Fighting History

One of my major regrets is that I didn’t start a business in 2002. To be more accurate, I did start a business. I had an idea, built a prototype, went to SCORE mentor meetings, met with a great lawyer and filed paperwork. My site was getting visitors, I was getting emails from those visitors, and initial feedback was outstanding. My family, instead of being supportive, expressed concerns. Worry. Doubt. I felt their doubts creep into my head and take root. I got scared. Maybe they were right. What was I doing? I unwound all the work I’d done and put my head back down to blend in with the crowd.

I never forgot what my lawyer said when I called him to dissolve the corporation:

“If you spent as much time working on your business as you spend worrying, you’d already have revenue.”

I was young. I was far less mature than I am now. And I don’t blame my family; I blame my own reaction to what they said. I didn’t want it badly enough. I didn’t know what I wanted.

For the next 12 years, I wished I’d started the company.

This week was tough because it echoed history. I shared some good news and got back anxiety. Worry. I know it wasn’t intentional; in fact, my family has been incredibly supportive of my efforts this time around. But nonetheless, I spent the end of the week replaying my worries, reminding myself why this time would be different. Fighting my own shadows. It’s not a feeling I’m used to anymore, and not one I enjoy.

I didn’t give in. I’m different than I was. I’ve defeated far worse than some unformed doubts, and I know that the regret of never trying is more powerful than fear.

But I could use a spa. And chocolate. Possibly some flower petals and essential oils.

Existential Roller Coaster

This week I’m riding an existential roller coaster. One day I feel great, the sun is shining, response to my stories and ideas is sizzling, compliments flow. I feel loved, at peace, my arteries unwind, my heart beats steady and I know why I’m here.

Another day I feel disconnected, bombarded by worries over shadows and trapped in my own mind, struggling to make forward progress. Wondering why I’m doing this. Feeling alone.

I knew I would feel this way sometimes when I began this journey. I was prepared for down days and fears, and I don’t let them dissuade me like I once did. This is progress. I used to live in fear.

But I tried living in fear and it does not work for me. It’s like creating a defensive sphere where days are only ever perfectly pleasant: a hazy blue sky, a light breeze, an occasional shower. No gusts of wind, no hailstorms, no lightning challenging anything; but also no brilliant sunsets, no rainbows, no breathtaking views.

I prefer life outside of the sphere. I have time to enjoy life and explore it. This is a blessing. Most days I’m thankful, ready for adventures and the good and bad they bring with them.

When gray days get me down, it’s hard. It’s hard to stay focused on doing good for others and making useful contributions to the world. It’s also hard to enjoy each moment, even though I know each one is valuable and each person I care about is priceless.

It’s a tough balance. It’s a practice, an exercise, waiting for the next sunrise.

But it’s worth it.

Active Participation at SXSW

I’m at SXSW in Exhibit Hall 5, waiting for a presentation. I’m sitting in the second section of seats, next to an aisle and near enough to a door for easy exit, if I’m not enjoying myself at any point. I have a great view of the speaker podium and the big-screen TV where the speaker will be projected in larger-than-life. I’m thinking about the fact that I always choose this seat.

It has a great view of all the action, but it’s not really in the mix. Not pressed by crowds, not irretrievably committed to the event. It’s a perfect snapshot of my old life — the one I left behind. I’ve spent much of my career in the background, reluctant to take the spotlight or make a no-going-back move. I like to leave my options open. This seat perfectly reflects that.

In the last nine months, I’ve done the opposite: left my job, left my lease, left my stuff and committed to a major change. I’m creating things and pursuing them to their logical end. I’ve abandoned the easy-out approach to life and decided to give this period of time all I’ve got, so I’ll never feel like I didn’t try. So far I’ve done a lot and learned a lot, and I can feel this accelerating. I’m hitting the gas pedal harder, not the brake.

But I’m still sitting in this seat. Why? I promise myself, for the rest of the conference, that I will sit in the center, in the mix, and make myself part of the event instead of observing quietly. I intend to get the most out of this, too.

