How to Avoid Boondoggle Projects

I’ve spent too much of my life on absolute boondoggles of projects. Now, I know better.

To avoid boondoggle projects in any organization or team, these five questions must be clear to everyone (especially to me): who, what, to what end, why, and how.

Here they are:

• Who are we serving? Answering this provides clarity on whose needs we really have to meet and who the judge of success and failure actually is. If we’re not clear on who is saying “thank you” at the end of all this, how can we do something magical for them?

• To what end do we aspire? This clarifies what a successful mission looks like. The needle has to move on something; otherwise, why are we putting forth any effort?

• What are we delivering? This clarifies the tangible thing we have to put in front of someone’s face or into their hands. If we’re not clear on what we’re building, aren’t we all just wasting our time?

• Why does this matter? This clarifies the urgency and importance. If this doesn’t matter a lot, let’s respect ourselves enough to do something else that does.

• How are we going to get from here to the end? This clarifies the process. If we don’t know how to get this done, will we ever finish?

Answering these five questions is the cheapest, simplest project charter you’ve ever had. If everyone on the team has the same answers to these questions, you’ll prevent the project from becoming a boondoggle.

If we’re part of leading a project, getting the team to clarity on these five questions is our job.

“How do I become a good father?”

Let me be honest with you.

I don't know whether I'm a good man, whether I will be a good father, or even whether I'll ever have the capacity to know - in the moment, at least - whether I'm either of those things. I, nor anyone, will truly be able to judge whether I was a good father or a good man until decades after I pass on from this earth.

I do know, however, that is what I want and intend to be. I want to be a good father and the father you all need me to be.

Wanting to be a good father was my central objective in writing this book. The sentiment I had in the Spring of 2017, a few months before Bo was born, is the same sentiment I feel now – I want to be a good father, but I need to figure it out. I am not nervous to be a father, but I’m not sure I know how just yet. I am excited to be a father, but what would it mean to be a good one? What do I need to do? How do I actually do it? How do I actually walk the walk?

This book is my answer to this simple, fundamental, difficult question: how do I become a good father? In this letter and the letters that follow, my goal is to answer that question in the greatest rigor and with the most thoughtfulness I can. As you’ll see in the pages that follow, the answer to the question quickly becomes an inquiry on how I become a good person myself, because I need to walk the walk if I want you three to grow to become good people. As it turns out, the best way (and perhaps only way) I could adequately answer this question with the intensity and emotional labor it required was by talking with you all – my three sons – and writing to you directly. You boys are the intended audience of this volume of letters.

When I first started writing in 2017, your mother and I only knew of Robert’s pending birth, though we dreamed of you both, Myles, and Emmett. And by the grace of God, all three of you are here now as I begin rewrites of this manuscript in the spring of 2022, about three weeks after Emmett was born. Now that you three are here, I have edited this volume to address you all in these letters collectively, even though that wasn’t the case in my original draft.

At the beginning of this project, I wasn’t sure if I would share it with anyone but our family. But as I went, I started to believe that the ideas were relevant and worth sharing beyond our roof. This book become something I’ve always wanted from philosophers, but I felt was always missing. As comprehensive as moral philosophy and theology are with the question of “what” – what is good, what is the right choice, etc. – what I found lacking was the question of “how”. How do we actually become the sort of people that can actually do what is good? How do we actually become the sort of people that make the tough choices to live out and goodness in our thoughts and our actions? How do we actually learn to walk the walk?

This question of “how” is unglamorous, laborious, and pedantic to answer. It takes a special kind of zealotry to stick with, especially because it requires a tremendous amount of context setting and when you’re done all the work you’ve done seems so obvious, cliché even. And yet, the question of how – how we become good people is so essential.

Perhaps that’s why philosophers don’t seem to emphasize it, but parents and coaches do. Coming up with the “what” is sexy, cool, flashy, and novel and once you lay down the what, it’s easy to walk away and leave the details to the “lesser minds” in the room. On the contrary, you have to care deeply about a person to get into the muck of details to help them figure out “how” to do anything. Figuring out the how is a much longer, arduous, and entangled journey.

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This passage is from a book I’ve drafted and am currently editing. To learn more and sign up to receive updates / excerpts click here.

Debrief questions for parents (and coaches)

I have been struggling for a long time thinking about how to teach our sons “character.” They won’t learn it from a book, nor will sending them to Catholic school magically make that happen.

