I spend most of my time listening to Dharma talks and following guided meditations.  Dharma talks are typically 60-minute talks that are about self, subjects ranging from fear to death to love and joy.

A huge repository of dharma talks are available here: dharmaseed.org.  Click on “talks” and either view the most recent talks (there’s an RSS feed, too), or search for things like “forgiveness” or “difficulty” or “love,” whatever you’re interested in hearing.  These are talks about life and self, and they’re very interesting perspectives.  They are not meditations.

There are good, free guided meditations at the UCLA Mindful Awareness Research Center.  Jack Kornfield has wonderful guided meditations for sale, too.  I very much enjoy meditations on loving kindness, forgiveness, breathing, awareness, joy, and working with difficulties.

What I tend to do is meditate 2-3 times per week, for anywhere from 5-45 minutes each.  I listen to a Dharma talks on the bus, car ride, or while working out.  The Dharma talks provide the perspective, and the meditations are like lifting mind weights that produce happiness instead of big muscles.

There’s a story about a group of people climbing to the top of a mountain.  It turns out it’s pretty steep.  And as soon as they get to a certain height a couple of people look down, notice how far it is, and completely freeze.  They had come up against their edge and they couldn’t go beyond it.  Their fear was so great that they couldn’t move.

Other people tripped on ahead, laughing and talking.  But as the climb got steeper and more scary, more people became scared and froze, too.  All the way up this mountain there were places where people met their edge, froze, and couldn’t go any further.

The moral of the story is that it really doesn’t make any difference where you meet your edge.  Just meeting your edge is the point.  Life is a whole journey of meeting your edge again and again.  That’s where you’re challenged.  That’s where if you’re a person that wants to live, you start asking yourself questions, “Now, why am I so scared?”  ”What is it that I don’t want to see?”  ”Why can’t I go any further?”

The happy people who got to the top weren’t the heroes of the day.  They just weren’t afraid of heights.  They are going to meet their edge somewhere else.  The ones who froze at the bottom were not the losers.  They simply stopped first and so their lesson came earlier than the others.  However, sooner or later everybody meets his or her own edge.

It occurs to me that my love for adrenaline sports such as snowboarding, snowmobiling, skateboarding, and cycling is based on my desire to find my edge.  I love trying bigger, scarier things.  Even when I fall or get hurt, I love getting back up and trying again.

Knowing you’re capable of doing something, yet putting it off because you don’t believe in yourself. I imagine many of you have been in this position before, just as I have, too.  You doubt your abilities, and you never feel you’re ready to pursue your dreams.  You beat yourself up for what you haven’t accomplished.  You’re confused about your career or relationship and sit around waiting for a change.  Or maybe you don’t even have a career or a relationship and want one badly.  Sound familiar?  What follows is my story of self discovery — the bumpy road that has taken me through a long period of self doubt and into a period of confidence, giving me the freedom in my career to do what I have always dreamed of doing.

Cloudera — My First Job

I feel as though the last few years, from the moment I started my first job up until the time when I quit my last job, I’ve been blocked, unable to reach my full potential in the workplace. My struggle started at Cloudera.  I was a software engineer straight out of school, working amongst the best engineers in the industry, and I didn’t think highly of myself — I wasn’t as good as the other engineers and I let that define me.  Self doubt overtook me like a plague. I blocked myself from my full potential, in part because I was in the wrong role at the company. But mostly because of the negativity I was directing towards myself.

After a year as an engineer I transitioned to do a mix of training, consulting, support, and the like. I was finally in a position where I was very good at my job, which helped my confidence a little. But I wasn’t doing a job I had always dreamed of doing. In college I never saw myself answering support tickets and installing clusters for someone else. I wasn’t on the path I wanted to be on, so I left Cloudera to put myself on the “right path.”  The decision was hard given how much I liked the company and enjoyed my coworkers, who are now very good friends of mine.  But I needed change.

Atlassian — My Low Point

After Cloudera I joined Atlassian as a product marketer.  I took the job because others advised me that product marketing would be a good field for me.  I listened, even though I had a marketing internship in college that I didn’t enjoy in the slightest.  However, while at Atlassian, I learned an immense amount and had a great time, too.  Atlassian is a fabulous company, but I struggled there.  I never contributed to the company in a meaningful way.  I had lots of ideas but found myself getting stuck in the execution of them.  I beat myself up for not making an impact, and still my confidence stayed low.

I recall one specific meeting at Atlassian where my confidence was at an all time low.  I had an awful attitude in the meeting, and as soon as it was over I was unbelievably disappointed in myself.  I was consumed in the weeks that followed by questions about why I reacted that way, who I was, and what I was doing.  Throughout this period of introspection I thought deeply about what I wanted to do, and how I wanted to get there.  I decided I needed to leave Atlassian for the same reasons I left Cloudera.  But this time I left to consult three days a week and experiment with my own ideas the other two, despite the strong efforts of my friends to guide my career for me.