San Francisco in the Prehistoric Age

I found this ancient essay I wrote for Derek Powazek’s site about visiting San Francisco in 2001, just after the recession devastated the city’s economy. I’d spent a summer there five years earlier, so I wandered around for the weekend noting contrasts and taking notes.

SF Stories (my post is the long one at the top)

I find I can’t conjure that depth of feeling for the ways L.A. has changed in the past decade. It’s different, and I could write about it, but not with so much melodrama.

Carless in L.A. and Loving It

I decided to try Medium again. Here is my second post on this beautiful essay site:

I Have No Car in L.A. and It’s Awesome

I’m not sure how it’s going to work for me, but I’ve found a publication I like there and I love writing in their interface, so I’ll probably do it from time to time.

TL;DR: I decided to use Uber and Lyft instead of renting a car in L.A. It rocks, even in Car City.

The Art of Imperfection

I took art classes in high school with an amazing teacher. Several of my classmates became illustrators.

I didn’t. I studied journalism instead. But I never forgot the most important lesson from Mr. Hess.

I messed up an art project during my senior year. I’d spent weeks outlining a harbor scene in pencil, then shading it in colored pencil, and I’d just done something immensely stupid. I zig-zagged a dark red pencil across the sun’s rays because I wasn’t paying attention. It was ruined.

Mr. Hess didn’t seem upset. He was zen calm. “Just keep working on it,” he said. I tried to explain that it was a waste of time to keep working on it, because it was ruined. He wouldn’t listen.

“Find a way to integrate it with your artwork,” he said.

I didn’t want to integrate it. It was a mistake, that giant red slash, and I wanted to go back in time and remove it and have my beautiful sun rising over the ocean, serene and perfect.

That was impossible. So I sat down in a chair and picked up my pencils and tried to figure out what the heck to do now. I started doodling around with the red slash, tracing a pencil lightly over it. I shaded a nearby ray darker, the one most affected by the slash, until it was nearly red. I traced some letters into another ray of the sun, erasing where I could and blending where I couldn’t.

In the end, my art project won an award at the year-end show. It was much better than my initial, bland vision of a serene sun rising over a serene sea. It was a chaotic scene, with dark orange and red and yellow rays alternating, and messages engraved in them spiraling out toward the edge of the canvas.

Mr. Hess was right. It’s impossible to mess up an art project if you keep working on it. Even if you tear the paper in half, that’s just a new starting point. You always arrive at another place. Sometimes it’s better. Sometimes it’s worse. It’s life. And it doesn’t become great through perfection and planning.

Life Lessons for My Younger Self

I’m a bit late for the New Year, but here are things I would tell my younger self. I got some of these right and some of these wrong. I’m still working on some of them!

Get health insurance. Having the worst-case-scenario covered allows you to take greater risks.

Get disability income insurance. You may need it someday, and when you can no longer get it, you’ll be grateful that you already have it. See above re: covering the worst-case scenario.

Don’t major in something impractical, unless you double-major in something practical.

Don’t go into student debt. It will constrict all of your life choices. Top colleges will pay a large part of your tuition if your family’s household income is below a certain threshold. Try to get admitted there. If you don’t, go somewhere cheap and supplement your learning with free online courses.

Be self-motivated in your work and education. No one else will make you be successful.

Start a company while you’re in college. As long as you don’t flunk out, this is a virtually risk-free option on your future.

Learn to program. It’s the lingua franca of the 21st century. Learn how to explain what you’re doing to someone who doesn’t know how to program.

Learn to write. It will serve you well in any career.

Learn to sell. Many unknown artists were just as talented as the famous ones. Maybe more talented. But does anyone care now?

Even when you don’t think you’re selling, you’re selling.

Most people are bored most of the time. Try to make their day a little more interesting, and you’ll be a great presenter.

