It Shouldn’t Get Easier

Anderson’s knife can cut anything, taking a chunk from everything in the land.

Master Terrence’s strokes remove less with each cut.

Greg LeMond once said, “It never gets easier, you just go faster.” This quote has been a rosary for me, a source of contemplation and meditation over the years. I think of it every time a new problem reveals itself as an echo of something I thought I already solved.

When I started Puppet, everyone I worked with stressed the need for me to recognize my position as founder and CEO, to bring people with me. The summer before I stepped down, more than a decade into practicing this skill, it still showed up in every coaching session. Not because I haven’t improved — but because it is a life skill that I can improve at every year and still die with more work in front of me than behind.

I found it incredibly hard to hire those first few people. I second-guessed myself, was slow, looked like a fool, felt an even bigger one, and finally made bets based on too little information. When I rebuilt the executive team in my last year, I second guessed myself, went too slowly, made what looked like basic mistakes, and felt incompetent the whole time.

This isn’t a coincidence. It’s not a sign of my incompetence. It’s the exact opposite: It shows that I never let things get easier, instead I kept my intensity up and always focused on going faster.

LeMond knew how to win. You train, you work, you focus, and all that effort delivers leverage. What you did yesterday when giving 100%, you can do today giving only 97%. What do you do with that 3%?

If you want to win, you reinvest it. In what? Counter-intuitively, exactly what got you that leverage in the first place.

For each and every one of us, there are two kinds of skills: Those it’s worth devoting our lives to, and those it’s not. A given pursuit can be less important because it doesn’t matter to you, because you’ll never be good enough at it, or because you just don’t like it. Those that matter, though, are a perfect intersection of your love, your abilities, and your values. They will reward any amount of investment by making you better at what you care most about, and are best at.

You have to love it because you really can’t devote the time and energy needed to dominate unless you like the work. You need at least some ability. You don’t need to start with a natural talent, but you are most likely to be rewarded for investing in areas that come easier than when you’re starting at the bottom. And your investments have to match your values. Some people care most about skills that earn them money, others about having an impact on people’s lives, and yet others want to build. You have to believe that what you’re investing in will help you spiritually, not just materially. It’s the only way you can convince yourself to work as hard as you need to.

Yes, there absolutely are things you will never be good at that you have to invest in. When I started Puppet, I was an outright liability in some areas, such as business operations. I had to get better at those. But I was never confused into thinking I would be great at them. That’s what team building is for.

Given two skills, one where you’re 8/10 and the other where you’re 3/10, where do you invest? Some might recommend the skill you suck at.

Not me. If that skill mattered, you would never have gotten hired in the first place. The reason you have a job is because of your 8/10 skill. Get 10% better at your weakness, and wow, you’re at 3.3/10. Big whoop. Get 10% better at your strength? You’re at 8.8/10. That’s a huge difference.

But getting 10% better in your area of expertise is fantastically difficult. It’s your life’s work.

I am suspicious of people who say the hard things are easy. What I hear is not that it’s easy, but that they’re not trying very hard. Or they’re too embarrassed to be honest.

Greg LeMond was the fastest cyclist in the world, but never stopped trying to ride faster.

Miyamoto Musashi won more than 200 individual duels with a sword, but never stopped trying to cut faster.

Excellence requires perpetual intensity. You should be confident enough in your strengths to admit that it’s hard. It should be hard. It’s the only way to get better.