As I approached my mid-twenties, I wasn’t sure what I wanted to do next with my career. I enjoyed my work as a high school teacher, but sensed that teaching wasn’t going to be long-term for me. There were a few things I wanted to try, but I could feel inertia kicking in: if I didn’t set a new course soon, I was afraid I’d wake up one day and my chances would be gone (or at least greatly diminished).

So, I did what a lot of people do: I asked for advice from people I trust. I talked to my parents and to my closest friends, and I thought, and prayed, and thought some more. But it occurred to me that I was missing an important perspective: the moderately disinterested bystander.

Assembling outside voices

Now, don’t think I just wildly ambushed random people on the street and demanded, “What should I do with my life?!?!” I was marginally more thoughtful.

I decided to identify three people whom I knew a little, respected a lot, and reasonably liked. These were people I didn’t see frequently, who didn’t have any financial or professional interest in my life decisions, and who knew me — but didn’t know me terribly well.

I asked them if they would join my Life Advisory Board.

Yes, that sounds pretty weird. And two of the people I invited to join my board said as much, quite explicitly. (The third is too polite to say it, but he was probably thinking it.)

I explained that I wanted to live intentionally, and that in nearly every other meaningful aspect of our lives, we ask outside experts or objective observers to weigh in and to provide new perspectives. (Think: Your doctor. Your lawyer. Siri.)

I wanted their advice and their guidance. I wanted them to ask tough questions of me. I wanted them to hold me accountable. I wanted them to say, “You’ve been talking about ‘X’ for a few years, but you never seem to do it…why is that?”

And I also told them why I was asking them, specifically. One member of my board was a just-moved-on-to-a-new-job former colleague who was creative and adventurous while also being really grounded in his personal faith. I wanted to be all of those things.

Another was an older person who had been my boss’s boss during an internship I had while in college. She had worked in an industry that intrigued me, and she had broken down a lot of barriers throughout her career. I thought she’d help me see possibilities in my professional life and maybe urge me to be courageous in my personal life.

The last invitee was the father of a friend of mine from high school. I can point to one simple interaction I had with him that encapsulates my respect for him: I was at my friend’s house while we were in college, and I asked her dad if he had a go-to bar in the neighborhood where he liked to hang out. He looked at me and he said, “Chuck, when Mary [his wife] and I had kids, we decided that our kitchen was going to become our go-to place. This is where we want to be.” I sensed that he had his priorities straight; that’s what I wanted for myself. Still do!

Getting life advice

So, these three interesting, integrated, diverse people and I get together as a group — almost always by phone — two or three times a year for about an hour. I tell them what’s on my mind. I talk through whatever big decisions I’ve made recently or ones I’m trying to make. They ask questions and challenge assumptions.

The first “board meeting” was a bit awkward. Nobody quite knew how these conversations were supposed to go, or what was out-of-bounds. In retrospect, I’m glad that I brought a very concrete issue to that first conversation: Should I, or should I not, apply to business school?

I explained what I was considering, along with my list of pros and cons. And then, thankfully, the probing questions began: Why? Have you thought about…? Are you sure your assumptions are correct? It was a good, thought-provoking conversation.

Here’s how a more recent discussion went: About a year ago, sort of out of the blue, one of my board members said, “You know, in all the times we’ve talked, we’ve never discussed your physical fitness. Do you exercise?” The answer: No, not really…not since I played sports in high school. “Maybe that’s something you should think about. You’re not getting any younger, and exercise has lots of benefits that aren’t just physical.”

If those same words had been uttered by my mom, I probably would have rolled my eyes and ignored her. But for some reason, that encouragement, coming from an outside voice, resonated. And I’m glad it did. (Sorry, Mom.)

Making decisions grounded in perspective

I’ve connected with my advisory board now for about 10 years. I can’t say I agree with every bit of advice they give or that the members of my board agree with each other all the time. Sometimes I’d prefer I wasn’t asked about some corner of my life that I’d rather went unchallenged.

But the conversations I have with my board are incredibly rich, and their very existence helps me put things in perspective.

Having a Life Advisory Board is obviously a bit peculiar. But why should it be? Acknowledging that others can provide valuable insights, and committing to a somewhat formalized — though not stilted — routine of dialogue has made me more attuned to the undercurrents of my life, more appreciative of multiple perspectives, and more discerning about my next steps, big and small.