Self Discovery

Something changed when I left Atlassian that I’ll never forget.  Friends and former coworkers were criticizing me for leaving two companies doing incredibly, incredibly well, mostly pointing out the very clear financial incentives for staying at these companies while my stock options vested further.  But I didn’t care.  What changed was that I finally started thinking on my own.  I finally started using others’ opinions to guide me instead of define me.  I stopped looking for approval from others.

For the first time since college I looked to myself for guidance and change, I believed in myself, and I let my heart guide me, paying attention to my feelings and emotions before anything else.  I approved of myself.

I can’t say for sure what changed to instill this new found confidence.  But I think the change came from a combination of three things: my practice with mindfulness and meditation, my consulting experience, and my impatience for being unhappy any longer.  I’ll start by talking about mindfulness and meditation, two practices I started right as I was leaving Atlassian.

Mindfulness and Meditation
Mindfulness and meditation have taught me to observe and study my emotions and feelings.  Now when I get a sinking feeling of self doubt or anxiety, I understand exactly where that feeling is coming from, why, and how it’ll impact me moving forward.  When I’m faced with decisions, I can relate emotions and feelings to thoughts and beliefs.  I’m so much more aware about what is going on, both internally and externally, that I understand my place in the world at a much more fundamental level than I ever have before.

Mindfulness and meditation have also shown me the importance of loving yourself, thinking highly of what you have done and what you’re capable of doing.  Beating yourself up only makes you unhappy and furthers your self doubt.  Negativity toward yourself isn’t productive.  Ever.  We’re each amazing in our own ways, regardless of what we’ve accomplished or what we’ve struggled through.

My Consulting Experience
Throughout my career I’ve had very good bosses, but none of them gave me enough freedom to express myself.  For better or worse I follow an order exactly as it’s given to me, deferring all direction and decision making to my boss, giving none to myself.  But after I left Atlassian I consulted for WibiData, a company founded by two close friends.  I was working from home, by myself, on a project that I had almost all control over.  I felt a sense of freedom that was at first very scary, but which later developed into a sense of confidence as I continued to consult and experiment with my own ideas on the side.  Looking back I wish my bosses would have inspired more confidence in me.  But now, being my own boss, the scary phase of freedom is over and the exciting part is here to stay.

How I Feel Right Now

Working for myself has been a true pleasure.  I’ve finally gotten a chance to pitch to some of the most famous investors in Silicon Valley, and I’ve gotten a taste of what it’s like to start a real company — anything from forming the board to opening a bank account.

But it’s not all fun.  Starting a company is incredibly stressful on many different levels.  First, and most obviously, I don’t have an income.  But the stress manifests itself in other ways, too.  I don’t have the luxury of having a boss to protect me from mistakes or misdirections.  It’s all on me now.

Despite the added stress, I’m still loving what I’m doing, and I don’t doubt myself one bit.  I’ve just accepted that doing something important and exciting will always be stressful.  And without self doubt I never let that stress turn into something that controls me.  I keep going.

Despite the new confidence I have in myself, I still seek advice from others quite often. Although now, instead of doing what they say because I want them to approve of me, I listen to the advice that I agree with.  But I no longer seek approval from them. I approve of myself and that’s all I need.  I do what I believe in despite any conflicting advice from people I respect.

My Advice to You

I can’t count on two hands the number of friends I’ve spoken to over the last few years who suffer from self doubt.  Many of us are in jobs we don’t like, or in relationships that we aren’t comfortable with.  Or maybe we’re not in a relationship or without a career.  We become unhappy with something in our life and we do nothing about it.  We don’t believe in ourselves and we’re blocked from finding happiness.

Overcoming self doubt and finding your confidence won’t happen overnight.  It won’t happen in a few weeks or months, either.  And it won’t come from an external source.  It must come from within.  The process starts when you start believing in yourself, even in just the very slightest way — when you stop letting others’ beliefs about you define who you are and what you’re doing — when you stop seeking approval from someone else and approve of yourself no matter what.

You need to stop waiting around for something to change in your job or relationship.  Nothing will change unless you be the change.

No potential employer or significant other will believe in you if you don’t believe in yourself.

I’ll close with a link to a guest blog post a friend made a few days ago.  This particular friend has changed his attitude, and in turn changed his life.  He quit the job he hated and has since gotten many promising job interviews, which is an accomplishment he’s never enjoyed before.  His story is inspiring in so many ways and I’m incredibly proud of him.  Take a look at his 10 tips for happiness and read the post understanding who wrote it.

