The view looking back at 30+ years in tech: Lessons on 'collecting' the dots

From where I stand today, with 30-plus years in tech (early Apple, Facebook application development, Google, and entrepreneurship) I see a few “dots” that, now connected, are worth calling out. You can only connect the dots, Steve Jobs said, when you look back: the patterns seem elusive as you look forward. Here’s what he actually said (in his epic 2005 Stanford commencement address):

You can’t connect the dots looking forward.

You can only connect them looking backward.

So you have to trust that the dots will

somehow connect in your future.

You have to trust in something:

your gut, destiny, life, karma, whatever.

Because believing the dots will connect down the road

will give you the confidence to follow your heart,

even when it leads you off the well-worn path.

I agree. But with a twist.

This story is about how to recognize your dots and increase the probability that they’ll connect in the future. Better yet, that they’ll connect in a way that gives you pride, satisfaction, and a sense that you’ve aligned with your dreams.

It’s what I call “collecting the dots” and to illustrate it, let me take you back in time. All the way back to 1976, the year I graduated from high school. I may meander a bit as the story unwinds, but trust me. You may collect a few things along the way that maybe you can connect into your own dot pattern when you reach the end.

Here goes.

The world was a very different place back in 1976. I went to an all-girlshigh school in a quiet agricultural community. It was in San Jose, now the heart of Silicon Valley, but I remember it as a land of cherry orchards, wide open spaces, and quiet Eichler-lined streets. As I said: the world was a very different place back then.

Mine was a parochial school, taught by nuns. We wore blue plaid skirts that covered our knees and any top we liked as long as it was grey or white and closed at the collar. The school had high academic standards but also taught classes in “Christian Marriage,” one of two classes that severely burdened my GPA (more on the second one in a moment).

If I recall correctly only a small percentage of my ’76 graduating class went on to college. Yes, much has changed since then. Today my alma mater is an exemplary college prep that cultivates independence, confidence, and potential in its students. But back then our alumni were as likely to get married in the four years after graduation as they were to earn a college degree.

And “going to college” wasn’t a given in my family or even, then, in the culture of our community. External messages pointed me, a good and ambitious student who had worked part-time throughout high school, at getting a job. In my case, input at home pointed me toward “becoming a secretary” as my path to a successful career.

It had worked for my mother. Why shouldn’t it work for me?

I wasn’t much of a rebel but in this I rebelled. I refused to learn to type. Typing would have made it too easy to say yes to the income and security a secretarial job would have provided once I finished high school. In my situation, going to college meant going it alone: my parents made it clear that if I went away to school I’d be on my own.

Looking back, I suspect that my parents disagreed on this. One of them wanted to support me in building toward something bigger by getting a degree; one did not. Whatever the case, the outcome was this: if I chose to continue my education, I would do it on my own. And take the risks of defying, at least with one parent, what was expected of me.

But I couldn’t imagine myself doing what my mother had done: sitting quietly and nodding my head as I took notes in some office somewhere, typingup a tidy well-spaced letter for some executive to sign. I rejected this fate by refusing to learn to type.

I didn’t score points at home or school by deliberately botching my typing tests. I didn’t care. I wanted to fail. I was scared about this unknown of college and the accountability it demanded of me. But I was more scared of caving to the pressure I felt to sign up for a nice little job as someone’s notetaker, an easy way out that would sooner or later close in on me like a shrinking little prison in which I saw myself forever trapped.

So I did college on my own, financially and otherwise. I know that seems harsh now, but it wasn’t really as dramatic as it sounds. Education was less expensive then; I could never sustain today’s tuition with a student’s part-time job. Paying for school was one thing. What felt harder was another price I paid for it: turning away from the support that came along with following a script other people had for me. But in a way I didn’t have a choice: somewhere inside I knew I was allergic to that script.

Looking back, I’m not sure how I had the confidence to go out on my ownway back then. But I’m incredibly grateful that a voice inside somehow overpowered the messages that came from the external forces: those that said they knew what was best for me. Had I listened to them, I would not have shaped the stories, friendships, and experiences that are my richest bounty today.