What dawned on me this week, is that I can debrief with them. And really do that intentionally.

I attended a wonderful summer camp in high school, it was “student council camp.” And there were lots of character building-activities, that I still remember and think about often. 

When I become a camp counselor, I had the opportunity to facilitate those character-building activities. And what we always said amongst other counselors is that it’s not the activity that teaches anything, “it’s all about the debrief.”

Debriefing - the process of helping others learn from their own experiences - is a hard-earned skill. It’s not easy. But it’s essentially all about asking the sequence of questions that highlight the salient information which lead to a a novel insight.

During a debrief, the goal isn’t to tell anyone anything, the goal is to nudge them along by bringing relevant facts to the debriefee’s attention which causes them to have an “aha moment”. In those aha moments, so to speak, they learn a lesson on their own. Good debriefers don’t teach, they help others teach themselves.

Cutting to the chase, I started putting a list of questions that could be used to debrief, even with young children. I needed to write them down to debrief myself I suppose. 

I share that list here in case it’s useful to those of us that are parents or coaches. I also share it here in hopes that others share their own debrief questions. If you’re uncomfortable leaving a comment, please do contact me if you have a thought to share, I’d be happy to append it anonymously.

Debrief Questions for Parents and Coaches

• How do you feel right now?

• Are you okay?

• Can you tell me exactly what happened?

• Then what happened?

• What were you thinking right before you did X?

• How do you think this made [Name] feel?

• What can you do to make this right?

• Why didn’t X, Y, or Z happen instead?

• What were you trying to do by doing X?

• What could you have done instead of X?

• Was doing X okay, or not okay? Why?

• What else happened because you did X?

• Do you have any questions for me?

• What are you going to do differently next time?

• What happens next, right now?

What am I doing with my surplus?

My feelings about "privilege" are complicated.

On the one hand, the data is clear that certain factors that we are born into - like race, gender, sexual orientation, zip code, etc. - are predictive of how healthy, wealthy, and at peace we become.

On the other hand, those with "privilege" still have to avoid screwing up the privilege they have to become healthy, wealthy, and at peace. And that's not trivial, either.

On the other hand, privilege is used as leverage to exploit those with less money and power. That exploitation is wrong.

On the other hand, I can't and don't want to live in a perpetual state of guilt, apology, doubt, and shame about any "privilege" I have. I didn't choose to be born into privilege or non-privilege, just like everybody else.

So what do I do with these complicated feelings?

It seems just as wrong to skewer people with privilege as it is to suggest privilege is a conspiracy. And having some sort of atonement about privilege through acknowledgement or "checking" privilege seems okay, I guess. But I honestly don't know the material, sustained effects it has on our culture. It doesn't seem like enough to simply become aware of privilege.

I've been thinking about this idea of "privilege" lately because of Thanksgiving. I feel extremely lucky to have steady work, work that doesn't require leaving my house, and health insurance. I have a family that I love and loves me back. I have friends and neighbors that I love, and love me back. When people have asked me, "what are you grateful for this Thanksgiving?" these are the things I've talked about.

Talking with and listening to my brother-in-law on Thanksgiving, inspired a different path.

It was helpful to replace the world privilege with "surplus". I have a lot of surplus. I was born into a life of surplus. There are other people who were also born into a life of surplus.

Nobody chooses what surplus they were born into.

But everybody chooses what they do with the surplus they have.

What am I doing with my surplus?

Am I trying to get more? Am I trying to shame others because they have more surplus? Am I trying to reallocate surplus after the fact? Am I trying to convince myself that I deserve the surplus I have? Am I using my surplus to enrich my own life and that of my friends and family with ostentatious luxuries? Am I wasting my surplus? Am I trying to acknowledge and atone for my surplus? Am I trying to stockplie it? Am I trying to bequeath it?

Or am I trying to use the surplus I have to enrich the lives of others?

I honestly don't know if this is the best answer on what to do with these complicated feelings about privilege. And maybe there doesn't have to be one "answer" in the first place.

But the best I can come up with is not worrying so much about privilege itself, and who has more of it than me. To me, it makes more sense to worry about whether I am enriching the lives of others.

"To who much is given, much is expected" is an old idea, but it seems like an enduring and worthwhile principle to apply to this befuddling idea of privilege.