And hang in there.  Everyone goes through periods of self doubt, ending only when each of us realizes that we can’t sit around waiting — we’re the only ones who can change our own lives.  And change starts by believing in yourself no matter what.

When I look back at the times of my life when I’ve been the happiest and most excited, I can really only think of a few different buckets to put these memories in:

• Experiences with friends — snowboarding, snowmobiling, cycling, surfing, skateboarding, bar hopping, Burning Man, Bay to Breakers, whatever
• Recalling experiences with friends
• Building or creating things and sharing them with others — software, music, tree houses, anything
• Self discovery by learning from experiences, both good and bad

When I play back these memories I realize that there’s really one commonality.  I am the happiest when I’m doing something I love with people I love, too.  I love being goofy, forgetting that I’m 26 and dancing like no one is watching.  And I love challenging myself, riding my bike for long distances, jumping off cliffs on my snowboard.  Yet none of these experiences are as fun alone.  A fun experience is exponentially more powerful and lasting when others are with you, enjoying the same experience you are.  Furthermore, you can recall the experiences over and over with those same people, which further inspires you to continue to do amazing things and enable those experiences.

For as long as I can remember I’ve tried to answer the question, “How can software make people happier?”  It’s a hard question to answer, mostly because there’s such a broad meaning of happiness.  Etsy funds entrepreneurs in the third world.  Facebook lets me stay in touch with my friends.  Embedded systems in cars and airplanes enable travel.  There are so many ways that software moves us; I just haven’t found the path that I’ll take to make a difference.

I’ve been searching and searching for the answer to my question that rings most true.  And along the way I’ve found many answers that I believe in.  Bret’s talk made me realize that the inventions I want to make are on the principle that people should be happy.  Yet only now I realize a great strategy for helping others be happy.  I’ve been happy for most of my life, in part because of my attitude, but mostly because of my devotion to trying new things and pursuing my interests.  I need to figure out a way to help others improve their attitude, and to help them pursue their interests.  To help them have fun by remembering that adulthood can be as simple and innocent and fun and exciting as childhood is if you let it.  You’ll see what I’m talking about soon :).

1) Procrastination is bad. If you’re unhappy, your state of mind often won’t change without an effort to actively seek change. The days, weeks and months go by and then you might wonder how you’ve endured a situation for so long. Negative emotions build over time and you may feel increasingly trapped. Taking control of your situation immediately could be the first step to happiness.

2) Plan your financial situation for the long-term. If quitting your job is what you need to move on to the next step in your life, that decision is unlikely if you don’t have some savings. Quitting a job without another employment opportunity lined up is sometimes necessary because it makes available more time to search for other opportunities and can contribute to your general happiness, making you more confident and allow you to project a better attitude to all who you encounter, including potential employers. Maybe sleeping on a friend’s couch for a few months is an option; there are many to explore.

3) Beware of emphasizing money as your guiding factor in life. Obviously money has varying importance in people’s lives. For people who have a spouse or dependents to support, money could be of greater necessity than someone who is single. If it means your income must go down to increase your happiness, and you can still live comfortably, it’s probably a healthy decision.

4) Continually challenge yourself (Never be intimated). Being confident can allow someone to make decisions they truly desire, but are difficult decisions to execute. As long as you’re being respectful and not harming others, recognize what you wish you could do and set incremental challenges for yourself to meet those goals. There will be setbacks, but with perseverance, in challenging yourself, you will build your confidence and probably your happiness.

5) Seeing decisions as binary can cause anxiety. Success and happiness are never reduced to one situation. Some people choose to define themselves by certain achievements like going to a particular school, working at a particular company or getting a particular score on a test. Most people don’t get exactly what they want and rather than allowing a disruption in plans to depress, it’s important to slow down, be creative and think about your range of options. What seems like a disappointment in the present could be a blessing in the future, or a detriment, depending on how the situation is approached.

6) Consulting professionals or friends for advice is helpful. Consulting professionals is expensive and consulting friends is not, so considering what you can afford is as important as considering which path can provide the most assistance.

7) Don’t be afraid of the unknown. Sometimes experiencing life without a grand plan can be a rewarding emotional experience. In our very structured society there is always a need to plan. Just because society emphasizes having a detailed plan does not mean you have to (in the short-term).

8) Focus on projecting positive energy. With friends, colleagues, family…. It’s healthier and emotionally easier to be happy. Determine your plan to maintain happiness. One example, there’s evidence that regular exercise increases positive emotions. If you tend to be negative, devise a plan.

9) Don’t blame yourself. If your life isn’t going as planned, don’t enter a downward spiral by attributing all perceived failures as your fault. If you are blaming yourself, you’re probably ignoring your many accomplishments. Be balanced with self-critique. Use it as a tool to make your future decisions.

