. Skilled mentors ask more questions than they give answers.

Jesus himself was master of the penetrating question. Questions like “What do you want me to do for you?” made Jesus’ disciples stare into their own souls, and ask what they truly desired. Of course, Jesus gave answers too. But genuine spiritual formation requires introspection, reflection, and prayer that is often the fruit of the right question at the right time.

Shaping the Next Generation

Harvard sociologist Robert Putnam says about the growing social divides in America, “If America’s religious communities were to become seized of the immorality of the opportunity gap, mentoring is one of the ways in which they could make an immediate impact.”

What if the 87% of Baby Boomers who believe in God decided that a central way they were going to spend their retirement was by mentoring young people through their local church? What if America’s retirees traded comfort for purpose, and swapped retirement villages for communities of intergenerational friendship?

What if retirement became a source of renewed purpose for older Americans who decided to share their lives especially with young adults who needed their affirmation, delight, vulnerability, and patience?

“It is more blessed to give than to receive,” said Jesus (Acts 20:35). But Jesus also says that it’s not knowledge but action that brings the blessing. 

“Now that you know these things, you will be blessed if you do them” (John 13:17).

This article is an adapted excerpt from my book An Uncommon Guide to Retirement: Finding God’s Purpose for the Next Season of Life.