My Top Books of 2021

The problem with setting a low goal for yourself is that you just might reach it. While I recognize how absurd it might be to say that 60 books in a year is “low”, when you look at previous years, you understand.

The beauty of plowing through 80+ books in a year is the sense that you can read a bit more indiscriminately. Read whatever you want, you’ve got plenty of ground to cover. There’s a confidence in knowing that no matter what you read, great or terrible, there’s an ending on the other side. In ratcheting back to 60, I felt the constriction. I had to start strategically planning what books would be next. Every read felt like it had to count.

The sad part is I don’t feel like I read any better, wider, or that the books I read were any longer in length. I just simply read less. There were periods of time where I would’ve normally chosen to read that this year I chose not to. Why? Because I didn’t have to try so hard.

When initially thinking about this year, I had hoped that somewhere during the year my daughter would figure out her life and begin sleeping regularly. This was the case briefly. Then, we got pregnant with baby number two. All this to say that next year might be even more challenging to carve out space and time to read. Still, I’m finding it vital not just to my personal and spiritual life but also my inner life as a leader. Reading stimulates thoughts and begins internal dialogues I wouldn’t have otherwise. As busy as things get, I want to continue to make it a practice and continue giving myself lofty reading goals.

What’s surprising to me is that these might not be the best books I read – you could make the argument that any given book on my overall list was better than one listed at the top – but these are the ones that made their impression.

In no particular order:

  1. Elon Musk – Ashlee Vance
Elon Musk: Tesla, SpaceX, and the Quest for a Fantastic Future, Vance,  Ashlee, eBook - Amazon.com

As strange as it sounds, I actually didn’t know much of anything about Elon Musk before reading this book. I, of course, was familiar with Tesla and SpaceX but that’s about it. Even now, I don’t know much about him or his work since this book. I’m not a fanboy nor am I Musk-ian leader but it made me think about leadership profiles, futuristic thinking, and transcendent purposes that inspire unconventional, if not innovative business practices. It made me think about start-ups, the bold invitations they’re built on, and the people they attract. At times, it reads like hero worship, but even so, it’s still fascinating.

2. The Meaning Revolution – Fred Kofman

The Meaning Revolution: The Power of Transcendent Leadership: Kofman, Fred,  Hoffman, Reid: 9781524760731: Amazon.com: Books

I don’t know how much I’d recommend this entire book. Honestly, it’s a slog, but I don’t know if I read a book this year that shaped my understanding of organizations more than this one. Kofman gets into the main tension all organizations face. Namely, if a department does what’s best for them, they will invariably cripple the entire organization. As much as people think their titles are their jobs, their real job is to help the team win. Staff and departments must suboptimize for the organization to thrive. The only way you can get people to do that is through transcendent leadership. That premise alone made it worth being on the top of the list. The introduction is worth the price to me.

3. Leading With a Limp – Dan Allender

Leading with a Limp: Take Full Advantage of Your Most Powerful Weakness:  Allender, Dan B.: 9781578569526: Amazon.com: Books

I honestly I don’t know if I’ve read a more depressing book on leadership than this one, but it was that same candor I found refreshing. Here’s someone who’s been there, done that, and sees through all the B.S. Rather than a clarion call to triumphalist leadership, it’s a sobering look at the summons given to us. Considering this current cultural moment we find ourselves in, his thoughts on reluctant leaders felt prescient.

4. Love is an Orientation – Andrew Marin

Amazon.com: Love Is an Orientation: Elevating the Conversation with the Gay  Community: 9780830836260: Marin, Andrew, McLaren, Brian: Books

This book was recommended to me nearly ten years ago and, for better or worse, I just got around to it (I think that should tell you something about giving me book recommendations). Any missionary that embeds their life with another group of people over a long period of time – especially, when that group of people is a community they wouldn’t ordinarily belong – will always have my utmost respect. You get the sense that Marin’s life was disrupted by Jesus, and he’s done his best to be obedient. To me, this also seems to say something about how calling works. He doesn’t answer all your questions, but he elevates the conversation to where dialogue between two different, often warring parties are possible. I will say, though, because of the gap between its commendation and my reading of it, I couldn’t help but wonder if others more versed in this conversation would find this book outdated.

5. The Second Mountain – David Brooks

The Second Mountain: The Quest for a Moral Life: Brooks, David:  9780812993264: Amazon.com: Books

This was one of those books I saw in everyone’s top reads last year, so when my spiritual director mentioned it to me, I knew I had to read it. There’s a reason it’s on everyone’s list. It’s an absolute tour de force that could only have been written by someone who has (or is) climbing that second mountain. It’s written with both the pain and humility that comes from failure or hardship and yet, while it’s sad in some respects, it’s also hopeful and insightful. In some ways, it’s the perfect foil to Elon Musk.

Other notables:

  1. American Kingpin – Nick Bilton
Amazon.com: American Kingpin: The Epic Hunt for the Criminal Mastermind  Behind the Silk Road eBook : Bilton, Nick: Kindle Store

If you’re looking to read something fun and absolutely wild, this is the book for you. I practically live under a rock, so I had never heard of the Silk Road before this, but this is real life Breaking Bad type stuff, cloaked in libertarian philosophy. It’s so well-written you would think it’s a novel or true-crime television. It will have you on the edge of your seat.

2. Surprised by Paradox – Jen Pollock Michel

Surprised by Paradox: The Promise of "And" in an Either-Or World: Michel,  Jen Pollock, Ramsey, Russ: 9780830845644: Amazon.com: Books

Evaluating a book can be tricky business. Sometimes a book has wonderful ideas but is poorly executed. Other times, the book is beautifully written but lacks substance. Jen Pollock Michel excels in both. This is the second book I’ve read from her where time and time again I found myself grateful to God for her, her insight, and her ability to articulate it so well.

