Teaching iteration

I’ve written about the class I’d like to teach, but what I’ve been thinking about lately is the class I’d like to attend. Not necessarily now, but when I was growing up. In the 6th grade, let’s say.

I don’t know why people ask me this, but I’m often polled for my opinion on the American education system. What’s my take? What would I do to fix it?

I don’t know, really. “It” covers too much ground to be addressed accurately. Education is delivered at every scale, from an individual reading a book, to a 1:1 tutor, to a small home/classroom setting, to a larger university auditorium-sized class, to online classes that can be theoretically taken by the entire planet at once. From one to 7 billion.

You can’t fix anything that’s so big and so varied. You can, however, fix small parts of things. And hopefully, as the small, fixed parts add up, you have a chance at chipping away at a big problem.

So here’s my one small idea: I’d begin to teach iteration. Iteration as a subject, equivalient to math, science, history, language, art, music, etc. How do you make something better over time? How do you return to something that you’ve done and see it with fresh eyes? How do you apply new perspective to an old problem? Where do you find that new perspective? What trails do you follow and which do you ignore? How do you smash the familiar and reassemble something new from the same pieces?

Once you’re done with school, and cast out into the world, your job is likely to involve iteration. No matter what you’re doing, you’re probably going to have to do something over. And often times again and again. You rarely simply deliver something and move on. You’re asked to refactor, to build on it, to “make it better”.

Making anything better is iteration. When you put something out there, it’ll often land right back in your lap. Sometimes that feedback boomerangs back directly, other times you have to infer the problems by disciphering other people’s behavior when they interact with the thing you gave them. This customer struggled with this, this manufacturing tolerance didn’t line up with that, this printing process looked better on the screen than it did on paper. Or after a certain amount of time passes while working on something, you reflect on what you’ve done and don’t like the reflection.

Either way, someone’s probably going to ask you to take the state of your art, and make it the state of the art.

Now that you’ve got it back, what do you do with it? This is something you have to learn how to deal with. But in school — save for writing a few drafts before handing in the final version — you don’t get to iterate much. You move on from assignment to assignment, rarely getting a chance to revisit your work earlier in the semester. I think that’s a missed opportunity.

So, perhaps for a final assignment (no matter the subject), students should be able to choose something they did earlier in the year and get a chance to improve on it. Make version 2. I think working on four things, and getting a chance to redo one of them would be more valuable than working on five separate things. It would be a better education.

Or another take would be a single assignment for the entire semester. Every two weeks you hand in a new version of it. In time you may slam into diminishing returns, but that’s all part of it too. That would be a better education.

Or maybe you work on something and hand it in. Then the teacher shuffles the deck, so to speak, and hands you back someone else’s assignment. Now you have two weeks to improve on that. And that cycle — improving on someone else’s work — continues for the whole semester. That would closely mirror what work on the outside is really like. That would be a better education.

I don’t know, something like that.

So there, I guess that’s my initial idea to improve the educational system. Teach problem solving through iteration. Bounce things back to people for a second or third try. And then a fourth and a fifth. And so on. Require them to bring new perspectives. Demonstrate how time, space, and chance are on your side — they give you the opportunity to wander around with an idea and take it in new directions. Iteration is evolution. Hopefully what’s next is better than what came before it.

A question of skills

One of the first books I can remember reading was A Wizard of Earthsea. I was seven or eight, and it scared me to my core. That dark ocean was real and menacing in ways I couldn’t fully appreciate until later.

Beyond fear, one of the things that stuck with me from that book was the idea of true names. David Mitchell’s love letter to Earthsea paints the picture:

Knowledge of a thing’s true name brings mastery over the object, and as this applies to people as well, to tell someone your true name in Earthsea is an act of intimate trust.


I remember reading that tweet, and how violently I agreed with it. Hard/soft always felt jarring somehow. Ok, gone. I’m warming my hands on the smouldering embers of the dichotomy.

“So, what do we call them instead?”


Back in January, Seth Godin proposed vocational skills and real skills:

Let’s call them real skills, not soft.

Yes, they’re interpersonal skills. Leadership skills. The skills of charisma and diligence and contribution. But these modifiers, while accurate, somehow edge them away from the vocational skills, the skills that we actually hire for, the skills we measure a graduate degree on.

So let’s uncomfortably call them real skills instead.

Before we anoint a replacement, let’s take a moment. Why are we making that distinction? How does this benefit us? How does it help us to achieve our aims?

Almost everyone I’ve spoken with, and every post I’ve read, agrees that hard skills are easier to measure. That soft skills are more difficult to pin down, but equally important (I’d argue even more so). I can buy that. So what?

Dividing skills into types is an attempt to be more precise that costs us clarity instead of adding it. Our every instinct tells us that precision is valuable. Language is an evolving, imperfect attempt to describe the universe. When we reach for precision, we’re hoping to get closer to the true name of things.