LESSON ONE: LISTEN TO YOUR INTUITION

So that’s lesson one in collecting the dots: pay close attention to what you feel inside. Even if you don’t hear it now, keep listening. We get so little reinforcement for following it that its voice can become very quiet. But keep listening. It will come back.

A way to start is to become aware of the tension that arises when external messages – all of the things you “should” do, the tests and proofs you’re told you need to achieve –leave you feeling anxious. That may be because those messages conflict with what your instinct tells you is right. Even if you need to follow those external directives (sometimes in life we all need to)listen, closely, and learn from what gut tells you about them.

Steve Jobs weighed in on that, too.

Your time here is limited,

so don’t waste it living someone else’s life.

Don’t let the noise of others’ opinions

drown out your own inner voice.

And most important, have the courage

to follow your heart and intuition.

Somehow they already know

what you truly want to become.

LESSON TWO: WATCH THE PATTERNS

As I look back on my life so far and the things that I’ve loved or been drawn to, I see some recurring themes. I’ll bet you have too. If so, keep an eye on those. Whether they show up as blips on your radar or soul-pounding desires that keep you awake at night, they are the whispers (or shouts) of your true purpose.

For some people they’re generic things: helping others, “making,” seeing better solutions to the problems that surround you. For others they’re more specific: composing music, soldering circuit boards, caring for people with special needs. Starting a company. Trying to change the world.

Often, these things don’t get a lot of reinforcement in the usual feedback loops at school, work, or everyday life. They may not help us earn a living or even point to a way we might spend our job.

That’s ok. Simply pay attention. Those voices are hints and clues that will emerge as dot patterns as your life journey continues to take shape. Trust me: over all of my life I’ve watched this happen.

My dots include creativity, geekiness, trusting my gut, and the ability to bridge business strategy with emotion and art. I guess they’re all kind of the same: creativity + geekiness has created an art-business bridge, one which felt obvious to me even when others didn’t see it. In fact, my “grok” of that connection often left me feeling like an outlier at best, an outcast at worst.

Yet it seems the things that got the least reinforcement in my younger life (they often drew negative feedback) have proven to be the qualities that have served me best over time.

Funny and ironic how that works.

We all learn not to trust our gut. It has to do with the way we learn and the external messages that shape our brains and outlooks in our early years, and then keep on shaping us. We hear well-intended messages like, “This is how you need to do it.” “It’s always been this way.” “Don’t reinvent the wheel.” “Go with the flow.” “Everybody does it like this.”

You’ve heard all of those too, right?

Sometimes we do have to go with that flow; it’s not worth the stakes to resist or rebel. But pay attention to how you FEEL when you do conform. If your intuition tells you to do one thing but you do another, become a master of noticing that and being mindful of the tradeoffs.

I haven’t always chosen, or been able, to follow my gut. Yet as my story will show, the times that I did have almost always brought me closer to the life I wanted to lead.

But back to that other stuff. I loved art, but I was also drawn to business. I saw a way they fit together: how art was a language, a wordless form of communication – one that had voiced mass movements and the key messages of society over time. Business, I saw, looked to connect with (and even become part of) those movements: that’s how products became relevant to customers.

I studied art, completing nearly a full major divided between studio work and Art History. And I studied business, loving all of it besides the finance and accounting coursework, which somehow made my eyes cross. I petitioned several times to blend the business and art, trying to convince my advisor that my Art History coursework contributed to business thinking so I could apply some of those units to my business degree and avoid some of the accounting classes a straight-up business major required.

It didn’t work. But I kept trying. I nearly lost faith, too. There must be something wrong with me, I thought, to think these two things are connected. Nobody else sees it. They must know something I’m missing. Maybe if I do it their way I’ll figure it out.

Know the feeling?

At the eleventh hour, though, right at the moment where my advisor’sfinal “no” would have cost me an additional semester of college, he relented. I’d probably worn him out. I don’t think he ever saw the connection, but when I graduated with a Liberal Arts degree in “International Marketing,” one that melded business strategy with an understanding of art, ancient to modern, I knew inside I’d gotten it right. I’d learned to “think different.”

I left college with a unique way of seeing the world and with something of a conviction that if I stuck with it,it would somehow serve me right.

