“Success is not final, failure is not fatal: it is the courage to continue that counts.”

Sure, we remember Churchill for his incredible achievements as a World War II leader but it’s worth noting he also made poor decisions both during WWI and WWII. The Dardanelles campaign during World War I is a particularly poignant example as Churchill strongly advocated this naval maneuver that tragically resulted in more than two hundred thousand lives being lost.

At the age of 40, Churchill resigned from his role as First Lord of the Admiralty, endured very bad press, and spent time in the proverbial career penalty box for this ill-considered decision. However, rather than being haunted by this mistake and retiring to the country to pursue a more private lifestyle, Churchill continued to lean forward and influence the political conversation throughout his career and ultimately earn an honored place in British history.

Churchill’s story reminds us of two important things. The first is that we all make bad decisions. While we no doubt all try to make the best decisions at all times, the reality is they won’t always prove to be right in the end. The second is that bad decisions should not prevent us from recovering, pressing on confidently, and making better decisions in the future.

Given the reality that leading a department or business often requires taking teams into new, unknown territory, it seems pretty impossible for any leader to avoid all missteps during one’s career. Like Churchill, bad decisions shouldn’t stop us from pursuing our dreams if, in the grand scheme of things, we actually have a knack for the career we pursue.

The courage to continue when you encounter failure has been a particular challenge for me. First, I tend to be quite self-critical — I struggle with the double whammy of being raised Catholic with a big dose of Confucianism. And as you might guess, I’ve made my fair share of mistakes, as I’ve had to make all sorts of decisions on topics from staffing to strategy over the years.

Annoyingly, all mistakes seem to share the unfortunate habit of looking even worse in hindsight. As a result, I have spent a lot of time beating myself up for poor decisions and have it affect my confidence. Reminding myself that running a business is a journey of ups and downs has helped. Knowing that Churchill could keep “buggering on” and make important, positive contributions after some poor decisions makes it even more real. Learn from mistakes, for sure, but don’t be fearful, or worse — run away — because of them.

Interestingly, one of Churchill’s early WWII mistakes helped prompt the resignation of his boss — Prime Minister Neville Chamberlain — and result in Churchill’s ascension into the Prime Minister role. Ah, the irony. That didn’t stop him from believing he was entirely ready for the role, though. And clearly, he was right. I suspect his bad decisions taught him as much as his successes in preparing him for his job of a lifetime.

PS – if you have a chance to visit London, definitely consider adding the Churchill Cabinet War Rooms to your list of places to visit. Right by Westminster Abbey and Big Ben, this warren of underground rooms that used to direct England’s movements is definitely worth the trip.

Conversation starters: What kinds of bad decisions have you made? What have you learned from them?

How I looked when trying to figure out what I’d do for the rest of my life. Different outfit though.

One of the scariest questions I faced during my senior year of college was: “What do you want to be when you grow up?”

That’s because I had no idea.

It was senior year, after three years of trudging up Science Hill to dutifully attend classes to fulfill pre-med requirements, when I finally admitted to myself and my parents that I really didn’t want to be a doctor. Didn’t love the science classes, didn’t love the idea of treating patients, didn’t love the idea of being in a lab doing research. Not exactly a great fit for the 4 plus how many ever additional years of training and money I’d need to spend to stick an MD after my name.

With my everlasting gratitude, my parents didn’t faint or hector me back onto the track. For those of you of Asian descent or with tiger parents, this was a big deal. And as my parents are also both doctors and most of their friends were also doctors, this was a VERY big deal.

Instead, they asked: so what do you want to do instead? Panicked, I went to my college career services office, tried to figure out what color my parachute was, and stumbled into an article that described management consulting as being a doctor for businesses.