10) Comparing yourself to others serves no logical purpose. Acknowledge who you are and what makes you unique, both positive and negative qualities. Placing your accomplishments only in the context of others is harmful, regardless of whether you’re doing it to belittle or build-up yourself.

When we’re confident we’re not scared to express ourselves — we don’t feel an urge to dampen our abilities by looking for approval elsewhere.  We’re not scared to publish a blog post or send an email without a review first.  We’re not scared to refactor a shit load of code.  We’re not scared to take a meeting with a big customer, or try a new, bold way of marketing something.  Confidence, in addition to enabling more happiness, sets us up to do beautiful, innovative things.

I can’t help but think of Burning Man when I think of confidence.  As I’ve said before, Burning Man is in part about radical self expression.  That self expression comes out because people don’t have social pressure that would otherwise impact their confidence.  There is no social norm at Burning Man, and hence all someone can be is their self.  The result is beautiful, innovative, and clever art.

If you’re in a position of influence, do your best to inspire confidence among your team.  The entire team will be happier, more innovative, and ultimately better employees.  And they’ll like you more for it, too.

This TED talk is somewhat relevant to inspiring confidence.  It talks about inspiring happiness and positivity, which goes very much along with inspiring confidence.

I decided to watch Forrest Gump on my plane ride back from New York. (I have a longer writeup about our trip coming soon.) I hadn’t seen the movie since I was a teenager. Apart from it possibly being the most amazing film I’ve ever seen, I found a lot of inspiration in it — mostly that we can’t doubt the direction our hearts take us.

If you haven’t seen it (go see it right now!!!) I’ll summarize quickly without giving anything away. Forrest Gump is a simple man who grew up in a semi-rural area of Alabama. He’s not a smart guy at all, yet he never doubts himself and never hesitates to pursue his dreams, which are extremely simple in nature.

Throughout the story Forrest finds a new interest in something, either through a promise or a serendipitous experience, and pursues without question and doubt. He’s not smart enough to think twice about whether or not he’s capable, and all he knows is that feeling in his heart that pushes him in a certain direction. He lacks the planning, distracted mind that would otherwise get in the way of his heart.

The story is fictional, and Forrest was very lucky to be in the right place at the right time over and over again. Yet I love being reminded that we need to listen to our heart and let it take us to places that are unknown, difficult, and scary. After all, if you’re doing something that isn’t challenging, it probably isn’t worth doing.

So many of us are too smart for our own good. We over think things far too much. We plan our future more than we live in the moment. We doubt our capabilities. Queue the broken record: stop all that and follow your heart.

An old Cherokee is teaching his grandson about life. “A fight is going on inside me,” he said to the boy.

“It is a terrible fight and it is between two wolves. One is evil – he is anger, envy, sorrow, regret, greed, arrogance, self-pity, guilt, resentment, inferiority, lies, false pride, superiority, and ego.”

He continued, “The other is good – he is joy, peace, love, hope, serenity, humility, kindness, benevolence, empathy, generosity, truth, compassion, and faith. The same fight is going on inside you – and inside every other person, too.”

The grandson thought about it for a minute and then asked his grandfather, “Which wolf will win?”

The old Cherokee simply replied, “The one you feed.”

Hard times open our hearts to others and let us be more compassionate and giving.  Sure, hard times are difficult and negative and dark.  But they bring us closer to those around us, to those of us that are struggling, too.

Problems aren’t worth solving if they’re not challenging.  A startup that isn’t difficult to build will have lots of competitors, or won’t tackle big enough problems to change the world.  I’m in this to change the world, so for better or worse I’m tackling very challenging problems.

During those challenges, though, it’s so easy to doubt yourself.  To think you’re not capable of doing it.  To think you’re not good enough, or don’t have the right experience or skills to carry on, or that you’ll screw it up anyway.  Bull shit.  You can do anything you put your mind to.  You just need to keep going.  Never stop.  And don’t let anything, especially yourself, stop you.

The most challenging things we do are what make us who we are. They bring out our nervousness and negative emotions, such as self doubt, and tune us into who we are and who we will become.  They make us stronger, more durable, and they open our hearts to those who are suffering and in difficult times, too.

I expect most of you have at least one challenge going on right now.  Maybe you’re unsure about your ability to write good code.  Or maybe you’re scared you’re pursuing the wrong major.  Or maybe you’re moving to a new city without a job lined up.  Times are hard.  But it’s these times that we’ll look back at when we’re older and be proud of.

And be proud right now.  Be proud for having the courage to be where you are right now, to be facing the challenge in the first place.  You’ve already overcome so much.  Just keep going, damnit.  Keep going until you’re sitting on top of the mountain you just moved, looking down at how you’ve made (or will make) an impact in the world.  Because you will if you haven’t already.  You just have to keep going.