How Will You Measure Your Life?

Posted by Andrew Savikas on February 1, 2017

If you’re tired of hearing the phrase “disruptive innovation” you can blame Clay Christensen. And while his book that popularized the term (The Innovators Dilemma ) is outstanding, there’s actually another one of his that I like even better. In How Will You Measure Your Life? Christensen (with co-authors James Allworth and Karen Dillon) expands on a lecture he gave on happiness and career satisfaction, prompted in part by several serious health scares.

Some of what the book offers at first feels like vanilla career and life advice:

In order to really find happiness, you need to continue looking for opportunities that you believe are meaningful, in which you will be able to learn new things, to succeed, and be given more and more responsibility to shoulder.

But what comes through as you get further along is wisdom forged in part from having witnessed many ostensibly “successful” people end up deeply unhappy following years in an unfulfilling career, along with the sense of urgency that comes from facing down your own mortality:

If the decisions you make about where you invest your blood, sweat, and tears are not consistent with the person you aspire to be, you’ll never become that person.

By itself the book’s advice about living life and choosing your career is practical and sound, and makes it well worth reading and reflecting on. But the reason I think it’s a great book is that in order help the reader apply his expertly honed analysis tools of business and strategy to one’s life and career, he has to explain all of them concisely along the way. For example, here’s The Innovators Dilemma in about 50 words:

I explained that disruption happens when a competitor enters a market with a low-priced product or service that most established industry players view as inferior. But the new competitor uses technology and its business model to continually improve its offering until it is good enough to satisfy what customers need.

And here he is on strategy (for a deeper dive into the subject, see Good Strategy, Bad Strategy):

A strategy? At a basic level, a strategy is what you want to achieve and how you will get there. In the business world, this is the result of multiple influences: what a company’s priorities are, how a company responds to opportunities and threats along the way, and how a company allocates its precious resources. These things all continuously combine, to create and evolve a strategy.

And then building on to that the lens of resource allocation:

You’re not implementing the strategy that you intend if you don’t spend your time, your money, and your talent in a way that is consistent with your intentions.

Here’s the kernel of his thinking around the “jobs to be done” theory of product development:

The mechanism that causes us to buy a product is “I have a job I need to get done, and this is going to help me do it.”

Further on, and using just a few paragraphs, the book ably explains the complex tension between growth and profitability that, if misunderstood, can choke a startup or bankrupt a titan:

At a basic level, there are two goals investors have when they put money into a company: growth and profitability. Neither is easy. Professor Amar Bhide showed in his “Origin and Evolution of New Business” that 93 percent of all companies that ultimately become successful had to abandon their original strategy—because the original plan proved not to be viable. In other words, successful companies don’t succeed because they have the right strategy at the beginning; but rather, because they have money left over after the original strategy fails, so that they can pivot and try another approach. Most of those that fail, in contrast, spend all their money on their original strategy—which is usually wrong.

The theory of good money and bad money essentially frames Bhide’s work as a simple assertion. When the winning strategy is not yet clear in the initial stages of a new business, good money from investors needs to be patient for growth but impatient for profit. It demands that a new company figures out a viable strategy as fast as and with as little investment as possible—so that the entrepreneurs don’t spend a lot of money in pursuit of the wrong strategy. Given that 93 percent of companies that ended up being successful had to change their initial strategy, any capital that demands that the early company become very big, very fast, will almost always drive the business off a cliff instead. A big company will burn through money much faster, and a big organization is much harder to change than a small one. Motorola learned this lesson with Iridium. That is why capital that seeks growth before profits is bad capital. But the reason why both types of capital appear in the name of the theory is that once a viable strategy has been found, investors need to change what they seek—they should become impatient for growth and patient for profit.

