The next four years will be some of the most challenging of Skye Perryman’s career. Donald Trump has returned to the White House as emboldened conservative lawmakers across the country scale up their anti-democratic attacks on free speech, civil rights, and access to reproductive health care; Democracy Forward, the organization that Perryman leads, will be at the forefront of challenging these policies in court.
The last time Trump was in office, the organization defended the rights of groups including immigrant workers, uninsured Americans, and school-aged children. For nearly two years leading up to the 2024 election, Democracy Forward identified potential actions Trump and his second administration could take and prepared to combat them by scouring through policies from his previous term, his campaign promises, and the far-right presidential transition plan Project 2025.
On Monday, Democracy Forward and 280 other organizations launched Democracy 2025, a resource center that will allow the public to keep track of the new administration’s actions and how they can respond. All of this planning for Trump 2.0 has made Perryman, a lawyer by training, incredibly busy as she tries to balance lengthy days and frequent travel with carving out time for family and friends. “This is heavy work against really long odds,” she says. Perryman lives in Washington, D.C., with her husband and their 9-year-old son. Here’s how she gets it done.
On her morning routine:
I usually wake up between four and five in the morning. The first thing I do is meditate for about 15 minutes and set the intention of the day. Then I start diving into what’s happened overnight in my inbox. The early morning is a good time for work that requires a lot of time and concentration, which I don’t get in my busy day. At some point between then and 7:30 a.m., my son will get up. I’ll enjoy spending some time with him and then our nanny comes. I’ll get ready for the day and get into work. I’m an iced Americano drinker; sometimes I do that decaf. I sometimes start meetings as early as 7 or 7:30 a.m., but most of them start around 8 or 8:30 a.m. On days when I don’t have early meetings, I’ll do drop-off at school, which is within walking distance from our home.
On her varied workday:
I could be on Capitol Hill testifying or traveling to meet with our partners. Recently I started out with our all-staff meeting — I try to attend those because it’s a good opportunity to connect with all of our teams. Later, I led a meeting of about 250 peer organizations and advocates to figure out how we could facilitate collaboration between the communities we serve. I edited several documents and then connected with two team members on a hard problem we are working on solving to meet the needs of one of our clients. In the afternoon, I went to the Hill to brief some members of Congress on legal challenges that may be needed to stop the implementation of unconstitutional executive orders and to protect health-care access and labor rights. Somewhere in there, I also talked to several reporters about a case we’re looking to file, worked with my team on scheduling some TV appearances for shows that asked for legal commentary, and texted with three of my son’s friends’ parents regarding a carpool to basketball practice.
On how she came to head up Democracy Forward:
I am a product of K-12 public education, and when I was in college I had a job working in public schools in Central Texas. That really motivated me because I saw the difference that could be made. Then, early in my career, I came to Washington and interned on Capitol Hill. I realized that a good way to make a difference is to understand how laws and policies are created and shaped, so I went to law school. I worked at two amazing law firms that had corporate clients, but also I always had pro bono clients — abortion providers, medical professionals, people whose civil rights have been violated. After the 2016 election, I saw lawyers making such a difference by protecting the underlying rule of law in our democracy. I had just had my son and was really concerned about the future for him and his generation. I joined Democracy Forward as a litigator and then left to be the general counsel at the American College of OBGYNs. That was an important pivot in my career because I gained a lot of executive-leadership skills. I led a large team of not just lawyers but communications specialists, policy advocates, and others. I saw how all the pieces go together and found that work to be so rewarding. But the January 6 violent attack on the Capitol really brought home that this was not going to be a momentary challenge, that these attacks and threats on the rule of law and on our democracy were not going away. That’s when the Democracy Forward board asked if I would be interested in returning to expand the important and powerful early work we did with people across the country.
On preparing for the Trump administration and emboldened state actors:
This was not a moment that people started planning for just after the election, but one that we had been prepping for some time. A lot of this is about collaboration with other organizations and communities across the country that are concerned about this moment, making sure that we have a longer-term vision and strategy. We have been looking at threats to our democracy, including those in Project 2025 and other extreme proposals that we are concerned about happening at the federal level, including many of them that we saw last time the Trump administration was in office.
On the people who help her get it done:
My husband; our wonderful nanny, Daisy; my friends; and the phenomenal staff that I get to work with. We have an amazing team that helps make sure that I’m scheduled in a really efficient manner.
On what keeps her grounded:
Making space for my family and friends — cooking, hosting, and gathering people when I can — is very refreshing. I’m always trying new things, but the most comforting recipes that I make are often around the holidays or other big events. They’re usually recipes from my grandmothers and people that have loved me. Being outdoors is really important too. Washington is very close to the beautiful Shenandoah Valley and the Blue Ridge Mountains, so we spend a lot of time out there.
On her evening routine:
My days are long. When I get home depends on a mix of personal and professional commitments. On the days I’m able to come home early, I enjoy cooking and we have dinner as a family. If there’s a little extra time before my son’s bedtime, we play board games. There are times after my son goes to bed that I’ll have to do some late-night work. Sleep is a really important thing, so sometimes I’ll get in bed as early as 9 p.m. But there are times that I’m in bed a bit later and I don’t get as much sleep. I do a lot of my resting on the weekends.
On the advice she wishes she could give her younger self:
There isn’t a final success, and there isn’t a final failure. Early in my career, I was a bit more anxious about making a mistake and feeling like I wasn’t 100 percent. But I got in and did the work. You don’t have to fear mistakes or failures — I don’t even like those words, because those are just opportunities and challenges.
On the hardest part of her job:
We’re supporting communities across the country who are experiencing attacks on democracy, like librarians and teachers that are facing book bans and people who are suffering from not being able to access reproductive health care. We don’t win every fight that we take on. Many days are quite devastating for the people that we have the honor of representing. Holding that truth is challenging. We seek to do a range of things to help our staff be able to take care of themselves, whether that’s a lot of flexibility in our working day or the ability to take an extended vacation so that people can really get out and unplug. One of the best pieces of advice that I got and repeat all the time is, “When you’re tired, it’s important to rest. But do not quit.”
This interview has been edited and condensed for length and clarity.