The Mysterious Mentor Adventure

On the morning my mom passed away I had to write her obituary. I had been putting it off. Meanwhile, there was a stream of people coming by the room at the hospice facility where we were. I couldn’t talk. I couldn’t even write the thing without my hands shaking.

When I was finished, I walked to the front office and delivered the paper to the hospice representative. I walked outside, sat on the curb and sobbed. Mom was my first mentor.

If we are lucky, we will have more than one mentor in our lives. I’ve been fortunate to have six amazing ones in person, so far (not including my parents), and many virtual ones. Because it’s an ongoing process, it is important to try and learn something from everyone. Everyone knows something we don’t.

Dad always used to say, “Wanna get good at something? Find someone who is and let them kick your ass at it, over and over, until you are, too.” Now that is some great advice. Wanna know why? Because it has worked without fail. WITHOUT FAIL.

Let’s do a little inventory. Right now I mentoring a 3-year-old, a 19-year-old and two 20-somethings who have worked with me in the recent past. It is tough to say who learns more from who. Who are my mentors? Honestly, I am in dire need of a solid mentor. It’s been a total drought these past couple of years. That’s how it goes, sometimes. Even so, don’t give up. It’s easy to feel alone in times like that. Like tides, good mentors’ presence in our lives tend to ebb and flow.

I suppose it is true to say the three-year-old (my little boy) is mentoring me. He pushes my imagination, for sure. We come up with games that, to us, are epic. We constantly find new ways to do mundane things – making washing the dishes a game of space ships refueling and finding places to land, mealtimes are comedies of voices, actions and anything to make it fun when he’d rather play than eat and, generally, we are constantly finding new ways to make waiting a rewarding exercise in play (the quiet kind).

So, I can’t really say I don’t have a current mentor, just not the sort that can ramp me up in other contexts. That is temporary, though. We always find them when we least expect it. Maybe it is a bit like love, that way: hard to find while we are searching far and wide for it.

As time goes on, the goal is to also get better at choosing the quality of people who mentor us. That, too, is a learning process.

The thing with learning is: it’s not a passive activity. It’s not just automatically ‘on’ all the time, like an automatic seatbelt or an airbag that is active without any intervention on our part. Like listening, it takes focus and practice focusing to do it better and better. If we think we can learn everything by osmosis, we are only partly right.

Here are some suggestions on how to find good mentors:

The Search

The heavy lifting of it is research. Reading their LinkedIn profiles, any online bios, personal and/or professional histories, anything that can be found – interviews are good, too. Send them a note that you read all about them and why you think they are interesting. We all like to know someone is out there listening and/or reading and it feels good when others care about the work we do and share. This is less about flattery and more about validation.


Comments are good but ideas on how to improve ideas are even better. When we comments on a book they’ve written or an interview we’ve watched, it is worthwhile to offer up something of our own, something that represents our own ingenuity, creativity and insight. Doing this often involves more research. It only makes sense that we would have to spend some time on someone before someone wants to spend time with us.

Yoda sketchPresence

We cannot expect to send one message, even a well-crafted one chock full of visionary ideas, and get an enthusiastic response from a future mentor. Be present. Active. Around. If they are all we expect they are, they are busy and are likely already engaged in mentoring others.

So, send an update every week or two. Do this for a while. Be consistent. Like I said, it only makes sense that we would have to spend some time on someone before someone wants to spend time with us.

In this case, quantity is as important as quality.


Let’s say they like our ideas and send a response! There is still work to do.

At this stage, it is essential we makes ourselves available because we can pretty much guarantee they are less available than we are.

Time is the most valuable asset anyone has. We only get so much of it. Need money? Need something else? Those things can be gotten but time is a finite resource for everyone, regardless of how much money and resources they have. We cannot expect someone to spend it on us if we do not honor and value it highly.

Real vs. Virtual

Some of my greatest mentors have been virtual. Smart people, while providing a lot of value, can also be very draining in person. Some don’t even know it. Choose ones that don’t drain us.

There are multiple methods of receiving mentorship and all are equally viable depending on the mentor and what we want from them.


Everybody and their Aunt Jane has ideas. Mentors are especially surrounded by people with ideas. There is no shortage of ideas but what sets us apart is something actionable or execution. Perhaps it is sending some referrals or leads their way. Maybe it’s executing on an idea, gathering some information and sharing it (micro-pilot, anyone?) – something that demonstrates that we are valuable and can not only offer ideas and feedback but deliver on it, too.

Then, share these updates every three-four months or so. Over-deliver.

the karate kidVariety

I think it is wise to have many mentors that to turn to for areas of expertise outside of our own, specific focus. It is a difficult thing to try and determine how to limit our learning. Many things that seem unrelated are not and can inform our work in ways studying the same thing over and over can never do. For example, it confuses me that all marketers, for example, ever write about is marketing. How can they know anything about people if all they focus on is how to sell them stuff? Besides, I feel very strongly that the ability to tell a story about how we learned something is just as important as what we learned. Often, the story is the real knowledge that leads to discovery of something much larger.

It’s also important to keep in mind that a mentorship can last for an undefined length of time. Some last years while others last hours. Just because a mentorship is short does not mean it was not successful and vice versa.

Sometimes the best ones involve a lot of investment in many contexts, including chronological, emotional and more. Others are like running into just the right sort at the gas pump, they say something out of the blue that makes something huge click and we are never the same for it.

Indeed, our influences are an elusive thing. Experience is the move but not just experience but capacity for it.

These relationships will have their own complexities, such as love/hate when we succeed beyond our mentors, which eventually we all will. This makes some of them hate us, the lesser ones. The better ones will be proud and get great satisfaction from our success. These are the mentors worth seeking out, the ones lacking self-consciousness, the ones who are solutions-oriented, even to a fault, and concerned more with, as my dad said, leaving the place better than they found it.

If they stop providing value, that’s okay. Our lives all tend to go in different directions, but, if we are patient, many of these connections will circle back, often years later in different capacities. This has happened to me and it is often more satisfying than the original engagement. When it comes to mentoring, both being a mentor and being mentored, it is important to keep in mind that it is a long game. Try to be grateful and let it play out.

There is no way we can know the role our efforts or those of others in these searches and engagements will play in our lives at their beginnings. Only in time will their value be revealed. That’s why finding and learning from mentors is indeed a most mysterious adventure.