The overall result is a powerful and practical treatise on career satisfaction and happiness, one that — for better or worse — embraces the fact that so many of us end up with our personal lives and identity bound up tightly with our work, with guidance that applies equally to both:

You will be constantly pressured, both at home and at work, to give people and projects your attention. How do you decide who gets what? Whoever makes the most noise? Whoever grabs you first? You have to make sure that you allocate your resources in a way that is consistent with your priorities. You have to make sure that your own measures of success are aligned with your most important concern. And you have to make sure that you’re thinking about all these in the right time frame—overcome the natural tendency to focus on the short term at the expense of the long term.

A recurring theme in the book is the inherent tension between a deliberate, methodical strategy (creating a plan and tenaciously sticking to it) and being nimble and flexible (adopting an open attitude, sensing and responding to opportunities and threats as they emerge). The book’s advice? Neither extreme will work, and the best approach is to acknowledge that fundamental tension and use it to advantage (again, applying it both to work and home life):

The deliberate strategy and the new emerging opportunities fight for resources. On the one hand, if you have a strategy that really is working, you need to deliberately focus to keep everyone working together in the right direction. At the same time, however, that focus can easily cause you to dismiss as a distraction what could actually turn out to be the next big thing. Neither is inherently better or worse; rather, which you should choose depends on where you are on the journey. Understanding this—that strategy is made up of these two disparate elements, and that your circumstances dictate which approach is best—will better enable you to sort through the choices that your career will constantly present.

Tucked among the book’s high-level discussion about thoughtfully managing one’s career are stellar tactics for day-to-day management and leadership. For example, during a section on how to ask a team to prepare project plans and projections, the book offers this concrete advice (which I have used essentially verbatim several times as a CEO):

Ask the project teams to compile a list of all the assumptions that have been made in [their] initial projections. Then ask them: “Which of these assumptions need to prove true in order for us to realistically expect that these numbers will materialize?” At the top of the list should be the assumptions that are most important and least certain. Only after you understand the relative importance of all the underlying assumptions should you green-light the team—but not in the way that most companies tend to do. Instead, find ways to quickly, and with as little expense as possible, test the validity of the most important assumptions.

And the same section includes what has become one of my favorite questions to ask in myriad circumstances:

“What has to prove true for this to work?”

(A variation I’ve found helpful is for pressing someone to define success, asking them “what would have to be true for you to consider this project/role/product/launch/speech/conference/ad a success?”)

Another key theme that resurfaces multiple times in the book is the importance of watching where actual resources flow (be they time, money or attention) as the only legitimate evidence of a person or company’s true priorities:

Watch where your resources flow. If they’re not supporting the strategy you’ve decided upon, then you’re not implementing that strategy at all.

And later:

In the words of Andy Grove: “To understand a company’s strategy, look at what they actually do rather than what they say they will do.”

Yet the book offers a unique take on that message beyond just “pay attention to what you actually do vs. what you say” which is to point out the all-too-human tendency to pursue short-term gratification as a common cause for that kind of diversion from one’s intended path:

The trap many people fall into is to allocate their time to whoever screams loudest, and their talent to whatever offers them the fastest reward. That’s a dangerous way to build a strategy.

And here the same point made in the context of a company, rather than a career:

In fact, if you study the root causes of business disasters, over and over you’ll find a predisposition toward endeavors that offer immediate gratification over endeavors that result in long-term success.

But reinforcing that it’s not just nice advice, the book shows how that “watch how time is actually spent” message is explicitly tied to business success:

Over time, a company’s priorities must be in sync with how the company makes money, because employees must prioritize those things that support the company’s strategy, if the company is to survive. Otherwise the decisions they make will be in conflict with the foundation of the business.

And finally, as with many of the books covered on this blog, there’s a fundamental message about not just the importance of learning and improvement, but about the inevitability (and in many cases desirability!) of mistakes and messiness, whether it’s in finding the right business strategy or the right career path:

Getting something wrong doesn’t mean you have failed. Instead, you have just learned what does not work. You now know to try something else.


How Will You Measure Your Life? is available in multiple formats from Kobo.

Book cover image for How Will You Measure Your Life?