Last year, I got a call from the reporting assistant to Bob Woodward — the person who now holds the job I had 20 years ago.
She told me Bob was working on a reporter’s memoir — “not an autobiography,” she stressed, which I could 100% envision him saying. As part of that, she wanted to ask me what I remembered about my time with him.
We chatted, and then when I had some free time about a year ago, I flew down to DC to see Bob.
I realized that after working for him all those years ago and interviewing sources, the tables had turned and now I was a source.
Weirdly, as I think happens with a lot of sources for a lot of journalists, I nearly forgot about the experience—never mind whatever it was I actually said.
I mean, there was the Google Apocalypse to deal with and family vacations and the launch of Life Story Magic, and then I started to get some business consulting gigs, and a friend convinced me to spend some time putting together a draft of a memoir of my own, and I was coaching soccer and traveling with family and hitting the gym, and honestly just sitting back sometimes and looking at my wife and my daughter and my life and thinking how did I get so lucky ...
Then, Monday afternoon I was flipping through the digital version of The Washington Post and saw that the Post had “obtained” an advance copy of Bob’s manuscript, called Secrets: A Reporter’s Memoir, and summarized a lot of the book—thus giving away some of the secrets.
It’s a 592-page book, coming out November 24. Bob has apparently decided that after 55 years of reporting, and with many of his longtime confidential sources now dead, he can reveal some of the people who helped him get his biggest stories.
Examples:
How Nixon’s own defense lawyers were secretly talking to Woodward during Watergate.
How five Supreme Court justices secretly talked to Woodward and his co-author Scott Armstrong for their 1979 book, The Brethren.
How Woodward managed to get into the hospital room of CIA Director William Casey in 1987 — one of his "No way, how did he do that?" reporting moments — despite the security surrounding the gravely ill spymaster.
How? He’d spent years cultivating Casey’s security guards as sources, too. When he showed up uninvited, one of them greeted him with “Hi, Bob,” and simply let him in.
Actually, I guess I can now say that I can corroborate the Casey story—at least in that I remember Bob sharing it with me back in 2006.
Anyway, I thought I’d include something about this in Free for ALL Friday.
But then I saw yesterday that Bob had written a long article for The New Yorker, drawn from the book. I read it standing in my kitchen, start to finish, as soon as I saw it.
So let me share a personal thing or two about the oddity of me winding up working for Woodward, and what I learned.
When I was in 7th or 8th grade in the mid-1980s, I read All the President’s Men at least a half a dozen times.
I was really into it. I watched the film starring Robert Redford and Dustin Hoffman over and over, too, borrowing a VHS tape from the library in my hometown in Rhode Island.
Fast forward 20 years, and after a meandering path, I wound up working as Woodward’s lead reporting assistant for two years in the mid-2000s. In fact, when I started with Bob in 2005, I literally got off active duty in the Army JAG Corps on a Friday, and started working for him the following Monday.
It was only a few weeks after I started working with Bob that his Watergate-era source “Deep Throat” was revealed to the world, as the former #2 man in the FBI, Mark Felt.
So, I helped Bob quickly write his book, The Secret Man. I also worked on what turned out to be the “big project” during that time, his book about President Bush and the Iraq War called State of Denial.
Toward the end of my time working with Bob, a fellow journalist asked me for my big takeaways. I think he was hoping for some kind of magic spell that gets people to talk to journalists.
But it wasn’t that intriguing. It’s simply that you have to be willing to do the work.
Most people aren’t.
I think I was always a hard worker, and I could be determined.
But there was just something I learned in that job about being wiling to do the same things over and over — meeting people, conducting interviews, digging through documents — and accepting that most of the time it wouldn’t obviously lead to anything.
Because occasionally it leads to gold—but also because, quite frankly, it’s a lot of fun. In fact, I might well have spent my entire career trying to find ways to get paid to do that kind of work—one way or another.
Which brings me back to The New Yorker.
Bob’s article is called The Danger of Getting Too Close to a Source. It’s largely about his relationship with Richard Darman, who served in senior positions in the Reagan and George H.W. Bush administrations.
Darman was both one of Bob’s closest friends and one of his most important confidential sources. They talked constantly, and Bob says he interviewed him at least 58 times before their friendship ultimately fell apart in 1992.