3. Caste – Isabelle Wilkerson

Amazon.com: Caste (Oprah's Book Club): The Origins of Our Discontents eBook  : Wilkerson, Isabel: Kindle Store

When The Warmth of Other Suns is your first book, how do you follow that up? While Caste doesn’t carry the same narrative power that made her first book so remarkable, the ideas and the parallels she draws to history are incredible. I don’t know if I’ve ever considered America’s racial dynamics as a caste system but when she explains it, it makes so much sense it’s scary. Once again, she and I are not related but if she wanted to claim me, I’d gladly graft our family trees together.

4. Think Again – Adam Grant

Think Again: The Power of Knowing What You Don't Know: Grant, Adam:  9781984878106: Amazon.com: Books

Honestly, seeing this book on everyone else’s list made me reconsider its placement on mine. I was such a big fan of Originals that I had unbelievably high hopes for this one. It’s not that I thought this book was bad. It just wasn’t Originals. Revisiting it now though, I’m reminded what I appreciated about this book. This isn’t one to just listen to. It’s one to physically own, mark, and take notes from. Shoutout to Adam Grant and everyone else who made me, for lack of a better phrase, think again.

5. Reading While Black – Esau McCaulley

Reading While Black: African American Biblical Interpretation as an  Exercise in Hope: McCaulley, Esau: 9780830854868: Amazon.com: Books

Honestly, this book probably deserves to be higher but it’s just a matter of when I read it. The theological and hermeneutical work by him is serious.! Once again, one of those books that you can’t listen to, but you need to physically own. The way he uses scripture to talk about the pursuit of justice even as he later uses it to talk about the call to forgive is incredible. In a world demanding binary options, McCaulley isn’t interested in sides. He’s interested in the Bible. He made me want to be a biblical scholar.

The Full List (asterisk indicates audiobook):

January

  1. Hood Feminism* – Mikki Kendall
  2. Jesus Outside the Lines* – Scott Sauls
  3. Bad Blood* – John Carreyou
  4. Tempered Resilience* – Tod Bolsinger
  5. Elon Musk* – Ashlee Vance
  6. Ready or Not – Doug Paul

February

  1. A Promised Land* – Barack Obama
  2. Caste* – Isabel Wilkerson
  3. Didn’t See It Coming – Carey Nieuwhof
  4. One Blood* – John Perkins

March

  1. Dust Tracks on a Road* – Zora Neale Hurston
  2. American Kingpin* – Nick Bilton
  3. Dear Girls* – Ali Wong
  4. The Four Tendencies* – Gretchen Reuben
  5. The Meaning Revolution – Fred Kofman

April

  1. The Second Mountain* – David Brooks
  2. The Ride of a Lifetime* – Robert Iger
  3. The Devil in White City* – Erik Larson
  4. Thinking, Fast and Slow* – Daniel Kahneman
  5. With Open Hands – Henri J.M. Nouwen

May

  1. Visioneering* – Andy Stanley
  2. Think Again* – Adam Grant
  3. Mission Drift* – Peter Greer
  4. Steve Jobs* – Walter Isaacson
  5. Begin Again* – Eddie S. Glaude
  6. Everything I Never Told You* – Celeste Ng

June

  1. American Dirt* – Jeanine Cummins
  2. Blue Ocean Strategy* – W. Chan Kim, Renee Mauborgne
  3. Permanent Record* – Edward Snowden
  4. The Vanishing Half* – Britt Bennet
  5. Right Here, Right Now – Lance Ford, Alan Hirsch

July

  1. The Membership Economy* – Robbie Kellman Baxter
  2. Discovering God’s Will Together* – Ruth Haley Barton
  3. Concrete Rose* – Angie Thomas
  4. The End of the Affair – Graham Greene
  5. On the Verge – Dave Ferguson & Alan Hirsch
  6. Love is an Orientation – Andrew Marin
  7. The First Time Manager – Loren Belker, Jim McCormick, Gary Topchik

August

  1. Leading with a Limp – Dan Allender
  2. Why We Drive* – Matthew Crawford
  3. Fault Lines* – Voddie Baucham
  4. Surprised by Paradox* – Jen Pollock Michel
  5. The Fruit of the Spirit – Thomas Trask & Wayde Goodall

September

  1. When Narcissism Comes to Church* – Chuck DeGroat
  2. The Starfish and the Spirit* – Lance Ford, Alan Hirsch, and Rob Wegner
  3. How Music Works* – David Byrne
  4. Executive Presence* – Sylvia Ann Hewlett
  5. Cultivating the Fruit of the Spirit – Christopher J.H. Wright
  6. Surprised by Joy* – C.S. Lewis
  7. Influencer – Brittany Hennessy

October

  1. The Madness of Crowds* – Douglas Murray
  2. Grace Will Lead Us Home* – Jennifer Berry Hawes
  3. Something Needs to Change* – David Platt
  4. When* – David Pink

November

  1. Empire of the Summer Moon* – S.C. Gwynne
  2. There There* – Tommy Orange
  3. The Divine Conspiracy – Dallas Willard

December

  1. Bury My Heart at Wounded Knee* – Dee Brown
  2. Leadership in Turbulent Times* – Doris Kearns Goodwin
  3. Reading While Black* – Esau McCaulley  

Published by Tomy Wilkerson

"Here is a trustworthy saying that deserves full acceptance: Christ Jesus came into the world to save sinners of whom I am the worst." - 1 Timothy 1:15

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