Trusting my gut about that fit, something others didn’t seem to understand, has yielded innumerable benefits, not to mention deep enjoyment, over the years.

Looking back, I was collecting dots that my intuition told me were right for me. Over the years, these have been the dots that have shaped some of the best connecting points of my life.

But it wasn’t always easy. I know, absolutely for sure, that I lost quite a few consulting gigs when I was self-employed (from the early ‘90s until 2008) because I talked about things like design, emotion, and visual thinking in meetings with tech founders and CEOs. Sometimes I questioned myself: why was this important to me when all of these other smart people in the room didn’t see the relevance?

Sure, sometimes I accepted consulting projects where I didn’t use that internal spark of art and creativity that fueled me. But I felt flat and undifferentiated in those projects, and looking back it wasn’t the work where I had the most impact.

Funny: looking back, the clients who wouldn’t make room for creative thinking or design-driven inspiration back then largely aren’t around now. If they are, they’re “holding on” – not that different from how they were back then. Or they’re chasing other companies who have eclipsed their success.

+1 for trusting your gut.

LESSON ONE, REMIX: REALLY…TRUST YOUR GUT

But when you’re young you often think the things that are different about you are flaws or shortcomings. As you get older, if you watch closely, you’ll see that your outlier traits are actually your superpowers. Those things you know innately without anyone having to tell you or teach you turn out to be the talents that get you ahead.

That’s a bit of a tangent, but the takeaway is: if you’re passionate about something, believe in THAT at least as much as you believe in the external forces who tell you it doesn’t matter. There’s at least a chance that what you have is more relevant than what they believe.

LESSON THREE: CREATE YOUR LUCK

I was lucky. I had a great validation of the importance of trusting my gut and aligning with the power of art very early in my career (in 1981, to be exact, when I was barely 23). That lesson has influenced nearly everything about the path I’ve followed since then.

After I graduated with that hard-won degree mycarefully planned next steps went awry. That International Marketing major had poised me to find an internship in Brazil, and I was lined up to head there for a year-longproject shortly after graduation.

But a few days before my trip, out cycling with some friends, I was hit by a car.The accident was serious enough that I needed to move home to my parents’ house, back in San Jose, to recover. Just what every college graduate wants, right? My passport and unused one-way ticket collected dust on a bookshelf while I grew increasingly frustrated, impatient to get better and return to my plan.

One day, when I was almost back to normal, my father dropped the San Jose Mercury News classified section into my lap. He told me I needed to get back on my feet, figuratively as well as literally, and find myself a job.

“Forget Brazil,” he told me. “Your accident was a blessing in disguise. This place is changing. This computer thing is getting big – there’s a new building going up every day here. One of those companies is going to be smart enough to hire someone like you.”

Lesson number something, in fine print: you should listen when people who love you are actually right.

I took his advice. Dutifully scouring the classifieds each day, I sent my resume to every appropriate company I could find. And I promise you that each of them sent me back a rejection letter. I was collecting 5 or 6 of them from my parents’ mailbox each day. Sometimes it felt like more rejections came in than resumes went out. It was a glum and discouraging time.

I saw a posting for a secretarial job and considered sending in my resume for that. “Get your foot in the door,” someone told me. “A year or two out you can ask for a promotion.” I actuallyconsidered it. That’s how bad it got.

Then one day as I sorted through the stack one envelope stood out. Unlike the others in the stack, this one had a bright six-color rainbow of an apple on it, and a san serif font reading “apple computer.” Color! So different from the dull grey or black flatness of the other envelopes. An image from reality! That stood right out from the meaningless grids or blobs next to other company’s names. And a friendly font with a familiar name! What a difference from the strange syllabic mashups of these other companies, odd tecchie-sounding names that I didn’t understand.

I opened the envelope, eager – only to find my hopes dashed. But instead of sliding Apple’s rejection back into the envelope and adding it to the growing stack I’d received over the last weeks, I felt something inside me click into action. This company was different, I thought. They understand the power of design, of color and style, how that ignites something in people’s spirits. They’re thinking about how their logo communicates, not only about what their company does.

