Where did you grow up and what was your childhood like? Did you have any particular experiences/stories that shaped your adult life?

I grew up in Washington, D.C., which was a great gift. From an early age, and with parents who were keen followers of current events, I was attuned to national and international news and public figures. I grew up with an awareness of the world at large, of history, of public service, and of a diverse community all around me.

What is something you wish you would’ve realized earlier in your life?

That there are always more options available than the ones you think of first.

What are bad recommendations you hear in your profession or area of expertise?

It’s less a recommendation than three assumptions: one, anyone can write and we (in an organization) don’t need to invest in headcount to get good writing and expertise; two, whichever writer we get can write about anything; and three, we don’t need an editor because we have a writer.

For one, let me just say writing is one of those invisible skills that is undervalued, and companies will try to get by with in-house help from people in a Swiss-Army-knife fashion. Two, writers come in all flavors. Do you need… advertising copy? Technical documentation? Speeches and presentations? Clever social media hooks? Well-researched white papers? An executive ghostwriter? There are writers who can do one or maybe two of these, but never all of them. Understand your needs and tailor the search to an expert in the area(s) where you need help.

And three, everyone needs an editor! An editor often is the person you need instead of a writer, in fact, because so much content comes from the collaboration between lots of people in an organization. And an editor can take a rough draft, your raw material, and make it better.

Tell me about one of the darker periods you’ve experienced in life. How you came out of it and what you learned from it?

About 20 years ago there was a big downturn in Silicon Valley — a major recession. No one was hiring, job openings froze, and everyone who *had* a job went underground. At the time I had just left a failed startup (turns out it was the canary in the coal mine! When money was still flowing freely, it could not raise a second round). And I had just bought my first home, a condo in San Francisco. And the condo needed months of costly renovation in order to be habitable. Bad timing! I did tap every source including mom for the renovation outlay and at the same cut my living expenses to the bone. There were no full-time jobs to be had, after years of me enjoying multiple job offers. So I convened a group of friends and colleagues who were in the same boat, work-wise. We met every week or two to support each other in our hunt for contract work, consulting, and the rare full-time opportunity. We practiced our pitches to one another and made introductions where we could. The group lasted nearly two years until the economy slowly picked up, and individually we found our paths forward. The wonderful thing about the group was that we all felt we were in it together. Even though no one could offer the precise solution for the others, the fact that we could share wins, losses, near misses, and be candid really helped us keep moving ahead. The lesson I learned was that to have a “brain trust” for yourself — a small group you can turn to for ideas, help, advice, and friendly support — is valuable no matter what the circumstances are.

What is one thing that you do that you feel has been the biggest contributor to your success so far?

Staying in touch with people. Since I’ve held lots of jobs and my areas of interest and expertise have grown, the fact that I am online a lot, and in touch with people informally and intermittently, has given me an easy to reach out with questions, to make introductions, and to gather new ideas. (And it led to my book.)

What is your morning routine?

When I get up around 7 am, I put on the coffee and take the dog out for a quick walk, just a couple of blocks. We come back to make breakfast (including that coffee for me!). Typically I sit down at the laptop to scan Twitter, email, and get a sense of my schedule and to-dos for the day. And my morning warmup to get my brain in gear means I send a few quick messages to people who have been on my mind or initiate a note asking if I can make an introduction or ask a specific question of someone. It’s a great way for me to awaken more fully for substantive writing or meetings to come.

What habit or behavior that you have pursued for a few years has most improved your life?

About a year ago I began taking at least one daily photo and sharing it on Instagram, Twitter, and FB with the hashtag #dailywalk. I started doing this in honor of a dear friend who was at that time dying of pancreatic cancer. It was kind of a vigil for him and reflected our long walk-and-talks around the city when we would notice our surroundings and riff on them. After he died I kept it up in his memory. People have come to enjoy my daily view of something that strikes me when I’m out walking the dog, whether it’s architecture or nature or some human markings like graffiti. Now part of my day is this quest to see something new (or see something in a new way), and I’m happy that others enjoy it.

What are your strategies for being productive and using your time most efficiently?

When I’m stuck mentally, or while writing, I get up from my seat and walk – sometimes a walk with the dog, or an errand or task around the house, to loosen up my mind and get myself off-topic for a few minutes. Most of the time that’s all it takes to get back on track. If I need more of a boost I’ll make a list or an outline of the task at hand so there are some steps I can focus on.

What book(s) have influenced your life the most? Why?

Here’s one: Carol Gilligan’s In a Different Voice, a 1982 critique of the fact that psychologists did not account for gender differences in their studies of how children developed. Instead, they preferred to generalize research about (and by) men to apply to all people, which led to women being “inferior” in their model. Gilligan believes that in reality the female approach to morality can be understood as different from men’s and studied on its own terms. I have thought about, and observed, her perspective in action over many years in business. Where men tend to see a bright line around a rule or a law, women tend to aim for nuance and context based on relationships and history between people. It’s not absolute, but it’s critical to understand the differences in how we treat and see, gender.

Do you have any quotes you live by or think of often?

An overriding thought I always have is: Context is everything. Context matters when it comes to human behavior, business decisions, weekend plans, serendipity, and structure alike. We don’t live in vacuums, and very little is clearly delineated. Virtually everything we do comes out of our expectations, upbringing, attachments, the current state of being, and limitations. That’s why it’s critical to understand the context in a story before we judge the person. It doesn’t mean we are unable to make moral distinctions but does require us to see as much of the whole picture as possible.