While the overall destination of Brexit was reasonably foreseeable what has caught me out is the lack of will to decide on a long term destination for the U.K. The willingness to fudge and to postpone making any choices that entail any trade offs has been spectacular. Even now the Withdrawal Agreement and Political Declaration Leave almost anything on the table from Norway to something more like Canada. Issues around the border in Ireland are significantly due to the limits on the fudge the EU is prepared to accept where they apply there.
Surprised by May
I honestly thought she was smarter than to trap herself into corners with red lines like she did, alienate “people of nowhere” and to fail to listen to the experienced advice around her like Ivan Rodgers.
The other surprise was May’s decision not to reach across to Labour to make them complicit in the deal and to provide her with more routes through Parliament. There were two main opportunities to do this; after the referendum and again after the general election. She could have said “Things have changed”, acknowledged her lack of majority and sort to find a compromise option. She could then have shared blame for aspects that were softer than the ERG wanted, could have blamed Labour if the walked away and critically potentially had a majority without DUP or ERG. The only thing she would have lost would be being able to act as if Corbyn was unfit to be near responsibility, a threat to be used against all who oppose her except Labour, maybe that was too high a price for her to pay.
Sufficient Progress (December 2017)
That this stage was crossed without it seems the DUP or the ERG understanding the contents and melting down at that point was a surprise as the now unacceptable Withdrawal Agreement was essentially set out at that point. It did also seem at times like May didn’t understand what it meant either as she claimed the backstop was something that “no British PM” could agree to despite having done so in December 2017 and then proceeding to do so again in December 2018.