A company that thinks like that, I thought, is going to understand how art fits in to business. And a company that understands that, I hoped, might be a good place for me.

LESSON FOUR: WHEN YOU KNOW IT’S RIGHT, DON’T WAIT. ACT.

I did something that day that I hadn’t even considered doing before. I dialed the phone number on that apple-embellished stationery and asked the operator to connect me with the person who had signed my rejection letter. When she picked up the line, I heard my own 23-year-old voice telling her she’d made a mistake.

Lucky me. She listened. And once she did she said, “Well, there is this one thing…” She told me about an opening for a Communications Specialist in the intercontinental marketing group.

A week later I started at Apple.

Apple was my home for nine years, until I left full-time work (and Silicon Valley) as a young mom in 1990. For the 18 years that followed I worked as a consultant, aligning technology companies with increasingly creative, human, and visual ways of expressing their brands. More and more, I helped companies, powered by the rise of the web, connect the dots between their products and their audiences through the power of design. This work ultimately led me back into full-time work – I joined Google in 2008 – and after that into the more entrepreneurial work I do today.

LESSON ONE, REMIX REMIXED: REALLY TRUST YOUR GUT

I believe that each of us are born with a unique set of gifts, of superpowers, so to speak, that set us apart. These are the things that help us see things in unique ways, make unusual associations, see patterns, and generally “think different” about the way the world works.

But little in society aligns with the nurturing of those unique gifts. In fact, few of society’s systems – school, for sure; often community, sometimes even our families – are optimized for encouraging our differences. The opposite: their jobs (our teachers’, our coaches’) get easier when we smooth down our spikes and level ourselves out to be more like everyone else around us.

My superpowers often felt like my biggest challenges. They weren’t always abilities that won me approval or contracts or sometimes even popularity: especially as a woman, I am sure my geekiness and ambition rubbed some people the wrong way.

But as I look back after the course of my life they’ve been the forces that most favorably shaped my ability to find and enjoy some excellent work opportunities – and above all find satisfaction in doing work I know I was meant to do.

As I think about the years ahead, I see these strengths taking things to a whole new level. I don’t question them any more; they are the foundation of my life journey, my story so far. Time and again they’ve proven that they somehow know what’s right for me, even more so than I might know myself. Watching what shapes success over my thirty-plus years in tech, I see the correlations between how well people align with their true purpose and the way they attain success (on a whole lot of different levels).

No, I didn’t see how my dots fit together as I began collecting them years back. But I noticed something different about certain things. They were the forces in my life I couldn’t ignore, that I had to align myself with. In retrospect, those were the early glimmers of a dot pattern that, looking back, maps the framework of my life.

If I were you, I’d start paying special attention to those dots now.

LESSON FIVE: IT’S ALWAYS A NEW BEGINNING

Seeing how those dots fit together today inspires me to keep collecting, and connecting, as I move ahead.

At this point in my life, I see clear patterns in the way certain themes have recurred and certain experiences shaped my journey. Hindsight, as Steve suggested, does have a way of giving us perspective. One I’d like to share is this: I’m going to pay even more attention to my gut and align myself even more fully with the recurring themes as I go along.

In other words, now that I see the patterns, I’m doubling down on them. I’m convinced they’re guiding me to my true purpose and intention.

In fact, I’m going to use the “dots” metaphor as a way of guiding decisions, especially at this point in life where focus and impact are so important. “Is this a dot I want to collect?” I’m actually asking myself that. If I don’t want it to be something that will guide and connect to future dots, I’m going to be careful about my decision. Time is always precious. For me, more so now. And everything that has brought me to this place so far is the place, now, where I begin again.

That will be true at every moment. So collecting wisely is key.

Look to your dots. Listen to your gut, to your heart, to your wisdom, or to whatever voice inside whispers straight to you, even when it says things that are very different from the voices you hear outside. Maybe as you begin again, today or tomorrow or ten years from now, you’ll hear in those whispers the voices of things you’re willing to work for, take a chance on, even pick up the phone and talk with a stranger about. If so, listen closely. Those may be the voices of the dots that will shape your truest and best life story. And those voices, I’ve found, are often the things that give you the best result.