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Debra Pickett: “Kids are resilient”

Kids are resilient. For all our worry and grief over what they’re losing, kids do find their way to joy. In my reporting career, before I went into business, I spent time in Kenya and Tanzania at the height of the AIDS orphan crisis. In the slums of Nairobi, there was essentially an entire generation […]

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Kids are resilient. For all our worry and grief over what they’re losing, kids do find their way to joy. In my reporting career, before I went into business, I spent time in Kenya and Tanzania at the height of the AIDS orphan crisis. In the slums of Nairobi, there was essentially an entire generation of kids who’d lost their parents to the AIDS pandemic. Yet there was also music and laughter and soccer and tag. I hold that in my mind.


The Covid-19 pandemic has affected nearly every aspect of our lives today. Many of us now have new challenges that come with working from home, homeschooling, and sheltering in place.

As a part of our series about how busy women leaders are addressing these new needs, I had the pleasure of interviewing Debra Pickett.

As Founder and Principal of Page 2 Communications, a boutique consultancy providing media strategy, content marketing and public relations services to law firms and their clients, Deb leads a team of experienced journalists, editors, marketers and media analysts in leveraging communications to fuel business development. With a particular focus on how equity and inclusion in the legal industry drive client service and growth, she is a strategic advisor to an emerging generation of firm marketers and leaders as they reimagine tired narratives and policies. Informed by her experience as an award-winning print and television journalist, she is also adept at helping clients manage through crisis, shape public opinion and influence government policy.


Thank you so much for doing this with us! Before we dig in, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

When I was in my 20s, working as a reporter and then columnist for the Chicago Sun-Times, I was pretty sure I had the best job in the world. I had a front-row seat to history and, even more, was helping write its early drafts. I’m deeply proud of some of the work I did then, chronicling the re-opening of Civil Rights-era murder cases and the world’s response to the AIDS orphan crisis in Sub-Saharan Africa.

When our first child was born, my husband and I struggled to figure out how we could be the kind of parents we wanted to be while also continuing to pursue our careers. His job at the time involved near-constant travel, while mine had irregular hours and high-pressure deadlines. Eventually, we both made big changes. I became a freelance writer, and he started his own consulting business.

The creativity and flexibility of the freelance life were wonderful for me, as our family grew to include our three sons, born in 2006, 2008 and 2009. I wrote my first novel and volunteered for the Obama campaign.

Seeking more structure, challenge and opportunity, in 2010, I took a full-time job with a public strategy firm. I loved applying my communication skills and re-connecting to my media contacts in service of meaningful causes and advocacy groups. That firm had several lawyers as clients, providing them with PR and other marketing services, and I found that I gravitated to that side of the business. It had the same intellectual and strategic rigor as the political work, but the hours and travel expectations were much better aligned with the needs of my family.

After a year spent learning the business from a talented mentor there, and inspired by my husband’s success as an entrepreneur, I launched Page 2 Communications in 2011.

Can you share the most interesting story that happened to you since you started at your company?

Because my core clients are law firm managing partners and practice leaders, I often find myself in situations where I’m the only woman in the room.

Fairly early in my firm’s history, I pitched our services to a national law firm that was newly entering the Chicago market. I was quite confident that we were the best agency to serve them and, indeed, as their selection process narrowed, the decision was down to two finalists: Page 2 and a much larger PR firm that did not specialize in legal marketing work. In the end, though, the law firm partners selected our competitor, mostly on the “vibe” they got from the male account executive who’d made the pitch.

As it happened, that PR agency did not serve this law firm particularly well and, a year later, when their initial contract was up, instead of renewing it, the law firm reached out to me and asked if I’d submit another proposal for the work. This time, the final decision was placed in the hands of the firm’s Chief Marketing Officer, who happened to be a woman. She not only selected Page 2, but was quite clear in her comments to the male partners who’d made the original selection that she believed they’d lost a valuable opportunity to build the firm’s reputation in the Chicago legal community during that critical year simply because their chauvinism prevented them from understanding whose expertise they truly needed.

Are you working on any exciting new projects now? How do you think that will help people?

Since our founding, Page 2 has been solely in the professional services business. But, this year, we’re working on potentially launching something very different: a subscription-based product.

Our consultants can only work with so many law firm clients at a time, but packaging our analysis and business intelligence into an electronic newsletter will give us the opportunity to connect with the legal industry at a much larger scale.

I’m really excited about building this out. There’s the technology and design piece — creating something that is truly worthy of time and investment from very busy law firm leaders and executives — as well as the whole visioning process, working with my team to create a prototype and then testing it out with our brilliant and ruthlessly candid clients. Selfishly, it’s just fun stuff to dig into. Beyond that, though, I’m excited about what we might be able to do as publishers adapting cutting-edge business intelligence for the law firm context. Lawyers want to keep up with what’s in the Harvard Business Review and the Financial Times, but they just don’t have the time to dive into everything that’s out there and they especially need guidance in laying out practical steps for transforming ideas into action.