It was simply because I could relate to that description, y’know the “doctor” part, that I wandered into my first real job… in management consulting. And that led to starting a publication with a friend, eating a lot of tunafish sandwiches, morphing the newsletter biz into an Internet business, eating even more tunafish sandwiches, and eventually landing venture capital backing with another friend. That funded our ticket to participate in that unique comedic drama known as dot-com bubble, with an eventual sale to a pretty big company. Surprising many people, including myself, I’ve stayed with that buyer and now find myself running one of its divisions with offices in the US and UK, and with colleagues around the world. [exhale]

Long story short, I would have NEVER predicted the career that I have today. And I’d say that many of my friends would not have been able to predict their current careers or the journeys they have taken to get there.

If you are struggling to figure out the answer to the BIG question of what you want to be when you grow up, don’t get too paralyzed trying to answer it. Instead, just start exploring options, ask questions and learn all you can about those jobs and yourself. Hopefully, something will resonate and feel like the right thing to do and you’ll give it a try. And so your career will begin — your first dot along a journey that will have certainly its ups and downs but should always teach you something about what you like and don’t like, what you’re good at and what you’re not so good at, and what you want to try next.

Steve Jobs nailed it with his Stanford commencement speech when he said “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. This approach has never let me down, and it has made all the difference in my life.” It’s not easy to hear when you’re not sure of where your dots will be or how they’ll connect, but as my mother always says, “everything will come out just fine.” I’ve found as I’ve accumulated more dots, she and Steve are absolutely right.

One caveat: No matter what dot you’re at along your career journey,  go for it. Try hard to succeed. That way, you can reach your dot’s boundary sooner and decide whether you want to stay, get to the next level, or decide it’s not for you and move on to your next dot. Half-hearted efforts are uninspiring to yourself and everyone around you. (And yes, we can tell.) If you find that you’re not giving it a full effort, figure out why that’s happening and do something about it. Address it by changing your work situation or moving on.

“What do you want to be when you grow up?” is one of the few questions that you will hear throughout your life from well-meaning relatives, friends and even yourself. That’s okay because do you really want to do the same thing from the age of 20, 30 or even 50 or 70? And so to that pervasive question, here’s my answer: I’m looking forward to finding out.

Conversation starters: What did you want to be when you grew up and what journey have you taken? What advice would you give to others facing that journey of building and connecting dots?

What a herniated disc looks like Not mine. 3mm to the left and my doc said I wouldn’t have even been able to tell. Lucky me.

I’m a doer and an idea person.

For the last two weeks, I’ve had to put a lot of the doing on hold as I herniated a disc in my back. Sadly, it wasn’t due to bungee jumping — I just  stood up after a phone call at work. Not quite sure how I’m going to avoid that activity in the future.

So I’ve spent the last 14 days at home, working by email and phone but not seeing anyone except my family. As I’ve gotten better and emerged from the excruciating pain that had been dulled by a haze of Percocets and muscle relaxants, I finally started to really use Facebook to make up for the lack of people interactions for the first time ever. And I enjoyed it, especially when I realized social media is more of a conversation where you can add your voice to a stream rather than a medium where you need to prepare perfectly worded declarations.

And when I could manage my pain without dulling my brain, I took to watching TED videos to occupy my non-working hours. TED offers an amazing digital library of ideas, explained by incredibly articulate people in 18-minute nuggets on a huge range of topics.

In particular, I was moved by talks from Sheryl Sandberg, Amy Cuddy, Jane Goodall, Chris Anderson and Candy Chang, Each person had a different message: women should seek success at the workplace, fake it until you become it, sophisticated language distinguishes us as a species, crowd-accelerated learning is an amazing outcome of the Internet, and think about what you want to do before you die. And they helped think about a question I’ve long asked myself, which is — why are there not more women in business speaking up?

As one of those silent women business leaders, and inspired by those voices, I’ve decided to finally ignore the reasons why not, assume the Wonder Woman power pose, and start to share my thoughts to help start conversations about business and who knows what else. Let the experiment begin.

Conversation starters: Why do you think women in business don’t speak up more? Why did you start blogging? What’s preventing you from starting a blog?