Many years ago, I cold-emailed Salesforce founder/CEO Marc Benioff. I was 15 years old and starting a CRM software company like his. Would he meet to give me some advice? I wasn’t the only one inspired by Marc’s vision of the “end of software” at the time. But I may have been one of a smaller group who was especially inspired by the fact that Marc had started companies as a teenager back in his day.

To my surprise, he replied, we met for breakfast, and it kicked off a series of meals that we shared over several years. He eventually wrote the foreword to my first book.

At one of our early breakfasts, Marc told me something I’ve never forgotten. I remember the moment exactly. I was wearing a suit and tie, which in hindsight was kind of crazy. (“I hope you don’t normally wear a suit and tie when you go to school,” he said with a laugh.) He ordered pancakes. He had been telling me about swimming with dolphins in Hawaii, what he learned from Larry Ellison, and riffs on spirituality.

He then told me: “Ben, people in Silicon Valley are ridiculously smart. Super, super smart. You’re not going to be able to out-smart people. You have to figure out how to win in some other way.”

I was not lacking in self-regard for my own intelligence at the time. But when he said it, I knew immediately it was true. I may be generally smart but general smarts is like vanilla ice cream. Vanilla ice cream is a fine dessert but it’s not going to win a chef any culinary awards. And IQ is IQ. No amount of study would allow me to compete head-to-head in an IQ contest with the highest IQ people in the tech industry. If you regularly feel like you’re the highest IQ person in the room, you’re hanging out in the wrong rooms. The tech industry may not be as intellectually intense as academic disciplines like chemistry but there are plenty of rooms with off-the-charts IQ people in them, and those are the rooms you want to be in — even if they make you feel a bit inferior at times.

As I contemplated Marc’s comment in the months afterwards, my first plan was that I could out-work everyone in order to be successful. I may not be smarter than everyone else, but surely I could out-work them, right? Then I realized that there were people who could work harder than me, and already were. Damn those people who only need 4 hours of sleep a night!

Marc’s advice is not obvious to a lot of people. These days I still meet many super smart and super hard working people in business who, deep down, are mystified as to why they haven’t been more successful in their careers. They really believe their raw intelligence and/or their work ethic should be enough to carry the day.

Anyway, in the years after that breakfast, in my early 20’s, I came upon two deeper insights that ultimately are how I answer and incorporate Marc’s advice to me.

First, I could get good at facilitating the intelligences of other smart people. You don’t have to be smarter than someone in order to enable that person to be all they can be. Most business efforts involve teams — multiple smart people interacting with each other. If you can develop the ability to work with different kinds of smart people, to bring them together, to facilitate all the IQ points sloshing about, you can be a really high-impact player. In fact, I’d argue this is what great CEOs do well. They’re not the smartest person in the company. But they get all the other smart people to play well together. Arguably, that’s the most important job of all on a team.

Some years ago, my friend Auren Hoffman emailed me and said there had been a cancellation at an event he was hosting in New Orleans and asked if I wanted to take the open spot. I said yes. As I reviewed the list of other attendees, it was obvious that I was the B-list invite to an event filled with other A-listers. I was excited but a bit nervous. Then, a few days before the event, Auren asked me to moderate a 90 minute session with 15 accomplished people at the event. At first I thought he had sent the email to the wrong person; I think I was 17 years old at the time. The people in my session were all much smarter and more experienced than me. But I accepted the task, and I did fine. I did good, even. And it emboldened me with the confidence that I could credibly be a participant in a large meeting even if on paper I wasn’t the smartest or most experienced person.

The second insight I internalized in the years after that breakfast with Marc Benioff was that I could get good at combining multiple skills in unique combinations. Scott Adams once wrote that to be successful you need to either be the very best in one field or the top 25% of skill in multiple fields. In other words, if you’re not world class at something but you’re really good at a couple things and the combination of those two skills produces a valued offering in the market, you can be successful. Example: You can either be one of the top pianists in the world and succeed through sheer singular talent, or be a really, really good pianist (if not world-class) and also be really, really good at marketing (or some other skill), combine the two really-good skills, and success will follow.

Given my curiosity and knack for synthesis, I saw a path for me that would involve getting really good a couple things and combining them in interestingly unique ways (versus becoming solely obsessed with one skill area). I could take basic intelligence and work ethic, and layer on top of that very strong — even if not truly world-class — abilities in entrepreneurship and written / oral communication, for example, and that could produce some interesting career opportunities. (That specific skill combination helped me be a complementary partner to Reid Hoffman over the four years I worked for him.) In the years since then, I’ve continued to hone different skills that in combination in an attempt to develop a unique competitive advantage in whatever market I’m playing in.

Like a lot of important wisdom, Marc’s comment to me at breakfast in San Francisco all those years ago sounded simple. The depth of its truth took years for me to appreciate.

