While transitioning from my last job, I took a small vacation in Sri Lanka and that time I was reading two books and thinking very deeply about both. Two books that couldn’t be more different.

One was Michael Singer’s The Surrender Experiment. The other was Robert Caro’s biography of Lyndon Johnson, The Path to Power.

I realised I was basically reading two opposite instruction manuals for life.

Singer’s story is wild. In the 1970s, he was living in a shed in Florida, meditating, building a small yoga temple. He came across a microcomputer. Taught himself to code, wrote some billing software for a local doctor, and before he knew it, he’s co-founded Medical Manager, a company that ended up dominating physician offices across America, IPO’ed in 1997, and got acquired by WebMD for ~$5 billion in 2002.

Michael Singer swore he never had a plan. He wrote two books about it.

I read his book The Untethered Soul a while back, and both The Surrender Experiment and Untethered Soul serve as play books on how to say yes and surrender to the flow of life. He just kept saying yes to whatever showed up.

While he was busy surrendering, some executives were cooking the books. The DOJ came knocking in 2009. He settled for $2.5 million before charges were dropped. Turns out saying yes to everything has its downsides.

LBJ is the complete opposite. This guy had his path to the White House mapped out while he was a kid.

Teacher’s college, congressional aide, House seat by 28, Senate next, presidency eventually. Every move was calculated. Relentlessly executed.

Caro describes LBJ holding meetings while sitting on the toilet because he couldn’t waste a single minute. The man was pathological about control.

In 1941, he made a rare mistake. During the final count of a special Senate election, he relaxed for once, went to his ranch instead of watching the vote count. Lost by 1,311 votes when his opponent’s team stuffed the last ballot boxes.

This never happened again. In 1948, he won his Senate seat after running his own ballot operation with military precision. Kept climbing until he became the President in 1963.

Reading these books in parallel messed with my head. Two guys who couldn’t be more different, and both reached the top of their fields.

Singer’s openness, and the willingness to say Yes without overthinking, created billion dollar opportunities he never could have planned for. But it also let fraud happen right under his nose.

LBJ’s iron grip got him to the presidency.

Steve Jobs said you can’t connect the dots looking forward, you can only connect them looking backward, once you’ve reached some end point in life and can see how the pieces fit together. But I think LBJ would disagree. You can connect the dots forward. You can obsess over them, and you can will that life into existence. But not everyone is LBJ.

Or even Singer.

We can build our life like Singer, one unexpected opportunity at a time. But some of us also crave LBJ’s certainty, his step by step master plan.

I went from tracking each day of my life, doing yearly OKRs, to now just following my gut. Saying Yes to things I am interested in. No concrete plans.

Yes, there is some vague direction, but no real sense of control. Easy to do now after a decade of saving, building a niche network, and developing a skill set, but Michael Singer did it from day one. For me there is this constant struggle between trying to control everything and letting go.

Maybe there’s a time for surrender and a time for control. The trick is knowing which moment calls for which approach.

Both men, Michael Singer and LBJ had opposite approaches, both led somewhere interesting. For now I am in my Singer mode: say yes, fuck around, see what happens.

I’ll run this playbook for a year and report back.