What You Want isn’t Always What You Want

I was sitting on a patio with two of my dearest friends, polishing off a second bottle of wine, when they shared a realization,

“We had always thought we’d retire to our dad’s ranch. But we’ve been spending more time out there, and the people who live there aren’t really our people. We realized we don’t want to leave our home, our community, our friends. Dad’s ranch is wonderful, but it’s so far away from everything we care about.”

I understood. They, like me, are close enough to retirement age that it’s become real. None of us are ready to retire, but when you are thirty, the age of sixty-five is an imaginary number. Then one day, it’s not.

For the last ten years, I have planned to retire to Belize. I realized even if I couldn’t afford a house in the Bay Area, I could afford a cabana in Belize, so I bought one. I adore Belize. It’s a tropical island, and lives up to the picture in your mind; white sand, turquoise water, palm trees… the works. But one way it fails me is the community; the locals are hard to get to know and the ex-pats are the opposite of my Stanford colleagues — poker, sports and fishing are their love languages while mine are books and old wine (fun fact: wine and tropical islands do not go well together. It requires a lot of refrigeration every step of the way.) To solve that, I thought I would create a retreat center on my property, to bring in interesting people.

A couple years ago, I put my cabana on Airbnb. And you know what? I don’t really like being a landlord. As well, thanks to much therapy, I’ve learned my social anxiety is at its worst when I’m in unstructured social situations with groups of people. So my dream of having a retreat center on a tropical island where fascinating people flew in and talked about fascinating things? A terrible idea if I want to be happy.

The great thing is that I didn’t have to build the retreat center to realize it wasn’t how I wanted to retire. By going to my cabana every vacation, I learned I would like to go to other places as well. By buying and renovating the cabana, I learned that construction is a special form of hell. By putting my place on AirBnB, I learned I do not enjoy customer service and chatting with strangers as much as I might have thought I did. I also learned the importance of great property managers. And by attending lots of other people’s conferences and retreats, over time I came to realize that it had to be an event on a topic I really cared about to be worth the stress I had mingling.

Iterate Your Way to Success

In 2011, I was at the Web 2.0 conference in New York. I arrived early for a talk, and sat next to this nice young man and made some small talk. Then he got up on stage and blew my mind. His name was Eric Reis, and he talked about a new way to start a company.

Starting a new company is one of the riskiest things to do in business, for a myriad of reasons. Stats vary, but most say 90% of them fail. As Eric was working as CTO at his startup, he also took Steve Blank’s famous Haas Business School class on new ventures and learned about mitigating that risk.

Steve’s motto was that there are no answers in the building. By that, he meant you can’t get data to build a successful startup by sitting in your office thinking. You had to go out in the world and talk to customers. To that, Eric added running experiments to test if your business model made sense. Eric’s blogging led to a book, but more importantly it inspired a community that built on Steve’s Four Steps to the Epiphany and Eric’s Lean Start Up.

The Lean Startup transformed business the way Agile had transformed software development and Design Thinking transformed product development. If I were to break it down, I’d say the big idea is

1. What you think isn’t always what’s true. As Helmuth von Moltke said of war, “no plan survives first contact with the enemy;” no business plan survives first contact with the customer. So what should we do about that?
2. Identify assumptions. The first time I ran into this concept was at the Lean Startup conference in a talk by Laura Klein. In this talk she showed how to collect your assumptions and map them to a 2×2 that filtered them into “company killing vs annoying” and “we have no clue if this is true vs we know it’s true.” Later David Bland would refine “Assumption Mapping” into a fine art and followed up with an approach to testing those assumptions.
3. Test your assumptions in the fastest, most lightweight way possible. You want to reduce risk cheaply. Unlike academia, which seeks a verifiable truth, you mostly want to quickly learn where you are crazy and where you are crazy like a fox. MVP, or minimum viable product, is how most people think about this, but why build a product when you can do even less to learn even more and increase your likelihood of success a hundredfold?

There is more to Lean than this (and if you haven’t read the book, trust me it’s still highly relevant) but this very simple 1,2,3 approach has an outsized effect on a business’s success.

What if it had an outsized effect on living a happy life?

1. We may know when we are happy, but we suck at predicting what will make us happy. (yes, there is a big assumption there: we know when we are happy. Let’s set that conundrum aside for another essay.)
2. Big life changes are risky. What assumptions hide behind our desire to make big changes? If we can list them and test them, we reduce the risk upending our life for nothing.
3. What is the smallest possible test we could run to test those assumptions? And I mean small. A class. A chat with a friend. A job interview. Volunteering.

From Misery to A Life with Meaning and Joy

Here is another example of iterating your way to happiness: In 2012 I rage-quit Zynga. Really, I rage-quit the entire tech industry. I was burned all the way out: insomnia, acid reflux, depression. After some spending time traveling then watching so much food TV, I turned to the classic strategy of laying on the floor looking at the ceiling trying to figure out what I was going to do with myself since I did had to get back to earning money. My people, this doesn’t work. As Steve said, there are no answers in the building.

But because I had been part of the Lean Startup movement from almost day one, I started forming some hypotheses.

I like food. I am a great home cook. I thought, maybe working with food will make me happy.

I was futzing around on the internet and found a “serious amateur” program that was six week long and was literally the first six weeks of culinary school, after which you can stop or keep going. A perfect test!

I knew that being a chef was often poorly paid, long hours and required being part of a quasi-military often abusive system but I also knew there are variations like private chef that can allay some of those issues. I wanted to test a key assumption: would I even like cooking full time?

The answer was no. I adored learning about cooking and upping my skills, but I was in agonizing pain from the sheer physical labor of being upright cooking for six hours a day (and yes, the hours are even longer when you cook full time.) At the end of six weeks I knew I was not going to cook for a living.

Next, I thought, what about a food startup? I found a gig consulting for a lunch delivery start-up. Since it was a marketplace that dealt with restaurants, professional kitchens and business consumers, it gave me a fabulous look at both sides of the market. I discovered that the margins are so slim in food that if I stayed in any food business, I’d lose my love of food. I really didn’t want that.

There is a saying in Lean: pause and decide if you should pivot, persevere or perish (i.e. shut the company down.) As you test assumptions, you gain new data. That data is a message. Sometimes it means, keep going. Sometimes it means you need to change something. Sometimes it means you are doomed.

At this point, I walked away from professional food. Cooking is a wonderful hobby. So what would I like to do for a living? New hypothesis: what if I taught? I’d run a lot of workshops at tech conferences, and I enjoyed them, so would I like teaching?

I stayed Lean. I did not go back to school to get a PhD in education. I reached out to my network, and found a gig teaching a night class on UX at General Assembly. I liked it. I learned a lot about how to be a good teacher and how it is NOT like running a workshop.

I taught the class again. It got better. I taught it with a co-instructor. Didn’t like that as much. Was asked to teach a two month bootcamp, teaching 8–10 hours a day. Did NOT like that. Swore never to work more than 40 hours a week ever again.

More Small Experiments

Now I had another pause and ponder moment. I liked teaching a lot. I love adult students. I didn’t love teaching in a startup environment.

I reached out to my network again, and got connected with the then-chair of California Colleges of the Arts interaction design program, Kristian Simsarian, who was kind enough to let me teach one elective. Meanwhile I started writing a book (as a series of blog posts first, natch!)

I spent four happy years at CCA, eventually teaching a full load of courses and writing three books. I didn’t run an ultramarathon, but I also didn’t have any back pain. I’d used the principles from The Lean Startup movement to iterate my way to a better life.

And then, I got a call from my friend Julie about a job opening at Stanford….

(to be continued.)