My friend Rob Montz created a 10 minute mini-documentary called The Quarterlife User Manual. Contains fantastic advice on careers and life delivered in an engaging format. It’s very much consistent with The Startup of You. Cal Newport, Jon Haidt, and I are featured, among others.

The things that make you happy (friends! good health! sex!) are not the same things that make your life seem meaningful (sacrifice, service, goals.). I think about the difference by comparing the effect that staying at a luxury hotel has on you (happy) vs. the effect of training really hard for a marathon and then completing it has on you (meaning).

Robin Hanson has a round up of the distinction. Consider a few excerpts from him, drawn from the research.

What a happy life is:

People who are happy tend to think that life is easy, they are in good physical health, and they are able to buy the things that they need and want. While not having enough money decreases how happy and meaningful you consider your life to be, it has a much greater impact on happiness. The happy life is also defined by a lack of stress or worry … [and] is associated with selfish behavior.

What a meaningful life is:

The study participants reported deriving meaning from giving a part of themselves away to others and making a sacrifice on behalf of the overall group. … Having more meaning in one’s life was associated with activities like buying presents for others, taking care of kids, and arguing. … They also worry more and have higher levels of stress and anxiety in their lives than happy people. Having children, for example, is associated with the meaningful life, … but it has been famously associated with low happiness among parents. …

Just the other day, Adam Alter wondered in this recent online New Yorker piece about whether the poor have more meaningful lives than the rich:

Happiness, after all, doesn’t explain the popularity of ultramarathons, mountaineering, and Tough Mudder events—or the sacrifices parents must make to raise children. Some of the most rewarding life experiences are popular because they favor meaningful hardship over simple pleasure.

When contemplating this happiness/meaning distinction in the context of career strategy, I have a few reactions.

First, entrepreneurship tends to increase meaning but not necessarily happiness. The day-to-day of an entrepreneurial journey — or any long-term project — can be crazy stressful. Most entrepreneurs I know who are striving for big world-changing outcomes are not actually happy most days. But the long term change they believe they’re enacting, and the personal legacy that it will create, adds a sense of meaning. That makes the journey worth doing from their perspective.

Second, I wonder if there’s a viable career strategy that emphasizes either concept at different times in life. For example, there are stages in life when you consciously focus on meaning and stages when you focus on happiness. Early on in your life perhaps you seek meaning with audacious career goals and sacrifice; later in life you optimize for day-to-day happiness with a low-stress job.

Third, if you had to pick just one path, my advice would be: choose a career that’s meaningful, but weave in happiness habits as much as possible. By “happiness habits” I mean the small tactical things — like keeping a gratitude journal — that are the subject of most of commentary on the happiness topic.

NCAA basketball teams that are behind by one point at halftime are more likely to win than teams that are one point ahead.

That’s the intruiging finding of two professors who studied more than 6,000 games. The results are the same even when taking into account homecourt advantage, the team winning percentages, and which team got the ball to start the second half. The article says:

So what may be driving this pattern? The reason is motivation. Being behind by a little leads to victory because it increases effort. Not only do teams down by a point at the break score more than their opponents in the second half, they do so in a particular way. They come out of the locker room fired up and make up for most of the point deficit in the first few minutes of the second half.

In sports and politics, you have a clear competitor and where you stand relative to that competitor is transparently displayed on the scoreboard or in the polls. How about in business? The authors of the study say, “Companies competing to win contracts or research prizes would be wise to focus employees on ways their competitors are a little ahead. Similarly, strategically taking breaks…when one is slightly behind should increase effort.”

Perhaps. An underdiscussed dilemma for leaders in the world of business is the extent to which they should clearly define / highlight competitors to employees, and if so, how to frame the competitors’ progress vis-a-vis you — i.e., should a competitor be portrayed as slightly ahead of you (the equiavalent of one point ahead at halftime) so as to maintain the troops’ sense of urgency? Or is this letting you be defined by the enemy and motivated by extrinsic causes? And when does the “underdog hunger” of being just behind first place turn into demoralized hopelessness?

Finally, there’s a related question at the level of individual career. Should you think of the start-up of you as slightly trailing someone else’s career in terms of achievement to keep you maximimally motivated? There will always be someone who’s done more, and keeping your eye on that person — directly comparing yourself to that person — will keep you pushing. Then again, this approach can generate the kind of envy that consumes high achievers. An alternative to is create an entrepreneurial life so unique to you that it destroys reasonable comparisons. Unlike a lawyer who has a million direct peers with whom to compare himself, walk alone on your own path. If you do, envy goes down, genuine happiness for others’ achievements goes up, and success and progress becomes more about achieving individually defined and intrinsically motivated goals. But, realistically, you probably won’t exert your maximum effort, either. We’re social animals. Competition fuels us to be all we can be.

Bottom Line: In basketball, it seems that being behind by a little at half-time yields the greatest possible second-half effort. In business and life, the extent to which you compare yourself to the competition — and how such comparison drives underlying motivation and ultimate effort — is trickier.

(Photo: Flickr)