There’s a trap here. When we spend time and wit seeking a more perfect description of the different types of skills, we’re working at the wrong level of abstraction. Precision only helps us if it changes how we act.


There doesn’t need to be a distinction. Skills are skills. We can teach them. You can learn them. There’s no meaningful difference in the steps you take to develop a ‘vocational’ skill or a ‘real’ skill, a ‘hard’ or a ‘soft’ skill. An authoritative taxonomy of skill types doesn’t change how you approach things.

What do we need to pick up a new skill? Well, some combination of the following:

  • Time
  • Desire
  • Access to knowledge
  • Practice
  • Observation
  • Making changes in response to what you observe
  • Support

Measuring success is the same whether you are learning HTML or practicing sincerity. You observe outcomes. You need to understand what you are trying to do before you do it, a core part of mastering any skill.

Making this change is pretty straightforward. When you are working on a job post, you already don’t mention hard or soft skills. You talk about the skills and experience you’d like an applicant to have. If you are working on a training plan for yourself or a team member, you can list the skills you want to focus on. Save yourself the mental overhead of working out if a skill is vocational or real. You won’t need it.

We can discard the distinction without guilt. Chipping away at gendered stereotypes is reason enough. Part of the evolution of language is recognising when words are no longer true, or shouldn’t be. We should seek a more comfortable level of abstraction, a truer name.

The names we choose matter.


With endless thanks to Ursula K. Le Guin, who influenced me more than I ever realized. A huge thank you to Erika Hall for prompting this in the first place. Thanks also to Mathew Cropper, Chase Clemons, Brad Stott, Elliott Hilare and Yechiel K for talking with me about this and helping me to see beyond my limits. 💚 to Chase Clemons, James Glazebrook & Wailin Wong for editing.

Work Can Wait 4,380 days

Or maybe it can’t. It’s your choice — That’s the point.

I love seeing the look on people’s faces when they learn I took 12 years off to raise my kids. They say, ‘But you’ve got such a great career in high tech! How’d you do that?’


I’m living proof you can take a break from your career to do something important to you and still have the career you want when you’re ready. For me, that break was to raise my boys — for you, it could be to travel, care for a family member, pursue an interest, give back or just chill.

Own your work-life decisions

I was the first person in my family to go to college. My Cuban-born mother had an eighth-grade education — my father graduated from high school. I earned a scholarship to Columbia University’s School of Engineering, where there were only three women in my electrical engineering class. After graduation, I got married and started my career in the high-tech industry. I loved my work.

A couple of years later, I had my first son. I fully intended to go back to work after my maternity leave, but the moment I held my son, I knew I wouldn’t be returning to work — not yet. There was something else I wanted to do more: raise my children.

This wasn’t an easy decision. I carried the yearnings of generations of women in my family who hadn’t had my opportunities. They couldn’t understand how I could ‘walk away from my career,’ and they couldn’t see a path for me to walk back later. I also loved my work, I was making a lot of money and I had financial independence. Yet, there was a voice inside telling me to embrace parenting. I listened. I knew on some level that taking time out of my career to do something I REALLY wanted to do wouldn’t be the end of my career.

But this post isn’t about whether to stay at home or to have a career; it’s about trusting your intuition, following your heart and having faith in yourself.

How to take time out of your career without ending it

There is no blueprint for making work wait for 12 years. And yet, I’m always asked how I did this. I never had a plan. I made my choices along the way.

Even though work was waiting, learning new things never did. During those 4,380 days, I thought of my children as my most meaningful work—the immovable priorities in every day—and I chose other pursuits that could fit around them. I earned a teaching credential, taught computer classes and taught myself emerging technologies. (My work passion was also my hobby, which I shared with my children, teaching them to program in Basic.) I consulted to small businesses and helped them set up their networks, volunteered at my sons’ schools and always worked part time around their schedules. In my 12th year out of the workforce, I got a full-time offer to build out a college technology center, join the faculty and then become dean of instructional computer technologies. Later, my self-taught Unix sys admin skills landed me at a company that taught Unix classes in Silicon Valley. It was perfect for me.

From that point forward, as I had before, I used my troika loves of emerging technology, applying technology to business problems and serving customers to choose my next move. I went to business school — my boys would post my report cards alongside theirs on our refrigerator. After I earned my MBA, I worked at email marketing company MarketFirst, then went on to content management software company Interwoven. When I realized I had a passion for the consumer online, I went to Yahoo, where I lead a global team of over 400 professionals in more than 20 countries. I followed my interest of ecommerce and women as CHOs (chief household officers) into a role first as CTO and then as CEO at Myshape (personalized online shopping experience) and then became the GM of ecommerce at Sears Holdings. Which brings me to my role today as chief operating officer for Basecamp.

Along the way, I concentrated on the choice that was in front of me. I never tried to calculate how to land at some future state of my career.

