“If You Had Only 10 Years to Live, What Would You Stop Doing?”

Jim Collins’ Question on The Tim Ferriss Show Shook Me to My Core

James Do
Iteration
5 min readJan 11, 2021

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Silhouette of a person balancing on a rock in front of a sunset
Photo by Aziz Acharki

Today, after a monthlong hiatus from listening to the Tim Ferriss Show podcast, I jumped back in with episode #483, featuring Jim Collins. Collins is a business mentor, an entrepreneurship researcher, and the best-selling author of Good to Great, Built to Last, and How the Mighty Fall. Those first two books profoundly shaped my thinking in business and entrepreneurship, so I was excited to listen to what Collins had to say.

Throughout the episode, Collins describes himself as being rather uninterested in providing answers, but instead concerned with offering deep questions that lead his mentees to think hard about what they do and why.

At one point, he asks, “If you had 10 years to live, what would you stop doing?”

That question shook me to my core, and made me re-examine my relationships and daily decisions. While 10 years is less than the time most of us have left on Earth, the remainder of your lifespan is also some arbitrarily short amount: in a big-picture sense, 50 years is not really much more than 10. Moreover, the next 10 years will happen only once, so it truly is a one-shot, last-chance opportunity to use that 10 years to its potential.

I reflected on Collins’ question as I finished cooking tonight’s Blue Apron dinner (tilapia with farro and broccoli), and throughout the evening while winding down.

Here are the answers I have so far.

1. Relationships

The first answer is that I’d stop being afraid to lean into relationships with openness, candor, kindness, and strong boundaries. I have improved this skill set significantly over the last year to great positive impact within my family, but know that I have a long way to go.

Let me be specific. While I am on good terms with my parents, I want my relationships with my parents to be better than simply “on good terms”. This year, my mom and dad will turn 60 and 66, respectively. Now 32, I am starting to understand how years and even decades can fly by in an instant.

That means I will text them more often. Organize video conference calls with my parents and siblings. Send them care packages to show I’m thinking about them, even if we don’t see each other in person for months at a time.

While relationships are hard, I actually find them to be conceptually simple. So, I have fairly high confidence in this diagnosis of what I need to do.

To me, my career and broader impact are more complex.

2. Work

So far, I’ve come up with two answers to Collins’ question when it comes to work, though I suspect more answers will arise as I continue to reflect in the coming weeks.

First, I need to cut out behaviors that reduce my effectiveness when it comes to projects that can increase my impact exponentially. And second, I need to refocus my business on what makes us special — and therefore uniquely impactful.

As Collins says, being a great clockmaker is more impactful than being the world’s best time-teller. In my work as a personal development consultant to high school students and their families, I am a great time-teller. So far, however, I am not a great clockmaker, as I have yet to discover to successfully distribute my work to the masses.

Over the course of the evening, I reflected on my relative strengths and weaknesses. By simply being a metaphorical time-teller, I have accomplished a lot in my education and career — graduating from a top-five university and a top-ten law school, working as a corporate attorney at two of the nation’s most prestigious law firms, co-founding two educational businesses, and becoming a millionaire shortly after turning 29.

If I can accomplish that as a time-teller, how much could I create as a clock maker? Being the clock maker involves an entirely different skill set, but in my view it’s worth it to discover how my team can replicate some portion of our work for the masses.

Mind you, my team and I have been working on this problem of scaling up for years now. And after several failed attempts, I will admit — I’m a little tired. Our current and future efforts will require me to really push myself to go for it if they are to have a hope of succeeding. I am the boss of myself and my team, which comes with plenty of blessings; one of the curses, of course, is the responsibility to actually manage yourself when the going gets rough.

And so, where do I stand today? Most significantly, my relatively poor sleep habits lead to lower energy levels during the day, which suppresses my ability to energetically lead my team’s projects to exponentially scale our reach and impact.

In addition, I now realize I have allowed my business to become slightly more commoditized, less unique, than it was in previous years. It’s not a dramatic shift, but it is enough that I have decided with my team that we will invest heavily in changes to our service this year to become more of what makes us special.

So: If I knew I’d live only 10 more years, what would I stop doing?

First, I’d cut out the behaviors that diminish my energy and make it harder for me to build that critically important clockmaker skill set. For now, that means taking steps to sleep earlier: winding down earlier, staying off screens each evening, and waking up to embrace early mornings more often to keep my sleep schedule from drifting too late in a world where we no longer show up to an office at a predetermined time.

I’d also double down on what makes my company’s value so unique to the families we work with. We’ve strayed from our niche a little in the last year, and it’s time to not only go back to where we were, but to double down on becoming even more unique than before. There’s really no time to waste in providing the kind of impact that our company literally exists to provide.

These are my answers after an evening of reflection. No doubt others will arise. I plan to keep Collins’ question lingering in my psyche in the coming weeks and months, to continue discovering the ways in which I could be more focused on what matters in this very finite life.

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James Do
Iteration

My life’s work is to help people discover and focus on theirs. Founder of Cortex Education. Investor. Former attorney.