Understand that the five minutes you spend stopping by someone’s office to say hi are more important than the five hours you spend on a presentation that no one sees if no one knows you. Human connections are the heart of LIFE. And of business.

Have compassion. Allow the possibility that the only difference between you and someone else may be circumstances.

Don’t be afraid to love. In the end the people you love, and the people who love you, are one of the most important things.

Do something important if you feel the urge. This is the other most important thing. Don’t permanently suppress your desire to do good to fulfill your desire for money. With persistence you may be able to have both.

Don’t put everything on Facebook or your blog. There is no “I Forget” button.

Keep a little bit of yourself to yourself.

Be generous with your time in helping others, but stay focused at your core.

You can do a lot of things one thing at a time. You can’t do everything at once. Multitasking is bullshit. Procrastinating productively, on the other hand, is not. A second project can help you complete both projects.

Sleep the number of hours you need almost every night. It makes you more productive and often happier.

Don’t eat crap. In the U.S., most processed food, meat and dairy are crap.

Give thanks for who you are and why you’re here. Then get it done.

Don’t give up easily. Keep at it until you solve the problem, for as long as you feel you can solve it and a little bit past that point.

Listen to yourself, not other people, on the decisions that really matter. Taking a job to please someone else is never a good idea.

Don’t do risky things that aren’t worth the trade-off (motorcycle riding, if you’re a neuroscientist).

Jump bravely into low risks that are masquerading as high risks (leaving a job to try something new, investing during a market crash, telling someone how you feel about them).

You can be yourself while still learning who you are. Just be willing to adjust as you go along.

Creativity and persistence combined are the greatest force on Earth. Use them well and wisely.

Los Angeles, Again

Apologies for my absence from the blog for the past few weeks; I spent the time immersed in Udemy, getting my new course ready for publication. It’s submitted for review now, waiting only for an image before it gets set live. I’m super-excited and will let you know more when it’s released.

I’m spending the winter in Los Angeles.

I promised myself last winter, as I was freezing in my NYC apartment with the heat cranked up to max and my poor tree actually leaning away from the window to escape the polar vortex (who knew trees even DID that?), that if I actually went ahead and pursued this plan to travel and learn and find a new path, I’d spend the winter someplace warm.

I chose L.A. I’ve lived here before, for four-plus years in the early 2000s, and I know where to go, where to avoid, where to relax, where to hike. Most of all, I have friends here who I’m looking forward to spending time with, making the city feel more like a village hamlet or a reunion than a sprawling sprawl.

I’m already feeling the pull of L.A.’s unique rhythm, the blend of seasons into endlessness, the no-hurry mornings and the bright blue perfection, though now I am uniquely qualified to fight it with productivity. I spent the last seven years in New York, where busy-ness is a way of life, even when it’s fabricated.

I remember traveling around L.A. when I was working in journalism, wondering as I passed by cafes in the middle of the day, “Who are all these idle people?”

Now I am one of those people. But I’m not idle. In the past month I’ve doubled down on my (now-working!) Xcode plugin, signed up to present it at a SXSW breakfast, added new capabilities and started planning a standalone software product; created a Udemy course to teach basic programming concepts to would-be programmers, non-technical co-founders, and parents and teachers; and fixed major bugs in my flashcard app that were preventing progress. I’ve spoken with a lawyer about creating a company and am prepared to move forward.

I expect to launch all of these projects by the time I leave in March, along with an organic food finder I prototyped last summer. It’ll be an interesting couple of months.

Then I’ll see what sticks.

In the meantime, I’ll enjoy being productive in the midst of laid-back L.A. I’m also trying to get back on track with my organic, hack-your-health lifestyle, which I decided a few years ago was non-optional if I wanted to live an optimal life. It’s super-successful for me when I’m on-board with it, so I’m back on board and ready to enjoy my (non)-winter.

73 degrees. I love it. Lots of work to do.