I think of myself, sometimes, as an accidental entrepreneur. And lawyers are very much in that same boat. They chose law school over business school, yet, as they succeed in their legal careers and advance in their firms, they essentially find themselves becoming managers of large businesses. I think there’s a tremendous opportunity to create a resource that helps them navigate those executive aspects of their roles.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I’ve been incredibly fortunate to have generous and enthusiastic mentors throughout my life, but there are a handful who have had the greatest influence on my chosen path.

John Kealey, the CEO of the tech start-up where I worked in the late 90s, taught me far more about business and leadership than I realized at the time. Paul Saltzman, my primary editor at the Sun-Times, made me a much more thoughtful, careful writer than I ever knew I was capable of being. John Calloway, my great hero in broadcast journalism, pushed me to be courageous about the stories I chose to tell.

Those three mentors shaped my approach to work, but my business would not exist in the form that it does today if it weren’t for the influence of a fourth role model: Tony Nasharr. The Managing Partner of Polsinelli’s Chicago office from 2006–2017, Tony was one of Page 2’s earliest clients and most enthusiastic supporters. His introductions and referrals are the core of our business, even today. He saw the value that we — a small band of former journalists, writers and campaign veterans, with not a lawyer or an experienced marketer in the bunch — could bring to the business of building a law firm brand, creating a new market presence and establishing a reputation for innovation in a tradition-bound industry. In a business that values who you are and who you know, he looked beyond those things and saw us for what we could do. He recommended us for work that should have, by all rights, been out of our grasp because he knew that we could rise to the occasion.

I’ve expressed my gratitude to Tony personally many times, but the best way I know to demonstrate my appreciation is to follow his example and pay forward his generosity, so I try to keep that in mind whenever I can. I go out of my way to make connections and introductions for people because I understand how much it means, in your early days, to have someone opening those doors for you.

The Covid-19 pandemic has affected nearly every aspect of our lives today. Can you articulate to our readers what are the biggest family related challenges you are facing as a woman business leader during this pandemic?

HuffPost ran a piece earlier this month entitled, “Wrangling Kids’ Distance Learning While Working From Home Is A Hellscape,” and, quite honestly, that probably articulates the challenge better than I could.

I won’t sugarcoat the fact that it’s extremely challenging to have three kids at home doing full-time remote schooling while also trying to run my business from home. There are times when there is not enough literal bandwidth for all of us: if our boys all are on Zoom for classes, my husband and I can barely manage to access our emails, let alone participate in video conferences of our own. So there’s a significant logistical and organizational burden involved in coordinating everyone’s schedules, and the result is that my days are very long. I’m up and on my computer for 2 hours or more in the very early morning hours before the kids start their day, and then, very often, back on my computer late at night after they’ve gone to bed. In between, I schedule conference calls with my team and our clients and hop back and forth, over the course of the day, between those responsibilities and checking in with my kids.

My sons are old enough that they don’t need direct adult supervision all the time, as long as you’re OK with them playing a lot of video games. (And let me just be clear that I am fully OK with that. Restrictions on screen time went out the window FAST when the pandemic hit.) But they’re also old enough that they understand the gravity of the situation we’re all in. They worry about their grandparents staying healthy. They are deeply frustrated by all the adults who have failed to meet the challenge of this moment. They’re sad about not seeing their friends and not having their usual sports and activities. I feel like their emotional needs are more significant and complicated than they’ve ever been and, as a parent, I should be able to give them reassurance, but I often find myself at a loss for words. I grieve for everything they’ve lost and everything they’re missing.

Can you share what you’ve done to address those challenges?

First, I’d say that I’m being more honest and candid with my family than ever before. I’ve always been a “never let them see you sweat” kind of person and that was true in my home life as well as my work life. But in recent months, I’ve had days where I’ve just had to say, “I’m exhausted” or “I’m worried.”

My husband and I have always had a pretty equitable partnership, but the division of household labor and responsibilities that we had so carefully laid out simply was not workable in the early days of the pandemic when there were suddenly extra meals to cook, grocery shortages to manage, crises with my clients and my employees, and a lockdown that meant our house cleaner couldn’t come to work. He had to step up to do more cooking and more “kid management” than he’s ever had to do. If he hadn’t, I would not have been able to navigate my business through this.

As we’ve settled in, my family and I are very consciously trying to find the positives in our situation. First, we know we are incredibly lucky and privileged to have our health, to have our work and incomes, to have a safe and comfortable home and all the technology to support us in working/schooling remotely. These might be stormy seas to navigate, but we’re in a very sturdy boat, while we know many others have little or nothing to cling to. We are grateful for our good fortune and do what we can, in donations and service, to share what we have with others.

