For over a decade, Jake Sherman has built a career landing hard-to-get scoops while chronicling legislative battles on Capitol Hill and the cross-country struggle for control of Congress. Now, in the midst of a global pandemic and an unpredictable presidential race, the “exercise fanatic” reveals his on-the-beat strategies as well as his go-to spots he plans to enjoy again both on and off the job … once social distancing lifts.
Can you describe how your job has evolved in the time of COVID-19?
Well, it’s certainly different. I am spending much more time in my house with my family — a far cry from the House periodical press gallery. But Playbook is more necessary than ever to make sure our audience is up to speed on everything going on on the Hill and in the White House.
You’ve had a prolific news career at a young age. Do you feel you have accomplished what you set out to do journalistically?
Absolutely not. Who could ever feel like they’ve accomplished what they want to do at 34? This is a great profession where you’re only as good as your last story (or, in my case at the moment, Playbook).
Describe the election campaign this year and how it may be particularly distinct from others you’ve covered.
The Democratic field has so little clarity. All campaign seasons have a familiar rhythm and familiar vibe, but this Democratic primary is definitely different. Mike Bloomberg and his endless money give this a completely new feel than the past. We have nothing to compare it to.
Everyone is trying to get the biggest news scoop. What’s your strategy for getting one?
No matter what beat you cover, show up when you need nothing. This is a lesson I learned early on. If you are standing outside the meeting when nothing is happening, people will be more likely to help you when something is happening. Make small talk with your sources. Talk to them about things outside of work.
Is there some place local you go to take a break from politics?
This question assumes I take a break. We write something like 600 Playbooks a year. But [apart from the gym] I go to a good number of concerts—although far fewer than I did before children.
You often travel for your job. How do you stay healthy and well?
I strive for 40 to 50 minutes of exercise every day no matter where in the world I am. Healthy eating is also key.
Speaking of traveling and flights, you often post live flight trackers on Twitter. Can you explain the fascination?
I don’t know how to explain it besides saying that I always want to know things that people don’t want me to know.
Flight tracking is an extension of that. If you weren’t covering politics, what else would you do? I’d be covering sports.
I love sportswriting.
Favorite District team?
This is a tough one. I have to go with: the GW men’s basketball team and the Washington
Nationals. I don’t know that I’ll ever love a team as much as I loved the 2019 Nats.
Any personal goals for 2020?
Learn a page of the Talmud (Jewish oral law) every day.
Is there a particular lesson from growing up that influences your every day drive?
If you love what you do, you will never work a day in your life.
Last question: What keeps you up at night?
Nothing. When you don’t get a lot of time to sleep, you sleep.
My Top Spots
One of my favorite places to write, and where I wrote part of the “The Hill to Die On: The Battle for Congress and the Future of Trump’s America,” (Crown, 2019) is the Cleveland Park Library on Connecticut Avenue NW.
Even though I have been working there nearly every day for more than a decade, the U.S. Capitol is still my favorite place in Washington. It’s majestic, full of history and very accessible to guests.
Washington has lots of great golf courses. I try to explore and play at as many of them as I can (My favorite is the north course at Woodmont.).
I am an exercise fanatic, so when I’m not with my family or working, I’m working out. I go to exercise classes around town like Orange Theory and Barry’s Bootcamp.