Nothing Is Perfect: The Less-Good Parts

''The Mouth of the Beast'' from by {{cc-by}}

”The Mouth of the Beast” from by {{cc-by}}

One of my favorite people told me I sound like a superhero. The blog highlights all of the great parts of leaving my job and wandering the world, but none of the snags or tangles along the way.

I’m not sure I entirely agree. I’ve highlighted some of the ambiguous moments, like feeling stranded in Tuscany without a car, struggling with Internet outages and unreliable trains, and getting used to dark nights in farmhouse country. I’ve written about fear.

Partly, I’ve shied away from ungood stories because I don’t want to sound like I’m whining or ungrateful. On balance, this whole endeavor really is pretty great, and I’m happy I did it. I’m also grateful I was able to do it.

But to balance the scales a bit, this post will cover, in an anonymized way, several additional things that weren’t perfect.

1. Cat Bite, Initial Encounter. That’s what the hospital paperwork said when I was released from the emergency room. My roommate’s cat, which hates people but liked me, didn’t like it when I took her photo with my iPhone. It looked like a tiny scratch, but it got infected and my arm turned red. Seven days of antibiotics and stern warnings from my doctors to take all of them. I did.

2. Other Guest Roulette. With Airbnb, when I rent a private room in a host’s apartment, there are always other guests at some point. This has been true 100% of the time so far. Some of the guests were also from Airbnb, and some were friends of the host. Several of the guests were awesome and we became friends; others were less awesome. Only one made me feel truly uncomfortable, mainly because the hosts were also out, but we shared space for just a day and I locked my door while he was there.

3. Type-A, Nature-Lover Shock Therapy. I discovered I may not be cut out for life on vacation. That’s fine; I didn’t think I wanted to spend my life on vacation anyway. But I had more trouble than expected when I stepped away from an always-on, Internet-focused life. It was good for me to have this experience, but it wasn’t as easy or relaxing as I thought it would be. There were also beetles in the farmhouse that made a low, humming buzz that sounded like giant wasps. This terrified me until I figured it out.

4. My Right Foot. I sprained my ankle about 10 days before my scheduled flight to Florence. It wasn’t a bad sprain and didn’t hurt much, so I never bothered to ice it much or use a compression bandage. But I re-sprained it two days pre-flight; it collapsed while I was just standing still (perhaps a bad sign).

It still didn’t hurt much, so I purchased a compression sock and flew to Italy, then ended up visiting the ER the night after I landed. It turned out to be fine, thankfully, and the total bill was 31 euros. A week later, I re-sprained it again in the Cinque Terre, because I was starting to feel better and saw a hiking path near the water that I really wanted to explore. This time was worse — I felt like there was spaghetti in my ankle instead of ligaments and tendons. I finally accepted the need to take it easy. (It is getting better now, fingers crossed — I’m getting SCENAR therapy from my amazing acupuncturist and it is essentially a miracle.)

5. What Now Syndrome. My greatest fear is that I am like a zoo animal that, released from its pen, stands in the middle of a field and doesn’t know what to do. I can do anything, so I do a little bit of everything, and therefore I do nothing. I feel this fear more acutely as the learning-and-exploring phase of my adventures shifts into a do-something phase. I don’t think it’s bad for me to try several different things, and I think as long as I do some real work every day, I’ll figure it out, but it’s easy to feel overwhelmed by possibilities. I woke up this morning from a dream that I won’t be happy unless I’m working hard. I already knew that. And I woke up happy and ready to work.

I can’t help it even now. I’m turning this “Nothing Is Perfect” post into an “Isn’t This Awesome?” post. That really is how I think about the world. But nothing is perfect, and I’ve tried to give you a glimpse of that, to round out the picture and add more humanity to this adventure story.

My Interview with Nomadtopia

I’m excited to share the interview I did with Amy Scott at Nomadtopia: It’s here.

In the interview, I share some of my best advice from six months of travel, learning and exploration, including how I test-drove my nomad plan before taking the leap.

I normally have long blog posts, but this time I’ll let the interview speak for me, and I’ll be back with more later.