Thanks for the feedback.
Now we're entirely off-topic, but it's a six-day-old thread so I doubt it'll bother anyone. I hadn't heard about the idea of him intentionally losing. Reminds me of the famous quote about New Coke: "We aren't that smart, and we aren't that stupid." Contextually meaning - I wonder how intentionally he ran for an office, worked to become the party nominee, then somehow was able to intentionally not sway voters his way for that election but then... get picked as the nominee later so they could actually try to win.
Just speaking from intuition rather than knowledge, seems more like a "glass half full" kind of strategy. Either he wins, or he loses but his rival weakens the opposing party, opening up future opportunities.
Further, the "successful lawyer" thing doesn't detract from the issue. Again, it's about reaching further than one has already. Striving, struggling, faltering, finding purchase, gaining a foothold, and succeeding. The context of Lincoln not being financially dependent on the appointment is, contextually, irrelevant. It's just that person's baseline.
A similar (fictional) story could be "I was a successful school teacher but I took the bar 17 times and became a lawyer! I then went on to the supreme court and also went on to fund research on dyslexia and change the lives of thousands because of it."
Certainly being a school teacher is itself already success, and if they'd given up on the Bar exam that wouldn't mean falling back on academics mean there was no failure.