4 Tips for making choices and taking chances

Your career is one part of your life — it’s not your whole life. This is what I learned when I reset my life-work balance for 4,380 days:

  • It’s personal. There is no blueprint. You have to find your own authentic path and make it work for you.
  • Own it. If you don’t believe in your choices, no one else will either.
  • Focus on your strengths and passion. I am passionate (maybe it’s the latin blood). I never wavered from my mission of using emerging technology to help businesses and people be better — even when I hit the pause button on full-time work. Do what matters to you.
  • Don’t let others define you. When others attempt to put you in a box, they’re merely projecting their own fears on you. Resist the temptation to limit yourself because of someone else’s fixed mindset or because you’re afraid.

I’m a better leader because I did what I was drawn to do. It took courage then, and all these many years later, I find myself working with co-founders who have the courage to say this very thing to all of our employees. So, it turns out work can wait. Now that both of my sons are pursuing their own careers, families and passions, I feel energized to continue pursuing mine, knowing that one of my passions has multiplied my efforts.

Sometimes, work can wait — whether that means thousands of days or just evenings and weekends. If you agree, check out our Work Can Wait pledge, and hit the 💙 button below.

What are questions?

An unexpected answer from Clayton Christensen.

A few years ago I was fortunate enough to spend about three hours with Clayton Christensen. Clay, currently a professor at Harvard Business School, is best known for his book, The Innovator’s Dilemma. His latest book, How Will You Measure Your Life, has some wonderfully insightful business and life lessons.

His books, thinking, and approach to life, business, — and now, teaching — have influenced me greatly. I recommend reading everything he’s written and watching any videos of him you can find. Clay’s site is a good place to start.

What impressed me most about Clay yesterday was his clarity. He’s a very clear thinker and communicator. His genuine interest for helping other people discover clarity comes through with every patient word.

This one thing thing he said

Spending time with Clay leads to lots of interesting insights, but for me, there was one that stood out among all the others.

You’ve probably heard it said that someone can’t be taught until they’re ready to learn. I’ve heard it said that way too. It makes sense, and my experience tells me it’s mostly true. Why though? Why can’t someone be taught until they’re ready to learn?

Clay explained it in a way that I’ve never heard before and I’ll never forget again. Paraphrased slightly, he said:

“Questions are places in your mind where answers fit. If you haven’t asked the question, the answer has nowhere to go. It hits your mind and bounces right off. You have to ask the question — you have to want to know — in order to open up the space for the answer to fit.”

What an insight. He continued to talk about the power of questions. Questions are your mind’s receptors for answers. If you aren’t curious enough to want to know why, to want to ask questions, then you’re not making the room in your mind for answers. If you stop asking questions, your mind can’t grow.

That day had a profound impact on me. It’s so easy to think you know, but most of the time you’re really just being defensive — protecting yourself against the truth about something you think you’ve already figured out. Make room, make room. It’s a life-long pursuit.

(Special thanks to Bob Moesta for inviting me to meet Clay)


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What’s the difference between time and attention? A lot.

I recently realized that if I’m too busy to take something on, I shouldn’t say “I don’t have the time”. In fact, I often do have the time. It’s not that hard to squeeze in some extra time for someone.

What I don’t have — and what I can’t squeeze in — is more attention. Attention is a far more limited resource than time. So what I should say is “I don’t have the attention”. I may have 8 hours a day for work, but I probably have 4 hours a day for attention.

This summer a guy wrote me out of the blue asking if he could intern for me this summer. His email was great — clear, thoughtful, kind, inviting, confident but not pushy, and not too long (but long enough to say what he had to say without leaving anything out). He was studying at Harvard Business School and was going to be back in Chicago this summer.

He asked if he could swing by and say hi. His email made it easy for me to say yes. So he did, and we had a great session. We spent maybe an hour or so together. I learned about his background, what kind of stuff he was interested in, what he wanted to learn, what he could teach us, etc. Then we riffed on a few ideas. It was natural, flowing, effortless. Really promising.

Then I told him I’d think a few things over and get back to him soon. He checked in a few weeks later, and I said I’d get back to him soon again. And I didn’t.

A month or so after that I wrote him and told him I was really sorry. I’d mislead him — and myself — thinking I had enough time to take on a intern that summer. I wanted to, I really liked him, I thought he’d be great, but I just didn’t have as much time as I thought I had to even consider it more and line up work and spend time with him, etc.

But really, as I thought about it, I realized I had the time. Every day is the same 24 hour cycle. Every workday around 8 hours. Surely I could have found even 20 minutes a day to work with him. But it wasn’t that. It wasn’t that I couldn’t find the time. I couldn’t find the attention.

My mind fills up with a few key projects and that’s it. I’m absorbed by those. That’s where my attention is. Had I made 20 minutes here and there for him, I’m be physically present in that moment, but mentally I’d be elsewhere. And that’s not fair to either of us.

Time and attention aren’t the same thing. They aren’t even related.

We’ve since talked a few more times, and we caught up again last week. I think I’ll have more attention next year. We’re going to keep in touch, check in from time to time as he finished up school, and then try again.