Second, this slow-down has given us the opportunity to spend a lot of quiet, gentle time together that we would never have had otherwise. We’ve watched a movie together almost every night. Two hours on the couch together, with PJs and blankets and snacks — that was a rare treat when everyone had sports practices and activities every night. In the summer, we carved out one day a week for an outdoor adventure, visiting many of the beautiful state parks in our home state of Wisconsin, and having picnic lunches together.

In my low moments, I’m comforted by the thought that I’ve been able to give my kids the gift of some really happy memories despite the difficult times.

Can you share the biggest work-related challenges you are facing as a woman in business during this pandemic?

Women business owners tend to have less robust networks and connections — there’s just a lot fewer of us — so I think it was a lot more challenging for many of us to get access to the resources we’ve needed to navigate the pandemic.

In my own situation, while Page 2 has had a business relationship with the same bank since I started the company, we’re a bootstrap business. We never had a line of credit or a loan package beyond a corporate credit card. And actually when I did look into to setting up a more complex financing arrangement in connection with an expansion deal we were considering, the commercial banker I dealt with was dismissive, to say the least. (As in: he wanted my husband to co-sign.) So, when I needed to access PPP funds to keep us going through the early days of the lockdown (when a number of our clients had put freezes on paying their bills), it was a real struggle to get someone at the bank to pay attention to us and actually process our application. At one point, I emailed the bank CEO and the entire executive committee. At age 47, I’m pretty fearless about doing things like that, but I don’t know that I would have done that 10 or 15 years ago and, if I hadn’t, I don’t know that we would have gotten the funds we needed to keep paying employees during those critical first few months.

Can you share what you’ve done to address those challenges?

The biggest financial challenge we had was cash flow. PPP support certainly helped with that, as did the great partnerships we have with our clients. We actually had a couple of folks pay our invoices using their credit cards so that we could get paid right away while they waited for their firms to reimburse them when payables were frozen. We had others who went out of their way to get us included on their firms’ “essential vendors” lists or who set up electronic payments rather than their usual paper checks. That kind of consideration for our circumstances was breathtaking. I’m eternally grateful.

As a manager, the biggest challenge was helping guide our team through these circumstances. I have employees who were suddenly at home with young kids and no child care and others who were trying to be productive in shared apartments with no dedicated work spaces. Our clients had tons of work that needed doing — letting their clients know about virtual work arrangements, standing up new COVID and crisis-related practices, helping businesses comply with new regulations — and our capacity to actually deliver that work was really constrained. The first thing I had to do was roll up my own sleeves and help serve clients directly. The next was to work with each team member individually to find ways to structure their time and priorities so that they could be as productive as possible.

In meeting the first challenge, we also were better able to meet the second. I was able to pay everyone their full salaries from March through July even if they weren’t working their full-time schedule. In removing some of that anxiety, we were able to help people lean in and do their best.

Can you share your advice about how to best work from home, while balancing the needs of homeschooling or the needs of a family?

Structure and planning are key. We have a family Google calendar where we track all of our schedules, so everyone can see who’s doing what when. On Sundays, I sit with that calendar and look at the week ahead to plan a menu. If there’s an evening when I’ve got a board meeting that’s going to run late, that will be a night that my husband and/or one of the boys will need to be in charge of dinner, so I’ll make sure that we have a meal kit or something they’ll want to make. The menu determines the grocery list and on from there. Removing chaos and last-minute decisions makes the week go much more smoothly. To the extent that you can do so safely, getting help and/or outsourcing some tasks is also really vital to making this work.

For me, it’s challenging to work with full concentration or flow during the “school day” hours when my kids are supposed to be in virtual classes. I’m worried about them being on time, getting connected and focusing on their work, so I always seem to have one ear listening for whatever is going on with them. I don’t try to force myself into that; I work around it. If I have a big presentation or meeting that requires my full attention, I schedule it for Wednesday (their “asynchronous learning” day when there aren’t any live classes) or before or after their scheduled class times (9:10 am — 1:45 pm).

Can you share your strategies about how to stay sane and serene while sheltering in place, or simply staying inside, for long periods with your family?

Living with my very extroverted husband and our 3 boys, ages 11 to 14, I really can’t say much about serenity.

But sanity has been relatively easy. We try to laugh more than we yell or cry. We’ve radically lowered our standards on some things (see “screen time” above, but also: cereal as a meal, various standards of cleanliness and personal grooming, and bedtimes) and given up entirely on others. It’s fine.

Our 2 younger boys were sharing a bedroom and, as time passed in lockdown, we realized they each really needed some private space, so we set to work on a family project that finished a room in the basement for our oldest son to move into, Greg Brady style, and then began shifting everyone’s stuff into three separate rooms. The project kept us busy and the (almost) end result has been well worth the effort. Sometimes, no matter who you are or what age you are, you just want to shut the door behind you and be alone for a little while.