Their friendship fell apart after Bob published a series of stories about the Bush administration's economic policies. Darman felt betrayed.
It’s a pretty remarkable account, especially because Bob writes about his own mistakes and regrets.
He says he and Darman never really reconciled before Darman died in 2008. And, he writes about his time as an editor at The Washington Post in the early 1980s, when one of the reporters under his supervision won a Pulitzer Prize for a story about an eight-year-old heroin addict that turned out to have been fabricated.
Bob calls it a professional and moral failure, and he describes the way he managed the reporters who worked for him—which led to some success but also to the fabrication disaster.
He gave them freedom, but demanded more and more. He’d push them to peel back additional layers of a story, sometimes telling them to go back and interview the same people four more times.
I recognized the single-mindedness. I recognized the willingness—even eagerness—to do the fourth interview, and the fortieth.
So, my takeaway? Talk to everyone. Ask questions. Be willing to look a little foolish sometimes.
Listen to the answers. Keep your recorder running. And, when you think you’ve got everything, keep pushing.
The best stuff always comes during the last 5 to 10 percent of your effort.
But also: Don’t be afraid to put it all aside to go and coach soccer.
Thank you for reading Understandably! If someone shared this with you, please sign up here for a free or paid subscription. I’m also grateful for one-off support (via Buy Me a Coffee) that helps me keep this whole thing going!
Other things worth knowing …
WaPo: I went to Mexico to test-drive the cars Americans can’t buy: What I saw was a split screen between a familiar past and a future of luxurious, space-age cars that cost far less than comparable models at home.
Reuters via Yahoo: The US Federal Election Commission’s website was targeted by a hacker or hackers, according to an email seen by Reuters, disrupting the agency’s electronic filings system a week before the November 3 elections. The hack comes as so-called super PACs and dark money groups spend record sums in the final days of the races. The FEC does not play a role in administering US elections and the outage should have no effect on voters’ ability to cast ballots.
The Guardian: A Florida surgeon has performed the first telerobotic operation between two US hospitals, removing the prostate of a man with cancer from 35 miles away, according to officials. Dr. Vipul Patel, founder and medical director of the Global Robotics Institute at AdventHealth Celebration in suburban Orlando, on Sunday performed an investigational robotic prostatectomy on a 66-year-old prostate cancer patient who volunteered for a clinical study evaluating a robotic telesurgery system.
ABC News: The Alexander brothers were each sentenced to 30 years in prison on Tuesday, after being found guilty on all counts in their federal sex trafficking trial in New York City. The former real estate titans, Oren and Alon Alexander, 39-year-old twins, along with their brother, Tal Alexander, 40, were accused by prosecutors of a “decade-long sex trafficking and sexual abuse scheme.” Assistant U.S. Attorney Elizabeth Espinosa asked the judge for the maximum sentence -- life in prison.
NYT: U.S. Pensions Are Riding the A.I. Wave. For Better or Worse: As exuberance around the technology stokes fears of a bubble, the nation’s public pensions are starting to grapple with their role — and their risks.
Axios: Prime Minister Benjamin Netanyahu’s far-right coalition is running nearly even with Gadi Eisenkot’s opposition bloc in Tuesday’s historic election — but both are short of a 61-seat majority, according to Israeli exit polls. Political stalemate is the most likely outcome of the election, with Netanyahu weakened but neither side having a clear path to forming a coalition government. Arab parties are poised to win 18 to 19 seats in what would be an unprecedented electoral achievement.
The Hill: A federal grand jury in Washington, D.C., on Tuesday rejected the Justice Department’s attempt to indict former White House aide Cassidy Hutchinson over her testimony to lawmakers about President Trump’s actions during the Jan. 6, 2021, attack on the Capitol. The decision marks another setback for the Trump administration’s efforts to pursue criminal charges against the president’s political adversaries.
Thanks for reading. Photo by Franki Chamaki on Unsplash. See you in the comments!

“ Talk to everyone. Ask questions. Be willing to look a little foolish sometimes.
Listen to the answers. … And, when you think you’ve got everything, keep pushing.”
As with anything, ask questions. Do not stop when you hear what you were expecting or wanted to hear. Build your next question from the last thing they said until they say no more.
Bill, as you said “… The best stuff always comes during the last 5 to 10 percent of your effort.” That is true in your writing as well as in life. You always seem to drop the best nuggets near the end!