Many people have become anxious from the dramatic jolts of the news cycle. The fears related to the coronavirus pandemic have understandably heightened a sense of uncertainty, fear, and loneliness. From your perspective can you help our readers to see the “Light at the End of the Tunnel”? Can you share your “5 Reasons To Be Hopeful During this Corona Crisis”? If you can, please share a story or example for each.

5 Reasons To Be Hopeful During this Corona Crisis:

  1. Kids are resilient. For all our worry and grief over what they’re losing, kids do find their way to joy. In my reporting career, before I went into business, I spent time in Kenya and Tanzania at the height of the AIDS orphan crisis. In the slums of Nairobi, there was essentially an entire generation of kids who’d lost their parents to the AIDS pandemic. Yet there was also music and laughter and soccer and tag. I hold that in my mind.
  2. Entrepreneurs are too. We fail more than we succeed. Yet we keep going. I’m really inspired by all the people I see “pivoting” their businesses to meet the moment — the clothing companies making masks, the restaurants offering takeout and outdoor dining, the hotels creating quarantine spaces and solo offices — and I genuinely believe this same vital energy will help us all find ways to move forward.
  3. Gen Z is amazing. Say what you will about the “greatest generation” of old, the young people in this country who have taken to the streets — the Parkland kids standing up to gun violence, the Sunrise Movement organizing school strikes for climate change awareness, the Black Lives Matter protestors risking their own lives to force us all to focus on police brutality and other forms of systemic racism — are the lifeblood of democracy. I believe they’ll save the world.
  4. We can’t unsee the inequities laid bare by the pandemic. Just as cell phone and dash-cam video technology has forced us to acknowledge the violence endured by Black people at the hands of the police, the data about disparities in health care, job security and educational resources we’re seeing reflected in the disproportionate toll the pandemic is taking on communities of color is undeniable. Confronted by this reality, we are compelled to act.
  5. The global community is coming together to meet this challenge. Notwithstanding the political situation in the U.S., all around the world, doctors and researchers are collecting data about the virus, sharing what they know and working together to build predictive models, public health and therapeutic interventions and, we all hope, a vaccine. The virus is borderless, but so is this collective progress and innovation. As someone who follows media closely, when I see publications all over the place sharing their pandemic-related content for free, as a public service more important than selling subscriptions, I’m very hopeful that we’ll all find our way back to each other and to a shared notion of community.

From your experience, what are a few ideas that one can use to effectively offer support to their family and loved ones who are feeling anxious? Can you explain?

My youngest son’s fifth-grade teacher has been telling him and his classmates, “We can do hard things.” I can’t think of a better motto than that.

There have been so many moments, over the last several months, when I’ve thought, “Well, this is it. I can’t make this work.” But, somehow, just past each of those moments, something has worked. Pretty much any one of us reading or participating in this conversation, just by virtue of our being here, has incredible resources and reserves — advantages unimaginable to women in other parts of the world. Yes, our circumstances are hard, but we are also well-equipped to do hard things.

It’s totally normal and rational to feel anxious in times like these. And sometimes we have to stop and sit with that anxiety for a little while before we can move forward. But we can move forward. We always do.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

The lock screen on my phone shows a quote from Angela Davis, “I’m no longer accepting the things I cannot change. I’m changing the things I cannot accept.”

The sentiment is, of course, a twist on the serenity prayer, which was a favorite of my grandmother: “God grant me the serenity to accept the things I cannot change, the courage to change the things I can and the wisdom to know the difference.”

As I mentioned before, I’m not much on serenity. Maybe I will be when I’m a grandmother myself, but, somehow, I doubt it.

There have been many points in my life when I could have accepted the status quo and things would have been fine for my family and me. I think back to the late spring of this year. We’d been in lockdown for months and, as I’ve described, my business was burning through cash to pay our folks while several of our largest clients simply weren’t paying us. I did briefly consider just “shutting down” for a while. It would have been nice to have had that time with my kids and not had the stress of dealing with the super-dysfunctional PPP rollout. Certainly my employees wouldn’t have been alone in being furloughed or laid-off during that time. But I couldn’t accept that. We’re a strong business doing excellent work for great clients. I would not accept that we couldn’t keep going.

There’s another motto I live by, which is written on an iron arch over the gate to the main campus of my alma mater, the University of Pennsylvania: “Inveniemus aut faciemus viam.” Either we will find a way, or we will make one. That’s how I’ve approached being a woman business owner and a working mom and, so far, it’s worked.

How can our readers follow you online?

Twitter at @DebPickett

Page 2 Communications: https://page2comm.com/

Thank you so much for sharing these important insights. We wish you continued success and good health!

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